阅读说明：本技术 基于羟基化的二酰胺或三酰胺及其混合物的流变添加剂 (Rheological additive based on hydroxylated diamides or triamides and mixtures thereof ) 是由 D.科尔斯尼克 V.勒罗伊 L.莱皮奈 于 2020-03-27 设计创作，主要内容包括：本发明涉及可用作有机胶凝剂并且特别地用作流变添加剂的脂肪酰胺,其为基于聚醚二胺或三胺的二酰胺或三酰胺,所述酰胺包含羟基化脂肪酸和羟基化短链酸的特定混合物。本发明还涉及使用所述脂肪酰胺作为流变添加剂的制剂组合物并且涉及其以此为意图的在涂料组合物、胶粘剂组合物或PVC塑料溶胶组合物并且特别是透明或非透明胶泥组合物中的用途。与其它的已知的基于氢化蓖麻油衍生物的脂肪酰胺添加剂不同,所述流变添加剂具有使用前不需要特定的活化过程的优点。(The present invention relates to fatty amides useful as organogelling agents and in particular as rheological additives, which are diamides or triamides based on polyether diamines or triamines, said amides comprising a specific mixture of hydroxylated fatty acids and hydroxylated short-chain acids. The invention also relates to a formulation composition using said fatty amide as a rheological additive and to the use thereof for this purpose in coating compositions, adhesive compositions or PVC plastisol compositions and in particular transparent or non-transparent cement compositions. Unlike other known fatty amide additives based on hydrogenated castor oil derivatives, the rheological additive has the advantage that no specific activation process is required before use.)

1. A multifunctional fatty amide, characterized in that it is a di-or tri-amide or a mixture thereof, and said fatty amide is represented by:

A) according to the following formula (I):

R[(-X-R1-NHCO-R2)_n(1-y)][(-X-R1-NHCO-R2’)_ny] (I)

wherein

N is 2 or 3, preferably 3,

-R(-X-R1-)_nis primary polyamine R (-X-R1-NH)₂)_nThe primary polyamine is a primary diamine or triamine,

-wherein each primary amino group-NH₂Is an end group carried by a divalent oligomer segment R1, said divalent oligomer segment R1 being selected from alkoxylated polyesters and polyethers, preferably polyethers, and more preferably polyoxypropylene or oxypropylene/oxyethylene copolymers based on oxypropylene units,

-R: from polyol R (OH)_nOr polyamines R (NH)₂)_nOr R (NH-R3)_nPreferably a polyol R (OH)_nN-valent C of₃-C₁₀An alkylene radical having, as a main component,

-X: o, NH or NR3, preferably O,

-R2 is a hydroxylated fatty acid R2CO₂H. In particular the saturated and linear hydroxylated fatty acids R2CO₂C of H₁₂-C₅₂Preferably C₁₆-C₃₆More preferably C₁₆-C₂₄(ii) a residue of fat,

-R2' is C bearing at least one hydroxyl group, preferably at least two hydroxyl groups₂-C₁₀Preferably C₂-C₈Monocarboxylic acid R2' CO₂The residue of H is a residue of a compound of formula,

-y represents R2' CO in said diamide₂H vs. R2' CO₂H+R2CO₂Average molar fraction of the sum of H, where y varies from 0.05 to 0.50, preferably from 0.10 to 0.40, where R2CO₂H and/or R2' CO₂H may be a mixture of the respective acids,

-R3 is C₁-C₂An alkyl substituent;

or

B) In the case where the amide is a diamide, according to the following formula (II):

(R2CONH)_(1-y)-R’-O-[CH₂-CH(R4)-O]_x-CH₂-CH(R4)-(NHCOR2’)_y (II)

wherein R' is a monopropylene glycol residue without OH: -CH (CH)₃)-CH₂-

And R2 and R2' and y are as defined above in formula (I), and

x is an oxyalkylene unit-CH₂The number of-CH (R4) -O-and x may vary from 5 to 45, preferably from 5 to 40 and more preferably from 5 to 35,

r4 is H or methyl or R4 corresponds to an ethoxy/propoxy mixture in which the oxyalkylene repeating unit-CH₂-CH (R4) -O-is ethoxy when R4 is H and propoxy when R4 is methyl, and preferably R4 is methyl and the oxyalkylene units are propoxy, and

the amide has a melting point, meaning the melting temperature, in the range of 10-110 ℃, preferably 20-100 ℃ measured by DSC after two passes at 10 ℃/min.

