Surface modifier and its use
View Patent ↗A surface modifier comprising an organosilicone compound represented by General Formula (A) and/or General Formula (B): F—(CF 2 ) q —(OC 3 F 4 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″Si(X′) 3-a (R 1 ) a (A) and F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″(X′) 2-a (R 1 ) a SiO(F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o —(CH 2 ) p XX″(X′) 1-a (R 1 ) a SiO) z F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″(X′) 2-a (R 1 ) a Si(B) wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; X is oxygen or a bivalent organic spacer group: X″ is a bivalent organosilicone spacer group; X′ is hydrolysable group; and z is an integer from 0 to 10 when a is 0 or 1.
1. A surface modifier comprising an organosilicone compound represented by General Formula (A):
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″Si(X′) 3-a (R 1 ) a
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; X is oxygen (—O—), an amide group (—C(═O)—NH—), or an ester group (—C(═O)—O—); X″ is a bivalent organosilicone spacer group comprising —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b O— or —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b R 3 —, where R 2 is independently a C 1-22 hydrocarbon group, R 3 is independently a C 1-22 linear or branched optionally substituted alkylene group, and b is an integer from 1 to 100; R 1 is a C 1-22 linear or branched hydrocarbon group; a is an integer from 0 to 2; and X′ is a hydrolysable group selected from an alkoxy or alkoxy substituted alkoxy group, an acyloxy group, an alkenyloxy group, an iminoxy group, a substituted amino group, an amido group, a substituted aminoxy group, or halogen.
2. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 1, X is O, and a is 0 or 1.
3. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 1, X is oxygen, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b R 3 — where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is independently a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
4. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 1, X is oxygen, X′ is alkoxy, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b R 3 — where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is independently a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
5. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is oxygen, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b O— where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
6. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is oxygen, X′ is alkoxy, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b O— where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
7. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is amide, and a is 0 or 1.
8. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is amide, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b R 3 — where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
9. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is amide, X′ is alkoxy, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b R 3 — where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
10. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is amide, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b O— where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
11. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is amide, X′ is alkoxy, X″ is —R 3 Si(R 2 ) 2 (O(R 2 )Si) b O— where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
12. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is an ester group (—C(═O)—O—), and a is 0 or 1.
13. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is an ester group (—C(═O)—O—), X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b R 3 — where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
14. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is an ester group (—C(═O)—O—), X′ is alkoxy, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b R 3 — where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
15. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is an ester group (—C(═O)—O—), X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b O— where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
16. The surface modifier according to claim 1 , wherein in General Formula (A), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, X is an ester group (—C(═O)—O—), X′ is alkoxy, X″ is —R 3 Si(R 2 ) 2 (O(R 2 ) 2 Si) b O— where R 2 is independently C 1 to C 22 hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, b is 1-100, and a is 0 or 1.
17. The surface modifier according to claim 1 , with the addition of a catalyst to promote surface modification wherein the proportion of compound represented by General Formula (A) and catalyst is not limited.
18. A method for producing an organosilicone compound represented by General Formula (A):
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″Si(X′) 3-a (R 1 ) a
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; X is oxygen (—O—), an amide group (—(═O)—NH—), or an ester group (—C(═O)—O—); X″ is a bivalent organosilicone spacer group comprising —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b O— or —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b R 3 —, where R 2 is independently a C 1-22 hydrocarbon group, R 3 is independently a C 1-22 linear or branched optionally substituted alkylene group, and b is an integer from 1 to 100; R 1 is a C 1-22 linear or branched hydrocarbon group; X′ is a hydrolysable group selected from an alkoxy or alkoxy substituted alkoxy group, an acyloxy group, an alkenyloxy group, an iminoxy group, a substituted amino group, an amido group, a substituted aminoxy group, or halogen, and a is 0,
the method using a hydrosilylation reaction between HMe 2 Si(OMe 2 Si) b R 3 Si(X′) 3-a (R 1 ) a where R 1 is a C 1-22 linear or branched hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, a is either 0 or 1, b is an integer from 1-100 and a compound represented by General Formula (C) below in the presence of a transition metal:
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″′ (C)
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; X is oxygen (—O—), an amide group (—C(═O)—NH—), or an ester group (—C(═O)—O—); and X″′ is a monovalent organic group having terminal ethylenic unsaturation.
