IP Library Granted Patent US 9,273,224
Granted Patent B2
US 9,273,224 · App. 12/993,575 · Granted Mar 1, 2016

Coating agent composition

Inventors: Satoshi Onodera (Chiba, JP); Toru Masatomi (Ichihara, JP); Motoshi Sasaki (Ichihari, JP)
Assignee: DOW CORNING TORAY CO., LTD.
C09D143/04
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Quick Facts
Patent No.
US 9,273,224
App. No.
12/993,575
Granted
Mar 1, 2016
Kind
B2
Abstract

To provide a coating agent composition that cures to form a transparent film that exhibits a high water repellency, a high durability, and an excellent adhesiveness to substrate. A coating agent composition that characteristically comprises (A) an acrylic copolymer obtained by the radical copolymerization of (A1) 1 mole silane compound represented by the general formula: CH 2 ═C(R 1 )—COO-Q-SiR 2 n (OR 3 ) 3-n , (A2) 3.70 to 6.20 moles of at least one compound that contains a vinyl polymerizable unsaturated bond, and (A3) 1.05 to 1.80 moles of a siloxysilane compound represented by general formula (2): CH 2 ═C(R 1 )—COO-Q-Si(OSiR 4 3 ) 3 at an molar ratio (A1)/{(A1)+(A2)+(A3)}=0.11 to 0.17; and (B) a condensation reaction catalyst.

Claims (41)

1. A coating agent composition that comprises

(A) 100 weight parts of an acrylic copolymer that has a weight-average molecular weight of 10,000 to 100,000 and that is obtained by the radical copolymerization of

(A1) a silane compound represented by general formula (1)

CH 2 ═C(R 1 )—COO-Q-SiR 2 n (OR 3 ) 3-n   (1)

 in the formula, R 1 is the hydrogen atom or methyl group; Q is C 2-6 divalent aliphatic hydrocarbyl group; R 2 is unsubstituted or substituted C 1-8 monovalent hydrocarbyl group; R 3 is C 1-4 aliphatic hydrocarbyl group; and n is an integer from 0 to 2,

(A2) at least one compound that contains a vinyl polymerizable unsaturated bond, said compound being selected from acrylic compounds excluding components (A1) and (A3), vinylic compounds, and styrenic compounds, at 3.70 to 6.20 moles per 1 mole component (A1), and

(A3) a siloxysilane compound represented by general formula (2), at 1.05 to 1.80 moles per 1 mole component (A1)

CH 2 ═C(R 1 )—COO-Q-Si(OSiR 4 3 ) 3   (2)

 in the formula, R 1 and Q are defined as above and R 4 is C 1-4 alkyl group

 at a molar ratio (A1)/{(A1)+(A2)+(A3)}=0.11 to 0.17; and

(B) a condensation reaction-promoting catalyst in a catalytic amount.

2. The coating agent composition according to claim 1 , that further comprises (C) organic solvent, in an amount sufficient to dissolve component (A).

3. The coating agent composition according to claim 1 , that further comprises (D) aminosilane coupling agent, at 0.1 to 10 weight parts per 100 weight parts component (A).

4. The coating agent composition according to claim 3 , characterized in that component (D) is selected from the group consisting of 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-(2-aminoethyl)aminopropyltrimethoxysilane, 3-(2-aminoethyl)aminopropylmethyldimethoxysilane, and 3-anilinopropyltrimethoxysilane.

5. The coating agent composition according to claim 1 , characterized in that the acrylic copolymer is obtained by radical copolymerization using an azo-compound at 0.30 to 0.99 mole per 100 moles of the total of components (A1) to (A3).

6. The coating agent composition according to claim 1 , characterized in that component (A2) is an alkyl methacrylate.

7. The coating agent composition according to claim 1 , wherein component (A1) is a silane compound selected from the group consisting of 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane.

8. The coating agent composition according to claim 3 , characterized in that the acrylic copolymer is obtained by radical copolymerization using an azo-compound at 0.30 to 0.99 mole per 100 moles of the total of components (A1) to (A3).

9. The coating agent composition according to claim 3 , characterized in that component (A2) is an alkyl methacrylate.

10. The coating agent composition according to claim 3 , wherein component (A1) is a silane compound selected from the group consisting of 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane.

11. The coating agent composition according to claim 1 wherein 4.1 to 5.5 moles of component (A2) are present per 1 mole of component (A1), and wherein 1.2 to 1.6 moles of component (A3) are present per mole of component (A1).

12. The coating agent composition according to claim 1 wherein components (A1), (A2), and (A3) are provided at a molar ratio (A1)/{(A1)+(A2)+(A3)}=0.12 to 0.16.

