Polycarbonate diol and polyurethane using same

Patent metadata

Field	Value
Publication number	US-2015291724-A1
Application number	US-201514751898-A
Country	US
Kind code	A1
Filing date	Jun 26, 2015
Priority date	Dec 26, 2012
Publication date	Oct 15, 2015
Grant date	—

Abstract

The present invention relates to a polycarbonate diol comprising a structural unit derived from a compound represented by the following formula (A) and a structural unit derived from a compound represented by the following formula (B), wherein the hydroxyl value is from 20 to 450 mg-KOH/g:
HO—R 1 —OH  (A)

HO—R 2 —OH  (B)
the glass transition temperature of said polycarbonate diol as measured by a differential operating calorimeter is −30° C. or less and the average carbon number of a dihydroxy compound obtained by hydrolyzing said polycarbonate diol is from 3 to 5.5.

First claim

1 . A polycarbonate diol comprising a structural unit derived from a compound represented by the following formula (A) and a structural unit derived from a compound represented by the following formula (B), wherein the hydroxyl value is from 20 to 450 mg-KOH/g:
HO—R 1 —OH  (A)
HO—R 2 —OH  (B)
wherein in formula (A), R 1 represents a substituted or unsubstituted divalent alkylene group having a carbon number of 3 to 5, and in formula (B), R 2 represents a substituted or unsubstituted divalent alkylene group having a carbon number of 8 to 20.

2 . The polycarbonate diol as claimed in claim 1 , wherein the ratio of the total of a structural unit derived from said compound represented by formula (A) and a structural unit derived from said compound represented by formula (B) to all structural units in said polycarbonate diol is 50 mol % or more.

3 . The polycarbonate diol as claimed in claim 1 , wherein the ratio between a structural unit derived from said compound represented by formula (A) and a structural unit derived from said compound represented by formula (B) is from 50:50 to 99:1 in terms of molar ratio.

4 . The polycarbonate diol as claimed in claim 1 , wherein the average carbon number of a dihydroxy compound obtained by hydrolyzing said polycarbonate diol is from 4 to 5.5.

5 . The polycarbonate diol as claimed in claim 1 , wherein said hydroxyl value is from 20 to 60 mg-KOH/g.

6 . The polycarbonate diol as claimed in claim 1 , wherein said compound represented by formula (A) is at least one compound selected from the group consisting of 1,3-propanediol and 1,4-butanediol.

7 . The polycarbonate diol as claimed in claim 1 wherein said compound represented by formula (B) is at least one compound selected from the group consisting of 2-methyl-1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol and 1,12-dodecanediol.

8 . The polycarbonate diol as claimed in claim 1 , wherein at least either of said compound represented by formula (A) and said compound represented by formula (B) is plant-derived.

9 . A polyurethane formed using the polycarbonate diol claimed in claim 1 .

10 . An artificial leather, synthetic leather, a coating material, a coating agent, an aqueous polyurethane coating material, an aqueous polyurethane coating material, a pressure sensitive adhesive or adhesive produced using the polyurethane claimed in claim 9 .

11 . An active energy ray-curable polymer composition formed using the polycarbonate diol claimed in claim 1 .

12 . A method for producing the polycarbonate diol claimed in claim 1 , comprising performing polycondensation through a transesterification reaction using a compound represented by the following formula (A), a compound represented by the following formula (B), and a carbonate compound to produce a polycarbonate diol:
HO—R 1 —OH  (A)
HO—R 2 —OH  (B)
wherein in formula (A), R 1 represents a substituted or unsubstituted divalent alkylene group having a carbon number of 3 to 5, and in formula (B), R 2 represents a substituted or unsubstituted divalent alkylene group having a carbon number of 8 to 20.

13 . A polycarbonate diol having a hydroxyl value of 20 to 45 mg-KOH/g, wherein the glass transition temperature of said polycarbonate diol as measured by a differential operating calorimeter is −30° C. or less and the average carbon number of a dihydroxy compound obtained by hydrolyzing said polycarbonate diol is from 3 to 5.5.

14 . The polycarbonate diol as claimed in claim 13 , wherein said dihydroxy compound is only an aliphatic dihydroxy compound having no substituent.

15 . The polycarbonate diol as claimed in claim 13 , wherein said dihydroxy compound contains at least one member selected from the group consisting of 1,3-propanediol, 1,4-butanediol and 1,5-pentanediol.

16 . The polycarbonate diol as claimed in claim 13 , wherein the melting heat quantity at a melting peak measured by a differential operating calorimeter is from 5.0 to 80 J/g.

17 . The polycarbonate diol as claimed in claim 13 , wherein said dihydroxy compound contains a plant-derived compound.

18 . A method for producing the polycarbonate diol claimed in claim 13 , comprising performing a transesterification of one kind or multiple kinds of dihydroxy compounds having an average carbon number of 3 to 5.5 with a diaryl carbonate in the presence of a transesterification catalyst to produce a polycarbonate diol.

19 . The production method of a polycarbonate diol as claimed in claim 18 , wherein said one kind or multiple kinds of dihydroxy compounds contain a plant-derived compound.

20 . The production method of a polycarbonate diol as claimed in claim 18 , wherein said transesterification catalyst is a compound of at least one element selected from the group consisting of Group 1 elements in the long-period periodic table (excluding hydrogen) and Group 2 elements in the long-period periodic table.

21 . A polyurethane comprising the polycarbonate diol claimed in claim 13 .

Assignees

• Mitsubishi Chem Corp

Inventors

• Kusano Kazunao
• Kanamori Yoshikazu
• Nakagawa Yoko
• Yano Kaori

Classifications

• C08G18/44 Primary

  Polycarbonates · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C09J175/06

  from polyesters · CPC title

• C09J175/04

  Polyurethanes · CPC title

• C08G64/305

  and alcohols · CPC title