阅读说明：本技术 组合物、其制备方法及由其所制备的材料 (Compositions, methods of making the same, and materials made therefrom ) 是由 林其瑞 郭信良 黄淑娟 于 2021-01-15 设计创作，主要内容包括：本揭露提供一种组合物、其制备方法及由其所制备的材料。该组合物包含50-99重量份的聚醚多元醇,以及1-50重量份的具有式(I)所式结构的化合物其中,R～(1)是独立为C-(1-6)烷撑基；R～(2)是R～(3)是C-(1-6)烷撑基；i≥1；j≥0；k＝0、1、或2；当k是1或2时,R～(4)是C-(1-24)烷基；或当k是0时,R～(4)是C-(6-24)烷基；以及,B是独立为或其中,该聚醚多元醇的重量平均分子量(Mw)介于200至10000之间。(The present disclosure provides a composition, a method of making the same, and a material made therefrom. The composition comprises 50-99 parts by weight of polyether polyol and 1-50 parts by weight of compound with a structure shown in a formula (I) Wherein R is 1 Is independently C 1‑6 An alkylene group; r 2 Is that R 3 Is C 1‑6 An alkylene group; i is more than or equal to 1; j is more than or equal to 0; k is 0, 1, or 2; when k is 1 or 2, R 4 Is C 1‑24 An alkyl group; or when k is 0, R 4 Is C 6‑24 An alkyl group; and B is independently Or)

1. A composition, comprising:

50-99 parts by weight of a polyether polyol, wherein the polyether polyol has a weight average molecular weight (Mw) between 200 and 10000; and

1-50 parts by weight of at least one compound with a structure shown in formula (I)

Wherein R is¹Is independently C_1-6An alkylene group; r²Is thatR³Is C_1-6An alkylene group; i is more than or equal to 1; j is more than or equal to 0; k is 0, 1, or 2; when k is 1 or 2, R⁴Is C_1-24An alkyl group; or when k is 0, R⁴Is C_6-24An alkyl group; and B is independently

2. The composition of claim 1, wherein the polyether polyol has the structure of formula (II)Wherein R is⁵Independently is C_1-6An alkylene group; n is>1。

3. The composition of claim 1, wherein R¹And R³Is independently a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, or an isomer thereof.

4. The composition of claim 1, wherein R²Is the dehydroxylated residue of a unitary alcohol, wherein the unitary alcohol is 1-hexanol, 1-heptanol, 1-octanol, isooctanol, 1-nonanol, isononanol, 1-decanol, 1-undecanol, lauryl alcohol, 1-tridecanol, isotridecyl alcohol, 1-tetradecanol, 1-pentadecanol, 1-hexadecanol, 1-n-heptadecanol, 1-octadecanol, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether, or ethylene glycol butyl ether.

5. The composition of claim 1, wherein B is the residue of a diisocyanate compound de-isocyanate, wherein the diisocyanate compound is 2,4-toluene diisocyanate, 2,5-toluene diisocyanate, 2,6-toluene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, or 4,4' -methylene diphenyl diisocyanate.

6. According to the claimsThe composition of claim 1, wherein R is when k is 1 or 2⁴Is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, or isomers thereof; or when k is 0, R⁴Is hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, or isomers thereof.

7. The composition of claim 1, wherein the sum of the weight of the polyether polyol and the compound having the structure represented by formula (I) is 100 parts by weight.

8. The composition of claim 1, wherein the compound has the structure of formula (I)The weight average molecular weight (Mw) of the group is between 200 and 10000.

9. The composition of claim 1, wherein i is an integer from 4 to 226.

10. The composition of claim 1, wherein j is 0, or an integer from 1 to 30.

11. The composition of claim 1, further comprising: a diisocyanate compound.

12. The composition of claim 11, wherein the diisocyanate compound is 2,4-toluene diisocyanate, 2,5-toluene diisocyanate, 2,6-toluene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, 4' -methylene diphenyl diisocyanate, lysine diisocyanate, or a combination thereof.

13. The composition of claim 7, further comprising:

0.1 to 30 parts by weight of an additive, wherein the additive is an organometallic catalyst, an amine catalyst, a crosslinking agent, a blowing agent, a foam stabilizer, a plasticizer, a melt strength enhancer, an antioxidant, an anti-tack agent, an antistatic agent, a flame retardant, water, or a combination thereof.

14. A method of preparing a composition comprising:

providing 1-50 parts by weight of an organic filler, wherein the organic filler is an isocyanate derivative obtained by carrying out alcoholysis reaction on polyurethane by using a unit alcohol;

providing 50-99 parts by weight of polyether polyol, wherein the sum of the weight of the organic filler and the polyether polyol is 100 parts by weight;

providing a diisocyanate compound, wherein the molar ratio of the diisocyanate compound to the polyether polyol is 1:1 to 2.2: 1; and

mixing the organic filler, the polyether polyol, and the diisocyanate compound to obtain the composition.

15. The method for preparing a composition according to claim 14, wherein the organic filler has a structure represented by formula (I)

Wherein R is¹Is independently C_1-6An alkylene group; r²Is thatR³Is C_1-6An alkylene group; i is more than or equal to 1; j is more than or equal to 0; k is 0, 1, or 2; when k is 1 or 2, R⁴Is C_1-24An alkyl group; or when k is 0, R⁴Is C_6-24An alkyl group; and B is independently

16. The method of claim 14, wherein the polyether polyol is formed by alcoholysis of the polyurethane.

17. The method of preparing a composition according to claim 14, wherein the polyether polyol has a weight average molecular weight (Mw) of between 200 and 10000 and is polyethylene glycol, polypropylene glycol, polybutylene glycol, propylene oxide-ethylene oxide copolymer, glycerin-propylene oxide-ethylene oxide copolymer, trimethylolpropane-propylene oxide-ethylene oxide copolymer, ethylene glycol-propylene oxide-ethylene oxide copolymer, propylene glycol-propylene oxide-ethylene oxide copolymer, or polytetrahydrofuran.

18. The method of producing a composition according to claim 14, wherein the unit alcohol is 1-hexanol, 1-heptanol, 1-octanol, isooctanol, 1-nonanol, isononanol, 1-decanol, 1-undecanol, lauryl alcohol, 1-tridecanol, isotridecanol, 1-tetradecanol, 1-pentadecanol, 1-hexadecanol, 1-n-heptadecanol, 1-octadecanol, diethylene glycol methyl ether, diethylene glycol ethyl ether, diethylene glycol butyl ether, or ethylene glycol butyl ether.

19. A material prepared from the composition of any one of claims 1-13.

Technical Field

The present disclosure relates to a composition, a method of making the same, and a material made therefrom.

