Method of bonding a metal or alloy utilizing a polymerizable thiocarboxylic acid or a derivative thereof

• US 5,254,198 A
• Filed: 06/03/1992
• Issued: 10/19/1993
• Est. Priority Date: 06/20/1988
• Status: Expired due to Term

• Current Assignee: Kuraray Company Limited
• Original Assignee: Kuraray Company Limited
• Inventors: Omura, Ikuo, Kawashima, Mitsunobu
• Primary Examiner(s): HENDERSON JR, CHRISTOPHER A
• Application Number:
  US07/892,928
• Time in Patent Office: 503 Days
• Field of Search: 156/307.3, 156/327, 156/331.1
• US Class Current: 156/307.3
• CPC Class Codes: A61K 6/30 Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
• CPC Class Codes: A61K 6/40 Primers for dental adhesives A61K6/30
• CPC Class Codes: C08F 218/00 Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
• CPC Class Codes: C08F 220/38 Esters containing sulfur
• CPC Class Codes: C08F 222/1006 of polyhydric alcohols or polyhydric phenols
• CPC Class Codes: C08F 228/00 Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
• CPC Class Codes: C08L 25/08 Copolymers of styrene C08L29/08, C08L35/06, C08L55/02 take precedence
• CPC Class Codes: C08L 27/06 Homopolymers or copolymers of vinyl chloride
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 33/14 of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C08L 33/26 Homopolymers or copolymers of acrylamide or methacrylamide
• CPC Class Codes: C09J 4/00 Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16

Abstract

An adhesive composition comprising a polymerizable thiocarboxylic acid or a derivative thereof of the general formula ##STR1## wherein X₁ is an oxygen atom or a sulfur atom and where X₁ is an oxygen atom, R₁ is an organic group containing at least one olefinic double bond and R₂ is a mercapto group, and where X₁ is a sulfur atom, R₁ is an organic group and R₂ is a mercapto group, a halogen atom, --OR₃, or --SR₃, where R₃ is a monovalent organic group, and at least one of R₁ and R₃ has at least one olefinic double bond, are useful as primers or adhesives and provide a water-resistant, high-strength bond to noble metal adherends which are used in dental and other applications.

Claims

1. A method of bonding a metal or alloy to another material, comprising:

(i) applying an adhesive composition to said metal or alloy to obtain an adhesive coated metal or alloy; and

(ii) contacting said another material with said adhesive coated metal;

wherein said adhesive composition comprises a polymerizable thiocarboxylic acid or derivative thereof of the formula;

##STR48## wherein R₄ is hydrogen or methyl;

R₆ is a hydrocarbon group of 1 to 40 carbon atoms which can be substituted with --OH, --C═

N, --NH₂, --SO₃ H, halogen, --COOH, --CSSH or --COSH;

Y is --COO--, --OOC--, --CONH--, --COS--, --SOC--, --S-- or ##STR49## R₂ is --SH or --SR₃, where R₃ is a hydrocarbon group of the formula ##STR50## wherein R₄ '"'"' is the same as R₄ ;

R₆ '"'"' is the same as R₆ ;

Y'"'"' is the same as Y;

with the proviso that when Y is --COO--, --OOC--, --CONH--, --COS--, --SOC-- or --S--, n is 1;

when Y is ##STR51## n is 0 or 1;

when R₂ is --SH, then m is 1;

that when R₂ is --SR₃, m is 0 or 1;

that m+n≧

1;

that when Y'"'"' is --COO, --OOC, --CONH--, --COS--, --SOC-- and --S--, n¹ is 1;

that when Y'"'"' is ##STR52## n'"'"'is 0 is 1;

that m'"'"' is 0 or 1;

m'"'"'+n'"'"'≧

1; and

m+m≧

1.