Plastic lenses having a high-refractive index, process for the preparation thereof and casting polymerization process for preparing sulfur-containing urethane resin lens and lens prepared thereby

• US 5,753,730 A
• Filed: 05/15/1991
• Issued: 05/19/1998
• Est. Priority Date: 12/15/1986
• Status: Expired due to Term

• Current Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Original Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Inventors: Sasagawa, Katsuyoshi, Kanemura, Yoshinobu, Kajimoto, Nobuyuki, Miura, Tohru, Okazaki, Koju, Imai, Masao, Nagata, Teruyuki
• Primary Examiner(s): Michl, Paul R.
• Assistant Examiner(s): Cain, Edward J.
• Application Number:
  US07/700,508
• Time in Patent Office: 2,561 Days
• Field of Search: 524/136, 528/67, 528/76, 528/77, 528/79, 528/80, 528/81, 528/85
• US Class Current: 524/136
• CPC Class Codes: B29C 33/60 Releasing, lubricating or separating agents in general C10M
• CPC Class Codes: C08G 18/3863 containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/75 cycloaliphatic
• CPC Class Codes: C08G 18/7628 containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
• CPC Class Codes: C08K 5/02 Halogenated hydrocarbons C08K5/0091 takes precedence
• CPC Class Codes: C08K 5/098 Metal salts of carboxylic acids
• CPC Class Codes: C08K 5/19 Quaternary ammonium compounds
• CPC Class Codes: C08K 5/521 Esters of phosphoric acids, e.g. of H3PO4
• CPC Class Codes: C08K 5/54 Silicon-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08L 75/00 Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/041 Lenses

Abstract

One aspect of the present invention relates to a process for preparing plastic lenses having a high-refractive index comprising forming a mixture containing one or more polyisocyanate compounds; one or more active hydrogen compounds selected from the group consisting of a polyol compound having no sulfur atom, a polyol compound having at least one sulfur atom, and a polythiol compound having at least one sulfur atom in addition to the sulfur atom contained in mercapto group and at least one internal releasing agent and then casting and polymerizing the mixture.

A second aspect of the present invention relates to a process for preparing a sulfur-containing urethane resin lens is here disclosed which comprises mixing polyisocyanate having two or more isocyanato groups, polythiol having two or more thiol groups and one or more surface active agent selected from the group consisting of fluorine-containing nonionic surface active agents, silicone-containing nonionic surface active agents, alkyl quaternary ammonium salts and acid phosphoric esters and then cast polymerizing the mixture in a mold made of a glass or a metal. Lenses prepared by the processes are also disclosed.

Claims

1. A process for preparing a polyurethane lens which comprises:

(a) forming a mixture of a polyisocyanate, a polythiol, and an acid phosphoric ester selected from the group consisting of diisopropyl acid phosphate, dibutyl acid phosphate and dioctyl acid phosphate, and

(b) subjecting the mixture containing the acid phosphoric ester obtained in step (a) to cast polymerization in a mold for a plastic lens to obtain a polyurethane lens.

2. A lens prepared by the process of claim 1.

3. A process for producing a plastic lens comprising adding at least one acid phosphoric ester as an internal mold releasing agent to a mixture of one or more polyisocyanate compounds and one or more active hydrogen compounds selected from the group consisting of polyol compounds and polythiol compounds having at least one sulfur atom in addition to the mercapto groups and conducting cast polymerization in a lens mold so as to form a plastic lens.

4. The process for producing a plastic lens of claim 3 wherein the acid phosphoric ester has i) one or two alkyl groups of 3-13 carbon atoms, ii) O═

bonded to P, and iii) one or two hydroxyl groups bonded to P wherein if the acid phosphoric ester has one alkyl group then two hydroxyl groups are bonded to P and if the acid phosphoric ester has two alkyl groups then one hydroxyl group is bonded to P.

5. A plastic lens produced by the process of claim 3.

6. The process of claim 3 wherein the polyol compounds are sulfur-containing polyol compounds.

7. A plastic lens produced by the process of claim 6.

8. The process of claim 3 wherein the proportion of the polyisocyanate compound to the active hydrogen compound is a molar ratio of from about 0.5 to about 3.0 moles of functional isocyanate group per mole of functional (SH+OH) group.

