Polyurethane chain extender, composition for forming polyurethane resin, polyurethane resin, polyurethane resin composition, molded body, and article

Patent metadata

Field	Value
Publication number	US-12281192-B2
Application number	US-202218708095-A
Country	US
Kind code	B2
Filing date	Nov 4, 2022
Priority date	Nov 15, 2021
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

Abstract

A polyurethane chain extender includes an amine compound (X) represented by Formula (1) with a trans-isomer proportion in (X) of 50 mol % or more; a composition for forming a polyurethane-based resin including the polyurethane chain extender; a polyurethane-based resin formed by the composition for forming the polyurethane-based resin; a polyurethane-based resin obtained by reacting a polyisocyanate compound (A), a polyol compound (B) and the polyurethane chain extender; a polyurethane-based resin composition including the polyurethane-based resin; a molded body obtained by molding the polyurethane-based resin composition; and an article including the polyurethane-based resin composition or the molded body:

where R 1 to R 12 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less of carbon atoms, p and q each independently represent an integer of 0 or more and 4 or less, and at least one of p and q is 1 or more.

First claim

The invention claimed is:

1. A composition for forming a polyurethane-based resin, comprising a polyisocyanate compound (A), a polyol compound (B), and a polyurethane chain extender (C) comprising an amine compound (X) represented by the following Formula (1),
wherein a proportion of a trans-isomer in the amine compound (X) is 50 mol % or more:

where in the above Formula (1), R 1 to R 12 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less of carbon atoms, p and q each independently represent an integer of 0 or more and 4 or less, and at least one of p or q is 1 or more.

2. The composition of claim 1 , wherein the amine compound (X) comprises a 1,4-bis (aminomethyl) cyclohexane.

3. The composition according to claim 1 , wherein the proportion of a trans-isomer in the amine compound (X) is 100 mol % or less.

4. A polyurethane-based resin formed from the composition for forming the polyurethane-based resin described in claim 1 .

5. The polyurethane-based resin according to claim 4 , wherein a ratio of the number of active hydrogen groups in the polyurethane chain extender (C) to a total amount of the number of active hydrogen groups in the polyol compound (B) and the number of active hydrogen groups in the polyurethane chain extender (C) is 0.01 or more and 0.5 or less.

6. The polyurethane-based resin according to claim 4 , wherein a ratio of the number of isocyanate groups in the polyisocyanate compound (A) to a total amount of the number of active hydrogen groups in the polyol compound (B) and the number of active hydrogen groups in the polyurethane chain extender (C) is 0.5 or more and 1.5 or less.

7. The polyurethane-based resin according to claim 4 , wherein a tensile strength of the polyurethane-based resin measured in accordance with JIS K 6251:2017 under conditions of a tensile speed of 200 mm/min and a chuck-to-chuck distance of 50 mm is 1.0 MPa or more.

8. The polyurethane-based resin according to claim 4 , wherein a tensile elastic modulus of the polyurethane-based resin measured in accordance with JIS K 6251:2017 under conditions of a tensile speed of 200 mm/min and a chuck-to-chuck distance of 50 mm is 2.5 MPa or more.

9. The polyurethane-based resin according to claim 4 , wherein a Shore A hardness of the polyurethane-based resin measured in accordance with JIS K 6253:2012 is 50 or more.

10. The polyurethane-based resin according to claim 4 , which is a polyurethane-urea resin.

11. A polyurethane-based resin composition, comprising the polyurethane-based resin described in claim 4 .

12. A molded body formed by molding the polyurethane-based resin composition described in claim 11 .

13. An article, comprising the polyurethane-based resin composition described in claim 11 .

14. An article, comprising the molded body described in claim 12 .

15. A composition for forming a polyurethane-based resin, comprising: an isocyanate group-terminated prepolymer obtained by reacting a polyisocyanate compound (A) with a polyol compound (B); and a polyurethane chain extender (C) comprising an amine compound (X) represented by the following Formula (1),
wherein a proportion of a trans-isomer in the amine compound (X) is 50 mol % or more:

where in the above Formula (1), R 1 to R 12 each independently represent a hydrogen atom or a hydrocarbon group having 1 or more and 4 or less of carbon atoms, p and q each independently represent an integer of 0 or more and 4 or less, and at least one of p or q is 1 or more.

16. A polyurethane-based resin formed from the composition for forming the polyurethane-based resin described in claim 15 .

17. A polyurethane-based resin composition, comprising the polyurethane-based resin described in claim 16 .

18. An article, comprising the polyurethane-based resin composition described in claim 17 .

19. An article comprising the polyurethane-based resin composition described in claim 17 .

20. The article of claim 18 which is in the form of a molded body.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• OHNO Yuma
• Akai Yuka
• Hanaoka Takuma
• Ikeuchi Kousuke
• Kouno Kazuki

Classifications

• C08G18/246

  containing also tin-carbon bonds · CPC title

• C08G18/755 Primary

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08L75/02

  Polyureas · CPC title

• C08G18/6685

  with compounds of group C08G18/3225 or polyamines of C08G18/38 · CPC title

• C08G18/4854

  Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group · CPC title