GB1584231A - Method of coating lenses - Google Patents
Method of coating lenses Download PDFInfo
- Publication number
- GB1584231A GB1584231A GB243/78A GB24378A GB1584231A GB 1584231 A GB1584231 A GB 1584231A GB 243/78 A GB243/78 A GB 243/78A GB 24378 A GB24378 A GB 24378A GB 1584231 A GB1584231 A GB 1584231A
- Authority
- GB
- United Kingdom
- Prior art keywords
- coating
- weight
- group
- lens
- gamma
- 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
- 238000000576 coating method Methods 0.000 title claims description 38
- 239000011248 coating agent Substances 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 17
- 229920000642 polymer Polymers 0.000 claims description 15
- -1 poly(diethylene glycol bis allyl carbonate) Polymers 0.000 claims description 13
- 238000005299 abrasion Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229920000515 polycarbonate Polymers 0.000 claims description 10
- 239000004417 polycarbonate Substances 0.000 claims description 10
- 229910000077 silane Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000008119 colloidal silica Substances 0.000 claims description 8
- 239000008199 coating composition Substances 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical group CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000007598 dipping method Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- ZJBHFQKJEBGFNL-UHFFFAOYSA-N methylsilanetriol Chemical compound C[Si](O)(O)O ZJBHFQKJEBGFNL-UHFFFAOYSA-N 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
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)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Ophthalmology & Optometry (AREA)
- Mechanical Engineering (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Eyeglasses (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Paints Or Removers (AREA)
Description
(54) METHOD OF COATING LENSES
(71) We, AMERICAN OPTICAL CORPORATION, a corporation organised under the laws of the State of Delaware, United States of America, of 14
Mechanic Street, Southbridge, Massachusetts 01550, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: The present invention relates to a method of coating lenses, such as ophthalmic lenses.
Various methods of improving the abrasion- and scratch-resistance of transparent polymeric materials are known. In particular, there are disclosed in
U.S. Patent 3,986,997 certain abrasion-resistant coating compositions, particularly for optical elements, which comprise dispersions of colloidal silica in lower aliphatic alcohol-water solutions of the partial condensate of a silanol of the formula RSi(OH)3, in which R is an alkyl group having 1 to 3 carbon atoms, a vinyl group, a 3,3,3-trifluoropropyl group, a gamma-glycidoxy-propyl group or a gamma-methacryloxypropyl group, at least 70% by weight of the silanol being
CH3Si(OH)3. These compositions, which are unpigmented, contain 10 to 50 /n by weight solids consisting essentially of 10 to 70% by weight colloidal silica and 90 to 30% by weight of the partial condensate, and contain an acid in an amount such that their pH is in the range 3.0 to 6.0.
We have now developed a tie coating suitable for use between the abrasionresistant coating compositions of the above-mentioned U.S. Patent and the lens to which such coating is applied, which tie coating requires less control of humidity conditions during coating than some of the tie coatings disclosed in the above U.S.
Patent.
According to the invention, there is provided a method of coating a lens formed of a polymer which is a polycarbonate or poly(diethylene glycol bis allyl carbonate) which comprises:
(a) applying to the lens a tie coating comprising a silane of the formula: AR'Si(OR2)a (R3)b (OH)38b in which A is -NH2, -NHR2 or -NHR1NH2 when the polymer is a polycarbonate or
when the polymer is poly(diethylene glycol bis allyl carbonate), R' is an alkylene group having 2 to 10 carbon atoms, each of R2 and R3 is an alkyl group having 1 to 4 carbon atoms and each of a, b and a plus b is 0, 1 or 2; and
(b) coating the tie coating with a pigment-free abrasion-resistant coating composition comprising a dispersion of colloidal silica in a lower aliphatic alcohol (as defined below)-water solution of a partial condensate of at least one silanol of the formula RSi(OH)3, in which R is an alkyl group having 1 to 3 carbon atoms, a vinyl group, a 3,3,3-trifluoropropyl group, a gamma-glycidoxypropyl group or a gamma-methacryloxypropyl group, at least 70 /,, by weight of the R groups being methyl, the dispersion containing 10 to 50 /" by weight solids consisting of 10 to 70% by weight colloidal silica and 90 to 30 /n by weight of the condensate. The term "lower aliphatic alcohol" is used herein to mean an aliphatic alcohol having 1 to 4 carbon atoms.
