Adhesive detackification

• US 20050054785A1
• Filed: 09/05/2003
• Published: 03/10/2005
• Est. Priority Date: 05/08/2001
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Stebbings, William L., Landgrebe, Kevin D., Perry, Dale C.
• Granted Patent: US 7,258,917 B2
• Time in Patent Office: Days
• US Class Current: 525/379
• CPC Class Codes: C08F 2/46 Polymerisation initiated by wave energy or particle radiation
• CPC Class Codes: C08F 2/48 by ultraviolet or visible light
• CPC Class Codes: C08F 220/12 of monohydric alcohols or phenols
• CPC Class Codes: C08F 222/103 of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C09D 4/00 Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• 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
• CPC Class Codes: Y10T 428/24802 Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
• CPC Class Codes: Y10T 428/28 Web or sheet containing structurally defined element or component and having an adhesive outermost layer
• CPC Class Codes: Y10T 428/2809 including irradiated or wave energy treated component
• CPC Class Codes: Y10T 428/2839 with release or antistick coating

Abstract

The invention describes a method of curing a polymerizable material containing ethylenically unsaturated bonds at a temperature of 60° C. or less, comprising the steps of (a) providing a curative comprising an effective amount of a light-stable isomer of a 2,4,5-triarylimidazolyl dimer, such as bilophine; (b) activating said curative by application of an activator selected from the group consisting of solvent and friction; and (c) combining the activated curative with the polymerizable material. Articles comprising an adhesive having a detackified surface, such as adhesive bandages, a detackifying solution, a two-part adhesive system, and a fastening system are also provided.

Claims

1. A method of curing a polymerizable material containing ethylenically unsaturated bonds at a temperature of 60°

C. or less, comprising the steps of;

a) providing a curative comprising an effective amount of a light-stable isomer of a 2,4,5-triarylimidazolyl dimer;

b) activating said curative by application of an activator selected from the group consisting of solvent and friction; and

c) combining the activated curative with the polymerizable material.

2. The method of claim 1 wherein said 2,4,5-triarylimidazolyl dimer is a light-stable isomer of bilophine.

3. The method of claim 2 wherein said light-stable isomer of bilophine is 4-4′

bilophine.

4. The method of claim 1 wherein said curative additionally comprises an amine.

5. The method of claim 4 wherein step c) is performed in the presence of air or oxygen.

6. The method of claim 1 wherein said curative additionally comprises a secondary or tertiary amine.

7. The method of claim 1 wherein said curative additionally comprises a tertiary amine.

8. The method of claim 7 wherein said tertiary amine is N-methyl diethanolamine.

9. The method of claim 1 wherein said activator is solvent.

10. The method of claim 9 wherein said solvent is a liquid at the reaction temperature.

11. The method of claim 10 wherein said solvent is a reactive solvent selected from the group consisting of methyl acrylate, methyl methacrylate, ethyl acrylate, isopropyl methacrylate, n-hexyl acrylate, stearyl acrylate, allyl acrylate, glycerol diacrylate, glycerol triacrylate, ethyleneglycol diacrylate, diethyleneglycol diacrylate, triethyleneglycol dimethacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, trimethylolpropane triacrylate, 1,2,4-butanetriol trimethacrylate, 1,4-cyclohexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, vinyl compounds, and mixtures thereof.

12. The method of claim 10 wherein said solvent is a non-reactive solvent selected from the group consisting of toluene, xylene, cumene, mesitylene, phenyl acetate, methyl benzoate, benzyl acetate, ethyl benzoate, ethyl acetate, benzyl alcohol, butanol, and propanol.

13. The method of claim 9 wherein said solvent comprises said polymerizable material.

14. The method of claim 1 wherein said activator is friction.

15. A method of detackifying an adhesive comprising the method of curing of claim 1.

16. An article comprising an adhesive having a surface that is detackified according to the method of claim 15.

17. An article comprising an adhesive having a detackified surface, wherein said surface contains a reaction product of 2,4,5-triarylimidazolyl radicals.