Background

Polyurethane products (e.g., flexible and rigid polymer foams, coatings, sealants, or adhesives) are widely used in a variety of articles and parts, from automotive parts to electronic devices. To solve the waste disposal problem of polyurethane products, the industry has studied how to recover valuable resources from polyurethane waste.

The chemical recovery technology of polyurethane is mainly an alcoholysis method, which uses a catalyst to accelerate the transesterification reaction of polyol and urethane (urethane) bond, and converts polyurethane into polyether polyol and aromatic dicarbamate polyol as by-products. Single-phase alcoholysis processes use a polyol (e.g., dipropylene glycol) with a polarity similar to the original polyether polyol as the alcoholysis agent, and the polyurethane is homogeneous after alcoholysis. However, the isocyanate-derived polyol has a benzene ring structure, a small molecular weight, and a high hydroxyl value, and cannot be used for soft foam foaming. The phase separation (Split-phase) alcoholysis method uses polyol with high polarity as alcoholysis agent (such as diethylene glycol and glycerol), and the upper layer is mainly polyether polyol and polyol alcoholysis agent. However, in addition to purification to remove the alcoholysis agent, phase separation (Split-phase) alcoholysis also produces significant amounts of isocyanate-derived polyol by-product.

Therefore, there is still a need for a new recycling process to solve the problems encountered in the prior art.

Disclosure of Invention

It is an object of the present invention to provide a composition comprising an isocyanate derivative having no reactive hydroxyl groups and a polyether polyol, thereby not affecting the subsequent reaction of the polyether polyol, which is suitable for polyurethane foam foaming and is more suitable for mass production and economic benefit than the conventional polyurethane depolymerization reaction using a diol (or polyol) as an alcoholysis agent (i.e., producing an isocyanate derivative having a terminal hydroxyl group).

Another object of the present invention is to provide a process for the preparation of the composition.

It is a further object of the present invention to provide materials prepared from the compositions.

According to the disclosed embodiment, the composition comprises 50-99 parts by weight of polyether polyol and 1-50 parts by weight of at least one compound having a structure shown in formula (I)

Wherein R is¹Is independently C_1-6An alkylene group; r²Is thatR³Is C_1-6An alkylene group; i is more than or equal to 1; j is more than or equal to 0; k is 0, 1, or 2; when k is 1 or 2, R⁴Is C_1-24An alkyl group; or when k is 0, R⁴Is C_6-24An alkyl group; and B is independently OrWherein the polyether polyol has a weight average molecular weight (Mw) of between 200 and 10000.

According to the disclosed embodiment, the polyether polyol has a structure represented by formula (II)Wherein R is⁵Can independently be C_1-6An alkylene group; n is>1。

According to the embodiments of the present disclosure, the composition provided by the present disclosure can be used as an adhesive composition (adhesive composition) or a composition for preparing a foam. Here, the composition may further comprise a diisocyanate compound.

The present disclosure also provides a method for preparing the composition of the present disclosure.

The present disclosure also provides a material, wherein the material is prepared from the composition of the present disclosure.

In accordance with embodiments of the present disclosure, a foam is provided, wherein the foam is prepared from the composition of the present disclosure. According to embodiments of the present disclosure, the foam may be a product of the composition of the present disclosure obtained by a foaming process.

Compared with the prior art, the invention has the advantages that: the composition according to the invention is a homogeneous composition comprising an isocyanate derivative obtained by alcoholic depolymerization of a polyurethane and a polyether polyol, wherein the isocyanate derivative has no hydroxyl group. Since the polyurethane is subjected to alcoholysis polymerization by using a specific monoalcohol (having a specific chemical structure) as an alcoholysis agent, the isocyanate derivative obtained by the depolymerization reaction has no active hydroxyl group. When the composition of the invention is further used as a tack composition or a composition for preparing a foam, the isocyanate derivative in the composition of the invention will only act as an organic filler and will not affect the subsequent reaction of the polyether polyol. In addition, the homogeneous composition can be formed by reacting specific monoalcohol under normal pressure, and the homogeneous composition has low hydroxyl value, so that the composition obtained after depolymerization can be directly applied to polyurethane foaming (namely, a compound containing hydroxyl groups except polyether polyol is not required to be further purified and removed). Therefore, compared with the traditional polyurethane depolymerization reaction using dihydric alcohol (or polyhydric alcohol) as alcoholysis agent (i.e. producing isocyanate derivative with terminal hydroxyl), the composition of the invention can not only be applied to polyurethane soft foam foaming, but also be more suitable for mass production and improve economic benefit.

Detailed Description

The following is a detailed description of the compositions of the present disclosure, methods of making the same, and materials made therefrom. It is to be understood that the following description provides many different embodiments, or examples, for implementing different aspects of the disclosure. The specific components and arrangements described below are merely illustrative of the present disclosure. These are, of course, merely examples and are not intended to be limiting. Moreover, repeated reference numerals or designations may be used in various embodiments. These iterations are merely for simplicity and clarity of describing the present disclosure, and are not intended to represent any relationship between the various embodiments and/or structures discussed. In the present disclosure, the term "about" means that the amount specified may be increased or decreased by an amount recognized by those of ordinary skill in the art as being of a general and reasonable size.

The present disclosure provides a composition, a method of making the same, and a material made therefrom. According to an embodiment of the present disclosure, the composition is a homogeneous (homogenetic) composition comprising an isocyanate derivative obtained by alcohol depolymerization of polyurethane and a polyether polyol, wherein the isocyanate derivative has no hydroxyl group. Since the present disclosure depolymerizes polyurethane with alcohol by using a specific monoalcohol (having a specific chemical structure) as an alcoholysis agent, the isocyanate derivative obtained by the depolymerization reaction has no reactive hydroxyl group. When the composition of the present disclosure is further used as an adhesive composition or a composition for preparing a foam, the isocyanate derivative in the composition of the present disclosure is used only as an organic filler, and the subsequent reaction of the polyether polyol is not affected. In addition, the homogeneous composition formed by the reaction of the specific monoalcohol under normal pressure has low hydroxyl value, and the composition obtained after depolymerization can be directly applied to polyurethane foaming (i.e. without further purification to remove hydroxyl-containing compounds other than polyether polyol). As such, compared to the conventional depolymerization reaction of polyurethane with diol (or polyol) as alcoholysis agent (i.e. producing isocyanate derivative with terminal hydroxyl), the composition of the present disclosure can not only be applied to polyurethane soft foam foaming, but also be more suitable for mass production and increase economic benefits.