When the polymer constituting the lens is a polycarbonate, preferred silanes for use in the tie coating are gamma - aminopropyltriethoxysilane and N - beta aminoethyl - gamma - aminopropyltriethoxysilane, which are commercially available under the trade names A-1100 and Z-6020, respectively, from Dow
Corning Corporation.
When the polymer constituting the lens is poly(diethylene glycol bis allyl carbonate), such as the polymer commercially available under the trade name CR39, the silane in the tie coating is preferably gammaglycidoxypropyltrimethoxysilane. This silane is commercially available from Union
Carbide Corporation and Dow Corning Corporation under the trade names A-187 and Z-6040, respectively.
The tie coating may be applied in any conventional manner, such as by dipping in a dilute solution of the silane, preferably containing less than 20% by weight of the silane. A typical such solution consists of 10% by weight gammaaminopropyltriethoxysilane, 85% by weight ethanol and 5% by weight water. The immersion time in such a solution is, for example, about one minute or more, but the time is not particularly critical. It is believed that such treatment results in a tie coating from 1 to 10 molecules thick. The coating should not be so thick that it impairs transparency of the lens.
The lens is preferably rinsed with water after application of the tie coating in order to avoid haze in the lens, which is very objectionable in ophthalmic lenses.
However, if haze is not objectionable, for example, in sunglass lenses, the rinsing is not necessary.
The inverval between removal of the lens from the tie coating bath and rinsing is not critical and it is even possible to allow the lens to dry before rinsing.
However, if it is desired to rinse the lens, this should be done within about one day in order to avoid an unduly thick tie coating and/or undesirable haze.
The abrasion-resistant coating composition preferably has a pH of 3.0 to 6.0; such a composition is as described in the above-mentioned U.S. Patent and the reader is referred thereto for further details of the composition and its method of application. Typical compositions are available from Dow Corning Corporation under the trade names "ARC" and "C-Resin". These compositions are referred to in the November/December, 1976, issue of "Material News".
The abrasion-resistant coating is preferably applied by dipping in the composition and withdrawing at a rate of 1 to 20 inches per minute, more preferably 4 to 10 inches per minute. The rate of withdrawal is controlled in order to control the coating thickness.
In order that the invention may be more fully understood, the following
Examples are given by way of illustration only:
EXAMPLE 1
Ophthalmic quality injection-moulded polycarbonate lenses were immersed for one minute in a solution consisting of 10% by weight gamma-aminopropyl triethoxysilame, 85 /n by weight ethanol and 5% by weight of water, and, after removal from the solution, rinsed and dried.
The lenses were then dipped in a composition available from Dow Corning
Corporation under the Trade name C-Resin (which composition was filtered before use) and withdrawn at a rate of 7t inches per minute.
After drying at room temperature, the coated lenses were cured for eight hours in an air-circulating oven for eight hours at 2500 F.
The resulting lens had good transparency, abrasion-resistance, haze and resistance to thermal shock.
EXAMPLE 2
Example 1 was repeated, except that the abrasion-resistant coating composition was replaced by a composition commercially available from Dow
Corning Corporation under the trade name "ARC".
Similar results were obtained.
EXAMPLE 3
Ophthalmic quality lenses of a polymer commercially available under the
Trade Mark CR-39 (a poly(diethylene glycol bis allyl carbonate), as mentioned above) were immersed for about one minute in a 10% by weight solution of gamma - glycidoxypropyltrimethoxy silane in a mixture of 17 parts by weight of ethanol and one part by weight of water, the solution having its pH adjusted to 3 to 5 by means of acetic acid.
An abrasion-resistant coating was applied to the resulting tie coated lens in exactly the same manner as in Example 2. Similar results were obtained.
The above examples show that careful control of humidity is not necessary in the method according to the invention. By way of comparison, if the tie coating was not used, it was necessary to dry the lenses thoroughly (for at least four hours in an air-circuiating oven at 2400 F) and to apply the abrasion-resistant coating in an environment having controlled relative humidity of 30% or less in order to obtain comparable results.
