(IO)  Patent No.:  US  10,619,000 B2  Apr. 14, 2020  (45)  Date of Patent:  c12)  United States Patent  Ohara et al.  (54)  BIOMASS-RESOURCE-DERIVED  POLYURETHANE, METHOD FOR  PRODUCING SAME, AND  BIOMASS-RESOURCE-DERIVED  POLYESTER POLYOL  USO 10619000B2  (2013.01);  C08G 18114  (2013.01);  C08G  1814241  (2013.01);  C08G 1814286  (2013.01);  C08G 181664  (2013.01);  C08G 1817657  (2013.01);  C08G 1817671  (2013.01);  C08G  63/06  (2013.01);  C08G 63/16  (2013.01);  C08G 63/20  (2013.01);  C08G 63/60  (2013.01);  C09D 175106  (2013.01);  C09J  175106  (2013.01);  C08G 2101/0008  (2013.01);  C08G 2410/00  (2013.01)  (58)  Field of Classification Search  CPC ................ C08G 18/4238; C08G 63/60; C08G  18/4286; C08G 18/4241; C08G 18/7671;  C08G 18/7657; C08G 18/664; C08G  63/16; C08G 63/20; C08G 63/06; C08G  18/14; C08G 2101/0008; C08G 2410/00;  C09J 175/06; A43B 13/04; A43B 1/14;  A43B 1/00; C09D 175/06; C07C 69/70;  C07C 69/704; C07C 69/675; C07C 69/66;  C07C 69/34; C07C 69/40; C07C 59/245  See application file for complete search history.  (71)  Applicant:  Mitsubishi Chemical Corporation,  Chiyoda-ku (JP)  (72)  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)  (73)  Assignee:  Mitsubishi Chemical Corporation,  Chiyoda-ku (JP)  ( * )  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  (21)  Appl. No.:  16/413,862  (22)  Filed:  May 16, 2019  (65)  Prior Publication Data  Related U.S. Application Data  (63)  Continuation of application No. 15/936,535, filed on  Mar. 27, 2018, now Pat. No. 10,351,658, which is a  (Continued)  US 2019/0263960 Al  Aug. 29, 2019  (30)  Foreign Application Priority Data  Mar. 31, 2010  (JP) ................................. 2010-082393  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ............  C08G 1814238  (2013.01);  A43B 1100  (2013.01);  A43B 1114  (2013.01);  A43B 13/04  (2013.01);  C07C 591245  (2013.01);  C07C  69/34  (2013.01);  C07C 69/40  (2013.01);  C07C  69/66  (2013.01);  C07C 691675  (2013.01);  C07C 69170  (2013.01);  C07C 691704  C08G 18142  C07C 69/34  C07C 69/40  C07C 69/66  C07C 691675  C07C 69170  C07C 691704  C08G 63/06  C08G 63/20  C08G 63/60  C08G 18108  A63B 1100  C09J  175106  C09D  175106  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (Continued)  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (Continued)  (Continued)  (Continued)  Office Action dated Dec. 29, 2017, in Chinese Patent Application  No. 201510387263.7 filed Mar. 30, 2011 (with English translation).  Primary Examiner  - Rabon A Sergent  (74)  Attorney, Agent, or Firm  - Obion, McClelland,  Maier & Neustadt, L.L.P.  The invention relates to a method for producing a biomass› resource-derived polyurethane, which comprises: reacting a  dicarboxylic acid and an aliphatic dial to produce a polyester  polyol; and reacting the polyester polyol and a polyisocya› nate 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  O  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.  4 Claims, No Drawings  Specification includes a Sequence Listing.  (57)  ABSTRACT  5,436,056 A  5,688,890 A  7/1995 Takiyama et al.  ll/ 1997 Ishiguro et al.  CN  EP  101215371 A  7/2008  1 640 397  3/2006 