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US5800926A Expired / Lapsed US ⏱️ 0.0 years remaining

Coating film having water repellency and low refractive index

Assignee: Nissan Chemical Corp
•
Filing: 1996-11-15
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Granted: 1998-09-01
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Expires: 2016-11-15
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Abstract

Abstract A coating film having a refractive index of from 1.28 to 1.38 and a contact angle of water of from 90° to 115°, adhered on a substrate surface, and prepared by reacting a particular tetraalkylsilicate, a particular fluorine-containing silicon compound, a particular hydroxy-containing compound, and oxalic acid in a particular range of ratios and in the absence of water, and under further specified reaction conditions.

Inventors

  • 👤 Tatsuya Nogami
  • 👤 Takakazu Nakada
  • 👤 Rie Sakai
  • 👤 Takeshi Hosoya

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 03:17
CPC Classifications
C; C09; C09D; C09D183/00; C09D183/04; C09D183/08; C03; C03C; C03C17/00; C03C17/34; C03C17/42; C08; C08G; C08G77/00; C08G77/04; C08G77/22; C08G77/24; C03C2217/00; C03C2217/70; C03C2217/73; C03C2217/732; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31609; Y10T428/31612; Y10T428/31652; Y10T428/31663; Y10T428/31667

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 338 words
A process for forming a coating film on a substrate surface, which comprises preparing a reaction mixture comprising a silicon compound (A) of the following formula (1): Si(OR).sub.4 ( 1) wherein R is a C 1-5 alkyl group, a silicon compound (B) of the following formula (2): CF.sub.3 (CF.sub.2)nCH.sub.2 CH.sub.2 Si(OR.sup.1).sub.3 ( 2) wherein R 1 is a C 1-5 alkyl group, and n is an integer of from 0 to 12, an alcohol (C) selected from the group consisting of diethylene glycol monomethyl ether, diethylene glycol monoethyl ether and an alcohol of the following formula (3): R.sup.2 CH.sub.2 OH (3) wherein R 2 is a hydrogen atom, or an unsubstituted C 1-12 alkyl group or a C 1-12 alkyl group substituted with hydroxy, methoxy or ethoxy, and oxalic acid (D), in a ratio of from 0.05 to 0.43 mol of the silicon compound (B) per mol of the silicon compound (A), in a ratio of from 0.5 to 100 mol of the alcohol (C) per mol of the total alkoxy groups contained in the silicon compounds (A) and (B), and in a ratio of from 0.2 to 2 mol of the oxalic acid (D) per mol of the total alkoxy groups contained in the silicon compounds (A) and (B); heating this reaction mixture at a temperature of from 50° to 180° C. until the total amount of the silicon compounds (A) and (B) remaining in the reaction mixture becomes at most 5 mol %, while maintaining a SiO 2 concentration of from 0.5 to 10 wt % as calculated from silicon atoms in the reaction mixture and maintaining absence of water, to form a polysiloxane solution; then coating a coating fluid comprising the polysiloxane solution on a substrate surface to form a coating; and heat-curing the coating at a temperature of from 80° to 450° C. to form a coating film having a refractive index of from 1.28 to 1.38 and a contact angle of water of from 90° to 115°, as adhered on the substrate surface.
Claim 2
Dependent Claim 338 words
A process for forming a coating film on a substrate surface, which comprises preparing a reaction mixture comprising a silicon compound (A) of the following formula (1): Si(OR).sub.4 ( 1) wherein R is a C 1-5 alkyl group, a silicon compound (B) of the following formula (2): CF.sub.3 (CF.sub.2)nCH.sub.2 CH.sub.2 Si(OR.sup.1).sub.3 ( 2) wherein R 1 is a C 1-5 alkyl group, and n is an integer of from 0 to 12, an alcohol (C) selected from the group consisting of diethylene glycol monomethyl ether, diethylene glycol monoethyl ether and an alcohol of the following formula (3): R.sup.2 CH.sub.2 OH (3) wherein R 2 is a hydrogen atom, or an unsubstituted C 1-12 alkyl group or a C 1-12 alkyl group substituted with hydroxy, methoxy or ethoxy, and oxalic acid (D), in a ratio of from 0.05 to 0.43 mol of the silicon compound (B) per mol of the silicon compound (A), in a ratio of from 0.5 to 100 mol of the alcohol (C) per mol of the total alkoxy groups contained in the silicon compounds (A) and (B), and in a ratio of from 0.2 to 2 mol of the oxalic acid (D) per mol of the total alkoxy groups contained in the silicon compounds (A) and (B); heating this reaction mixture at a temperature of from 50° to 180° C. until the total amount of the silicon compounds (A) and (B) remaining in the reaction mixture becomes at most 5 mol %, while maintaining a SiO 2 concentration of from 0.5 to 10 wt % as calculated from silicon atoms in the reaction mixture and maintaining absence of water, to form a polysiloxane solution; then coating a coating fluid comprising the polysiloxane solution on a substrate surface to form a coating; and heat-curing the coating at a temperature of from 80° to 450° C. to form a coating film having a refractive index of from 1.28 to 1.38 and a contact angle of water of from 90° to 115°, as adhered on the substrate surface.
