Composition based on allyl monomers and peroxide(s) for the manufacture of organic glasses

Patent metadata

Field	Value
Publication number	US-10851222-B2
Application number	US-201716344619-A
Country	US
Kind code	B2
Filing date	Oct 26, 2017
Priority date	Oct 26, 2016
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

The invention also relates to the use of the composition as defined above for the manufacture of an organic glass, preferably an ophthalmic lens, possibly optionally being tinted by means of pigments and/or organic dyes.

First claim

The invention claimed is:

1. A process for polymerizing one or more allylic monomers and/or allylic copolymers comprising using one or more peroxides of the following formula (I):
1-alkoxy-1- t -alkylperoxycyclohexane  (I)

wherein in formula (I) the alkoxy group comprises from 1 to 4 carbon atoms, the t-alkyl group comprises from 4 to 12 carbon atoms, and the cyclohexane ring is optionally substituted by 1 or 3 alkyl groups, each comprising from 1 to 3 carbon atoms.

2. The process according to claim 1 , wherein the peroxide(s) of formula (I) is/are selected from the group consisting of 1-methoxy-1-tert-amylperoxycyclohexane (TAPMC), 1-methoxy-1-t-butylperoxycyclohexane (TBPMC), 1-methoxy-1-t-amylperoxy-3,3,5-trimethylcyclohexane, 1-methoxy-1-t-butylperoxy-3,3,5-trimethylcyclohexane, 1-ethoxy-1-t-amylperoxycyclohexane (TAPEC), 1-ethoxy-1-t-butylperoxycyclohexane (TBPEC), 1-ethoxy-1-t-amylperoxy-3,3,5-trimethylcyclohexane and/or 1-ethoxy-1-t-butylperoxy-3,3,5-trimethylcyclohexane.

3. The process according to claim 1 , wherein the peroxide of formula (I) is 1-methoxy-1-tert-amylperoxycyclohexane.

4. The process according to claim 1 , wherein the allylic monomer(s) is/are chosen from bis(allyl carbonate) monomers.

5. The process according to claim 1 , wherein the allylic monomer(s) is/are chosen from diol bis(allyl carbonate) monomers of the following formula (II):

wherein in formula (II):
R a and R c , which are identical or different, represent an allyl group of the following formula:

wherein R d is selected from the group consisting of:
a hydrogen atom,
a halogen atom, and
a linear or branched C 1 -C 4 alkyl group, and
R b is selected from the group consisting of alkylene groups, alkylene ether groups, aromatic alkylene ether groups, alkylene polyether groups, alkylene carbonate groups and mixtures thereof.

6. The process according to claim 1 , wherein the allylic monomer(s) is/are selected from the group consisting of ethylene glycol bis(allyl carbonate), diethylene glycol bis(2-methyl carbonate), diethylene glycol bis(allyl carbonate), ethylene glycol bis(2-chloro allyl carbonate), triethylene glycol bis(allyl carbonate), 1,3-propanediol bis(allyl carbonate), propylene glycol bis(2-ethyl allyl carbonate), 1,3-butenediol bis(allyl carbonate), 1,4-butenediol bis(2-bromo allyl carbonate), dipropylene glycol bis(allyl carbonate), trimethylene glycol bis(2-ethyl allyl carbonate), pentamethylene glycol bis(allyl carbonate), isopropylene bis phenol-A bis(allyl carbonate) and mixtures thereof.

7. The process according to claim 1 , wherein the allylic monomer is diethylene glycol bis(allyl carbonate).

8. The process according to claim 1 , wherein the allylic copolymer(s) is/are obtained from the polymerization of diol bis(allyl carbonate) monomers of the following formula (II):

wherein in formula (II):
R a and R c , which are identical or different, represent an allyl group of the following formula:

wherein R d is selected from the group consisting of:
a hydrogen atom,
a halogen atom, and
a linear or branched C 1 -C 4 alkyl group, and
R b is selected from the group consisting of alkylene groups, alkylene ether groups, aromatic alkylene ether groups, alkylene polyether groups, alkylene carbonate groups and mixtures thereof.

