IP Library Patent Application 17037149
Patent Application
App. No. 17/037,149

SURFACE TREATMENT AGENT

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Patent No.
US None
App. No.
17/037,149
Abstract

A surface-treating agent comprising at least one perfluoro(poly)ether group containing silane compound of any of the formulae (A1), (A2), (B1), (B2), (C1) and (C2): wherein, each of symbols is as defined in the specification, wherein a proportion of the perfluoro(poly)ether group containing silane compound having a molecular weight of 3,000 or less in the perfluoro(poly)ether group containing silane compounds of any of the above general formulae is 9 mol % or less.

Claims (184)

1 . A surface-treating agent comprising at least one perfluoro(poly)ether group containing silane compound of any of the formulae (A1), (A2), (B1), (B2), (C1) and (C2):

wherein:

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 a, b, c and d are each independently an integer of 0-200, 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 or d is not limited in the formula;

Rf is each independently at each occurrence an alkyl group having 1-16 carbon atoms which may be substituted by one or more fluorine atoms;

R 1 is each independently at each occurrence a hydrogen atom or an alkyl group having 1-22 carbon atoms;

R 2 is each independently at each occurrence a hydroxyl group or a hydrolyzable group;

R 11 is each independently at each occurrence a hydrogen atom or a halogen atom;

R 12 is each independently at each occurrence a hydrogen atom or a lower alkyl group;

n is, independently per a unit (—SiR 1 n R 2 3-n ), an integer of 0-3;

there is at least one R 2 in the formulae (A1), (A2), (B1) and (B2);

X 1 is each independently a single bond or a 2-10 valent organic group;

X 2 is each independently at each occurrence a single bond or a divalent organic group;

t is each independently at each occurrence an integer of 1-10;

α is each independently an integer of 1-9;

α′ is each independently an integer of 1-9;

X 5 is each independently a single bond or a 2-10 valent organic group;

β is each independently an integer of 1-9;

β′ is each independently an integer of 1-9;

X 7 is each independently a single bond or a 2-10 valent organic group;

γ is each independently an integer of 1-9;

γ′ is each independently an integer of 1-9;

R a is each independently at each occurrence —Z—SiR 71 p R 72 q R 73 r ;

Z is each independently at each occurrence an oxygen atom or a divalent organic group;

R 71 is each independently at each occurrence R a′ ;

R a′ has the same definition as that of R a ;

in R a , the number of Si atoms which are straightly linked via the Z group is up to five;

R 72 is each independently at each occurrence a hydroxyl group or a hydrolyzable group;

R 73 is each independently at each occurrence a hydrogen atom or a lower alkyl group;

p is each independently at each occurrence an integer of 0-3;

q is each independently at each occurrence an integer of 0-3;

r is each independently at each occurrence an integer of 0-3;

in one R a , the sum of p, q and r is 3, and there is at least one R 72 in the formula (C1) and (C2);

R b is each independently at each occurrence a hydroxyl group or a hydrolyzable group;

R c is each independently at each occurrence a hydrogen atom or a lower alkyl group;

k is each independently at each occurrence an integer of 1-3;

1 is each independently at each occurrence an integer of 0-2;

m is each independently at each occurrence an integer of 0-2; and

the sum of k, l and m is 3 in each unit in parentheses with the subscript γ,

wherein a proportion of the perfluoro(poly)ether group containing silane compound having a molecular weight of 3,000 or less in the perfluoro(poly)ether group containing silane compounds of any of the above general formulae is 9 mol % or less.

2 . The surface-treating agent according to claim 1 wherein the proportion of the perfluoro(poly)ether group containing silane compound having a molecular weight of 3,000 or less in the perfluoro(poly)ether group containing silane compounds of any of the above general formulae is 7 mol % or less.

3 . The surface-treating agent according to claim 1 wherein the proportion of the perfluoro(poly)ether group containing silane compound having a molecular weight of 3,000 or less in the perfluoro(poly)ether group containing silane compounds of any of the above general formulae is 5 mol % or less.

4 . The surface-treating agent according to claim 1 wherein Rf is a perfluoroalkyl group having 1-16 carbon atoms.

