阅读说明：本技术 用于碱性基底的可固化组合物 (Curable compositions for alkaline substrates ) 是由 A·克拉默 U·布尔克哈德特 于 2019-11-11 设计创作，主要内容包括：本发明涉及包含至少一种具有封闭的羟基基团的聚醚作为塑化剂的可固化组合物在至少一种碱性基材上的用途。该可固化组合物存储稳定,易于处理,固化后具有很高的弹性并且没有显示任何分离或迁移的趋势。它能实现弹性粘合,密封或涂覆碱性基材,如特别是新鲜或生的混凝土或水泥砂浆,而不会出现由塑化剂皂化引发的难闻气味。(The present invention relates to the use of a curable composition comprising at least one polyether having blocked hydroxyl groups as plasticizer on at least one basic substrate. The curable composition is storage stable, easy to handle, highly elastic after curing and does not show any tendency to separate or migrate. It enables elastic bonding, sealing or coating of alkaline substrates, such as in particular fresh or raw concrete or cement mortar, without the occurrence of unpleasant odours caused by saponification of the plasticizer.)

1. Use of a curable composition comprising at least one polyether having blocked hydroxyl groups as a plasticizer on at least one alkaline substrate having a pH of at least 10 when wetted with water.

2. Use according to claim 1, characterized in that the alkaline substrate is fresh concrete, fresh cement mortar, fresh lime mortar or fresh lime or silicate paint.

3. Use according to either of claims 1 and 2, characterized in that the blocked hydroxyl group is selected from the group consisting of acetal groups, ester groups, acetate groups, carbonate groups and carbamate groups.

4. Use according to any one of claims 1 to 3, characterized in that in the polyether 70% to 100% by weight of the recurring units consist of 1, 2-propylenoxy groups and 0 to 30% by weight of recurring units consist of 1, 2-ethyleneoxy groups.

5. Use according to any one of claims 1 to 4, wherein the polyether having blocked hydroxyl groups has an average molecular weight M_nIn the range of 600 to 10000g/mol, determined by Gel Permeation Chromatography (GPC) with polystyrene as standard and tetrahydrofuran as mobile phase, using a refractive index detector and evaluated from 200 g/mol.

6. Use according to any one of claims 1 to 5, wherein the polyether having blocked hydroxyl groups is derived from at least one hydroxyl-functional polyether selected from the group consisting of:

polyoxypropylene monols starting with alcohols, especially n-butanol, having an OH number in the range from 25 to 90mg KOH/g,

polyoxypropylene glycol having an OH number in the range of 12 to 155mg KOH/g,

-a polyoxypropylene triol, optionally end-capped with ethylene oxide, starting with trimethylolpropane or in particular with glycerol, having an average OH functionality of 2.2-3 and an OH number in the range from 22 to 230mg KOH/g, and

sugar alcohol-initiated polyoxypropylene polyols having an average OH functionality of 3-6, in particular sugar alcohol-initiated polyoxypropylene polyols using threitol, erythritol, xylitol, mannitol or sorbitol as the starting molecule.

7. Use according to any one of claims 1 to 6, characterized in that the curable composition comprises at least one polymer containing isocyanate and/or silane groups.

8. Use according to any one of claims 1 to 7, characterized in that the curable composition comprises at least one polymer containing isocyanate groups and at least one latent curing agent.

9. Use according to any one of claims 1 to 8, characterised in that the curable composition comprises at least one calcium carbonate-based filler.

10. Use according to any one of claims 1 to 9, characterized in that the curable composition comprises:

10-50% by weight of a polymer containing isocyanate and/or silane groups,

20 to 60% by weight of a filler, and

10-40% by weight of a polyether having blocked hydroxyl groups.

11. Use according to any one of claims 1 to 10, characterized in that the curable composition is one-component and moisture-curable.

12. Method of gluing or sealing or coating comprising the steps of:

(i) providing a curable composition as claimed in any one of claims 1 or 3 to 11,

(ii) providing at least one basic substrate as claimed in any of claims 1 or 2,

(iii) contacting the curable composition with a basic substrate,

(iv) curing the composition.

13. An article obtained by the method of claim 12.

14. The article of claim 13 which is a splice floor bonded to a screed of concrete or cement mortar.

15. An adhesive joint obtained by the use according to any one of claims 1-11 or the method according to claim 12, comprising a cured composition and at least one substrate adhered to the composition, the surface of the substrate being alkaline at the moment of contacting the composition and having a pH value of at least 10 when wetted with water.

Technical Field

The present invention relates to curable compositions based on polyurethane or SMP, which are suitable for use on alkaline substrates, such as in particular fresh (raw) concrete or cement mortar, especially as adhesives, sealants or coatings.

Prior Art

Curable compositions based on polyurethane or silane-modified polymers (SMP) are commonly used in the construction industry as adhesives, sealants or coatings. Typical substrates (substrates) for applying such products are derived from building materials such as concrete or cement mortar in combination with cement, lime or silicates. When these building materials have only recently been processed, substrates in the form of foundations, walls, screeds (Estrichen), renders, etc. are still fresh, they have a clearly alkaline-reactive surface with a pH of 10 or more, since the hydroxides contained therein have not been carbonated. Fresh concrete is also known as "new" or "green" or "wet". To protect the curable composition from contact with alkaline surfaces, it may be sufficiently aged or pretreated prior to application of the composition, for example by neutralization with silicofluorides (e.g. fluorosilicates) or by sealing with the aid of primers (primers) such as epoxy coatings. In practice, however, this is not usually done in order to save time and money. In the boundary layer, saponification of the components of the curable composition may occur under alkaline conditions, which may result in the emission of an offensive odor. In particular, plasticizers present in most of these compositions, typically fatty alcohol dicarboxylates such as diisodecyl phthalate (DIDP), diisononyl-cyclohexane-1, 2-Dicarboxylate (DINCH) or di (2-ethylhexyl) adipate (DOA), react sensitively. The saponification thereof leads to the release of fatty alcohols having a highly unpleasant odor, and the fatty alcohols migrate into the pore structure of the substrate and evaporate therefrom or are washed out into the environment and generate a musty odor over a long period of time. This persistent odor burden is observed particularly when the parquet flooring is bonded to a fresh cementitious screed by means of a resilient polyurethane or SMP adhesive.

Summary of The Invention

It is therefore an object of the present invention to provide a curable composition for alkaline substrates which is suitable for use as an adhesive, sealant or coating in the construction field and which overcomes the disadvantages of the prior art.

This object is achieved by a curable composition as claimed in claim 1. The curable composition includes at least one polyether having a blocked hydroxyl group as a plasticizer. They can be prepared by simple methods from readily available raw materials, have good compatibility in the compositions, have a high elasticizing effect, and release the underlying hydroxy-functional polyether in the event of possible saponification on alkaline substrates, are odor-neutral and do not have any other troublesome effects. The polyether having blocked hydroxyl groups promotes good storage stability and processability of the curable composition and has no tendency to migrate or separate, which means that it does not cause any sticky surface or spot formation on the substrate. The curable compositions are storage stable, easy to handle, highly elastic after curing and do not show any tendency to separate or migrate. It is capable of elastically bonding, sealing or coating alkaline substrates, such as in particular fresh or green concrete or cement mortar, without the occurrence of unpleasant odours caused by saponification of the plasticizer.

Thus, by using the invention, substrates having highly alkaline surfaces can also be bonded or sealed or coated reliably and permanently, in which case the adhesive bond obtained does not cause troublesome odor emissions and is very resistant to migration effects.

Other aspects of the invention are subject matter of further independent claims. Particularly preferred embodiments of the invention are the subject matter of the dependent claims.

Detailed Description

The present invention provides the use of a curable compound comprising at least one polyether having blocked hydroxyl groups as plasticizer on at least one basic substrate having a pH of at least 10 when wetted with water.

"curable composition" means a composition containing a polymerizable macromolecule that is curable or brought into a state of increased mechanical strength by a crosslinking reaction of its reactive groups.

"polyether" means a molecule or a group of oligomeric and/or polymeric molecules consisting essentially of alkyleneoxy repeat units.

"blocked hydroxyl group" refers to a hydroxyl group that is converted by a chemical reaction to a group that is not reactive with isocyanate groups.

"plasticizer" means a difficult volatile material that does not chemically bond into the polymer during curing and imparts a plasticizing effect to the cured polymer.

"silane group" means a silyl group bonded to an organic group and having one to three, especially two or three, hydrolyzable alkoxy groups on the silicon atom.

"silane" refers to both organoalkoxysilanes and tetraalkoxysilanes bearing one to three organic substituents per silane group. Silanes having an organic group bearing one or more hydroxyl, isocyanato, amino, or mercapto groups in addition to the silane group are referred to as "hydroxysilanes", "isocyanatosilanes", "aminosilanes", or "mercaptosilanes", respectively.

The names of substances starting with "poly", such as polyamines, polyols or polyisocyanates, refer to substances which formally contain two or more of the functional groups appearing in their name per molecule.

"molecular weight" refers to the molar mass (in grams/mole) of a molecule or residue of a molecule. "average molecular weight" refers to the number average molecular weight (M) of a polydispersed mixture of oligomeric or polymeric molecules or molecular residues_n). The average molecular weight is typically determined by Gel Permeation Chromatography (GPC) against polystyrene standards.

Curable compositions referred to as "storage stable" or "storable" are compositions that can be stored in suitable containers at room temperature for extended periods of time, typically at least 3 months to 6 months and longer, without their application properties or performance properties changing during storage to the extent associated with their use.