According to an embodiment of the present disclosure, the composition of the present disclosure includes about 50-99 parts by weight (e.g., about 55, 60, 65, 70, 75, 80, 85, 90, or 95 parts by weight) of a polyether polyol, and about 1-50 parts by weight (e.g., about 5, 10, 15, 20, 25, 30, 35, 40, or 45 parts by weight) of at least one compound having a structure represented by formula (I)

Wherein R is¹Can independently be C_1-6An alkylene group; r²Is thatR³Is C_1-6An alkylene group; i is more than or equal to 1; j is more than or equal to 0; k is 0, 1, or 2; when k is 1 or 2, R⁴Is C_1-24An alkyl group; or when k is 0, R⁴Is C_6-24An alkyl group; and B is independently OrWherein the polyether polyol has a weight average molecular weight (Mw) of between 200 and 10000.

According to the disclosed embodiment, the polyether polyol has a structure represented by formula (II)

Wherein R is⁵Can independently be C_1-6An alkylene group; n is>1。

According to embodiments of the present disclosure, the weight average molecular weight (Mw) of the polyether polyol having the structure represented by formula (II) may be between about 200 and 10000, such as between about 200 and 9000, between about 200 and 8000, between about 200 and 7000, between about 200 and 6000, between about 500 and 10000, between about 1000 and 10000, or between about 1000 and 8000. According to an embodiment of the present disclosure, the polyether polyol having the structure shown in formula (II) may be a homopolymer or a copolymer obtained by polymerizing at least one monomer, wherein the monomer may be ethylene oxide, propylene oxide, butylene oxide (epoxybutane), tetrahydrofuran (tetrahydrofuran), oxetane (oxyethane), glycerol (glycerol), trimethylolpropane, ethylene glycol, propylene glycol, butylene glycol, or pentylene glycol. For example, the polyether polyol may be polyethylene glycol, polypropylene glycol, polybutylene glycol, propylene oxide-ethylene oxide copolymer, glycerin-propylene oxide-ethylene oxide copolymer, trimethylolpropane-propylene oxide-ethylene oxide copolymer, ethylene glycol-propylene oxide-ethylene oxide copolymer, propylene glycol-propylene oxide-ethylene oxide copolymer, or polytetrahydrofuran. According to an embodiment of the present disclosure, i may be an integer from 4 to 226, such as an integer from 10 to 200, an integer from 20 to 180, an integer from 50 to 150, or an integer from 70 to 150.

According to an embodiment of the present disclosure, C_1-6The alkylene group may be a linear or branched (linear or branched) chain alkylene group. For example, C_1-6The alkylene group may be a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, or an isomer thereof (isomer). According to an embodiment of the present disclosure, C_1-24The alkyl group may be a linear or branched (linear or branched) chain alkyl group. For example, when k is 0, R⁴Can be hexyl (hexy)l), heptyl (heptadecyl), octyl (octyi), nonyl (nonyl), decyl (decyl), undecyl (undecyl), dodecyl (dodecyl), tridecyl (tridecyl), tetradecyl (tetradecyl), pentadecyl (pentadecyl), hexadecyl (hexadecyl), heptadecyl (heptadececyl), octadecyl (octadececyl), or isomers thereof (isomer). When k is 1 or 2, R⁴Can be methyl (methyl), ethyl (ethyl), propyl (propyl), butyl (butyl), pentyl (pentyl), hexyl (hexyl), heptyl (heptyl), octyl (octyl), nonyl (nonyl), decyl (decyl), undecyl (undecyl), dodecyl (dodecyl), tridecyl (tridecyl), tetradecyl (tetradecyl), pentadecyl (pentadecyl), hexadecyl (hexadecyl), heptadecyl (heptadecyl), octadecyl (octadecyl), or isomers thereof (isomer).

According to an embodiment of the present disclosure, R²May be the dehydroxylated residue of a single alcohol. Wherein the monohydric alcohol is 1-hexanol (1-hexanol), 1-heptanol (1-heptanol), 1-octanol (1-octanol), isooctanol (isooctanol), 1-nonanol (1-nonanol), isononanol (isoonanol), 1-decanol (1-decanol), 1-undecanol (1-undecyl alcohol), lauryl alcohol (laurylalcohol), 1-tridecanol (1-tridecylalcohol), isotridecyl alcohol (isotridecyl alcohol), 1-tetradecanol (1-tetracosanol), 1-pentadecanol (1-pentadecanol), 1-hexadecanol (1-hexadecanol), 1-n-heptadecanol (1-n-heptadecanol), 1-octadecanol (1-octadecanol), diethylene glycol (diethylene glycol), diethylene glycol diethyl ether (diethyl ether), diethylene glycol ether (diethyl ether), or mixtures thereof, Diethylene glycol monobutyl ether (diethylene glycol monobutyl ether), or ethylene glycol butyl ether (2-butroxyethonol).

In accordance with embodiments of the present disclosure, B may be the de-isocyanate residue of a diisocyanate compound. Wherein the diisocyanate compound is 2, 4-tolylene diisocyanate (2, 4-tolumene diisocyanate), 2, 5-tolylene diisocyanate (2, 5-tolumene diisocyanate), 2, 6-tolylene diisocyanate (2, 6-tolumene diisocyanate), hexamethylene diisocyanate (hexamethylene diisocyanate), pentamethylene diisocyanate (pentamethylene diisocyanate), isophorone diisocyanate (isophorone diisocyanate), dicyclohexylmethane diisocyanate (4,4' -Methylene diisocyanate), or 4,4' -methylenediphenyl diisocyanate (4,4' -Methylene diisocyanate).

According to the disclosed embodiment, the sum of the weight of the polyether polyol and the compound having the structure shown in formula (I) is 100 parts by weight.

According to an embodiment of the present disclosure, the compound having the structure of formula (I) can beOr(wherein i>1、j≥1)。

In accordance with an embodiment of the present disclosure,and(wherein i>1. The compounds with the structure shown by j ≧ 1) are isocyanate derivatives. In other words, when the polyurethane is subjected to alcoholysis polymerization using a specific monoalcohol (having a specific chemical structure) as the alcoholysis agent, the isocyanate derivative obtained by the depolymerization reaction may contain both of the above compounds.

According to an embodiment of the present disclosure, in the compound having the structure shown in formula (I), j may be an integer of 1 to 30, such as an integer of 1 to 25, an integer of 1 to 20, an integer of 1 to 15, an integer of 1 to 10, or an integer of 1 to 5. For example, j may be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30. In accordance with an embodiment of the present disclosure, in a compound having a structure represented by formula (I), the compound hasThe weight average molecular weight (Mw) of the groups of structure (a) may be between about 200 and 10000, for example between about 200 and 9000,Between about 200 and 8000, between about 200 and 7000, between about 200 and 6000, between about 500 and 10000, between about 1000 and 10000, or between about 1000 and 8000. According to the disclosed embodiment, the device is provided withThe structural groups are derived from polyether polyols. For example, the polyether polyol may be polyethylene glycol, polypropylene glycol, polybutylene glycol, propylene oxide-ethylene oxide copolymer, glycerin-propylene oxide-ethylene oxide copolymer, trimethylolpropane-propylene oxide-ethylene oxide copolymer, ethylene glycol-propylene oxide-ethylene oxide copolymer, propylene glycol-propylene oxide-ethylene oxide copolymer, or polytetrahydrofuran. According to an embodiment of the present disclosure, i may be an integer from 4 to 226, such as an integer from 10 to 200, an integer from 20 to 180, an integer from 50 to 150, or an integer from 70 to 150.

