WO1996034025A1 - Compositions nuançables et reticulables - Google Patents

Compositions nuançables et reticulables Download PDF

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Publication number
WO1996034025A1
WO1996034025A1 PCT/AU1996/000247 AU9600247W WO9634025A1 WO 1996034025 A1 WO1996034025 A1 WO 1996034025A1 AU 9600247 W AU9600247 W AU 9600247W WO 9634025 A1 WO9634025 A1 WO 9634025A1
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WIPO (PCT)
Prior art keywords
casting composition
cross
monomer
optical article
linkable
Prior art date
Application number
PCT/AU1996/000247
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English (en)
Inventor
Chong Meng Kok
Huan Kiak Toh
Colin Maurice Perrott
Original Assignee
Sola International Holdings Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sola International Holdings Ltd. filed Critical Sola International Holdings Ltd.
Priority to EP96911833A priority Critical patent/EP0822948A4/fr
Priority to AU54894/96A priority patent/AU711538B2/en
Publication of WO1996034025A1 publication Critical patent/WO1996034025A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G

Definitions

  • the present invention relates to the manufacture of plastic optical articles such as video discs and ophthalmic lenses.
  • the most widely used plastic ophthalmic lens material is polymerised diethylene glycol bis (allyl carbonate). This polymer has proved a satisfactory material for the manufacture of ophthalmic lenses because of a combination of features, including excellent transmission, resistance to discolouration, high strength and high impact resistance.
  • an important characteristic in the manufacture of, for example, optical lenses is the ability to tint or dye the optical lens material.
  • a particularly important characteristic is the tint rate or the rate at which a dye material is taken up by the optical lens material. This influences both final colour and time of manufacture.
  • the prior art casting compositions have, in general, suffered from relatively low tint rates.
  • the rigidity of a lens material (as determined by the free volume of the lens polymer which controls the diffusion coefficient of the dye in the polymer), and the chemical affinity of the material to dye molecules (as measured by the solubility coefficient) are important parameters controlling the tintability. At low rigidity, dye molecules can penetrate faster into the host material while at high rigidity, penetration becomes more difficult. Affinity refers to chemical compatibility, e.g. a more hydrophilic host material will have a faster uptake of dye molecules dispersed in an aqueous medium. It would accordingly be a significant advance in the art if the tint rate of optical lens materials could be increased and in particular without sacrificing other optical and mechanical properties of the optical lens material. It is accordingly an object of the present invention to overcome or at least alleviate one or more of the difficulties and deficiencies related to the prior art.
  • the present invention provides a cross-linkable polymeric casting composition capable of producing an optical article exhibiting improved tint rate, the casting composition including a polyalkylene glycol diacrylate or dimethacrylate; a urethane monomer having terminal acrylic and/or methacrylic groups; and a monomer including a recurring unit derived from at least one radical- polymerisable bisphenol monomer capable of forming a homopolymer having a high refractive index; and/or a tri- or tetra functional vinyl, acrylic or methacrylic monomer, the cross-linkable polymeric casting composition being modified to reduce the rigidity of the optical article formed therefrom, and/or increase the chemical affinity of the components of the casting composition to a dye material.
  • the cross-linkable polymeric casting composition may be modified such that other optical and mechanical properties of the optical article are reduced to a small extent only. Preferably other mechanical and optical properties may be maintained or even improved.
  • cross-linkable polymeric casting composition according to the present invention may be utilised for the preparation of a tinted optical article.
  • the tinted optical article may be light-transmissible.
  • the tinted optical article may be transparent.
  • a photochromic optical article is preferred.
  • the photochromic optical article may be characterised by having an improved tintability.
  • the optical article may exhibit a high refractive index.
  • the optical article may also retain good abrasion resistance and impact resistance.
  • high refractive index we mean a polymer having a refractive index of at least approximately 1.55, preferably approximately 1.57, more preferably approximately 1.60.
  • the polyoxyalkylene glycol diacrylate or dimethacrylate compound may be present in the polymeric casting composition in an increased amount relative to the casting compositions known in the prior art. As the polyalkylene glycol diacrylate or dimethacrylate is relatively flexible, such increased proportion thereof will provide a reduction in rigidity, and thus an increase in tint rate.
  • the polyoxyalkylene glycol diacrylate or dimethacrylate compound may be present in amounts of from approximately 30% by weight to approximately 90% by weight, more preferably approximately 45% to 90% by weight, most preferably approximately 50% to 70% by weight, based on the total weight of the casting composition.
  • the tint rate can be increased by simply increasing the amount of the more flexible component 9G.
