Pressure-sensitive adhesive tape produced from photoactive mixture of acrylic monomers and polynuclear-chromophore-substituted halomethyl-2-triazine

• US 4,329,384 A
• Filed: 02/14/1980
• Issued: 05/11/1982
• Est. Priority Date: 02/14/1980
• Status: Expired due to Term

• Current Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Original Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Inventors: Vesley, George F., Moon, John D.
• Primary Examiner(s): Mc Camish, Marion
• Assistant Examiner(s): Thomas, Alexander S.
• Application Number:
  US06/121,403
• Time in Patent Office: 817 Days
• Field of Search: 544/216, 204/159.23, 430/920, 430/281, 430/283, 430/260, 430/286, 428/40, 428/345, 428/355, 428/352, 428/913, 427/54.1, 427/177, 427/208.4, 427/372.2, 427/331
• US Class Current: 428/41.3
• CPC Class Codes: C08F 2/46 Polymerisation initiated by wave energy or particle radiation
• CPC Class Codes: C08F 2/50 with sensitising agents
• CPC Class Codes: C08F 20/12 of monohydric alcohols or phenols
• CPC Class Codes: C08L 2666/36 Nitrogen-containing compounds
• CPC Class Codes: C09J 133/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C09J 2301/302 the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
• CPC Class Codes: C09J 7/385 Acrylic polymers
• CPC Class Codes: G03F 7/0295 Photolytic halogen compounds
• CPC Class Codes: Y10S 428/913 Material designed to be responsive to temperature, light, moisture
• CPC Class Codes: Y10S 430/121 Nitrogen in heterocyclic ring
• CPC Class Codes: Y10T 428/1452 Polymer derived only from ethylenically unsaturated monomer
• CPC Class Codes: Y10T 428/2809 including irradiated or wave energy treated component
• CPC Class Codes: Y10T 428/2839 with release or antistick coating
• CPC Class Codes: Y10T 428/2891 including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof

Abstract

Pressure-sensitive adhesive tape, the adhesive layer of which is produced from a mixture of (1) a pressure-sensitive adhesive alkyl acrylate polymer and (b) a polynuclear-chromophore-substituted halomethyl-s-triazine such as ##STR1## which has been exposed to ultraviolet radiation to cause the polymer to become crosslinked.

Claims

1. Pressure-sensitive adhesive tape comprising a backing member and at least one adhesive layer produced from a photoactive mixture comprising by weight

(a) 50-100 parts of alkyl acrylate and 0-50 parts of copolymerizable monoethylenically unsaturated monomer and

(b) 0.01 to 2 parts of a polynuclear-chromophore-substituted halomethyl-s-triazine of the formula ##STR8## wherein each of R₁ and R₂ is hydrogen, alkyl, or alkoxy.

2. Pressure-sensitive adhesive tape as defined in claim 1 wherein at least one of R₁ and R₂ is an alkyl or alkoxy group of up to 12 carbon atoms and not more than two alkyl and alkoxy groups have more than 6 carbon atoms.

3. Pressure-sensitive adhesive tape as defined in claim 2 wherein there are two adjacent alkoxy groups interconnected to form a ring.

4. Pressure-sensitive adhesive tape as defined in claim 1 wherein the s-triazine (b) is ##STR9##

5. Pressure-sensitive adhesive tape as defined in claim 1 wherein the s-triazine (b) is ##STR10##

6. Pressure-sensitive adhesive tape as defined in claim 1 wherein (a) comprises (1) 88-99 parts of alkyl acrylate having 4-12 carbon atoms in its alkyl groups or alkyl acrylates having an average of 4-12 carbon atoms in their alkyl groups and (2) correspondingly 12-1) parts of said copolymerizable monomer.

7. Pressure-sensitive adhesive tape as defined in claim 1, the backing member of which is flexible and opaque in order to shield said photoactive mixture from accidental ultraviolet radiation when the tape is wound upon itself into a roll.

8. Pressure-sensitive adhesive tape as defined in claims 1 or 7 wherein at least part of said copolymerizable monomer has highly polar groups.

9. Pressure-sensitive adhesive tape as defined in claim 1, the backing member of which has a low-adhesion layer from which said at least one adhesive layer could be transferred.