In accordance with embodiments of the present disclosure, the compositions of the present disclosure may comprise two or more compounds having a structure according to formula (I). When the compositions of the present disclosure comprise two or more compounds having the structure of formula (I), R of the compounds having the structure of formula (I)¹、R²B, and i are the same, with j only being different.

According to embodiments of the present disclosure, the composition is a homogeneous (homogeneous) composition even though the combination of the present disclosure includes both a polyether polyol having a structure of formula (I) and a compound having a structure of formula (II). In addition, when the composition of the present disclosure may include two or more compounds having the structure shown in formula (II), the two or more compounds having the structure shown in formula (II) also have isocyanate derivatives without hydroxyl group. As such, when the composition of the present disclosure is further used as an adhesive composition or a composition for preparing a foam, the isocyanate derivative (the compound having the structure represented by formula (II)) in the composition of the present disclosure is only used as an organic filler, and does not affect the subsequent reaction of the polyether polyol.

According to the disclosed embodiment, the composition of the present disclosure may further include a diisocyanate compound as an adhesive composition (adhesive composition) or a composition for preparing a foam. According to an embodiment of the present disclosure, the diisocyanate compound may be 2,4-toluene diisocyanate (2,4-toluene diisocyanate), 2,5-toluene diisocyanate (2,5-toluene diisocyanate), 2,6-toluene diisocyanate (2,6-toluene diisocyanate), hexamethylene diisocyanate (hexamethylene diisocyanate), pentamethylene diisocyanate (pentamethylene diisocyanate), isophorone diisocyanate (isophorone diisocyanate), dicyclohexylmethane diisocyanate (4,4' -Methylene dicyclohexyl diisocyanate), 4' -Methylene diphenyl diisocyanate (4,4' -Methylene diphenyl diisocyanate), lysine diisocyanate (lysine diisocyanate), or a combination thereof. In accordance with embodiments of the present disclosure, in the composition of the present disclosure, in order to completely react the polyether polyol having the structure represented by formula (II) with the diisocyanate compound, the molar ratio of the diisocyanate compound to the polyether polyol may be about 1:1 to 2.2: 1.

According to embodiments of the present disclosure, the composition may further comprise an additive. The amount of the additive is not limited and can be adjusted according to actual needs by those skilled in the art. For example, the composition may further comprise about 0.1 to 30 parts by weight of an additive, such as about 0.1 to 25 parts by weight, 0.1 to 20 parts by weight, 0.1 to 15 parts by weight, or 0.1 to 10 parts by weight. Here, the sum of the weight of the polyether polyol and the compound having the structure represented by the formula (II) is 100 parts by weight. Wherein the additive is an organometallic catalyst (organic catalyst) (e.g. dibutyltin dilaurate, stannous octoate, dibutyltin diacetate, dioctyltin diacetate, dibutyltin maleate, dibutyltin-2-ethylhexanoate, dibutyltin-2-ethoxide or dithiol), an amine catalyst (amine catalyst) (e.g. triethylenediamine, triethylamine), a crosslinking agent (cross-linking agent), a foaming agent (foaming agent), a foaming agent (biolizer), a plasticizer (plasticizer), a melt strength enhancer (modifier), an anti-static antioxidant (anti-static agent), an antistatic agent (antistatic agent), a Flame retardant (antioxidant), a metal catalyst (metal catalyst), a metal (metal) and a metal (metal oxide), a metal (metal oxide), a metal oxide, water, or a combination of the foregoing.

According to an embodiment of the present disclosure, the method for alcoholysis polymerization of polyurethane disclosed herein may comprise the following steps. First, the monoalcohol and the catalyst are mixed to obtain a mixture. Subsequently, the mixture is warmed to 150 ℃ to 230 ℃. Polyurethane is then added to the mixture and subjected to an alcoholysis reaction under nitrogen to yield a product, which can be from 1 hour to 24 hours. After the alcoholysis reaction, the polyurethane is converted into polyether polyol and isocyanate derivatives. Thus, the product may comprise a catalyst, a polyether polyol and an isocyanate derivative. According to embodiments of the present disclosure, the isocyanate derivative may comprise at least one compound having formula (I). Here, the isocyanate derivatives may be classified into "monomeric isocyanate derivatives" and "oligomeric isocyanate derivatives" according to the difference in the degree of depolymerization. The higher the degree of depolymerization of the polyurethane, the greater the amount of "monomeric isocyanate derivative"; and, if the degree of depolymerization of the polyurethane is low, the amount of the "oligomer-type isocyanate derivative" is large. The degree of depolymerization of the polyurethane can be adjusted by adjusting the reaction time and temperature of the depolymerization reaction of the alcohol.

It is noted that the isocyanate derivatives (i.e., at least one isocyanate derivative having the structure of formula (I)) obtained by the alcoholysis polymerization process of polyurethanes described herein do not have hydroxyl groups (i.e., no hydroxyl group isocyanate derivatives). According to the disclosed embodiment, the product obtained after the alcohol depolymerization of polyurethane can be further subjected to a reduced pressure distillation process to remove the unreacted unit alcohol.

According to embodiments of the present disclosure, the catalyst may be an organic metal catalyst (organometallic catalyst), an amine catalyst (amine catalyst), or a combination thereof. For example, the organometallic catalyst may be dibutyltin dilaurate (dibutyl dilautate), stannous isooctanoate (stannous octoate), dibutyltin diacetate (dibutyl diacetate), dioctyltin diacetate (dioctyl diacetate), dibutyltin dibutylmaleate (dibutyl maleate), dibutyltin di-2-ethylhexanoate (dibutyl di-2-ethylhexoate), dibutyltin dithiolate (dibutyl dithiolate), isooctyl methyltin trithioacetate (isooctyl trithioacetate), or isooctyl dimethyltin dithioacetate (dimethyl mercaptide). The amine catalyst may be triethylenediamine (triethylenediamine), or triethylamine (triethylamine). According to an embodiment of the present disclosure, the polyurethane may be 2,4-toluene diisocyanate (2,4-toluene diisocyanate), 2,5-toluene diisocyanate (2,5-toluene diisocyanate), 2,6-toluene diisocyanate (2,6-toluene diisocyanate), hexamethylene diisocyanate (hexamethylene diisocyanate), pentamethylene diisocyanate (pentamethylene diisocyanate), isophorone diisocyanate (isophorone diisocyanate), dicyclohexylmethane diisocyanate (4,4' -Methylene dicyclohexyl diisocyanate), 4' -Methylene diphenyl diisocyanate (4,4' -Methylene diphenyl diisocyanate), lysine diisocyanate (lysine diisocyanate), or a combination thereof. According to an embodiment of the present disclosure, the monoalcohol may have a structure represented by formula (III)

