US20020138921A1 - Method for coloring a transparent article made of polycarbonate and resulting article - Google Patents
Method for coloring a transparent article made of polycarbonate and resulting article Download PDFInfo
- Publication number
- US20020138921A1 US20020138921A1 US09/974,399 US97439901A US2002138921A1 US 20020138921 A1 US20020138921 A1 US 20020138921A1 US 97439901 A US97439901 A US 97439901A US 2002138921 A1 US2002138921 A1 US 2002138921A1
- Authority
- US
- United States
- Prior art keywords
- article
- layer
- thickness
- colouring agent
- polycarbonate
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 49
- 238000004040 coloring Methods 0.000 title claims description 54
- 229920000515 polycarbonate Polymers 0.000 title claims description 51
- 239000004417 polycarbonate Substances 0.000 title claims description 50
- 239000002344 surface layer Substances 0.000 claims abstract description 31
- 230000005855 radiation Effects 0.000 claims abstract description 22
- 230000003287 optical effect Effects 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims description 34
- 238000005299 abrasion Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 239000010410 layer Substances 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 238000000576 coating method Methods 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 14
- 238000001782 photodegradation Methods 0.000 claims description 13
- 229920000728 polyester Polymers 0.000 claims description 12
- 239000004814 polyurethane Substances 0.000 claims description 12
- 229920002635 polyurethane Polymers 0.000 claims description 12
- 239000006096 absorbing agent Substances 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 238000007598 dipping method Methods 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000413 hydrolysate Substances 0.000 claims description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000004816 latex Substances 0.000 claims description 5
- 229920000126 latex Polymers 0.000 claims description 5
- 230000006641 stabilisation Effects 0.000 claims description 5
- 238000011105 stabilization Methods 0.000 claims description 5
- 239000001000 anthraquinone dye Substances 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 4
- 239000004433 Thermoplastic polyurethane Substances 0.000 claims description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 3
- 229920001187 thermosetting polymer Polymers 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Inorganic materials O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 229910052682 stishovite Inorganic materials 0.000 claims description 2
- 229910052905 tridymite Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 229920000178 Acrylic resin Polymers 0.000 claims 1
- 239000004925 Acrylic resin Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 abstract 2
- 230000001678 irradiating effect Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 19
- 239000000049 pigment Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- -1 alkyl radical Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KILURZWTCGSYRE-LNTINUHCSA-K (z)-4-bis[[(z)-4-oxopent-2-en-2-yl]oxy]alumanyloxypent-3-en-2-one Chemical compound CC(=O)\C=C(\C)O[Al](O\C(C)=C/C(C)=O)O\C(C)=C/C(C)=O KILURZWTCGSYRE-LNTINUHCSA-K 0.000 description 3
- 150000001565 benzotriazoles Chemical class 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- 239000008119 colloidal silica Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 108010009736 Protein Hydrolysates Proteins 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000010884 ion-beam technique Methods 0.000 description 2
- 239000000990 laser dye Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000001564 phenyl benzoates Chemical class 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004429 Calibre Substances 0.000 description 1
- 239000004605 External Lubricant Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004610 Internal Lubricant Substances 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- 239000004419 Panlite Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000005102 attenuated total reflection Methods 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 150000008371 chromenes Chemical class 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Images
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
- D06P5/2005—Treatments with alpha, beta, gamma or other rays, e.g. stimulated rays
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C59/00—Surface shaping of articles, e.g. embossing; Apparatus therefor
- B29C59/16—Surface shaping of articles, e.g. embossing; Apparatus therefor by wave energy or particle radiation, e.g. infrared heating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C67/00—Shaping techniques not covered by groups B29C39/00 - B29C65/00, B29C70/00 or B29C73/00
- B29C67/0007—Manufacturing coloured articles not otherwise provided for, e.g. by colour change
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/004—Dyeing with phototropic dyes; Obtaining camouflage effects
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C35/00—Heating, cooling or curing, e.g. crosslinking or vulcanising; Apparatus therefor
- B29C35/02—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould
- B29C35/08—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation
- B29C35/0805—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation
- B29C2035/0827—Heating or curing, e.g. crosslinking or vulcanizing during moulding, e.g. in a mould by wave energy or particle radiation using electromagnetic radiation using UV radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
- B29K2995/0018—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds having particular optical properties, e.g. fluorescent or phosphorescent
- B29K2995/002—Coloured
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2011/00—Optical elements, e.g. lenses, prisms
- B29L2011/0016—Lenses
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/93—Pretreatment before dyeing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/933—Thermosol dyeing, thermofixation or dry heat fixation or development
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
- Y10T428/263—Coating layer not in excess of 5 mils thick or equivalent
- Y10T428/264—Up to 3 mils
- Y10T428/265—1 mil or less
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31935—Ester, halide or nitrile of addition polymer
Definitions
- the present invention concerns in general terms a method for colouring a transparent polycarbonate article, for example an optical or ophthalmic article, and in particular a lens.