13. A coating agent composition that comprises

(A) 100 weight parts of an acrylic copolymer that has a weight-average molecular weight of 10,000 to 100,000 and that is obtained by the radical copolymerization of

(A1) 3-methacryloxypropyltrimethoxysilane,

(A2) methyl methacrylate and 2-(dimethylamino)ethyl methacrylate in a total amount ranging from 3.70 to 6.20 moles per 1 mole component (A1),

(A3) methacryloxy propyltris(trimethylsiloxy)silane at 1.05 to 1.80 moles per 1 mole component (A1),

 at a molar ratio (A1)/{(A1)+(A2)+(A3)}=0.12 to 0.16; and

(B) a condensation reaction-promoting catalyst in a catalytic amount.

14. The coating agent composition according to claim 13 wherein 4.1 to 5.5 moles of component (A2) are present per 1 mole of component (A1), and wherein 1.2 to 1.6 moles of component (A3) are present per mole of component (A1).

15. The coating agent composition according to claim 13 , that further comprises (D) aminosilane coupling agent, at 0.1 to 10 weight parts per 100 weight parts component (A).

16. The coating agent composition according to claim 13 , characterized in that the acrylic copolymer is obtained by radical copolymerization using an azo-compound at 0.30 to 0.99 mole per 100 moles of the total of components (A1) to (A3).

17. A coating agent composition that comprises

(A) 100 weight parts of an acrylic copolymer that has a weight-average molecular weight of 10,000 to 100,000 and that is obtained by the radical copolymerization of

(A1) a silane compound selected from the group consisting of 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and combinations thereof,

(A2) a compound containing a vinyl polymerizable unsaturated bond included in an amount ranging from 3.70 to 6.20 moles per 1 mole component (A1) and being selected from methyl methacrylate, methyl acrylate, ethyl methacrylate, ethyl acrylate, butyl methacrylate, butyl acrylate, 2-(dimethylamino)ethyl methacrylate, 2-(dimethylamino)ethyl acrylate, 3-(dimethylamino)propyl methacrylate, 3-(dimethylamino)propyl acrylate, 2-(diethylamino)ethyl methacrylate, 2-(diethylamino)ethyl acrylate, and combinations thereof,

(A3) a tris(trialkylsiloxy)silane compound included in an amount ranging from 1.05 to 1.80 moles per 1 mole component (A1) and being selected from CH 2 =CMe-COO—C 3 H 6 —Si(OSiMe 3 ) 3 , CH 2 ═CH—COO—C 3 H 6 —Si(OSiMe 3 ) 3 , CH 2 =CMe-COO—C 4 H 8 Si(OSiMe 3 ) 3 , CH 2 =CMe-COO—C 3 H 6 —Si(OSiEt 3 ) 3 , CH 2 ═CH—COO—C 3 H 6 —Si(OSiEt 3 ) 3 , CH 2 ═CMe-COO—C 4 H 8 —Si(OSiEt 3 ) 3 , CH 2 ═CMe-COO—C 3 H 6 —Si(OSiPr 3 ) 3 , CH 2 ═CH—COO—C 3 H 6 —Si(OSiPr 3 ) 3 , CH 2 ═CMe-COO—C 4 H 8 —Si(OSiPr 3 ) 3 , and combinations thereof, at a molar ratio (A1)/{(A1)+(A2)+(A3)}=0.12 to 0.16, wherein “Me” designates a methyl group, “Et” designates an ethyl group, and “Pr” designates a propyl group; and

(B) a condensation reaction-promoting catalyst in a catalytic amount.

18. The coating agent composition according to claim 17 wherein 4.1 to 5.5 moles of component (A2) are present per mole component (A1), and wherein 1.2 to 1.6 moles of component (A3) are present per mole component (A1).

19. The coating agent composition according to claim 17 , that further comprises (D) aminosilane coupling agent, at 0.1 to 10 weight parts per 100 weight parts component (A).

20. The coating agent composition according to claim 17 , characterized in that the acrylic copolymer is obtained by radical copolymerization using an azo-compound at 0.30 to 0.99 mole per 100 moles of the total of components (A1) to (A3).

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 17, 2019
From: DOW CORNING TORAY CO., LTD.
To: DOW TORAY CO., LTD.
Reel/Frame 051322/0925 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME PREVIOUSLY RECORDED ON REEL 025866 FRAME 0588. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNEE NAME SHOULD BE: DOW CORNING TORAY CO., LTD.. Recorded May 19, 2011
From: ONODERA, SATOSHI; MASATOMI, TORU; SASAKI, MOTOSHI
To: DOW CORNING TORAY CO., LTD.
Reel/Frame 026307/0185 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 25, 2011
From: ONODERA, SATOSHI; MASATOMI, TORU; SASAKI, MOTOSHI
To: DOW CORNING TORAY COMPANY, LTD.
Reel/Frame 025866/0588 →
Priority Claims (1)
JP 2008-153185 · Jun 11, 2008 · national
Continuity (1)
Related Publication 20110124800A1 · May 26, 2011