Aromatic vinyl-based copolymer and thermoplastic resin composition including the same

Patent metadata

Field	Value
Publication number	US-9796841-B2
Application number	US-201514872246-A
Country	US
Kind code	B2
Filing date	Oct 1, 2015
Priority date	Oct 2, 2014
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

An aromatic vinyl copolymer is a polymer of a reaction mixture including: an aromatic vinyl compound; a vinyl cyanide compound; a silicone compound having at least two unsaturated reactive groups; and a C 4 to C 20 linear or branched alkyl group-containing acrylic compound. A thermoplastic resin composition including the aromatic vinyl copolymer can have excellent matting properties, impact resistance, flowability, and balance therebetween.

First claim

What is claimed is:

1. An aromatic vinyl copolymer prepared by copolymerization of a reaction mixture comprising:
an aromatic vinyl compound;
a vinyl cyanide compound;
a silicone compound having at least two unsaturated reactive groups; and
a C 4 to C 20 linear or branched alkyl group-containing acrylic compound,
wherein the silicone compound comprises at least one of a first silicone compound having a weight average molecular weight of about 150 g/mol to less than 6,000 g/mol as represented by Formula 1 and a second silicone compound having a weight average molecular weight of about 6,000 g/mol to about 100,000 g/mol as represented by Formula 2a:

wherein a, b and c are the same or different and are each independently an integer of 0 to 79, provided that a, b and c are not 0 at the same time and a+b+c ranges from 1 to 79; R 1 to R 8 are the same or different and are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 30 alkynyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, a substituted or unsubstituted C 1 to C 30 heteroaryl group, a (meth)acrylate group, a hydroxyl group, an alkoxy group, an amino group, an epoxy group, a carboxyl group, a halogen group, an ester group, an isocyanate group, or a mercapto group; with the proviso that at least two of R 1 to R 8 include polymerizable unsaturated reactive groups; wherein the compound has a linear structure or a cyclic structure in which R 1 to R 8 are linked to one another or form a single bond;

wherein each R 26 is independently a hydrogen atom or a C 1 to C 10 alkyl group; each R 27 is independently a single bond or a C 1 to C 10 alkenyl group; each R 28 is a (meth)acrylate group; and m is an integer from 80 to 1,500.

2. The aromatic vinyl copolymer according to claim 1 , wherein the reaction mixture comprises about 0.1 parts by weight to about 20 parts by weight of the silicone compound and about 1 part by weight to about 20 parts by weight of the acrylic compound, each based on about 100 parts by weight of a monomer mixture comprising about 60 wt % to about 80 wt % of the aromatic vinyl compound and about 20 wt % to about 40 wt % of the vinyl cyanide compound.

3. The aromatic vinyl copolymer according to claim 1 , wherein the compound represented by Formula 1 comprises a compound represented by Formula 3:

wherein R 17 to R 22 are the same or different and are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, or a substituted or unsubstituted C 6 to C 20 aryl group; R 23 to R 25 are the same or different and are each independently a hydrogen atom or a substituted or unsubstituted C 1 to C 6 alkyl group; and n is an integer of 1 to 6.

4. The aromatic vinyl copolymer according to claim 1 , wherein the first silicone compound has a weight average molecular weight of about 150 g/mol to about 3,000 g/mol, and the second silicone compound has a weight average molecular weight of about 6,500 g/mol to about 30,000 g/mol.

5. The aromatic vinyl copolymer according to claim 1 , wherein a difference in weight average molecular weight between the first silicone compound and the second silicone compound ranges from about 5,000 g/mol to about 20,000 g/mol.

6. The aromatic vinyl copolymer according to claim 1 , wherein the aromatic vinyl copolymer comprises about 5 wt % to 100 wt % of insolubles remaining after Soxhlet extraction for 48 hours using tetrahydrofuran (THF), and about 0.03 wt % to about 3.26 wt % of silicon measured by X-ray fluorescence (XRF) analysis, based on the total weight of the copolymer.

7. The aromatic vinyl copolymer according to claim 1 , wherein the aromatic vinyl copolymer has a glass transition temperature of about 90° C. to about 120° C.

8. A thermoplastic resin composition comprising the aromatic vinyl copolymer according to claim 1 , wherein the thermoplastic resin composition has a gloss of about 20% to about 60% as measured at an angle of about 60° in accordance with ASTM D523; an Izod impact strength of about 5 kgf·cm/cm to about 15 kgf·cm/cm as measured on an about 1/8″ thick specimen in accordance with ASTM D256; and a melt index (MI) of about 5.5 g/10 min to about 20 g/10 min as measured under conditions of about 200° C./10 kg in accordance with ISO 1133.

9. The thermoplastic resin composition according to claim 8 , comprising the aromatic vinyl copolymer in an amount of about 1 wt % to about 50 wt % based on the total weight of the thermoplastic resin composition.

10. The thermoplastic resin composition according to claim 8 , comprising: a thermoplastic resin comprising at least one of a rubber-modified aromatic vinyl copolymer, a polycarbonate resin, and a poly(meth)acrylate resin.

11. A molded article formed of the thermoplastic resin composition according to claim 8 .

12. The aromatic vinyl copolymer according to claim 4 , wherein the first silicone compound has a weight average molecular weight of about 150 g/mol to about 1,000 g/mol, and the second silicone compound has a weight average molecular weight of about 7,000 g/mol to about 20,000 g/mol.

13. The aromatic vinyl copolymer according to claim 1 , wherein the second silicone compound comprises methacrylated polydimethylsiloxane (MPDMS), wherein in Formula 2a, R 26 is a methyl group, R 27 is a propylene group, and R 28 is a (meth)acrylate group.

14. The aromatic vinyl copolymer according to claim 1 , wherein the first silicone compound comprises a compound represented by Formula 3:

wherein R 17 to R 22 are the same or different and are each independently a hydrogen atom, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, or a substituted or unsubstituted C 6 to C 20 aryl group; R 23 to R 25 are the same or different and are each independently a hydrogen atom or a substituted or unsubstituted C 1 to C 6 alkyl group; and n is an integer of 1 to 6; and
wherein the first silicone compound has a weight average molecular weight of about 150 g/mol to about 3,000 g/mol, and the second silicone compound has a weight average molecular weight of about 6,500 g/mol to about 30,000 g/mol.

15. The aromatic vinyl copolymer according to claim 14 , wherein the first silicone compound has a weight average molecular weight of about 150 g/mol to about 1,000 g/mol, and the second silicone compound has a weight average molecular weight of about 7,000 g/mol to about 20,000 g/mol.

Assignees

• Samsung Sdi Co Ltd
• Lotte Advanced Mat Co Ltd

Inventors

• Heo Jae Won
• Jang Joo Hyun
• Park Kwang Soo
• Kim Bo Eun
• Jung Yu Jin
• Chang Ki Bo
• Jin Young Sub

Classifications

• C08L2207/04

  Thermoplastic elastomer · CPC title

• C08F220/44

  Acrylonitrile · CPC title

• C08L25/12 Primary

  with unsaturated nitriles · CPC title

• C08J5/00

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

• C08F212/10

  with nitriles · CPC title