- PC polycarbonate
- Ophthalmic lenses made from conventional organic material are generally coloured by dipping in aqueous baths of dispersed dyes, the baths being maintained at a temperature of the order of 95° C.
- polyester links in the copolymer skeleton is essential since it is the polyester bond which is broken by the irradiation and which allows the subsequent penetration of the dye.
- the depths of penetration of the pigments are small, about 10 to 15 nm.
- the document teaches that the copolymer must then contain a higher proportion of polyester.
- the majority of the polycarbonate materials used for ophthalmic optics are homopolycarbonate materials.
- this method particularly intended for colouring PC ophthalmic lenses, and in particular spectacle lenses, must not only be simple but also give the coloration desired by the customer.
- the method must allow variable intensity of coloration : shade A (light), shade B (medium), shade C (dark).
- the method must not significantly alter the essential properties of the lens such as transparency, resistance to shock and to scratches.
- a PC article thus treated may be coloured with ease, in particular by means of dispersions and aqueous solutions of dyes and pigments.
- the method for colouring a transparent article made of polycarbonate not containing polyester groups comprises:
- the method of the invention may obviously also comprise the irradiation of the article to provoke the photodegradation of the polycarbonate material on two opposite faces of the article (each of the faces being subjected to the photodegradation), thus forming two photodegraded surface layers of the polycarbonate material of the article, each having a thickness of at least 1 to 2 ⁇ m.
- the two faces of the article are then placed in contact with the colouring agent so as to diffuse the colouring agent within a thickness of at least 1 to 2 ⁇ m for each of the two photodegraded surface layers.
- the thickness of the photodegraded surface layer or the photodegraded surface layers is preferably from 2 to 20 ⁇ m, and better 2 to 10 ⁇ m.
- the colouring agent may be diffused throughout the entire thickness of the photodegraded surface layer or layers.
- the UV radiation of the step of photodegradation by irradiation preferably has a wavelength such that, during the irradiation, at least 50%, preferably at least 60%, and even more preferably at least 65% of the energy of the irradiation originates from the part of the radiation with wavelength. 320 nm.
- the energy of the irradiation of the article due to the part of the UV radiation with wavelength 320 nm is from 2.4 to 48 J/cm 2 , preferably 10 to 30 J/cm 2
- the energy of the irradiation of the article due to the part of the UV radiation with wavelength>320 nm is from 0.9 J/cm 2 to 15 J/cm 2 , and better from 2 J/cm 2 to 8 J/cm 2 .
- UV radiation has a wavelength range from 200 to 400 nm).
- the time during which each point of one of the faces is subjected to the irradiation is less than 10 minutes, preferably less than 2 minutes and even more preferably less than 30 seconds.
- the optimal duration of the photodegradation step during which the energies listed above are received by the lens vary from 0.1 to 10 seconds, generally and preferably from 0.4 to 4 seconds.
- the UV radiation suitable for the method of the invention may be obtained, for example, by using a UV “H” lamp from the FUSION UV SYSTEM Company at 50% of its nominal power or a UV “D” lamp from the same Company at 40% of its nominal power.
