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-2016108167-A1
Application number	US-201514918852-A
Country	US
Kind code	A1
Filing date	Oct 21, 2015
Priority date	Oct 21, 2014
Publication date	Apr 21, 2016
Grant date	—

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.

2 . The polyurethane elastomer of claim 1 , wherein the polyurethane elastomer comprises at least one hard segment polymer block and at least one soft segment polymer block.

3 . The polyurethane elastomer of claim 2 , wherein the hard segment polymer block is a copolymer block that comprises at least one first polymer block comprising a structural unit comprising the amide compound and at least one second polymer block comprising a structural unit comprising the diisocyanate compound.

4 . The polyurethane elastomer of claim 2 , wherein the soft segment polymer block comprises a structural unit comprising the polyol compound.

5 . The polyurethane elastomer of claim 1 , wherein the amide compound is a linear amide compound, a cyclic amide compound, or a combination thereof.

6 . The polyurethane elastomer of claim 5 , wherein the amide compound is a C3-C20 lactam.

7 . The polyurethane elastomer of claim 1 , wherein the polyol compound is a polyether polyol compound, a polyester polyol compound, a polycarbonate polyol compound, or a combination thereof.

8 . The polyurethane elastomer of claim 7 , wherein the polyol compound comprises a polyether polyol of Formula 3:

wherein
R 3 is a C2-C10 branched or linear alkylene group; and
l is an integer of 10 to 100.

9 . The polyurethane elastomer of claim 7 , wherein the polyol compound comprises a polyether polyol compound with molecular weight of about 1,000 to about 4,000.

10 . The polyurethane elastomer of claim 1 , wherein the polybasic acid compound comprises an aliphatic dicarboxylic acid, aromatic dicarboxylic acid, alicyclic dicarboxylic acid, acid anhydrides thereof, or a combination thereof.

11 . The polyurethane elastomer of claim 1 , wherein the polybasic acid compound comprises oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebasic acid, phthalic acid, isophthalic acid, terephthalic acid, hexahydrophthalic acid, hexahydroisophthalic acid, or a combination thereof.

12 . The polyurethane elastomer of claim 1 , wherein the diisocyanate compound comprises an aliphatic diisocyanate compound, an aromatic diisocyanate compound an alicyclic diisocyanate compound, or a combination thereof.

13 . The polyurethane elastomer of claim 1 , wherein the diisocyanate compound is toluene diisocyanate (TDI), 4,4-methylenediphenyldiisocyanate (MDI), 1,5-naphthalene diisocyanate (NDI), 1,6-hexamethylene diisocyanate (HMDI), isophorone diisocyanate (IPDI), xylene diisocyanate (XDI), tetramethylxylene diisocyanate (TMXDI), 1,8-diisocyanate methyloctane, or a combination thereof.

14 . The polyurethane elastomer of claim 1 , 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 1 wt % to about 5 wt % of a structural unit comprising the diisocyanate compound, based on the total weight of the polyurethane elastomer.

15 . The polyurethane elastomer of claim 1 , wherein the polyurethane elastomer comprises at least one structural unit of:
—(—R 1 —O—)—  <Formula 10>
—(—CO—R 2 —NH—)—  <Formula 11>
—(—OC—NH—R 4 —NH—CO—)—  <Formula 12>
or a combination thereof, and at least one structural units of:
—(—OOC—R 3 —COO—)—  <Formula 13a>

—(—OOC—R 3 —CO—)—  <Formula 13b>

—(—OC—R 3 —CO—)—  <Formula 13c>

or a combination thereof, wherein, in Formulae 10 to 12 and Formulae 13a to 13c: R 1 and R 2 are each independently a C2-C10 linear or branched alkylene group; and R 3 and R 4 are each independently a covalent bond; a C1-C20 linear or branched alkylene group that is unsubstituted or substituted with a C1-C10 alkyl group or a C6-C20 aryl group; a C6-C20 arylene group or a C2-C20 heteroarylene group that is unsubstituted or substituted with a halogen or a C1-C10 linear or branched alkyl group; or a C2-C20 cycloalkylene group that is unsubstituted or substituted with a C1-C10 alkyl group, a C6-C20 aryl group, a C6-C10 cycloalkyl group, a C2-C10 alkenyl group, or a C2-C10 alkynyl group, and wherein the polyurethane elastomer comprises a mole fraction a of the structural unit represented by Formula 10: a mole fraction b of the structural unit represented by Formula 11, a mole fraction c of the structural formula of Formula 12, and mole fractions d1, d2, and d3 of the structural units represented by Formulae 13a to 13c, respectively, that satisfy the following relationship: a+b+c+d=1 and d=d1+d2+d3, wherein 0<a<1, 0<b<1, 0<c<1, 0<d<1, 0≦d1<1, 0≦d2<1, and 0≦d3<1; and wherein the total degree of polymerization of the polyurethane elastomer is in a range of about 1 to about 100,000.

16 . The polyurethane elastomer of claim 1 , wherein the polyurethane elastomer comprises a polymer of Formula 14:

or
Formula 15:

wherein R 1 is a C2-C5 alkylene group;
R 2 , R 3 , and R 4 are each independently a C2-C10 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;
a1 and a2 are each independently integers from 2 to 200;
b1 and b2 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.

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

or
Formula
17:

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;
a1 and a2 are each independently integers from 2 to 200;
b1 and b2 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.

18 . 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.

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

20 . 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.

21 . A thermoplastic resin

Assignees

• Samsung Electronics Co Ltd

Inventors

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

Classifications

• C08J2367/04

  Polyesters derived from hydroxy carboxylic acids, e.g. lactones (C08J2367/06 takes precedence) · CPC title

• C08J5/00

  Manufacture of articles or shaped materials containing macromolecular substances (manufacture of semi-permeable membranes B01D67/00 - B01D71/00) · CPC title

• C08J2475/04

  Polyurethanes · CPC title

• C08G18/3206

  aliphatic · CPC title

• C08J2375/04

  Polyurethanes · CPC title