"Room temperature" means a temperature of 23 ℃.

In particular, the pH of the basic substrate wetted with water is determined using pH paper.

The alkaline substrate is preferably a fresh but not yet fully carbonated substrate based on cement, lime (calcium hydroxide) and/or silicate (water glass).

Particularly preferably, the alkaline substrate is fresh concrete, fresh cement mortar, fresh lime mortar or fresh lime or silicate paint.

Concrete is said to be "fresh" as long as it is still capable of undergoing alkaline reactions at a pH of 10 or higher. The time for which the concrete remains fresh depends on its setting rate and the ambient temperature. The time period typically varies in the range of 1 to 10 days. Fresh concrete is also referred to as "new" or "green" or "wet".

The curable composition comprises at least one polyether having blocked hydroxyl groups as plasticizer.

Polyethers having blocked hydroxyl groups are substantially free of unblocked hydroxyl groups. By "substantially free" is meant here that 95%, preferably 99%, in particular 99.9%, most preferably 100% of the hydroxyl groups present are blocked.

Polyethers having blocked hydroxyl groups are included in the curable composition as plasticizers. Therefore, it preferably does not contain a reactive group that undergoes a crosslinking reaction with moisture or with a component present in the composition. It is especially free of isocyanate groups and silane groups.

Polyethers having blocked hydroxyl groups are in particular liquid at room temperature.

The polyethers having blocked hydroxyl groups preferably have a viscosity at20 ℃ in the range from 30 to 5000 mPas, more preferably from 40 to 2000 mPas, particularly preferably from 50 to 1000mPas, in particular from 50 to 500 mPas. The viscosity here was measured using a cone and plate viscometer with a cone diameter of 25mm, a cone angle of 1 °, a cone tip-plate distance of 0.05mm, a shear rate of 10s^-1. Such polyethers are easy to handle and give the composition high elasticity.

The blocked hydroxyl groups are preferably selected from acetal, ester, acetyl, carbonate and carbamate groups. These acetal, ester, acetyl, carbonate or carbamate groups preferably have from 1 to 15 carbon atoms.

Particularly preferred are ester or urethane groups. The hydroxyl groups can be converted into these groups in a particularly simple manner.

Very particular preference is given to ester groups, especially those having from 1 to 8 carbon atoms.

Most preferred are acetate groups. Polyethers having blocked hydroxyl groups in the form of acetate groups are of low viscosity, can be obtained in a very particularly simple manner and are particularly inexpensive. If saponified on an alkaline substrate, odor-neutral, hydroxy-functional polyethers and acetates are released, the latter being nonvolatile in alkaline medium and having no noticeable odor.

Also preferred are carbamate groups, especially phenyl carbamate groups or p-toluenesulfonyl carbamate groups. Polyethers having such blocked hydroxyl groups have a manageable viscosity and can be prepared in a particularly simple manner.

Preferred as acetal groups are 1- (isobutoxy) ethoxy or tetrahydropyran-2-oxy or tetrahydrofuran-2-oxy, especially 1- (isobutoxy) ethoxy.

The preferred acetyl ester group is an acetoacetate group.

Preferred carbonate groups are methyl carbonate groups.

They have low viscosity and can be obtained from inexpensive raw materials.

The polyethers having blocked hydroxyl groups preferably have 1, 2-ethyleneoxy, 1, 2-propyleneoxy, 1, 3-propyleneoxy, 1, 2-butyleneoxy or 1, 4-butyleneoxy, in particular 1, 2-propyleneoxy, as repeating units.

Preferably, from 70% to 100% by weight, in particular from 80% to 100% by weight, of the recurring units consist of 1, 2-propylenoxy and from 0 to 30% by weight, in particular from 0 to 20% by weight, of recurring units consist of 1, 2-ethyleneoxy.

Particularly preferably, 100% of the recurring units consist of 1, 2-propyleneoxy.

Such polyethers are readily available, are hydrophobic and are therefore particularly suitable as components of curable compositions having low water absorption and good stability.

Average molecular weight M of polyethers having blocked hydroxyl groups_nPreferably in the range from 600 to 10000g/mol, more preferably 700-5000g/mol, especially 800-2500g/mol, as determined by Gel Permeation Chromatography (GPC) using polystyrene as standard and tetrahydrofuran as mobile phase, a refractive index detector and an evaluation from 200 g/mol.

Such polyethers with blocked hydroxyl groups have a viscosity which is easy to handle and do not cause migration effects, emissions or odors in the curable composition.

The polyethers having blocked hydroxyl groups are preferably derived from at least one hydroxyl-functional polyether selected from

Polyoxypropylene monols starting with alcohols, especially starting with n-butanol, having an OH number in the range from 25 to 90mg KOH/g, preferably from 50 to 80mg KOH/g,

polyoxypropylene diols having OH numbers in the range from 12 to 155mg KOH/g, preferably 22 to 125mg KOH/g, in particular 45 to 125mg KOH/g,

-a polyoxypropylene triol, optionally ethylene oxide-terminated, starting from trimethylolpropane or especially glycerol, having an average OH functionality of 2.2-3 and an OH number in the range from 22 to 230mg KOH/g, preferably from 56 to 165mg KOH/g, and

-sugar alcohol-initiated polyoxypropylene polyols having an average OH functionality of 3-6, in particular using threitol, erythritol, xylitol, mannitol or sorbitol as starter molecules. Such polyethers having blocked hydroxyl groups are useful asSPX-80 (from Sanyo chem.Ind.) is commercially available.

Among these, preference is given to polyoxypropylene monoalcohols or polyoxypropylene diols starting from alcohols, in particular n-butanol.

Particularly preferred is polyoxypropylene glycol. These are particularly inexpensive.

Preferred polyethers having blocked hydroxyl groups can be prepared in a simple manner from readily available starting materials, have a low viscosity and enable curable compositions having good storage stability, easy handling and high flexibility and elasticity in the cured state without any tendency to migration effects, emissions or odors.

Polyethers having blocked hydroxyl groups are obtained in particular by reacting at least one hydroxyl-functional polyether with at least one suitable blocking agent for hydroxyl groups.

For the reaction, the blocking agent is used in at least stoichiometric amounts relative to the hydroxyl groups, so that the hydroxyl groups are essentially completely blocked and the polyether thus obtained is essentially free of hydroxyl groups. For blocking, the customary methods for the individual reactive groups are used, optionally with catalysts or solvents. If the blocking reaction forms elimination products, they are removed from the reaction mixture by suitable methods, in particular by distillation.

Suitable blocking agents are nucleophilic compounds which undergo addition or substitution reactions with hydroxyl groups.

Particularly suitable are vinyl ethers, carboxylic acids, phosgene, carboxylic esters or carboxylic anhydrides, diketene, 2, 5-trimethyl-4H-1, 3-dioxin-4-one, alkyl acetoacetates, dialkyl carbonates, monoisocyanates, (meth) acrylamides, methylene malonates or cyanoacrylates.

Preference is given to vinyl ethers, such as, in particular, methyl vinyl ether, ethyl vinyl ether, isopropyl vinyl ether, butyl vinyl ether, isobutyl vinyl ether, isopropenyl methyl ether, isopropenyl ethyl ether, 2, 3-dihydrofuran or 3, 4-dihydro-2H-pyran, with particular preference to isobutyl vinyl ether, 2, 3-dihydrofuran or 3, 4-dihydro-2H-pyran, in which a blocked hydroxyl group in the form of an acetal group is formed. The reaction is preferably carried out in the presence of an acid, in particular hydrochloric acid, sulfuric acid, phosphoric acid or sulfonic acid, as catalyst, optionally in the form of an acidic ion exchange resin.

Preference is given to carboxylic acids, phosgene, carboxylic esters or carboxylic anhydrides in which the blocked hydroxyl group is formed in the form of an ester group. Among them, carboxylic acid anhydride or carboxylic acid ester, especially acetic anhydride, is preferable.

In the case of acetic anhydride as blocking agent, acetic acid is liberated in the reaction and blocked hydroxyl groups in the form of acetate groups are formed.

In the case of isopropenyl acetate as blocking agent, acetone is liberated in the reaction, likewise forming blocked hydroxyl groups in the form of acetate groups.

Preference is also given to diketene, 2,2, 5-trimethyl-4H-1, 3-dioxin-4-one or sterically hindered alkyl acetoacetates, such as, in particular, tert-butyl acetoacetate, and to the formation of blocked hydroxyl groups in the form of acetyl ester groups.

Preference is also given to dialkyl carbonates, in particular dimethyl carbonate, and to the formation of blocked hydroxyl groups in the form of carbonate groups, in particular methyl carbonate groups.

Also preferred are monoisocyanates in which the blocked hydroxyl groups are formed in the form of urethane groups. Preferred are phenyl isocyanates or p-toluenesulfonyl isocyanates.

Suitable hydroxy-functional polyethers are in particular those having an average OH functionality of from 1 to 6 and an average molecular weight of from 500-.

Preference is given to polyoxypropylene monoalcohols having an OH number of from 25 to 90mg KOH/g, preferably from 50 to 80mg KOH/g, in particular those starting from alcohols, in particular methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, tert-butanol, pentanol, hexanol, 2-ethylhexanol, lauryl alcohol, myristyl alcohol, palmityl alcohol, allyl alcohol, cyclohexanol, benzyl alcohol or phenol. Among these, the polyoxypropylene monols starting from alkyl alcohols are preferred, especially starting from methanol, ethanol or n-butanol. Particularly preferred are n-butanol-initiated polyoxypropylene monols having an average molecular weight of 650-. Polyoxypropylene monols starting with n-butanol are commercially available, for example as100-20B、100-40B or100-85B (all from Dow DuPont Inc.).

