Self-crosslinkable polyhydroxy polyurethane resin, resinaceous material that contains the resin, process for production of the resin, and imitation leather, surfacing material and weatherstrip material, using the resin

Patent metadata

Field	Value
Publication number	US-10066048-B2
Application number	US-201113805970-A
Country	US
Kind code	B2
Filing date	Jun 21, 2011
Priority date	Jun 24, 2010
Publication date	Sep 4, 2018
Grant date	Sep 4, 2018

Abstract

Provided are a self-crosslinking polyhydroxy polyurethane resin derived from a reaction of a 5-membered cyclic carbonate compound and an amine compound and having masked isocyanate groups in its structure; a process for producing the resin; an imitation leather composed of a base fabric and a resin composition composed of the resin as its principal component and impregnated in or laminated on the base fabric; as kin material made of a thermoplastic polyolefin resin, said skin material including a thermoplastic polyolefin resin sheet and a top coat layer formed directly or via a primer layer on the sheet, wherein the top coat layer has been formed with a resin composition composed of the resin as its principal component; and a weather strip material composed, as its principal components, of the resin and a specific diorganopolysiloxane and/or a silicone oil.

First claim

The invention claimed is:

1. A self-crosslinking polyhydroxy polyurethane resin,
wherein the self-crosslinking polyhydroxy polyurethane resin comprises in a structure thereof:
a polyhydroxy polyurethane consisting of a reaction product consisting of a 5-membered cyclic carbonate compound and a diamine compound as reactants, where the diamine compound is a compound selected from the group consisting of a diamine compound having only two primary amine groups as amine groups, aminoethylethanolamine, hydroxyethylaminopropylamine, and mixtures thereof;
a modifier; and
at least one masked isocyanate group,

the self-crosslinking polyhydroxy polyurethane resin consists of the polyhydroxy polyurethane having been modified with the modifier, as polyurethane, and
a modification ratio of the self-crosslinking polyhydroxy polyurethane resin modified with the modifier is in a range from 2% to 60%,
wherein the modifier has at least one free isocyanate group and the at least one masked isocyanate group before the modification of the polyhydroxy polyurethane, and
the modification ratio of the self-crosslinking polyhydroxy polyurethane resin is obtained by a following formula:
modification ratio (%)={1-(hydroxyl groups in the polyhydroxy polyurethane in the self-crosslinking polyhydroxy polyurethane resin after modification/hydroxyl groups in the polyhydroxy polyurethane before modification)}×100.

2. The self-crosslinking polyhydroxy polyurethane resin according to claim 1 ,
wherein the 5-membered cyclic carbonate compound is a reaction product of an epoxy compound and carbon dioxide, and contains, in a structure of the 5-membered cyclic carbonate compound, a —O—C(O)— group derived from the carbon dioxide in a range from 1 to 25 mass %.

3. The self-crosslinking polyhydroxy polyurethane resin according to claim 1 ,
wherein the masked isocyanate groups are reaction products of organic polyisocyanate groups and a masking agent,
the self-crosslinking polyhydroxy polyurethane resin is capable of self-crosslinking,
when the self-crosslinking polyhydroxy polyurethane resin is subjected to a heat treatment, the masked isocyanate groups are demasked and form isocyanate groups, and
the isocyanate groups react with hydroxyl groups in the structure of the self-crosslinking polyhydroxy polyurethane resin, so that the self-crosslinking polyhydroxy polyurethane resin undergoes self-crosslinking.

4. A process for producing the self-crosslinking polyhydroxy polyurethane resin according to claim 1 , the process comprising:
reacting the at least one free isocyanate group of the modifier, with hydroxyl groups in the polyhydroxy polyurethane, so as to obtain the self-crosslinking polyhydroxy polyurethane resin having been modified with the modifier and having the masked isocyanate groups in the structure thereof.

5. The process according to claim 4 ,
wherein the 5-membered cyclic carbonate compound is a reaction product of an epoxy compound and carbon dioxide, and
the carbon dioxide is contained in a range from 1 to 25 mass % in the self-crosslinking polyhydroxy polyurethane resin.

6. The process according to claim 4 , wherein the modifier is a reaction product of an organic polyisocyanate compound and a masking agent.

