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CN-116615481-B - Polymerizable composition, resin, molded body, optical material, and lens

CN116615481BCN 116615481 BCN116615481 BCN 116615481BCN-116615481-B

Abstract

A polymerizable composition comprising an episulfide compound represented by the following formula (1), a polyiso (thio) cyanate compound, a polythiol compound, and an epoxy compound (X) which contains 1 or more epoxy groups in one molecule and does not contain an episulfide group. In the formula (1), Y represents a substituted or unsubstituted straight-chain hydrocarbon group having 1 to 4 carbon atoms, a substituted or unsubstituted branched hydrocarbon group having 2 to 4 carbon atoms, a substituted or unsubstituted cyclic hydrocarbon group having 3 to 6 carbon atoms, a substituted or unsubstituted 1, 4-dithiocyclohexenyl group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group, m represents an integer of 0 to 2, and n represents an integer of 0 to 3.

Inventors

  • Toi Marina

Assignees

  • 三井化学株式会社

Dates

Publication Date
20260505
Application Date
20220202
Priority Date
20210205

Claims (14)

  1. 1. A polymerizable composition comprising: an episulfide compound represented by the following formula (1), Polyisocyanate compounds and/or polyisothiocyanate compounds, A polythiol compound having the meaning of, An epoxy compound (X) which contains 1 or more epoxy groups in one molecule and does not contain an episulfide group, A tertiary amine compound, and A lewis acid compound; [ chemical formula 1] In the formula (1), Y represents a substituted or unsubstituted straight-chain hydrocarbon group having 1 to 4 carbon atoms, a substituted or unsubstituted branched hydrocarbon group having 2 to 4 carbon atoms, a substituted or unsubstituted cyclic hydrocarbon group having 3 to 6 carbon atoms, a substituted or unsubstituted 1, 4-dithiocyclohexenyl group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group, m represents an integer of 0 to 2, and n represents an integer of 0 to 3.
  2. 2. The polymerizable composition according to claim 1, wherein the epoxy compound (X) contains an epoxy compound (X1) having 2 or more epoxy groups in one molecule.
  3. 3. The polymerizable composition according to claim 1 or claim 2, wherein the total mole number of mercapto groups contained in the total amount of the polythiol compound is M S , The total mole number of isocyanate groups and/or isothiocyanate groups in the total amount of the polyisocyanate compound and/or polyisothiocyanate compound is set to M N , When the total mole number of the episulfide groups contained in the total amount of the episulfide compound represented by the formula (1) is set to M E , (M S -M N ）/M E is greater than 0 and less than 0.20.
  4. 4. The polymerizable composition of claim 1 or claim 2, wherein the polythiol compound comprises at least one member selected from the group consisting of 5, 7-dimercaptomethyl-1, 11-dimercaptomethyl-3, 6, 9-trithiaundecane, 4, 8-dimercaptomethyl-1, 11-dimercaptomethyl-3, 6, 9-trithiaundecane, 4-mercaptomethyl-1, 8-dimercaptomethyl-3, 6-dithiaoctane, 2, 5-bis (mercaptomethyl) -1, 4-dithiacyclohexane, bis (mercaptoethyl) sulfide, 1, 3-tetrakis (mercaptomethylthio) propane, 4, 6-bis (mercaptomethylthio) -1, 3-dithiacyclohexane, 2- (2, 2-bis (mercaptomethylthio) ethyl) -1, 3-dithiabutane, 1, 2-bis (mercaptomethyl) propane, 1, 2-bis (mercaptomethyl) sulfide, and 4-dithiaethane.
  5. 5. The polymerizable composition according to claim 1 or claim 2, wherein the polyisocyanate compound comprises at least 1 selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, bis (isocyanatocyclohexyl) methane, 2, 5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2, 6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, toluene diisocyanate, 4' -diphenylmethane diisocyanate, and benzene diisocyanate.
  6. 6. The polymerizable composition according to claim 1 or claim 2, further comprising a compound represented by the following formula (2), (R 1 ） 4 Y + X - ...(2) In the formula (2), 4R 1 each independently represents a straight-chain hydrocarbon group having 1 to 10 carbon atoms or a branched-chain hydrocarbon group having 3 to 10 carbon atoms, X represents a halogen atom, and Y represents a nitrogen atom or a phosphorus atom.
  7. 7. The polymerizable composition according to claim 1 or claim 2, wherein the tertiary amine compound comprises at least one of a compound represented by the following formula (3) and a compound represented by the following formula (4), [ Chemical formula 2] In the formula (3), m R 1 each independently represents a linear alkyl group having 1 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or a halogen atom, Q represents a carbon atom, a nitrogen atom, or an oxygen atom, and m represents an integer of 0 to 5; In the formula (4), R 2 、R 3 and R 4 each independently represent a linear alkyl group having 3 to 20 carbon atoms, a branched alkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an allyl group, and R 2 and R 3 may be bonded to each other to form a ring.
  8. 8. The polymerizable composition according to claim 7, wherein the compound represented by the formula (3) is at least 1 selected from the group consisting of 2-methylpyrazine, pyridine, alpha-methylpyridine, beta-methylpyridine, gamma-methylpyridine, 2, 6-dimethylpyridine, 3, 5-dimethylpyridine, 2,4, 6-trimethylpyridine, 3-chloropyridine, 2-ethylpyridine, and 3-ethylpyridine, The compound represented by the formula (4) is at least 1 selected from the group consisting of triallylamine and trioctylamine.
  9. 9. The polymerizable composition according to claim 1 or claim 2, wherein the Lewis acid compound comprises a compound represented by the following formula (5), [ Chemical formula 3] In the formula (5), R 4 represents an alkyl group having 1 to 4 carbon atoms, X represents a fluorine atom, a chlorine atom, a bromine atom, or-O-C (=O) -R 5 ,R 5 represents an alkyl group having 1 to 11 carbon atoms, and C represents an integer of 1 to 3.
  10. 10. The polymerizable composition according to claim 9, wherein the compound represented by the formula (5) is at least 1 selected from the group consisting of dimethyl tin dichloride, dibutyl tin dichloride, and dibutyl tin dilaurate.
  11. 11. A resin which is a cured product of the polymerizable composition according to any one of claim 1 to claim 10.
  12. 12. A molded article comprising the resin according to claim 11.
  13. 13. An optical material comprising the resin of claim 11.
  14. 14. A lens comprising the resin of claim 11.