- the UV irradiation of the polycarbonate article must be such that the photo-ageing essentially proceeds according to an “intrinsic” photochemistry, i.e. surface attack.
- an “intrinsic” photochemistry i.e. surface attack.
- Any polycarbonate not containing polyester groups is suitable for the present invention.
- polycarbonate should be understood to include the homopolycarbonates and the copolycarbonates and sequenced copolycarbonates, with the proviso that copolycarbonates containing polyester groups are excluded.
- polycarbonates are commercially available, for example from the Companies GENERAL ELECTRIC COMPANY under the trade name LEXAN®, TEIJIN under the trade name PANLITE®, BAYER under the trade name BAYBLEND®, MOBAY CHEMICAL Corp. under the trade name MAKROLON® and DOW CHEMICAL Co. under the trade name CALIBRE®.
- the preferred polycarbonates are the homopolycarbonates, in particular the homopolycarbonates of bisphenol-A and of tetramethyl-3,5-bisphenol-A (TMBPA).
- the polycarbonate material preferably contains an effective quantity of a UV absorber.
- UV absorbers are adjuvants which are well known in the polymer field and are commercially available.
- UV absorbers include the benzotriazoles, the benzophenones, the dihydroxybenzophenones, the benzimidazoles and the phenyl benzoates.
- the benzotriazoles include the benzotriazoles of formula:
- R 1 represents H or an alkyl radical, preferably C 1 -C 6
- R 2 represents H or an alkyl radical, preferably C 1 -C 8 .
- X represents H or Cl.
- the benzophenones include compounds of formula:
- R 3 is an alkyl radical, preferably C 1 -C 13 .
- the dihydroxybenzophenones include compounds of formula:
- R 4 is an alkyl radical, preferably C 1 -C 8 .
- the phenyl benzoates include compounds of formula:
- R 5 represents H or an alkyl radical, preferably C 1 -C 4 .
- R 6 and R 7 represent H or OH.
- the proportion of UV absorber in the polycarbonate material generally varies from 0 to 10% by weight with respect to the total weight of the material, preferably from 0 to 5%, and more preferably about 2.5% by weight.
- the polycarbonate material may contain any other conventionally used adjuvant which does not impair the optical properties of the material, such as antioxidants, internal or external lubricants, flame retardants and antistatic agents in their usual proportions.
- any dye or pigment conventionally used for colouring transparent polymer articles may be used, including photochromic dyes and pigments.
- a UV absorber may also be diffused at this stage.
- the conventionally used dyes include the azo dyes and the anthraquinone dyes.
- the azo dyes may include monoazo dyes, for example of formula:
- R 8 and R 9 are aryl or heterocyclic radicals, preferably heterocyclic, or diazo dyes, for example of formula:
- R 10 , R 11 and R 12 are aryl or heterocyclic radicals, preferably heterocyclic.
- the anthraquinone dyes may be represented by the formula:
- R 13 and R 14 represent H, OH, an amino group, an alkoxy group, a fluorocarbon group or an acylamino group.
- Other dyes may be infrared absorbers or laser dyes.
- the infrared absorbers include the following compounds:
- R represents H or an alkyl, preferably C 1 -C 4 .
- the laser dyes include dyes containing one or more chromophores selected from one or more porphyrin complexes modified by metals to form metal porphyrin complexes.
- chromophores examples include vanadyl t-butylated phthalocyanine and tin chloride phthalocyanine which absorb at a wavelength of 694 nm and are thus suitable for protection against a ruby laser.
- the photochromic dyes and pigments include the spirooxazines and the chromenes.
- Photochromic dyes and pigments of the chromene type are described, amongst others, in the patents and patent applications WO 90/07507, WO 92/09593, WO 93/17071, FR 2 688 782, EP-401958, EP-562915, U.S. Pat. No. 3,567,605 and U.S. Pat. No. 5,066,818.
- the preferred dyes and pigments are the azo and anthraquinone dyes and pigments.