  • a polyethylene glycol dimethacrylate e.g. one designated in the trade as 9G
  • a polyfunctional urethane acrylate e.g. one designated in the trade as U4HA
  • the tint rate can be increased by simply increasing the amount of the more flexible component 9G.
  • an increase in the amount of the more rigid poly functional urethane acrylate will decrease the tint rate, e.g.:
  • Tint rate is inversely proportional to % Transmission after tinting.
  • the polyoxyalkylene glycol diacrylate or dimethacrylate compound includes ethylene oxide or propylene oxide repeating units in its backbone.
  • An ethylene oxide derivative is preferred.
  • the diacrylate or dimethacrylate monomer may include a monomer which exhibits an increased alkylene oxide chain length relative to the prior art. This will also provide a reduction in rigidity and in turn an increase in tint rate. Accordingly, preferably approximately 6 to 23 alkylene oxide repeating units may be included.
  • the alkylene oxide chain length, n is greater than or equal to approximately 9, preferably greater than or equal to approximately 14, more preferably greater than or equal to approximately 23.
  • a polyethylene glycol dimethacrylate may be used.
  • a polyethylene glycol dimethacrylate with an average molecular weight of the order of 600 is preferred.
  • One suitable material is that sold under the trade name NKESTER 9G by Shin Nakamura which has an average molecular weight of 536.
  • the average number of ethylene oxide polymerised units is 9.
  • an NK Ester 14G or 23G having an average number of 14 or 23 ethylene oxide polymerised units respectively may be used.
  • tint rate increases as the number of ethylene oxide groups between the reactive methacrylate end groups increases.
  • analogues 3G, 4G, 6G, 9G, 14G and 23G as the glycol dimethacrylate component, it is possible to vary the tint rate from slow to fast for compositions containing these materials in that order, e.g. n G/ATM20*/U4HA (40/50/10) % Transmission after tinting value of n
  • the polyalkylene glycol diacrylate or dimethacrylate component may be rendered more chemically compatible with a dye material.
  • a diacrylate component may preferably be included as the diacrylates are generally more hydrophilic than the dimethacrylates.
  • the polyoxyalkylene glycol diacrylate or dimethacrylate compound may be otherwise modified to increase hydrophilicity and thus its chemical affinity with a dye material. Accordingly, in a preferred aspect, the polyoxyalkylene glycol diacrylate or dimethacrylate component may include a copolymerisable hydrophilic monomer.
  • the copolymerisable hydrophilic monomer may function to introduce polar groups, for example amine and hydroxy functional groups, into the structure of the starting diacrylate or dimethacrylate component.
  • the copolymerisable hydrophilic molecule may be selected from the group consisting of dimethylamino ethyl acrylate or methacrylate, diethylamino ethyl acrylate or methacrylate or the glycidyl ester of a bisphenol such as bisphenol A.
  • the copolymerisable hydrophilic monomer may be included in the cross- linkable polymeric casting composition in any suitable amounts.
  • the copolymerisable hydrophilic monomer may be present in amounts of from 0 to approximately 20% by weight, based on the total weight of the cross-linkable polymeric casting composition, preferably approximately 2.5 to 15% by weight, more preferably approximately 5 to 10% by weight.
  • a particular cross-linkable polymeric casting composition may require a reduction in the tint rate to balance with other properties.
  • Analogues of polyethylene glycol dimethacrylate which have generally equivalent chain lengths flexibility/free volume, but different chemical affinity to the dye molecules, for example polyethylene dimethacrylates, may be used.
  • the high index bisphenol monomer component in the cross-linkable casting composition may include recurring units capable of forming a homopolymer having a refractive index of approximately 1.55, or greater.
  • the high index bisphenol monomer component may be a polyacrylate or polymethacrylate ester of a bisphenol compound.
  • the high index bisphenol monomer may be selected from compounds having the formula
  • R is methyl, ethyl or hydrogen
  • R 2 is hydrogen, methyl or ethyl
  • R 3 is hydrogen, methyl or hydroxyl
  • R 4 is hydrogen, methyl or ethyl
  • X is hydrogen or a halogen, preferably chlorine, bromine or iodine, or hydrogen
  • m and n are integers having a value of 2 to 20, preferably 4 to 8.
  • the rigidity of the high index bisphenol monomer component may be reduced by increasing the value of m or n. This will in turn increase the tintability of the optical active formed therefrom.
  • X is hydrogen or a halogen, preferably chlorine, bromine or iodine, or hydrogen
  • the chemical affinity for a dye material may be increased by introducing a polar group into the molecule.
  • a halogen is preferred.
  • substitution in the aromatic ring/s with halogens, e.g. using Br, as in the case of NK ester 534M, can be used to change both the diffusivity and the solubility coefficient.
  • Representative monomers of the above-described class include: dimethacrylate and diacrylate esters of bisphenol A; dimethacrylate and diacrylate esters of 4,4'bishydroxyethoxy-bisphenol A and the like.
  • a preferred high index bisphenol compound is bisphenol A ethoxylated dimethacrylate.
  • a bisphenol A ethoxylated dimethacrylate sold under the trade designation ATM20 by Ancomer has been found to be suitable.