Also preferred are polyoxypropylene diols having OH numbers in the range from 12 to 155mg KOH/g, preferably from 22 to 125mg KOH/g, in particular from 45 to 125mg KOH/g.

Further preferred are trimethylolpropane or, in particular, glycerol-initiated, optionally ethylene oxide-capped polyoxypropylene triols having an average OH functionality of from 2.2 to 3 and an OH number of from 22 to 230mg KOH/g, preferably from 56 to 165mg KOH/g.

Further preferred are polyoxypropylene polyols starting from sugar alcohols having an average OH functionality of at least 3, especially 3-6, especially using threitol, erythritol, xylitol, mannitol or sorbitol as starting molecule.

The curable composition preferably comprises at least one curable polymer having polyether building blocks, especially predominantly polyoxypropylene building block moieties. Polyethers having blocked hydroxyl groups are particularly compatible in such curable compositions and show hardly any tendency to segregate or migrate.

The curable composition preferably comprises at least one polymer containing isocyanate and/or silane groups.

The polymers containing isocyanate and/or silane groups preferably have an average molecular weight of 1000-30000g/mol, in particular 2000-20000 g/mol.

It is preferably liquid at room temperature.

In a preferred embodiment, the composition contains at least one polymer containing isocyanate groups. Such compositions are also known as "polyurethane compositions".

Suitable polymers containing isocyanate groups are obtained in particular from the reaction of at least one polyol with a superstoichiometric amount of at least one diisocyanate. The reaction is preferably carried out under moisture-excluding conditions at a temperature of from 20 to 160 c, in particular from 40 to 140 c, optionally in the presence of a suitable catalyst.

The NCO/OH ratio is preferably in the range of 1.3/1 to 10/1. The monomeric diisocyanates remaining in the reaction mixture after the reaction of the OH groups can be removed, in particular by distillation.

If the excess monomeric diisocyanate is removed by distillation, the NCO/OH ratio in the reaction is preferably in the range from 4/1 to 7/1, and the isocyanate group-containing polymer obtained after distillation preferably contains not more than 0.5% by weight, more preferably not more than 0.3% by weight, of monomeric diisocyanate. The monomeric diisocyanates are removed in particular by short-path distillation under reduced pressure.

If excess monomeric diisocyanate is not removed from the polymer, the NCO/OH ratio in the reaction is preferably in the range of 1.3/1 to 2.5/1.

The content of isocyanate groups in the resulting polymer is preferably from 0.5 to 10% by weight, in particular from 1 to 5% by weight, more preferably from 1 to 3% by weight, and the average molecular weight is from 1500 to 20000g/mol, in particular from 2000 to 15000 g/mol.

The polymers are optionally prepared by using plasticizers or solvents in combination, in which case the plasticizers or solvents used do not contain any groups reactive toward isocyanates.

Preference is given to aliphatic, cycloaliphatic or aromatic diisocyanates, in particular 1, 6-Hexamethylene Diisocyanate (HDI), 1-isocyanato-3, 3, 5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate or IPDI), perhydro 2,4 '-and/or 4,4' -diphenylmethane diisocyanate (H)₁₂MDI), 4' -diphenylmethane diisocyanate (which optionally has 2,4' -and/or 2,2' -diphenylmethane diisocyanate Moieties (MDI)), or 2, 4-toluene diisocyanate or a mixture thereof with 2, 6-Toluene Diisocyanate (TDI).

Particularly preferred are HDI, IPDI, MDI or TDI, or mixtures thereof.

Suitable polyols are commercially available polyols or mixtures thereof, in particular

Polyether polyols, in particular polyoxyalkylene diols and/or polyoxyalkylene triols, in particular polymerization products of ethylene oxide or 1, 2-propylene oxide or 1, 2-or 2, 3-butylene oxide or oxetane or tetrahydrofuran or mixtures thereof, where they can be polymerized by means of starter molecules having two or more active hydrogen atoms, such as, in particular, water, ammonia or compounds having a plurality of OH-groups or NH-groups, such as, for example, 1, 2-ethanediol, 1, 2-or 1, 3-propanediol, neopentyl glycol, diethylene glycol, triethylene glycol, the isomeric dipropylene glycols or tripropylene glycols, the isomeric butanediols, pentanediols, hexanediols, heptanediols, octanediols, nonanediols, decanediols, undecanediols, 1, 3-or 1, 4-cyclohexanedimethanol, bisphenol A, hydrogenated bisphenol A, 1,1, 1-trimethylolethane, 1,1, 1-trimethylolpropane, glycerol or aniline, or mixtures of the aforementioned compounds. Also suitable are polyether polyols having polymer particles dispersed therein, in particular those having styrene-acrylonitrile-particles (SAN) or polyurea particles or polyhydrazodicarbonamide Particles (PHD).

Preferred polyether polyols are polyoxypropylene diols or triols, or so-called ethylene oxide-capped (EO-capped or EO-capped) polyoxypropylene diols or triols. The latter are polyoxyethylene-polyoxypropylene-mixed polyols, which are obtained in particular by: the polyoxypropylene diol or triol is further alkoxylated with ethylene oxide after the end of the polypropoxylation reaction and is thus provided with primary hydroxyl groups.

Preferred polyether polyols have an unsaturation of less than 0.02mEq/g, especially less than 0.01 mEq/g.

Polyester polyols (also known as oligoester alcohols), which are prepared according to known methods (in particular polycondensation of hydroxycarboxylic acids or lactones or polycondensation of aliphatic and/or aromatic polycarboxylic acids with di-or polyhydric alcohols). Preference is given to polyester diols resulting from the reaction of diols, such as, in particular, 1, 2-ethanediol, diethylene glycol, 1, 2-propanediol, dipropylene glycol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, neopentyl glycol, glycerol, 1,1, 1-trimethylolpropane or mixtures of the abovementioned alcohols, with organic dicarboxylic acids or anhydrides or esters thereof, such as, in particular, succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid, dodecanedicarboxylic acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, 1, 2-cyclohexanedicarboxylic acid, 1, 3-cyclohexanedicarboxylic acid or 1, 4-cyclohexanedicarboxylic acid or mixtures of the abovementioned acids, or polyester polyols formed from lactones, such as, in particular,. epsilon. -caprolactone. Particularly preferred are polyester polyols derived from adipic acid or sebacic acid or dodecanedicarboxylic acid and hexanediol or neopentyl glycol.

Polycarbonate polyols, such as those obtainable, for example, by reaction of the alcohols mentioned above (used for the construction of the polyester polyols) with dialkyl carbonates, diaryl carbonates or phosgene.

Block copolymers with at least two hydroxyl groups, having at least two different blocks with polyether, polyester and/or polycarbonate structures of the type described above, in particular polyether polyester polyols.

Polyacrylate polyols and polymethacrylate polyols.

Polyhydroxy-functional fats or oils, such as natural fats and oils, especially castor oil; or polyols obtained by chemical modification of natural fats and oils, so-called oleochemical, for example epoxy polyesters or epoxy polyethers obtained by epoxidation of unsaturated oils and subsequent ring opening with carboxylic acids or alcohols, or polyols obtained by hydroformylation and hydrogenation of unsaturated oils; or polyols obtained from natural fats and oils by a decomposition process (e.g. alcoholysis or ozonolysis) and subsequent chemical bonding (e.g. by transesterification or dimerization) of the decomposition products or derivatives thereof obtained. Suitable breakdown products of natural fats and oils are, in particular, fatty acids and fatty alcohols and fatty acid esters, in particular methyl esters (FAME), which can be derivatized, for example, by hydroformylation and hydrogenation to hydroxy fatty acid esters.

Polyhydrocarbon polyols, also known as oligohydrocarbonols, such as, in particular, polyhydroxyfunctional polyolefins, polyisobutenes, polyisoprenes; polyhydroxy-functional ethylene-propylene-copolymers, ethylene-butylene-copolymers or ethylene-propylene-diene-copolymers, such as those prepared by Kraton Polymers; polyhydroxyl-functional diene (in particular 1, 3-butadiene) polymers, which can in particular also be prepared by anionic polymerization; copolymers of polyhydroxyfunctional dienes (e.g. 1, 3-butadiene) or mixtures of dienes and vinyl monomers (e.g. styrene, acrylonitrile, vinyl chloride, vinyl acetate, vinyl alcohol, isobutene or isoprene), in particular polyhydroxyfunctional acrylonitrile/butadiene copolymers, for example acrylonitrile/butadiene copolymers which can be terminated, in particular, by epoxides or amino alcohols and carboxyl groups (for example by the nameCTBN or CTBNX or ETBN commercially available from Emerald Performance Materials); or a hydrogenated polyhydroxy-functional bisAn olefinic polymer or copolymer.

Also particularly suitable are mixtures of polyols.

Preferred are polyether polyols, polyester polyols, polycarbonate polyols, poly (meth) acrylate polyols or polybutadiene polyols.

Particular preference is given to polyether polyols, polyester polyols, in particular aliphatic polyester polyols, or polycarbonate polyols, in particular aliphatic polycarbonate polyols.

Especially preferred are polyether polyols, especially polyoxyalkylene polyols.

Most preferred are polyoxypropylene diols or triols or ethylene oxide capped polyoxypropylene diols or triols.

Preference is given to polyols having an average molecular weight in the range from 400 to 20000g/mol, preferably from 1000 to 15000 g/mol.