5 . The surface-treating agent according to claim 1 wherein PFPE is a group of any of the following formulas (i) to (iv):

—(OCF 2 CF 2 CF 2 ) b —  (i)

wherein b is an integer of 1-200;

—(OCF(CF 3 )CF 2 ) b —  (ii)

wherein b is an integer of 1-200;

—(OCF 2 CF 2 CF 2 CF 2 ) a —(OCF 2 CF 2 CF 2 ) b —(OCF 2 CF 2 ) c —(OCF 2 ) d —   (iii)

wherein a and b are each independently 0 or an integer of 1-30, c and d are each independently an integer of 1-200, 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;

or

—(OC 2 F 4 —R 8 ) f —  (iv)

wherein R 8 is a group selected from OC 2 F 4 , OC 3 F 6 and OC 4 F 8 ; and

f is an integer of 2-100.

6 . The surface-treating agent according to claim 1 wherein X 1 , X 5 and X 7 are each independently a 2-4 valent organic group, α, β and γ are each independently 1-3, and α′, β′ and γ′ are 1.

7 . The surface-treating agent according to claim 1 wherein X 1 , X 5 and X 7 are a divalent organic group, α, β and γ are 1, and a′, β′ and γ′ are 1.

8 . The surface-treating agent according to claim 7 wherein X 1 , X 5 and X 7 are each independently —(R 31 ) p′ —(X a ) q′ —

wherein:

R 31 is a single bond, —(CH 2 ) s′ — (wherein s′ is an integer of 1-20) or a o-, m- or p-phenylene group;

X a is —(X b ) 1′ — (wherein 1′ is an integer of 1-10);

X b is each independently at each occurrence selected from the group consisting of —O—, —S—, an o-, m- or p-phenylene group, —C(O)O—, —Si(R 33 ) 2 —, —(Si(R 33 ) 2 O) m′ —Si(R 33 ) 2 — (wherein m′ is an integer of 1-100), —CONR 34 —, —O—CONR 34 —, —NR 34 — and —(CH 2 ) n′ — (wherein n′ is an integer of 1-20);

R 33 is each independently at each occurrence a phenyl group, a C 1-6 alkyl group or a C 1-6 alkoxy group;

R 34 is each independently at each occurrence a hydrogen atom, a phenyl group or a C 1-6 alkyl group;

p′ is 0 or 1;

q′ is 0 or 1;

at least one of p′ and q′ is 1,

the occurrence order of the respective repeating units in parentheses with the subscript p′ or q′ is not limited in the formula; and

R 31 and X a is may be substituted with one or more substituents selected from a fluorine atom, a C 1-3 alkyl group and a C 1-3 fluoroalkyl group.

9 . The surface-treating agent according to claim 7 wherein X 1 , X 5 and X 7 are 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 —,

