Production methods of polyester and polyurethane
View Patent ↗At the time of producing a polyester by using a dicarboxylic acid component and a biomass-resource-derived diol as raw materials, a polyester is efficiently produced with good color tone, as the raw material diol derived from biomass resources, a diol in which the content of a cyclic carbonyl compound having a carbon atom number of 5 or 6 is from 0.01 to 12 ppm by mass, is used, and by controlling the content of a cyclic carbonyl compound having a carbon atom number of 5 or 6 in the raw material diol to fall in a prescribed range, the color tone of the polyester is improved.
1. A method for producing a polyester, comprising:
performing a reaction by using, as raw materials, a dicarboxylic acid component, and a diol produced directly from a biomass-resource-derived substance by a fermentation process,
wherein a content of a cyclic carbonyl compound having a carbon atom number of 5 or 6 in the diol is from 0.01 ppm to 12 ppm by mass, and
wherein said diol produced directly from a biomass-resource-derived substance by a fermentation process is selected from the group consisting of ethylene glycol, 2-methyl-1,3-propanediol, neopentyl glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, and isosorbide.
2. The method for producing a polyester according to claim 1 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (I):
wherein in formula (I), each of R 1 to R 4 independently represents a hydrogen atom, a methyl group, a formyl group or an acetyl group, with the proviso that one of R 1 to R 4 is a formyl group or an acetyl group, and the total number of carbon atoms contained in respective groups of R 1 to R 4 is 2 or less.
3. The method for producing a polyester according to claim 1 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (II):
wherein in formula (II), X represents a carbon atom or an oxygen atom, with the proviso that 1 X is an oxygen atom, each of R 5 to R 9 independently represents a methyl group or a hydrogen atom, and the total number of carbon atoms contained in respective groups of R 5 to R 9 is 1 or less.
4. The method for producing a polyester according to claim 1 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (III) and a content of the compound having a structure represented by formula (III) in the diol is 6 ppm by mass or less:
wherein in formula (III), each of R 10 to R 13 independently represents a methyl group or a hydrogen atom, and the total number of carbon atoms contained in respective groups of R 10 to R 13 is 1 or less.
5. The method for producing a polyester according to claim 1 ,
wherein the diol is 1,4-butanediol,
the dicarboxylic acid component is at least one of a terephthalic acid and a terephthalic acid alkylate, and
the polyester is polybutylene terephthalate.
6. The method for producing a polyester according to claim 5 ,
wherein the 1,4-butanediol contains from 1 to 99 ppm by mass of 1-acetoxy-4-hydroxybutane.
7. The method for producing a polyester according to claim 1 ,
wherein a content of a nitrogen atom compound in the diol is from 0.1 to 50 ppm by mass in terms of nitrogen atom.
8. The method for producing a polyester according to claim 1 , further comprising, prior to said performing a reaction, subjecting a biomass resource to a fermentation process wherein said fermentation process comprises pretreating said biomass resource and further subjecting the biomass resource to saccharification.
9. A method for producing a polyester polyol, comprising:
performing reaction by using, as raw materials, a dicarboxylic acid component, and a diol produced directly from a biomass-resource-derived substance by a fermentation process,
wherein a content of a cyclic carbonyl compound having a carbon atom number of 5 or 6 in the diol is from 0.01 ppm to 12 ppm by mass, and
wherein said diol produced directly from a biomass-resource-derived substance by a fermentation process is selected from the group consisting of ethylene glycol, 2-methyl-1,3-propanediol, neopentyl glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, and isosorbide.
10. The method for producing a polyester polyol according to claim 9 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (I):
wherein in formula (I), each of R 1 to R 4 independently represents a hydrogen atom, a methyl group, a formyl group or an acetyl group, with the proviso that one of R 1 to R 4 is a formyl group or an acetyl group, and the total number of carbon atoms contained in respective groups of R 1 to R 4 is 2 or less.