Preferred are polyols having an average OH-functionality in the range of 1.6 to 3.

Preferred are polyols that are liquid at room temperature.

It is also possible in the preparation of the polymers containing isocyanate groups to use jointly certain amounts of difunctional or polyfunctional alcohols, in particular 1, 2-ethanediol, 1, 2-propanediol, 1, 3-propanediol, 2-methyl-1, 3-propanediol, 1, 2-butanediol, 1, 3-butanediol, 1, 4-butanediol, 1, 3-pentanediol, 1, 5-pentanediol, 3-methyl-1, 5-pentanediol, neopentyl glycol, dibromo, 1, 2-hexanediol, 1, 6-hexanediol, 1, 7-heptanediol, 1, 2-octanediol, 1, 8-octanediol, 2-ethyl-1, 3-hexanediol, diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, 1, 3-or 1, 4-cyclohexanedimethanol, ethoxylated bisphenol-A, propoxylated bisphenol-A, cyclohexanediol, hydrogenated bisphenol-A, dimer fatty acid alcohols, 1,1, 1-trimethylolethane, 1,1, 1-trimethylolpropane, glycerol, pentaerythritol, sugar alcohols such as especially xylitol, sorbitol or mannitol, or sugars such as especially sucrose, or alkoxylated derivatives of the abovementioned alcohols or of mixtures of the abovementioned alcohols.

The polymers containing isocyanate groups preferably have an average molecular weight in the range from 1500 to 20000g/mol, in particular from 2000 to 15000 g/mol.

In addition to the isocyanate group-containing polymer, the composition may comprise at least one oligomeric isocyanate or in the form of MDI which is liquid at room temperature.

Suitable oligomeric isocyanates are, in particular, HDI biurets such asN100 or N3200 (from Covestro AG),HDB or HDB-LV (from Vencor Holding SAS) or24A-100 (from Asahi Kasei Corp.); HDI isocyanurates, e.g.N3300, N3600 or N3790 BA (all from Covestro AG),HDT, HDT-LV or HDT-LV2 (from Vencorex Holding SAS),TPA-100 or THA-100 (from Asahi Kasei Corp.) orHX (from Tosoh Corp.); HDI uretdiones, e.g.N3400 (from Covestro AG); HDI iminooxadiazinediones, e.g. HDIXP 2410 (from Covestro AG); HDI allophanates, e.g.VP LS 2102 (from Covestro AG); IPDI isocyanurates, e.g. in solutionZ4470 (from Covestro AG) or in the form of a solidT1890/100 (from Evonik Industries AG); TDI oligomers, e.g.IL (from Covestro AG); or mixed isocyanurates based on TDI/HDI, e.g.HL (from Covestro AG).

The MDI forms which are liquid at room temperature are 4,4'-MDI which is liquefied by partial chemical modification, in particular carbodiimidization or uretonimine formation or adduct formation with polyols, or mixtures of 4,4' -MDI purposely produced or produced by the production process with other MDI isomers (2,4'-MDI and/or 2,2' -MDI) and/or with MDI oligomers and/or MDI homologues (polymeric MDI or PMDI).

In a preferred embodiment of the present invention, the curable composition comprises at least one latent curing agent in addition to at least one polymer comprising isocyanate groups. Such polyurethane compositions exhibit particularly little foaming during the curing process.

Preferred latent curing agents are ketimines, aldimines or oxazolidines, especially oxazolidines or aldimines, most preferably aldimines.

Is preferably of the formulaWherein y is 2 or 3, A is an organic group having 2 to 23 carbon atoms, and B is an organic group having 6 to 30 carbon atoms.

A is preferably alkylene optionally having a cyclic component or divalent or trivalent polyoxyalkylene having from 5 to 15 carbon atoms, in particular 1, 6-hexylene, (1,5, 5-trimethylcyclohex-1-yl) methane-1, 3 or alpha, omega-polyoxypropylene having an average molecular weight of from 170 to 300g/mol or trimethylolpropane-initiated tris (omega-polyoxypropylene) having an average molecular weight of from 330 to 500 g/mol.

B is preferably an organic radical having from 7 to 22 carbon atoms, in particular 2, 2-dimethyl-3-acetoxypropylidene, 2-dimethyl-3-lauroyloxypropylidene, 2-dimethyl-3- (N-morpholino) propylidene, benzylidene or alkyl-substituted benzylidene, in particular 4-decylbenzylidene, 4-undecylbenzylidene, 4-dodecylbenzylidene, 4-tridecylbenzylidene or 4-tetradecylbenzylidene, where the 4-alkyl radical is predominantly branched.

Particularly preferably, B is a radical having at least 15 carbon atoms, especially 2, 2-dimethyl-3-lauroyloxypropylidene or alkyl-substituted benzylidene. This aldimine is odourless.

Formula (II)Especially by reacting an aldimine of the formula A- (NH)₂)_yWith an aldehyde of the formula O ═ B and removing the water of condensation.

Preferred amines A- (NH)₂)_yAre aliphatic or cycloaliphatic primary diamines or triamines, especially 1, 6-hexamethylenediamine, isophoronediamine, alpha, omega-polyoxypropylene-diamine, having an average molecular weight of 200 to 350g/mol, especiallyD-230 (from Huntsman Corp.), or trimethylolpropane-initiated tris (. omega. -polyoxypropylene amine), especiallyT-403 (from Huntsman Corp.).

Preferred as aldehyde O ═ B are aldol esters of carboxylic acids, in particular 2, 2-dimethyl-3-acetoxypropionaldehyde, 2-dimethyl-3-lauroyloxypropionaldehyde, 2-dimethyl-3- (N-morpholino) propionaldehyde, benzaldehyde or alkyl-substituted benzaldehydes, in particular 4-decanylbenzaldehyde, 4-undecanylbenzaldehyde, 4-dodecanylbenzaldehyde, 4-tridecylbenzaldehyde or 4-tetradecylbenzaldehyde, where the 4-alkyl radical is predominantly branched, and mixtures of these alkyl-substituted benzaldehydes.

Upon contact with moisture, amino groups and possibly hydroxyl groups are released from the latent curing agent, which react with the isocyanate and act as a crosslinker. During this process aldehydes or ketones are released.

In the case of the preferred aldehydes of the formula O ═ B where B is a long-chain group, in particular a group having 15 or more carbon atoms, this does not cause any odor problems and remains in the composition after curing, in which it has good compatibility and can act as further plasticizers.

Crosslinking by means of latent curing agents has no CO evolution compared to direct reaction of water and isocyanate₂This greatly reduces the tendency of bubbles to form during curing.

In another preferred embodiment, the curable composition contains at least one organic polymer containing silane groups. Such polymers are also referred to as "silane-modified polymers" (SMP) and such compositions are therefore also referred to as SMP compositions.

The organic polymer containing silane groups preferably has the formula

Silane group (a)

Wherein

R^aIs a linear or branched monovalent hydrocarbon radical having from 1 to 5 carbon atoms, especially methyl or ethyl,

R^bis a linear or branched monovalent hydrocarbon radical having from 1 to 8 carbon atoms, especially methyl, and

x has a value of 0 or 1 or 2, preferably 0 or 1, in particular 0.

The methoxy silane groups have the advantage here that they are particularly reactive. The advantage of the ethoxysilane groups is that they are toxicologically advantageous and in particular storage-stable.

Particularly preferred are trimethoxy silane groups, dimethoxymethyl silane groups or triethoxy silane groups.

Most preferred are trimethoxy silane groups or triethoxy silane groups.

Preferred organic polymers containing silane groups are polyolefins or polyesters or polyamides or poly (meth) acrylates or polyethers or mixtures of these polymers. The silane groups may be located at the side or end of the chain and are attached to the organic polymer through carbon atoms.

More preferably, the organic polymer containing silane groups is a polyether containing silane groups.

"polyether containing silane groups" means an organic polymer containing at least one silane group, the polymer chain of which predominantly has polyether units, in particular 1, 2-oxypropylene units. In addition to the polyether units, it is possible in particular to include urethane groups, urea groups, thiourethane groups, ester groups or amide groups.

The polyethers containing silane groups preferably contain at least 50% by weight, in particular at least 70% by weight, more preferably at least 80% by weight, of 1, 2-oxypropylene units.

Methods for preparing suitable silane group-containing polyethers are known to those skilled in the art.

In a preferred method, the polyether containing silane groups may be obtained from the reaction of an allyl-containing polyether with a hydrosilane, optionally chain extended using, for example, a diisocyanate.

In another preferred method, the polyether containing silane groups may be obtained from the copolymerization of alkylene oxide and epoxy silane, optionally with chain extension using, for example, a diisocyanate.

In another preferred process, the polyether containing silane groups may be obtained from the reaction of a polyether polyol with an isocyanatosilane, optionally with the use of a diisocyanate for chain extension.

In another preferred process, polyethers containing silane groups are obtainable by reacting polyethers containing isocyanate groups with aminosilanes, hydroxysilanes or mercaptosilanes. Polyethers containing silane groups resulting from the process are particularly preferred. The process allows the use of large amounts of commercially available, inexpensive starting materials, so that different polymer properties can be obtained, in particular high stretchability, high strength, low modulus of elasticity, low glass transition point or high weatherability.

Particularly preferably, polyethers containing silane groups are obtainable by reaction of polyethers containing isocyanate groups with aminosilanes and/or hydroxysilanes and/or mercaptosilanes.