- the step of colouring the article consists of placing the face corresponding to the photodegraded surface layer of the polycarbonate article in contact with a colouring agent, for example in the form of a solution or dispersion of one or more dyes or pigments, using entirely conventional methods such as dipping in a colouring bath or by centrifugal deposit of a colouring solution on the photodegraded face of the article.
- a colouring agent for example in the form of a solution or dispersion of one or more dyes or pigments
- the contact of the photodegraded face of the article with the colouring agent is preferably carried out by dipping in a colouring bath.
- the colouring baths and solutions are conventionally aqueous solutions and dispersions of a dye or a pigment or mixtures of dyes and pigments.
- These baths and solutions preferably also contain an effective quantity of a surface-active agent, in particular an alkyl benzene sulfonate.
- a surface-active agent in particular an alkyl benzene sulfonate.
- the proportion of surface-active agent in the baths or solutions generally varies from 0 to 3%, preferably 0.2% by weight.
- the temperature of the colouring baths and solutions, during the colouring step is generally between 85 and 100° C., in general about 94 to 95° C.
- the articles are preferably subjected to a thermal treatment to stabilize the coloration, at a temperature preferably higher than 100° C. and possibly reaching 140° C., preferably about 130° C., for a sufficient time to fix the coloration, generally 1 hour or more, preferably about 2 hours.
- the primer coats serve essentially as tack coats to improve the adhesion of the hard anti-abrasion coatings on the article.
- Any primer composition conventionally used for transparent polymer articles, such as ophthalmic lenses, may be used in the method of the invention, in particular conventional shockproof primer layers.
- Preferred primer compositions include compositions based on thermoplastic polyurethanes, such as those disclosed in the Japanese patents 63-141001 and 63-87223, poly(meth)acrylic primer compositions, such as those disclosed in the patent U.S. Pat. No. 5,015,523, compositions based on thermosetting polyurethanes, such as those disclosed in the patent EP-04041 11 and compositions based on poly(meth)acrylic latexes and polyurethane latexes, such as those disclosed in the patents U.S. Pat. No. 5,316,791 and EP-0680492, WO 98/02376.
- thermoplastic polyurethanes such as those disclosed in the Japanese patents 63-141001 and 63-87223
- poly(meth)acrylic primer compositions such as those disclosed in the patent U.S. Pat. No. 5,015,523
- compositions based on thermosetting polyurethanes such as those disclosed in the patent EP-04041 11
- the preferred primer compositions are the compositions based on polyurethanes and compositions based on latexes, particularly the polyurethane latexes.
- the poly(meth)acrylic latexes are latexes of copolymers mainly consisting of a (meth)acrylate, such as for example ethyl, butyl, methoxy or ethoxyethyl (meth)acrylate, with a generally smaller proportion of at least one other comonomer, such as for example styrene.
- a (meth)acrylate such as for example ethyl, butyl, methoxy or ethoxyethyl (meth)acrylate
- at least one other comonomer such as for example styrene.
- the preferred poly(meth)acrylic latexes are acrylate-styrene copolymer latexes.
- Such acrylate-styrene copolymer latexes are commercially available from the Company ZENECA RESINS under the trade name NEOCRYL®.
- Polyurethane latexes are also known and commercially available.
- polyurethane latexes include those containing polyester groups.
- Such latexes which are commercially available include NEOREZ® from the Company ZENECA RESINS and WITCOBOND® from the Company BAXENDEN CHEMICAL.
- Mixtures of these latexes in particular of polyurethane latex and poly(meth)acrylic latex, may also be used as primers.
- primer compositions may be deposited on the faces of the article by dipping or centrifugation, then dried at a temperature of at least 70° C. and up to 100° C., preferably of the order of 90° C., for a time ranging from 2 minutes to 2 hours, generally of the order of 15 minutes, to form primer layers with thicknesses, after baking, of 0.2 to 2.5 ⁇ m, preferably 0.5 to 1.5 ⁇ m.
- the method of the invention also includes the formation of a layer of a hard anti-abrasion coating on the faces of the article, in particular the photodegraded face of the article, preferably coated with a primer coat.