10. Pressure-sensitive adhesive tape as defined in claim 9 wherein the copolymerizable monomer having highly polar groups is at least one of acrylic acid, methacrylic acid, itaconic acid, acrylamide, methacrylamide, acrylonitrile, methacrylonitrile, N-substituted acrylamides, hydroxyalkyl acrylates, cyanoethyl acrylate, N-vinylpyrrolidone, and maleic anhydride.

11. Method of making a pressure-sensitive adhesive tape comprising the steps of

(1) mixing by weight

(a) 100 parts of a composition comprising 50-100 parts of alkyl acrylate monomer and 0-50 parts of copolymerizable monoethylenically unsaturated monomer, which composition is polymerizable or has been polymerized to a pressure-sensitive adhesive state and

(b) 0.01 to 2 parts of a polynuclear-chromophore-substituted halomethyl-s-triazine of the formula ##STR11## wherein each of R₁ and R₂ is hydrogen, alkyl or alkoxy, (2) coating the mixture onto a backing member, and

(3) exposing the coated mixture to ultraviolet radiation.

12. Method as defined in claim 11 wherein said composition (a) has been partially polymerized to a coatable viscosity of 300 to 20,000 centipoises at ordinary room temperature, and in step (3) the coated mixture is photopolymerized.

13. Method as defined in either of claim 12 or claim 13 wherein said composition (a) comprises (1) 88-89 parts of alkyl acrylate having 4-12 carbon atoms in its alkyl group or alkyl acrylates having an average of 4-12 carbon atoms in their alkyl groups and (2) correspondingly 12-1 parts of said copolymerizable monomer.

14. Method as defined in claim 13 wherein at least part of said copolymerizable monomer has highly polar groups.

15. Method as defined in claim 11 wherein said composition (a) comprises a polymer, step (2) involves coating onto a flexible backing member a solution of said polymer in an organic solvent, there is an additional step between steps (2) and (3) involving driving off the solvent and in step (3) the polymer becomes crosslinked.

16. Pressure-sensitive adhesive tape produced by the method as defined in claim 11.

17. Method of making a pressure-sensitive adhesive tape comprising the steps of:

(1) mixing by weight

(a) 100 parts of an unpolymerized composition of 50-100 parts of alkyl acrylate and 0-50 parts of copolymerizable monoethylenically unsaturated monomer comprising polar groups, which composition is polymerizable to a pressure-sensitive adhesive state, and,

(b) an addition-polymerization photoinitiator which is activatable by ultraviolet radiation, is not a crosslinking agent, and is dissolved in an amount providing 0.001 to 0.5 percent of the composition (a),

(2) exposing the mixture to ultraviolet radiation to provide a partially-polymerized syrup having a viscosity of 300 to 20,000 centipoises at ordinary room temperature,

(3) mixing with said syrup 0.01 to 2 parts of a polynuclear chromophore-substituted halomethyl-s-triazine of the formula ##STR12## wherein each of R₁ and R₂ is hydrogen, alkyl, or alkoxy, (4) coating said syrup onto a backing member to provide a layer having a thickness of about 25-250 micrometers, and

(5) in an inert atmosphere, irradiating the coating with ultraviolet radiation to further polymerize it to a substantially completely polymerized, crosslinked, pressure-sensitive adhesive state.

18. Method of making a pressure-sensitive adhesive tape as defined in claim 17 wherein said unpolymerized composition comprises (i) 88-99 parts of alkyl acrylate having 4-12 carbon atoms in its alkyl group or alkyl acrylates having an average of 4-12 carbon atoms in their alkyl groups and (ii) correspondingly 12-1 parts of a copolymerizable monomer.

19. Method of making a crosslinkable pressure-sensitive adhesive tape comprising the steps of

(1) mixing by weight

(a) a solution in an organic solvent of a polymer of (i) 88-99 part of alkyl acrylate having 4-12 carbon atoms in its alkyl group or alkyl acrylates having an average of 4-12 carbon atoms in their alkyl groups and (ii) correspondingly 12-1 parts of a copolymerizable monomer and

(b) 0.01 to 2 parts of a polynuclear-chromophore-substituted halomethyl-s-triazine of the formula ##STR13## wherein each of R₁ and R₂ is hydrogen, alkyl, or alkoxy, (2) coating said mixture onto a flexible, opaque backing member to provide a layer having a thickness of about 25-250 micrometers,

(3) driving off the solvent, and

(4) winding the coated backing member on itself into roll form so that the backing member shields the coating from accidental exposure to ultraviolet radiation which would cause the polymer to become crosslinked.