Suitable polyethers containing isocyanate groups are obtainable in particular by reacting polyether polyols, in particular polyoxyalkylene diols or triols, preferably polyoxypropylene diols or triols, with superstoichiometric amounts of diisocyanates.

Preferably, the reaction between the diisocyanate and the polyether polyol is carried out with exclusion of water at a temperature of from 50 ℃ to 160 ℃, optionally in the presence of a suitable catalyst, wherein the diisocyanate is metered in such that its isocyanate groups are present in stoichiometric excess compared to the hydroxyl groups of the polyol. In particular, the excess of diisocyanate is selected such that a free isocyanate group content of 0.1 to 5% by weight, preferably 0.2 to 4% by weight, more preferably 0.3 to 3% by weight, based on the entire polymer, is obtained after reaction of all hydroxyl groups.

Preferred diisocyanates are those already mentioned above. Particularly preferred is IPDI or TDI. Most preferred is IPDI. Thus, polyethers containing silane groups are obtained which have particularly good light resistance.

Particularly suitable as polyether polyols are polyoxypropylene diols having an unsaturation of less than 0.02mEq/g, in particular less than 0.01mEq/g, and an average molecular weight in the range from 400 to 25000g/mol, in particular from 1000 to 20000 g/mol.

In addition to polyether polyols, it is also possible to use other polyols, in particular polyacrylate polyols, and also low molecular weight diols or triols in proportions.

Suitable aminosilanes for reaction with the polyethers containing isocyanate groups are primary aminosilanes and especially secondary aminosilanes. Preferred are 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, 4-aminobutyltrimethoxysilane, 4-amino-3-methylbutyltrimethoxysilane, 4-amino-3, 3-dimethylbutyltrimethoxysilane, N-butyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, primary aminosilanes (e.g.3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane or N- (2-aminoethyl) -3-aminopropyltrimethoxysilane) and Michael acceptors (e.g.acrylonitrile, (meth) acrylates, (meth) acrylamides, maleic or fumaric diesters, methyl esters, ethyl esters, Citraconic or itaconic diesters, in particular dimethyl or diethyl N- (3-trimethoxysilylpropyl) aminosuccinate) adducts. Also suitable are the analogs of the above-mentioned aminosilanes having ethoxy groups instead of methoxy groups on silicon.

Suitable hydroxysilanes for reaction with polyethers containing isocyanate groups are obtainable in particular from the addition reaction of aminosilanes on lactones or cyclic carbonates or lactides.

Preferred hydroxysilanes obtained in this way are N- (3-triethoxysilylpropyl) -2-hydroxypropionamide, N- (3-trimethoxysilylpropyl) -2-hydroxypropionamide, N- (3-triethoxysilylpropyl) -4-hydroxypentanamide, N- (3-triethoxysilylpropyl) -4-hydroxyoctanamide, N- (3-triethoxysilylpropyl) -5-hydroxydecanamide or N- (3-triethoxysilylpropyl) -2-hydroxypropylcarbamate.

Other suitable hydroxysilanes may be obtained from the addition reaction of an aminosilane to an epoxide or the addition reaction of an amine to an epoxysilane.

Preferred hydroxysilanes obtained in this way are 2-morpholino-4 (5) - (2-trimethoxysilylethyl) cyclohexan-1-ol, 2-morpholino-4 (5) - (2-triethoxysilylethyl) cyclohexan-1-ol or 1-morpholino-3- (3- (triethoxysilyl) propoxy) propan-2-ol.

Suitable mercaptosilanes for reaction with polyethers containing isocyanate groups are, in particular, 3-mercaptopropyltrimethoxysilane or 3-mercaptopropyltriethoxysilane.

Also suitable as polyethers containing silane groups are commercially available products, in particular the following: MS Polymer^TM(products available from Kaneka Corp., inter alia, S203H, S303H, S227, S810, MA903 and S943); MS Polymer^TMOr Silyl^TM(products from Kaneka Corp.; in particular SAT010, SAT030, SAT200, SAX350, SAX400, SAX725, MAX450, MAX951 types);(available from Asahi Glass Co. Ltd.; especially the S2410, S2420, S3430, S3630 products); SPUR +^*(products available from Momentive Performance Materials Inc.; especially model 1010LM,1015LM,1050 MM); vorasil^TM(available from Dow DuPont Inc.; especially products type 602 and 604);(from Covestro AG; especially products S XP 2458, S XP 2636, S XP 2749, S XP 2774 and S XP 2821),(from Evonik Industries AG; especially products of type Seal 100, Bond 150, Bond 250), Polymer ST (from Hanse Chemie AG/Evonik Industries AG, especially products of type 47,48,61,61LV,77,80, 81);STP (products from Wacker Chemie AG; in particular E10, E15, E30, E35).

Particularly preferably, the polyether containing silane groups is obtained from the reaction of at least one polyether containing isocyanate groups with at least one aminosilane and/or hydroxysilane and/or mercaptosilane.

Preferably, the aminosilane and/or hydroxysilane and/or mercaptosilane is chosen from dimethyl N- (3-trimethoxysilylpropyl) aminosuccinate, diethyl N- (3-trimethoxysilylpropyl) aminosuccinate, dimethyl N- (3-triethoxysilylpropyl) aminosuccinate, diethyl N- (3-triethoxysilylpropyl) aminosuccinate, N- (3-trimethoxysilylpropyl) -2-hydroxypropionamide, N- (3-triethoxysilylpropyl) -2-hydroxypropionamide, 3-mercaptopropyltrimethoxysilane and 3-mercaptopropyltriethoxysilane.

Preferred embodiments of the organic polymers containing silane groups enable compositions having good storage stability, rapid curing and particularly good mechanical properties, in particular high elasticity and drawability, as well as good strength and high heat resistance.

Preferably, the curable composition additionally comprises one or more further ingredients selected in particular from fillers, tackifiers, drying agents, thickeners and catalysts.

Suitable fillers are, in particular, ground or precipitated calcium carbonate, optionally coated with fatty acids, in particular stearates, barite (Schwerspate), quartz flour, quartz sand, dolomite, wollastonite, calcined kaolin, layered silicates such as mica or talc, zeolites, aluminum hydroxide, magnesium hydroxide, silicon dioxide (including highly dispersible silicon dioxide from pyrogenic processes), cement, gypsum, fly ash, industrially produced carbon black, graphite, metal powders such as aluminum, copper, iron, silver or steel, PVC-powder or hollow spheres.

Preference is given to calcium carbonate, calcined kaolin or industrially prepared carbon black, optionally coated with fatty acids, especially stearates.

In a preferred embodiment, the composition comprises at least one filler based on calcium carbonate. This is particularly advantageous in the case of polyethers having blocked hydroxyl groups in the form of ester groups, for example, in particular acetate groups, since any acid which may be liberated therefrom by hydrolysis, in particular, for example, acetic acid, is bound by calcium carbonate and thus does not cause any odor emission.

The compositions preferably contain from 5% to 50% by weight, in particular from 10% to 40% by weight, of a calcium carbonate-based filler.

Suitable adhesion promoters are, in particular, aminosilanes, such as, in particular, 3-aminopropyltrimethoxysilane, 3-aminopropyldimethoxymethylsilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyldimethoxymethylsilane, N- (2-aminoethyl) -N' - [3- (trimethoxysilyl) propyl ] ethylenediamine or the like having ethoxy groups instead of methoxy groups, and furthermore N-phenyl-, N-cyclohexyl-or N-alkylaminosilanes, mercaptosilanes, epoxysilanes, (meth) acryloylsilanes, acid anhydride silanes, urethane silanes, alkylsilanes or iminosilanes, oligomeric forms of these silanes, adducts of primary aminosilanes with epoxysilanes or (meth) acryloylsilanes or anhydride silanes, amino-functional alkylsilsesquioxanes, in particular amino-functional methylsilsesquioxanes or amino-functional propylsilsesquioxanes, or titanates.

Particularly suitable as adhesion promoters for compositions containing isocyanate groups are epoxysilanes, such as, in particular, 3-glycidoxypropyltrimethoxysilane or 3-glycidoxypropyltriethoxysilane, (meth) acrylsilanes, anhydride silanes, urethane silanes, alkylsilanes or iminosilanes or oligomeric forms of these silanes.

Suitable drying agents for compositions comprising polymers containing silane groups are, in particular, tetraethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane or organoalkoxysilanes having a functional group in the alpha-position of the silane group, in particular N- (methyldimethoxysilylmethyl) -O-methylcarbamate, (methacryloxymethyl) silane, methoxymethylsilane, orthoformate, calcium oxide or molecular sieve powder.

Suitable drying agents for the isocyanate group-containing compositions are, in particular, molecular sieve powder, calcium oxide, highly reactive isocyanates, for example p-toluenesulfonylisocyanate, monomeric diisocyanates or orthoformates.

Suitable thickeners are, in particular, urea, sheet silicates such as bentonite, derivatives of castor oil, hydrogenated castor oil, polyamides, polyurethanes or fumed silica.

Preferred thickeners are pastes which are spreadable at room temperature and contain from 10% to 25% by weight of a urea compound and from 75% to 90% by weight of the abovementioned polyethers having blocked hydroxyl groups. Such pastes are obtained in particular by reacting diisocyanates, in particular 4,4' -diphenylmethane diisocyanate, and monoamines, in particular n-butylamine, in polyethers having blocked hydroxyl groups.

