Casting epoxy resin, polythiol and releasing agent to form lens

• US 5,374,668 A
• Filed: 11/08/1993
• Issued: 12/20/1994
• Est. Priority Date: 04/30/1988
• Status: Expired due to Term

• Current Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Original Assignee: Mitsui Toatsu Chemicals Incorporated (Mitsui Chemicals)
• Inventors: Imai, Masao, Sasagawa, Katsuyoshi, Kanemura, Yoshinobu
• Primary Examiner(s): Sellers, Robert E.
• Application Number:
  US08/150,536
• Time in Patent Office: 407 Days
• Field of Search: 523/451, 523/455, 523/456, 523/461, 523/463
• US Class Current: 523/451
• CPC Class Codes: C07C 321/00 Thiols, sulfides, hydropolysulfides or polysulfides
• CPC Class Codes: C08G 59/66 Mercaptans
• CPC Class Codes: C08L 2666/22 Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 81/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 81/04 Polysulfides
• CPC Class Codes: G02B 1/041 Lenses

Abstract

The present invention relates to a polysulfide based resin lens, comprising a mixture of at least one epoxy resin having at least two epoxy groups, and at least one polythiol compound having at least two mercaptan groups, and at least one internal release agent, which is cast polymerized, and the process for preparing the same.

Claims

1. A polysulfide based resin lens having a refractive index of 1.58 to 1.66, comprising forming a mixture consisting essentially of:

a) at least one epoxy resin, which has at least two epoxy groups selected from the group consisting of (i) amine based epoxy resins, (ii) phenol based epoxy resins, (iii) alcohol based epoxy resins, (iv) epoxylated products of unsaturated compounds, (v) glycidyl ester based epoxy resins, (vi) urethane based epoxy resins, (vii) alicyclic epoxy resins, and (viii) heterocyclic ring-containing epoxy resins;

b) at least one polythiol compound which has at least two mercapto groups, selected from the group consisting of (i) aliphatic polythiols, (ii) aromatic polythiols, (iii) heterocyclic ring-containing polythiols, (iv) aliphatic polythiols containing sulfur atoms in addition to mercapto groups, (v) aromatic polythiols containing sulfur atoms in addition to mercapto groups and (vi) heterocyclic ring-containing polythiols containing sulfur atoms in addition to mercapto groups, the mole ratio of the mercapto groups in the polythiol compounds to the epoxy resin being from 0.2 to 1.2 moles of mercapto groups per mole of the sum of functional epoxy groups; and

c) at least one internal releasing agent selected from the group consisting of phosphoric acid esters, alkyl quaternary ammonium salts, silicon based nonionic surface active agents and fluorine based nonionic surface active agents, at a concentration of 1 to 10,000 ppm per the total weight of the epoxy resin and the polythiol compound, and then cast-polymerizing said mixture in a mold, and releasing a lens from the mold.

2. The lens of claim 1 wherein the fluorine based nonionic surface active agent is a compound having a perfluoroalkyl group and having a hydroxyalkyl group or phosphoric acid ester group.

3. The lens of claim 1 wherein the silicon based nonionic surface active agent is a compound having a dimethylpolysiloxane group and having a hydroxyalkyl group or phosphoric acid ester group.

4. The lens of claim 1 wherein said phosphoric acid ester is an acidic phosphoric acid ester.

5. The lens of claim 1 wherein said acidic phosphoric acid ester is at least one compound selected from isopropyl acid phosphate, diisopropyl acid phosphate, butyl acid phosphate, dibutyl acid phosphate, octyl acid phosphate, dioctyl acid phosphate, isodecyl acid phosphate, diisodecyl acid phosphate, tridecanol acid phosphate and bis(tridecanol) acid phosphate.

6. The lens of claim 1 wherein said quaternary ammonium salt is one or more compounds selected from the group consisting of halogen salts, phosphates of trimethylcetyl ammonium, trimethylstearyl ammonium, dimethylethylcetyl ammonium, triethyldodecyl ammonium, trioctylmethyl ammonium and diethylcyclohexyldodecyl ammonium.