—CH 2 O(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 (CH 2 ) 2 —,

—CH 2 O(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 2 (CH 2 ) 2 —,

—CH 2 O(CH 2 ) 3 Si(CH 3 ) 2 O(Si(CH 3 ) 2 O) 2 Si(CH 3 ) 2 (CH 2 ) 2 —,

—CH 2 O(CH 2 ) 3 Si(CH 3 ) 2 O(Si(CH 3 ) 2 O) 3 Si(CH 3 ) 2 (CH 2 ) 2 —,

—CH 2 O(CH 2 ) 3 Si(CH 3 ) 2 O(Si(CH 3 ) 2 O) 10 Si(CH 3 ) 2 (CH 2 ) 2 —,

—CH 2 O(CH 2 ) 3 Si(CH 3 ) 2 O(Si(CH 3 ) 2 O) 20 Si(CH 3 ) 2 (CH 2 ) 2 —,

—CH 2 OCF 2 CHFOCF 2 —,

—CH 2 OCF 2 CHFOCF 2 CF 2 —,

—CH 2 OCF 2 CHFOCF 2 CF 2 CF 2 —,

—CH 2 OCH 2 CF 2 CF 2 OCF 2 —,

—CH 2 OCH 2 CF 2 CF 2 OCF 2 CF 2 —,

—CH 2 OCH 2 CF 2 CF 2 OCF 2 CF 2 CF 2 —,

—CH 2 OCH 2 CF 2 CF 2 OCF(CF 3 )CF 2 OCF 2 —,

—CH 2 OCH 2 CF 2 CF 2 OCF(CF 3 )CF 2 OCF 2 CF 2 —,

—CH 2 OCH 2 CF 2 CF 2 OCF(CF 3 )CF 2 OCF 2 CF 2 CF 2 —,

—CH 2 OCH 2 CHFCF 2 OCF 2 —,

—CH 2 OCH 2 CHFCF 2 OCF 2 CF 2 —,

—CH 2 OCH 2 CHFCF 2 OCF 2 CF 2 CF 2 —,

—CH 2 OCH 2 CHFCF 2 OCF(CF 3 )CF 2 OCF 2 —,

—CH 2 OCH 2 CHFCF 2 OCF(CF 3 )CF 2 OCF 2 CF 2 —,

—CH 2 OCH 2 CHFCF 2 OCF(CF 3 )CF 2 OCF 2 CF 2 CF 2 —

—CH 2 OCH 2 (CH 2 ) 7 CH 2 Si(OCH 3 ) 2 OSi(OCH 3 ) 2 (CH 2 ) 2 Si(OCH 3 ) 2 OSi(OCH 3 ) 2 (CH 2 ) 2 —,

—CH 2 OCH 2 CH 2 CH 2 Si(OCH 3 ) 2 OSi(OCH 3 ) 2 (CH 2 ) 3 —,

—CH 2 OCH 2 CH 2 CH 2 Si(OCH 2 CH 3 ) 2 OSi(OCH 2 CH 3 ) 2 (CH 2 ) 3 —,

—CH 2 OCH 2 CH 2 CH 2 Si(OCH 3 ) 2 OSi(OCH 3 ) 2 (CH 2 ) 2 —,

—CH 2 OCH 2 CH 2 CH 2 Si(OCH 2 CH 3 ) 2 OSi(OCH 2 CH 3 ) 2 (CH 2 ) 2 —,

—(CH 2 ) 2 —,

—(CH 2 ) 3 —,

—(CH 2 ) 4 —,

—(CH 2 ) 6 —,

—(CH 2 ) 2 —Si(CH 3 ) 2 —(CH 2 ) 2 —

—CONH—(CH 2 ) 3 —,

—CON(CH 3 )—(CH 2 ) 3 —,

—CON(Ph)-(CH 2 ) 3 — (wherein Ph is a phenyl group),

—CONH—(CH 2 ) 6 —,

—CON(CH 3 )—(CH 2 ) 6 —,

—CON(Ph)-(CH 2 ) 6 — (wherein Ph is a phenyl group),

—CONH—(CH 2 ) 2 NH(CH 2 ) 3 —,

—CONH—(CH 2 ) 6 NH(CH 2 ) 3 —,

—CH 2 O—CONH—(CH 2 ) 3 —,

—CH 2 O—CONH—(CH 2 ) 6 —,

—S—(CH 2 ) 3 —,

—(CH 2 ) 2 S(CH 2 ) 3 —,

—CONH—(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 (CH 2 ) 2 —,

—CONH—(CH 2 ) 3 Si(CH 3 ) 2 OSi(CH 3 ) 2 OSi(CH 3 ) 2 (CH 2 ) 2 —,

—CONH—(CH 2 ) 3 Si(CH 3 ) 2 O(Si(CH 3 ) 2 O) 2 Si(CH 3 ) 2 (CH 2 ) 2 —,

—CONH—(CH 2 ) 3 Si(CH 3 ) 2 O(Si(CH 3 ) 2 O) 3 Si(CH 3 ) 2 (CH 2 ) 2 —,

—CONH—(CH 2 ) 3 Si(CH 3 ) 2 O(Si(CH 3 ) 2 O) 10 Si(CH 3 ) 2 (CH 2 ) 2 —,

—CONH—(CH 2 ) 3 Si(CH 3 ) 2 O(Si(CH 3 ) 2 O) 20 Si(CH 3 ) 2 (CH 2 ) 2 —

—C(O)O—(CH 2 ) 3 —,

—C(O)O—(CH 2 ) 6 —,

—CH 2 —O—(CH 2 ) 3 —Si(CH 3 ) 2 —(CH 2 ) 2 —Si(CH 3 ) 2 —(CH 2 ) 2 —,

—CH 2 —O—(CH 2 ) 3 —Si(CH 3 ) 2 —(CH 2 ) 2 —Si(CH 3 ) 2 —CH(CH 3 )—,

—CH 2 —O—(CH 2 ) 3 —Si(CH 3 ) 2 —(CH 2 ) 2 —Si(CH 3 ) 2 —(CH 2 ) 3 —,

—CH 2 —O—(CH 2 ) 3 —Si(CH 3 ) 2 —(CH 2 ) 2 —Si(CH 3 ) 2 —CH(CH 3 )—CH 2 —,

10 . The surface-treating agent according to claim 1 wherein

X 1 is —O—CFR 13 —(CF 2 ) e —,

R 13 is a fluorine atom or a lower fluoroalkyl group, and

e is 0 or 1.