2. The fatty amide according to claim 1, characterized in that the number average molecular weight Mn, measured as styrene equivalents by GPC in THF, of the fatty amide defined according to a) formula (I) varies as follows:

800-,

when-n is 3, 1000-.

3. The fatty amide according to claim 1 or 2, characterized in that the oligomer segment R1 of the fatty amide according to a) formula (I) is a polyether segment.

4. Fatty acid amide according to one of claims 1 to 3, characterized in that the oligomer segment R1 is a polyoxypropylene segment.

5. The fatty amide according to one of claims 1 to 4, characterized in that the number average molecular weight Mn of the oligomer segment R1 is in the range 400-2000, preferably 500-1500.

6. The fatty amide according to one of claims 1 to 5,characterized in that the hydroxylated fatty acid R2CO₂H is selected from: 12-hydroxystearic acid (12-HSA); 9-or 10-hydroxystearic acid (9-HSA or 10-HSA), preferably a mixture of 9-and 10-hydroxystearic acid; 14-hydroxyeicosanoic acid (14-HEA); and mixtures thereof.

7. The fatty amide according to one of claims 1 to 6, characterized in that the hydroxylated fatty acid R2CO₂H is 12-hydroxystearic acid.

8. The fatty amide according to one of claims 1 to 7, characterized in that the monocarboxylic acid R2' CO₂H is selected from: 2, 2-bis (hydroxymethyl) propionic acid, 2, 2-bis (hydroxymethyl) butyric acid, glycolic acid (or glycolic acid), 2-hydroxypropionic acid (lactic acid), 2-hydroxy-3- (3-pyridyl) propionic acid, 3-hydroxybutyric acid, 2-methyl-2-hydroxybutyric acid, 2-ethyl-2-hydroxybutyric acid, hydroxypentanoic acid, hydroxycaproic acid, hydroxyheptanoic acid, hydroxyoctanoic acid, hydroxynonanoic acid, hydroxydecanoic acid and mixtures thereof; preferably, 2, 2-bis (hydroxymethyl) propionic acid, 2, 2-bis (hydroxymethyl) butyric acid, glycolic acid (or glycolic acid), 2-hydroxypropionic acid (lactic acid), 2-hydroxy-3- (3-pyridyl) propionic acid, 3-hydroxybutyric acid, 2-methyl-2-hydroxybutyric acid, 2-ethyl-2-hydroxybutyric acid, hydroxypentanoic acid, hydroxycaproic acid, hydroxyheptanoic acid, hydroxyoctanoic acid, and mixtures thereof.

9. The fatty amide according to one of claims 1 to 8, characterized in that the amide is a diamide according to A) or B) or a triamide according to A), wherein y/(1-y) varies from 1/20 to 1/2, and preferably from 1/10 to 4/10.

10. The fatty amide according to one of claims 1 to 8, characterized in that the amide is a diamide according to A) or B), wherein y/(1-y) ranges from 1/10 to 1/2, preferably from 1/10 to 4/10.

11. The fatty amide according to one of claims 1 to 8, characterized in that it is a fatty amideIs a triamide according to A), wherein the two R2 residues are derived from a hydroxylated fatty acid R2CO₂H and 1 from the acid R2' CO₂H。

12. The fatty amide according to one of claims 1 to 8, characterized in that it is a diamide according to option A) of formula (I).

13. Fatty amide according to one of claims 1 and 6 to 8, characterized in that it is a diamide according to option B) of formula (II).

14. Formulation composition of an organic binder, characterized in that it comprises:

a) at least one organic binder,

b) at least one fatty amide as defined in one of claims 1 to 13, in particular as a rheological additive.

