CA1105784A - Abrasion-resistant lenses and process of making - Google Patents
Abrasion-resistant lenses and process of makingInfo
- Publication number
- CA1105784A CA1105784A CA293,672A CA293672A CA1105784A CA 1105784 A CA1105784 A CA 1105784A CA 293672 A CA293672 A CA 293672A CA 1105784 A CA1105784 A CA 1105784A
- Authority
- CA
- Canada
- Prior art keywords
- coating
- tie
- abrasion
- lens
- lenses
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00865—Applying coatings; tinting; colouring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Eyeglasses (AREA)
- Paints Or Removers (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Abstract
AO-3163 AHS/sam 1/21/77 ABRASION-RESISTANT LENSES AND PROCESS OF MAKING Plastic substrates of optical elements having surfaces coated with the abrasion-resistant coating compositions described in U.S. Patent No. 3,986,997 are improved by utilizing a tiecoat comprising an A-alkylenealkoxysilane where A contains a group reactive with reactive with the substrate. For some substrates, particularly polycarbonate lenses, the coating process is substantially simplified by reducing criticality of conditions when the tie-coat of the present invention is used then when the process of the aforementioned patent is followed with the tie-coats conventionally used and disclosed therein.
Description
Background of the Invention Field of the Invention:
This invention relates to a novel optical element particularly a novel lens of an organic synthetic polymer having a transparent abrasion-resistant coating adhered thereto and to novel and improved metllods oE making such coated elements.
Description of the Pr-ior ~rt:
__ ~ leretofore, methods have been proposed for improving the surface characterist:ics and scratch resistance of solid organic polymers particularly transparent polymeric materials. In U.S.
Patent Nos. 2,404,426 and 2,404,357, methods are disclosed for coating synthetic polymers particularly methylmethacrylate polymers using an ethyl silicate. It is disclosed that the ethyl silicate can be cross-linked using an amine present in combination with moisture during the drying, baking or aging operations.
Abrasion-resistant coatings are also disclosed in U.S.
Patent No. 3,700,487 in which there is claimed a polycarbonate substrate coated wi~h a lightly cross-linked polyvinyl alcohol coating and U.S. Patent No. 3,484,157 in which there is disclosed an abrasion-resistant plastic transparent optical element having ~' ~j~f jl/~;<;~ -2-~ . . .
,'' . ' : .' ' :' ' ~ ' ~, ~
7~
a directly adhering coating comprising a vinyl po]~ner cross-linked with a dialdehyde cross-linking agent.
Previous attempts to provide an abrasion-resistant coating have failed to provide a sufficiently ahrasion-resistant coating which can be applied from a water solution by a dipping operation in which a subs-tantial thickness of coating is applied to the synthetic organic kase material. Prior art coatings have been limited to a relatively thin coating of ahout 1 micron.
Those coatings applied by the technique of spin coating, a method well-known to those skilled in the ar-t are especially limited by the thickness of coating which can be applied in one application.
The two proble~s are solyed by the method.s and compositions of the present invention. Greater abrasion resistance is provided by the use of a relativelv thick coating on the svnthetic orqanic polymer substrate. In addition, the methods and composition of the present invention have overcome the discoloration of some prior art coatings when applied in successive layers. The ~istinct yellow coloration of prior art coatings is objectiona~le particularly in an optical element.
U. S. Patent No. 3,986,997 discloses pigment-free coating compositions used to provide abrasion-resistant coatin~s, particularly for optical materials. This patent aoes not describe the tie-coat of the present invention nor a tie-coat similar thereto. Example ~ of the patent teaches utilizing a tie-coat bm: -' , 5~
prepared by soakiny the substrate in 10~ solution of potassium hydroxide overnight or priming the substrate with a sil~ne-modified epoxy primer. In addition, although not described in the patent, it is necessary to carefully control the humidity during the coating of the optical elements according to the process of the patent in order to prepare a product having optical properties commercially acceptable.
