Polymerizable composition for optical material, molded product, optical material, and plastic lens and method for manufacturing same

Patent metadata

Field	Value
Publication number	US-12448470-B2
Application number	US-201816769027-A
Country	US
Kind code	B2
Filing date	Dec 5, 2018
Priority date	Dec 6, 2017
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

A polymerizable composition for an optical material includes: an allyl carbonate compound (A) including two or more allyloxycarbonyl groups at a terminal which is represented by General Formula (1); and a radical polymerization initiator (B). The radical polymerization initiator (B) includes at least one kind of radical polymerization initiator (B1) which is a peroxyester-based radical polymerization initiator, and a radical polymerization initiator (B2).

First claim

The invention claimed is:

1. A polymerizable composition for an optical material, comprising:
an allyl carbonate compound (A) including two or more terminal allyloxycarbonyl groups which is represented by General Formula (1); and
a radical polymerization initiator (B) including a combination of a radical polymerization initiator (B1) and a radical polymerization initiator (B2),
wherein the radical polymerization initiator (B1) is a peroxyester-based radical polymerization initiator,
the radical polymerization initiator (B2) is at least one kind selected from the group consisting of a peroxyester-based radical polymerization initiator and a peroxyketal-based radical polymerization initiator, and
the radical polymerization initiator (B1) is contained 0.2 parts by weight or more and 0.7 part by weight or less, and the radical polymerization initiator (B2) is contained 0.8 parts by weight or more and 3.0 parts by weight or less, with respect to 100 parts by weight of the allyl carbonate compound (A),

wherein, in General Formula (1), R 1 represents a divalent to 20 valent group derived from a chained or branched aliphatic polyol with 3 to 35 carbon atoms which optionally include a hetero atom, or a divalent to 20 valent group derived from a cycloaliphatic polyol with 5 to 40 carbon atoms which optionally include a hetero atom, n represents an integer of 2 to 20, and R 1 does not include an allyloxycarbonyl group,
wherein the peroxyester-based radical polymerization initiator used as the radical polymerization initiator (B1) includes t-hexylperoxypivalate, t-hexylperoxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, t-amylperoxyneodecanoate, or t-amylperoxypivalate,
the peroxyester-based radical polymerization initiator used as the radical polymerization initiator (B2) includes t-butylperoxyisononanoate, t-amylperoxy normal octanoate, or t-amylperoxyisononanoate,
the peroxyketal-based radical polymerization initiator used as the radical polymerization initiator (B2) includes n-butyl-4,4-di(t-butylperoxy) valerate, 2,2-bis(4,4-di-t-butylperoxycyclohexyl) propane, or 2,2-di(t-butylperoxy) butane.

2. The polymerizable composition for an optical material according to claim 1 ,
wherein the allyl carbonate compound (A) includes at least one kind selected from the group consisting of a bis(allyl carbonate) compound of at least one kind of diol selected from the group consisting of diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,4-dimethylolcyclohexane, and 4,8-bis(hydroxymethyl)-[5.2.1.0 2,6 ]tricyclodecane; a tris(allyl carbonate) compound of at least one kind of triol selected from the group consisting of glycerol, trimethylolpropane, and tris(hydroxyethyl) isocyanurate; a tetra(allyl carbonate) compound of at least one kind of tetraol selected from the group consisting of pentaerythritol, diglycerol, and ditrimethylolpropane; a hexa(allyl carbonate) compound of dipentaerythritol; and a hexa(allyl carbonate) compound of bispentaerythritol,
the polymerizable composition for an optical material comprising the allyl carbonate compound (A) or a mixture of the allyl carbonate compound (A) and an oligomer thereof.

3. The polymerizable composition for an optical material according to claim 1 ,
wherein the allyl carbonate compound (A) is at least one kind selected from the group consisting of
(i) a diethylene glycol bis(allyl carbonate) compound,
(ii) a bis(allyl carbonate) compound of a mixture of diethylene glycol and neopentyl glycol,
(iii) a poly(allyl carbonate) compound of a mixture of diethylene glycol and tris(hydroxyethyl) isocyanurate,
(iv) a poly(allyl carbonate) compound of a mixture of diethylene glycol and trimethylolpropane,
(v) a poly(allyl carbonate) compound of a mixture of diethylene glycol and pentaerythritol,
(vi) a poly(allyl carbonate) compound of a mixture of diethylene glycol, neopentyl glycol and pentaerythritol, and
(vii) a poly(allyl carbonate) mixture of a poly(allyl carbonate) compound of a mixture of diethylene glycol, neopentyl glycol, and pentaerythritol,
the polymerizable composition for an optical material including a mixture of the allyl carbonate compound (A) and an oligomer thereof.

4. The polymerizable composition for an optical material according to claim 1 , further comprising:
a polyol compound (E) represented by General Formula (a);

wherein, in General Formula (a), R 2 represents a hydroxyl group, an —OX group, or a linear or branched alkyl group having 1 to 4 carbon atoms, R 3 represents a hydrogen atom, an X group, or a linear or branched alkyl group having 1 to 4 carbon atoms, R 4 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, Q 1 to Q 7 each independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a —CH 2 —OX group, or a —OX group, p represents an integer of 1 to 4, s represents an integer of 0 to 4, t represents an integer of 0 to 4, r represents an integer of 1 or more and 1000 or less, a plurality of Q 1 to Q 7 , X, s, and t may be the same or different, and * represents a bond.

5. A molded product obtained by curing the polymerizable composition for an optical material according to claim 1 .

6. An optical material comprising:
the molded product according to claim 5 .

7. A plastic lens comprising:
the molded product according to claim 5 .

8. A plastic polarizing lens, comprising:
a polarizing film; and
a base layer comprised of the molded product according to claim 5 and formed over at least one surface of the polarizing film.

9. A method for manufacturing a plastic lens, comprising: a step of forming a lens base material by cast polymerization of the polymerizable composition according to claim 1 .

Assignees

• Mitsui Chemicals Inc

Inventors

• Ogawa Tatsuya
• Furuya Masayuki

Classifications

• G02B1/041

  Lenses · CPC title

• C09D133/06

  of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title

• C08K5/053

  Polyhydroxylic alcohols · CPC title

• C08F299/022

  from polycondensates with side or terminal unsaturations · 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