Surface treatment agent

Patent metadata

Field	Value
Publication number	US-10870729-B2
Application number	US-201716072697-A
Country	US
Kind code	B2
Filing date	Jan 24, 2017
Priority date	Jan 26, 2016
Publication date	Dec 22, 2020
Grant date	Dec 22, 2020

Abstract

A surface-treating agent containing (1) at least one perfluoro(poly)ether group containing silane compound of any of the formulae (A1), (A2), (B1), (B2), (C1), (C2), (D1) and (D2):

and (2) a fluorine containing oil of the general formula (O):

Rf 1 -PFPE′-Rf 2   (O)

wherein: each of the symbols are as defined herein. A content of the fluorine containing oil having a molecular weight of 2.0 or more times higher than the number average molecular weight of the fluorine-containing oils among the fluorine containing oil of the formula (O) is 10 mol % or less.

First claim

The invention claimed is:

1. A surface-treating agent comprising
(1) at least one perfluoro(poly)ether group containing silane compound of any of the formulae (A1), (A2), (B1), (B2), (C1), (C2), (D1) and (D2):

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 at least one, 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 hydroxyl group or a hydrolyzable group;
R 2 is each independently at each occurrence a hydrogen atom or an alkyl group having 1-22 carbon atoms;
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;
n1 is, independently per a unit (—SiR 1 n1 R 2 3- n 1 ), an integer of 0-3;
at least one n1 is an integer of 1-3 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 1 —SiR 71 p1 R 72 q1 R 73 r1 ;
Z 1 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 1 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;
p1 is each independently at each occurrence an integer of 0-3;
q1 is each independently at each occurrence an integer of 0-3;
r1 is each independently at each occurrence an integer of 0-3;
at least one q1 is an integer of 1-3 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;
k1 is each independently at each occurrence an integer of 1-3;
l1 is each independently at each occurrence an integer of 0-2;
m1 is each independently at each occurrence an integer of 0-2;
the sum of k1, l1 and m1 is 3 in each unit in parentheses with the subscript γ;
X 9 is each independently a single bond or a 2-10 valent organic group;
δ is each independently an integer of 1-9;
δ′ is each independently an integer of 1-9;
R d is each independently at each occurrence —Z 2 —CR 81 p2 R 82 q2 R 83 r2 ;
Z 2 is each independently at each occurrence an oxygen atom or a divalent organic group;
R 81 is each independently at each occurrence R d ′;
R d ′ has the same definition as that of R d ;
in R d , the number of C atoms which are straightly linked via the Z 2 group is up to five;
R 82 is each independently at each occurrence —Y—SiR 85 n2 R 86 3-n2 ;
Y is each independently at each occurrence a divalent organic group;
R 85 is each independently at each occurrence a hydroxyl group or a hydrolyzable group;
R 86 is each independently at each occurrence a hydrogen atom or a lower alkyl group;
n2 is an integer of 1-3 independently per unit (—Y—SiR 85 n2 R 86 3-n2 );
in formulae (D1) and (D2), at least one n2 is an integer of 1-3;
R 83 is each independently at each occurrence a hydrogen atom or a lower alkyl group;
p2 is each independently at each occurrence an integer of 0-3;
q2 is each independently at each occurrence an integer of 0-3;
r2 is each independently at each occurrence an integer of 0-3;
R e is each independently at each occurrence —Y—SiR 85 n2 R 86 n2 ;
R f is each independently at each occurrence a hydrogen atom or a lower alkyl group;
k2 is each independently at each occurrence an integer of 0-3;
l2 is each independently at each occurrence an integer of 0-3; and
m2 is each independently at each occurrence an integer of 0-3;
in formulae (D1) and (D2), at least one q2 is 2 or 3, or at least one l2 is 2 or 3; and
(2) a fluorine containing oil of the general formula (0):
Rf 1 -PFPE′-Rf 2   (O)

wherein:
Rf 1 is each independently at each occurrence a C 1-16 alkyl group which may be substituted by one or more fluorine atoms;
Rf 2 is a C 1-16 alkyl group which may be substituted by one or more fluorine atoms, a fluorine atom or a hydrogen atom;
PFPE′ is —(OC 4 F 8 ) a ′—(OC 3 F 6 ) b ′(OC 2 F 4 ) c ′—(OCF 2 ) d ′—;

a′, b′, c′ and d′ are each independently an integer of 0 or more and 300 or less, the sum of a′, b′, c′ and d′ is at least 1, 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,
wherein a content of the fluorine containing oil having a molecular weight of 2.0 or more times higher than the number average molecular weight of the fluorine-containing oil among the fluorine containing oil of the formula (O) is 10 mol % or less; and
wherein a number average molecular weight of the fluorine containing oil is 1,500 or more and 30,000 or less.

2. The surface-treating agent according to claim 1 wherein the content of the fluorine containing oil having a molecular weight of 2.0 or more times higher than the number average molecular weight of the fluorine-containing oil among the fluorine containing oil of the formula (O) is 5 mol % or less.

3. The surface-treating agent according to claim 1 wherein a content of the fluorine containing oil having a molecular weight of 1.8 or more times higher than the number average molecular weight of the fluorine-containing oil among the fluorine containing oil of the formula (O) is 10 mol % or less.

4. The surface-treating agent according to claim 3 wherein the content of the fluorine containing oil having a molecular weight of 1.8 or more times higher than the number average molecular weight of the fluorine-containing oil among the fluorine containing oil of the formula (O) is 5 mol % or less.

5. The surface-treating agent according to claim 1 wherein the number average molecular weight of the fluorine containing oil is 2,000 or more and 10,000 or less.

6. A surface-treating agent comprising
(1) at least one perfluoro(poly)ether group containing silane compound of any of the formulae (A1), (A2), (B1), (B2), (C1), (C2), (D1) and (D2):

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 at least one, and the occurrence order of the respective repeating units in parentheses with the s

Assignees

• Daikin Ind Ltd

Inventors

• Ishii Daiki
• Honda Yoshiaki
• Maehira Takeshi
• Nakano Nozomi

Classifications

• C09K3/18 Primary

  for application to surfaces to minimize adherence of ice, mist or water thereto (rendering particulate materials free flowing, in general, e.g. making them hydrophobic B01J2/30); Thawing or antifreeze materials for application to surfaces (used in liquids for heat-transfer, heat-exchange or heat-storage or for the production of heat or cold other than by combustion, e.g. radiator liquids, C09K5/00) · CPC title

• C09D183/12

  containing polyether sequences · CPC title

• C09D171/00

  Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain (based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06); Coating compositions based on derivatives of such polymers · CPC title

• C03C17/28

  with organic material (C03C17/34, C03C17/44 take precedence) · CPC title

• G02B1/18

  Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films (G02B1/16 takes precedence) · CPC title