(EP3315579) Surface treatment agent including perfluoro(poly)ether group-containing silane compound 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(EP3315579) Surface treatment agent including perfluoro(poly)ether group-containing silane compound
公开号/公开日
EP3315579EP3315579 / 2018-05-022019-02-20
申请号/申请日
EP16814357 / 2016-06-21
发明人
KATSUKAWA KENICHIMITSUHASHI HISASHIYOSHIDA TOMOHIRONOSE MASATOSHINAMIKAWA TAKASHI;
申请人
DAIKIN INDUSTRIES;
主分类号
IPC分类号
C07F-007/18 C08G-065/00 C08G-065/336 C09D-005/16 C09D-171/00 C09D-183/06 C09D-183/12 C09K-003/18
摘要
(EP3315579) The present invention relates to a surface-treating agent comprising at least one perfluoro(poly)ether group containing silane compound of the formula (1): wherein each of symbols is as defined in the description, wherein a number average molecular weight of the perfluoro(poly)ether group containing silane compound is 3000 or more and 6000 or less, and 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.
机翻摘要
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地址
代理人
(EP3315579) Hoffmann Eitle ; Patent- und Rechtsanwälte PartmbB ([DE]) Reg. Nb: 100061036
代理机构
;
优先权号
2015JP-0127889 2016WO-JP68412
主权利要求
(EP3315579) 1. 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, b, c and d are each independently an integer of 0 to 90, 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;  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 OR4;  R4 is each independently at each occurrence a substituted or unsubstituted C1-12 alkyl 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  a number average molecular weight of the perfluoro(poly)ether group containing silane compound is 3000 or more and 6000 or less, and  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. 2. The surface-treating agent according to claim 1 wherein the number average molecular weight of the perfluoro(poly)ether group containing silane compound is 3000 or more and 5000 or less. 3. The surface-treating agent according to claim 1 or 2 wherein 90 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. 4. The surface-treating agent according to any one of claims 1-3 wherein 50 mol% or more of the perfluoro(poly)ether group containing silane compound contained in the surface-treating agent is the compound wherein g is 3 or more. 5. The surface-treating agent according to any one of claims 1-4 wherein 80 mol% or more of the perfluoro(poly)ether group containing silane compound contained in the surface-treating agent is the compound wherein g is 3 or more. 6. The surface-treating agent according to any one of claims 1-5 wherein 60 mol% or more of the perfluoro(poly)ether group containing silane compound contained in the surface-treating agent is the compound wherein g is 2 or more and 4 or less. 7. The surface-treating agent according to any one of claims 1-6 wherein 75 mol% or more of the perfluoro(poly)ether group containing silane compound contained in the surface-treating agent is the compound wherein g is 2 or more and 4 or less. 8. The surface-treating agent according to any one of claims 1-7 wherein polydispersity of g is more than 1.0 and less than 2.0. 9. The surface-treating agent according to any one of claims 1-8 wherein Rf is a perfluoroalkyl group having 1 to 10 carbon atoms. 10. The surface-treating agent according to any one of claims 1-9 wherein PFPE is a group:         -(OCF2CF2CF2)b- wherein b is an integer of 1 or more and 40 or less. 11. The surface-treating agent according to any one of claims 1-9 wherein PFPE is a group         -(OCF2CF2CF2CF2)a-(OCF2CF2CF2)b-(OCF2CF2)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 1 to 90, 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. 12. The surface-treating agent according to any one of claims 1-11, further comprising a solvent. 13. The surface-treating agent according to any one of claims 1-12, further comprising one or more other components selected from the group consisting of a fluorine-containing oil, a silicone oil and a catalyst. 14. The surface-treating agent according to claim 13 wherein the fluorine-containing oil is one or more compounds of the formula (2):         Rf1-(OC4F8)a'-(OC3F6)b'-(OC2F4)c'-(OCF2)d'-Rf2     (2) wherein:  Rf1 is an alkyl group having 1 to 16 carbon atoms which may be substituted by one or more fluorine atoms;  Rf2 is an alkyl group having 1 to 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 each independently an integer of 0 to 300, 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. 