18. The article according to claim 17 wherein said reaction product of 2,4,5-triarylimidazolyl radicals is a 2,4,5-triarylimidazole.

19. The article according to claim 17 wherein said reaction product of 2,4,5-triarylimidazole radicals comprises a 2,4,5-triarylimidazolyl moiety.

20. The article of claim 17 wherein the detackified surface has a tack level below about 5 g.

21. The article of claim 17 additionally comprising a non-detackified surface that is essentially free of bilophine.

22. The article of claim 17 wherein the adhesive is at least partially transparent.

23. The article of claim 17 wherein the adhesive is removable from a substrate to which the adhesive is adhered by stretching the adhesive to at least about 150% of its initial length at an angle below about 35°

from the substrate.

24. The article according to claim 17 wherein the detackified surface is selected from the group consisting of:

an exposed portion of an adhesive bond line, an edge of an adhesive sheet, an edge of an adhesive tape strip, an edge of an adhesive tape roll, an outer surface of a glue stick, an outer surface of a bulk adhesive mass, a back surface of a unitape, and a back surface of an adhesive strip in an adhesive bandage.

25. The article of claim 24 being an adhesive strip in an adhesive bandage, wherein the detackified surface comprises an integral backing to the adhesive strip.

26. A bandage comprising the adhesive strip of claim 25 further comprising an absorbent pad.

27. A method of making an article comprising an adhesive having a detackified surface comprising the step of applying a curative to an adhesive surface of an article comprising an adhesive, said curative comprising a component selected from the group consisting of 2,4,5-triarylimidazole, bilophine and lophine radicals.

28. An article made according to the method of claim 27.

29. A detackifying solution comprising a light-stable bilophine;

a secondary or tertiary amine; and

a suitable solvent.

30. The detackifying solution of claim 29 wherein the solvent comprises a reactive diluent.

31. The detackifying solution of claim 30 wherein the reactive diluent is selected from the group consisting of methyl acrylate, methyl methacrylate, ethyl acrylate, isopropyl methacrylate, n-hexyl acrylate, stearyl acrylate, allyl acrylate, glycerol diacrylate, glycerol triacrylate, ethyleneglycol diacrylate, diethyleneglycol diacrylate, triethyleneglycol dimethacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, trimethylolpropane triacrylate, 1,2,4-butanetriol trimethacrylate, 1,4-cyclohexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, vinyl compounds, and mixtures thereof

32. A two-part adhesive comprising a first part which comprises a light-stable isomer of a 2,4,5-triarylimidazolyl dimer and a second part which comprises a secondary or tertiary amine and a polymerizable material containing ethylenically unsaturated bonds.

33. The adhesive of claim 32 wherein said second part further comprises a solvent.

34. An activated adhesive system comprising a combination of the first part of the two-part adhesive of claim 32 and the second part of the two-part adhesive of claim 32.

35. A set adhesive system comprising the reaction product of the first part of the two-part adhesive of claim 32 and the second part of the two-part adhesive of claim 32.

36. The adhesive system of claim 35 which is removable from a substrate to which the adhesive is adhered by stretching the adhesive to at least about 150% of its initial length at an angle below about 35°

from the substrate.

37. The adhesive system of claim 35 wherein the cured combination is rigid.

38. A fastening system comprising i) a first element having a first surface bearing thereon the first part of the composition of claim 32;

and

ii) a second element having a surface corresponding to and frictionally coupling with the first surface of the first element, which second element surface bears thereon the second part of the composition of claim 32;

wherein the first element and the second element are more securely fastened together relative to two such elements absent the composition of claim 32.

39. The fastening system of claim 38 wherein the first element and the second element are permanently joined by the composition of claim 32.

40. The fastening system of claim 38 wherein

the first element is selected from a nut, a threaded region, a first sheet, and a first section of a telescoping pipe;

and wherein

the second element is correspondingly selected from a bolt, an opposing threaded region such that the two regions threadably connect, a second sheet, and a section of a telescoping pipe corresponding to said first section.

41. The fastening system of claim 40 wherein said first and second sheets are selected from papers, films, polymers, metals, and ceramics.