- any composition conventionally used for this purpose, in particular in the ophthalmic optics field, may be used.
- compositions for hard anti-abrasion coating include compositions based on poly(meth)acrylate and compositions based on alkoxysilane hydrolysate, in particular epoxysilane hydrolysate, such as those disclosed in the French patent 93 02649 and the patent U.S. Pat. No. 4,211,823.
- a preferred composition for hard anti-abrasion coating comprises a hydrolysate of epoxysilane and of dialkyldialkoxysilane, a colloidal filler, such as colloidal silica, TiO 2 or Sb 2 O 5 and a catalyst, preferably an aluminium chelate, such as aluminium acetylacetonate, the remainder consisting essentially of solvents conventionally used for the formulation of such compositions.
- the hydrolysate used is preferably a hydrolysate of -glycidyloxypropyl trimethoxysilane (GLYMO) and dimethyl diethoxysilane (DMDES).
- GLYMO -glycidyloxypropyl trimethoxysilane
- DMDES dimethyl diethoxysilane
- composition is obtained by hydrolysis of a mixture of 224 parts by weight of GLYMO and 120 parts of DMDES, to which is added 718 parts by weight of colloidal silica 30% in methanol, 15 parts of aluminium acetylacetonate and 44 parts of ethylcellosolve.
- the primer coat is not necessary to adhere the anti-abrasion coating.
- the thickness of the anti-abrasion coating is generally between 1 and 10 ⁇ m and more particularly between 2 and 6 ⁇ m.
- the method of the invention may also include the formation of an anti-reflection layer on the hard anti-abrasion coating layer.
- the anti-reflection coating may be composed of a mono-or multilayer film, of dielectric materials such as SiO, SiO 2 , Si 3 N 4 , TiO 2 , ZrO 2 , Al 2 O 3 , MgF 2 or Ta 2 O 5 , or their mixtures. It is thus possible to prevent the appearance of a reflection at the lens-air interface.
- This anti-reflection coating is generally applied by vacuum deposit according to one of the following techniques:
- the film In the case where the film consists of a single layer, its optical thickness must be equal to ⁇ /4 where ⁇ is a wavelength between 450 and 650 nm.
- a combination may be used corresponding to the respective optical thicknesses ⁇ /4- ⁇ /2- ⁇ /4 or ⁇ /4- ⁇ /4- ⁇ /4.
- the invention also concerns transparent polycarbonate articles, such as optical glasses or lenses, with two opposite principal faces and comprising at least one photodegraded surface layer on one of the principal faces with a thickness of at least 1 ⁇ m, generally from 2 to 20 ⁇ m, and preferably 2 to 10 ⁇ m, in the entire thickness of which is dispersed a colouring agent.
- the article preferably comprises two photodegraded surface layers on the two opposite principal faces of the article, each having a thickness of at least 1 ⁇ m, generally from 2 to 20 ⁇ m, and preferably 2 to 10 ⁇ m, in which is dispersed the colouring agent.
- the article may be coated on one or two faces with a primer coat, a hard anti-abrasion coating and optionally an anti-reflection coating, as described above with respect to the method of the invention.
- FIG. 1 a schematic frontal view of a device for performing the step of irradiation of a transparent article, such as a lens, made from polycarbonate, according to the method of the invention.
- FIG. 2 a graph of the radiation spectrum of the UV light source of the device of FIG. 1.
- a transparent polycarbonate article such as a lens 1 is transported by means of a conveyor belt 2 under a UV radiation source.
- the UV radiation source for example a UV “D” lamp from the Company FUSION UV SYSTEM operating at 40% of its nominal power, comprises a bulb 3 and a reflector 4 focussing the light beam through a ground quartz screen 5 onto the lens 1 transported by the belt 2.
- the width of the light beam falling on the lens is about 1 cm.
- the photodegradation energy received over 4 seconds by the lens is thus 16 J/cm 2 for the part of the UV radiation with wavelength. 320 nm and 5.73 J/cm 2 for the part of the UV radiation>320 nm.
