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EP-4741436-A1 - POLYMERIZABLE COMPOSITION FOR OPTICAL MATERIAL, POLYMERIZABLE PREPOLYMER COMPOSITION FOR OPTICAL MATERIAL, CURED ARTICLE, AND METHOD FOR PRODUCING OPTICAL MATERIAL

EP4741436A1EP 4741436 A1EP4741436 A1EP 4741436A1EP-4741436-A1

Abstract

The polymerizable composition for an optical material of the present disclosure includes two or more different monomers for an optical material, at least one of which is an isocyanate compound, a basic polymerization catalyst, and an organic acid having a pKa value of less than 4, and has a viscosity of from 10 mPa·s to 1000 mPa·s as measured at 25°C and 60 rpm using a B-type viscometer.

Inventors

  • MATSUI, YUSUKE
  • ITO, SHINSUKE

Assignees

  • Mitsui Chemicals, Inc.

Dates

Publication Date
20260513
Application Date
20240821

Claims (20)

  1. A polymerizable composition for an optical material, the composition comprising two or more different monomers for an optical material, a basic polymerization catalyst, and an organic acid having a pKa value of less than 4, at least one of the two or more different monomers for an optical material being an isocyanate compound, and the composition having a viscosity of from 10 mPa·s to 1000 mPa·s as measured at 25°C and 60 rpm using a B-type viscometer.
  2. The polymerizable composition for an optical material according to claim 1, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having an aromatic ring, and a content of the basic polymerization catalyst is from 0.010 parts by mass to 0.50 parts by mass with respect to a total of 100 parts by mass of the two or more different monomers for an optical material.
  3. The polymerizable composition for an optical material according to claim 1, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having no aromatic ring, and a content of the basic polymerization catalyst is from more than 0.05 parts by mass to 2.0 parts by mass with respect to a total of 100 parts by mass of the two or more different monomers for an optical material.
  4. The polymerizable composition for an optical material according to claim 1, further comprising a prepolymer that is a polymer of the two or more different monomers for an optical material and that has a polymerizable functional group.
  5. The polymerizable composition for an optical material according to claim 1, wherein the two or more different monomers for an optical material further include at least one active hydrogen compound selected from the group consisting of a polythiol compound having at least two mercapto groups, a hydroxythiol compound having at least one mercapto group and at least one hydroxy group, a polyol compound having at least two hydroxy groups, and an amine compound.
  6. The polymerizable composition for an optical material according to claim 1, wherein at least one of the two or more different monomers for an optical material is an active hydrogen compound, and a total proportion of the isocyanate compound and the active hydrogen compound with respect to an entirety of the two or more different monomers for an optical material exceeds 70% by mass.
  7. The polymerizable composition for an optical material according to claim 1, wherein a molar number of functional groups of the organic acid having a pKa value of less than 4 is smaller than a molar number of functional groups of the basic polymerization catalyst.
  8. The polymerizable composition for an optical material according to claim 1, wherein the basic polymerization catalyst includes a basic polymerization catalyst having a pKa value of from 4 to 8.
  9. A polymerizable prepolymer composition for an optical material, the composition comprising a prepolymer that is a polymer of two or more different monomers for an optical material and that has a polymerizable functional group, a basic polymerization catalyst, and an organic acid having a pKa value of less than 4, at least one of the two or more different monomers for an optical material being an isocyanate compound, and the composition having a viscosity of from 10 mPa·s to 2000 mPa·s as measured at 25°C and 60 rpm using a B-type viscometer.
  10. The polymerizable prepolymer composition for an optical material according to claim 9, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having an aromatic ring, and a content of the basic polymerization catalyst is from 0.002 parts by mass to 1 part by mass with respect to a total of 100 parts by mass of the prepolymer.
  11. The polymerizable prepolymer composition for an optical material according to claim 9, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having no aromatic ring, and a content of the basic polymerization catalyst is from 0.1 parts by mass to 4.0 parts by mass with respect to a total of 100 parts by mass of the prepolymer.
  12. A cured product of the polymerizable composition for an optical material according to claim 1 or of the polymerizable prepolymer composition for an optical material according to claim 9.
  13. A method for producing an optical material, the method comprising: a preparation process of preparing a polymerizable composition for an optical material comprising two or more different monomers for optical materials, a basic polymerization catalyst, and an organic acid having a pKa value of less than 4, at least one of the two or more different monomers for an optical material being an isocyanate compound; a casting process of adjusting a viscosity of the polymerizable composition for an optical material to from 10 mPa·s to 1000 mPa·s as measured at 25°C and 60 rpm using a B-type viscometer, and casting the polymerizable composition for an optical material into a mold; and a curing process of curing the polymerizable composition for an optical material by polymerizing the two or more different monomers for an optical material in the mold.
  14. The method for producing an optical material according to claim 13, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having an aromatic ring, and a content of the basic polymerization catalyst is from 0.010 parts by mass to 0.50 parts by mass with respect to a total of 100 parts by mass of the two or more different monomers for optical materials.
  15. The method for producing an optical material according to claim 13, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having no aromatic ring, and a content of the basic polymerization catalyst is from more than 0.05 parts by mass to 2.0 parts by mass with respect to a total of 100 parts by mass of the two or more different monomers for an optical material.
  16. A method for producing an optical material, the method comprising: a preparation process of preparing two or more different monomers for an optical material and a basic polymerization catalyst, at least one of the two or more different monomers for an optical material being an isocyanate compound; a prepolymerization process of obtaining a prepolymer by mixing a part of the two or more different monomers for an optical material with at least a part of the basic polymerization catalyst, and at least partly polymerizing the part of the two or more different monomers for an optical material, thereby obtaining a mixture containing the prepolymer; and an acid addition process of adding an organic acid having a pKa value of less than 4 to the mixture containing the prepolymer.
  17. The method for producing an optical material according to claim 16, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having an aromatic ring, a total amount of the two or more different monomers for an optical material is 100 parts by mass, and an amount of the basic polymerization catalyst is from 0.010 parts by mass to 0.50 parts by mass.
  18. The method for producing an optical material according to claim 16, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having no aromatic ring, a total amount of the two or more different monomers for an optical material is 100 parts by mass, and an amount of the basic polymerization catalyst is from more than 0.05 parts by mass to 2.0 parts by mass.
  19. The method for producing an optical material according to claim 16, further comprising: a polymerizable composition production process of obtaining a polymerizable composition for an optical material containing the two or more different monomers for an optical material, the prepolymer, the basic polymerization catalyst, and the organic acid having a pKa value of less than 4, by adding at least a remainder of the two or more different monomers for an optical material to the mixture containing the prepolymer; and a curing process of curing the two or more different monomers for an optical material in the polymerizable composition to obtain an optical material that is a cured product of the polymerizable composition.
  20. A cured product of two or more different monomers for an optical material, at least one of the two or more different monomers for an optical material being an isocyanate compound, the cured product having no striation with a length of 1.0 mm or more within a radius of 15 mm from the center of the cured product, and the cured product having a content of amine measured by gas chromatography-mass spectrometry of more than 0% by mass, and a content of an organic acid having a pKa value of less than 4 measured by gas chromatography-mass spectrometry of more than 0% by mass.

