Prosthesis (i.e. – artificial body members) – parts thereof – or ai – Eye prosthesis – Intraocular lens
Reexamination Certificate
1999-12-01
2003-03-18
Prebilic, Paul (Department: 3738)
Prosthesis (i.e., artificial body members), parts thereof, or ai
Eye prosthesis
Intraocular lens
C351S159000, C526S281000
Reexamination Certificate
active
06533815
ABSTRACT:
The subject-matter of the present invention is optical lenses, in particular ophthalmic lenses formed from a transparent organic polymer material with a high refractive index and a high Abbe number.
The term “optical lenses with a high refractive index” means optical lenses with a refractive index of greater than or equal to 1.55 and preferably greater than 1.57.
Optical lenses according to the invention are preferably spectacle glasses.
Ophthalmic lenses with a high refractive index must have all the following characteristics:
a high transmission (transmission generally of greater than 85% and preferably of greater than or equal to 90%), with an absence of or optionally a very low light scattering,
a high Abbe number of greater than or equal to 30 and preferably of greater than or equal to 35, in order to avoid chromatic aberrations,
a low yellowing index and an absence of yellowing over time,
good impact strength (in particular according to the CEN and FDA standards),
good suitability for various treatments (shock-proof primer, anti-glare or hard coating deposition, and the like) and in particular good suitability for colouring,
a glass transition temperature value preferably of greater than or equal to 80° C. and better still of greater than 80° C., preferably of between 90 and 110° C.
In addition, the polymerizable compositions for the manufacture of optical lenses must also be easy to process industrially.
In particular, it is desirable for the compositions to be able to be quickly polymerized, in particular photopolymerized, in order to reduce the cycle times in the manufacture of the lenses.
It has been found, according to the invention, that it is possible to obtain an optical lens made of transparent organic polymer material with a high refractive index and a high Abbe number by copolymerization of a mixture of monomers comprising at least one polythiol monomer and at least one monomer with a high Abbe number comprising two to four bridged cyclic end groups comprising an intracyclic ethylenic double bond or a linear or branched aliphatic residue comprising an ethylenic unsaturation, preferably a vinyl or ethylidene group bonded directly to a carbon of the ring.
The bridged cyclic end groups can be noncondensed or condensed cyclic groups.
It is recommended that the bridged cyclic end groups should be chosen from the groups of formulae:
where n is an integer from 0 to 5 inclusive, k is an integer from 0 to 3 inclusive and j is an integer from 0 to 10 inclusive, and
where n is an integer from 0 to 5 inclusive, k′ is an integer from 0 to 2 inclusive and j′ is an integer from 0 to 10 inclusive, Q represents a —C(R′)
2
—, —O—, —S—, —NR′— or —SO
2
— group, with R′ denoting H or a C
1
-C
3
alkyl radical, preferably CH
3
, and R is a hydrogen atom or a C
1
-C
3
alkyl radical, preferably CH
3
.
Mention may be made, among the recommended groups above, of groups of formulae
in which Q represents —C(R′)
2
—, —O—, —S—, —SO
2
— or —NR′—, R′ representing a hydrogen atom or a C
1
-C
3
alkyl radical, preferably CH
3
, R is a hydrogen atom or a C
1
-C
3
alkyl, preferably CH
3
, n=0 to 5 and m=0 to 8.
Preferably, Q represents the —CH
2
— radical.
Preferably again, a monomer with a high Abbe number is chosen, the refractive index of which is at least 1.56.
Polythiol monomers which are suitable for the lenses according to the present invention are well known in the art and can be represented by the formula R
1
(SH)
n
1
in which n
1
is an integer of 2 or more, preferably from 2 to 5, and R
1
is an aliphatic, aromatic or heterocyclic radical.
The polythiol compound is preferably a dithiol, trithiol or tetrathiol compound, in particular a polythiol with a high Abbe number.
These polythiol compounds are well known in the art and are disclosed, inter alia, in Document EP 394,495.