Claim 3
Dependent Claim 28 words
The process according to claim 1, wherein the silicon compound (A) is at least one silicon compound selected from the group consisting of tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane and tetrabutoxysilane.
Claim 4
Dependent Claim 26 words
The process according to claim 1, wherein the silicon compound (A) is at least one silicon compound selected from the group consisting of tetramethoxysilane and tetraethoxysilane.
Claim 5
Dependent Claim 30 words
The process according to claim 1, wherein the silicon compound (B) is at least one silicon compound selected from the group consisting of 3,3,3-trifluoropropyltrimethoxysilane, 3,3,3-trifluoropropyltriethoxysilane, 8,8,8,7,7,6,6,5,5,4,4,3,3-tridecafluorooctyltrimethoxysilane, 8,8,8,7,7,6,6,5,5,4,4,3,3-tridecafluorooctyltriethoxysilane, 10,10,10,9,9,8,8,7,7,6,6,5,5,4,4,3,3-heptadecafluorodecyltrimethoxysilane and 10,10,10,9,9,8,8,7,7,6,6,5,5,4,4,3,3-heptadecafluorodecyltriethoxysilane.
Claim 6
Dependent Claim 50 words
The process according to claim 1, wherein the alcohol (C) is at least one alcohol selected from the group consisting of methanol, ethanol, propanol, n-butanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether and propylene glycol monoethyl ether.
Claim 7
Dependent Claim 12 words
The process according to claim 1, wherein the alcohol (C) is ethanol.
Claim 8
Dependent Claim 99 words
The process according to claim 1, wherein at least one alkyl alkoxysilane selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, butyltriethoxysilane, pentyltrimethoxysilane, pentyltriethoxysilane, heptyltrimethoxysilane, heptyltriethoxysilane, octyltrimethoxysilane, octyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropyltriethoxysilane, dimethyldimethoxysilane and dimethyldiethoxysilane, is incorporated as a modifier (E) in an amount of from 0.02 to 0.2 mol per mol of the silicon compound (A) in addition to the silicon compound (A), the silicon compound (B), the alcohol (C) and the oxalic acid (D), in the preparation of the reaction mixture.
Claim 9
Dependent Claim 47 words
The process according to claim 1, wherein at least one sol selected from the group consisting of a silica sol, an alumina sol, a titania sol, a zirconia sol, a magnesium fluoride sol and a ceria sol, is incorporated as an additive (F) to the coating fluid.
Claim 10
Dependent Claim 47 words
The process according to claim 7, wherein at least one sol selected from the group consisting of a silica sol, an alumina sol, a titania sol, a zirconia sol, a magnesium fluoride sol and a ceria sol, is incorporated as an additive (F) to the coating fluid.
Claim 11
Dependent Claim 327 words
A coating film having a refractive index of from 1.28 to 1.38 and a contact angle of water of from 90° to 115°, which is formed as adhered on a substrate surface, by preparing a reaction mixture comprising a silicon compound (A) of the following formula (1): Si(OR).sub.4 ( 1) wherein R is a C 1-5 alkyl group, a silicon compound (B) of the following formula (2): CF.sub.3 (CF.sub.2)nCH.sub.2 CH.sub.2 Si(OR.sup.1).sub.3 ( 2) wherein R 1 is a C 1-5 alkyl group, and n is an integer of from 0 to 12, an alcohol (C) selected from the group consisting of diethylene glycol monomethyl ether, diethylene glycol monoethyl ether and an alcohol of the following formula (3): R.sup.2 CH.sub.2 OH (3) wherein R 2 is a hydrogen atom, or an unsubstituted C 1-12 alkyl group or a C 1-12 alkyl group substituted with hydroxy, methoxy or ethoxy, and oxalic acid (D), in a ratio of from 0.05 to 0.43 mol of the silicon compound (B) per mol of the silicon compound (A), in a ratio of from 0.5 to 100 mol of the alcohol (C) per mol of the total alkoxy groups contained in the silicon compounds (A) and (B), and in a ratio of from 0.2 to 2 mol of the oxalic acid (D) per mol of the total alkoxy groups contained in the silicon compounds (A) and (B); heating this reaction mixture at a temperature of from 50° to 180° C. until the total amount of the silicon compounds (A) and (B) remaining in the reaction mixture becomes at most 5 mol %, while maintaining a SiO 2 concentration of from 0.5 to 10 wt % as calculated from silicon atoms in the reaction mixture and maintaining absence of water, to form a polysiloxane solution; then coating a coating fluid comprising the polysiloxane solution on a substrate surface to form a coating; and heat-curing the coating at a temperature of from 80° to 450° C.