7. A resin material comprising:
the self-crosslinking polyhydroxy polyurethane resin according to claim 1 ; and
another binder resin blended therewith.

8. An imitation leather comprising:
a base fabric; and
a resin composition comprising, as a principal component, the self-crosslinking polyhydroxy polyurethane resin according to claim 1 , where the resin composition is impregnated in or laminated on the base fabric.

9. A skin material made of a thermoplastic polyolefin resin, comprising:
a thermoplastic polyolefin resin sheet; and
a top coat layer formed directly or via a primer layer on the sheet,
wherein the top coat layer has been formed with a resin composition comprising, as a principal component, the self-crosslinking polyhydroxy polyurethane resin according to claim 1 .

10. The skin material according to claim 9 ,
wherein the self-crosslinking polyhydroxy polyurethane resin has been obtained by modifying, with the modifier, the polyhydroxy polyurethane resin, which is derived from the reaction of the 5-membered cyclic carbonate compound and the diamine compound, which is at least one compound selected from the group consisting of a diamine compound having only two primary amine groups as amine groups, aminoethylethanolamine, and hydroxyethylaminopropylamine.

11. The skin material according to claim 9 ,
wherein the resin composition with which the top coat layer is formed further comprises a material, which comprises one fine powder or a combination of two or more fine powders selected from the group consisting of organic fine powders and inorganic fine powders, and which is added to the resin composition as a matting agent in a range from 1 to 150 parts by mass relative to 100 parts by mass of the self-crosslinking polyhydroxy polyurethane resin.

12. A weather strip material for coating and/or impregnating a high-molecular elastomer material to form a surface treatment layer at a slide contact portion that is brought into sliding contact with another part,
wherein the weather strip material is a resin composition comprising:
the self-crosslinking polyhydroxy polyurethane resin according to claim 1 ; and
a material selected from the group consisting of a diorganopolysiloxane having an average polymerization degree in a range from 5,000 to 10,000, a silicone oil having a kinematic viscosity in a range from 100 to 10,000 CS, and a mixture thereof.

13. The weather strip material according to claim 12 ,
wherein the self-crosslinking polyhydroxy polyurethane resin has been obtained by modifying, with the modifier, the polyhydroxy polyurethane derived from the reaction of the 5-membered cyclic carbonate compound and the diamine compound, which is at least one compound selected from the group consisting of a diamine compound having only two primary amine groups as amine groups, aminoethylethanolamine, and hydroxyethylaminopropylamine.

14. The weather strip material according to claim 12 ,
wherein the resin composition comprises the self-crosslinking polyhydroxy polyurethane resin and the material ratio of the material in a range from 1 to 100 parts by mass relative to 100 parts by mass of the self-crosslinking polyhydroxy polyurethane resin.

15. The weather strip material according to claim 12 ,
wherein the resin composition further comprises an additive comprising one fine powder or a combination of two or more fine powders selected from the group consisting of organic fine powders and inorganic fine powders, and
the additive is added in a range from 1 to 150 parts by mass relative to 100 parts by mass of the self-crosslinking polyhydroxy polyurethane resin.

16. The resin according to claim 1 ,
wherein the modifier is a reaction product of a masking agent and an organic polyisocyanate compound,
the organic polyisocyanate compound is an aliphatic or aromatic polyisocyanate compound or an adduct of an aliphatic or aromatic polyisocyanate compound with other compound,
the masking agent is at least one compound selected from the group consisting of alcohol-based compounds, phenol-based compounds, active methylene-based compounds, acid amide-based compounds, imidazole-based compounds, urea-based compounds, oxime-based compounds, and pyridine-based compounds.

Assignees

• Hanada Kazuyuki
• Kimura Kazuya
• Takahashi Kenichi
• Kawakami Osamu
• Uruno Manabu
• Dainichiseika Color Chem
• Ukima Colour & Chem Mfg

Inventors

• Hanada Kazuyuki
• Kimura Kazuya
• Takahashi Kenichi
• Kawakami Osamu
• Uruno Manabu

Classifications

• C08G18/807 Primary

  with nitrogen containing compounds · CPC title

• Y10T442/20

  Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer · CPC title

• C08G71/04 Primary

  Polyurethanes · CPC title

• D06N2211/28

  Artificial leather · CPC title

• B32B27/32

  comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)} · CPC title