THIOETHER FUNCTIONAL OLIGOMERIC POLYTHIOLS AND ARTICLES PREPARED THEREFROM

• US 20080125525A1
• Filed: 05/04/2007
• Published: 05/29/2008
• Est. Priority Date: 05/05/2006
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Bojkova, Nina V.
• Granted Patent: US 7,687,597 B2
• Time in Patent Office: Days
• US Class Current: 524/114
• CPC Class Codes: C08G 18/3234 cycloaliphatic
• CPC Class Codes: C08G 18/324 containing only one aromatic ring
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/722 Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/758 containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 18/765 alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
• CPC Class Codes: C08G 75/045 from mercapto compounds and unsaturated compounds
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 75/04 Polyurethanes
• 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 81/02 Polythioethers; Polythioether-ethers
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Abstract

Provided is a thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together: (a) a compound having at least two thiol functional groups; and (b) a hydroxyl functional compound having triple bond functionality. Also provided are optical articles prepared from the reaction product of: (A) a reactive compound having functional groups that are reactive with active hydrogens; (B) a thioether-functional, oligomeric polythiol; and, optionally, (C) a compound different from (B) containing active hydrogens.

Claims

1. A thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together:

(a) a compound having at least two thiol functional groups; and

(b) a hydroxyl functional compound having triple bond functionality.

2. The oligomeric polythiol of claim 1 wherein the compound (a) having at least two thiol functional groups comprises a dithiol, a compound having more than two thiol functional groups, or a mixture of a dithiol and a compound having more than two thiol functional groups.

3. The oligomeric polythiol of claim 2 wherein the compound (a) comprises a mixture of a dithiol and a compound having more than two thiol functional groups, wherein the compound having more than two thiol functional groups is present in an amount up to 10 percent by weight of the mixture.

4. The oligomeric polythiol of claim 1 wherein the compound (a) having at least two thiol functional groups further contains hydroxyl functionality.

5. The oligomeric polythiol of claim 1 wherein the thiol functional groups in compound (a) are terminal groups.

6. The oligomeric polythiol of claim 1 wherein the ratio of thiol functional groups to triple bonds is from 1.01:

1 to 5.0;

1.

7. The oligomeric polythiol of claim 1 wherein the compound (b) having triple bond functionality comprises propargyl alcohol, 2-butyne-1,4-diol, 3-butyne-2-ol, and/or 3-hexyne-2,5-diol.

8. The oligomeric polythiol of claim 1 wherein at least a portion of hydroxyl functional groups on the compound (b) are esterified.

9. A rigid optical article comprising a reaction product of:

(A) a reactive compound comprising a material having functional groups that are reactive with active hydrogen groups;

(B) a thioether-functional, oligomeric polythiol having pendant hydroxyl functional groups, prepared by reacting together;

(1) a compound having at least two thiol functional groups; and

(2) a hydroxyl functional compound having triple bond functionality; and

optionally

(C) a compound different from (B) containing active hydrogens.

10. The optical article of claim 9, wherein the reactive compound (A) comprises a polyisocyanate, a blocked polyisocyanate, a polyisothiocyanate, a polyepoxide, a polyepisulfide, a polyacid, an anhydride, a polyanhydride, and/or a polyethylenically unsaturated material.

11. The optical article of claim 9, wherein said optical article possesses at least one light influencing property.

12. The optical article of claim 11, wherein said optical article is photochromic.

13. The optical article of claim 9, wherein the compound (C) is present and comprises a compound having at least two active hydrogen-containing groups comprising primary amine groups, secondary amine groups, hydroxyl groups, and/or thiol groups.

14. A rigid optical article comprising a reaction product of:

(A) a reactive compound comprising a material having functional groups that are reactive with active hydrogen groups;

(B) a thioether-functional, oligomeric polythiol prepared by reacting together;

(1) a compound having at least two thiol functional groups; and

(2) a compound having triple bond functionality; and

optionally

(C) a compound different from (B) containing active hydrogens.

15. The optical article of claim 14, wherein the reactive compound (A) comprises a polyisocyanate, a blocked polyisocyanate, a polyisothiocyanate, a polyepoxide, a polyepisulfide, a polyacid, an anhydride, a polyanhydride, and/or a polyethylenically unsaturated material.

16. The optical article of claim 14, wherein the compound (C) is present and comprises a compound having at least two active hydrogen-containing groups comprising primary amine groups, secondary amine groups, hydroxyl groups, and/or thiol groups.

17. The optical article of claim 14 wherein the compound (1) having at least two thiol functional groups comprises a dithiol, a compound having more than two thiol functional groups, or a mixture of a dithiol and a compound having more than two thiol functional groups.

18. The optical article of claim 17 wherein the compound (1) comprises a mixture of a dithiol and a compound having more than two thiol functional groups, wherein the compound having more than two thiol functional groups is present in an amount up to 10 percent by weight of the mixture.

19. The optical article of claim 14 wherein the compound (1) having at least two thiol functional groups further contains hydroxyl functionality.

20. The optical article of claim 14 wherein the thiol functional groups in compound (1) are terminal groups.

21. The optical article of claim 14, wherein the compound (2) having triple bond functionality comprises propargyl alcohol, propargyl chloride, propargyl bromide, propargyl acetate, propargyl propionate, propargyl benzoate, phenyl acetylene, phenyl propargyl sulfide, 1,4-dichloro-2-butyne, 2-butyne-1,4-diol, 3-butyne-2-ol, 2-pentyne, 1-hexyne, 2-hexyne, 3-hexyne, and/or 3-hexyne-2,5-diol.

22. The optical article of claim 14, wherein said optical article possesses at least one light influencing property.

23. The optical article of claim 22, wherein said optical article is photochromic.