15. The composition of claim 14, wherein the binder a) is selected from the group consisting of: polysiloxane resins terminated with blocked silane groups, polyether resins terminated with blocked silane groups, polythioether resins terminated with blocked silane groups, polyurethane prepolymer resins terminated with isocyanate groups, PVC resins for plastisols, epoxy-bearing epoxy resins.

16. The composition according to claim 14 or 15, characterized in that it comprises, in addition to a) and b) and depending on the binder, a plasticizer or a reactive diluent defined as follows:

c) plasticizers for PVC resins of silicone resins, polyurethane prepolymer resins, and plastisols, or

d) A reactive diluent for epoxy resins derived from an epoxidized monomer, and optionally

e) Hardeners for epoxy or polyurethane resins for two-component systems.

17. The composition according to claim 16, wherein the organic binder a) is a PVC resin of polysiloxane resin, polyurethane prepolymer resin or plastisol, and the plasticizer is selected from the group consisting of: phthalates, adipates, trimellitates, sebacates, benzoates, citrates, phosphates, epoxides, polyesters, alkyl sulfonates, and phthalate substitutes other than phthalates.

18. The composition of claim 17, which is a clear or non-clear cement formulation composition.

19. Use of at least one fatty amide as defined in one of claims 1 to 13, characterized in that said amide is used as a rheological additive.

20. Use according to claim 19, wherein the rheological additive is a thixotropic agent.

21. Use according to claim 19 or 20, for use in coatings, adhesives, PVC plastisols or cement compositions, preferably PVC plastisol compositions and cement compositions.

22. Use according to claim 21, characterized in that it relates to the use in a cement composition which is crosslinkable by moisture, based on a polysiloxane resin terminated by blocked silane groups, a polyether resin terminated by blocked silane groups, a polythioether resin terminated by blocked silane groups or a polyurethane prepolymer resin terminated by isocyanate groups, in particular silanes blocked by alkoxy groups.

23. Use according to claim 22, characterized in that it relates to the use in a mastic composition which is capable of being crosslinked by moisture, the mastic being transparent or not.

24. Coating, adhesive or mastic sealant, in particular a PVC plastisol coating, characterized in that it is obtained by using at least one fatty amide as defined in one of claims 1 to 13 as a rheological additive, in particular as a thixotropic agent.

Technical Field

The present invention relates to specific multifunctional amides (di-and triamides) suitable for use as organogelling agents, in particular as rheological additives and more particularly in coating compositions.

Background

EP 1514912 describes branched triamides of non-hydroxylated fatty acids based on polyetheramines and used as phase change vectoring agents in phase change inks (referred to as "hot melt inks") which have the following functions: causing the ink to transition from a solid state at ambient temperature to a liquid state at elevated temperature in the inkjet printer and causing the liquid ink droplets to solidify quickly after they have been ejected at that temperature. EP 1514912 does not suggest at least the use of these polyamides as organogelator agents or thixotropic agents and does not suggest at least hydroxylated polyamides based on mixtures of hydroxylated fatty acids and shorter chain hydroxylated monocarboxylic acids.

Fatty diamides based on aliphatic diamines (without polyether segments) and on hydroxylated fatty acids are referred to as organogelator agents and in particular as thixotropic agents.

WO 2014/053774 describes hydroxylated fatty acid diamides as organogelator agents or also referred to as rheological additives, in particular in coating, moulding, masticating or sealing agents or cosmetic compositions.

WO 2015/011375 describes fatty acid diamines comprising in their structure cycloaliphatic and aliphatic diamines in a specific molar ratio and the use of these products as organogelator agents or as rheological additives, in particular in coating, moulding, masticating or sealing agents or cosmetic compositions.

FR 2993885 describes fatty acid diamides comprising in their structure specific hydroxylated carboxylic acids and the use of this product as organogelator in coating, moulding, masticating or sealing agent compositions.