15. The surface-treating agent according to claim 13 or 14 wherein the fluorine-containing oil is one or more compounds of the formula (2a) or (2b):         Rf1-(OCF2CF2CF2)b'-Rf2     (2a) Rf1-(OCF2CF2CF2CF2)a'-(OCF2CF2CF2)b'-(OCF2CF2)c'-(OCF2)d'-Rf2 (2b) wherein:  Rf1 is an alkyl group having 1 to 16 carbon atoms which may be substituted by one or more fluorine atoms;  Rf2 is an alkyl group having 1 to 16 carbon atoms which may be substituted by one or more fluorine atoms, a fluorine atom or a hydrogen atom;  in the formula (2a), b' is an integer of 1 or more and 300 or less;  in the formula (2b), a' and b' is each independently an integer of 0 to 30, c' and d' is each independently an integer of 1 to 300, 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. 16. The surface-treating agent according to any one of claims 1-15 which is used as an antifouling-coating agent or a waterproof-coating agent. 17. A pellet comprising the surface-treating agent according to any one of claims 1-16. 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 any one of claims 1-16. 19. The article according to claim 18 wherein the base material is a glass. 20. The article according to claim 18 or 19 wherein the article is an optical member. 21. The article according to any one of claims 18-20 wherein the article is a display. 22. A process for preparing a surface-treating agent comprising 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, b, c and d are each independently an integer of 0 to 90, 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;  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 OR4;  R4 is each independently at each occurrence a substituted or unsubstituted C1-12 alkyl 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 a number average molecular weight of the perfluoro(poly)ether group containing silane compound is 3000 or more and 6000 or less, and  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, comprising the steps 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. A process for preparing a surface-treating agent comprising 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, b, c and d are each independently an integer of 0 to 90, 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;  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 OR4;  R4 is each independently at each occurrence a substituted or unsubstituted C1-12 alkyl 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; wherein a number average molecular weight of the perfluoro(poly)ether group containing silane compound is 3000 or more and 6000 or less, and  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, comprising the steps 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. 24. The process according to claim 22 or 23 wherein the fluorine containing aromatic compound is selected from the group consisting of perfluorobenzene, pentafluorobenzene, 1,2,3,4-tetrafluorobenzene, 1,2,3,5-tetrafluorobenzene, 1,2,4,5-tetrafluorobenzene, 1,2,3-trifluorobenzene, 1,2,4-trifluorobenzene, 1,3,5-trifluorobenzene, benzotrifluoride, fluorobenzene, 1-chloro-2-fluorobenzene, 1-chloro-3-fluorobenzene, 1-chloro-4-fluorobenzene, 2,6-dichlorofluorobenzene, 1-fluoro-3-(trifluoromethoxy)benzene, 1-fluoro-2,4-dinitrobenzene, 2,4-dimethoxy-1-fluorobenzene, 1-fluoro-4-nitrobenzene, 2-fluorotoluene, 3-fluorotoluene, 4-fluorotoluene, 3-fluorobenzotrifluoride, 1-chloro-2,4-difluorobenzene, 1-chloro-3,4-difluorobenzene, 1-chloro-3,5-difluorobenzene, 2-chloro-1,3-difluorobenzene, chloropentafluorobenzene, 2,4-dichlorofluorobenzene, 2,5-dichlorofluorobenzene, 2,6-dichlorofluorobenzene, 1,2-dichloro-4-fluorobenzene, 1,3-dichloro-5-fluorobenzene, 1,3-dichloro-2,4,6-trifluorobenzene, 3,4-difluorobenzonitrile, 3,5-difluorobenzonitrile, 3,4-difluoronitrobenzene, 1-ethoxy-2,3-difluorobenzene, 1,2-dicyano-4,5-difluorobenzene, 1-acetoxy-3-fluorobenzene, 1-acetoxy-4-fluorobenzene, 1-acetonyl-4-fluorobenzene, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 4-fluoro-o-xylene, pentafluoroanisole, tetrafluorophthalonitrile, 2-trifluoromethylbenzal chloride, 3-trifluoromethylbenzal chloride, 4-trifluoromethylbenzal chloride, methyl 3-(trifluoromethyl)benzoate, difluorobenzonitrile, bistrifluoromethyl benzonitrile, 4-trifluoromethyl benzonitrile, aminobenzotrifluoride, and trifluoromethylaniline. 