IP Library Granted Patent US 10,316,130
Granted Patent B2
US 10,316,130 · App. 14/751,898 · Granted Jun 11, 2019

Polycarbonate diol and polyurethane using same

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Quick Facts
Patent No.
US 10,316,130
App. No.
14/751,898
Granted
Jun 11, 2019
Kind
B2
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.

Claims (22)

1. A polycarbonate diol having a hydroxyl value of 20 to 42 mg-KOH/g, wherein:

the glass transition temperature of said polycarbonate diol as measured by a differential scanning calorimeter is −30° C. or less;

an average carbon number of all dihydroxy compounds obtained by hydrolyzing said polycarbonate diol is from 3 to 5.5;

the polycarbonate diol does not contain a structural unit derived from 1,6-hexanediol; and

a ratio of weight average molecular weight/number average molecular weight (Mw/Mn) of said polycarbonate diol ranges from 1.5 to 3.0.

2. The polycarbonate diol as claimed in claim 1 , wherein said dihydroxy compounds consist of an aliphatic dihydroxy compound having no substituent.

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

4. The polycarbonate diol as claimed in claim 1 , wherein the melting heat quantity of the polycarbonate diol at a melting peak measured by a differential scanning calorimeter is from 5.0 to 80 J/g.

5. The polycarbonate diol as claimed in claim 1 , wherein said dihydroxy compounds comprise a plant-derived compound.

6. A method for producing the polycarbonate diol of claim 1 , the method comprising transesterifying at least one dihydroxy compound having an average carbon number of 3 to 5.5 with a diaryl carbonate in the presence of a transesterification catalyst to produce the polycarbonate diol.

7. The method of claim 6 , wherein the at least one dihydroxy compound comprises a plant-derived compound.

8. The method of claim 6 , wherein said transesterification catalyst is a compound comprising at least one element selected from the group consisting of a Group 1 element in the long-period periodic table (excluding hydrogen) and a Group 2 element in the long-period periodic table.

9. A polyurethane, comprising the polycarbonate diol of claim 1 .

10. The polycarbonate diol according to claim 1 , comprising a structural unit derived from a compound represented by formula (A) and a structural unit derived from a compound represented by formula (B):

HO—R 1 —OH  (A)

HO—R 2 —OH  (B)

wherein:

R 1 represents a divalent alkylene group comprising a main chain having a carbon number of 3 to 5; and

R 2 represents a divalent alkylene group comprising a main chain having a carbon number of 8 to 20.

11. The polycarbonate diol according to claim 1 , wherein the average carbon number of the dihydroxy compounds obtained by the hydrolyzing of the polycarbonate diol is from 4.3 to 5.5.

12. The polycarbonate diol according to claim 1 , wherein the average carbon number of the dihydroxy compounds obtained by the hydrolyzing of the polycarbonate diol is from 3 to 5.0.

13. The polycarbonate diol according to claim 1 , wherein the ratio of weight average molecular weight/number average molecular weight (Mw/Mn) of said polycarbonate diol ranges from 1.7 to 3.0.

Assignments (3)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 26, 2015
From: KUSANO, KAZUNAO; KANAMORI, YOSHIKAZU; NAKAGAWA, YOKO; YANO, KAORI
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 035915/0870 →
Cited By (1)
US 12,570,785