Composition for the manufacture of an ophthalmic lens comprising an UV-absorber and an anti-yellowing additive
AssigneeEssilor International
InventorPierre Fromentin
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Abstract
The present invention relates to a thermosetting composition for the manufacture of an ophthalmic lens which efficiently absorbs ultraviolet (UV) rays without exhibiting undesirable yellowing, said composition comprising an allyl monomer or oligomer, a catalyst, a UV-absorber and a specific anti-yellowing additive. The present invention also relates to the use of said composition and to the ophthalmic lens obtained from said composition.
Claims20
A polymerizable composition for the manufacture of an ophthalmic lens, comprising:
- at least 20% by weight based on the total weight of the composition of at least one allyl monomer or oligomer selected from diethylene glycol bis(allyl carbonate), ethylene glycol bis(allyl carbonate), oligomers of diethylene glycol bis(allyl carbonate), oligomers of ethylene glycol bis(allyl carbonate), and mixtures thereof;
- at least one catalyst suitable for initiating the polymerization of said allyl monomer or oligomer;
- at least one UV absorber;
- at least one anti-yellowing additive, wherein said anti-yellowing additive corresponds to general formula (I):
- wherein:
- F represents a function selected from sulfide, disulfide or a substituted piperidinyl group;
- A is a bond or represents a linear or branched C1-C10 alkylene group, wherein 1 to 4 non adjacent carbon atom(s) may independently be replaced by an oxygen atom, a sulphur atom or an amino group, and may comprise from 1 to 4 carbon-carbon double bond(s);
- Y3—C(Y1)—Y2 is a polar group in which:
- Y1 represents O or S;
- Y2 and Y3 are similar or different and represent O, S, NH or a bond;
- R99 is any group, which may include at least one function F and/or at least one polar group as defined hereinabove.
An ophthalmic lens obtained by filling in a mould then polymerizing:
- at least 20% by weight based on the total weight of the composition of at least one allyl compound selected from diethylene glycol bis(allyl carbonate), ethylene glycol bis(allyl carbonate), oligomers of diethylene glycol bis(allyl carbonate), oligomers of ethylene glycol bis(allyl carbonate), and mixtures thereof;
- at least one catalyst suitable for initiating the polymerization of said allyl compound;
- at least one UV absorber;
- and
- at least one anti-yellowing additive;
- wherein said ophthalmic lens has a Yellow Index lower than or equal to 2.0, as measured immediately after manufacture and wherein the variation in the Yellow Index after exposing said lens to UV light for 80 h does not exceed 0.5 in absolute value.
A polymerizable composition for the manufacture of an ophthalmic lens, comprising:
- at least one allyl monomer or oligomer;
- at least one catalyst suitable for initiating the polymerization of said allyl monomer or oligomer;
- at least one UV absorber;
- and
- at least one anti-yellowing additive selected from:
- a dialkyl thiodipropionate corresponding to formula (XXIa) or a dialkyl 3,3′-dithiodipropionate corresponding to formula (XXIb):
- wherein each R22 is methyl, ethyl, ethyl-hexyl or octyl;
- or
- a dialkyl thiodiglycolate corresponding to formula (XXIIa) or a dialkyl dithiodiacetate corresponding to formula (XXIIb):
- wherein each R22 is independently methyl, ethyl, ethyl-hexyl or octyl;
- or
- a cyclic sulphide having the following formula (XIII):
- wherein
- R20 represents a group selected from linear or branched C1-C8 alkyl, linear or branched C2-C8 alkenyl, linear or branched C1-C8 alkoxy, linear or branched C1-C8 alkylthio, and —(Re)—Z wherein Re represents a linear or branched C1-C20 alkylene group, wherein 1 to 4 non adjacent carbon atom(s) may independently be replaced by an oxygen atom, a sulphur atom or an amino group —NRb wherein Rb represents hydrogen atom or a linear or branched C1-C20 alkyl group, and may comprise from 1 to 4 carbon-carbon double bond(s);
- and
- Z represents a hydrogen atom or an aryl group, wherein aryl represents a monocyclic or bicyclic C6-C14 hydrocarbyl group, which may optionally be substituted with 1 to 4 substituents independently selected from halogen, linear or branched C1-C8 alkyl, linear or branched C1-C8 alkoxy, linear or branched C1-C8 alkylthio, amino, linear or branched C1-C8 monoalkylamino, and linear or branched C1-C8 dialkylamino;
- n is an integer from 1 to 5 inclusive;
- B represents a 3 to 12-membered monocyclic heterocycloalkyl which comprises, in addition to the sulphur atom of the cycle, from 1 to 3 heteroatoms independently selected from oxygen and sulphur;
- Y1 represents O or S;
- Y2 and Y3 are similar or different and represent O, S, NH or a bond;
- and
- R99 is any group.
Dependencies are inferred from the claim text.