To provide the desired rheological properties, these known diamides need to be micronized beforehand to a powder state and then "activated". Depending on the product, the activation process requires high shear and sometimes heating in the range up to 100 ℃. Further, depending on the temperature conditions and polarity of the system, a minimum time period is required. Furthermore, these additives may be less compatible with some binders of the reactive formulation or with some diluents or plasticizers used for activation. This activation stage therefore constitutes a drawback specific to polyamide powders and hydrogenated castor oil derivatives used as additives in this field.

Therefore, there is a need for novel fatty polyamides which make it possible: simpler and easier shaping (into the form of fragments which are readily soluble in the plasticizer or binder of the reactive formulation of the final application without prior pre-activation), and a wider range of compatibility with the reactive binders and plasticizers/diluents used in the reactive formulation, such as silane-terminated polyethers, silane-terminated polyurethanes, polyurethanes terminated with isocyanates, silicones, polysulfides, epoxies, etc. The polyamides (meaning multifunctional amides rather than polymers) required as rheological additives must produce end products, in particular coatings, mastic sealants or sealant sealants, with improved aesthetics and surface appearance and which are transparent without surface defects, which are linked to the specific structure and specific composition of these target polyamides.

The present invention makes it possible to satisfy the new requirements defined above by means of novel fatty polyamides (polyfunctional fatty amides, in particular di-and triamides) based on primary polyamines (diamines and triamines) comprising at least one polyether segment in their structure, and in particular based on polyoxypropylenes and on fatty acids comprising at least one hydroxylated fatty acid in the presence of: shorter chain hydroxylated acids.

The first subject of the invention therefore relates to polyfunctional fatty amides based on polyether polyamines (diamines or triamines) and at least one saturated linear fatty acid bearing a non-terminal hydroxyl group in the presence of: other shorter ones with hydroxyl groupsC of (A)₂-C₁₀A monocarboxylic acid.

A second subject of the invention relates to a formulation composition of organic binders comprising at least one organic binder and at least one fatty amide as defined according to the invention, in particular as a rheological additive.

The invention also covers the use of at least one fatty amide as defined according to the invention as a rheological additive.

Finally, the invention also covers the final products obtained by using at least one fatty amide as defined according to the invention as a rheological additive, in particular as a thixotropic agent.

Thus, a first subject of the present invention is a multifunctional fatty amide, which is a di-or triamide or a mixture thereof, said fatty amide being represented by:

A) according to the following formula (I):

R[(-X-R1-NHCO-R2)_n(1-y)][(-X-R1-NHCO-R2’)_ny] (I)

wherein

N is 2 or 3, preferably 3,

-R(-X-R1-)_nis primary polyamine R (-X-R1-NH)₂)_nThe primary polyamine is a primary diamine or triamine, wherein each primary amine group-NH₂Is an end group carried by a divalent oligomer segment R1, said divalent oligomer segment R1 being selected from polyethers and alkoxylated polyesters (alkoxylated polyesters), preferably polyethers and more preferably polyoxypropylene or oxypropylene/oxyethylene copolymers based on oxypropylene units,

-R: from polyol R (OH)_nOr polyamines R (NH)₂)_nOr R (NH-R3)_nPreferably a polyol R (OH)_nN is a valence of C₃-C₁₀An alkylene radical having, as a main component,

-X: o, NH or NR3, preferably O,

-R2 is a hydroxylated fatty acid R2CO₂H. In particular saturated and linear hydroxylated fatty acids R2CO₂C of H₁₂-C₅₂Preferably C₁₆-C₃₆More preferably C₁₆-C₂₄Of a fatty residue free of carboxyl groups of (a),

-R2' is C₂-C₁₀Preferably C₂-C₈More preferably C₂-C₆With at least one hydroxyl group, preferably at least two hydroxyl groups, of monocarboxylic acids R2' CO₂The residue of H is a residue of a compound of formula,

wherein y represents R2' CO in the diamide₂H relative to R2CO₂H+R2’CO₂The molar fraction of the sum of H (R2 '/(R2 + R2')), wherein y varies from 0.05 to 0.50, preferably from 0.10 to 0.40, wherein R2CO₂H and/or R2' CO₂H may be a mixture of the respective acids,