  • a glycidyl ester of bisphenol A sold under the trade designation Bis GMA by Freeman Chemicals has been found to be suitable.
  • the high index monomer includes a polar group, e.g. a halogen.
  • Halogenated high index bisphenol compounds which may be used include those sold under the trade designation and NK Ester 534M by Shin Nakamura.
  • High index brominated bisphenol monomers sold under the trade designations SR803, SR804, GX6099 and GX6094 by Dai-lchi-Kogyo Seiyaku (DKS) Co. Ltd. have also been found to be suitable.
  • the high index bisphenol monomer may be present in amounts of from approximately 5 to 40% by weight, preferably 10 to 35% by weight based on the total weight of the casting composition.
  • a secondary high index monomer other than a high index bisphenol monomer may be used in the casting composition according to the present invention in minor amounts.
  • These include styrene, and derivatives thereof; high index acrylate and methacrylate esters including benzyl and phenyl methacrylate; n-vinyl pyrrolidone; and high index aromatic urethanes.
  • the secondary high index monomer component may be included to modify overall refractive index of the optical article formed therefrom.
  • the secondary high index monomer component may be present in amounts of from 0 to approximately 20% by weight based on the total weight of the casting composition.
  • the secondary high index monomer component is present preferably in amounts of approximately 5% to 15% by weight, more preferably approximately 5 to 10% by weight. It is preferred that the secondary high index monomer component is not present in amounts greater than 20% since the optical article formed therefrom may exhibit reduced barcol hardness and/or reduced abrasion resistance. This may be compensated for, to some degree by increasing the amount of high index bisphenol monomer used.
  • the cross-linkable polymeric casting composition includes at least one urethane monomer having terminal acrylic and/or methacrylic groups. The number of such groups may vary from 2 to 6, preferably 2 to 4.
  • the urethane monomer may be modified to decrease the rigidity thereof and/or to decrease the number of cross-linkable sites.
  • An increase in the number of cross-linkable sites will give a tighter and more rigid network with lower free volume and consequently a slower tint rate.
  • a decrease in the number of cross-linkable sites will give a less rigid network with higher free volume and a faster tint rate, e.g. in the composition 9G/ATM20/Urethane acrylate in the ratio 40/50/10 the % transmission after tinting using U4HA (which contains two acrylate and two methacrylate groups per molecule) is 43% while that of U6HA (which contains six acrylate groups per molecule) is 39%. Whilst the U6HA exhibits a larger number of cross-linkable sites, it is structurally a more flexible molecule, thus permitting overall reduction in transmission rate and thus tint rate.
  • Suitable materials falling within this definition include materials supplied under the trade names U-4H, U-4HA and U-6HA by Shin Nakamura, NF-201 and
  • NF-202 by Mitsubishi Rayon. These monomers are included to improve physical toughness without causing the lens material to become too brittle. Impact resistance is improved without adversely affecting abrasion resistance.
  • Certain urethane monomers for example the aromatic urethane methacrylate NF202, are high refractive index components and may function alternatively or in addition as the or one of the secondary high index monomer component(s) of the casting composition.
  • any particular monomer can be selected from those containing aliphatic, aromatic, and cyclic structures of other forms.
  • the tetracrylic urethane monomer gives particularly satisfactory results.
  • the inclusion of the tetracrylic urethane monomer may provide a product of increased hardness.
  • the tetracrylic urethane monomer according to a preferred aspect of the present invention may be a compound of the formula
  • R, R 1 , R 2 and R 3 which may be the same or different are selected from hydrogen, alkyl of 1 to 6 carbon atoms or a substituted alkyl of 1 to 6 carbon atoms; and X is a relatively flexible organic residue having 1 to 20 carbon atoms.
  • X may be an aliphatic, aiicyclic or aromatic residue.
  • X may be selected from the group consisting of C C 20 alkyl, alkoxy, alkylamino, alkyl carbonyl alkoxy carbonyl, alkylamido or alkoxy amide.
  • X may be substituted with one or more polar groups, e.g. halogen, hydroxyl, nitro or amino, alkyl to increase tint rate in the final optical article.
  • the urethane monomer may be present in any suitable amount to provide a desired level of hardness.
  • the urethane monomer may be present in amounts of from approximately 5 to approximately 25% by weight, preferably 5 to 15% by weight based on the total weight of the casting composition.
  • the tri- or tetra-functional vinyl, acrylic or methacrylic monomer may function as a poly functional unsaturated cross-linking agent according to the present invention.
  • the cross-linking agent may be a short chain monomer for example trimethylol propane trimethacrylate, pentaerythritol triacrylate or tetracrylate, or the like.
  • NK Ester TMPT NK Ester A-TMPT
  • NK Ester A-TMM-3 NK Ester A- TMMT
  • di-trimethylol propane tetraacrylate trimethylolpropane triacrylate
  • pentaerythritrol tetramethacrylate dipentaerythritol monohydroxypenta acrylate
  • pentaerythritol triacrylate ethoxylated trimethylolpropane triacrylate
