Ophthalmic mouldings

Details Ophthalmic mouldings Ophthalmic mouldings

1999-08-12

2001-04-24

Berman, Susan W. (Department: 1711)

Plastic and nonmetallic article shaping or treating: processes

Direct application of electrical or wave energy to work

Polymerizing, cross-linking, or curing

C351S159000, C351S16000R, C522S084000, C522S096000, C522S097000, C522S173000, C526S312000, C528S059000

Reexamination Certificate

active

06221303

ABSTRACT:

The present invention relates to novel polyoxyalkylene-unit-containing block copolymers having a number of crosslinkable side groups, to a process for the preparation thereof, and to the use thereof in the production of mouldings, especially opthalmic mouldings, such as contact lenses.
A tetraacrylate that is obtained by reacting a polypropylene glycol diglycidyl diacrylate with a diisocyanate and a hydroxyethyl acrylate, and the use thereof as a formulation component in resin mixtures for stereolithographic processes, is already known from EP-A-0 614 122.
It has now surprisingly been found that specific crosslinkable polyether copolymers are especially suitable for the production of ophthalmic mouldings, such as, for example, contact lenses.
The present invention relates to ophthalmic mouldings obtainable by crosslinking a prepolymer that corresponds essentially to formula
wherein
R and R
3
are each independently of the other hydrogen or methyl, one of the radicals Y
1
and Y
2
is hydrogen and the other is hydrogen or methyl,
R
1
is the radical of a linear or branched aliphatic diisocyanate having from 3 to 24 carbon atoms, the radical of a cycloaliphatic or aliphatic-cycloaliphatic diisocyanate having from 3 to 24 carbon atoms, or the radical of an aromatic or araliphatic diisocyanate having from 6 to 24 carbon atoms,
R
2
is C
1
-C
12
alkylene or a radical of formula
—[CHY
3
—CHY
4
—O]
m
—CHY
3
—CHY
4
—  (2),
 wherein one of the radicals Y
3
and Y
4
is hydrogen and the other is hydrogen or methyl,
m is an integer from 4 to 99 and
n is an integer from 5 to 100,
in the absence or presence of an additional vinyl comonomer.
In formula (1) R is, for example, methyl or, preferably, hydrogen. The variable R
3
is, for example, hydrogen or, preferably, methyl.
A variant of the prepolymers used in accordance with the invention concerns those in which one of Y
1
and Y
2
is hydrogen and the other is methyl. A further preferred variant of the prepolymers used in accordance with the invention concerns those in which Y
1
and Y
2
are each hydrogen. The variable n is, for example, an integer from 5 to 100, especially from 8 to 50 and more especially from 9 to 25.
R
1
is preferably linear or branched C
3
-C
18
alkylene or unsubstituted or C
1
-C
4
alkyl- or C
1
-C
4
-alkoxy-substituted C
6
-C
10
arylene, C-C
18
aralkylene, C
6
-C
10
arylene-C
1
-C
2
alkylene-C
6
-C
10
-arylene, C
3
-C
8
cycloalkylene, C
3
-C
8
cycloalkylene-C
1
-C
6
alkylene, C
3
-C
8
cycloalkylene-C
1
-C
2
-alkylene-C
3
-C
8
cycloalkylene or C
1
-C
6
alkylene-C
3
-C
8
cycloalkylene-C
1
-C
6
alkylene.
R
1
as alkylene is preferably a linear or branched C
3
-C
18
alkylene radical, especially a linear or branched C
4
-C
12
alkylene radical and more especially a linear, or especially a branched, C
6
-C
12
alkylene radical. Preferred alkylene radicals include 1,4-butylene, 2,2-dimethyl-1,4-butylene, 1,5-pentylene, 2,2-dimethyl-1,5-pentylene, 1,6-hexylene, 2,2,3- or 2,2,4-trimethyl-1,5-pentylene, 2,2-dimethyl-1,6-hexylene, 2,2,3- or 2,2,4- or 2,2,5-trimethyl-1,6-hexylene, 2,2-dimethyl-1,7-heptylene, 2,2,3- or 2,2,4- or 2,2,5- or 2,2,6-trimethyl-1,7-heptylene, 2,2-dimethyl-1,8-octylene, and 2,2,3- or 2,2,4- or 2,2,5- or 2,2,6- or 2,2,7-trimethyl-1,8-octylene.
When R
1
is arylene it is especially naphthylene or more especially phenylene. When the arylene is substituted, a substituent is preferably located in the ortho position to an isocyanate group. Examples of substituted arylene are 1 -methyl-2,4-phenylene, 1,5-dimethyl-2,4-phenylene, 1-methoxy-2,4-phenylene and 1 -methyl-2,7-naphthylene. R
1
as aralkylene is especially naphthylalkylene or more especially phenylalkylene. The alkylene group in the aralkylene contains preferably from 1 to 12, especially from 1 to 6, or more especially-from 1 to 4 carbon atoms. More especially, the alkylene group in the aralkylene is methylene or ethylene. Examples include 1,3- or 1,4-benzylene, naphth-2-yl-7-methylene, 6-methyl-1,3- or 1,4-benzylene, and 6-methoxy-1,3- or -1,4-benzylene.