Description

[Technical Field] The present invention relates to a polymerizable composition for an optical material, a polymerizable prepolymer composition for an optical material, a cured article, and a method for producing an optical material. [Background Art] As a method for producing a resin used as an optical material for plastic lenses, a cast polymerization method may be employed, in which a polymerizable composition containing a monomer is poured into a mold and cured by heating. In the cast polymerization method, a polymerizable composition is prepared and degassed, the polymerizable composition is then poured into a mold, and after heat curing (a polymerization reaction), the resulting product is removed from the mold (demolding) and subjected to annealing, thereby obtaining an optical material (for example, a lens or a semi-finished blank). In the cast polymerization method, in order to improve the quality of the optical material, it is common to carry out the polymerization reaction over a long period of time (for example, about 20 to 48 hours) while gradually increasing the temperature of the polymerizable composition by heating. For this reason, it is known that a large proportion (for example, about 90%) of the total time required for manufacturing the optical material is consumed by the heat polymerization process. In the examples of Patent Document 1, a process is described in which a mold into which a polymerizable composition had been poured was gradually heated from 10°C to 120°C, and polymerization was effected over 20 hours to obtain a molded article. In the examples of Patent Document 2, a process is described in which a mold into which a polymerizable composition had been poured was gradually heated from 25°C to 120°C over 16 hours, and then heated at 120°C for 4 hours to obtain a molded article. [Prior Art Document] [Patent Document] Patent Document 1: International Publication No. WO 2014/027427Patent Document 2: International Publication No. WO 2014/133111 [Summary of the Invention] [Problem to be Solved by the Invention] The polymerizable compositions used in the methods described in Patent Document 1 and Patent Document 2 exhibit a rapid increase in viscosity after preparation and, therefore, still have room for improvement in terms of pot life (usable time). One object to be achieved by an embodiment of the present disclosure is to provide a polymerizable composition and a polymerizable prepolymer composition that enable a reduction in the manufacturing time of optical materials and that exhibit excellent pot life. Another object to be achieved by an embodiment of the present disclosure is to provide a method for producing an optical material using the foregoing polymerizable composition or polymerizable prepolymer composition, and a cured product obtained by using the foregoing polymerizable composition or polymerizable prepolymer composition. [Means for Solving the Invention] <1> A polymerizable composition for an optical material, the composition including two or more different monomers for an optical material, a basic polymerization catalyst, and an organic acid having a pKa value of less than 4, at least one of the two or more different monomers for an optical material being an isocyanate compound, and the composition having a viscosity of from 10 mPa·s to 1000 mPa·s as measured at 25°C and 60 rpm using a B-type viscometer.<2> The polymerizable composition for an optical material according to <1>, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having an aromatic ring, anda content of the basic polymerization catalyst is from 0.010 parts by mass to 0.50 parts by mass with respect to a total of 100 parts by mass of the two or more different monomers for an optical material.<3> The polymerizable composition for an optical material according to <1>, wherein: at least one of the two or more different monomers for an optical material is an isocyanate compound having no aromatic ring, anda content of the basic polymerization catalyst is from more than 0.05 parts by mass to 2.0 parts by mass with respect to a total of 100 parts by mass of the two or more different monomers for an optical material.<4> The polymerizable composition for an optical material according to any one of <1> to <3>, further including a prepolymer that is a polymer of the two or more different monomers for an optical material and that has a polymerizable functional group.<5> The polymerizable composition for an optical material according to any one of <1> to <4>, wherein the two or more different monomers for an optical material further include at least one active hydrogen compound selected from the group consisting of a polythiol compound having at least two mercapto groups, a hydroxythiol compound having at least one mercapto group and at least one hydroxy group, a polyol compound having at least two hydroxy groups, and an amine compound.<6> The polymerizabl