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US 10,703,932 B2Granted
Surface treating agent including perfluoro(poly)ether-group-containing silane compound
AssigneeDaikin Industries, Ltd.
InventorsKenichi Katsukawa, Hisashi Mitsuhashi, Kensuke Mohara, Tomohiro Yoshida, Masatoshi Nose, Takashi Namikawa
Life of this patent
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Abstract
A surface-treating agent including at least one perfluoro(poly)ether group containing silane compound of the formula (1): wherein Rf, PFPE, Z, Q, R1, R2, X, Y, e, f, g, h and n are as defined herein. Also disclosed is a process for preparing the compound of formula (1).
Claims22
A surface-treating agent comprising at least one perfluoro(poly)ether group containing silane compound of the formula (1):
- wherein:
- Rf is an alkyl group having 1 to 10 carbon atoms which may be substituted by one or more fluorine atoms;
- PFPE is
- —(OC4F8)a—(OC3F6)b—(OC2F4)c—(OCF2)d—
- wherein a and b is each independently an integer of 0 to 30, c and d is each independently an integer of 10-100, the sum of c and d is 10-100, 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;
- Q is an oxygen atom or a divalent organic group;
- R1 is a hydrogen atom or an alkyl group having 1 to 22 carbon atoms;
- R2 is each independently a hydrogen atom or an inert monovalent organic group;
- X is a hydroxyl group or a hydrolyzable group;
- Y is a hydrogen atom or a halogen atom;
- Z is a fluorine atom or a fluoroalkyl group having 1 to 5 carbon atoms;
- e is an integer from 0 to 3;
- f is 0 or 1;
- g is an integer from 1 to 10;
- h is an integer from 0 to 3;
- and
- n is an integer from 1 to 3,
- wherein 80 mol % or more of the perfluoro(poly)ether group containing silane compound contained in the surface-treating agent is a compound wherein g is 2 or more, and
- polydispersity of g is more than 1.0 and less than 2.0.
16 more elements
A process for preparing a compound of the formula (1):
- wherein:
- Rf is an alkyl group having 1 to 10 carbon atoms which may be substituted by one or more fluorine atoms;
- PFPE is
- —(OC4F8)a—(OC3F6)b—(OC2F4)c—(OCF2)d—
- wherein a and b is each independently an integer of 0 to 30, c and d is each independently an integer of 10-100, the sum of c and d is 10-100, 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;
- Q is an oxygen atom or a divalent organic group;
- R1 is a hydrogen atom or an alkyl group having 1 to 22 carbon atoms;
- R2 is each independently a hydrogen atom or an inert monovalent organic group;
- X is a hydroxyl group or a hydrolyzable group;
- Y is a hydrogen atom or a halogen atom;
- Z is a fluorine atom or a fluoroalkyl group having 1 to 5 carbon atoms;
- e is an integer from 0 to 3;
- f is 0 or 1;
- g is an integer from 1 to 10;
- h is an integer from 0 to 3;
- and
- n is an integer from 1 to 3,
- which comprises a step of:
- reacting a perfluoro(poly)ether compound of the formula (1a):
- wherein Rf, PFPE, Q, Z, e and f are as defined for the formula (1) and Y1 is a chlorine, an iodine or a bromine,
- with a reactive double bond containing silane compound of the formula (1b):
- wherein R1, R2, h and n are as defined for the formula (1), and X1 is a hydroxyl group, a hydrolyzable group or a halogen atom in a fluorine containing aromatic compound,
- and then, optionally following steps (a) and/or (b):
- (a) when Y and Y1 are different, converting Y1 to Y;
- and
- (b) when X and X1 are different, converting X1 to X.
23 more elements
A process for preparing a perfluoro(poly)ether group containing silane compound of the formula (1′):
- wherein:
- Rf is an alkyl group having 1 to 10 carbon atoms which may be substituted by one or more fluorine atoms;
- PFPE is
- —(OC4F8)a—(OC3F6)b—(OC2F4)c—(OCF2)d—
- wherein a and b is each independently an integer of 0 to 30, c and d is each independently an integer of 10-100, the sum of c and d is 10-100, 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;
- Q is an oxygen atom or a divalent organic group;
- R1 is a hydrogen atom or an alkyl group having 1 to 22 carbon atoms;
- X is a hydroxyl group or a hydrolyzable group;
- Z is a fluorine atom or a fluoroalkyl group having 1 to 5 carbon atoms;
- e is an integer from 0 to 3;
- f is 0 or 1;
- g is an integer from 1 to 10;
- and
- h is an integer from 0 to 3;
- which comprises a step of:
- reacting a perfluoro(poly)ether compound of the formula (1a):
- wherein Rf, PFPE, Q, Z, e and f are as defined above, and Y1 is a chlorine, an iodine or a bromine,
- with a compound of the formula (1c):
- wherein R1 and h are as defined above, in a fluorine containing aromatic compound to obtain a compound of the formula (1d):
- wherein Rf, PFPE, Q, Y1, Z, R1, e, f, g and h are as defined above, and then
- reacting the obtained compound with a compound of HX wherein X is as defined above.
18 more elements
Dependencies are inferred from the claim text.