Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1998-10-13
2001-10-23
Lipman, Bernard (Department: 1713)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S018000, C549S021000, C549S022000, C549S031000, C549S032000, C549S037000, C526S286000
Reexamination Certificate
active
06307062
ABSTRACT:
The present invention relates, in general, to novel (thio)(meth)acrylate monomers, preferably mono(thio)(meth)acrylate monomers, which are useful for the formulation of polymerizable compositions leading to transparent homopolymers and copolymers that are suitable for optical and ophthalmic uses.
The polymerizable compositions according to the invention allow the manufacture of moulded articles made of transparent polymer, which is preferably thermoplastic, by polymerization in moulds or by injection-moulding.
The transparent polymers obtained, which have refractive indices of medium to high value, 1.54 or more, are particularly suitable for optical and ophthalmic uses.
Among the optical uses of the polymers according to the invention, mention may be made of wave guides and optical fibres.
Among the ophthalmic uses of these polymers, mention may be made of spectacle lenses and contact lenses.
In general, novel monomers according to the present invention are functional monomers of mono(thio)(meth)acrylate or mono- and di(meth)acrylate type bearing a 5- to 8-membered heterocycle consisting of hydrogen, carbon and sulphur atoms and having at least two endocyclic sulphur atoms. Preferably, the heterocycle is 6- or 7-membered, better still 6-membered. Also preferably, the number of endocyclic sulphur atoms is 2 or 3. The heterocycle can optionally be fused with a substituted or unsubstituted C
5
-C
8
aromatic or polycyclanic ring, preferably a C
6
-C
7
ring.
When the heterocycle of the functional monomers according to the invention contains 2 endocyclic sulphur atoms, these endocyclic sulphur atoms are preferably in positions 1-3 or 1-4 of the heterocycle. According to the invention, the monomer is preferably also a thio(meth)acrylate monomer. Lastly, the monomers according to the invention preferably have molar masses of between 150 and 400, preferably 150 and 350 and better still between 200 and 300.
More particularly, the novel functional monomers according to the invention correspond to the formula
in which Z represents H or CH
3
(preferably CH
3
) and X represents O or S, and
when X represents S, Y represents a radical of formula:
where R
1
and R
2
are chosen from H, alkyl radicals, preferably C
1
-C
4
alkyl radicals and better still the CH
3
radical, or alternatively R
1
and R
2
together form a (CH
2
)
5
radical, and n
1
is an integer from 0 to 2 inclusive, and
when X represents O, Y represents the radical (a) defined above or a radical chosen from the radicals of formulae:
in which n
2
is equal to 1 or 2, R
3
represents H or an alkyl radical, preferably a C
1
-C
4
alkyl radical and better still a CH
3
radical, R
4
represents H or an alkyl radical, preferably a C
1
-C
4
alkyl radical and better still a CH
3
or C
2
H
5
radical, and R
5
is a divalent radical chosen from the groups of the following formulae:
in which:
A denotes an aryl group, preferably a C
6
-C
12
aryl group and better still a phenyl group, or an alkyl group, preferably a C
1
-C
6
alkyl group,
R′ and R″ denote, independently of each other, H, an alkyl group, preferably a C
1
-C
6
alkyl group, aryl, preferably phenyl, or R′ or R″ can be a group
where R
a
is an alkylene group, preferably a C
1
-C
6
alkylene group, in particular a —CH
2
— group, and R
b
is H or CH
3
,
n takes the values 0 or 1 and 0≦m (integer≦4), and
R
6
denotes H or CH
3
, and
Cy denotes a substituted or unsubstituted aryl ring, preferably a phenyl, tolyl or norbornyl ring.
Preferably, R
5
is a divalent radical chosen from:
The monomers according to the invention which are particularly recommended are the thio(meth)acrylate monomers corresponding to the formula (A) above in which X represents a sulphur atom and Y is a radical of formula (a).
The monomers according to the invention can be prepared by various known synthetic processes.
Among the mono(thio)(meth)acrylic monomers which are preferred according to the invention, mention may be made of the monomers of formulae:
Among the di(meth)acrylic monomers which are preferred according to the invention, mention may be made of the monomers of formulae:
in particular the dimethacrylate.
REFERENCES:
patent: 5807906 (1998-09-01), Bonvallot et al.
patent: 435306 A2 (1990-12-01), None
patent: 0 435 305 A2 (1990-12-01), None
patent: 0 728 572 A2 (1996-08-01), None
Caye Florence
Jury Dorothée
Mieloszynski Jean-Luc
Paquer Daniel
Schneider Michel
Essilor International (Compagnie Generale d'Optique)
Lipman Bernard
O'Keefe Egan & Peterman, LLP
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