Mention may be made, among dithiols of use in the present invention, of 9,10-anthracenedimethanethiol, 1,11-undecanedithiol, 4-ethylbenzene-1,3-dithiol, 1,2-ethanedithiol, 1,8-octanedithiol, 1,18-octadecanedithiol, 2,5-dichlorobenzene-1,3-dithiol, 1,3-(4-chlorophenyl)propane-2,2-dithiol, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 1,4-cyclohexanedithiol, 1,1-cycloheptanedithiol, 1,1-cyclopentanedithiol, 4,8-dithiaundecane-1,11-dithiol, dithiopentaerythritol, dithiothreitol, 1,3-diphenylpropane-2,2-dithiol, 1,3-dihydroxy-2-propyl 2′,3′-dimercaptopropyl ether, 2,3-dihydroxypropyl 2′,3′-dimercaptopropyl ether, 2,6-dimethyloctane-2,6-dithiol, 2,6-dimethyloctane-3,7-dithiol, 2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 3,3-dimethylbutane-2,2-dithiol, 2,2-dimethylpropane-1,3-dithiol, 1,3-di(4-methoxyphenyl)propane-2,2-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 10,11-dimercaptoundecanoic acid, 6,8-dimercaptooctanoic acid, 2,5-dimercapto-1,3,4-thiadiazole, 2,2′-dimercaptobiphenyl, 4,4′-dimercaptobiphenyl, 4,4′-dimercaptobibenzyl, 3,4-dimercaptobutanol, 3,4-dimercaptobutyl acetate, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, 2,3-dimercaptopropionic acid, 1,2-dimercaptopropyl methyl ether, 2,3-dimercaptopropyl 2′,3′-dimethoxypropyl ether, 3,4-thiophenedithiol, 1,10-decanedithiol, 1,12-dodecanedithiol, 3,5,5-trimethylhexane-1,1-dithiol, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,4-naphthalenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol, 1,9-nonanedithiol, norbornene-2,3-dithiol, bis(2-mercaptoisopropyl)ether, bis(11-mercaptoundecyl)sulphide, bis(2-mercaptoethyl)ether, bis(2-mercaptoethyl)sulphide, bis(18-mercaptoctadecyl)sulphide, bis(8-mercaptooctyl)sulphide, bis(12-mercaptodecyl)sulphide, bis(9-mercaptononyl)sulphide, bis(4-mercaptobutyl)sulphide, bis(3-mercaptopropyl)ether, bis(3-mercaptopropyl)sulphide, bis(6-mercaptohexyl)sulphide, bis(7-mercaptoheptyl)sulphide, bis(5-mercaptopentyl)sulphide, 2,2-bis(mercaptomethyl)acetic acid, 1,1-bis(mercaptomethyl)cyclohexane, bis(mercaptomethyl)durene, phenylmethane-1,1-dithiol, 1,2-butanedithiol, 1,4-butanedithiol, 2,3-butanedithiol, 2,2-butanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2-propanedithiol, 1,2-hexanedithiol, 1,6-hexanedithiol, 2,5-hexanedithiol, 1,7-heptanedithiol, 2,6-heptanedithiol, 1,5-pentanedithiol, 2,4-pentanedithiol, 3,3-pentanedithiol, 7,8-heptadecanedithiol, 1,2-benzenedithiol, 1,3-benzenedithiol, 1,4-benzenedithiol, 2-methylcyclohexane-1,1-dithiol, 2-methylbutane-2,3-dithiol, ethylene glycol dithioglycolate or ethylene glycol bis(3-mercaptopropionate). Mention may be made, among trithiols, of 1,2,3-propanetrithiol, 1,2,4-butanetrithiol, trimethylolpropane trithioglycolate, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol trithioglycolate, pentaerythritol tris(3-mercaptopropionate), 1,3,5-benzenetrithiol and 2,4,6-mesitylenetrithiol.
Mention may also be made, among polythiols of use in the compositions of the present invention, of neopentanetetrathiol, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, pentaerythritol tetrakis(3-mercaptopropionate), 1,3,5-benzenetrithiol, 2,4,6-toluenetrithiol, 2,4,6-methylenetrithiol and polythiols corresponding to the formulae:
(HSCH
2
CH
2
COOCH
2
)
3
CC
2
H
5
(TMPT), and 4-mercaptomethyl-3,6-dithia-1,8-octanedithiol.
Preferred polythiols according to the present invention are ethylene glycol bis(thioglycolate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(thiopropionate) (PETP), 4-mercaptomethyl-3,6-dithia-1,8-octanedithiol (MDO) and bis(2-mercaptoethyl)sulphide (DMDS).
The polythiol component is generally present in the polymerizable compositions in a proportion of 5 to 60% by weight, preferably of 10 to 50% by weight and better still of 20 to 50% by weight with respect to the total weight of monomers present in the composition.
The second essential monomer constituent of the polymerizable compositions for the manufacture of the ophthalmic lenses according to the invention is a copolymerizable monomer with a high Abbe number comprising two to four end groups generally chosen from groups of formulae:
preferably
Essilor International (Compagnie Generale d'Optique)
Fulbright & Jaworski L.L.P.
Prebilic Paul
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