Photoactive mixture of acrylic monomers and chromophore-substituted halomethyl-1-triazine

• US 4,391,687 A
• Filed: 02/16/1982
• Issued: 07/05/1983
• 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.
• Primary Examiner(s): Thomas, Alexander S.
• Application Number:
  US06/348,655
• Time in Patent Office: 504 Days
• Field of Search: 544/216, 204/159.16, 204/159.23, 204/159.18, 525/256, 427/54.1, 430/920, 430/281, 430/283, 430/286, 526/204, 526/220
• US Class Current: 525/330.5
• 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: C09B 69/109 containing other specific dyes
• 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 7/031 Organic compounds not covered by group G03F7/029
• CPC Class Codes: Y10S 430/121 Nitrogen in heterocyclic ring

Abstract

Photopolymerizable mixture of (a) acrylic monomer such as 95 parts of an alkyl acrylate and 5 parts of acrylic acid and (b) 0.01 to 2 parts by weight of a chromophore-substituted-halomethyl-s-triazine such as ##STR1## The novel mixtures are primarily useful as pressure-sensitive adhesive mixtures.

Claims

1. A photoactive mixture comprising by weight

(a) 100 parts of a composition or a polymer of 50-100 parts of acrylic monomer and 0-50 parts of copolymerizable monoethylenically unsaturated monomer and

(b) 0.01 to 2 parts of a chromophore-substituted halomethyl-s-triazine of the formula ##STR13## wherein R₁, R₂, R₃, and R₄ are independently hydrogen or alkoxy groups, and 1 to 3 of R₁, R₂, R₃, and R₄ are hydrogen.

2. A photoactive mixture as defined in claim 1 wherein said alkoxy groups have at most 12 carbon atoms.

3. A photoactive mixture as defined in claim 2 wherein at least two of said groups are alkoxy.

4. A photoactive mixture as defined in claim 3 wherein two adjacent alkoxy groups are interconnected to form a ring.

5. A photoactive mixture as defined in claims 1 or 2 wherein said composition or polymer (a) is a composition which is partially polymerized and has a coatable viscosity of 300 to 20,000 centipoises at ordinary room temperature.

6. The product of photopolymerizing the partially photopolymerized composition as defined in claim 5 to about 100% conversion of the unsaturated moiety.

7. A photoactive mixture as defined in claims 1 or 2 wherein said composition or polymer (a) is a polymer of an alkyl acrylate.

8. A solution of a photoactive mixture as defined in claim 7 in organic solvent.

9. A photoactive mixture as defined in claim 1 wherein the s-triazine (b) is selected from the group consisting of ##STR14## wherein n is 1, 2 or 3.

10. A photoactive mixture as defined in claim 1 wherein the composition or polymer (a) comprises a composition or partially polymerized composition of (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 and is polymerizable to a pressure-sensitive adhesive state.

11. A photoactive mixture as defined in claims 1 or 10 wherein at least part of said copolymerizable monomer has highly polar groups.

12. A photoactive mixture as defined in claim 11 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.