Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials having primary hydroxyl content

• US 4,818,776 A
• Filed: 11/06/1985
• Issued: 04/04/1989
• Est. Priority Date: 02/07/1983
• Status: Expired due to Fees

• Current Assignee: Union Carbide Corporation (Dow, Inc.)
• Original Assignee: Union Carbide Corporation (Dow, Inc.)
• Inventors: Koleske, Joseph V.
• Primary Examiner(s): Bleutge, John C.
• Assistant Examiner(s): Koeckert, Arthur H.
• Application Number:
  US06/794,605
• Time in Patent Office: 1,245 Days
• Field of Search: 522/170, 522/31, 528/361, 528/406
• US Class Current: 522/31
• CPC Class Codes: C08G 59/68 characterised by the catalysts used
• CPC Class Codes: C08L 2666/18 Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
• 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: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins

Abstract

This invention is directed to photocopolymerizable compositions comprising an epoxide containing two or more epoxy groups, a poly (active hydrogen) organic compound having at least some primary hydroxyl content and a photoinitiator. The cured coating compositions exhibit fast cure rates, good water resistance and can have utility as automotive finishes, can finishes, appliance finishes, general metal finishes, printing inks, adhesives and the like.

Claims

1. A photocopolymerizable composition having an improved cure rate and when cured resistivity to water comprising a cycloaliphatic epoxide having at least two epoxy groups, a propylene oxide polyol capped with ethylene oxide, which reacts with said epoxide, and a photoinitiator, said capped propylene oxide polyol having an average equivalent weight of about 1439 to about 2078 and an average hydroxyl number of about 27 to about 35.

2. A photocopolymerizable composition as defined in claim 1 wherein the cycloaliphatic epoxide has the formula:

##STR30## wherein R₁ through R₁₈, which can be the same or different, are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive;

R is a valence bond or a divalent hydrocarbon radical generally containing one to twenty carbon atoms inclusive.

3. A photocopolymerizable composition as defined in claim 1 wherein the cycloaliphatic epoxide has the formula:

##STR31## wherein R¹ through R¹⁸, which can be the same or different, are hydrogen or alkyl radicals generally containing one to nine carbon atoms inclusive.

4. A photocopolymerizable composition as defined in claim 1 wherein the cycloaliphatic epoxide has the formula:

##STR32## wherein the R prime and double prime groups are the same or different and are monovalent substituents or monovalent hydrocarbon radicals.

5. A photocopolymerizable composition as defined in claim 1 wherein the cycloaliphatic epoxide is 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate.

6. A photocopolymerizable composition as defined in claim 1 wherein the cycloaliphatic epoxide is bis(3,4-epoxycyclo-hexylmethyl)adipate.

7. A photocopolymerizable composition as defined in claim 1 wheren the cycloaliphatic epoxide is 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-meta-dioxane.

8. A photocopolymerizable composition as defined in claim 1 wherein the cycloaliphatic epoxide is a mixture of bis(3,4-epoxycyclohexylmethyl)adipate and 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)-cyclohexane-meta-dioxane.

9. A photocopolymerizable composition as defined in claim 1 wherein the cycloaliphatic epoxide is a mixture of 3,4-epoxycyclohexylmethyl-3,4-epoxy-cyclohexane carboxylate and bis(3,4-epoxycyclohexylmethyl)adipate.

10. A photocopolymerizable composition as defined in claim 9 which includes 2-(3,4-epoxycyclohexyl)-5,5-spiro-3,4-epoxy)cyclohexane-meta-dioxane.

11. A photocopolymerizable composition as defined in claim 1 wherein the cycloaliphatic epoxide is a mixture of at least two cycloaliphatic epoxides.

12. A photocopolymerizable composition as defined in claim 1 wherein the said polyol is derived from propylene oxide and a trio.

13. A photocopolymerizable composition as defined in claim 1 wherein the triol is glycerol.

14. A photocopolymerizable composition as defined in claim 1 wherein the photoinitiator is selected from the group consisting of triarylsulfonium complex salts, aromatic sulfonium or iodonium salts of halogen-containing complex ions, aromatic onium salts of Group Va or VIa elements, and mixtures thereof.

15. The cured product of the composition defined in claim 1.