Claim 12
Dependent Claim 327 words
A coating film having a refractive index of from 1.28 to 1.38 and a contact angle of water of from 90° to 115°, which is formed as adhered on a substrate surface, by preparing a reaction mixture comprising a silicon compound (A) of the following formula (1): Si(OR).sub.4 ( 1) wherein R is a C 1-5 alkyl group, a silicon compound (B) of the following formula (2): CF.sub.3 (CF.sub.2)nCH.sub.2 CH.sub.2 Si(OR.sup.1).sub.3 ( 2) wherein R 1 is a C 1-5 alkyl group, and n is an integer of from 0 to 12, an alcohol (C) selected from the group consisting of diethylene glycol monomethyl ether, diethylene glycol monoethyl ether and an alcohol of the following formula (3): R.sup.2 CH.sub.2 OH (3) wherein R 2 is a hydrogen atom, or an unsubstituted C 1-12 alkyl group or a C 1-12 alkyl group substituted with hydroxy, methoxy or ethoxy, and oxalic acid (D), in a ratio of from 0.05 to 0.43 mol of the silicon compound (B) per mol of the silicon compound (A), in a ratio of from 0.5 to 100 mol of the alcohol (C) per mol of the total alkoxy groups contained in the silicon compounds (A) and (B), and in a ratio of from 0.2 to 2 mol of the oxalic acid (D) per mol of the total alkoxy groups contained in the silicon compounds (A) and (B); heating this reaction mixture at a temperature of from 50° to 180° C. until the total amount of the silicon compounds (A) and (B) remaining in the reaction mixture becomes at most 5 mol %, while maintaining a SiO 2 concentration of from 0.5 to 10 wt % as calculated from silicon atoms in the reaction mixture and maintaining absence of water, to form a polysiloxane solution; then coating a coating fluid comprising the polysiloxane solution on a substrate surface to form a coating; and heat-curing the coating at a temperature of from 80° to 450° C.
Claim 13
Dependent Claim 29 words
The coating film according to claim 10, wherein the silicon compound (A) is at least one silicon compound selected from the group consisting of tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane and tetrabutoxysilane.
Claim 14
Dependent Claim 27 words
The coating film according to claim 10, wherein the silicon compound (A) is at least one silicon compound selected from the group consisting of tetramethoxysilane and tetraethoxysilane.
Claim 15
Dependent Claim 31 words
The coating film according to claim 10, wherein the silicon compound (B) is at least one silicon compound selected from the group consisting of 3,3,3-trifluoropropyltrimethoxysilane, 3,3,3-trifluoropropyltriethoxysilane, 8,8,8,7,7,6,6,5,5,4,4,3,3-tridecafluorooctyltrimethoxysilane, 8,8,8,7,7,6,6,5,5,4,4,3,3-tridecafluorooctyltriethoxysilane, 10,10,10,9,9,8,8,7,7,6,6,5,5,4,4,3,3-heptadecafluorodecyltrimethoxysilane and 10,10,10,9,9,8,8,7,7,6,6,5,5,4,4,3,3-heptadecafluorodecyltriethoxysilane.
Claim 16
Dependent Claim 51 words
The coating film according to claim 10, wherein the alcohol (C) is at least one alcohol selected from the group consisting of methanol, ethanol, propanol, n-butanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether and propylene glycol monoethyl ether.
Claim 17
Dependent Claim 13 words
The coating film according to claim 10, wherein the alcohol (C) is ethanol.
Claim 18
Dependent Claim 100 words
The coating film according to claim 10, wherein at least one alkyl alkoxysilane selected from the group consisting of methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, propyltrimethoxysilane, propyltriethoxysilane, butyltrimethoxysilane, butyltriethoxysilane, pentyltrimethoxysilane, pentyltriethoxysilane, heptyltrimethoxysilane, heptyltriethoxysilane, octyltrimethoxysilane, octyltriethoxysilane, dodecyltrimethoxysilane, dodecyltriethoxysilane, hexadecyltrimethoxysilane, hexadecyltriethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropyltriethoxysilane, dimethyldimethoxysilane and dimethyldiethoxysilane, is incorporated as a modifier (E) in an amount of from 0.02 to 0.2 mol per mol of the silicon compound (A) in addition to the silicon compound (A), the silicon compound (B), the alcohol (C) and the oxalic acid (D), in the preparation of the reaction mixture.
Claim 19
Dependent Claim 48 words
The coating film according to claim 10, wherein at least one sol selected from the group consisting of a silica sol, an alumina sol, a titania sol, a zirconia sol, a magnesium fluoride sol and a ceria sol, is incorporated as an additive (F) to the coating fluid.
Claim 20
Dependent Claim 48 words
The coating film according to claim 16, wherein at least one sol selected from the group consisting of a silica sol, an alumina sol, a titania sol, a zirconia sol, a magnesium fluoride sol and a ceria sol, is incorporated as an additive (F) to the coating fluid.

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