WHAT WE CLAIM IS:
1. A method of coating a lens formed of a polymer which is a polycarbonate or poly(diethylene glycol bis allyl carbonate) which comprises:
(a) applying to the lens a tie coating comprising a silane of the formula: AR'Si(OR2)a (R3)b (OH)J-a--b in which A is -NH2, -NHR2 or -NHR1NH2 when the polymer is a polycarbonate or
qhen the polymer is poly(diethylene glycol bis allyl carbonate), R1 is an alkylene group having 2 to 10 carbon atoms, each of R2 and R3 is an alkyl group having 1 to 4 carbon atoms and each of a, b and a plus b is 0, 1 or 2; and
(b) coating the tie coating with a pigment-free abrasion-resistant coating composition comprising a dispersion of colloidal silica in a lower aliphatic alcohol (as defined herein)-water solution of a partial condensate of at least one silanol of the formula RSi(OH)3, in which R is an alky group having 1 to 3 carbon atoms, a vinyl group, a 3,3,3 - trifluoropropyl group, a gamma - glycidoxypropyl group or a gamma - methacryloxypropyl group, at least 70% by weight of the R groups being methyl, the dispersion containing 10 to 50% by weight solids consisting of 10 to 70% by weight colloidal silica and 90 to 30% by weight of the condensate.
2. A method according to claim 1, in which the polymer is polycarbonate and the silane is gamma - aminopropyltriethoxy silane.
3. A method of coating a lens, substantially as herein described in any of
Examples 1 to 3.
4. A coated polymeric lens when produced by the process claimed in any of the preceding claims.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (4)
1. A method of coating a lens formed of a polymer which is a polycarbonate or poly(diethylene glycol bis allyl carbonate) which comprises:
(a) applying to the lens a tie coating comprising a silane of the formula: AR'Si(OR2)a (R3)b (OH)J-a--b in which A is -NH2, -NHR2 or -NHR1NH2 when the polymer is a polycarbonate or
qhen the polymer is poly(diethylene glycol bis allyl carbonate), R1 is an alkylene group having 2 to 10 carbon atoms, each of R2 and R3 is an alkyl group having 1 to 4 carbon atoms and each of a, b and a plus b is 0, 1 or 2; and
(b) coating the tie coating with a pigment-free abrasion-resistant coating composition comprising a dispersion of colloidal silica in a lower aliphatic alcohol (as defined herein)-water solution of a partial condensate of at least one silanol of the formula RSi(OH)3, in which R is an alky group having 1 to 3 carbon atoms, a vinyl group, a 3,3,3 - trifluoropropyl group, a gamma - glycidoxypropyl group or a gamma - methacryloxypropyl group, at least 70% by weight of the R groups being methyl, the dispersion containing 10 to 50% by weight solids consisting of 10 to 70% by weight colloidal silica and 90 to 30% by weight of the condensate.
2. A method according to claim 1, in which the polymer is polycarbonate and the silane is gamma - aminopropyltriethoxy silane.
3. A method of coating a lens, substantially as herein described in any of
Examples 1 to 3.
4. A coated polymeric lens when produced by the process claimed in any of the preceding claims.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/762,088 US4127697A (en) | 1975-05-19 | 1977-01-24 | Abrasion-resistant lenses and process of making |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1584231A true GB1584231A (en) | 1981-02-11 |
Family
ID=25064082
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB243/78A Expired GB1584231A (en) | 1977-01-24 | 1978-01-04 | Method of coating lenses |
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) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT201800007937A1 (en) * | 2018-08-07 | 2018-11-07 | Large Colours Srl | Fixing process after surface coloring of polyurethane lenses |
Families Citing this family (8)
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 |
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
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT201800007937A1 (en) * | 2018-08-07 | 2018-11-07 | Large Colours Srl | Fixing process after surface coloring of polyurethane lenses |
Also Published As
Publication number | Publication date |
---|---|
FR2378292B1 (en) | 1982-06-18 |
FR2378292A1 (en) | 1978-08-18 |
AU509942B2 (en) | 1980-05-29 |
JPS5393852A (en) | 1978-08-17 |
BR7800371A (en) | 1979-01-02 |
AU3252678A (en) | 1979-07-26 |
JPS6257961B2 (en) | 1987-12-03 |
DE2758602A1 (en) | 1978-07-27 |
CA1105784A (en) | 1981-07-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19980103 |