Silane compound containing perfluoro(poly)ether group

Patent metadata

Field	Value
Publication number	US-11174349-B2
Application number	US-201916561827-A
Country	US
Kind code	B2
Filing date	Sep 5, 2019
Priority date	Jul 31, 2015
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

A perfluoro(poly)ether group containing silane compound of formula (1a) or (1b):

(Rf-PFPE) β -X—(CR a k R b l R c m ) α   (1a)

(R c m R b l R a k C) α —X-PFPE-X—(CR a k R b l R c m ) α   (1b)

wherein the symbols are as defined herein.

First claim

What is claimed is:

1. A perfluoro(poly)ether group containing silane compound of formula (1a′) formula (1b′):
Rf-PFPE-X—CR b 3   (1a′)

R b 3 C—X-PFPE-X—CR b 3   (1b′)

wherein:
Rf is each independently at each occurrence a perfluoroalkyl group having 1-16 carbon atoms;
PFPE is each independently at each occurrence a group of the formula:
—(OC 4 F 8 ) a —(OC 3 F 6 ) b —(OC 2 F 4 ) c —(OCF 2 ) d —
wherein (OC 4 F 8 ) is (OCF 2 CF 2 CF 2 CF 2 ),
(OC 3 F 6 ) is (OCF 2 CF 2 CF 2 ),
(OC 2 F 4 ) is (OCF 2 CF 2 ),
a, b, c and d are each independently an integer of 0-200, the sum of a, b, c and d is 10-200, and the occurrence order of the respective repeating units in parentheses with the subscript a, b, c or d is not limited in the formula;

X is each independently the following divalent organic group;
—R 31 —X c —R 31 —
wherein
R 31 is each independently a single bond, —(CH 2 ) s′,
s′ is an integer of 1-6,
X c is —O—, or —CONR 34 —, and
R 34 is each independently at each occurrence a hydrogen atom or a C 1-6 alkyl group,

R b is each independently at each occurrence —Y_ 13 SiR 5 n R 6 3-n ;
Y is each independently at each occurrence a C 1-6 alkylene group or —(CH 2 ) g′ —O—(CH 2 ) h′ — wherein g′ is an integer of 1-6, and h′ is an integer of 1-6;
R 5 is each independently at each occurrence a hydroxyl group, —OR, —OCOR, —O—N═C(R) 2 , —N(R) 2 , —NHR, or halogen wherein R is a substituted or non-substituted alkyl group having 1-4 carbon atoms;
R 6 is each independently at each occurrence a hydrogen atom or an alkyl group having 1-20 carbon atoms;
n is an integer of 1-3 independently per unit —Y—SiR 5 n R 6 3-n .

2. The perfluoro(poly)ether group containing silane compound according to claim 1 wherein PFPE is a group of the following formula (iv):
—(OC 2 F 4 —R 8 ) n″ —  (iv)

wherein R 8 is a group selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 , or a combination of 2 or 3 groups independently selected from these groups;
OC 4 F 8 is OCF 2 CF 2 CF 2 CF 2 ,
OC 3 F 6 is OCF 2 CF 2 CF 2 ,
OC 2 F 4 is OCF 2 CF 2 , and
n″ is an integer of 2-100.

3. The perfluoro(poly)ether group containing silane compound according to claim 1 wherein X is each independently selected from the group consisting of:
—CH 2 O(CH 2 ) 2 —,
—CH 2 O(CH 2 ) 3 —,
—CH 2 O(CH 2 ) 6 —,
—CONH—(CH 2 ) 3 —,
—CON(CH 3 )—(CH 2 ) 3 —,
—CONH—(CH 2 ) 6 —, and
—CON(CH 3 )—(CH 2 ) 6 —.

4. The perfluoro(poly)ether group containing silane compound according to claim 1 wherein Y is a C 3 alkylene group, or —(CH 2 ) g′ —O—(CH 2 ) h′ —wherein g′ is 1, and h′ is an integer of 1-6.

5. The perfluoro(poly)ether group containing silane compound according to claim 1 , having an average molecular weight of 2,000-32,000.

6. A surface-treating agent comprising at least one perfluoro(poly)ether group containing silane compound of the formula (1a′) and/or the formula (1b′) according to claim 1 .

7. The surface-treating agent according to claim 6 further comprising one or more components selected form a fluorine-containing oil, a silicone oil and a catalyst.

