Adhesive cyanoacrylate compositions with reduced adhesion to skin

• US 4,444,933 A
• Filed: 12/02/1982
• Issued: 04/24/1984
• Est. Priority Date: 12/02/1982
• Status: Expired due to Term

• Current Assignee: Elmer's Products Incorporated (Newell Brands Inc.)
• Original Assignee: Borden Inc. (Bakelite UK TopCo Ltd.)
• Inventors: Anderson, John, Columbus, Peter S.
• Primary Examiner(s): SECCURO JR, CARMAN J
• Application Number:
  US06/446,254
• Time in Patent Office: 509 Days
• Field of Search: 525/295, 524/292
• US Class Current: 524/292
• CPC Class Codes: C08F 222/322 Alpha-cyano-acrylic acid ethyl ester, e.g. ethyl-2-cyanoacrylate
• CPC Class Codes: C08F 259/00 Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
• CPC Class Codes: C08F 259/04 on to polymers of vinyl chloride
• CPC Class Codes: C08F 263/00 Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00
• CPC Class Codes: C09J 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Abstract

A cyanoacrylate-based adhesive composition comprises 55-92% by weight of a 2-cyanoacrylate ester, preferably the ethyl ester, from 40-30% by weight of a vinyl chloride/vinyl acetate copolymer and not more than 25% by weight of a plasticizer (the plasticizer may be omitted entirely). The copolymer is preferably a vinyl chloride/vinyl acetate/maleic acid terpolymer. The adhesive compositions have greatly reduced adhesion to skin, not forming strong skin bonds for at least 30 seconds, in contrast to conventional cyanoacrylate adhesive compositions which form, within in about one second bonds strong enough to tear skin.

Claims

1. An adhesive composition comprising:

from about 55 to about 92 percent by weight of a 2-cyanoacrylate ester;

from about 4 to about 30 percent by weight of a vinyl chloride/vinyl acetate copolymer dissolved in said 2-cyanoacrylate ester, said copolymer having a molecular weight of at least about 8000 and containing a major proportio by weight of vinyl chloride and a minor proportion, but not less than 5% by weight, of vinyl acetate; and

not more than about 25 percent by weight of a plasticizer.

2. A composition according to claim 1 wherein said cyanoacrylate ester comprises ethyl 2-cyanoacrylate.

3. A composition according to claim 2 wherein said ethyl 2-cyanoacrylate has a viscosity of about 5 to about 50 cPS.

4. A composition according to claim 1 wherein said cyanoacrylate ester comprises from about 75 to about 85 percent by weight of said composition.

5. A composition according to claim 1 wherein said copolymer comprises about 80 to about 90 percent by weight vinyl chloride and about 10 to about 20 percent by weight vinyl acetate.

6. A composition according to claim 1 wherein said copolymer comprises a carboxyl-modified vinyl chloride/vinyl acetate copolymer.

7. A composition according to claim 6 wherein said copolymer comprises a vinyl chloride/vinyl acetate/maleic acid terpolymer.

8. A composition according to claim 7 wherein said terpolymer comprises about 80 to about 90 percent by weight vinyl chloride, about 10 to about 20 percent by weight vinyl acetate and not more than about 2 percent by weight maleic acid.

9. A composition according to claim 1 wherein said copolymer comprises from about 10 to about 18 percent by weight of said composition.

10. A composition according to claim 1 wherein said plasticizer is selected from the group consisting of dipropylene glycol dibenzoate, diethylene glycol dibenzoate, butyl benzyl phthalate, dibutyl phthalate and benzoate esters of di- and poly-hydroxy branched aliphatic compound.

11. A composition according to claim 1 wherein said plasticizer comprises from about 3 to about 8 percent by weight of said composition.

12. A composition according to claim 1 further comprising an anionic polymerization inhibitor.

13. A composition according to claim 12 wherein said anionic polymerization inhibitor comprises sulfur dioxide.

14. A composition according to claim 1 wherein said sulfur dioxide is present in an amount of from about 0.001 to about 0.5 percent by weight of said composition.

15. A composition according to claim 1 further comprising from about 0.001 to about 0.05 percent by weight of a free radical polymerization inhibitor.

16. An adhesive composition comprising:

from about 75 to about 85 percent by weight of ethyl 2-cyanoacrylate;

from about 10 to about 18 percent by weight of a vinyl chloride/vinyl acetate copolymer dissolved in said 2-cyanoacrylate ester, said copolymer having a molecular weight of at least about 8000 and comprising about 80 to about 90 percent by weight vinyl chloride and about 10 to about 20 percent by weight vinyl acetate; and

from about 3 to about 8 percent by weight of a plasticizer.

17. A composition according to claim 16 wherein said ethyl 2-cyanoacrylate has a viscosity of about 5 to about 50 cPs.

18. A composition according to claim 16 wherein said copolymer comprises a carboxyl-modified vinyl chloride/vinyl acetate copolymer.

19. An adhesive composition comprising:

from about 75 to about 85 percent by weight of ethyl 2-cyanoacrylate;

from about 10 to about 18 percent by weight of a vinyl chloride/vinyl acetate/maleic acid terpolymer dissolved in said 2-cyanoacrylate ester, said terpolymer having a molecular weight of at least about 8000 and comprising about 80 to about 90 percent by weight vinylchloride, from about 10 to about 20 percent by weight vinyl acetate and not more than about 2 percent by weight maleic acid; and

from about 3 to about 8 percent by eight of a plasticizer.

20. A composition according to claim 19 wherein said ethyl 2-cyanoacrylate has a viscosity of about 5 to about 50 cPs.

21. A composition according to claim 19 wherein said terpolymer comprises about 83% by weight vinyl chloride, about 16 percent by weight vinyl acetate and about 1 percent by weight maleic acid.

22. A process for forming an adhesive composition, which comprises:

forming a stabilized cyanoacrylate ester composition comprising a 2-cyanoacrylate ester and an anionic polymerization inhibitor; and

dissolving a pulverulent vinyl chloride/vinyl acetate copolymer having a molecular weight of at least about 8000 in said cyanoacrylate composition at a temperature of about 70°

to about 85°

C. until said copolymer is completely dissolved in said cyanoacrylate composition, such that the adhesive composition formed comprises from about 55 to about 92 percent by weight of said cyanoacrylate ester and about 4 to about 30 percent by weight of said copolymer.

23. A process according to claim 22 wherein there is also dissolved in said cyanoacrylate composition a plasticizer in such an amount that said plasticizer is present in said adhesive composition in an amount of not more than about 25 percent by weight.