Suitable catalysts are catalysts for the crosslinking of silane groups, in particular metal catalysts, such as, in particular, compounds of tin, titanium, zirconium, aluminum or zinc, and/or nitrogen-containing compounds. Preference is given to diorganotin (IV) compounds, such as, in particular, dibutyltin (IV) diacetate, dibutyltin (IV) dilaurate, dibutyltin (IV) dineodecanoate, dibutyltin (IV) di (acetylacetonate) or dioctyltin (IV) dilaurate, also titanium (IV) -complexes or zirconium (IV) -complexes or aluminum (III) -complexes or zinc (II) -complexes, in particular organotitanates, in particular with alkoxy ligands, carboxylate ligands, 1, 3-diketonate ligands or 1, 3-ketoamide ligands, and also amines, amidines, such as, in particular, 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), 1, 5-diazabicyclo [4.3.0] non-5-ene (DBN), 6-dibutylamino-1, 8-diazabicyclo [5.4.0] undec-7-ene, N' -di-N-hexylacetamidine (DHA), 2-methyl-1, 4,5, 6-tetrahydropyrimidine, 1, 2-dimethyl-1, 4,5, 6-tetrahydropyrimidine, 2,5, 5-trimethyl-1, 4,5, 6-tetrahydropyrimidine, N- (3-trimethoxysilylpropyl) -4, 5-dihydroimidazole, N- (3-triethoxysilylpropyl) -4, 5-dihydroimidazole, 1- (3-dimethylaminopropyl) -2-methyl-1, 4,5, 6-tetrahydropyrimidine, 1- (3-aminopropyl) -2-methyl-1, 4,5, 6-tetrahydropyrimidine or reaction products thereof, or guanidines such as, in particular, 1-butylguanidine, 1-dimethylguanidine, 1, 3-dimethylguanidine, 1,3, 3-Tetramethylguanidine (TMG), 2- (3- (trimethoxysilyl) propyl) -1,1,3, 3-tetramethylguanidine, 2- (3- (methyldimethoxysilyl) propyl) -1,1,3, 3-tetramethylguanidine, 2- (3- (triethoxysilyl) propyl) -1,1,3, 3-tetramethylguanidine, 1,5, 7-triazabicyclo [4.4.0] dec-5-ene (TBD), 7-methyl-1, 5, 7-triazabicyclo [4.4.0] dec-5-ene, 7-cyclohexyl-1, 5, 7-triazabicyclo [4.4.0] dec-5-ene, 1-phenylguanidine, 1- (o-tolyl) guanidine (OTG), 1, 3-diphenylguanidine, 1, 3-di (o-tolyl) guanidine, 2-guanidinobenzimidazole or guanidine from the reaction of monoamines, polyamines or aminosilanes with carbodiimides, in particular dicyclohexylcarbodiimide or diisopropylcarbodiimide, and biguanides or imidazoles.

Preferred are organotitanates, especially bis (ethylacetoacetato) diisobutyloxytitanium (IV) (commercially available, for example)IBAY, from Dorf Ketal), bis (ethylacetoacetato) diisopropoxytitanium (IV) (commercially available, e.g.DC from Dorf Ketal), bis (acetylacetonate) diisopropoxytitanium (IV), bis (acetylacetonate) diisobutoxytitanium (IV), tris (oxyethyl) amine titanium Isopropoxide (IV), bis [ tris (oxyethyl) amine]Diisopropoxytitanium (IV), bis (2-ethylhexane-1, 3-dioxy) titanium (IV), tris [2- ((2-aminoethyl) amino) ethoxy]Titanium (IV) ethoxide, bis (neopentyl (diallyl) oxy) diethoxytitanium (IV), tetra (isopropoxy) titanate, tetra (n-butoxy) titanate, tetra (2-ethylhexyloxy) titanate or polybutyltitanate, especially bis (ethylacetoacetato) diisobutyloxytitanium (IV) or bis (ethylacetoacetato) diisopropoxytitanium (IV).

Further preferred are amidines or guanidines, in particular DBU, 1- (3-dimethylaminopropyl) -2-methyl-1, 4,5, 6-tetrahydropyrimidine, 1- (3-aminopropyl) -2-methyl-1, 4,5, 6-tetrahydropyrimidine or reaction products thereof, or guanidines from the reaction of a monoamine, polyamine or aminosilane with dicyclohexylcarbodiimide or diisopropylcarbodiimide.

Further preferred are combinations of these catalysts, especially combinations of at least one organic carbonate and at least one amidine or guanidine.

Suitable catalysts are also catalysts which promote the reaction of the isocyanate groups, in particular organotin (IV) compounds such as, in particular, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dichloride, dibutyltin diacetylacetonate, dimethyltin dilaurate, dioctyltin diacetate, dioctyltin dilaurate or dioctyltin diacetylacetonate, complexes of bismuth (III) or zirconium (IV), in particular complexes of bismuth (III) or zirconium (IV) with ligands selected from the group consisting of alkoxides, carboxylates, 1, 3-diketonates, quinolinolates, 1, 3-ketoesters and 1, 3-ketoamides, or compounds containing tertiary amino groups such as, in particular, 2' -dimorpholinodiethyl ether (DMDEE).

Suitable catalysts are also catalysts for the hydrolysis of latent curing agents, especially carboxylic acids such as 2-ethylhexanoic acid, lauric acid, stearic acid, neodecanoic acid, benzoic acid, salicylic acid or 2-nitrobenzoic acid, organic carboxylic anhydrides, silyl esters of carboxylic acids, organic sulfonic acids, sulfonic esters, other organic or inorganic acids, or mixtures of the above acids or esters. Preference is given to aromatic carboxylic acids, such as benzoic acid, 2-nitrobenzoic acid or, in particular, salicylic acid.

The curable composition may comprise further ingredients, in particular:

inorganic or organic pigments, especially titanium dioxide, chromium oxide or iron oxide;

-an additional plasticizer;

fibers, in particular glass fibers, carbon fibers, metal fibers, ceramic fibers, plastic fibers such as polyamide fibers or polyethylene fibers, or natural fibers such as wool, cellulose, hemp or sisal;

-nanofillers such as graphene or carbon nanotubes;

-a dye;

other catalysts which promote the reaction of the isocyanate groups and/or silane groups, in particular salts, soaps or complexes of tin (II), iron, aluminum, molybdenum dioxo or potassium, in particular aluminum lactate, aluminum oleate or potassium acetate; compounds containing tertiary amino groups, in particular N-ethyldiisopropylamine, N, N, N ', N ' -tetramethylalkylenediamine, pentamethylenetriamine and its higher homologues, bis (N, N-diethylaminoethyl) adipate, tris (3-dimethylaminopropyl) amine, 1, 4-diazabicyclo [2.2.2] octane (DABCO), N-alkylmorpholine, N, N ' -dimethylpiperazine; nitrogen-containing aromatic compounds such as 4-dimethylaminopyridine, N-methylimidazole, N-vinylimidazole or 1, 2-dimethylimidazole; organic ammonium compounds such as benzyltrimethylammonium hydroxide or alkoxylated tertiary amines; and so-called "delayed action" catalysts, which are variants of known metal or amine catalysts;

-solvents, in particular acetone, methyl acetate, tert-butyl acetate, 1-methoxy-2-propyl acetate, ethyl-3-ethoxypropionate, diisopropyl ether, diethylene glycol diethyl ether, ethylene glycol monobutyl ether, ethylene glycol mono-2-ethylhexyl ether, acetals such as, for example, propanal, butanal, 2-ethylhexanal, dioxolane, glycerol formal or 2,5,7, 10-Tetraoxaundecane (TOU), toluene, xylene, heptane, octane, naphtha, mineral spirits, petroleum ethers or gasoline, in particular Solvesso^TMType (from ExxonMobil Chemical Co.), and propylene carbonate, dimethyl carbonate, butyrolactone, N-methyl pyrrolidone, N-ethyl pyrrolidone, p-chlorotrifluoromethylene, or trifluorotoluene;

natural resins, fats or oils such as rosin, shellac, linseed oil, castor oil or soybean oil;

-a non-reactive polymer, in particular a homopolymer or copolymer of an unsaturated monomer, in particular selected from ethylene, propylene, butylene, isobutylene, isoprene, vinyl acetate or an alkyl (meth) acrylate, in particular Polyethylene (PE), polypropylene (PP), polyisobutylene, ethylene vinyl acetate-copolymer (EVA) or atactic poly-alpha-olefin (APAO);

flame-retardant substances, in particular the fillers aluminum hydroxide or magnesium hydroxide described above, and in particular organic phosphates, such as, in particular, triethyl phosphate, tricresyl phosphate, triphenyl phosphate, diphenyl cresyl phosphate, isodecyl diphenyl phosphate, tris (1, 3-dichloro-2-propyl) phosphate, tris (2-chloroethyl) phosphate, tris (2-ethylhexyl) phosphate, tris (chloroisopropyl) phosphate, tris (chloropropyl) phosphate, isopropylated triphenyl phosphate, mono-, bis-and tris (isopropylphenyl) phosphates of different degrees of isopropylation, resorcinol-bis (diphenyl phosphate), bisphenol-a-bis (diphenyl phosphate) or ammonium polyphosphate;

additives, especially wetting agents, levelling agents, defoamers, deaerators, stabilizers or biocides against oxidation, heat, light or ultraviolet radiation;

or other materials commonly used in curable compositions.

It may be desirable for certain ingredients to be chemically or physically dried before being incorporated into the composition.

The curable composition is preferably substantially free of a fatty alcohol ester-containing plasticizer. It is especially phthalate-free. It preferably contains less than 2 wt.%, more preferably less than 1 wt.%, and especially less than 0.5 wt.% of phthalate ester.