9. The process according to claim 1 , wherein the allylic copolymer(s) is/are chosen from polyol poly(allyl carbonates).

10. The process according to claim 1 , wherein the allylic copolymer(s) is/are obtained from the polymerization of a bis(allyl carbonate) monomer and a polyether diol.

11. A polymerizable composition comprising at least one peroxide of formula (I):
1-alkoxy-1- t -alkylperoxycyclohexane  (I),

wherein in formula (I), the alkoxy group comprises from 1 to 4 carbon atoms, the t-alkyl group comprises from 4 to 12 carbon atoms, and the cyclohexane ring is optionally substituted by 1 or 3 alkyl groups, each comprising from 1 to 3 carbon atoms, and at least one allylic monomer, wherein the allylic monomer(s) is/are selected from the group consisting of ethylene glycol bis(allyl carbonate), diethylene glycol bis(2-methyl carbonate), diethylene glycol bis(allyl carbonate), ethylene glycol bis(2-chloro allyl carbonate), triethylene glycol bis(allyl carbonate), 1,3-propanediol bis(allyl carbonate), propylene glycol bis(2-ethyl allyl carbonate), 1,3-butenediol bis(allyl carbonate), 1,4-butenediol bis(2-bromo allyl carbonate), dipropylene glycol bis(allyl carbonate), trimethylene glycol bis(2-ethyl allyl carbonate), pentamethylene glycol bis(allyl carbonate), isopropylene bis phenol-A bis(allyl carbonate) and mixtures thereof, and/or at least one allylic copolymer, wherein the allylic copolymer(s) is/are obtained from the polymerization of diol bis(allyl carbonate) monomers, wherein the diol bis(allyl carbonate) monomers are selected from the group consisting of ethylene glycol bis(allyl carbonate), diethylene glycol bis(2-methyl carbonate), diethylene glycol bis(allyl carbonate), ethylene glycol bis(2-chloro allyl carbonate), triethylene glycol bis(allyl carbonate), 1,3-propanediol bis(allyl carbonate), propylene glycol bis(2-ethyl allyl carbonate), 1,3-butenediol bis(allyl carbonate), 1,4-butenediol bis(2-bromo allyl carbonate), dipropylene glycol bis(allyl carbonate), trimethylene glycol bis(2-ethyl allyl carbonate), pentamethylene glycol bis(allyl carbonate), isopropylene bis phenol-A bis(allyl carbonate) and mixtures.

12. The composition according to claim 11 , further comprising at least one additional peroxide other than the peroxides of formula (I).

13. The composition according to claim 12 , wherein the ratio between the peroxide(s) of formula (I) and the at least one additional peroxide other than the peroxides of formula (I) is between 99:1 and 30:70.

14. The composition according to claim 11 , further comprising at least one photoinitiator.

15. A process for preparing a polymer composition comprising at least one step of polymerization of a polymerizable composition as defined according to claim 11 one or more temperatures ranging from 40 to 140° C.

16. A process for preparing an organic glass comprising at least the following successive steps:
a step of introducing a polymerizable composition as defined according to claim 11 into a device comprising at least one mould,
a step of polymerization of said composition at one or more temperatures ranging from 40 to 140° C., and
a step of recovering the organic glass.

17. The composition according to claim 11 , further comprising at least one additional peroxide other than the peroxides of formula (I), wherein the at least one additional peroxide is chosen from the peroxides of formula (III):
bis- t -alkylperoxycyclohexane  (III),

wherein in formula (III), each t-alkyl group comprises from 4 to 12 carbon atoms and the cyclohexane ring is optionally substituted by 1 or 3 alkyl groups, each comprising from 1 to 3 carbon atoms.

Assignees

• Arkema France

Inventors

• Lafarge Mélanie
• Van Hemelryck Bruno
• Disson Jean-Pierre

Classifications

• G02C7/049

  Contact lenses having special fitting or structural features achieved by special materials or material structures · CPC title

• G02B3/0006

  Arrays (G02B3/02, G02B5/188 take precedence) · CPC title

• G02B1/041

  Lenses · CPC title

• C08L31/00

  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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid (of hydrolysed polymers C08L29/00); Compositions of derivatives of such polymers · CPC title

• C08F18/24 Primary

  Esters of carbonic or haloformic acids · CPC title