Styrene-based copolymer and thermoplastic resin composition including the same

Patent metadata

Field	Value
Publication number	US-9365671-B2
Application number	US-201414557478-A
Country	US
Kind code	B2
Filing date	Dec 2, 2014
Priority date	Dec 4, 2013
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

Provided are a styrene-based copolymer prepared from a mixture including (A) an aromatic vinyl-based compound, (B) an unsaturated nitrile-based compound, and (C) a silicone-based compound having two or more unsaturated reactive groups to thereby be capable of implementing a uniform and excellent low gloss property with minimal or no deterioration of physical properties such as impact resistance, heat resistance, and the like, and a thermoplastic resin composition including the same.

First claim

What is claimed is:

1. A styrene-based copolymer prepared from a mixture comprising:
(A) an aromatic vinyl-based compound,
(B) an unsaturated nitrile-based compound, and
(C) an organosilicon compound having two or more unsaturated reactive groups,
wherein the organosilicon-based compound having two or more unsaturated reactive groups (C) is represented by the following Chemical Formula 2:

wherein, in Chemical Formula 2,
R 9 to R 14 are the same or different and are each independently hydrogen, 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 15 to R 17 are the same or different and are each independently hydrogen or a substituted or unsubstituted C 1 to C 6 alkyl group, and
p is an integer of 1 to 6,
wherein the organosilicon compound having two or more unsaturated reactive groups (C) further includes a vinyl silane compound represented by the following Chemical Formula 3:
(R 18 ) 2 Si(CH═CH 2 ) 2   [Chemical Formula 3]

wherein, in Chemical Formula 3, R 18 is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, or a substituted or unsubstituted C6 to C20 aryl group.

2. The styrene-based copolymer of claim 1 , wherein the organosilicon compound having two or more unsaturated reactive groups (C) is used in an amount of about 0.1 to about 10 parts by weight based on about 100 parts by weight of a monomer mixture including about 60 to about 80 wt % of the aromatic vinyl-based compound (A) and about 20 to about 40 wt % of the unsaturated nitrile-based compound (B).

3. The styrene-based copolymer of claim 2 , wherein the organosilicon compound having two or more unsaturated reactive groups (C) is used in an amount of about 0.5 to about 5 parts by weight.

4. The styrene-based copolymer of claim 1 , wherein the organosilicon compound having two or more unsaturated reactive groups (C) comprises 1,3,5-trimethyl-1,3,5-trivinyl-cyclotrisiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetravinyl-cyclotetrasiloxane, 1,3,5,7,9-pentamethyl-1,3,5,7,9-pentavinyl-cyclopentasiloxane, 1,3,5-triethyl-1,3,5-trivinyl-cyclotrisiloxane, 1,3,5,7-tetraethyl-1,3,5,7-tetravinyl-cyclotetrasiloxane, 1,3,5,7,9-pentaethyl-1,3,5,7,9-pentavinyl-cyclopentasiloxane, or a mixture thereof.

5. The styrene-based copolymer of claim 1 , wherein the vinyl silane compound comprises divinyl silane, trivinyl silane, dimethyldivinylsilane, divinylmethylsilane, methyltrivinylsilane, diphenyldivinylsilane, divinylphenylsilane, trivinylphenylsilane, divinylmethylphenylsilane, tetravinylsilane, dimethylvinyldisiloxane, divinyldiphenylchlorosilane, or a mixture thereof.

6. The styrene-based copolymer of claim 1 , wherein the organosilicon compound having two or more unsaturated reactive groups (C) has a weight average molecular weight of about 150 to about 6,000 g/mol.

7. The styrene-based copolymer of claim 1 , wherein the styrene-based copolymer includes about 5 to about 100 wt % of an insoluble inclusion, which is measured by a Soxhlet extraction method.

8. The styrene-based copolymer of claim 1 , wherein the styrene-based copolymer has about 0.1 to about 2.0 wt % of a silicone content, which is measured by an X-Ray Fluorescence Analyzer (X-ray Florescence Analysis: XRF).