Wherein R is³Is independently C_1-6An alkylene group; m is 0, 1, or 2; and, R when m is 1 or 2⁴Is C_1-24Alkyl, or R when m is 0⁴Is C_6-24An alkyl group. According to embodiments of the present disclosure, the boiling point of the unit alcohol described in the present disclosure is greater than or equal to 170 ℃. As such, the polyurethane can be alcoholyzed at 150-230 ℃ and atmospheric pressure (i.e., about 1 atmosphere) with the monomeric alcohol having the structure of formula (III) described in the present disclosure. According to an embodiment of the present disclosure, the monohydric alcohol may be 1-hexanol, 1-heptanol, 1-octanol, isooctanol, 1-nonanol, isononanol, 1-decanol, 1-undecanol, lauryl alcohol, 1-tridecanol, isotridecanol, 1-tetradecanol, 1-decadecanolPenta-alkanol, 1-hexadecanol, 1-n-heptadecanol, 1-octadecanol, diethylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, or ethylene glycol butyl ether. According to embodiments of the present disclosure, the weight ratio of the unit alcohol to the catalyst may be about 5to 200, such as 5, 10, 15, 20, 50, 80, 100, 120, 150, 180, or 200. According to embodiments of the present disclosure, the weight ratio of polyurethane to the unit alcohol may be about 1 to 10, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.

In accordance with embodiments of the present disclosure, a polyether polyol may further be provided to mix with the monol and the catalyst when preparing the mixture. According to an embodiment of the present disclosure, the polyether polyol may be a homopolymer or a copolymer obtained by polymerizing at least one monomer, wherein the monomer may be ethylene oxide, propylene oxide, butylene oxide (epoxybutane), tetrahydrofuran (tetrahydrofuran), oxetane (oxyethane), glycerol (glycerol), trimethylolpropane, ethylene glycol, propylene glycol, butylene glycol, or pentylene glycol. For example, the polyether polyol may be polyethylene glycol, polypropylene glycol, polybutylene glycol, propylene oxide-ethylene oxide copolymer, glycerin-propylene oxide-ethylene oxide copolymer, trimethylolpropane-propylene oxide-ethylene oxide copolymer, ethylene glycol-propylene oxide-ethylene oxide copolymer, propylene glycol-propylene oxide-ethylene oxide copolymer, or polytetrahydrofuran. According to embodiments of the present disclosure, the weight ratio of the polyether polyol to the monol may be about 1 to 10, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10.

According to certain embodiments of the present disclosure, the compositions of the present disclosure comprise the product of the alcohol depolymerization of polyurethane with specific monoalcohols. Here, even if a part of the unit alcohol remains in the composition, since the unit alcohol has only a hydroxyl group, the subsequent reaction of the polyether polyol (for example, the reaction of the polyether polyol with the diisocyanate compound to obtain polyurethane) is less affected. According to certain embodiments of the present disclosure, the compositions of the present disclosure comprise the product of the alcohol depolymerization of a polyurethane with a specific mono-alcohol and removal of the mono-alcohol. For example, the alcohol unit as alcoholysis agent can be removed by distillation under reduced pressure. According to the embodiments of the present disclosure, the composition of the present disclosure may further include a polyether polyol in addition to the product obtained by the alcohol depolymerization of the polyurethane and the specific unit alcohol, so that the weight parts of the polyether polyol having the structure of formula (II) and the compound having the structure of formula (I) in the composition of the present disclosure meet a predetermined amount. In accordance with embodiments of the present disclosure, only polyether polyols having a structure according to formula (II) in the compositions of the present disclosure have hydroxyl groups. According to the embodiment of the present disclosure, by using the monoalcohol having the structure shown in formula (III) described in the present disclosure, the product obtained after the depolymerization of the polyurethane with alcohol can be a homogeneous composition, and the homogeneous composition has a lower hydroxyl value. According to an embodiment of the present disclosure, the hydroxyl value of the composition of the present disclosure is about 10mgKOH/g to 80mgKOH/g, for example, 10mgKOH/g to 70mgKOH/g, or 10mgKOH/g to 60 mgKOH/g. Thus, the product obtained by the method for alcoholysis polymerization of polyurethane according to the present disclosure can be directly applied to polyurethane foaming (i.e., without further purification to remove hydroxyl-containing compounds other than polyether polyol).

The isocyanate derivative produced by the conventional alcoholysis polymerization process of polyurethanes using a polyol as an alcoholysis agent is an aromatic dicarbamate polyol. Therefore, the resulting products of the depolymerization of the polyurethane alcohol have a high hydroxyl value, thereby limiting the applicability thereof. For example, when the alcoholysis polymerization product of polyurethane with high hydroxyl value is applied to foam of polyurethane foam to form foam, the aromatic dicarbonate polyol in the product accelerates the crosslinking rate with diisocyanate compound, which results in increased closed cell rate of the foam, and thus unable to effectively form cells, which affects the foamability (i.e. the foam shrinks greatly when cooling to form a more compact material). In addition, when the content of aromatic dicarbamate polyol in the composition is 2% by weight or more, the foamability of the foam obtained by soft foam foaming is affected. Therefore, when the product obtained by the conventional alcoholysis polymerization method of polyurethane using polyol as alcoholysis agent is applied to the soft foam foaming, the isocyanate derivative (i.e., aromatic dicarbamate polyol) contained in the product is further removed. Since the present disclosure uses specific monoalcohols to carry out the alcoholysis polymerization of polyurethanes, the isocyanate derivatives produced have no hydroxyl groups, and therefore, even if the content of the hydroxyl-free isocyanate derivatives in the composition reaches 20% by weight, the subsequent reaction of the polyether polyols in the composition is not affected (the hydroxyl-free isocyanate derivatives are used only as organic fillers and do not react with diisocyanates). In addition, when short chain monoalcohols (such as methanol, ethanol, or propanol) are used as alcoholysis agents, isocyanate derivatives having hydroxyl groups are not produced even after the polyurethane is subjected to an alcohol depolymerization reaction. However, due to the low boiling point of methanol, the alcoholysis polymerization of polyurethane needs to be carried out at high temperature and high pressure (160-300 deg.C, 15MPa), resulting in increased requirements for processing equipment.

