Composition for the manufacture of an ophthalmic lens comprising an UV-absorber and an anti-yellowing additive

Patent metadata

Field	Value
Publication number	US-10370520-B2
Application number	US-201515319260-A
Country	US
Kind code	B2
Filing date	Jun 23, 2015
Priority date	Jun 24, 2014
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

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.

First claim

The invention claimed is:

1. 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 C 1 -C 10 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);
Y 3 —C(Y 1 )—Y 2 is a polar group in which:
Y 1 represents O or S;
Y 2 and Y 3 are similar or different and represent O, S, NH or a bond;

R 99 is any group, which may include at least one function F and/or at least one polar group as defined hereinabove.

2. The polymerizable composition according to claim 1 , wherein Y 1 is O.

3. The polymerizable composition according to claim 1 , wherein the molecular weight of the anti-yellowing additive divided by the number of Y 3 —C(Y 1 )—Y 2 polar groups of the anti-yellowing additive is in the range of about 75 g/mol to about 1000 g/mol.

4. The polymerizable composition according to claim 1 , wherein the anti-yellowing additive is a substituted piperidinyl group having the following formula (VI)

wherein:
R 10 represents a group selected from H, —R a , aryl, —XH, —C(X)—R a , —C(X)—Y—R a and —(R e )—Z, in which:
R a represents a linear or branched C 1 -C 20 alkyl group, or a linear or branched C 2 -C 20 alkenyl group;
aryl represents a monocyclic or bicyclic C 6 -C 14 hydrocarbyl group, which may optionally be substituted with 1 to 4 substituents independently selected from halogen, linear or branched C 1 -C 8 alkyl, linear or branched C 1 -C 8 alkoxy, linear or branched C 1 -C 8 alkylthio, amino, linear or branched C 1 -C 8 monoalkylamino, and linear or branched C 1 -C 8 dialkylamino;
X represents oxygen or sulphur atom;
Y represents oxygen atom, sulphur atom or a group —NR b wherein R b represents hydrogen atom or a linear or branched C 1 -C 20 alkyl group;
R e represents a linear or branched C 1 -C 20 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 —NR b as defined above, and may comprise from 1 to 4 carbon-carbon double bond(s); and
Z represents a hydrogen atom or an aryl group as defined above;

R 20 represents a group selected from linear or branched C 1 -C 8 alkyl, linear or branched C 2 -C 8 alkenyl, linear or branched C 1 -C 8 alkoxy, linear or branched C 1 -C 8 alkylthio, and —(R e )—Z wherein R e and Z are defined as hereinbefore;
n is an integer from 1 to 4 inclusive;
Y 1 represents O or S;
Y 2 and Y 3 are similar or different and represent O, S, NH or a bond; and
R 99 is any group.

5. The polymerizable composition according to claim 4 , wherein R 99 is a group selected from linear or branched C 1 -C 8 alkyl, substituted piperidinyl or a linear or branched C 1 -C 10 alkylene carrying a —COO—C 1 -C 10 alkyl or a —COO-(substituted piperidinyl) group.

6. The polymerizable composition according to claim 5 , wherein the anti-yellowing additive is a substituted 2,2,6,6-tetramethylpiperidine.

7. The polymerizable composition according to claim 5 , wherein the anti-yellowing additive is a compound having the following formula (VII):

wherein:
R1 is hydrogen, linear or branched C 1 -C 15 alkyl, linear or branched C 1 -C 15 acyl or linear or branched C 1 -C 15 alkoxy;
Y 3 represents O or a bond;
B is a group selected from linear or branched C 1 -C 8 alkyl, substituted piperidinyl or a linear or branched C 1 -C 10 alkylene carrying a —COO-alkyl or —COO-(substituted piperidinyl) group.

8. The polymerizable composition according to claim 1 , wherein the anti-yellowing additive corresponds to the following formula (X):

wherein:
each R 2 is independently a linear or branched or cyclic C 1 -C 20 alkyl group wherein 1 to 4 non adjacent carbon atom(s) may be replaced by oxygen atom, sulphur atom, and amino group, and may comprise from 1 to 4 carbon-carbon double bond(s);
each n is an integer from 1 to 17 inclusive; and
m is 1 or 2.

9. The polymerizable composition according to claim 1 , wherein the anti-yellowing additive is a cyclic sulphide having the following formula (XIII)

wherein
R 20 represents a group selected from linear or branched C 1 -C 8 alkyl, linear or branched C 2 -C 8 alkenyl, linear or branched C 1 -C 8 alkoxy, linear or branched C 1 -C 8 alkylthio, and —(R e )—Z wherein Re represents a linear or branched C 1 -C 20 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 —NR b wherein R b represents hydrogen atom or a linear or branched C 1 -C 20 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 C 6 -C 14 hydrocarbyl group, which may optionally be substituted with 1 to 4 substituents independently selected from halogen, linear or branched C 1 -C 8 alkyl, linear or branched C 1 -C 8 alkoxy, linear or branched C 1 -C 8 alkylthio, amino, linear or branched C 1 -C 8 monoalkylamino, and linear or branched C 1 -C 8 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;
Y 1 represents O or S;
Y 2 and Y 3 are similar or different and represent O, S, NH or a bond; and
R 99 is any group.

10. The polymerizable composition according to claim 1 , comprising:
a mixture of an anti-yellowing additive of formula (VII):

wherein:
R1 is hydrogen, linear or branched C 1 -C 15 alkyl, linear or branched C 1 -C 15 acyl or linear or branched C 1 -C 15 alkoxy;
Y 3 represents O or a bond;
B is a group selected from linear or branched C 1 -C 8 alkyl, substituted piperidinyl or a linear or branched C 1 -C 10 alkylene carrying a —COO-alkyl or —COO-(substituted piperidinyl) group; and
an anti-yellowing additive of formula (X):

wherein:
each R2 is independently a linear or branched or cyclic C 1 -C 20 alkyl group wherein 1 to 4 non adjacent carbon atom(s) may be replaced by oxygen atom, sulphur atom, and

Assignees

• Essilor Int

Inventors

• Fromentin Pierre

Classifications

• C08F22/26

  of unsaturated alcohols {(C08F22/1006 takes precedence)} · CPC title

• C08K5/3475

  condensed with carbocyclic rings · CPC title

• C08L35/02 Primary

  Homopolymers or copolymers of esters (C08L35/06, C08L35/08 take precedence) · CPC title

• C08L41/00

  Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur; Compositions of derivatives of such polymers · CPC title

• G02C7/022

  Ophthalmic lenses having special refractive features achieved by special materials or material structures (G02C7/049 takes precedence) · CPC title