Polyurethane resin composition, polyurethane resin, molded article, fiber reinforced plastic, and method for producing fiber reinforced plastic

Patent metadata

Field	Value
Publication number	US-11319403-B2
Application number	US-201816758170-A
Country	US
Kind code	B2
Filing date	Nov 7, 2018
Priority date	Nov 13, 2017
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

The polyurethane resin composition contains, a polyisocyanate component containing p-MDI, a polyol component, an organic metal catalyst, and a reaction retardant represented by general formula (1) below, wherein the mole ratio of the reaction retardant relative to 1 mol of the organic metal catalyst is 0.50 or more and 2.50 or less. (in general formula (1), A represents an aliphatic ring or an aromatic ring, R1 represents a hydrocarbon group composing ring A, R2 represents an aliphatic hydrocarbon group bonded to ring A. R3 represents a hydrogen atom or alkyl group bonded to nitrogen atom included in ring A. R1 represents a hydrogen atom or carboxyl group bonded to ring A. m is 1 or 2, n is 0 or 1, and total of n and no is 2 or less.)

First claim

The invention claimed is:

1. A polyurethane resin composition comprising:
a polyisocyanate component containing polyphenylmethane polyisocyanate,
a polyol component,
an organic metal catalyst, and
a reaction retardant represented by general formula (1), general formula (2), general formula (3), general formula (4), or general formula (5) below, wherein
the mole ratio of the reaction retardant relative to 1 mol of the organic metal catalyst is 0.50 or more and 2.50 or less,

in general formula (1), A represents an aliphatic ring or aromatic ring, R 1 represents a hydrocarbon group included in ring A and having 1 carbon atom, R 2 represents an aliphatic hydrocarbon group having 1 carbon atom, R 3 represents a hydrogen atom or alkyl group bonded to nitrogen atom included in ring A when ring A is an aliphatic ring, and represents a hydrogen atom when ring A is an aromatic ring, R 4 represents a hydrogen atom or carboxyl group bonded to ring A, m is 1, n is 0 or 1, and —COOH is bonded to ring A through R 2 bonded to R 1 at a position of ring A when n is 1, and is bonded directly to R 1 at a position of ring A when n is 0;

in general formula (2), A represents an aliphatic ring or aromatic ring, R 2 is the same as R 2 in general formula (1), R 3 represents a hydrogen atom or alkyl group bonded to nitrogen atom included in ring A when ring A is an aliphatic ring, R 3 does not exist when ring A is an aromatic ring, n is 0, and —COOH is bonded directly to ring A;

2. The polyurethane resin composition according to claim 1 , wherein
the reaction retardant is picolinic acid.

3. The polyurethane resin composition according to claim 1 , wherein
the reaction retardant content relative to 100 parts by mass of the polyol component is 0.05 parts by mass or more and 1.4 parts by mass or less.

4. The polyurethane resin composition according to claim 1 , wherein
the organic metal catalyst includes potassium salt.

5. The polyurethane resin composition according to claim 1 , wherein
the organic metal catalyst content relative to 100 parts by mass of the polyol component is 0.001 parts by mass or more and 10 parts by mass or less.

6. The polyurethane resin composition according to claim 1 , wherein
the polyisocyanate component further contains alicyclic polyisocyanate,
and in the polyisocyanate component, the ratio of the alicyclic polyisocyanate-derived isocyanate group relative to a total amount of the polyphenylmethane polyisocyanate-derived isocyanate group and the alicyclic polyisocyanate-derived isocyanate group is 10 mol % or more and 70 mol % or less.

7. The polyurethane resin composition according to claim 1 , wherein
setting a total of the hydroxyl group of the polyol component as 100, the ratio of a total of the isocyanate group of the polyisocyanate component relative to a total of the hydroxyl group of the polyol component is 75 or more and 400 or less.

8. Polyurethane resin comprising a cured product of the polyurethane resin composition according to claim 1 .

9. A molded article including the polyurethane resin according to claim 8 .

10. Fiber reinforced plastic comprising:
fiber, and
a cured product of the polyurethane resin composition according to claim 1 , wherein the fiber is impregnated with the polyurethane resin composition.

11. The fiber reinforced plastic according to claim 10 , wherein
the fiber comprises at least one selected from the group consisting of carbon fiber, glass fiber, and aramid fiber.

12. A method for producing the fiber reinforced plastic according to claim 10 , wherein
the fiber reinforced plastic is produced by a molding method selected from the group consisting of Resin Transfer Molding method, High-Pressure Resin Transfer Molding method, Wet Compression Molding method, and Reaction Injection Molding method.

13. The method for producing fiber reinforced plastic according to claim 12 , wherein
the molding temperature in the molding method is 25° C. or more and 250° C. or less.

14. The method for producing fiber reinforced plastic according to claim 12 , wherein
the molding time for the molding method is 10 seconds or more and 5 minutes or less.

15. The polyurethane resin composition according to claim 1 , wherein
in formulae (1) and (2), the alkyl group represented as R 3 has 1 to 12 carbon atoms.

16. The polyurethane resin composition according to claim 1 , wherein
in formulae (1) and (2), the alkyl group represented as R 3 has 1 to 4 carbon atoms.

Assignees

• Mitsui Chemicals Inc

Inventors

• Tanaka Toshihiro
• Kanayama Hiroshi
• Watanabe Minoru
• Inoue Hiroki
• Saito Junji

Classifications

• C08G18/797

  containing carbodiimide and/or uretone-imine groups · CPC title

• C08G18/7657 Primary

  containing two or more aromatic rings · CPC title

• C08J5/046

  with synthetic macromolecular fibrous material · CPC title

• C08G18/7664 Primary

  containing alkylene polyphenyl groups · CPC title

• C08G18/724

  Combination of aromatic polyisocyanates with (cyclo)aliphatic polyisocyanates · CPC title