In accordance with an embodiment of the present disclosure, a method for preparing a composition is provided. The method comprises the following steps: providing 1-50 parts by weight of an organic filler, wherein the organic filler is an isocyanate derivative obtained by carrying out alcoholysis reaction on polyurethane by using a unit alcohol; providing 50-99 parts by weight of polyether polyol, wherein the sum of the weight of the organic filler and the polyether polyol is 100 parts by weight; providing a diisocyanate compound, wherein the molar ratio of the diisocyanate compound to the polyether polyol is 1:1 to 2.2: 1; and mixing the organic filler, the polyether polyol, and the diisocyanate compound to obtain the desired composition.

According to the disclosed embodiment, the organic filler has a structure shown in formula (I)

Wherein R is¹Is independently C_1-6An alkylene group; r²Is thatR³Is C_1-6An alkylene group; i is more than or equal to 1; j is more than or equal to 0; k is 0, 1, or 2; when k is 1 or 2, R⁴Is C_1-24An alkyl group; or whenWhen k is 0, R⁴Is C_6-24An alkyl group; and B is independently Or

According to an embodiment of the present disclosure, the polyether polyol is obtained by conducting an alcoholysis reaction on the polyurethane.

According to an embodiment of the present disclosure, the polyether polyol has a weight average molecular weight (Mw) between 200 and 10000. According to an embodiment of the present disclosure, the polyether polyol may be a homopolymer or a copolymer obtained by polymerizing at least one monomer, wherein the monomer may be ethylene oxide, propylene oxide, butylene oxide (epoxybutane), tetrahydrofuran (tetrahydrofuran), oxetane (oxyethane), glycerol (glycerol), trimethylolpropane, ethylene glycol, propylene glycol, butylene glycol, or pentylene glycol. For example, the polyether polyol may be polyethylene glycol, polypropylene glycol, polybutylene glycol, propylene oxide-ethylene oxide copolymer, glycerin-propylene oxide-ethylene oxide copolymer, trimethylolpropane-propylene oxide-ethylene oxide copolymer, ethylene glycol-propylene oxide-ethylene oxide copolymer, propylene glycol-propylene oxide-ethylene oxide copolymer, or polytetrahydrofuran.

According to the disclosed embodiment, the unit alcohol may be 1-hexanol (1-hexanol), 1-heptanol (1-heptanol), 1-octanol (1-octanol), isooctanol (isooctyl alcohol), 1-nonanol (1-nonanol), isononyl alcohol (isononyl alcohol), 1-decanol (1-decanol), 1-undecanol (1-undecyl alcohol), lauryl alcohol (lauryl alcohol), 1-tridecanol (1-tridecyl alcohol), isotridecyl alcohol (isotridecyl alcohol), 1-tetradecanol (1-tetradecanol), 1-pentadecanol (1-pentadecanol), 1-hexadecanol (1-hexadecanol), 1-n-heptadecanol (1-n-heptadecanol), 1-octadecanol (1-octadecanol), 1-hexadecanol (1-hexadecanediol), 1-heptadecanol (1-heptadecanol), 1-octadecanol (1-octanediol), 1-heptadecanol (1-octanediol), or 1-heptanediol (1-heptanediol), or diethylene glycol (1-dimethyl ether), Diethylene glycol ethyl ether (diethylene glycol monoethyl ether), diethylene glycol butyl ether (diethylene glycol monobutyryl ether), or ethylene glycol butyl ether (2-butoxyyethane).

In accordance with certain embodiments of the present disclosure, there is also provided a material that can be prepared from the composition described herein. According to certain embodiments of the present disclosure, the material may comprise a cured product of a composition described herein. According to the disclosed embodiments, since the composition disclosed herein can be used as an adhesive composition, the material can be used as an adhesive layer. According to embodiments of the present disclosure, the material may be a foam because the composition of the present disclosure may be used as a composition for preparing a foam.

In accordance with embodiments of the present disclosure, a foam is provided, wherein the foam is prepared from the composition of the present disclosure. According to embodiments of the present disclosure, the foam may be a product of the composition of the present disclosure obtained by a foaming process.

The foregoing and other objects, features, and advantages of the disclosure will be apparent from the following more particular description:

preparation example 1

250 g of polyurethane foam (obtained by reacting 2,4-toluene diisocyanate (2,4-toluene diisocyanate) and polypropylene glycol (weight average molecular weight (Mw) of about 3000)) was cut with a guillotine to obtain polyurethane cotton wool having a size of less than 3 cm wide. Next, 200 g of isooctanol, 542 g of polypropylene glycol (weight average molecular weight (Mw) of about 3000), and 8 g of stannous isooctanoate (stannou octoate) were sequentially added to a reaction flask and stirred under nitrogen to obtain a mixture. The reaction flask was then heated to 170 ℃. Next, polyurethane crumbed cotton was added to the reaction flask at a feed rate of 50 g/min, and alcoholysis polymerization of polyurethane was carried out at 170 ℃ and atmospheric pressure with a stirring rate of 150rpm for 6 hours. Next, excess isooctanol was removed by distillation under reduced pressure (5torr, 190 ℃ C.) to obtain composition (1), wherein composition (1) was a homogeneous composition. Subsequently, the hydroxyl value (hydroxyl value) and amine value (amine value) of composition (1) were measured, and the results are shown in table 1.

Preparation example 2

250 g of polyurethane foam (obtained by reacting 2,4-toluene diisocyanate (2,4-toluene diisocyanate) and polypropylene glycol (weight average molecular weight (Mw) of about 5000)) was cut with a cutter to obtain polyurethane broken cotton having a size of less than 3 cm wide. Next, 200 g of isooctanol, 542 g of polypropylene glycol (weight average molecular weight (Mw) of about 5000), and 8 g of stannous isooctanoate (stannou octoate) were sequentially added to a reaction flask and stirred under nitrogen to obtain a mixture. The reaction flask was then heated to 170 ℃. Next, polyurethane crumbed cotton was added to the reaction flask at a feed rate of 50 g/min, and alcoholysis polymerization of polyurethane was carried out at 170 ℃ and atmospheric pressure with a stirring rate of 150rpm for 6 hours. Next, excess isooctanol was removed by distillation under reduced pressure (5torr, 190 ℃ C.) to obtain composition (2), wherein composition (2) was a homogeneous composition. Subsequently, the hydroxyl value (hydroxyl value) and amine value (amine value) of composition (2) were measured, and the results are shown in table 1.