  • ethoxylated trimethylol-propane trimethacrylate ethoxylated trimethylol-propane trimethacrylate.
  • polyfunctional unsaturated cross linking agent material such as that sold under the trade name SR-454 which is an ethoxylated trimethylol propane triacrylate.
  • SR415 has been found to be particularly suitable. SR415 provides increased flexibility in that it includes ten (10) ethoxylated groups in each molecule.
  • the poly functional unsaturated cross-linking agent may be present in amounts of from approximately 5 to 25% by weight, preferably approximately 10% to 20% by weight based on the total weight of the casting composition.
  • the cross-linkable casting composition according to the present invention may further include a cross-linking initiator.
  • the cross-linking initiator may be a heat and/or ultraviolet (UN.) initiator.
  • compositions are preferably cured by a combination of UN. radiation and heat.
  • the combination of UN. radiation and heat may reduce the possibility of incomplete curing for example due to the phenomenon known as "radical trapping".
  • composition with the addition of approximately 0.2 to 2.0% by weight of cross-linking initiator may be exposed to UN. radiation for between 0.5 and 10 seconds.
  • Any commercially viable UN. curing system may be used.
  • a number of fusion bulbs with different output spectra may be considered.
  • One source we have found satisfactory is a 10 inch, 300 watt/inch mercury lamp.
  • the mould assembly is then heated to 100°C for one hour or the lens may be removed from the assembly and heated in air for about one hour at
  • Any suitable UN. initiator may be used.
  • An initiator available under the trade designation Irgacure 184 has been found to be satisfactory. More than one curing agent may be present. It has been possible to operate with a relatively low level of initiator of between approximately 0.05 and 0.25% by weight.
  • a range of photoinitiators available commercially can be used, depending on sample thickness, type of UN. lamp used and the absorption wavelength of the monomer mix. The following photoinitiators have been found to be suitable.
  • Ciba Geigy Irgacure 907 2-methyl-1,[4-(methylthio)phenyl]-2-morpholino- propanone-1
  • Rohm Catalyst 22 • Bis(t-butyl peroxide) diisopropylbenzene t-butyl perbenzoate t-butyl peroxy neodecanoate
  • Amicure BDMA A mixture of two or more of the above may also be used. Additionally, combination of photoiniator mixtures or photoinitiator mixtures with a heat induced free radical initiator such as peroxides, peroxypercabonates or an azo compound may also be employed.
  • a heat curing initiator may be used, for example 1,1-di-tertbutylperoxy-3,3,5-trimethylcyclohexane or secondary isopropyl percarbonate.
  • additives may be present which are conventionally used in casting compositions such as inhibitors, dyes, UN. stabilisers and materials capable of modifying refractive index. Mould release agents can be added but they are in general not required with the compositions used in the method of the present invention.
  • additives may include: UN. Absorbers including • Ciba Geigy Tinuvin P - 2(2'-hydroxy-5'methyl phenyl) benzotriazole
  • HALS Hindered amine light stabilisers
  • Ciba Geigy Irganox 245 triethylene glycol-bis-3-(3-tert butyl-4-hydroxy-5- methyl phenyl)propionate • Irganox 1010 -2,2-bis[[3-[3,4-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1- oxopropoxy]-methyl]-1,3-propanediyl 3,5-bis (1,1 -dimethyl ethyl)-4-hydroxy benzene propanoate
  • monomeric additives can be present in amounts up to 10% by weight as diluents, and include monomers such as methacrylic acid, vinyl silanes, methyl allyl, hydroxy ethyl, methacrylate.
  • monomeric additives may be included to improve processing and/or material properties, these include: • methacrylic acid, maleic anhydride, acrylic acid
  • adhesion promoters/modifiers such as Sartomer 9008, Sartomer 9013, Sartomer 9015 etc.
  • hydrophobic comonomers Shin Nakamura NPG, P9-G etc. to reduce the water adsorption of the material
  • the cross- linkable polymeric casting composition may further include at least one aliphatic glycol dimethacrylate or diacrylate.
  • the aliphatic glycol dimethacrylate or diacrylate may function to reduce the viscosity of the composition and thus improve the processing characteristics of the composition.
  • An ethylene, propylene, butylene or pentylene diacrylate or methacrylate may be used.
  • a butylene glycol dimethacrylate is preferred.
  • One suitable material is that sold under the trade designation NK ester BD by Shin Nakamura.
  • a neopentyl glycol dimethacrylate may be used.
  • One suitable material is that sold under the trade designation NK ester NPG by Shin Nakamura.
  • the aliphatic glycol dimethacrylate or diacrylate may be present in amounts of approximately 1 to 10% by weight, preferably 2.5 to 5% by weight based on the total weight of the casting composition.
  • a tinted optical article including an optical article formed from a cross linkable casting composition including a polyalkylene glycol diacrylate or dimethacrylate; a urethane monomer having terminal acrylic and/or methacrylic groups; and a monomer including a recurring unit derived from at least one radical-polymerisable bisphenol monomer capable of forming a homopolymer having a high refractive index; and/or a tri- or tetra functional vinyl, acrylic or methacrylic monomer, the cross-linkable polymeric casting composition being modified to reduce the rigidity of the optical article formed therefrom, and/or increase the chemical affinity of the components of the casting composition to a dye material; and a dye material incorporated therein.