-R3 is C₁-C₂An alkyl substituent group, a carboxyl substituent group,

or (said fatty amide is represented by) the following:

B) according to the following formula (II) in the case where the amide is a diamide:

(R2CONH)_(1-y)-R’-O-[CH₂-CH(R4)-O]_x-CH₂-CH(R4)-(NHCOR’2)_y(II)

wherein R' is a monopropylene glycol residue without OH: -CH (CH)₃)-CH₂-, and

x is an oxyalkylene unit-CH₂The number of-CH (R4) -O-and x may vary from 5 to 45, preferably from 5 to 40 and more preferably from 5 to 35.

R2 and R' 2 and "y" are as defined above for formula (I), and R4 is H or methyl or R4 corresponds to an ethoxy/propoxy mixture in which the oxyalkylene repeat units-CH₂-CH (R4) -O-is ethoxy when R4 is H and propoxy when R4 is methyl, and preferably, R4 is methyl, wherein the oxyalkylene units are propoxy, and

the amide has a melting point, meaning the melting temperature, measured by DSC after two passes at 10 ℃/min, ranging from 10 to 110 ℃, preferably from 20 to 100 ℃.

The term "melting point" corresponds to the melting temperature measured by Differential Scanning Calorimetry (DSC) at a heating rate of 10 ℃/minute. This temperature corresponds to the temperature of the melting peak recorded by DSC at the specified heating rate.

For residue R, the C₃-C₁₀Alkylene groups, in addition to carbon-carbon bonds, may also contain an ether bridge-O-in the case of a polyol residue or-NH-in the case of a polyamine residue.

In the case of X: N, as is clear from the formulae specified above for the polyamines containing R residues, this means that N represents-NH-and-N (R3) -.

For R2CO₂H, which is related to linear hydroxylated fatty acids with non-terminal hydroxyl groups. These linear fatty acids contain linear C₁₂-C₅₂Preferably C₁₆-C₃₆More preferably C₁₆-C₂₄In particular consisting only of C-C bonds and therefore having no ester groups within this linear chain. Thus, this definition is given from R2CO₂Any polyester or oligoester obtained from the self-polycondensation of hydroxylated fatty acids is excluded from the definition of H.

In the monocarboxylic acid R2' CO₂In the case of H, the term "C₂-C₁₀Preferably C₂-C₈More preferably C₂-C₆By "is meant that this is the chain length of R2' expressed as the number of carbon atoms in the chain (-C-C-) regardless of the substituent at the side position.

According to a particular choice, the acid R2CO₂H is a mixture of hydroxylated fatty acids and/or the acid R2' CO₂H is a mixture of shorter chain (compared to the hydroxylated fatty acid) hydroxylated monocarboxylic acids as defined according to the invention.

As defined above as primary diamines or triamines corresponding to the formula R (-X-R1-NH)₂)_nSuitable examples of primary polyamines of (a) may be mentioned the following:

as diamine (n ═ 2) or triamine (n ═ 3): the primary diamines having two primary amine functions carried by polyether segments or alkoxylated polyester (polyester-polyether) segments, or triamines having 3 primary amine functions carried by 3 polyether or alkoxylated polyester (polyester-polyether) segments, the combination of said polyether or alkoxylated polyester segments for diamines or, in the case of triamines, 3 polyether or alkoxylated polyester segments, have a number average molecular weight Mn in the range of 500-3000.In particular, they are primary diamine and triamine polyethers, and more particularly primary diamine and triamine polyoxypropylenes, such as those sold by HuntsmanDiamines and triamines, of which more specific examples areD-2000 (a primary diamine having a polyoxypropylene segment having 2 primary amine groups, wherein the number of oxypropylene units is 33) orT-3000 (a primary triamine having 3 polyoxypropylene segments and a total number of oxypropylene units of 50). Other amines may also be used:D-400，D-2010，T-403，t-5000, and the like.

In principle, the polyether diamines or polyether triamines suitable for preparing the diamides and triamides according to the invention can be obtained from the corresponding polyether polyol (diol or triol, respectively) precursors by reductive amination of the terminal OH functions in the presence of a catalyst, as described in US 4766245 or GB 2175910.