19. A method for producing an organosilicone compound represented by General Formula (A):
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″Si(X′) 3-a (R 1 ) a
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; X is oxygen (—O—), an amide group (—C(═O)—NH—), or an ester group (—C(═O)—O—); X″ is a bivalent organosilicone spacer group comprising —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b O— or —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b R 3 —, where R 2 is independently a C 1-22 hydrocarbon group, R 3 is independently a C 1-22 linear or branched optionally substituted alkylene group, and b is an integer from 1 to 100, R 1 is a C 1-22 linear or branched hydrocarbon group; X′ is a hydrolysable group selected from an alkoxy or alkoxy substituted alkoxy group, an acyloxy group, an alkenyloxy group, an iminoxy group, a substituted amino group, an amido group, a substituted aminoxy group, or halogen, and a is 0,
the method using a hydrosilylation reaction between HMe 2 Si(OMe 2 Si) b OSi(X′) 3-a (R 1 ) a where R 1 is a C 1-22 linear or branched hydrocarbon group, a is either 0 or 1, b is an integer from 0-100 and a compound represented by General Formula (C) below in the presence of a transition metal:
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″′ (C)
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; X is oxygen (—O—), an amide group (—C(═O)—NH—), or an ester group (—C(═O)—O—); and X″′ is a monovalent organic group having terminal ethylenic unsaturation.
20. A method for producing an organosilicone compound represented by General Formula (A):
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″Si(X′) 3-a (R 1 ) a
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; X is oxygen (—O—), an amide group (—C(═O)—NH—), or an ester group (—C(═O)—O—); X″ is a bivalent organosilicone spacer group comprising —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b O— or —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b R 3 —, where R 2 is independently a C 1-22 hydrocarbon group, R 3 is independently a C 1-22 linear or branched optionally substituted alkylene group, and b is an integer from 1 to 100, R 1 is a C 1-22 linear or branched hydrocarbon group; X′ is an alkoxy group, and a is 0,
the method using a hydrosilylation reaction between HMe 2 Si(OMe 2 Si) b R 3 Si(X′) 3-a (R 1 ) a where R 1 is a C 1-22 linear or branched hydrocarbon group, R 3 is a C 1-22 linear or branched optionally substituted alkylene group, a is either 0 or 1, b is an integer from 1-100 and a compound represented by General Formula (C) below in the presence of a transition metal:
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″′ (C)
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; and X is oxygen (—O—), an amide group (—C(═O)—NH—), or an ester group (—C(═O)—O—); and X″′ is a monovalent organic group having terminal ethylenic unsaturation.
21. A method for producing an organosilicone compound represented by General Formula (A):
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″Si(X′) 3-a (R 1 ) a
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; X is oxygen (—O—), an amide group (—C(═O)—NH—), or an ester group (—C(═O)—O—); X″ is a bivalent organosilicone spacer group comprising —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b O— or —R 3 Si(R 2 ) 2 (OSi(R 2 ) 2 ) b R 3 —, where R 2 is independently a C 1-22 hydrocarbon group, R 3 is independently a C 1-22 linear or branched optionally substituted alkylene group, and b is an integer from 1 to 100, R 1 is a C 1-22 linear or branched hydrocarbon group; X′ is an alkoxy group, and a is 0,
the method using a hydrosilylation reaction between HMe 2 Si(OMe 2 Si) b OSi(X) 3-a (R 1 ) a where R 1 is a C 1-22 linear or branched hydrocarbon group, a is either 0 or 1, b is an integer from 0-100 and a compound represented by General Formula (C) below in the presence of a transition metal:
F—(CF 2 ) q —(OC 3 F 6 ) m —(OC 2 F 4 ) n —(OCF 2 ) o (CH 2 ) p XX″′ (C)
wherein q is an integer from 1 to 3; m, n, and o are independently integers from 0 to 200; p is 0, 1 or 2; and X is oxygen (—O—), an amide group (—C(═O)—NH—), or an ester group (—C(═O)—O—); and X″′ is a monovalent organic group having terminal ethylenic unsaturation.
22. The method for producing an organosilicone compound according to claim 18 , wherein the transition metal is platinum or rhodium.
23. The method for producing an organosilicone compound according to claim 18 , wherein in General Formula (C), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 1, and X is O.
24. The method for producing an organosilicone compound according to claim 18 , wherein in General Formula (C), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, and X is amide.
25. The method for producing an organosilicone compound according to claim 18 , wherein in General Formula (C), q is 3, m is an integer from 10 to 200, n is 1, o is 0, p is 0, and X is an ester group (—C(═O)—O—).