When R
1
is cycloalkylene it is especially C
5
-C
6
cycloalkylene or more especially cyclohexylene, each of which is unsubstituted or substituted by methyl. Examples include 1,3-cyclobutylene, 1,3-cyclopentylene, 1,3- or 1,4-cyclohexylene, 1,3- or 1,4-cycloheptylene, 1,3- or 1,4- or 1,5-cyclooctylene, 4-methyl-1,3-cyclopentylene, 4-methyl-1,3-cyclohexylene, 4,4-dimethyl-1,3-cyclohexylene, 3-methyl- or 3,3-dimethyl-1,4-cyclohexylene, 3,5-dimethyl-1,3-cyclohexylene and 2,4-dimethyl-1,4-cyclohexylene.
When R
1
is cycloalkylenealkylene it is preferably cyclopentylene-C
1
-C
4
alkylene or especially cyclohexylene-C
1
-C
4
alkylene, each of which is unsubstituted or mono- or poly-substituted by C
1
-C
4
alkyl, especially methyl. The group cycloalkylenealkylene is more especially cyclohexyleneethylene or preferably cyclohexylenemethylene, each of which is unsubstituted or substituted in the cyclohexylene radical by from 1 to 3 methyl groups. Examples include cyclopent-1-yl-3-methylene, 3-methylcyclopent-1-yl-3-methylene, 3,4-dimethylcyclopent-1-yl-3-methylene, 3,4,4-trimethylcyclopent-1-yl-3-methylene, cyclohex-1-yl-3- or -4-methylene, 3- or 4- or 5-methylcyclohex-1-yl-3- or -4-methylene, 3,4- or 3,5-dimethylcyclohex-1-yl-3- or 4-methylene, and 3,4,5- or 3,4,4- or 3,5,5-trimethylcyclohex-1-yl-3- or -4-methylene.
When R
1
is alkylenecycloalkylenealkylene it is preferably C
1
-C
4
alkylenecyclopentylene-C
1
-C
4
alkylene or especially C
1
-C
4
alkylenecyclohexylene-C
1
-C
4
alkylene, each of which is unsubstituted or mono- or poly-substituted by C
1
-C
4
alkyl, especially methyl. The alkylenecycloalkylenealkylene group is more especially ethylenecyclohexyleneethylene or preferably methylenecyclohexylenemethylene, each of which is unsubstituted or substituted in the cyclohexylene radical by from 1 to 3 methyl groups. Examples include cyclopentane-1,3-dimethylene, 3-methylcyclopentane-1,3-dimethylene, 3,4-dimethylcyclopentane-1,3-dimethylene, 3,4,4-trimethylcyclopentane-1,3-dimethylene, cyclohexane-1,3- or -1,4-dimethylene, 3- or 4- or 5-methylcyclohexane-1,3- or -1,4-dimethylene, 3,4- or 3,5-dimethylcyclohexane-1,3- or -1,4-dimethylene, and 3,4,5- or 3,4,4- or 3,5,5-trimethylcyclohexane-1,3- or -1,4-dimethylene.
R
1
as C
3
-C
8
cycloalkylene-C
1
-C
2
alkylene-C
3
-C
8
cycloalkylene or C
6
-C
10
arylene-C
1
-C
2
alkylene-C
6
-C
10
arylene is preferably C
5
-C
6
cycloalkylenemethylene-C
5
-C
6
cycloalkylene or phenylene-methylenephenylene, each of which may be unsubstituted or substituted in the cycloalkyl or phenyl ring by one or more methyl groups.
The radical R
1
is of symmetrical or, preferably, asymmetrical structure.
In a preferred group of R
1
radicals, R
1
is linear or branched C
6
-C
10
alkylene, cyclohexylenemethylene or cyclohexylenemethylenecyclohexylene unsubstituted or substituted in the cyclohexyl moiety by from 1 to 3 methyl groups, or phenylene or phenylenemethylenephenylene unsubstituted or substituted in the phenyl moiety by methyl.
Examples of suitable radicals R
1
are the radicals of methylene bis(phenylisocyanate), hexamethylene diisocyanate (HMDI), methylene bis(cyclohexylisocyanate), isophorone diisocyanate (IPDI), toluylene-2,4-diisocyanate (TDI) and of 1,6-diisocyanato-2,2,4-trimethyl-n-hexane (TMDI).
In an especially preferred group of R
1
radicals, R
1
is linear or branched C
6
-C
10
alkylene, or cyclohexylenemethylene or cyclohexylenemethylenecyclohexylene unsubstituted or substituted in the cyclohexyl moiety by from 1 to 3 methyl groups. R
1
is more especially asymmetrical, branched C
6
-C
10
alkylene, or cyclohexylenemethylene substituted in the cyclohexyl moiety by from 1 to 3 methyl groups.
When R
2
is an alkylene radical it is, for example, straight-chain or branched C
1
-C
12
alkylene. R
2
as an alkylene radical is especially C
1
-C
6
alkylene or more especially C
2
-C
4
alkylene. Examples of especially preferred alkylene radicals R
2
are 1,3-propylene and, especially, 1,2-ethylene.
When R
2
is a radical of the above formula (2), which

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