Polyether polyol (diol or triol) precursors for polyether diamines or triamines, respectively, can be obtained by anionic polymerization of the corresponding alkylene oxides (ethylene oxide for polyoxyethylene diols/triols, propylene oxide for polyoxypropylene diols/triols) or mixtures of said alkylene oxides in the presence of polyol alkoxylate (alcoholate, alkoxylate, alkoxide) initiators having primary OH groups, which are diols or triols (having primary OH groups), respectively, or polyamine initiators, which are diamines and triamines, respectively (depending on the functionality of the polyether: diols or triols), in an alkaline medium. As examples of diol initiators, mention may be made of ethylene glycol, diethylene glycol, 1, 3-propanediol, 1, 4-butanediol. As an example of a triol initiator, trimethylolpropane may be mentioned.

In the case of divalent initiators (two primary alkoxide functions or two amine functions), this results in a symmetrical structure in which the initiator is introduced (via an ether-O-or-NH-bond) in the middle of the chain and the polyether chain is opened by the respective alkoxide or amine function of the initiator used.

In the case of trivalent initiators (primary alkoxide triols or triamines), each alkoxide or amine is the opening point of a polyether chain, with the result that the initiator molecule carries 3 polyether chains, the residue of which corresponds to R in the formula defined above for the amides according to the invention.

In the specific case of polyether diamines, the polyether diol precursors are also obtainable by anionic polymerization of alkylene oxides or corresponding mixtures of alkylene oxides, for example ethylene oxide, or propylene oxide, or mixtures of ethylene oxide and propylene oxide for polyoxyethylene diols, polyoxypropylene diols and (oxyethylene-oxypropylene) diol copolymers, respectively, by monovalent primary alkoxide initiators bearing an OH on a secondary carbon of the initiator which does not react to open the alkylene oxide ring. In such cases, the polyether single chains are formed from primary alkoxides, the other (secondary) OH moieties of the initiator remain free and unchanged and are thus diols in the case of forming polyethers (polyether diamine precursors converted to NH2 via terminal OH groups, as mentioned above). An example of a monovalent diol initiator (1 mono-primary OH) is monopropylene glycol in the form of a primary alkoxide as follows:

HO-CH(CH₃)-CH₂O-

in the more specific case of polyoxypropylene-based polyether diamines, monopropylene glycol acts as a monovalent initiator, with secondary hydroxyl groups in the ringPolymerization of propylene oxide by the carbon atom (-CH) which is the least electron rich of propylene oxide by the anionic alkoxide initiator₂-) and subsequent chain growth, resulting in polyoxypropylene diols with two secondary OH groups of the formula:

HO-CH(CH₃)-CH₂-O-(CH₂-CH(CH₃)-O)_x-CH₂-CH(CH₃)-OH

conversion of a terminal secondary hydroxyl group (by reaction at NH)₃Catalytic reductive amination under pressure, as described in US 4766245 or GB 2175910), polyoxypropylenediamine of the formula can be obtained:

H₂N-CH(CH₃)-CH₂O-(CH₂-CH(CH₃)-O)_x-CH₂-CH(CH₃)-NH₂

as examples of such polyoxypropylene diamines, mention may be made of those sold by HuntsmanD2000。

As hydroxylated saturated linear fatty acids R2CO as defined according to the invention₂H (wherein R2 bears a non-terminal OH) may use a hydroxy fatty acid selected from: 12-hydroxystearic acid (12-HSA), 9-hydroxystearic acid (9-HSA), 10-hydroxystearic acid (10-HSA), 14-hydroxyeicosanoic acid (14-HEA), or mixtures thereof.

