Radiation curable polyolefin pressure sensitive adhesive

• US 5,209,971 A
• Filed: 02/03/1992
• Issued: 05/11/1993
• Est. Priority Date: 09/06/1989
• Status: Expired due to Term

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Overstreet, Thomas S., Christopher, Susan S., Copley, Bruce C., Babu, Gaddam N.
• Primary Examiner(s): Herbert, Jr., Thomas J.
• Application Number:
  US07/829,968
• Time in Patent Office: 463 Days
• Field of Search: 428/457, 428/461, 428/462, 428/261, 428/343, 428/344, 428/345, 428/352, 428/355, 524/274, 525/210, 525/73, 525/332.1, 526/350, 526/336, 526/139, 522/111, 522/120, 522/183
• US Class Current: 428/343
• CPC Class Codes: C09J 123/18 Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
• CPC Class Codes: C09J 7/381 based on macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
• 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 428/2804 Next to metal
• 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 428/2878 including addition polymer from unsaturated monomer
• CPC Class Codes: Y10T 428/2883 including addition polymer of diene monomer [e.g., SBR, SIS, etc.]
• CPC Class Codes: Y10T 428/31692 Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31696 Including polyene monomers [e.g., butadiene, etc.]

Abstract

Pressure sensitive adhesive compositions comprise one or more poly(alpha-olefin) homopolymers, copolymers, terpolymers, and tetrapolymers derived from monomers containing 6 to 10 carbon atoms and photoactive crosslinking agents wherein radiation curing provides adhesive films having a superior balance of peel and shear adhesive properties and the pressure sensitive adhesive is useful in pressure sensitive adhesive tapes, in articles containing transfer adhesive films, and as the bonding material between supports in a laminated structure.

Claims

1. An article comprising an ultraviolet radiation curable poly(α

-olefin) adhesive composition coated on a substrate, said composition comprising;

a) at least one polymer comprising the reaction product of from 85 to 100 mole percent C₆ to C₁₀ α

-olefin and 15 to 0 mole percent of one or more polyene monomer; and

b) an effective amount of an ultraviolet radiation activatable crosslinking agent.

2. The article according to claim 1 wherein said adhesive composition on a substrate has been cured by ultraviolet radiation.

3. The article according to claim 1 wherein said substrate is selected from the group consisting of polymer films, woven and non-woven fabrics, metals, paper, glass, and composite materials comprising laminates of at least two of said substrates.

4. The article according to claim 1 which further comprises a release liner.

5. The article according to claim 1 wherein said radiation curable poly (α

-olefin) pressure-sensitive adhesive composition comprises;

a) a crosslinkable polymer comprising random or block units with the formulae;

##STR4## where R₁ is selected from monovalent hydrocarbon groups containing 4 to 8 carbon atoms;

R₂ is a monovalent hydrocarbon radical containing one or more ethylenically unsaturated groups selected from the groups consisting of;

space="preserve" listing-type="equation">--CH.sub.2).sub.n R.sub.3, --Ar--R.sub.3, --CH.sub.2).sub.n Q--R.sub.3

n=an integer 0 to 14;

R₃ is a C₂ to C₁₀ monovalent hydrocarbon group containing one or more ethylenically unsaturated groups;

Ar is a divalent aromatic radical containing 1 or 2 aromatic rings with from 0-8 substituents selected from the group consisting of alkyl, aryl, cycloalkyl, alkoxy, and aryloxy containing from 1-12 carbon atoms;

Q is a divalent radical selected from the group consisting of ##STR5## where R₄ and R₅ are the same or different C₁ to C1₀ monovalent hydrocarbon radicals selected from the group consisting of alkyl, cycloalkyl, alkaryl, aryl, alkoxy, aryloxy;

x is the mole percent of one or more C₆ -C₁₀ α

-olefin monomer(s) the total ranging from 85-100 mole percent;

y is the mole percent of one or more polyene monomer(s) the total ranging from 0-15 mole percent;

with the proviso that x+y=100 mole percent;

b) an effective amount of one or more photoactive-crosslinking-agents sufficient to crosslink the pressure-sensitive adhesive composition upon irradiation from a source of article radiation.

6. The article according to claim 1 wherein said polymer in said radiation curable poly(α

-olefin) pressure-sensitive adhesive composition is selected from the group consisting of a homopolymer, a copolymer, a terpolymer, and a tetrapolymer containing at least two polyene monomers.

7. The article according to claim 1 wherein the polyene monomers in said radiation curable pressure-sensitive adhesive composition are selected from the group consisting of aliphatic dienes, aliphatic trienes, aliphatic tetraenes, aromatic dienes, aromatic trienes, monocyclic dienes, bicyclic dienes, tricyclic dienes, tetracyclic dienes, monocyclic trienes bicyclic trienes, tricyclic trienes, and tetracyclic trienes.

8. The article according to claim 1 wherein said polymer in said radiation curable poly(α

-olefin) pressure-sensitive adhesive composition comprises residual ethylenically unsaturated groups in pendant side chains.

9. The article according to claim 1 wherein said polymer in said radiation curable poly(α

-olefin) pressure-sensitive adhesive composition comprises residual ethylenically unsaturated groups in the backbone.

10. The article according to claim 1 wherein said polymer of said radiation curable poly(α

-olefin) pressure-sensitive adhesive composition has a gel content in the range of 2 to 95 weight percent.

11. The article according to claim 1 wherein said radiation activatable crosslinking agent in said radiation curable poly(α

-olefin) pressure-sensitive adhesive composition is selected from the group consisting of aldehydes, ketones, quinones, thioxanthones, and s-traizines.

12. The article according to claim 1 wherein said radiation curable poly(α

-olefin) pressure-sensitive adhesive composition further comprises a tackifying resin in an amount in the range of more than 0 to 150 parts per hundred parts of the adhesive composition.

13. The article according to claim 1 wherein said radiation curable poly(α

-olefin) pressure-sensitive adhesive composition further comprises a chemically effective amount of at least one additive selected from the group consisting of pigments, dyes, fillers, plasticizers, stabilizers, antioxidants, and processing oils.

14. The article according to claim 1 further comprising a primary layer for said adhesive.

15. The article according to claim 14 wherein said primer layer comprises a triblock copolymer of styrene-ethylene/butylene-styrene grafted with maleic anhydride optionally in combination with amorphous polypropylene.

16. The article according to claim 1 wherein said adhesive composition on a substrate has been cured.

17. The article according to claim 16 which is a pressure-sensitive adhesive tape.

18. The article according to claim 16 which is a transfer adhesive film.

19. The article according to claim 1 wherein said substrate further comprises a release layer on said substrate to provide an adhesive transfer film.

20. The cured article according to claim 19.

21. A laminate structure comprising at least two substrates, and coated therebetween a layer of ultraviolet radiation curable poly(α

-olefin) pressuresensitive adhesive composition comprising;

a) at least one polymer comprising the reaction product of from 85 to 100 mole percent C₆ to C₁₀ α

-olefin and 15 to 0 mole percent of one or more polyene monomer;

b) an effective amount of an ultraviolet radiation activatable crosslinking agent, at least one of said substrates being capable of transmitting actinic or electron beam radiation.

22. The laminated structure according to claim 21 wherein said adhesive layer has been cured.