  • a cross linkable casting composition including a polyalkylene glycol diacrylate or dimethacrylate; a urethane monomer having terminal acrylic and/or methacrylic groups; and a monomer including a recurring unit derived from at least one radical-polymer
  • the dye material utilised in the tinted optical article may be of any suitable type.
  • a photochromic dye is preferred.
  • the photochromic dyes utilised in the process of the present invention are generally activated by near UV light, in the range of wavelengths from approximately 320 nm to 450 nm.
  • the pigment(s) or dye(s) including photochromic dye(s) may be selected from the group consisting of anthraquinones, phthalocyanines, spiro-oxazines, chromenes, pyrans including spiro-pyrans and fulgides.
  • Examples of preferred photochromic dyes may be selected from the group consisting of
  • the optical article may provide characteristics substantially equal to or greater than those achievable with articles made from diethylene glycol bis(allyl carbonate) but with improved dye take-up.
  • the overall refractive index may be in the mid refractive index range of from approximately 1.51 to 1.57, preferably 1.53 to 1.57.
  • optical articles prepared by the method of this invention include camera lenses, ophthalmic lenses and video discs.
  • the casting composition may be formed into an optical article by mixing in a convenient vessel the components making up the material, and then adding the curing catalyst and/or photo-initiator. The mixed material is then degassed or filtered. As the curing time is substantially reduced the casting process may be undertaken on a continuous or semi-continuous basis.
  • the dye material for example a photochromic dye or mixture of dyes, may be incorporated into the optical article so formed in any suitable manner.
  • a surface imbibition technique may be used.
  • the dye material may be incorporated by first positioning a polymeric or other carrier of photochromic dye physically against a surface of the optical article. Heat may then be applied (e.g. in the range 100 to 150°C) to cause the dyes to undergo sorption and diffusion into the lens.
  • the depleted carrier is removed from the lens after the passage of sufficient time at elevated temperature, typically of the order 1/2 to 4 hours. It is found that adequate darkening is achieved with inclusion of 5 to 10 ⁇ g/mm 2 of surface diffused to a depth of about 50 ⁇ m.
  • the average dye concentration in this region of the lens is in the range of approximately 0.1 to 0.2 mg/mm 3 , or approximately 7 to 14% (w/w) of the polymer weight in that region.
  • the optical article may be a coated optical article.
  • the coated optical article may include an optical article formed from a cross-linkable casting composition as described above, and a polymeric coating including a dye, adhered thereto.
  • the polymeric coating may exhibit improved adhesion to the substrate optical article.
  • the optical article may be a lens or lens blank.
  • the polymeric coating may be formed from a polymer of the type described above.
  • the polymeric coating may be of the type described in copending Australian Provisional Patent Application entitled "Process for Preparing Optical Articles" the entire disclosure of which is incorporated herein by reference.
  • the polymer coating may be cast to form a muitifocal, progressive or like region on the surface of a pre-formed lens or lens blank.
  • Such techniques are disclosed for example in United States Patents 5,178,800 and 5,219,497 to Innotech Inc.
  • the polymeric coating may be cast on the optical article utilising front surface coating techniques. Such techniques are described for example in Australian Patent Application 80556/87 or Australian Patent
  • the polymeric coating includes a dye material.
  • a photochromic dye e.g. as described above, is preferred.
  • a chromone photochromic dye is preferred.
  • the dye may be incorporated directly or indirectly into the polymeric coating.
  • the dye may be incorporated by surface imbibition as described above.
  • a cross-linkable casting composition having the following components was prepared
  • TMPT Trimethylol propane trimethacrylate
  • U4HA urethane tetracrylate
  • the monomer mix was prepared in a beaker together with 0.2% V55 as the UN. initiator.
  • the casting material was used to fill the space between a pair of glass moulds separated by a plastic gasket at their periphery and held together by a clip.
  • the mould was then passed 4 times under a UN. lamp. This was followed by a 1 hour extended cure at 100°C.
  • a polymeric carrier bearing a chromone photochromic dye was placed in contact with the optical lens so formed and heated at 130°C for 2 hours.
  • a tinted optical lens was produced.
  • the lens showed relatively poor dye penetration as illustrated below.
  • Example 1 was repeated under similar conditions with monomer mixes as designated in Table 1 below. The results achieved are also given in Table 1. Satisfactory tinted lenses were achieved in Examples 2, 3, 4, 6, 7, 8, 11 and 12.
  • a thin cross section of a dye imbibed lens was allowed to soak in a solution of concentrated nitric acid (pH approximately 0-1) until a deep purple colour was obtained on the front surface. The section was then rinsed under water and the depth of penetration of the photochromic dye was measured by a microscope.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

