Compositions and articles prepared from the thioether functional oligomeric polythiols

• US 7,696,296 B2
• Filed: 05/04/2007
• Issued: 04/13/2010
• 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: McCollum, Gregory J., Bojkova, Nina V., Rukavina, Thomas G.
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): LEONARD, MICHAEL L
• Application Number:
  US11/744,240
• Publication Number:
  US 20070270548A1
• Time in Patent Office: 1,075 Days
• Field of Search: 528/44, 528/76, 528/78, 528/60, 528/61, 528/63, 528/64, 528/73, 528/80, 525/123, 428/423.1
• US Class Current: 528/76
• 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 composition including a reaction product of:

• • (A) a reactive compound that includes a material having functional groups that are reactive with active hydrogens;
  • (B) a thioether-functional, oligomeric polythiol prepared by reacting together:
    • (1) a compound having at least two thiol functional groups;
    • (2) a compound having triple bond functionality; and optionally
    • (3) a compound having at least two double bonds; and, optionally,
  • (C) a compound different from (B) containing active hydrogens. Coating compositions, articles of manufacture and related processes also are provided.

Claims

1. A composition comprising a reaction product of:

(A) a reactive compound comprising a polyisocyanate, a blocked polyisocyanate, a polyisothiocyanate, a polyepoxide, a polyepisulfide, a polyacid, an anhydride, a polyanhydride, and/or a polyethylenically unsaturated material;

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

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

(2) a compound having triple bond functionality selected from propargyl alcohol, propargyl chloride, propargyl bromide, propargyl acetate, propargyl propionate, propargyl benzoate, phenyl propargyl sulfide, 1,4-dichloro-2-butyne, 2-butyne-1,4-diol, 3-butyne-2-ol, 3-hexyne-2,5-diol, and mixtures thereof; and

optionally

(3) a compound having at least two double bonds; and

, optionally

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

2. The composition of claim 1, wherein the reactive compound (A) comprises a diisocyanate or a mixture of a diisocyanate and a polyisocyanate having more than two isocyanate functional groups.

3. The composition of claim 2 wherein the reactive compound (A) comprises a mixture of a diisocyanate and a polyisocyanate having more than two isocyanate functional groups, wherein the polyisocyanate having more than two isocyanate functional groups is present in an amount up to 20 percent by weight of the mixture.

4. The composition of claim 2 wherein the reactive compound (A) comprises methylene bis(4-cyclohexyldiisocyanate), 1,3-bis(1-isocyanato-1-methylethyl)-benzene, m-xylylene diisocyanate, hexamethylene diisocyanate, 1,3-isocyanato methyl cyclohexane, and/or 3-isocyanato-methyl-3,5,5-trimethyl cyclohexyl-isocyanate.

5. The composition of claim 1 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.

6. The composition of claim 5 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.

7. The composition of claim 1 wherein the compound (1) having at least two thiol functional groups further contains hydroxyl functionality.

8. The composition of claim 1 wherein the thiol functional groups in compound (1) are terminal groups.

9. The composition of claim 1, wherein the compound (3) having at least two double bonds is present and comprises acyclic non-conjugated dienes, acyclic polyvinyl ethers, allyl-(meth)acrylates vinyl-(meth)acrylates, di(meth)acrylate esters of diols, di(meth)acrylate esters of dithiols, di(meth)acrylate esters of poly(alkyleneglycol) diols, monocyclic non-aromatic dienes, polycyclic non-aromatic dienes, aromatic ring-containing dienes, diallyl esters of aromatic ring dicarboxylic acids, and/or divinyl esters of aromatic ring dicarboxylic acids.

10. The composition of claim 9, wherein the compound (3) having at least two double bonds comprises 5-vinyl-2-norbornene, ethylene glycol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, butane diol divinyl ether, vinylcyclohexene, 4-vinyl-1-cyclohexene, dipentene, terpinene, dicyclopentadiene, cyclododecadiene, cyclooctadiene, 2-cyclopenten-1-yl-ether, 2,5-norbornadiene, divinylbenzene, diisopropenylbenzene, allyl (meth)acrylate, ethanediol di(meth)acrylate, 1,3-propanediol di(meth)acrylate, 1,2-propanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,2-butanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, 2,2-thioethanedithiol di(meth)acrylate, and/or 1,2-ethanedithiol di(meth)acrylate.

11. The composition of claim 10, wherein the compound (C) comprises a compound having at least two active hydrogen-containing groups comprising primary amine groups, secondary amine groups, hydroxyl groups, and/or thiol groups.

12. The composition of claim 11, wherein the compound (C) comprises diethyltoluenediamine and/or a compound having at least two thiol functional groups.

13. A coating composition comprising the composition of claim 1.

14. An article of manufacture comprising the composition of claim 1.

15. The article of claim 14, wherein said article is an optical article.

16. The article of claim 15, wherein the optical article possesses at least one light influencing property.

17. The article of claim 16, wherein the optical article is photochromic.

18. The composition of claim 1, wherein the reaction product is prepared in the presence of a urethanation catalyst.

19. The composition of claim 18, where in the urethanation catalyst is selected from the group consisting of Lewis bases, Lewis acids, insertion catalysts, stannous octoate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin mercaptide, dibutyl tin dimaleate, dimethyl tin diacetate, dimethyl tin dilaurate, dibutyltin dichloride, 1,4-diazabicyclo[2.2.2]octane, zinc octoate, bismuth, ferric acetylacetonate, phosphines, tertiary ammonium salts, tertiary amines, and mixtures thereof.