IP Library Granted Patent US 9,963,537
Granted Patent B2
US 9,963,537 · App. 15/174,069 · Granted May 8, 2018

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

Inventors: Teruhiko Ohara (Tokyo, JP); Naoki Suzuki (Niigata, JP); Yasuko Nakajima (Kanagawa, JP); Hiroto Itou (Mie, JP); Takayuki Aoshima (Kanagawa, JP); Naoki Sugai (Kanagawa, JP); Takanao Matsumoto (Kanagawa, JP)
Assignee: MITSUBISHI CHEMICAL CORPORATION
C08G18/4238A43B1/00A43B1/14A43B13/04C07C59/245C07C69/34C07C69/40C07C69/66C07C69/675C07C69/70C07C69/704C08G18/14C08G18/4241C08G18/4286C08G18/664C08G18/7657C08G18/7671C08G63/06C08G63/16C08G63/20C08G63/60C09D175/06C09J175/06C08G2101/0008C08G2410/00
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Quick Facts
Patent No.
US 9,963,537
App. No.
15/174,069
Granted
May 8, 2018
Kind
B2
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.

Claims (32)

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.

Assignments (2)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
MERGER Recorded Sep 4, 2017
From: MITSUBISHI CHEMICAL CORPORATION
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 043750/0207 →
Priority Claims (1)
JP 2010-082393 · Mar 31, 2010 · national
Continuity (3)
Continuation 13632992 · Oct 1, 2012
Continuation PCTJP2011057984 · Mar 30, 2011
Related Publication 20160272751A1 · Sep 22, 2016