As shorter C₂-C₁₀The acid R2' CO2H, 2, 2-bis (hydroxymethyl) propionic acid, 2, 2-bis (hydroxymethyl) butyric acid, glycolic acid (or glycolic acid), 2-hydroxypropionic acid (lactic acid), 2-hydroxy-3- (3-pyridyl) propionic acid, 3-hydroxybutyric acid, 2-methyl-2-hydroxybutyric acid, 2-ethyl-2-hydroxybutyric acid, hydroxypentanoic acid, hydroxycaproic acid, hydroxyheptanoic acid, hydroxyoctanoic acid, hydroxynonanoic acid, hydroxydecanoic acid and mixtures thereof may be used; preferably 2, 2-bis (hydroxymethyl) propionic acid, 2, 2-bis (hydroxymethyl) butyric acid, glycolic acid (or glycolic acid), 2-hydroxypropionic acid (lactic acid), 2-hydroxy-3- (3-pyridyl) propionic acid, 3-hydroxybutyric acid, 2-methyl-2-hydroxybutyric acid, 2-ethyl-2-hydroxybutyric acid, hydroxybutanoic acidValeric acid, hydroxycaproic acid, hydroxyheptanoic acid, hydroxyoctanoic acid and mixtures thereof; more preferably 2, 2-bis (hydroxymethyl) propionic acid, 2, 2-bis (hydroxymethyl) butyric acid, glycolic acid (or glycolic acid), 2-hydroxypropionic acid (lactic acid), 2-hydroxy-3- (3-pyridyl) propionic acid, 3-hydroxybutyric acid, 2-methyl-2-hydroxybutyric acid, 2-ethyl-2-hydroxybutyric acid, hydroxypentanoic acid, hydroxycaproic acid, and mixtures thereof.

The fatty amides according to the invention represented by a according to formula (I) preferably have a number average molecular weight Mn as measured by GPC as styrene equivalents in THF (calibrated by polystyrene standards) varying as follows:

800-,

1000-6000, preferably 2000-5500 when-n-3 (triamide).

The fatty amides according to the invention represented by B according to formula (II) as fatty diamides preferably have a number average molecular weight Mn, measured as styrene equivalents by GPC in THF (calibrated by polystyrene standards), in the same range as the diamides (n ═ 2) represented by option a) according to formula (I), that is to say: 800-.

According to a preferred option of fatty amides represented by option a) according to formula (I), the oligomer segment R1 is a polyether segment.

According to a more particularly preferred option, the oligomer segment R1 is a polyoxypropylene segment.

The oligomer segment R1 may have a number average molecular weight Mn in the range 400-2000, preferably 500-1500.

According to a particular option of the invention, the fatty amide is a fatty diamide as defined above represented by option B) according to formula (II).

According to a preferred option, the hydroxylated fatty acid R2CO₂H is selected from 12-hydroxystearic acid (12-HSA); 9-or 10-hydroxystearic acid (9-HSA or 10-HSA), preferably a mixture of 9-and 10-hydroxystearic acid; 14-hydroxyeicosanoic acid (14-HEA), and paired mixtures thereof. Most preferred hydroxylated acids R2CO₂H is 12-hydroxystearic acid.

More particularly preferably, the monocarboxylic acid R2' CO₂H is selected from: 2, 2-bis (hydroxymethyl) propionic acid, 2, 2-bis (hydroxymethyl) butyric acid, glycolic acid (or glycolic acid), 2-hydroxypropionic acid (lactic acid), 2-hydroxy-3- (3-pyridyl) propionic acid, 3-hydroxybutyric acid, 2-methyl-2-hydroxybutyric acid, and 2-ethyl-2-hydroxybutyric acid.

According to another particular option of the invention, the amide is a diamide according to A) or B) or a triamide according to A), wherein the ratio "y/(1-y)" varies from 1/20 to 1/2 and preferably from 1/10 to 4/10.

According to another alternative, the amide is a diamide according to A) or B), wherein the ratio y/(1-y) varies from 1/10 to 1/2, and preferably from 1/10 to 4/10.

According to one particular option, the amide is a triamide according to A), wherein two residues (R2) are derived from a hydroxylated fatty acid R2CO₂H and one (R2 ') is derived from the acid R2' CO₂H。

More particularly and as an alternative, the amide is a diamide represented according to option a) and represented by formula (I) or according to option B) and represented by formula (II) as defined above.