The curable composition preferably contains 10 to 40% by weight of a polyether having blocked hydroxyl groups.

A preferred curable composition comprises

10 to 50 wt% of a polymer containing isocyanate and/or silane groups,

-20 to 60% by weight of a filler and

-10 to 40 wt% of a polyether having blocked hydroxyl groups.

The curable compositions are prepared, in particular, with exclusion of moisture and are stored at ambient temperature in moisture-tight containers. Suitable moisture-tight containers consist in particular of optionally coated metal and/or plastic and are in particular drums, transport containers, pails, tubes, cans, boxes, bags, tubular bags, magazines or tubes.

The curable composition may be present in the form of a one-component composition or in the form of a multi-component (especially two-component) composition.

A composition referred to as a "one-part" composition is one in which all of the ingredients of the composition are in the same container, which is itself storage stable and curable with water.

A composition referred to as a "two-component" composition is one in which the components of the composition are in two distinct components, which are stored in separate containers and not mixed with each other until before or during administration of the composition.

The curable composition is preferably one-component and moisture-curable. If provided in suitable packaging and storage, it can be generally stable for storage for several months, up to a year or more.

In the use according to the invention, the curable composition is applied to at least one basic substrate. The substrate may be pretreated prior to application, in particular by a cleaning process or by applying an activator or primer, in which case the optionally applied activator or primer will generally not completely seal the surface of the substrate, so that it will produce an alkaline reaction, at least in certain parts, as in the prior art.

Upon application of the composition, the curing process is initiated. Thereby forming a cured composition.

In the case of one-component moisture-curing compositions, they are applied as such and then cure is started under the influence of moisture or water. To promote curing, an accelerator component containing or releasing water and/or a catalyst may be mixed into the composition at the time of application, or the composition may be contacted with such an accelerator component after application.

In the case of two-component compositions, the two components are applied after they have been mixed and curing is initiated by an internal reaction, wherein curing is optionally completed by the action of external moisture. The two components can be mixed continuously or intermittently with a dynamic mixer or a static mixer.

During the curing process, the isocyanate groups present react with one another and/or with other reactive groups optionally present in the composition, in particular hydroxyl or amino groups, under the influence of moisture. In addition, the isocyanate groups present react with the hydrolysis-reactive groups of the latent curing agent, if present. The silane groups present react with one another under the influence of moisture during the curing process. They can be hydrolyzed upon contact with moisture to give silanol groups (Si-OH groups). The silane groups present can condense with the silanol groups present to give siloxane groups (Si-O-Si groups).

The moisture required for curing of the moisture-curable composition preferably enters the composition by diffusion from the air (air moisture). In this process, a solid layer of cured composition (skin) is formed on the surface of the composition that is in contact with the air. Curing continues in the direction of diffusion from the outside inward, during which the skin becomes thicker and eventually covers the entire composition applied. Moisture may also additionally or completely enter the composition from one or more substrates to which the composition has been applied, and/or may come from an accelerator component that is mixed into the composition at the time of application or contacted therewith after application, for example by brushing or spraying.

The curable composition is preferably applied at ambient temperature, especially in the range of about-10 to 50 ℃, preferably in the range of-5 to 45 ℃, especially 0 to 40 ℃.

The composition preferably also cures at ambient temperature.

The curable composition may be formulated in such a way that it has a pasty consistency with a high flow limit, in particular for use as an adhesive or sealant. Such a composition can be applied by means of a spatula or under pressure by means of a suitable device, for example by means of a magazine gun or a roller pump or a painting robot, wherein the composition is discharged in particular in the form of a strip of glue having a substantially circular or triangular cross section. The layer thickness of the applied composition is in particular in the range from 0.5 to 50mm, preferably in the range from 1 to 30 mm.

The curable compositions can also be formulated so that they are fluid and so-called "self-leveling" or only slightly thixotropic, in particular for use as sealants or coatings. Such compositions may be applied by pouring or with a spatula. The coating can then be spread out over its surface to the desired layer thickness, for example by means of a roller, doctor blade, toothed blade or squeegee. In one operation, a layer thickness in the range from 0.5 to 5mm, in particular from 1 to 3mm, is generally applied.

The curable compositions are storage stable, easy to handle, highly elastic after curing and do not show any tendency to separate or migrate. It makes it possible to achieve elastic bonding, sealing or coating of alkaline substrates, such as in particular fresh or raw concrete or cement mortar, without the occurrence of unpleasant odours during this period caused by saponification of the plasticizer.

The invention further provides a method of bonding or sealing or coating comprising the steps of:

(i) there is provided a curable composition as described above,

(ii) providing at least one basic substrate as described above,

(iii) contacting the curable composition with a basic substrate,

(iv) curing the composition.

In the case of a two-component composition or a multi-component composition, the components are mixed prior to step (iii).

Step (iii) may be carried out by applying the curable composition to a basic substrate.

Alternatively, step (iii) may be carried out by applying the curable composition to any substrate and then contacting the applied composition with a basic substrate.

The composition may be applied between two or more substrates, or may be contacted with additional substrates after application to a first substrate. In this case, at least one substrate to which the composition is applied is contacted with an alkaline substrate as described above.

Other substrates which may be contacted with the composition are, inter alia:

glass, glass-ceramic, concrete, mortar, cement screed, fiber cement, especially fiber cement board, brick, tile, gypsum (especially gypsum board or anhydrite screed), or natural stone such as granite or marble;

repair or levelling materials based on PCC (polymer-modified cement mortar) or ECC (epoxy-modified cement mortar);

metals or alloys, such as aluminum, copper, iron, steel, non-ferrous metals, including surface-treated metals or alloys, such as galvanized or chromed metals;

-asphalt or bitumen;

leather, fabric, paper, wood material combined with a resin (for example a phenolic resin, a melamine resin or an epoxy resin), resin-fabric-composite or other so-called polymer composite;

plastics, such as rigid and flexible PVC, polycarbonate, polystyrene, polyester, polyamide, PMMA, ABS, SAN, epoxy, phenolic, PUR, POM, TPO, PE, PP, EPM or EPDM, each untreated or surface-treated, for example by means of plasma, corona or flame;

fiber-reinforced plastics, such as carbon fiber-reinforced plastics (CFK), glass fiber-reinforced plastics (GFK) and Sheet Molding Compounds (SMC);

insulating foams, in particular made of EPS, XPS, PUR, PIR, asbestos, glass wool or foamed glass (foam glass);

-a coated or painted substrate, in particular a painted tile, a coated concrete, a powder coated metal or alloy or a painted metal sheet.

If desired, the substrate can be pretreated before application, in particular by physical and/or chemical cleaning methods or by applying activators or primers.

The same or different substrates may be bonded and/or sealed.

Particularly in the case of sealants for joining, it is common to apply between a plurality of substrates, while it is common for adhesives to be applied on a first substrate and subsequently contacted with a second substrate. Here, such an adhesive may also have a sealing function.

The coating is typically applied to only one substrate, although there may be instances where the coating is in contact with other substrates (e.g., in the edge region).

The curable composition is preferably an adhesive or sealant or coating depending on its use.

The cured adhesive or sealant or cured coating is preferably elastomeric.

As adhesive, the compositions are particularly suitable for use in the construction industry for adhesive and sealing applications on alkaline substrates, in particular for splice floor adhesion on fresh cement screeds or for construction adhesion on fresh concrete.

As sealants, the compositions are particularly suitable for sealing joints, joints or cavities of alkaline substrates in construction, particularly for sealing expansion joints or connecting joints between components.

As coating materials, the compositions are particularly suitable for protecting alkaline substrates, in particular floors or walls, in particular for coatings for balconies, terraces, squares, bridges, parking lots, or for sealing roofs, in particular flat roofs or slightly inclined roof areas or roof gardens, or for water sealing inside buildings, for example under tiles or ceramic panels in toilets or kitchens, or as floor coverings in kitchens, industrial buildings or production spaces, or as sealants in catchments, channels, shafts, silos, tanks or wastewater treatment plants.

An article is obtained by means of gluing or sealing or coating.

Thus, the invention further provides articles bonded, sealed or coated with the composition.

The article is especially a building structure or a part thereof, especially a bridge, roof, staircase, floor or facade or a mounting assembly thereof, above or below ground.

Particularly preferably, the article is a splice floor bonded to a concrete or cement mortar screed, which is bonded to a still fresh and therefore alkaline screed. The use of a binder which does not release the cleavage products of strong odor in alkaline medium is particularly important here, since the binder is applied in the room over a relatively large area, whereby any odor emissions which may occur are particularly strong, lasting and annoying.

An adhesive bond is obtained by means of gluing or sealing or coating.

The invention therefore also provides an adhesive joint comprising a cured composition as described above and at least one substrate adhered to the composition, the surface of which is basic at the moment of contact with the composition, as described above.

The cured composition preferably comprises

-10% to 50% by weight of a cured polymer,

-20% to 60% by weight of a filler, and

-10% to 40% by weight of a polyether having blocked hydroxyl groups.

The layer thickness of the cured composition in the adhesive joint of the invention is preferably from 0.5 to 50mm, preferably from 1 to 30 mm.

The adhesive interface is a portion of an article that is adhered, sealed or coated with the composition.

The use according to the invention enables alkaline substrates, such as in particular fresh or raw concrete or cement mortar, to be elastically bonded, sealed or coated without the occurrence of unpleasant odours caused by saponification of the plasticiser, as is usually the case with conventional plasticisers such as DIDP or DINCH.