Summary of the' Inv'en*ion -There is provided a process of coating pla.stic optical substrates, particularly polycarbonate ophthalmic lenses and poly diethyleneglycol bis allyl carbonate ophthalmic lenses using an organoalkoxysilane of the forrnu.la ARIsI tOR 2) a(R3)b(OH)C
wherein A is ~H 2 r NHR 3 or NHR ~NII 2 when the lens is a polycarbonate and is CH2-CH- when the lens is a poly diethyleneglycol bis allyl carbonate, Rl is an alkylene having 2 to 10 ~arbons, R2 and R3 are alkyls having 1 to ~ carbons, a is 1, 2 or 3, b'is 0, 1 or 2, c is 0, 1 or 2 and a+b~c=3. A preferred tie-coat for polycarbonate lenses is the commercially availahl0 gamma-Aminopropyltriethoxy-silane. This material is commercially available from ~nion ; Carbide under the tradename A-llO0 and a related material is available from Dow-Corning under the tradename Z-6020 ~hich has the following formula NH2(CH2) 2NH(CH2) 3Si(OCH~ 3.
bm:
.
, . . ...
: : ' ' , : . :
: . ,, :
7i~
These rnater:ials are ~nown coupling a~ents for pol~carbonate laminates with glass, such as fibers or sheets. For poly diethyleneglycol bis allyl carbonate lenses (C~-39 ) tie-coats with epoxy reactive groups are recommended. Examples of such materials are Union Carbide material A-1~7 and Dow-Corning material Z-60~0. Both o* these materials are gamma-Glycidoxy-propyltrimetho~ysilane.
The tie-coat is applied in any conventional manner from a dilute solution, preferably containing less than 20% of the active material The application of the tie-coat should he in a manner known to those skilled in the art which will result in a minimum effective tie-coat thickness. While coating thicknesses have not been measured, they are believed to be in the order of 1-10 moleculcs. One preferred solution used in an immersion process consists of 10% gamma-Aminopropyltriethoxysilane, 85%
ethyl alcohol and 5% water. Suitable thicknesses using this solution are obtained when the lenses are immersed *or about one minute. IIowever, immersion times exceeding one minute have been found to produce satisEactory coatings.
U. S. Patent No. 3,986,997 discloses a coating composition and a number of specific examples thereof. These coati~ng compositions are availahle from Dow-Corning under the tradenames ARC and C~RESIN. l'he Nov.~Dec. 1976 issue of ~,~
bm:
TERI~L NEWS had an article regarding an award in recognition of this significant new technical product.
The abrasion-resistant coating is a pigment free aqueous coating composition comprising a dispersion of colloidal silica in lower aliphatic alcohol-water solution of the partial condensate of a silanol of the formula RSi(OH)3 in which R
is selected from the group consisting of alkyl radicals of 1 to 3 inclusive carbon atoms, the vinyl radical, the 3,3,3-trifluoropropyl radical, the gamma-g~ycidoxypropyl radical and the gamma-methacryloxypropyl radical, at least 70 weight percent of the silanol being CH3Si(OH) 3, said composition containing 10 to 50 weight percent solids consisting essentially of 10 to 70 weight percent colloidal silica and 30 to 90 weight percent of the partial condensate.
Example 1 Injection molded polycarbonate lenses meeting ophthalmic quality standards were treated by immersion at room temperature in a tie-coat solution containing 10% gamma-amino propyl triethoxysilane, 85% ethyl alcohol and 5% water for one minute.
The lenses were then removed from the silane solution, rinsed in water and dried.
The period of immersion in the silane solution is not particularly critical. Likewise, the interval between the removal of the lens from the silane solution and rinsing is not critical. In fact, the lenses may dry before rinsing.
However, a delay of a day or more could cause the finished coating to be of undue thickness and/or retain an undesirable haze.
We have found that a water rinse subsequent to immersion ~ .
l Jl/ ~ -6--":
" ' , , :
7~f~
in the silane solution may be essential for re.-no-ving haze in the coating. Thls haze is objectionable in ophthalmic products and a rinse is very desirable. However, in products of limited transmission, such as sunglasses, such haze may not be objectionable and, thus, the water bath may be optional.
The thickness of the tie-coat coating is not critical since only those molecules reacted with the polycarbonate substrate or reacted in turn with a molecule thus reacted, remain as a part of the coating following the rinse. Thicker coatings are undesirable only to the extent they affect the haze of the lens.
~.
: ~ .