11 . The surface-treating agent according to claim 1 wherein

X 2 is —(CH 2 ) s —, and

s is an integer of 0-2.

12 . The surface-treating agent according to claim 1 wherein k is 3, and q is 3 in R a .

13 . The surface-treating agent according to claim 1 wherein X 1 , X 5 and X 7 are each independently a 3-10 valent organic group.

14 . The surface-treating agent according to claim 13 wherein X 1 , X 5 and X 7 are each independently selected from the group consisting of:

wherein in each group, at least one of T is the following group attached to PFPE in the formulae (A1), (A2), (B1), (B2), (C1) and (C2):

—CH 2 O(CH 2 ) 2 —,

—CH 2 O(CH 2 ) 3 —,

—CF 2 O(CH 2 ) 3 —,

—(CH 2 ) 2 —,

—(CH 2 ) 3 —,

—(CH 2 ) 4 —,

—CONH—(CH 2 ) 3 —,

—CON(CH 3 )—(CH 2 ) 3 —,

—CON(Ph)-(CH 2 ) 3 — (wherein Ph is a phenyl group), and

at least one of the other T is —(CH 2 ) n — (wherein n is an integer of 2-6) attached to the carbon atom or the Si atom in the formulae (A1), (A2), (B1), (B2), (C1) and (C2) and the others are each independently a methyl group, a phenyl group, a alkoxy having 1-6 carbon atoms, or a radical scavenger group or an ultraviolet ray absorbing group,

R 41 is each independently a hydrogen atom, a phenyl group, an alkoxy group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms, and

R 42 is each independently a hydrogen atom, a C 1-6 alkyl group or a C 1-6 alkoxy group.

15 . The surface-treating agent according to claim 1 wherein the perfluoro(poly)ether group containing silane compound is at least one compound of any of the formulae (A1) and (A2).

16 . The surface-treating agent according to claim 1 wherein the perfluoro(poly)ether group containing silane compound is at least one compound of any of the formulae (B1) and (B2).

17 . The surface-treating agent a claim 1 wherein the perfluoro(poly)ether group containing silane compound is at least one compound of any of the formulae (C1) and (C2).

18 . The surface-treating agent according to claim 1 further comprising one or more components selected form a fluorine-containing oil, a silicone oil and a catalyst.

19 . The surface-treating agent according to claim 18 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′ —(OC 2 F 4 ) c′ —(OCF 2 ) d′ —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 constitute 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.

20 . The surface-treating agent according to claim 18 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.

21 . The surface-treating agent according to claim 20 wherein a mass ratio of the perfluoro(poly)ether group containing silane compound and the compound of the formula (3b) is 10:1-1:10.

22 . The surface-treating agent according to claim 20 wherein a mass ratio of the perfluoro(poly)ether group containing silane compound and the compound of the formula (3b) is 4:1-1:4.

23 . The surface-treating agent according to claim 20 wherein the compound of the formula (3a) has a number average molecular weight of 2,000-8,000.

24 . The surface-treating agent according to claim 20 wherein the compound of the formula (3b) has a number average molecular weight of 8,000-30,000.

25 . The surface-treating agent according to claim 20 wherein the compound of the formula (3b) has a number average molecular weight of 3,000-8,000.

26 . The surface-treating agent according to claim 1 further comprising a solvent.

27 . The surface-treating agent according to claim 1 which is used as an antifouling-coating agent or a water-proof coating agent.

28 . The surface-treating agent according to claim 1 for vacuum deposition.

29 . A pellet comprising the surface-treating agent according to claim 1 .

30 . 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 1 .

31 . The article according to claim 30 wherein the base material is a glass or a sapphire glass.

32 . The article according to claim 31 wherein the glass is a glass selected from the group consisting of a soda-lime glass, an alkali aluminosilicate glass, a borosilicate glass, a non-alkaline glass, a crystal glass, and a quartz glass.

33 . The article according to claim 30 wherein the article is an optical member.

34 . The article according to claim 30 wherein the article is a display.

Assignments (1)
CHANGE OF ADDRESS Recorded Jan 11, 2023
From: DAIKIN INDUSTRIES LTD.
To: DAIKIN INDUSTRIES LTD.
Reel/Frame 062355/0740 →