Polyurethane elastomer, thermoplastic resin composition comprising the polyurethane elastomer, molded article made of the thermoplastic resin composition, and method of preparing the polyurethane elastomer

Patent metadata

Field	Value
Publication number	US-10160825-B2
Application number	US-201514918852-A
Country	US
Kind code	B2
Filing date	Oct 21, 2015
Priority date	Oct 21, 2014
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

A polyurethane elastomer including a polymerization product of an amide group-including compound, a polyol compound, a polybasic acid compound, and a diisocyanate compound, a thermoplastic resin composition including the polyurethane elastomer, a molded article made of the thermoplastic resin composition, and a method of preparing the polyurethane elastomer.

First claim

What is claimed is:

1. A polyurethane elastomer comprising an amide compound, a polyol compound, a polybasic acid compound, and a diisocyanate compound,
wherein the polyurethane elastomer comprises about 10 wt % to about 80 wt % of a structural unit comprising the amide compound, about 15 wt % to about 80 wt % of a structural unit comprising the polyol compound, about 1 wt % to about 10 wt % of a structural unit comprising the polybasic acid compound, and about 0.5 wt % to 5 wt % of a structural unit comprising the diisocyanate compound, based on the total weight of the polyurethane elastomer,
wherein the polyurethane elastomer comprises a polymer of Formula 14:

or

wherein R 1 is a C 2 -C 5 alkylene group;
R 2 , R 3 , and R 4 are each independently a C 2 -C 10 alkylene group;
X and Y are each independently a linking group, a hydrogen, —N═C═O, —R 4 —N═C═O, —NH—COOH, or —R 4 —NH—COOH, wherein X and Y can be linked to form a ring;
a 1 and a 2 are each independently integers from 2 to 200;
b 1 and b 2 are each independently integers from 2 to 50;
c is an integer from 1 to 50; and
d is an integer from 1 to 10.

2. The polyurethane elastomer of claim 1 , wherein the polyurethane elastomer comprises a polymer represented by Formula 16:

or

wherein
X and Y are each independently a linking group, a hydrogen, —N═C═O, —(CH 2 ) 6 —N═C═O, —NH—COOH, or —(CH 2 ) 6 —NH—COOH, wherein X and Y can be linked to each other to form a ring;
a 1 and a 2 are each independently integers from 2 to 200;
b 1 and b 2 are each independently integers from 2 to 50;
c is an integer from 1 to 50; and
d is an integer from 1 to 10.

3. The polyurethane elastomer of claim 1 , wherein the polyurethane elastomer has a number average molecular weight (Mn) of about 2,000 to about 50,000.

4. The polyurethane elastomer of claim 1 , wherein the polyurethane elastomer has a relative viscosity of about 1.1 or greater.

5. The polyurethane elastomer of claim 1 , wherein the polyurethane elastomer is a polymerization product of a polyurethane-forming composition comprising a polyamide prepolymer and a diisocyanate compound, and wherein
the polyamide prepolymer is a polymerization product of a polyamide prepolymer-forming composition comprising the amide compound, the polyol compound, and the polybasic acid compound.

6. A thermoplastic resin composition comprising:
about 50 parts to about 98 parts by weight of an aliphatic polyester; and
about 2 parts to about 50 parts by weight of a polyurethane elastomer, based on 100 parts by weight of the thermoplastic resin composition;
wherein the polyurethane elastomer comprises an amide compound, a polyol compound, a polybasic acid compound, and a diisocyanate compound,
wherein the polyurethane elastomer comprises about 10 wt % to about 80 wt % of a structural unit comprising the amide compound, about 15 wt % to about 80 wt % of a structural unit comprising the polyol compound, about 1 wt % to about 10 wt % of a structural unit comprising the polybasic acid compound, and about 0.5 wt % to 5 wt % of a structural unit comprising the diisocyanate compound, based on the total weight of the polyurethane elastomer,
wherein the polyurethane elastomer comprises a polymer of Formula 14:

or

wherein R 1 is a C 2 -C 5 alkylene group;
R 2 , R 3 , and R 4 are each independently a C 2 -C 10 alkylene group;
X and Y are each independently a linking group, a hydrogen, —N═C═O, —R 4 —N═C═O, —NH—COOH, or —R 4 —NH—COOH, wherein X and Y can be linked to form a ring;
a 1 and a 2 are each independently integers from 2 to 200;
b 1 and b 2 are each independently integers from 2 to 50;
c is an integer from 1 to 50; and
d is an integer from 1 to 10.

7. The thermoplastic resin composition of claim 6 , wherein the thermoplastic resin composition comprises about 60 parts to about 80 parts by weight of the aliphatic polyester, and about 20 parts to about 40 parts by weight of the polyurethane elastomer, based on 100 parts by weight of the thermoplastic resin composition.

8. The thermoplastic resin composition of claim 6 , wherein the aliphatic polyester comprises polylactic acid.

9. The thermoplastic resin composition of claim 6 , wherein the thermoplastic resin composition has an impact strength of about 40 J/m or greater.

10. A molded article comprising the thermoplastic resin composition of claim 6 .

11. A method of preparing a polyurethane elastomer of claim 1 , the method comprising:
polymerizing a polyamide-forming composition comprising an amide compound, a polyol compound, and a polybasic acid compound to obtain a polyamide prepolymer; and
polymerizing the polyamide prepolymer with a diisocyanate compound to obtain the polyurethane elastomer.

12. The method of claim 11 , wherein the polyamide prepolymer is polymerized with the diisocyanate compound at a temperature of about 220° C. to about 250° C.

13. The method of claim 11 , wherein the polyamide prepolymer is polymerized with the diisocyanate compound for about 2 hours or less.

14. A method of making a molded article, the method comprising forming the thermoplastic resin composition of claim 6 into a desired shape.

15. The polyurethane of claim 1 , comprising about 0.5 wt % to 4 wt % of a structural unit comprising the diisocyanate compound.

16. The polyurethane of claim 1 , comprising about 0.5 wt % to about 3 wt % of a structural unit comprising the diisocyanate compound.

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kim Inki
• Lee Kyunghae
• Lee Mooho
• Cho Kwangmyung

Classifications

• C08J2467/04

  Polyesters derived from hydroxy carboxylic acids, e.g. lactones (C08J2467/06 takes precedence) · CPC title

• C08G18/606

  Polyester-amides · CPC title

• C08G18/3844

  containing one nitrogen atom in the ring · CPC title

• C08J2475/04

  Polyurethanes · CPC title

• C08G18/34

  Carboxylic acids; Esters thereof with monohydroxyl compounds · CPC title