L'invention porte sur une composition de moulage à polymères réticulables à mème de fabriquer un article optique présentant un taux de nuançage amélioré. La composition de nuançage comprend les éléments suivants: un polyalkylène glycol diacrylate ou diméthacrylate, un monomère d'uréthane à groupes terminaux acryliques et/ou méthacryliques; un monomère comprenant une unité récurrente obtenue à partir d'au moins un monomère de bisphénol à polymérisation radicalaire à même de former un homopolymère ayant un indice de réfraction élevé, et/ou un monomère vinylique, acrylique ou méthacrylique tri ou tétra fonctionnels. La composition de moulage à polymères réticulables est modifiée pour diminuer la rigidité de l'article optique auquel elle donne forme, et/ou pour augmenter l'affinité chimique des constituants de la composition de moulage pour une matière tinctoriale.
PCT/AU1996/000247 1995-04-27 1996-04-26 Compositions nuançables et reticulables WO1996034025A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP96911833A EP0822948A4 (fr) 1995-04-27 1996-04-26 Compositions nuan ables et reticulables
AU54894/96A AU711538B2 (en) 1995-04-27 1996-04-26 Tintable cross-linkable compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPN2684 1995-04-27
AUPN2684A AUPN268495A0 (en) 1995-04-27 1995-04-27 Tintable cross-linkable compositions

