Polyurethane resin

• US 8,722,752 B2
• Filed: 10/14/2008
• Issued: 05/13/2014
• Est. Priority Date: 10/15/2007
• Status: Active Grant

• Current Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Original Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Inventors: Kuwamura, Goro, Yamasaki, Satoshi, Nakagawa, Toshihiko, Hasegawa, Daisuke
• Primary Examiner(s): Gulakowski, Randy
• Assistant Examiner(s): WASHVILLE, JEFFREY D
• Application Number:
  US12/682,714
• Publication Number:
  US 20100216905A1
• Time in Patent Office: 2,037 Days
• US Class Current: 521/170
• CPC Class Codes: B29C 41/18 Slush casting, i.e. pouring moulding material into a hollow mould with excess material being poured off
• CPC Class Codes: B60R 13/02 Internal Trim mouldings ; Internal Ledges; Wall liners for passenger compartments; Roof liners B60R13/01 takes precedence ; padded linings for the vehicle interior B60R21/04; arrangements or adaptations of floor mats or carpets in vehicles B60N3/04; internal lining for trains B61D17/18
• CPC Class Codes: C08G 18/0823 containing carboxylate salt groups or groups forming them
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/14 Manufacture of cellular products
• CPC Class Codes: C08G 18/163 covered by C08G18/18 and C08G18/22
• CPC Class Codes: C08G 18/2825 having at least 6 carbon atoms
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/3225 Polyamines
• CPC Class Codes: C08G 18/3228 acyclic
• CPC Class Codes: C08G 18/3231 Hydrazine or derivatives thereof
• CPC Class Codes: C08G 18/341 Dicarboxylic acids, esters of polycarboxylic acids containing two carboxylic acid groups
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/4018 Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/6225 Polymers of esters of acrylic or methacrylic acid
• CPC Class Codes: C08G 18/6659 with compounds of group C08G18/34
• CPC Class Codes: C08G 18/6674 with compounds of group C08G18/3203
• CPC Class Codes: C08G 18/6688 with compounds of group C08G18/3271
• CPC Class Codes: C08G 18/722 : Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
• CPC Class Codes: C08G 18/757 : containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
• CPC Class Codes: C08G 18/758 : containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 18/7837 : containing allophanate groups
• CPC Class Codes: C08G 18/792 : formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08G 2110/005 : < 50kg/m3
• CPC Class Codes: C08G 2110/0083 : prepared using water as the sole blowing agent
• CPC Class Codes: C08G 2120/00 : Compositions for reaction injection moulding processes
• CPC Class Codes: C08J 2375/08 : from polyethers
• CPC Class Codes: C08J 5/18 : Manufacture of films or sheets
• CPC Class Codes: C08J 9/00 : Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof mechanical aspects of shaping of plastics or substances in a plastic state for the production of porous or cellular articles B29C
• CPC Class Codes: C08J 9/125 : Water, e.g. hydrated salts
• CPC Class Codes: C08K 3/20 : Oxides; Hydroxides graphene oxides C08K3/042
• CPC Class Codes: C08L 75/00 : Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 175/08 : from polyethers
• CPC Class Codes: C09D 175/14 : Polyurethanes having carbon-to-carbon unsaturated bonds
• CPC Class Codes: D01F 6/70 : from polyurethanes
• CPC Class Codes: G02B 1/041 : Lenses

Abstract

Disclosed is a polyurethane resin which is obtained by a reaction between a polyisocyanate component, which contains 1,4-bis(isocyanatomethyl)cyclohexane including not less than 80% by mole of trans isomers, and an active hydrogen compound component.

Claims

1. A polyurethane resin obtained by a reaction between a polyisocyanate component comprising

polyisocyanate component consisting of 1,4-bis(isoeyanatomethyl)cyclohexane consisting of 80-93% by mole of trans isomers and the remaining 7-20% by mole of cis isomers, wherein the cis and the trans isomers equal 100% by mole, and

an active hydrogen compound component,

wherein the active hydrogen compound component comprises at least one component selected from the group consisting of:

a polyol component having two or more hydroxyl groups, a polythiol component having two or more mercapto groups, and a polyamine component having two or more amino groups.