-6a-~$'~
The lenses were then coated with an abrasion-resistant coating obtained from Dow-Corning and identified as C-RESIN. Dow-Corning personnel advised the inventors that the material was covered by U.S. Patent No. 3,986,997. The material was applied to the lenses by dipping in a solution. The C-RESIN
was filtered upon receipt, placed in a con-tainer and -the lenses were immersed and withdrawn a-t a controlled rate. The rate of withdrawal de~ines the coating thickness. The rate of withdrawal may be varied from 1-20 inches per minute. The preferred rates being in the order of 4-1~ inches per minu-te. The lenses of this examples were withdrawn at the rate of 7 1/2 inches per minuie. The lenses were then treated at room temperature.
Following drying, they were cured in an air-circulating oven for eight hours at 250 F. The properties of these lenses, namely, abrasion-resistance, haze and resistance to thermal shock were undetectably equivalent to similarly coated polycarbonate lenses wherein the abrasion-resistant coating (C-RESIN) was applied under conditions of controlled humidity/ i.e. 30~ relative humidity or less.
Example 2 A second group of polycarbonate lenses were treated with the tie-coat solution according to the solution set forth in Example 1. After rinsin~ and drying, the tie-coated lenses were treated by immersion in the Dow-Corning ARC composition and withdrawn at a controlled rate of 7 1/2 inches per minute.
The coated lenses were then permitted to dry at room temperature and subsequently placed in an air-circulating oven for eight bm:
, . : , . , 7~
hours at 250~ F. The lenses were of acceptahle ophthalmic quality and like those of Example 1, ahrasion resistance, haze and resistance to thermal shock were substantially identical with lenses similarly coated in an environment controlled by humidity.
Polycarbonate lenses coated according to the description in U.S. Patent No. ~,986,997 will only provide comparable adhesion if the polycarhonate lenses are thoroughly dried (four hours minimum in an air-circulating oven at 240~ E) and the abrasion-resistant coating is applied in an environment having controlled humidity (30%, or less relative humidity).
Example 3 Ophthalmic CR-39~ lenses are immersed for ahout one minute in a 10% solution of gamma-glycidoxypropyltrimethoxysilane in an aqueous-ethanol mixture having one part water to 17 parts ethyl alcohol adjusted to a pH of 3 to 5 by the addition of acetic acid. After removal, the lenses are rinsed and dried.
` The CR-39~ tie-coated lenses have the abrasion-resistant ARC
coating applied, dried and cured following the procedure o~
; 20 Example 2.
.
~8 bm:
, ~ , , '
This invention relates to a novel optical element particularly a novel lens of an organic synthetic polymer having a transparent abrasion-resistant coating adhered thereto and to novel and improved metllods oE making such coated elements.
Description of the Pr-ior ~rt:
__ ~ leretofore, methods have been proposed for improving the surface characterist:ics and scratch resistance of solid organic polymers particularly transparent polymeric materials. In U.S.
Patent Nos. 2,404,426 and 2,404,357, methods are disclosed for coating synthetic polymers particularly methylmethacrylate polymers using an ethyl silicate. It is disclosed that the ethyl silicate can be cross-linked using an amine present in combination with moisture during the drying, baking or aging operations.
Abrasion-resistant coatings are also disclosed in U.S.
Patent No. 3,700,487 in which there is claimed a polycarbonate substrate coated wi~h a lightly cross-linked polyvinyl alcohol coating and U.S. Patent No. 3,484,157 in which there is disclosed an abrasion-resistant plastic transparent optical element having ~' ~j~f jl/~;<;~ -2-~ . . .
,'' . ' : .' ' :' ' ~ ' ~, ~
7~
a directly adhering coating comprising a vinyl po]~ner cross-linked with a dialdehyde cross-linking agent.
Previous attempts to provide an abrasion-resistant coating have failed to provide a sufficiently ahrasion-resistant coating which can be applied from a water solution by a dipping operation in which a subs-tantial thickness of coating is applied to the synthetic organic kase material. Prior art coatings have been limited to a relatively thin coating of ahout 1 micron.
Those coatings applied by the technique of spin coating, a method well-known to those skilled in the ar-t are especially limited by the thickness of coating which can be applied in one application.
The two proble~s are solyed by the method.s and compositions of the present invention. Greater abrasion resistance is provided by the use of a relativelv thick coating on the svnthetic orqanic polymer substrate. In addition, the methods and composition of the present invention have overcome the discoloration of some prior art coatings when applied in successive layers. The ~istinct yellow coloration of prior art coatings is objectiona~le particularly in an optical element.