Preparation example 3

250 g of polyurethane foam (obtained by reacting 2,4-toluene diisocyanate (2,4-toluene diisocyanate) and polypropylene glycol (weight average molecular weight (Mw) of about 3000)) was cut with a guillotine to obtain polyurethane cotton wool having a size of less than 3 cm wide. Next, 50 g of diethylene glycol ethyl ether (diethylene glycol monoethyl ether), 692 g of polypropylene glycol (weight average molecular weight (Mw) of about 3000), and 8 g of stannous isooctanoate (stannous octoate) were sequentially added to a reaction flask and stirred under nitrogen to obtain a mixture. The reaction flask was then heated to 170 ℃. Next, polyurethane crumbed cotton was added to the reaction flask at a feed rate of 50 g/min, and alcoholysis polymerization of polyurethane was carried out at 170 ℃ and atmospheric pressure with a stirring rate of 150rpm for 6 hours. Next, excess isooctanol was removed by distillation under reduced pressure (5torr, 190 ℃ C.) to obtain composition (3), wherein composition (3) was a homogeneous composition. Subsequently, the hydroxyl value (hydroxyl value) and amine value (amine value) of the composition (3) were measured, and the results are shown in table 1.

Preparation example 4

250 g of polyurethane foam (obtained by reacting 2,4-toluene diisocyanate (2,4-toluene diisocyanate) and polypropylene glycol (weight average molecular weight (Mw) of about 3000)) was cut with a guillotine to obtain polyurethane cotton wool having a size of less than 3 cm wide. Subsequently, 50 g of 1-octadecanol (octadecanol-1-ol), 692 g of polypropylene glycol (weight average molecular weight (Mw) of about 3000), and 8 g of stannous isooctanoate (stannous octoate) were sequentially added to a reaction flask and stirred under nitrogen to obtain a mixture. The reaction flask was then heated to 170 ℃. Next, polyurethane crumbed cotton was added to the reaction flask at a feed rate of 50 g/min, and alcoholysis polymerization of polyurethane was carried out at 170 ℃ and atmospheric pressure with a stirring rate of 150rpm for 6 hours. Next, excess isooctanol was removed by distillation under reduced pressure (5torr, 190 ℃ C.) to obtain composition (4), wherein composition (4) was a homogeneous composition. Subsequently, the hydroxyl value (hydroxyl value) and amine value (amine value) of the composition (4) were measured, and the results are shown in table 1.

Preparation example 5

250 g of polyurethane foam (obtained by reacting 2,4-toluene diisocyanate (2,4-toluene diisocyanate) and polypropylene glycol (weight average molecular weight (Mw) of about 3000)) was cut with a guillotine to obtain polyurethane cotton wool having a size of less than 3 cm wide. Next, 50 grams of butyl ethylene glycol (2-butoxyethane), 692 grams of polypropylene glycol (weight average molecular weight (Mw) about 3000), and 8 grams of stannous isooctanoate (stannou octoate) were added sequentially to a reaction flask and stirred under nitrogen to give a mixture. The reaction flask was then heated to 170 ℃. Next, polyurethane crumbed cotton was added to the reaction flask at a feed rate of 50 g/min, and alcoholysis polymerization of polyurethane was carried out at 170 ℃ and atmospheric pressure with a stirring rate of 150rpm for 6 hours. Next, excess isooctanol was removed by distillation under reduced pressure (5torr, 190 ℃ C.) to obtain composition (5), wherein composition (5) was a homogeneous composition. Subsequently, the hydroxyl value (hydroxyl value) and amine value (amine value) of the composition (5) were measured, and the results are shown in table 1.

Comparative preparation example 1

400 g of polyurethane foam (obtained by reacting 2,4-toluene diisocyanate (2,4-toluene diisocyanate) and polypropylene glycol (weight average molecular weight (Mw) of about 3000)) was cut with a guillotine to obtain polyurethane cotton wool having a size of less than 3 cm wide. Next, 592 grams of glycerol, and 8 grams of stannous isooctanoate (stannou octoate) were added sequentially to a reaction flask and stirred under nitrogen to give a mixture. The reaction flask was then heated to 170 ℃. Next, polyurethane crumbed cotton was added to the reaction flask at a feed rate of 50 g/min, and alcoholysis polymerization of polyurethane was carried out at 170 ℃ while maintaining a stirring rate of 150rpm (reaction time: 6 hours), to obtain composition (6). Observation of the composition (6) revealed that the composition (6) was apparently not an upper and lower layer, and was not a homogeneous composition. Subsequently, the hydroxyl value (hydroxyl value) and amine value (amine value) of the composition (6) were measured, and the results are shown in table 1.

Comparative preparation example 2

400 grams of polyurethane foam (from 2,4-toluene diisocyanate (2,4-toluene diisocyanate) and polypropylene glycol (weight average molecular weight (Mw) about 3000) was chopped with a guillotine to give polyurethane foam pieces having a size of less than 3 cm wide, then 25 grams of diethylene glycol (DEG), 717 grams of polypropylene glycol (weight average molecular weight (Mw) about 3000), and 8 grams of stannous isooctanoate (stannous octoate) were added sequentially to a reaction flask and stirred under nitrogen to give a mixture, then the reaction flask was heated to 190 ℃. then polyurethane foam pieces were added to the reaction flask at a feed rate of 50 grams/minute and the alcoholysis polymerization of polyurethane was carried out at 170 ℃ for 6 hours while maintaining a stirring rate of 150rpm to give composition (7) (composition), the hydroxyl value (hydroxyl value) and amine value (amine value) of composition (7) were measured, and the results are shown in table 1.

TABLE 1

As can be seen from Table 1, with polyols (e.g., glycerol or diethylene glycol) as the polyurethane alcoholysis agent, the resulting composition has a high hydroxyl number and is prone to product delamination due to polarity relationships. In contrast to preparations 1 to 3, the compositions obtained were homogeneous with a low hydroxyl number, since the specific monoalcohols were used as the polyurethane alcoholysis agent.

Polyurethane foaming process

Examples 1 to 4

Foaming compositions (1) to (4) were prepared from composition (1), polypropylene glycol (weight average molecular weight (Mw) of about 3000), 2,4-Toluene Diisocyanate (TDI), foam stabilizer (product number Tegostab B8158), water, amine catalyst (product number a33), and organometallic catalyst (stannous isooctanoate), respectively, wherein the compositions of the foaming compositions (1) to (4) were as shown in table 2. In the foaming compositions (1) to (4), the number ratio of isocyanate groups to hydroxyl groups is about 1.05: 1.

Then, the foam compositions (1) to (4) are subjected to a soft foam foaming process to obtain foams (1) to (4), respectively. The foaming process comprises pouring the foaming composition into a mold of 15cm × 15cm × 5cm, and standing at room temperature for more than 2 hours to solidify. In the foaming process, the volume shrinkage ratio of the obtained foam was observed, and if the volume shrinkage ratio is less than 5 vol%, it is defined as having foamability. Next, the compressive strength of the foam was measured, and the results are shown in Table 2. Compressive strength was measured in accordance with the method specified in ASTM-D-D3574.