A second subject of the invention relates to a formulation composition of organic binders, characterized in that it comprises: a) at least one organic binder, and

b) at least one fatty amide as defined above according to the invention, in particular as a rheological additive.

More particularly, in the adhesive formulation composition, the adhesive a) is selected from: polysiloxane resins terminated with blocked silane groups, polyether resins terminated with blocked silane groups, polythioether resins terminated with blocked silane groups, polyurethane prepolymer resins terminated with isocyanate groups, PVC resins for plastisols, epoxy resins with epoxy groups.

In addition to a) and b) and depending on the binder, the composition may comprise a plasticizer or reactive diluent as defined below:

c) plasticizers for PVC resins of silicone resins, polyurethane prepolymer resins and plastisols, or

d) A reactive diluent for epoxy resins derived from an epoxidized monomer, and optionally

e) For two-component systems, hardeners for epoxy resins or polyurethane resins.

More particularly, in the composition according to the invention, the fatty amide is used as a rheological additive, which is a thixotropic agent.

In the composition, the organic binder a) may be selected from a polysiloxane resin, a polyurethane prepolymer resin, or a PVC resin of plastisol, and the plasticizer may be selected from: phthalate esters, adipate esters, trimellitate esters, sebacate esters, benzoate esters, citrate esters, phosphate esters, epoxides, polyesters, alkyl sulfonate esters and non-phthalate ester substitutes for phthalate esters.

According to a particular option, the composition is a clear or non-clear cement formulation composition. According to a more specific option, it is a clear cement formulation composition.

Another subject of the invention covers the use according to the invention of at least one fatty amide as defined above, wherein said amide is used as a rheological additive.

In such applications, the rheological additive may be used as a thixotropic agent.

More particularly, the use may be in coatings, adhesives, PVC plastisol or cement compositions, preferably PVC plastisol compositions and cement compositions.

Another particular use is in PVC plastisol compositions.

Another particular use is in cement compositions which can be crosslinked by moisture, based on polysiloxane resins terminated by blocked silane groups, polyether resins terminated by blocked silane groups, polythioether resins terminated by blocked silane groups or polyurethane prepolymer resins terminated by isocyanate groups, in particular silanes blocked by alkoxy groups.

Another particular use is in a cement composition which is crosslinkable by moisture, the cement being transparent or opaque.

Finally, the invention covers the end products, which may be coatings (in particular PVC plastisol coatings) or adhesive or mastic sealants, obtained by using at least one fatty amide as defined above according to the invention as rheological additive, in particular as thixotropic agent.

The following examples of the following experimental section are presented by way of illustration of the invention and its performance qualities and are not intended to limit the scope thereof in any way.

Experimental part

1)Starting materials and codes used

See Table 1 below

Tables summarize starting materials used in the Synthesis of neutralizing formulations

[ Table 1]

For clarity, the following abbreviations will be used:

12 HSA: 12-Hydroxystearic acid

SA: stearic acid

HMDA: hexamethylene diamine

·D2000：D-2000 polyetheramines

·T3000：T-3000 polyetheramines

bMBA: 2, 2-bis (hydroxymethyl) butanoic acid

2) Examples of the embodiments

Example A-T3000- (12HSA-bMBA) according to the invention₃

231.40g ofT-3000(0.078mol, 1 equivalent), 63.11g of 12-hydroxystearic acid (0.199mol, 2.55 equivalents) and 5.2g of 2, 2-bis (hydroxymethyl) butyric acid (0.035mol, 0.45 equivalents) were added to a1 liter round bottom flask equipped with a thermometer, Dean-Stark apparatus, condenser and stirrer. The mixture was heated to 180 ℃ under an inert atmosphere. The water removed from 150 ℃ was collected in a Dean-Stark apparatus. The reaction was monitored by acid and amine number. When the acid value and the amine value were less than 6, respectively, the reaction was stopped. The reaction mixture was cooled to 140 ℃ and discharged into a silicone mold. Once cooled to ambient temperature, the product was converted into chips.