U. S. Patent No. 3,986,997 discloses pigment-free coating compositions used to provide abrasion-resistant coatin~s, particularly for optical materials. This patent aoes not describe the tie-coat of the present invention nor a tie-coat similar thereto. Example ~ of the patent teaches utilizing a tie-coat bm: -' , 5~
prepared by soakiny the substrate in 10~ solution of potassium hydroxide overnight or priming the substrate with a sil~ne-modified epoxy primer. In addition, although not described in the patent, it is necessary to carefully control the humidity during the coating of the optical elements according to the process of the patent in order to prepare a product having optical properties commercially acceptable.
Summary of the' Inv'en*ion -There is provided a process of coating pla.stic optical substrates, particularly polycarbonate ophthalmic lenses and poly diethyleneglycol bis allyl carbonate ophthalmic lenses using an organoalkoxysilane of the forrnu.la ARIsI tOR 2) a(R3)b(OH)C
wherein A is ~H 2 r NHR 3 or NHR ~NII 2 when the lens is a polycarbonate and is CH2-CH- when the lens is a poly diethyleneglycol bis allyl carbonate, Rl is an alkylene having 2 to 10 ~arbons, R2 and R3 are alkyls having 1 to ~ carbons, a is 1, 2 or 3, b'is 0, 1 or 2, c is 0, 1 or 2 and a+b~c=3. A preferred tie-coat for polycarbonate lenses is the commercially availahl0 gamma-Aminopropyltriethoxy-silane. This material is commercially available from ~nion ; Carbide under the tradename A-llO0 and a related material is available from Dow-Corning under the tradename Z-6020 ~hich has the following formula NH2(CH2) 2NH(CH2) 3Si(OCH~ 3.
bm:
.
, . . ...
: : ' ' , : . :
: . ,, :
7i~
These rnater:ials are ~nown coupling a~ents for pol~carbonate laminates with glass, such as fibers or sheets. For poly diethyleneglycol bis allyl carbonate lenses (C~-39 ) tie-coats with epoxy reactive groups are recommended. Examples of such materials are Union Carbide material A-1~7 and Dow-Corning material Z-60~0. Both o* these materials are gamma-Glycidoxy-propyltrimetho~ysilane.
The tie-coat is applied in any conventional manner from a dilute solution, preferably containing less than 20% of the active material The application of the tie-coat should he in a manner known to those skilled in the art which will result in a minimum effective tie-coat thickness. While coating thicknesses have not been measured, they are believed to be in the order of 1-10 moleculcs. One preferred solution used in an immersion process consists of 10% gamma-Aminopropyltriethoxysilane, 85%
ethyl alcohol and 5% water. Suitable thicknesses using this solution are obtained when the lenses are immersed *or about one minute. IIowever, immersion times exceeding one minute have been found to produce satisEactory coatings.
U. S. Patent No. 3,986,997 discloses a coating composition and a number of specific examples thereof. These coati~ng compositions are availahle from Dow-Corning under the tradenames ARC and C~RESIN. l'he Nov.~Dec. 1976 issue of ~,~
bm:
TERI~L NEWS had an article regarding an award in recognition of this significant new technical product.
The abrasion-resistant coating is a pigment free aqueous coating composition comprising a dispersion of colloidal silica in lower aliphatic alcohol-water solution of the partial condensate of a silanol of the formula RSi(OH)3 in which R
is selected from the group consisting of alkyl radicals of 1 to 3 inclusive carbon atoms, the vinyl radical, the 3,3,3-trifluoropropyl radical, the gamma-g~ycidoxypropyl radical and the gamma-methacryloxypropyl radical, at least 70 weight percent of the silanol being CH3Si(OH) 3, said composition containing 10 to 50 weight percent solids consisting essentially of 10 to 70 weight percent colloidal silica and 30 to 90 weight percent of the partial condensate.
Example 1 Injection molded polycarbonate lenses meeting ophthalmic quality standards were treated by immersion at room temperature in a tie-coat solution containing 10% gamma-amino propyl triethoxysilane, 85% ethyl alcohol and 5% water for one minute.
The lenses were then removed from the silane solution, rinsed in water and dried.
The period of immersion in the silane solution is not particularly critical. Likewise, the interval between the removal of the lens from the silane solution and rinsing is not critical. In fact, the lenses may dry before rinsing.
However, a delay of a day or more could cause the finished coating to be of undue thickness and/or retain an undesirable haze.