- the polycarbonate material of the lens 1 is photodegraded, on the upper face of the article, over a depth of at least 1 ⁇ m.
- the belt speed and thus the energy received by the lens may obviously be varied as a function of the lamp used and the desired depth of the photodegraded layer, the conditions being always maintained so that the depth of the photodegraded surface layer of the polycarbonate article is at least 1 ⁇ m and preferably at least 2 ⁇ m.
- the belt speed is generally from 5 cm/minute to 60 cm/minute, preferably from 10 cm/minute to 30 cm/minute, to obtain the desired irradiation energies.
- the irradiation must be such that the temperature reached by the irradiated article remains less than the glass transition temperature (Tg) of the polycarbonate article.
- the lens is subjected to the irradiation treatment on the two principal faces to form two photodegraded surface layers of at least 1 ⁇ m thickness on each of the faces of the article 1.
- the article 1 is coloured, for example by dipping in a colouring bath.
- the colouring bath is generally at a temperature of 85-100° C., and the time spent in the bath may vary from 10 minutes to 1 hour or more, and is in general from 30 minutes to 1 hour.
- the table below shows the compositions of the colouring baths, and the colour obtained.
- Bath 1 Bath 2 Bath 3 Colour green Colour grey Colour brown Water 1 l 1 l 1 l AKBS 2 ml 2 ml 2 ml Blue TERATOP ® GLF 1.25 g 3.95 g 0.95 g Yellow TERATOP ® GNL 9.5 g 8 g 12 g Red TERATOP ® 3G 0.1 g 0.75 g 0.33 g
- the article After removal of the article from the colouring bath, the article is generally subjected to a treatment to wash off the excess of the colouring agent by immersion in an aqueous solution of polyethylene glycol at 55° C., then rinsed with deionised water at 55° C.
- the article is preferably subjected to a thermal treatment to stabilize the colour, in which the article is heated to 130° C. for 2 hours.
- the coloured article was pre-treated with a soda solution at 50° C. for 4 minutes, then immersed for 4 minutes in a primer composition, for example a polyurethane latex (Polyester/polyol from the BAXENDEN Company) at 5° C. After removal, the primer coat was dried at 80° C. for 20 minutes and let cool for 15 minutes.
- a primer composition for example a polyurethane latex (Polyester/polyol from the BAXENDEN Company) at 5° C. After removal, the primer coat was dried at 80° C. for 20 minutes and let cool for 15 minutes.
- the lens was then immersed for 4 minutes in a hard anti-abrasion coating composition at 5° C.
- the hard anti-abrasion coating composition deposited was then baked for 3 hours at 100° C.
- a coloured PC article was thus obtained with a primer coat and a layer of hard anti-abrasion coating on both faces.
- the anti-abrasion coating composition was prepared as follows:
- the theoretical dry extract of the composition contained 13% of solid matter originating from the hydrolysed DMDES.
- the lenses were blown with compressed air to remove burrs and dust.
- the transmission index ⁇ ⁇ (in accordance with standards ISO/CIE 10526: 1991 and ISO/CIE 10527: 1991 and the draft standard ISO/DIS 8980-3 of 1997) was determined.
- the transmission index ⁇ was 17-30%, corresponding to classification 2 as determined in the draft standard ISO/DIS 8980-3.
