Polymerizable compositions for making optical lens with high...

Details Polymerizable compositions for making optical lens with high... Polymerizable compositions for making optical lens with high...

1999-12-01

2002-11-12

Henderson, Christopher (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C351S159000, C526S260000, C526S268000, C526S282000

Reexamination Certificate

active

06479606

ABSTRACT:

The subject-matter of the present invention is novel polymerizable compositions for the manufacture of optical lenses with a high refractive index and a high Abbe number and the optical lenses, in particular ophthalmic lenses, obtained from these compositions.
The term “optical lens with a high refractive index” means an optical lens with a refractive index of greater than or equal to 1.55 and preferably greater than 1.57.
Novel polymerizable compositions according to the invention are preferably of use in the manufacture of spectacle glasses.
An ophthalmic lens 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 90° C., preferably of between 90 and 110° C.
In addition, the polymerizable compositions must also be easy to process industrially.
In particular, it is desirable for the polymerizable compositions to be able to be quickly polymerized, in particular by photopolymerization.
Patent Document WO 96/38486 discloses polymerizable compositions for the manufacture of optical lenses with a high index and a high Abbe number comprising 20 to 60% by weight of an acrylate or methacrylate monomer derived from a polycyclic olefin, in particular an acrylate or methacrylate derivative of tricyclodecane, 15 to 60% by weight of a di- or polythiol, 5 to 50% by weight of a divinyl or polyvinyl monomer, the vinyl groups of which do not form a (meth)acrylic group, and 0 to 20% by weight of a polymerizable comonomer which can be chosen from methacrylates, acrylates, thiomethacrylates, thioacrylates, vinyls, vinyl ethers, allyls, epoxides and the like.
Although it is indicated that the polymerizable compositions of this document can be polymerized thermally and/or by UV irradiation, all the implementational examples report a thermal curing, the duration of which is particularly lengthy (8 hours).
Patent Document WO 97/44372 discloses a polymerizable composition for the manufacture of ophthalmic lenses which comprises 2.5 to 100% of a divinyl ester cyclic monomer, 5 to 30% by weight of a di- or polythiol monomer and, optionally, 1 to 40% by weight of a thiodiacrylate or -dimethacrylate monomer.
A subject-matter of the present invention is therefore a composition comprising polymerizable monomers for the manufacture of ophthalmic lenses with a high refractive index and a high Abbe number which is easily polymerizable, in particular which is easily photopolymerizable.
The composition comprising polymerizable monomers according to the invention comprises:
(A) at least one polythio(meth)acrylate monomer;
(B) at least one monomer with a high Abbe number comprising at least two polymerizable groups, preferably two to four polymerizable groups, and at least one bridged cyclic constituent unit, the bridged cyclic constituent unit or units not being bonded directly to an oxygen atom;
(C) at least one polythiol monomer; and, optionally,
(D) at least one other monomer which is copolymerizable with the monomers (A), (B) and (C), the composition being devoid of any other monomer comprising one or more vinyl functional groups, other than (meth)acrylic and thio(meth)acrylic functional groups, which is different from the monomers (B).
By definition, a thio(meth)acrylate monomer is a monomer comprising the
group, R
5
having the meaning which appears hereinbelow.
The monomer (A) is preferably a dithio(meth)acrylate.
The monomer (A) is, preferably again, an aliphatic monomer.
A first class of polythio(meth)acrylate monomers suitable for the compositions according to the invention corresponds to the formula:
in which:
R
4
represents a linear or branched, monovalent or polyvalent, aliphatic hydrocarbonaceous radical or a monovalent or polyvalent, aromatic or heterocyclic group bonded directly to the sulphur atom of the thio(meth)acrylate group or groups by a nucleus or via a linear alkyl chain, it being possible for the R
4
radical to comprise, in its chain, one or more groups chosen from —O—, —S— or
R
5
represents hydrogen or —CH
3
; and
n
2
is an integer from 1 to 6, preferably from 1 to 3.
Mention may be made, among monovalent R
4
radicals, of linear or branched C
1
to C
5
alkyl radicals or radicals of formula:
in which:
R
6
and R
7
are, independently of one another, H or a linear or branched C
1
-C
5
alkyl radical;
R
8
is a linear or branched C
1
-C
5
alkyl radical, a C
7
-C
10
aralkyl radical or a C
6
-C
12
aryl radical which is optionally substituted, in particular by alkyl and/or halogen groups; and
n is an integer from 1 to 4.
Mention may be made, among preferred monovalent R
4
radicals, of:
Monomers of formula (I) for which n
2
=1 and which are as defined above are disclosed, inter alia, in U.S. Pat. No. 4,606,864, JP-63316766 and EP-A-0,384,725.
Mention may be made, among divalent R
4
radicals coming within the context of the monomers of formula (I), of linear or branched C
2
to C
10
alkylene radicals which can comprise, in their chain, one or more —O—, —S— or
groups, alkylidene radicals of formula
in which R
9
and R
10
are C
1
-C
5
alkyl radicals, radicals of formula:
in which R
11
and R
12
are linear or branched C
1
-C
5
alkylene groups which can comprise one or more —O—, —S— or
groups in their chains, X″ is chosen from C
1
-C
5
alkyl radicals and halogens, and n
4
is an integer from 0 to 4, and radicals of formula:
in which R
13
and R
14
are linear or branched C
1
to C
5
alkylene radicals which can comprise, in their chain, one or more —O—, —S— or
groups and t and s are equal to 0 or 1.
Mention may be made, among preferred divalent R
4
radicals, of the following radicals:
where q′ is an integer from 1 to 8;
 &Parenopenst;CH
2
CH
2
X&Parenclosest;
u
CH
2
CH
2
—
where X is —O— or —S— and u is an integer from 1 to 4;
&Parenopenst;CH
2
&Parenclosest;
u′
&Brketopenst;S(CH
2
)
v′
&Brketclosest;
z′
&Parenopenst;CH
2
&Parenclosest;
w′
,
where z′ is equal to 0 or 1 and u′, v′ and w′ are integers from 2 to 6;
where u″ and v″ are integers from 1 to 4,
Particularly preferred divalent R
4
radicals are:
Divalent monomers of formula (I) are disclosed, inter alia, in Patents EP-A-273,661, EP-A-273,710 and EP-A-384,725.
Mention may be made, among trivalent R
4
radicals of the monomers of formula (I), of C
3
to C
10
alkyltriyl radicals which can comprise, in their chain, one or more —O—, —S— or
groups, trivalent alkylaryl radicals, the alkyl chains of which comprise one or more —S— or —O— groups, and trivalent aryl groups.
Mention may be made, among trivalent R
4
radicals or R
4
radicals with a higher valency, of:
and the like.
Mention may be made, among monomers of formula (I) recommended in the present invention, of:
S-2-acryloyloxyethyl thio(meth)acrylate,
S-2-methacryloyloxyethyl thio(meth)acrylate,
1,2-bis[(meth)acryloylthio)]ethane,
1,2-bis[(meth) acryloylthio]propane,
1,3-bis[(meth) acryloylthio]propane,
1,4-bis[(meth) acryloylthio]butane,
bis[2-(meth)acryloylthioethyl]ether,
bis[2-(meth)acryloylthioethyl]sulphide,
bis[2-(meth)acryloylthioethoxy]methane,
bis[2-(meth)acryloylthioethylthio]methane,
1,2-bis[2-(meth) acryloylthioethoxy]ethane,
1,2-bis[2-(meth)acryloylthioethylthio]ethane,
bis[2- (2-(meth) acryloylthioethoxy)

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