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WO1996034025A1 true WO1996034025A1 (fr) 1996-10-31

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AU (1) AUPN268495A0 (fr)
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WO (1) WO1996034025A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8044141B2 (en) * 2003-03-03 2011-10-25 Carl Zeiss Vision Australia Holdings Limited Tinting optical substrates
US20120018686A1 (en) * 2003-10-28 2012-01-26 Schlunt Paul D Compositions for the preparation of composite photochromic polycarbonate lenses

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AU7516091A (en) * 1990-04-20 1991-10-24 Carl Zeiss Vision Australia Holdings Ltd Casting composition
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AU634338B2 (en) * 1990-02-08 1993-02-18 Mitsubishi Rayon Company Limited Composition for plastic lenses

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US4487904A (en) * 1983-09-21 1984-12-11 Toray Industries, Inc. Urethanized acrylic resin material for plastic lens and lens composed thereof
AU8121687A (en) * 1986-11-21 1988-05-26 Sola International Holdings Ltd Cross-linkable casting composition
AU7516091A (en) * 1990-04-20 1991-10-24 Carl Zeiss Vision Australia Holdings Ltd Casting composition
AU5058193A (en) * 1992-11-16 1994-05-26 Sola International Holdings Ltd Cross-linkable polymeric composition

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* Cited by examiner, † Cited by third party
Title
See also references of EP0822948A4 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8044141B2 (en) * 2003-03-03 2011-10-25 Carl Zeiss Vision Australia Holdings Limited Tinting optical substrates
US20120018686A1 (en) * 2003-10-28 2012-01-26 Schlunt Paul D Compositions for the preparation of composite photochromic polycarbonate lenses
US8343391B2 (en) * 2003-10-28 2013-01-01 Signet Armorlite, Inc. Compositions for the preparation of composite photochromic polycarbonate lenses

Also Published As

Publication number Publication date
EP0822948A4 (fr) 1999-06-30
MX9708220A (es) 1998-06-28
AUPN268495A0 (en) 1995-05-25
EP0822948A1 (fr) 1998-02-11
CA2218678A1 (fr) 1996-10-31

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