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- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Manufacturing & Machinery (AREA)
- Mechanical Engineering (AREA)
- Laminated Bodies (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Eyeglasses (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Physical Vapour Deposition (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/844,045 US6911055B2 (en) | 1999-04-08 | 2004-05-12 | Method for coloring a transparent article made of polycarbonate and resulting article |
US11/054,980 US7179848B2 (en) | 1999-04-08 | 2005-02-10 | Method for coloring a transparent article made of polycarbonate and resulting article |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9904409A FR2792010B1 (fr) | 1999-04-08 | 1999-04-08 | Procede de coloration d'un article transparent en polycarbonate et article obtenu |
FR99/04409 | 1999-04-08 | ||
PCT/FR2000/000792 WO2000061857A1 (fr) | 1999-04-08 | 2000-03-30 | Procede de coloration d'un aritcle transparent en polycarbonate et article obtenu |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/FR2000/000792 Continuation WO2000061857A1 (fr) | 1999-04-08 | 2000-03-30 | Procede de coloration d'un aritcle transparent en polycarbonate et article obtenu |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/844,045 Continuation US6911055B2 (en) | 1999-04-08 | 2004-05-12 | Method for coloring a transparent article made of polycarbonate and resulting article |
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US20020138921A1 true US20020138921A1 (en) | 2002-10-03 |
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---|---|---|---|
US09/974,399 Abandoned US20020138921A1 (en) | 1999-04-08 | 2001-10-09 | Method for coloring a transparent article made of polycarbonate and resulting article |
US10/844,045 Expired - Fee Related US6911055B2 (en) | 1999-04-08 | 2004-05-12 | Method for coloring a transparent article made of polycarbonate and resulting article |
US11/054,980 Expired - Fee Related US7179848B2 (en) | 1999-04-08 | 2005-02-10 | Method for coloring a transparent article made of polycarbonate and resulting article |
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US10/844,045 Expired - Fee Related US6911055B2 (en) | 1999-04-08 | 2004-05-12 | Method for coloring a transparent article made of polycarbonate and resulting article |
US11/054,980 Expired - Fee Related US7179848B2 (en) | 1999-04-08 | 2005-02-10 | Method for coloring a transparent article made of polycarbonate and resulting article |
Country Status (10)
Country | Link |
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US (3) | US20020138921A1 (de) |
EP (1) | EP1171664B1 (de) |
JP (1) | JP2003500552A (de) |
AT (1) | ATE275658T1 (de) |
AU (1) | AU761600B2 (de) |
CA (1) | CA2369737C (de) |
DE (1) | DE60013582T2 (de) |
ES (1) | ES2226806T3 (de) |
FR (1) | FR2792010B1 (de) |
WO (1) | WO2000061857A1 (de) |
Cited By (3)
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US20050250870A1 (en) * | 2004-05-04 | 2005-11-10 | Essilor International Compagnie Generale D'optique | Curable adhesive composition and its use in the optical field |
FR2881230A1 (fr) * | 2005-01-25 | 2006-07-28 | Essilor Int | Methode de coloration d'une lentille optique comprenant un primaire d'impression, et lentille optique teintee comprenant un tel primaire d'impression |
WO2016016681A1 (en) * | 2014-07-30 | 2016-02-04 | Essilor International (Compagnie Générale d'Optique) | Method for dyeing a transparent article made of a polymeric substrate with gradient tint |
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FR2904431B1 (fr) * | 2006-07-31 | 2008-09-19 | Essilor Int | Article d'optique a proprietes antistatiques et anti-abrasion, et procede de fabrication |
US20090089942A1 (en) * | 2007-10-09 | 2009-04-09 | Bayer Materialscience Llc | Method of tinting a plastic article |
JP5467670B2 (ja) * | 2008-03-31 | 2014-04-09 | 株式会社ニデック | 染色方法及び染色装置 |
