Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From sulfur-containing reactant
Reexamination Certificate
2001-06-06
2003-02-11
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From sulfur-containing reactant
C528S373000, C525S535000, C525S212000
Reexamination Certificate
active
06518393
ABSTRACT:
This invention relates to the field of polymerizable monomer compositions which, after polymerization, provide transparent polymeric substrates, and their use for manufacturing optical lenses, more particularly ophthalmic lenses.
Polymerizable compositions have already been disclosed for the manufacture of ophthalmic lenses having a high refractive index.
Compositions comprising a polyoxyalkyleneglycol di(meth)acrylate monomer, a monomer containing a bisphenol-A pattern and leading, through homopolymerization, to a polymer having a higher refractive index than 1.55 and a urethane monomer having 2 to 6 (meth)acrylic end groups are disclosed in EP-A-453,149.
Polymerization is preferably a mixed UV/thermal one.
The patent application EP-745,621 discloses a photopolymerizable composition comprising:
a) 10% to 70% of a bis-2-[(meth)acryloylthioethyl] sulfide or a mixture thereof with the bis [(meth)acryloylthiophenyl]sulfide,
b) 10% to 60% by weight of at least one poly(ethoxy)bisphenol-A di(meth)acrylate type monomer,
c) 5% to 30% by weight of at least one aromatic or polycyclanic mono(meth)acrylate monomer,
d) 0 to 15% by weight of a polyalkyleneglycol di(meth)acrylate, and
e) 0 to 10% by weight of a polythiol.
Patent specification 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, more particularly a tricyclodecane acrylate or methacrylate derivative, 15% to 60% by weight of a di- or polythiol, 5% to 50% by weight of a divinyl or polyvinyl monomer, and 0 to 20% by weight of a polymerizable comonomer that can be selected amongst methacrylates, acrylates, thiomethacrylates, thioacrylates, vinyls, vinylethers, allyls, epoxides and the like.
The optical items produced from such compositions have high refractive indices up to 1.6 or more and Abbe numbers of 38 or higher.
Although it is mentioned that the polymerizable compositions disclosed in this document can be polymerized thermally and/or by UV radiation, all the embodiments mention a thermal curing step, the time period of which is particularly long (8 hours).
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, is described in patent specification WO 97/44372.
As it is thus appreciated, numerous polymerizable compositions have been offered in the prior art, leading to materials with a refractive index of 1.6 or higher, without being totally satisfactory in a view to obtaining transparent polymeric substrates, for use in the optical field.
Thus, a first object of this invention aims at providing new polymerizable monomer compositions leading to transparent polymeric substrates.
In particular, the optical substrates must show the following set of features:
a high transparency (transmission being generally higher than 85%, and preferably, higher than or equal to 90%), without or with a very little light diffusion,
a low density lower than 1.4, preferably lower than 1.3, and more preferably lower than 1.2,
a refractive index in the range of 1.55 to 1.60,
a high Abbe number, in the range of 35 to 45, in order to avoid chromatic aberrations,
a lack of colour after polymerization, in particular a low yellow index and a lack of yellowness in the course of time,
a good impact resistance (in particular, the uncoated glass should preferably successfully satisfy the ball fall FDA test),
a good resistance to the action of static stresses,
a good abrasion resistance,
a good ability to several treatments (hard coating deposit, anti-reflection, adhesion and/or anti-shock primers,...), and in particular a good colouration capacity,
a good ability to surfacing and projecting treatments, without the glass global geometry being altered during these operations, and
a low water absorption rate.
A second object of this invention aims at providing compositions that could be easily and rapidly polymerized, in particular they could be polymerized with photopolymerization techniques or mixed photopolymerization and thermal polymerization techniques allowing to reduce the cycle periods for the lens manufacture.
The polymerizable monomer composition according to the invention comprises:
(a) at least 40 parts by weight, preferably at least 50 and more preferably 55 parts by weight of at least one thio(meth)acrylate monomer,
(b) at least one high Abbe number monomer,
(c) at the most 20 parts by weight of an aromatic polyvinyl monomer, and
(d) at least one polythiol, for 100 parts by weight of (a), (b), (c) and (d).
The aromatic polyvinyl monomer typically represents 0.5 to 10 parts by weight, preferably 1 to 5 parts by weight based on 100 parts by weight of (a), (b), (c) and (d).
Preferably, the high Abbe number monomer(s) represent(s) 10 to 40 parts by weight, more preferably 10 to 30, and the polythiol 5 to 20 parts by weight for 100 parts by weight of the mixture of monomers (a), (b), (c) and (d).
Preferably, the polythiol represents at the most 20 parts by weight and more preferably, at the most 15 parts for 100 parts by weight of (a), (b), (c) and (d).
Moreover, the polymerizable compositions may include for 100 parts of the mixture of monomers (a), (b), (c) and (d), up to 30 parts by 35 weight of at least another copolymerizable monomer, different from the monomers of (a), (b), (c) and (d). Preferably, the other polymerizable comonomer represents no more than 20 parts by weight and more preferably, no more than 10 parts by weight for 100 parts of the mixture of monomers of (a), (b), (c) and (d). Preferably, such other copolymerizable monomer is a radical copolymerizable monomer.
One of the advantages of the invention lies in that such compositions may be easily and rapidly photopolymerized.
The monomer or the mixture of monomers for the component (a) of the composition according to the invention encompasses any monomer comprising at least one thioacrylate or thiomethacrylate function.
In the present description and claims, it is understood by a thio(meth)acrylate function a functional group of the formula:
wherein R
1
is H or —CH
3
.
Preferably, the monomers of the component (a) have the following formula:
wherein:
R is a linear or branched, monovalent or polyvalent aliphatic hydrocarbon radical, or a monovalent or polyvalent aromatic group, directly linked to the sulfur atom of the thio(meth)acrylate group(s) with an aromatic ring or by means of a linear alkyl chain, said R radical being able to include in its chain one or more groups selected amongst
R
1
is hydrogen or —CH
3
, and
n is an integer from 1 to 6, preferably from 1 to 3.
The monovalent R radicals may include a linear or branched C
1
-C
5
alkyl group, the radicals of the formula:
wherein:
R
2
and R
3
are, independently from one another, H or a linear or branched C
1
-C
5
alkyl radical,
R
4
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, optionally substituted, in particular with alkyl and/or halogen groups, and
m is an integer from 1 to 4.
The preferred monovalent R radicals may include: C
2
H
5
SCH
2
CH
2
—
Monomers of formula (I) in which n=1 and such as defined hereabove, are disclosed, amongst others, in U.S. Pat. No. 4,606,864, JP-63,316,766 and EP-A-0,384,725.
The divalent R radicals which fall within the scope of the monomers of formula (I) may include the linear or branched C
2
-C
10
alkylene radicals that can include in their chain one or more
groups, the alkylidene radicals of the formula:
wherein R
5
and R
6
are C
1
-C
5
alkyl radicals, the radicals of the formula:
wherein R
7
and R
8
are linear or branched C
1
-C
5
alkylene groups, that can include one or more
groups in their chains and X is selected from the C
1
-C
5
alkyl radicals and halogens, and p is an integer from 0 to 4,
Pillie Maxime
Primel Odile
Richard Gilles
Yean Leanirith
Essilor International (Compagnie Generale d'Optique)
Fulbright & Jaworski L.L.P.
Truong Duc
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