9. A plastic lens produced by the process of claim 8.

10. The process of claim 3 wherein the internal mold releasing agent is present in an amount of from about 0.1 to about 10,000 ppm per sum of the polyisocyanate compound and the active hydrogen compound.

11. A plastic lens produced by the process of claim 10.

12. The process of claim 3 wherein cast polymerization is carried out at a temperature of from about -50°

C. to about 200°

C.

13. The process of claim 3 wherein the acid phosphoric ester is selected from the group consisting of isopropyl acid phosphate, diisopropyl acid phosphate, butyl acid phosphate, dibutyl acid phosphate, octyl acid phosphate, dioctyl acid phosphate, isodecyl acid phosphate, diisodecyl acid phosphate, tridecyl acid phosphate and bis(tridecyl) acid phosphate.

14. A process for preparing a sulfur-containing urethane resin lens which comprises pouring a mixture of polyisocyanate having two or more isocyanato groups, polythiol having two or more thiol groups, and one or more acidic phosphate esters into a mold made of a glass or metal, heating and cast polymerizing the same.

15. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein the acid phosphoric esters has i) one or two alkyl groups of 3-13 carbon atoms, ii) O═

bonded to P, and iii) one or two hydroxyl groups bonded to P wherein if the acid phosphoric ester has one alkyl group then two hydroxyl groups are bonded to P and if the acid phosphoric ester has two alkyl groups then one hydroxyl group is bonded to P.

16. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein said polyisocyanate is one or more polyisocyanates selected from the group consisting of aliphatic polyisocyanates, aliphatic polyisocyanates having an aromatic ring and alicyclic polyisocyanates.

17. The process for preparing a sulfur-containing urethane resin lens of claim 15 wherein said aliphatic polyisocyanate, aliphatic polyisocyanate having an aromatic ring or alicyclic polyisocyanate is one or more polyisocyanates selected from the group consisting of xylylene diisocyanate, bis(α

,α

-dimethyl isocyanato methyl)benzene, isophorone diisocyanate and hexamethylene diisocyanate.

18. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein said polythiol is at least one polythiol selected from the group consisting of aliphatic polythiols, alicyclic polythiols, polythiols having an aromatic ring, polythiols having a heterocyclic ring and halogen-substituted compounds of these polythiols.

19. The process for preparing a sulfur-containing urethane resin lens of claim 18 wherein said polythiol is a polythiol having at least three thiol groups.

20. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein said polythiol is one or more polythiols selected from the group consisting of pentaerythritol tetrakis(3-mercapto-propionate), dipentaerythritol hexakis(3-mercapto-propionate), xylylenedithiol and 1,3,5 tris(3-mercapto-propyl) isocyanurate.

21. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein said surface active agent is present in an amount of from about 1 ppm to about 10,000 ppm with respect to the total weight of the polyisocyanate and the polythiol.

22. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein said surface active agent is present in an amount of from about 1 ppm to about 5,000 ppm with respect to the total weight of the polyisocyanate and the polythiol.

23. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein the ratio of said polyisocyanate to said polythiol is from about 0.5:

1.0 to about 3.0;

1.0 in terms of an NCO/SH equivalent ratio.

24. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein the ratio of said polyisocyanate to said polythiol is from about 0.5:

1.0 to about 1.5;

1.0 in terms of an NCO/SH equivalent ratio.

25. The process for preparing a sulfur-containing urethane resin lens of claim 14 wherein the acid phosphoric ester is selected from the group consisting of isopropyl acid phosphate, diisopropyl acid phosphate, butyl acid phosphate, dibutyl acid phosphate, octyl acid phosphate, dioctyl acid phosphate, isodecyl acid phosphate, diisodecyl acid phosphate, tridecyl acid phosphate and bis(tridecyl) acid phosphate.

26. A lens prepared by the process of claim 14.