WO2010087327A1 (ja) * | 2009-01-27 | 2010-08-05 | 静岡県 | レーザマーキング方法 |
JP5619472B2 (ja) * | 2010-05-13 | 2014-11-05 | 山本化成株式会社 | 眼鏡レンズ |
JP6010349B2 (ja) * | 2011-06-09 | 2016-10-19 | 株式会社ニデック | 染色方法及び染色装置 |
US8658967B2 (en) | 2011-06-29 | 2014-02-25 | Kla-Tencor Corporation | Optically pumping to sustain plasma |
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-
1999
- 1999-04-08 FR FR9904409A patent/FR2792010B1/fr not_active Expired - Fee Related
-
2000
- 2000-03-30 ES ES00917114T patent/ES2226806T3/es not_active Expired - Lifetime
- 2000-03-30 EP EP00917114A patent/EP1171664B1/de not_active Expired - Lifetime
- 2000-03-30 JP JP2000610899A patent/JP2003500552A/ja active Pending
- 2000-03-30 CA CA2369737A patent/CA2369737C/fr not_active Expired - Fee Related
- 2000-03-30 AU AU38233/00A patent/AU761600B2/en not_active Ceased
- 2000-03-30 AT AT00917114T patent/ATE275658T1/de not_active IP Right Cessation
- 2000-03-30 DE DE60013582T patent/DE60013582T2/de not_active Expired - Fee Related
- 2000-03-30 WO PCT/FR2000/000792 patent/WO2000061857A1/fr active IP Right Grant
-
2001
- 2001-10-09 US US09/974,399 patent/US20020138921A1/en not_active Abandoned
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2004
- 2004-05-12 US US10/844,045 patent/US6911055B2/en not_active Expired - Fee Related
-
2005
- 2005-02-10 US US11/054,980 patent/US7179848B2/en not_active Expired - Fee Related
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US20050250870A1 (en) * | 2004-05-04 | 2005-11-10 | Essilor International Compagnie Generale D'optique | Curable adhesive composition and its use in the optical field |
US7439278B2 (en) | 2004-05-04 | 2008-10-21 | Essilor International Compagnie Generale D'optique | Curable adhesive composition and its use in the optical field |
FR2881230A1 (fr) * | 2005-01-25 | 2006-07-28 | Essilor Int | Methode de coloration d'une lentille optique comprenant un primaire d'impression, et lentille optique teintee comprenant un tel primaire d'impression |
WO2006079715A1 (fr) * | 2005-01-25 | 2006-08-03 | Essilor International (Compagnie Generale D'optique) | Methode de coloration d'une lentille optique comprenant un primaire d'impression, et lentille optique teintee comprenant un tel primaire d'impression |
US20080127432A1 (en) * | 2005-01-25 | 2008-06-05 | Essilor International (Compagnie Generale D'optiqu | Method For Coloring an Optical Lens Comprising a Printing Primer, and Optical Colored Lens Comprising Such a Printing Primer |
US8740996B2 (en) | 2005-01-25 | 2014-06-03 | Essilor International (Compagnie Generale D'optique) | Method for coloring an optical lens comprising a printing primer, and optical colored lens comprising such a printing primer |
WO2016016681A1 (en) * | 2014-07-30 | 2016-02-04 | Essilor International (Compagnie Générale d'Optique) | Method for dyeing a transparent article made of a polymeric substrate with gradient tint |
CN106536172A (zh) * | 2014-07-30 | 2017-03-22 | 埃西勒国际通用光学公司 | 用于以梯度色调对由聚合物基材制成的透明物品进行染色的方法 |
US10201944B2 (en) * | 2014-07-30 | 2019-02-12 | Essilor International | Method for dyeing a transparent article made of a polymeric substrate with gradient tint |
Also Published As
Publication number | Publication date |
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US20050170186A1 (en) | 2005-08-04 |
JP2003500552A (ja) | 2003-01-07 |
DE60013582D1 (de) | 2004-10-14 |
AU3823300A (en) | 2000-11-14 |
FR2792010B1 (fr) | 2001-07-27 |
US6911055B2 (en) | 2005-06-28 |
EP1171664B1 (de) | 2004-09-08 |
AU761600B2 (en) | 2003-06-05 |
EP1171664A1 (de) | 2002-01-16 |
WO2000061857A1 (fr) | 2000-10-19 |
ES2226806T3 (es) | 2005-04-01 |
DE60013582T2 (de) | 2005-03-31 |
CA2369737C (fr) | 2010-08-10 |
WO2000061857A8 (fr) | 2002-08-08 |
ATE275658T1 (de) | 2004-09-15 |
US7179848B2 (en) | 2007-02-20 |
CA2369737A1 (fr) | 2000-10-19 |
FR2792010A1 (fr) | 2000-10-13 |
US20040265572A1 (en) | 2004-12-30 |
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