TABLE 2

Examples 5to 7

Foaming compositions (5) to (7) were prepared from composition (2), polypropylene glycol (weight average molecular weight (Mw) of about 5000), 2,4-Toluene Diisocyanate (TDI), foam stabilizer (product number Tegostab B8158), water, amine catalyst (product number a33), and organometallic catalyst (stannous isooctanoate), respectively, wherein the compositions of the foaming compositions (5) to (7) were as shown in table 3. In the foaming compositions (5) to (7), the number ratio of isocyanate groups to hydroxyl groups was about 105: 1.

Then, the foam compositions (5) to (7) were subjected to a soft foam foaming process to obtain foams (5) to (7), respectively. The foaming process comprises pouring the foaming composition into a mold of 15cm × 15cm × 5cm, and standing at room temperature for more than 2 hours to solidify. In the foaming process, the volume shrinkage ratio of the obtained foam was observed, and if the volume shrinkage ratio is less than 5 vol%, it is defined as having foamability. Next, the compressive strength of the foam was measured, and the results are shown in Table 3.

Example 8

Foaming composition (8) was prepared from composition (3), polypropylene glycol (weight average molecular weight (Mw) of about 6000), isophorone diisocyanate (IPDI), foam stabilizer (product number Tegostab B8158), water, amine catalyst (product number a33), and organometallic catalyst (stannous isooctanoate), wherein the composition of the foaming composition (8) was as shown in table 3. In this foaming composition (8), the number ratio of isocyanate groups to hydroxyl groups is about 105: 1.

Then, the foam composition (8) is subjected to a soft foam foaming process to obtain foams (8). The foaming process comprises pouring the foaming composition into a mold of 15cm × 15cm × 5cm, and standing at room temperature for more than 2 hours to solidify. In the foaming process, the volume shrinkage ratio of the obtained foam was observed, and if the volume shrinkage ratio is less than 5 vol%, it is defined as having foamability. Next, the compressive strength of the foam was measured, and the results are shown in Table 3.

TABLE 3

Comparative examples 1 to 2

Foaming compositions (9) to (10) were prepared from composition (4), polypropylene glycol (weight average molecular weight (Mw) of about 3000), 2,4-Toluene Diisocyanate (TDI), foam stabilizer (product number Tegostab B8158), water, amine catalyst (product number a33), and organometallic catalyst (stannous isooctanoate), respectively, wherein the compositions of the foaming compositions (9) to (10) were as shown in table 4. In the foaming compositions (9) to (10), the number ratio of isocyanate groups to hydroxyl groups was about 105: 1.

Then, the foam compositions (9) to (10) were subjected to a soft foam foaming process to obtain foams (9) to (10), respectively. The foaming process comprises pouring the foaming composition into a mold of 15cm × 15cm × 5cm, and standing at room temperature for more than 2 hours to solidify. In the foaming process, the volume shrinkage ratio of the obtained foam was observed, and if the volume shrinkage ratio is less than 5 vol%, it is defined as having foamability. Next, the compressive strength of the foam was measured, and the results are shown in Table 4.

TABLE 4

Comparative examples 3 to 5

Foaming compositions (11) to (13) were prepared from composition (5), polypropylene glycol (weight average molecular weight (Mw) of about 3000), 2,4-Toluene Diisocyanate (TDI), foam stabilizer (product number Tegostab B8158), water, amine catalyst (product number a33), and organometallic catalyst (stannous isooctanoate), respectively, wherein the compositions of the foaming compositions (11) to (13) were as shown in table 5. In the foaming compositions (11) to (13), the number ratio of isocyanate groups to hydroxyl groups was about 105: 1.

Then, the foam compositions (11) to (13) are subjected to a soft foam foaming process to obtain foams (11) to (13), respectively. The foaming process comprises pouring the foaming composition into a mold of 15cm × 15cm × 5cm, and standing at room temperature for more than 2 hours to solidify. In the foaming process, the volume shrinkage ratio of the obtained foam was observed, and if the volume shrinkage ratio is less than 5 vol%, it is defined as having foamability. Next, the compressive strength of the foam was measured, and the results are shown in Table 5.

TABLE 5

As is apparent from tables 2 to 5, when a polyol is used as the alcoholysis agent, the resulting isocyanate derivative has a hydroxyl group (i.e., the resulting product has a high hydroxyl value), and the crosslinking rate with the diisocyanate compound is increased, so that the closed cell ratio of the foam is increased, and cells are not efficiently formed, thereby affecting the foamability. Since the present disclosure uses a specific alcohol unit to perform the alcoholysis polymerization of polyurethane, the isocyanate derivative generated has no hydroxyl group, and even if the hydroxyl-free isocyanate derivative has a high content in the composition, the foamability is not affected, and thus the present disclosure can be used in the soft foam foaming process of polyurethane.

Adhesive composition

Example 9

Adhesive composition (1) was prepared from composition (1), polypropylene glycol (weight average molecular weight (Mw) about 3000), Hexamethylene Diisocyanate (HDI), amine catalyst (commercial number a33), and organometallic catalyst (stannous isooctanoate), wherein the compositional composition of adhesive composition (1) is shown in table 6. Next, the adhesive composition (1) was subjected to a curing test and an adhesion test, and the results are shown in table 6. The adhesive composition was tested for curability at 30 ℃ and 50% RH, and passed the curability Test when the 1 day cure depth reached 5mm and the hardness reached A30, and the adhesion Test formula (T-Peel Test) was measured according to the method specified in ASTM-D1876, and the adhesive composition was used to adhere two sheets of Polycarbonate (Polycarbonate) having a length of 300mm and a width of 25.4mm, and the adhesive strength was measured to reach 5kgf/cm²I.e., passes the adhesion test.

Example 10

Adhesive composition (2) was prepared from composition (2), polypropylene glycol (weight average molecular weight (Mw) of about 5000), isophorone diisocyanate (IPDI), amine catalyst (product number a33), and organometallic catalyst (stannous isooctanoate), wherein the compositional composition of adhesive composition (2) is shown in table 6. Next, the adhesive composition (2) was subjected to a curing test and an adhesion test, and the results are shown in table 6.

TABLE 6

As can be seen from Table 6, although the composition of the present disclosure has a content of non-hydroxyl isocyanate derivatives higher than 25%, the composition still has curability and adhesiveness, and can be used as an adhesive composition.

Although the present disclosure has been described with reference to several embodiments, it should be understood that the scope of the present disclosure is not limited to the embodiments described above, but is intended to be defined by the appended claims.