8. The surface-treating agent according to claim 7 wherein the fluorine-containing oil is one or more compounds of the formula (3):
R 21 —(OC 4 F 8 ) a′ —(OC 3 F 6 ) b′ —(OCF 2 ) c′ —R 22   (3)

wherein:
R 21 is an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms;
R 22 is an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms, a fluorine atom or a hydrogen atom; and
a′, b′, c′ and d′ are the repeating number of each of four repeating units of perfluoro(poly)ether which constitutes a main backbone of the polymer, and are each independently an integer of 0 or more and 300 or less, the sum of a′, b′, c′ and d′ is 1 or more, and the occurrence order of the respective repeating units in parentheses with the subscript a′, b′, c′ and d′ is not limited in the formula.

9. The surface-treating agent according to claim 7 wherein the fluorine-containing oil is one or more compounds of the formula (3a) or (3b):
R 21 —(OCF 2 CF 2 CF 2 ) b ″ —R 22   (3a)

R 21 —(OCF 2 CF 2 CF 2 CF 2 ) a″ —(OCF 2 CF 2 CF 2 ) b″ —(OCF 2 CF 2 ) c″ —(OCF 2 ) d″ —R 22   (3b)

wherein:
R 21 is an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms;
R 22 is an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms, a fluorine atom or a hydrogen atom;
in the formula (3a), b″ is an integer of 1 or more and 100 or less;
in the formula (3b), a″ and b″ are each independently an integer of 0 or more and 30 or less, and c″ and d″ are each independently an integer of 1 or more and 300 or less; and
the occurrence order of the respective repeating units in parentheses with the subscript a″, b″, c″ or d″ is not limited in the formula.

10. The surface-treating agent according to claim 9 wherein a mass ratio of the perfluoro(poly)ether group containing silane compound of the formula (1a′) or the formula (1b′) and the compound of the formula (3b) is 4:1-1:4.

11. The surface-treating agent according to claim 9 wherein the compound of the formula (3a) has a number average molecular weight of 2,000-8,000.

12. The surface-treating agent according to claim 9 wherein the compound of the formula (3b) has a number average molecular weight of 2,000-30,000.

13. The surface-treating agent according to claim 9 wherein the compound of the formula (3b) has a number average molecular weight of 8,000-30,000.

14. The surface-treating agent according to claim 6 further comprising a solvent.

15. The surface-treating agent according to claim 6 which is used as an antifouling-coating agent or a water-proof coating agent.

16. The surface-treating agent according to claim 6 for vacuum deposition.

17. A pellet containing the surface-treating agent according to claim 6 .

18. An article comprising a base material and a layer which is formed on a surface of the base material from the surface-treating agent according to claim 6 .

19. An article comprising a base material and a layer which is formed on a surface of the base material from the compound according to claim 1 .

20. The article according to claim 19 wherein the article is an optical member.

21. The article according to claim 19 wherein the article is a display.

22. The perfluoro(poly)ether group containing silane compound according to claim 1 wherein PFPE is —(OC 2 F 4 —OC 3 F 6 ) n″ —or —(OC 2 F 4 —OC 4 F 8 ) n″ —
wherein OC 4 F 8 is OCF 2 CF 2 CF 2 CF 2,
OC 3 F 6 is OCF 2 CF 2 CF 2,
OC 2 F 4 is OCF 2 CF 2 , and
n″ is an integer of 2-100.

23. The perfluoro(poly)ether group containing silane compound according to claim 1 wherein
X is each independently the following divalent organic group:
—R 31 —X c —R 31 —
wherein
R 31 is each independently a single bond, or —CH 2 —, and
X c is —O—, or —CONH—.

24. The perfluoro(poly)ether group containing silane compound according to claim 1 wherein
X is each independently the following divalent organic group:
—R 31 —X c —R 31 —
wherein
R 31 is —CH 2 —, and
X c is —O—.

25. The perfluoro(poly)ether group containing silane compound according to claim 1 wherein
X is each independently the following divalent o

Assignees

• Daikin Ind Ltd

Inventors

• Mitsuhashi Hisashi
• TAKANO Mayuko
• Namikawa Takashi
• Nomura Takashi

Classifications

• C03C2217/76

  Hydrophobic and oleophobic coatings · CPC title

• C03C17/30

  with silicon-containing compounds · CPC title

• B05D2350/63

  ceramic layer · CPC title

• B05D2203/35

  Glass · CPC title

• B05D1/60

  Deposition of organic layers from vapour phase (vapour phase deposition in general C23C14/00, C23C16/00) · CPC title