2. The polyurethane resin according to claim 1, wherein the 1,4-bis(isocyanatomethyl)cyclohexane comprises 80-86% by mole of trans isomers.

3. The polyurethane resin according to claim 1, being a molding resin.

4. The polyurethane resin according to claim 1, being an optical polyurethane resin.

5. The polyurethane resin according to claim 4, wherein the active hydrogen compound component is a polyol component having a hydroxyl value of 280 to 1240 mg KOH/g and an average functionality of more than 2 and less than 5.

9. The polyurethane resin according to claim 1, being a granular polyurethane resin.

10. The polyurethane resin according to claim 9, being used for slush molding.

11. A slush molded article, being obtained by slush molding of the polyurethane resin as defined in claim 9.

12. The polyurethane resin according to claim 1, being a polyurethane resin for elastic molding.

13. An elastic molded article using the polyurethane resin as defined in claim 12.

14. The polyurethane resin according to claim 1,

wherein the polyisocyanate component further comprises a polyisocyanate other than the 1,4-bis(isocyanatomethyl)cyclohexane including 80-93% by mole of trans isomers), which is an isocyanurate-modified product of at least either one of alicyclic polyisocyanate and aralkyl polyisocyanate, and

the polyurethane resin is a polyurethane resin for reaction injection molding.

15. The polyurethane resin according to claim 14, wherein

the alicyclic polyisocyanate and the aralkyl polyisocyanate are at least one kind selected from the group consisting of 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane,2,5-di(isocyanatomethyl)bicyclo[2,2,1]heptane, 2,6-di(isocyanatomethyl)bicyclo[2,2,1]heptane, isophorone diisocyanate, 1,3-bis(isocyanatomethyl)benzene, and 1,4-bis(isocyanatomethyl)benzene.

16. A reaction injection molded article being formed from the polyurethane resin as defined in claim 14.

17. The polyurethane resin according to claim 1, wherein

the polyisocyanate component further comprises

an allophanate-modified 1,4-bis(isocyanatomethyl)cyclohexane including 80-93% by mole of trans isomers and

an isocyanurate-modified 1,4-bis(isocyanatomethyl)cyclohexane including 80-93% by mole of trans isomers

so as to have an allophanate/isoeyanurate composition ratio of 50/50 to 100/0,

to be prepared as a two-part curing polyurethane resin.

18. The polyurethane resin according to claim 1,

further comprising a foaming agent and

being obtained as a polyurethane foam by foaming and reaction.

19. The polyurethane resin according to claim 17, wherein

the active hydrogen compound component is a polyol component,

the polyol component having a hydroxyl value of 10 to 120 mg KOH/g and

a primary hydroxyl group at its molecular end of not less than 40% by mole or more.

20. The polyurethane resin according to claim 17, being used as a molded article for clothing, sanitary, or shoes.

6. A polyurethane resin obtained by a reaction between a polyisocyanate component and an active hydrogen compound component, wherein the polyisocyanate component comprises:

1,4-bis(isocyanatomethyl)cyclohexane consisting of 80-93% by mole of trans isomers and the remaining 7-20% by mole of cis isomers wherein the cis and the trans isomers equal 100% by mole and

a polyisocyanate other than the 1,4-bis(isocyanatomethyl)eyclohexane;

the active hydrogen compound component comprises;

a high-molecular-weight polyol, an active hydrogen compound comprising a hydrophilic group and a chain extender; and

first, the polyisocyanate component is allowed to react with the high-molecular-weight polyol and the active hydrogen compound comprising a hydrophilic group to prepare an isocyanate group-terminated prepolymer, and

subsequently, the isocyanate group-terminated prepolymer and the chain extender are allowed to react to thereby obtain an aqueous polyurethane resin.

7. A film, being made of the polyurethane resin as defined in claim 6.

8. Artificial and synthetic leather, using the polyurethane resin as defined in claim 6.