Method for producing an optical material having a high refractive index

• US 5,424,339 A
• Filed: 01/05/1994
• Issued: 06/13/1995
• Est. Priority Date: 03/27/1992
• Status: Expired due to Fees

• Current Assignee: Mitsubishi Chemical Corporation (Mitsubishi Chemical Group Corp.)
• Original Assignee: Mitsubishi Petrochemical Co., Ltd. (Mitsubishi Chemical Group Corp.)
• Inventors: Zanka, Yukihito, Tamura, Yutaka, Isaka, Tsutomu
• Primary Examiner(s): HENDERSON JR, CHRISTOPHER A
• Application Number:
  US08/177,387
• Time in Patent Office: 524 Days
• Field of Search: 522/173, 522/174, 522/170, 522/183, 522/168
• US Class Current: 522/168
• CPC Class Codes: C08F 220/382 and containing oxygen, e.g. 2-sulfoethyl (meth)acrylate
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: G02B 1/041 Lenses

Abstract

An optical material with a high refractive index comprising a resin which is obtainable by polymerization and curing of a composition comprising the following components (A), (B) and (C):

component (A): a sulfur-containing (meth)acrylic monomer represented by the following formula [I], or a mixture of the monomer [I] and a sulfur-containing (meth)acrylic monomer represented by the following formula [II]: ##STR1## in each of which formulas, R¹ represents a hydrogen atom or a methyl group, R² and R³ independently represent a hydrocarbyl group of 1 to 12 carbon atoms, X represents a halogen atom except fluorine, and n represents 0 or an integer of 1 to 4, provided that those groups which are in plurality may be the same or different,

the weight ratio of the compound [I]/the compound [II] being from 10/0 to 1/9;

component (B): a hydroxy(meth)acrylic monomer represented by the following formula [III]: ##STR2## wherein R⁵ represents a hydrogen atom or a methyl group, R⁴ represents a hydrocarbyl group of 1 to 20 carbon atoms which may or may not contain an ether oxygen atom, Y represents a halogen atom except fluorine, and m represents 0 or an integer of 1 or 2, provided that those groups which are in plurality may be the same or different, and p is 1 or 2,

the weight ratio of the component (A)/the component (B) being from 95/5 to 50/50; and

component (C): an isocyanate compound having a plurality of --NCO groups,

the ratio (--NCO/--OH) of the number of --NCO group in the component (C) to the total number of --OH group in the components (A) and (B) being from 0.2 to 3.

The above material for lenses has a low specific gravity and improved refractive index, transparency and impact resistance.

Claims

1. A method for producing an optical material having a high refractive index, which comprises:

irradiating a composition comprising the following components (A), (B) and (C), a radical polymerization initiator and a urethanization catalyst with ultraviolet radiation thereby causing the curing of the composition by a radical polymerization of unsaturated groups in reactants (A) and (B) and by the urethanization reaction of reactants (A) and (B) with isocyanate reactant (C); and

heating the irradiating composition to complete curing;

component (A);

a sulfur-containing (meth)acrylic monomer represented by the following formula [I], or a mixture of the monomer [I] and a sulfur-containing (meth)acrylic monomer represented by the following formula [II];

##STR10## in each of which formulas, R¹ represents a hydrogen atom or a methyl group, R² and R³ independently represent a hydrocarbyl group of 1 to 12 carbon atoms, X represents a halogen atom except fluorine, and n represents 0 or an integer of 1 to 4, provided that those groups which are in plurality may be the same or different,

the weight ratio of the compound [I]/the compound [II] being from 10/0 to 1/9;

component (B);

a hydroxy(meth)acrylic monomer represented by the following formula [III];

##STR11## wherein R⁵ represents a hydrogen atom or a methyl group, R⁴ represents a hydrocarbyl group of 1 to 20 carbon atoms which may or may not contain an ether oxygen atom, Y represents a halogen atom except fluorine, m represents 0 or an integer of 1 or 2, provided that those groups which are in plurality may be the same or different, and p is 1 or 2,

the weight ratio of the component (A)/the component (B) being from 95/5 to 60/40; and

component (C);

an isocyanate compound having a plurality of --NCO groups,

the ratio (--NCO/--OH) of the number of --NCO group in the component (C) to the total number of --OH group in the components (A) and (B) being from 0.2 to 3.

2. The method of producing an optical material with a high refractive index as claimed in claim 1, wherein both the monomers of the formulae [I] and [II] are used.

3. The method of producing an optical material with a high refractive index as claimed in claim 1, wherein R² and R³ of the monomer of formula [I] are each C₁ to C₄.

4. The method of producing an optical material with a high refractive index as claimed in claim 1, wherein the monomer of formula [I] is selected from the group consisting of p-bis(β

-methacryloyloxyethylthio)xylylene, p-bis(β

-acryloyloxyethylthio)xylylene, m-bis(β

-methacryloyloxyethylthio)xylylene, m-bis(β

-acryloyloxyethylthio)xylylene and p-bis(β

-methacryloyloxyethylthio)tetrabromoxylylene.

5. The method of producing an optical material with a high refractive index as claimed in claim 1, wherein R² and R³ of the monomer of formula [II] are each C₁ to C₄.

6. The method of producing an optical material with a high refractive index as claimed in claim 1, wherein the monomer of formula [II] is selected from the group consisting of ##STR12##

7. The method of producing an optical material with a high refractive index as claimed in claim 1, wherein the monomer of formula [III] is selected from the group consisting of (poly)ethylene glycol (meth)acrylates, (poly)propylene glycol (meth)acrylates and glycerol methacrylates.

8. The method of producing an optical material with a high refractive index as claimed in claim 7, wherein the monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxyethoxyethyl methacrylate, 2-hydroxyethoxyethyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 5-hydroxyhexanonyloxyethyl methacrylate (caprolactone modified 2-hydroxyethyl methacrylate), 5-hydroxyhexanonyloxyethyl acrylate (caprolactone modified 2-hydroxyacrylate), glycerol methacrylate, 3-chloro-2-hydroxypropyl methacrylate, 3-chloro-2-hydroxypropyl acrylate, 2-hydroxyethoxyethyl methacrylate and 2-hydroxyethoxyethyl acrylate.

9. The method of producing an optical material with a high refractive index as claimed in claim 8, wherein the monomer is selected from the group consisting of 2-hydroxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethoxyethyl methacrylate and 2-hydroxyethoxyethyl acrylate.

10. The method of producing an optical material with a high refractive index as claimed in claim 1, wherein the isocyanate compound having a plurality of --NCO groups is selected from the group consisting of o-xylylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, isophorone diisocyanate, triisocyanurate, tolylene diisocyanate, 1,2-(diisocyanatomethyl)cyclohexane, 1,3-(diisocyanatomethyl)cyclohexane, 1,4-(diisocyanatomethyl)cyclohexane, diisocyanato(methylcyclohexane), and hexamethylene diisocyanate.

11. The method of producing an optical material with a high refractive index as claimed in claim 10, wherein the isocyanate is m-xylylene diisocyanate.