We have found that a water rinse subsequent to immersion ~ .
l Jl/ ~ -6--":
" ' , , :
7~f~
in the silane solution may be essential for re.-no-ving haze in the coating. Thls haze is objectionable in ophthalmic products and a rinse is very desirable. However, in products of limited transmission, such as sunglasses, such haze may not be objectionable and, thus, the water bath may be optional.
The thickness of the tie-coat coating is not critical since only those molecules reacted with the polycarbonate substrate or reacted in turn with a molecule thus reacted, remain as a part of the coating following the rinse. Thicker coatings are undesirable only to the extent they affect the haze of the lens.
~.
: ~ .
-6a-~$'~
The lenses were then coated with an abrasion-resistant coating obtained from Dow-Corning and identified as C-RESIN. Dow-Corning personnel advised the inventors that the material was covered by U.S. Patent No. 3,986,997. The material was applied to the lenses by dipping in a solution. The C-RESIN
was filtered upon receipt, placed in a con-tainer and -the lenses were immersed and withdrawn a-t a controlled rate. The rate of withdrawal de~ines the coating thickness. The rate of withdrawal may be varied from 1-20 inches per minute. The preferred rates being in the order of 4-1~ inches per minu-te. The lenses of this examples were withdrawn at the rate of 7 1/2 inches per minuie. The lenses were then treated at room temperature.
Following drying, they were cured in an air-circulating oven for eight hours at 250 F. The properties of these lenses, namely, abrasion-resistance, haze and resistance to thermal shock were undetectably equivalent to similarly coated polycarbonate lenses wherein the abrasion-resistant coating (C-RESIN) was applied under conditions of controlled humidity/ i.e. 30~ relative humidity or less.
Example 2 A second group of polycarbonate lenses were treated with the tie-coat solution according to the solution set forth in Example 1. After rinsin~ and drying, the tie-coated lenses were treated by immersion in the Dow-Corning ARC composition and withdrawn at a controlled rate of 7 1/2 inches per minute.
The coated lenses were then permitted to dry at room temperature and subsequently placed in an air-circulating oven for eight bm:
, . : , . , 7~
hours at 250~ F. The lenses were of acceptahle ophthalmic quality and like those of Example 1, ahrasion resistance, haze and resistance to thermal shock were substantially identical with lenses similarly coated in an environment controlled by humidity.
Polycarbonate lenses coated according to the description in U.S. Patent No. ~,986,997 will only provide comparable adhesion if the polycarhonate lenses are thoroughly dried (four hours minimum in an air-circulating oven at 240~ E) and the abrasion-resistant coating is applied in an environment having controlled humidity (30%, or less relative humidity).
Example 3 Ophthalmic CR-39~ lenses are immersed for ahout one minute in a 10% solution of gamma-glycidoxypropyltrimethoxysilane in an aqueous-ethanol mixture having one part water to 17 parts ethyl alcohol adjusted to a pH of 3 to 5 by the addition of acetic acid. After removal, the lenses are rinsed and dried.
` The CR-39~ tie-coated lenses have the abrasion-resistant ARC
coating applied, dried and cured following the procedure o~
; 20 Example 2.
.
~8 bm:
, ~ , , '
Claims (4)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. In combination, an ophthalmic lens selected from the group consisting of polycarbonate and poly diethyleneglycol bis allyl carbonate lenses; a tie-coating having the formula AR,Si(OR2)a(R3)b(OH)c wherein A is selected from the group consisting of NH2, NHR3 and NHR1NH2 when the lens is a polycarbonate and is when the lens is a poly diethylene-glycol bis allyl carbonate, R1 is as alkylene having 2 to 10 carbons, R2 and R3 are alkyl having 1 to 4 carbons, a is 1, 2 or 3, b is 0, 1 or 2, c is 0, 1 or 2 and a+b+c=3; the tie-coating being reacted through A with the lens; and an abrasion-resistant coating from immersion of the lens with the tie-coating in a pigment free aqueous coating composition comprising a dispersion of colloidal silica in lower aliphatic alcohol-water solution of the partial condensate of a silanol of the formula RSi(OH)3 in which R is selected from the group consisting of alkyl radica].s of 1 to 3 inclusive carbon atoms, the vinyl radical, the 3,3,3-trifluoropropyl radical, the gamma-glycidoxypropyl radical and the gamma-methacryloxypropyl radical, at least 70 weight percent of the silanol being CH3Si(OH)3; said composition containing 10 to 50 weight percent sollds consisting essentially of 10 to 70 weight percent colloidal silica and 30 to 90 weight percent of the partial condensate, the abrasion-resistant coating being reacted with the OH of the tie-coating.