11. The method for producing a polyester polyol according to claim 9 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (II):
wherein in formula (II), X represents a carbon atom or an oxygen atom, with the proviso that 1 X is an oxygen atom, each of R 5 to R 9 independently represents a methyl group or a hydrogen atom, and the total number of carbon atoms contained in respective groups of R 5 to R 9 is 1 or less.
12. The method for producing a polyester polyol according to claim 9 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (III):
wherein in formula (III), each of R 10 to R 13 independently represents a methyl group or a hydrogen atom, and the total number of carbon atoms contained in respective groups of R 10 to R 13 is 1 or less.
13. The method for producing a polyester polyol according to claim 10 ,
wherein the diol is 1,4-butanediol,
the dicarboxylic acid component is adipic acid, and
the polyester polyol is polybutylene adipate.
14. The method for producing a polyester polyol according to claim 13 ,
wherein the 1,4-butanediol contains from 1 to 99 ppm by mass of 1-acetoxy-4-hydroxybutane.
15. The method for producing a polyester polyol according to claim 9 ,
wherein a content of a nitrogen atom compound in the diol is from 0.1 to 50 ppm by mass in terms of nitrogen atom.
16. The method for producing a polyester polyol according to claim 9 , further comprising prior to said performing reaction subjecting a biomass resource to a fermentation process wherein said fermentation process comprises pretreating said biomass resource and further subjecting the biomass resource to saccharification.
17. A method for producing a polyurethane, comprising:
reacting a polyester polyol produced by the production method of a polyester polyol according to claim 9 with an isocyanate compound.
18. A method for producing a polyurethane, comprising:
reacting a polyester polyol and an isocyanate compound,
wherein the polyester polyol is produced by an esterification and/or transesterification reaction of a dicarboxylic acid and a diol, wherein the diol is produced directly from a biomass-resource-derived substance by a fermentation process and a content of a cyclic carbonyl compound having a carbon atom number of 5 or 6 in the diol is from 0.01 ppm to 12 ppm by mass, and
wherein said diol produced directly from a biomass-resource-derived substance by a fermentation process is selected from the group consisting of ethylene glycol, 2-methyl-1,3-propanediol, neopentyl glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, and isosorbide.
19. The method for producing a polyurethane according to claim 18 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (I):
wherein in formula (I), each of R 1 to R 4 independently represents a hydrogen atom, a methyl group, a formyl group or an acetyl group, with the proviso that one of R 1 to R 4 is a formyl group or an acetyl group, and the total number of carbon atoms contained in respective groups of R 1 to R 4 is 2 or less.
20. The method for producing a polyurethane according to claim 18 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (II):
wherein in formula (II), X represents a carbon atom or an oxygen atom, with the proviso that 1 X is an oxygen atom, each of R 5 to R 9 independently represents a methyl group or a hydrogen atom, and the total number of carbon atoms contained in respective groups of R 5 to R 9 is 1 or less.
21. The method for producing a polyurethane according to claim 18 ,
wherein the cyclic carbonyl compound having a carbon atom number of 5 or 6 contains a compound having a structure represented by the following formula (III) and a content of the compound having a structure represented by formula (III) in the diol is 6 ppm by mass or less:
wherein in formula (III), each of R 10 to R 13 independently represents a methyl group or a hydrogen atom, and the total number of carbon atoms contained in respective groups of R 10 to R 13 is 1 or less.
22. The method for producing a polyurethane according to claim 18 ,
wherein the diol is 1,4-butanediol, and
the polyester polyol is polybutylene adipate.
23. The method for producing a polyurethane according to claim 22 ,
wherein the 1,4-butanediol contains from 1 to 99 ppm by mass of 1-acetoxy-4-hydroxybutane.
24. The method for producing a polyurethane according to claim 18 ,
wherein a content of a nitrogen atom compound in the diol is from 0.1 to 50 ppm by mass in terms of nitrogen atom.
25. The method for producing a polyurethane according to claim 18 , further comprising prior to said reacting a polyester polyol and an isocyanate compound, subjecting a biomass resource to a fermentation process wherein said fermentation process comprises pretreating said biomass resource and further subjecting the biomass resource to saccharification to produce said diol.