Biomass-resource-derived polyurethane, method for producing same, and biomass-resource-derived polyester polyol

Patent metadata

Field	Value
Publication number	US-9963537-B2
Application number	US-201615174069-A
Country	US
Kind code	B2
Filing date	Jun 6, 2016
Priority date	Mar 31, 2010
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

The invention relates to a method for producing a biomass-resource-derived polyurethane, which comprises: reacting a dicarboxylic acid and an aliphatic diol to produce a polyester polyol; and reacting the polyester polyol and a polyisocyanate compound, wherein the dicarboxylic acid contains at least one component derived from biomass resources, a content of an organic acid in the dicarboxylic acid is more than 0 ppm and not more than 1,000 ppm relative to the dicarboxylic acid, and a pKa value of the organic acid at 25° C. is not more than 3.7.

First claim

The invention claimed is:

1. A biomass-resource-derived polyurethane, comprising, in reacted form:
a polyester polyol unit having a number average molecular weight of 500 to 4,500, calculated in terms of a hydroxyl number, and comprising, in reacted form:
an organic acid unit having a pKa value at 25° C. of not more than 3.7;
a dicarboxylic acid unit other than the organic acid unit having a pKa value at 25° C. of not more than 3.7; and
an aliphatic diol unit; and

a polyisocyanate unit,
wherein the dicarboxylic acid unit comprises at least one component derived from biomass resources, and a content of the organic acid unit is more than 0% by mole and not more than 0.09% by mole relative to the dicarboxylic acid unit.

2. The biomass-resource-derived polyurethane according to claim 1 , wherein the dicarboxylic acid comprises succinic acid derived from biomass resources.

3. The biomass-resource-derived polyurethane according to claim 1 , wherein a content of the dicarboxylic acid unit derived from biomass resources is 20% by mole or more relative to whole dicarboxylic acid unit.

4. The biomass-resource-derived polyurethane according to claim 2 , wherein a content of the dicarboxylic acid unit derived from biomass resources is 20% by mole or more relative to whole dicarboxylic acid unit.

5. The biomass-resource-derived polyurethane according to claim 1 , wherein at least one component of the dicarboxylic acid is an aliphatic dicarboxylic acid.

6. The biomass-resource-derived polyurethane according to claim 5 , wherein the dicarboxylic acid comprises 50% by mole or more of an aliphatic dicarboxylic acid.

7. The biomass-resource-derived polyurethane according to claim 5 , wherein the aliphatic dicarboxylic acid comprises any one of adipic acid, succinic acid, or sebacic acid.

8. The biomass-resource-derived polyurethane according to claim 6 , wherein the aliphatic dicarboxylic acid comprises any one of adipic acid, succinic acid, or sebacic acid.

9. The biomass-resource-derived polyurethane according to claim 1 , wherein the aliphatic diol unit comprises at least one of an ethylene glycol unit or a 1,4-butanediol unit.

10. The biomass-resource-derived polyurethane according to claim 1 , having a YI value (in conformity with JIS-K7105) of not more than 20.

11. The biomass-resource-derived polyurethane according to claim 1 , having a molecular weight distribution (Mw/Mn) by the GPC measurement of from 1.5 to 3.5.

12. An artificial leather comprising the biomass-resource-derived polyurethane according to claim 1 .

13. A shoe sole comprising the biomass-resource-derived polyurethane according to claim 1 .

14. The biomass-resource-derived polyurethane according to claim 1 , wherein the polyester polyol unit has a number average molecular weight of 500 to 4,000.

15. A synthetic leather comprising the biomass-resource-derived polyurethane according to claim 1 .

16. A shoe comprising the shoe sole of claim 13 .

17. A shoe comprising the artificial leather of claim 12 .

18. A shoe comprising the synthetic leather of claim 15 .

19. A bag comprising the artificial leather of claim 12 .

20. A bag comprising the synthetic leather of claim 15 .

21. A film comprising the biomass-resource-derived polyurethane according to claim 1 .

22. A coating material comprising the biomass-resource-derived polyurethane according to claim 1 .

23. An adhesive comprising the biomass-resource-derived polyurethane according to claim 1 .

24. A foam comprising the biomass-resource-derived polyurethane according to claim 1 .

25. An elastomer comprising the biomass-resource-derived polyurethane according to claim 1 .

26. The elastomer according to claim 25 , wherein the elastomer is a thermoplastic elastomer.

Assignees

• Mitsubishi Chem Corp

Inventors

• Ohara Teruhiko
• Suzuki Naoki
• Nakajima Yasuko
• Itou Hiroto
• Aoshima Takayuki
• Sugai Naoki
• Matsumoto Takanao

Classifications

• C08G63/16

  Dicarboxylic acids and dihydroxy compounds · CPC title

• A43B13/04

  Plastics, rubber or vulcanised fibre · CPC title

• C08G18/4241

  from dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional · CPC title

• C08G63/60

  derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds · CPC title

• C08G2410/00

  Soles · CPC title