25. The process according to any one of claims 22-24 wherein the fluorine containing aromatic compound is a fluorine containing aromatic compound having 0 to 3 debyes of polarizability. 26. The process according to any one of claims 22-25 wherein the fluorine containing aromatic compound is selected from the group consisting of benzotrifluoride, difluorobenzonitrile, and bistrifluoromethyl benzonitrile. 27. 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, b, c and d are each independently an integer of 0 to 90, 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;  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 OR4;  R4 is each independently at each occurrence a substituted or unsubstituted C1-12 alkyl 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 a number average molecular weight of the perfluoro(poly)ether group containing silane compound is 3000 or more and 6000 or less, and  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, wherein the perfluoro(poly)ether group containing silane compound of the formula (1) is prepared by 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. 28. 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, b, c and d are each independently an integer of 0 to 90, 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;  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 OR4;  R4 is each independently at each occurrence a substituted or unsubstituted C1-12 alkyl 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; wherein a number average molecular weight of the perfluoro(poly)ether group containing silane compound is 3000 or more and 6000 or less, and  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, wherein the perfluoro(poly)ether group containing silane compound of the formula (1') is prepared by 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. 29. The surface-treating agent according to claim 27 or 28 wherein the fluorine containing aromatic compound is selected from the group consisting of perfluorobenzene, pentafluorobenzene, 1,2,3,4-tetrafluorobenzene, 1,2,3,5-tetrafluorobenzene, 1,2,4,5-tetrafluorobenzene, 1,2,3-trifluorobenzene, 1,2,4-trifluorobenzene, 1,3,5-trifluorobenzene, benzotrifluoride, fluorobenzene, 1-chloro-2-fluorobenzene, 1-chloro-3-fluorobenzene, 1-chloro-4-fluorobenzene, 2,6-dichlorofluorobenzene, 1-fluoro-3-(trifluoromethoxy)benzene, 1-fluoro-2,4-dinitrobenzene, 2,4-dimethoxy-1-fluorobenzene, 1-fluoro-4-nitrobenzene, 2-fluorotoluene, 3-fluorotoluene, 4-fluorotoluene, 3-fluorobenzotrifluoride, 1-chloro-2,4-difluorobenzene, 1-chloro-3,4-difluorobenzene, 1-chloro-3,5-difluorobenzene, 2-chloro-1,3-difluorobenzene, chloropentafluorobenzene, 2,4-dichlorofluorobenzene, 2,5-dichlorofluorobenzene, 2,6-dichlorofluorobenzene, 1,2-dichloro-4-fluorobenzene, 1,3-dichloro-5-fluorobenzene, 1,3-dichloro-2,4,6-trifluorobenzene, 3,4-difluorobenzonitrile, 3,5-difluorobenzonitrile, 3,4-difluoronitrobenzene, 1-ethoxy-2,3-difluorobenzene, 1,2-dicyano-4,5-difluorobenzene, 1-acetoxy-3-fluorobenzene, 1-acetoxy-4-fluorobenzene, 1-acetonyl-4-fluorobenzene, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 4-fluoro-o-xylene, pentafluoroanisole, tetrafluorophthalonitrile, 2-trifluoromethylbenzal chloride, 3-trifluoromethylbenzal chloride, 4-trifluoromethylbenzal chloride, methyl 3-(trifluoromethyl)benzoate, difluorobenzonitrile, bistrifluoromethyl benzonitrile, 4-trifluoromethyl benzonitrile, aminobenzotrifluoride, and trifluoromethylaniline. 30. The surface-treating agent according to any one of claims 27-29 wherein the fluorine containing aromatic compound is a fluorine containing aromatic compound having 0 to 3 debyes of polarizability. 31. The surface-treating agent according to any one of claims 27-30 wherein the fluorine containing aromatic compound is selected from the group consisting of benzotrifluoride, difluorobenzonitrile, and bistrifluoromethyl benzonitrile.
法律状态
PENDING
专利类型码
A1A4
国别省市代码
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