9. The styrene-based copolymer of claim 1 , wherein the mixture further comprises a multi-functional vinyl-based compound selected from the group consisting of divinyl polydimethylsiloxane, vinyl-modified dimethylsiloxane, divinylbenzene, ethyleneglycol, di(meth)acrylate, allyl(meth)acrylate, diallylphthalate, diallylmaleate, triallylisocyanurate, and mixtures thereof.

10. The styrene-based copolymer of claim 1 , wherein the aromatic vinyl-based compound comprises styrene, α-methylstyrene, β-methylstyrene, p-methylstyrene, p-t-butylstyrene, ethylstyrene, vinyl xylene, monochlorostyrene, dichlorostyrene, dibromostyrene, vinylnaphthalene, or a mixture thereof.

11. The styrene-based copolymer of claim 1 , wherein the unsaturated nitrile-based compound comprises acrylonitrile, methacrylonitrile, ethacrylonitrile, phenylacrylonitrile, α-chloroacrylonitrile, fumaronitrile, or a mixture thereof.

12. The styrene-based copolymer of claim 1 , wherein the styrene-based copolymer has a glass transition temperature (Tg) of about 95 to about 115° C.

13. A thermoplastic resin composition comprising the styrene-based copolymer according to claim 1 .

14. The thermoplastic resin composition of claim 13 , wherein thermoplastic resin composition is a styrene-acrylonitrile copolymer (SAN) resin composition, a methylmethacrylate-styrene-acrylonitrile copolymer (MSAN) resin composition, an acrylonitrile-butadiene-styrene copolymer (ABS) resin composition, a methylmethacrylate-acrylonitrile-butadiene-styrene copolymer (MABS) resin composition, an acrylonitrile-styrene-acrylate copolymer (ASA) resin composition, a polycarbonate (PC)/acrylonitrile-butadiene-styrene copolymer (ABS) alloy resin composition, a polycarbonate (PC)/acrylonitrile-styrene-acrylate copolymer (ASA) alloy resin composition, a polymethylmethacrylate (PMMA)/acrylonitrile-butadiene-styrene copolymer (ABS) alloy resin composition, a polymethylmethacrylate (PMMA)/methylmethacrylate-acrylonitrile-butadiene-styrene copolymer (MABS) alloy resin composition, a polymethylmethacrylate (PMMA)/acrylonitrile-styrene-acrylate copolymer (ASA) alloy resin composition, or a mixture thereof.

15. A molded product comprising the thermoplastic resin composition of claim 13 .

16. The molded product of claim 15 , having a gloss of about 20 to about 90%, the gloss measured at an angle of about 60 degrees by an evaluation method defined by ASTM D523.

17. The molded product of claim 15 , having an absolute value of surface skewness (Rsk) of about 0.001 to about 1, the absolute value of surface skewness (Rsk) measured by an evaluation method defined by JIS B-0601.

18. The styrene-based copolymer of claim 1 , wherein the styrene-based copolymer has a gloss of 10.5 to 43.5%, the gloss measured at an angle of about 60 degrees by an evaluation method defined by ASTM D523.

Assignees

• Samsung Sdi Co Ltd

Inventors

• Kim Bo Eun
• Jang Joo Hyun
• Heo Jae Won
• Park Kwang Soo
• Senthilkumar Natarajan
• Kim Il Jin
• Oh Jun Sung

Classifications

• C08L33/20

  Homopolymers or copolymers of acrylonitrile (C08L55/02 takes precedence) · CPC title

• C08F230/08 Primary

  containing silicon · CPC title

• C08F212/10

  with nitriles · CPC title

• C08F212/08 Primary

  Styrene · CPC title

• C08L25/08

  Copolymers of styrene (C08L29/08, C08L35/06, C08L55/02 take precedence) · CPC title