Examples

Working examples are given below, which are intended to clarify the described invention. Of course, the invention is not limited to these described working embodiments.

"Standard climatic conditions" ("NK") means a temperature of 23. + -. 1 ℃ and a relative air humidity of 50. + -. 5%.

Unless otherwise stated, the chemicals used were from Sigma-Aldrich Chemie GmbH.

Preparation of polyethers with blocked hydroxyl groups:

with a constant temperature cone-plate viscometer Rheotec RC30 (cone diameter 25mm, cone angle 1 °, cone tip to plate distance 0.05mm, shear rate 10s^-1) The viscosity was measured.

Infrared spectroscopy (FT-IR) was measured as an undiluted film on a Thermo Scientific FT-IR device Nicolet iS5 equipped with a horizontal ATR-measuring cell with diamond crystals. Wave number (cm) for absorption band^–1) And (4) showing.

¹H NMR spectra were measured on a Bruker Ascend 400 type spectrometer at 400.14 MHz. Chemical shifts δ are expressed in ppm relative to Tetramethylsilane (TMS). The real coupling and the pseudo coupling modes are not distinguished.

Polyether-1: acetylated PPG monols starting from n-butanol, with an average molecular weight of about 800g/mol

First 120.00g of polyoxypropylene monoalcohol starting from n-butanol under nitrogen atmosphere (100-20B, average molecular weight about 750 g/mol; from DowDuPont Inc.) and 18.74g of acetic anhydride were charged to a round bottom flask with distillation attachment. The reaction mixture was then stirred under a gentle stream of nitrogen at 130 ℃ with acetic acid collected as distillate. Subsequently, volatile constituents are removed from the reaction mixture at 80 ℃ and under reduced pressure of 10 mbar. A clear, colorless liquid is obtained, which has a viscosity of 75 mPas at20 ℃.

FT-IR:2970,2931,2867,1738,1454,1372,1345,1296,1241,1098,1014,959,925,866,827。

¹H NMR(CDCl₃):5.02(hept.,1H,CH₂(CH₃) CH-OAc), 3.75-3.34 (2xm, about 39H, OCH)₂CH(CH₃)O),3.33–3.28(m,2H,CH₃CH₂CH₂CH₂O),2.04(s,3H,O(CO)CH₃),1.55(quint.,2H,CH₃CH₂CH₂CH₂O),1.36(sext.,2H,CH₃CH₂CH₂CH₂O),1.22(d,3H,CH₂(CH₃) CH-OAc), 1.17-1.10 (m, about 36H, OCH)₂CH(CH₃)O),0.91(t,3H,CH₃CH₂CH₂CH₂O)。

Polyether-2 diacetylated PPG diol, average molecular weight about 1100g/mol

80.00g of polyoxypropylene glycol (C) (as described for polyether-1)P1010, OH value 110mg KOH/g; from Dowdepont Inc.) and 18.74g of acetic anhydride. A clear, colorless liquid is obtained, which has a viscosity of 145 mPas at20 ℃.

Polyether-3 diacetylated PPG diol having an average molecular weight of about 2100g/mol

160.00g of polyoxypropylene glycol (C) (as described for polyether-1)2000L, OH number 56mg KOH/g; from DowDuPont Inc.) and 18.74g of acetic anhydride. A clear, colorless liquid is obtained, which has a viscosity of 400 mPas at20 ℃.

Preparation of other starting materials:

polymer P1:

3080g of polyoxypropylene glycol (C)4200 from Covestro AG; OH number 28.5mg KOH/g), 1540g of polyoxypropylene polyoxyethylene triol (MD34-02 from Shell Chemicals co.; OH number 35.0mg KOH/g) and 385g of toluene diisocyanate (T80P, Covestro AG) at 80 ℃ by known methods to give an NCO-terminated polyurethane polymer which is liquid at room temperature and has a content of free isocyanate groups of 1.50% by weight.

Aldimine-1: n, N' -bis (2, 2-dimethyl-3-lauroyloxypropylidene) -3-aminomethyl-3, 5, 5-trimethylcyclohexylamine

598g (2.1mol) of 2, 2-dimethyl-3-lauroyloxypropanal were first introduced into a round-bottomed flask under a nitrogen atmosphere. 170.3g (1mol) of 3-aminomethyl-3, 5, 5-trimethylcyclohexylamine (b) are subsequently added with good stirringIPD from Evonik Industries AG) and subsequently volatile constituents were removed at 80 ℃ and a reduced pressure of 10 mbar. 732g of a colorless liquid are obtained having an amine content of 2.73mmol N/g, which corresponds to 367g/mol of calculated imide equivalents.

Thixotropic agent T-1:

first, 300g of polyether-1 and 48g of 4,4' -methylenediphenyl diisocyanate (II) are placed in a vacuum mixer44MC L from Covestro AG) and heated slightly, then 27g of n-butylamine were added slowly dropwise with vigorous stirring. The resulting paste was stirred under reduced pressure for a further 1 hour while cooling. A white, finely divided, homogeneous, spreadable paste is obtained.

Thixotropic agent T-2:

prepared as described for thixotropic agent T-1, except that 300g of polyether-2 are used instead of polyether-1. A white, finely divided, homogeneous, spreadable paste is obtained.

Thixotropic agent T-3:

prepared as described for the thixotropic agent T-1, except that 300g of diisodecyl phthalate (b)10-P from BASF SE) instead of polyether-1. A white, finely divided, homogeneous, spreadable paste is obtained.

Thixotropic agent T-4:

prepared as described for thixotropic agent T-1, except that 300g of diisononyl-1, 2-cyclohexanedicarboxylate (ester)DINCH from BASF SE) instead of polyether-1. A white, finely divided, homogeneous, spreadable paste is obtained.

Preparing a mortar prism:

1300 parts by weight (GT) of 0 to 1 mm quartz sand, 200GT of ground limestone (unfired) and 900GT of CEM I42.5N Portland water were usedAnd (5) producing dry mixed materials by mud. Separately, 400GT of water is mixed with 6.3GT of water(retarder/plasticizer; from Sika Schweiz AG) and the mixture was mixed thoroughly with the dry blend in a mechanical mixer for 3 minutes. The mortar obtained was poured into several 80x40x40mm moulds, covered with plastic film and stored under standard climatic conditions.

After 24 hours, the plastic film was removed and cured, but the still fresh mortar prism was removed from the mold, cleaned on the outside with a steel brush and dusted. The curable composition described below was immediately applied to the thus prepared fresh (green) mortar prism.

Preparation of curable (one-component) composition:

composition Z1-Z5

For each composition, the water was removed and the mixing was carried out at 3000rpm for one minute by means of a centrifugal mixer (SpeedMixer)^TMDAC 150, FlackTek Inc.) the ingredients indicated in table 1 were mixed in the amounts indicated (in parts by weight).

Each composition was tested as follows:

as a measure of open time, the skinning time (HBZ) was determined. For this purpose, a few grams of the composition are applied to a cardboard in a layer thickness of about 2mm and the time until no residue remains on the liquid tube for the first time when the surface of the composition is tapped gently with the aid of an LDPE pipette is determined under standard climatic conditions.

The Shore A hardness was determined according to DIN 53505 on specimens cured for 14 days under standard climatic conditions.

To determine the mechanical properties, the compositions were applied to a film coated with PTFE to give a film having a thickness of 2mm, the film was stored for 14 days under standard climatic conditions, and several dumbbells having a bar length of 30mm and a bar width of 4mm and a length of 75mm were punched out of the film and tested for their tensile strength (force at break), elongation at break, 5% modulus of elasticity (elongation at 0.5% to 5%) and 25% modulus of elasticity (elongation at 0.5% to 25%) at a tensile rate of 200 mm/min in accordance with DIN EN 53504.

The appearance on the prepared film was visually evaluated. "good" is used to describe a non-stick, bubble-free film.

Odor was assessed by smelling through the nose 2cm from the freshly prepared film. "none" means no odor was perceived.

The results are reported in table 1.

The composition marked (Ref.) does not contain any polyether with blocked hydroxyl groups of the present invention.

TABLE 1 compositions (in parts by weight) and properties of Z1 to Z5. "n.b." means "not detected"

¹Diisodecyl phthalate (A)10-P from BASF SE)

²Diisononyl-1, 2-cyclohexanedicarboxylate esterDINCH from BASF SE)

³ 5-GU (from Omya AG)

⁴5% by weight in di (2-ethylhexyl) adipate

Use of a curable composition on fresh mortar:

examples 1 to 5

Each of the compositions Z1 to Z5 prepared as described above was applied in a layer thickness of 2mm over an area of 30 x 80mm onto two fresh (green) mortar prisms prepared as described above. The first prism coated in this way was stored in a closed aluminum can at 80 ℃ for 24 hours in an air circulating oven and then tested for odor development. These results are marked "(1 d 80 ℃ C.)". The second coated prism was stored in a closed aluminum can for 7 days under standard climatic conditions and then likewise tested for odor development. These results were labeled "(7 d NK)". Odor formation was determined by carefully opening the aluminum can under standard climatic conditions and immediately detecting any odor by sniffing in the head space of the aluminum can and composition. No means no smell was perceived. By "mild" is meant a mild odor, as is typical of compositions that are inherently odorous in the warm state. By "apparent" is meant a clearly perceptible musty taste. "strong" means a strong musty taste.

The results are reported in table 2.

The example labeled (Ref.) is a comparative example.

TABLE 2 Properties (odor development) of compositions Z1 to Z5 on fresh (raw) mortars.