2. The combination of Claim 1 wherein the lens is polycarbonate and the tie-coating is gamma-Aminopropyltri-ethyoxysilane.
3. The combination of Claim 2 wherein the abrasion-resistant coating is C-RESIN.
4. The combination of Claim 1 wherein the abrasion-resistant coating is ARC coating.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US762,088 | 1977-01-24 | ||
| US05/762,088 US4127697A (en) | 1975-05-19 | 1977-01-24 | Abrasion-resistant lenses and process of making |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105784A true CA1105784A (en) | 1981-07-28 |
Family
ID=25064082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA293,672A Expired CA1105784A (en) | 1977-01-24 | 1977-12-21 | Abrasion-resistant lenses and process of making |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5393852A (en) |
| AU (1) | AU509942B2 (en) |
| BR (1) | BR7800371A (en) |
| CA (1) | CA1105784A (en) |
| DE (1) | DE2758602A1 (en) |
| FR (1) | FR2378292A1 (en) |
| GB (1) | GB1584231A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4239798A (en) * | 1978-11-01 | 1980-12-16 | General Electric Company | Abrasion resistant silicone coated polycarbonate article |
| US4210699A (en) * | 1978-11-01 | 1980-07-01 | General Electric Company | Abrasion resistant silicone coated polycarbonate article |
| US4386042A (en) * | 1981-02-10 | 1983-05-31 | Akinori Tatebayashi | Molding of synthetic resin article having a hard coating |
| JPS58126502A (en) * | 1982-01-25 | 1983-07-28 | Nippon Sheet Glass Co Ltd | Antireflection plastic optical parts |
| JPS58127514U (en) * | 1982-02-23 | 1983-08-30 | 三菱電機株式会社 | circular fluorescent light fixture |
| DE3345639A1 (en) * | 1983-12-16 | 1985-07-04 | Optische Werke G. Rodenstock, 8000 München | OPTICAL ELEMENT WITH PHOTOTROPIC COVER |
| JP2530436B2 (en) * | 1986-09-18 | 1996-09-04 | 住友化学工業株式会社 | Coating composition |
| JPH01147401A (en) * | 1987-12-02 | 1989-06-09 | Asahi Optical Co Ltd | Protective film for composite optical parts |
| IT201800007937A1 (en) * | 2018-08-07 | 2018-11-07 | Large Colours Srl | Fixing process after surface coloring of polyurethane lenses |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3708225A (en) * | 1971-06-09 | 1973-01-02 | Mbt Corp | Coated synthetic plastic lens |
| US3953115A (en) * | 1973-03-16 | 1976-04-27 | Itek Corporation | Method for providing an abrasion resistant coating for plastic ophthalmic lenses and the resulting lenses |
| US3986997A (en) * | 1974-06-25 | 1976-10-19 | Dow Corning Corporation | Pigment-free coating compositions |
-
1977
- 1977-12-21 CA CA293,672A patent/CA1105784A/en not_active Expired
- 1977-12-27 DE DE19772758602 patent/DE2758602A1/en not_active Ceased
-
1978
- 1978-01-04 GB GB243/78A patent/GB1584231A/en not_active Expired
- 1978-01-13 FR FR7800876A patent/FR2378292A1/en active Granted
- 1978-01-18 AU AU32526/78A patent/AU509942B2/en not_active Expired
- 1978-01-23 BR BR7800371A patent/BR7800371A/en unknown
- 1978-01-23 JP JP533378A patent/JPS5393852A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU3252678A (en) | 1979-07-26 |
| JPS5393852A (en) | 1978-08-17 |
| FR2378292B1 (en) | 1982-06-18 |
| FR2378292A1 (en) | 1978-08-18 |
| JPS6257961B2 (en) | 1987-12-03 |
| AU509942B2 (en) | 1980-05-29 |
| BR7800371A (en) | 1979-01-02 |
| DE2758602A1 (en) | 1978-07-27 |
| GB1584231A (en) | 1981-02-11 |
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