US5800926A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Coating film having water repellency and low refractive index
Assignee: Nissan Chemical Corp
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Filing: 1996-11-15
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Granted: 1998-09-01
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Expires: 2016-11-15
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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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2001-08-31 | 2002-03-02 | 2002-09-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2005-08-31 | 2006-03-02 | 2006-09-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2009-08-31 | 2010-03-02 | 2010-09-01 | $7700.00 | Window Closed / Lapsed |