Description

Polymerizable composition, resin, molded body, optical material, and lens Technical Field The present disclosure relates to a polymerizable composition, a resin, a molded body, an optical material, and a lens. Background Plastic lenses are lightweight and less likely to break and can be dyed as compared with inorganic lenses, and therefore, in recent years, they have been rapidly popularized in applications such as spectacle lenses and camera lenses. In recent years, various studies have been made on a resin composition containing an episulfide compound as a raw material for plastic lenses. For example, patent document 1 discloses a composition for resins comprising a compound having a specific thiirane ring (i.e., a specific episulfide compound), a compound having 1 or more epoxy groups in one molecule, and a polymerization catalyst, in order to develop a method for adjusting the polymerization rate and improving the heat resistance of a resin optical material having a sufficiently high refractive index and a good abbe number. Patent document 1 Japanese patent laid-open publication No. 2005-298742 Disclosure of Invention Problems to be solved by the invention However, a resin obtained from a resin composition containing an episulfide compound (hereinafter, also referred to as "polymerizable composition") is sometimes required to have further improved strength while maintaining a high refractive index. An object of one embodiment of the present disclosure is to provide a polymerizable composition capable of producing a resin having a high refractive index and excellent strength, and a resin having a high refractive index and excellent strength, a molded body, an optical material, and a lens. Means for solving the problems Means for solving the above problems include the following means. <1> A polymerizable composition comprising: an episulfide compound represented by the following formula (1), A polyiso (thio) cyanate compound, A polythiol compound, and An epoxy compound (X) which contains 1 or more epoxy groups in one molecule and does not contain an episulfide group. [ Chemical formula 1] In the formula (1), Y represents a substituted or unsubstituted straight-chain hydrocarbon group having 1 to 4 carbon atoms, a substituted or unsubstituted branched hydrocarbon group having 2 to 4 carbon atoms, a substituted or unsubstituted cyclic hydrocarbon group having 3 to 6 carbon atoms, a substituted or unsubstituted 1, 4-dithiocyclohexenyl group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group, m represents an integer of 0 to 2, and n represents an integer of 0 to 3. <2> The polymerizable composition according to <1>, wherein the epoxy compound (X) contains an epoxy compound (X1) having 2 or more epoxy groups in one molecule. <3> The polymerizable composition according to <1> or <2>, wherein the total mole number of mercapto groups contained in the total amount of the polythiol compound is M S, The total mole number of isocyanate groups in the total amount of the polyisocyanate compounds is M N, When the total mole number of the cyclic sulfur groups contained in the total amount of the cyclic sulfur compounds represented by the above formula (1) is M E, (M S-MN)/ME is greater than 0 and less than 0.20. <4> The polymerizable composition according to any one of <1> to <3>, wherein the polythiol compound comprises at least one member selected from the group consisting of 5, 7-dimercaptomethyl-1, 11-dimercaptomethyl-3, 6, 9-trithiaundecane, 4, 8-dimercaptomethyl-1, 11-dimercaptomethyl-3, 6, 9-trithiaundecane, 4-mercaptomethyl-1, 8-dimercaptomethyl-3, 6-dithiaoctane, 2, 5-bis (mercaptomethyl) -1, 4-dithiocyclohexane, bis (mercaptoethyl) sulfide, 1, 3-tetrakis (mercaptomethylthio) propane, 4, 6-bis (mercaptomethylthio) -1, 3-dithiocyclohexane, 2- (2, 2-bis (mercaptomethylthio) ethyl) -1, 3-dithiobutane, 1, 2-dithio-1, 2-dimethylthio-1, 2-dithio-tetramethylthio-1, 2-dimethylthio-1, 3-dithio-tetramethylthio-methane and (4-mercaptomethyl-1, 3-dithio-methyl-2. <5> The polymerizable composition according to any one of <1> to <4>, wherein the polyisocyanate compound comprises at least one selected from the group consisting of pentamethylene diisocyanate, hexamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, bis (isocyanatocyclohexyl) methane, 2, 5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2, 6-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, toluene diisocyanate, 4' -diphenylmethane diisocyanate, and phenylene diisocyanate. <6> The polymerizable composition according to any one of <1> to <5>, further comprising a compound represented by the following formula (2). (R1)4Y+X-...(2) In the formula (2), 4R 1 each independently represents a straight-chain hydrocarbon group having 1 to 10 carbon atoms or a branched-chain hydrocarbon group having 3 to 10 carbon atoms, X represents a halogen atom, and Y represents a nit