UV/EB curable copolymers for lithographic and corrosion-resistant coating applications

• US 5,376,503 A
• Filed: 11/24/1992
• Issued: 12/27/1994
• Est. Priority Date: 12/20/1990
• Status: Expired due to Fees

• Current Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: Exxon Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: McElrath, Kenneth O., Audett, Jay D.
• Primary Examiner(s): BRAMMER, JACK
• Application Number:
  US07/982,104
• Time in Patent Office: 763 Days
• Field of Search: 430/18, 430/270, 430/281, 430/286, 430/905, 430/907, 430/913, 430/915, 430/916, 522/35, 522/48, 522/53, 522/57, 522/160, 522/904, 522/905
• US Class Current: 430/270.1
• CPC Class Codes: C08F 210/00 Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
• CPC Class Codes: C08F 212/06 Hydrocarbons
• CPC Class Codes: C08F 8/00 Chemical modification by after-treatment graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C
• CPC Class Codes: C08L 23/22 Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
• CPC Class Codes: G03F 7/0388 with ethylenic or acetylenic bands in the side chains of the photopolymer
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials
• CPC Class Codes: Y10S 430/106 Binder containing
• CPC Class Codes: Y10S 430/114 Initiator containing
• CPC Class Codes: Y10S 430/116 Redox or dye sensitizer
• CPC Class Codes: Y10S 430/117 Free radical
• CPC Class Codes: Y10S 522/904 Monomer or polymer contains initiating group
• CPC Class Codes: Y10S 522/905 Benzophenone group

Abstract

A lithographic coating and method of framing a lithographic image are disclosed. The method comprises coating at least a portion of a surface of an article with a radiation-crosslinkable polymer, and exposing the coated surface to a pattern of radiation to crosslink the polymer in a lithographic image. The functionalized polymer is a copolymer of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene, wherein the para-alkylstyrene is functionalized with a radiation reactive group at the para-alkyl group of the para-alkylstyrene.

Claims

1. A coating composition comprising:

a) 50 to 100 parts by weight of a random copolymer of an isoolefin having 4 to 7 carbon atoms and a para-alkylstyrene, said isoolefin comprising 10 to 99.5 wt. % of said copolymer and said para-alkylstyrene comprises from 0.5 to 90 wt. % of said copolymer, wherein about 0.5 to 55 wt. % of said polymer comprises para-alkylstyrene monomers having a photo-initiator substituted on the pendent alkyl group; and

b) 0 to 50 parts by weight of a tackifier;

a polymer which does not contain a photo-initiator or mixtures of said tackifier and said polymer.

2. The coating composition defined in claim 1 wherein said random copolymer has a number average molecular weight of between 5,000 and 500,000.

3. The coating composition defined in claim 1 wherein said isoolefin is isobutylene and said para-alkylstyrene is para-methylstyrene.

4. The coating composition defined in claim 1 wherein said photo-initiator is selected from the group consisting of benzoic acid, cinnamic acid, m-nitrocinnamic acid, p-chlorocinnamic acid, p-methoxycinnamic acid, chalcone acrylic acid, p-phenylenebis(acrylic acid), p-azidobenzoic acid, p-sulfonazidebenzoic acid, alpha cyanocinnamic acid, cinnamylideneacetic acid, cinnamylidenemalonic acid, alpha cyanocinnamylidene-acetic acid, β

-(1)-naphthylacrylic acid, β

-(2)-furfurylacrylic acid, alpha cyanothienylacrylic, β

(1)-naphthylacrylic acid, β

-(9)-anthrylacrylic acid, and esters and salts thereof.

5. The coating composition defined in claim 1 wherein said photo-initiator is a nucleophilically substituted photo-initiator selected from the group consisting of benzophenone, 4-chlorobenzophenone, 4-hydroxybenzophenone, benzoquinone, naphthaquinone, anthraquinone, 2-chloroanthraquinone, benzyldiene acetophenone, acetophenone, propiophenone, cyclopropyl phenyl katone, benzaldehyde, β

-naphthylphenylketone, β

-naphthaldehyde, β

-acetonaphthone, 2,3 pentanedione, benzyl, fluorenone, benzanthrone, Michler'"'"'s ketone, bis(parahydroxybenzylidene)acetone, benzoin, deoxybenzoin, and chlorodeoxybenzoin.

6. The coating composition defined in claim 1 wherein said photo-initiator comprises nucleophilically substituted thioxanthone.

7. The coating composition defined in claim 1 wherein said photo-initiator is a nucleophilically substituted photo-initiator selected from N,N-disubstituted dithiocarbamic acid and esters and salts thereof.

8. A coating composition comprising:

a) 50 to 100 parts by weight of a random copolymer of a C₄ to C₇ isoolefin and a para-alkylstyrene said para-alkylstyrene having the general structure;

##STR49## wherein R and R'"'"' are independently selected from the group consisting of hydrogen, alkyl and primary and secondary alkyl halides and is selected from the group comprising hydrogen, a photo-initiator, X or Z wherein X is either bromine or chlorine and Z is a functionality which is not a photo-initiator and which contains oxygen, sulfur, silicon, nitrogen, carbon or metal, said metal selected from the group consisting of sodium, potassium, lithium and magnesium wherein said para-alkylstyrene containing photo-initiator comprises from about 0.5 to 55 wt. % of said copolymer, said para-alkylstyrene containing X comprises 0 to 55 wt. % of said copolymer and said para-alkylstyrene containing Z comprises 0 to 55 wt. % of said copolymer; and

b) a tackifier.