Radiation-curable mixture containing low-molecular, ethylenically unsaturated compounds having non-aromatic ring systems

Patent metadata

Field	Value
Publication number	US-9725549-B2
Application number	US-44167007-A
Country	US
Kind code	B2
Filing date	Oct 29, 2007
Priority date	Oct 27, 2006
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

A mixture having (A) a polymer obtain by polymerizing at least one free-radically polymerizable compound; and (B) at least one compound having at least one ethylenically unsaturated, free-radically polymerizable group and having a weight-average molecular weight Mw of less than 5000 g/mol, wherein at least 10% by weight of compounds (B) are one or more compounds B1 with at least one nonaromatic ring system.

First claim

The invention claimed is:

1. A self-adhesive article, selected from the group consisting of a self-adhesive label, a self-adhesive assembly tape, and a self-adhesive protective film, comprising a pressure-sensitive adhesive mixture, comprising:
(A) an acrylate polymer obtained by polymerizing a polymerizable compound comprising at least 80% by weight of a C 1 -C 20 alkyl (meth)acrylate, wherein a photoinitiator is attached to the polymer; and
(B) a compound comprising an ethylenically unsaturated, free-radically polymerizable group and having a weight-average molecular weight Mw of less than 5000 g/mol,
wherein
at least 10% by weight of compound (B) is at least one compound (B1) comprising at least one nonaromatic ring system selected from the group consisting of an isocyanurate ring, and a ring system of the formula

compound B1 has 2 to 3 acrylate groups;
the self-adhesive article can be pulled off from a protected article without residue, and
the pressure-sensitive adhesive mixture is crosslinked with high energy radiation with UV light or an electron beam,
and wherein the self-adhesive article has a peel strength of at least 22.6 N/25 mm.

2. The article of claim 1 , wherein the polymer (A) has a K value of 10 to 100 measured in a 1% strength by weight solution of tetrahydrofuran, at 21° C.

3. The article of claim 1 , wherein the polymer (A) is a solution polymer.

4. The article of claim 1 , wherein the nonaromatic ring system comprises

5. The article of claim 1 , wherein the nonaromatic ring system of the compound (B1) is the isocyanurate ring system.

6. The article of claim 1 , wherein at least 50% by weight of the compound (B) is compound (B1).

7. The article of claim 1 , wherein the compound (B1) consists of at least 10% by weight, based on molar mass, of carbon or nitrogen atoms which are part of the ring system.

8. The article of claim 1 , wherein the compound (B) comprises on average 1 to 5 polymerizable groups per molecule.

9. The article of claim 1 , wherein at least one polymerizable group of the compound (B) is an acrylic group.

10. The article of claim 1 , wherein a weight fraction of the compound (B) is 5% to 70% by weight, based on a sum by weight of the polymer (A) and the compound (B).

11. The article of claim 1 , further comprising 0.0001 to 0.5 mol of the photoinitiator or of a molecule group which is active as the photoinitiator and is attached to the polymer, per 100 g of a sum by weight of the polymer (A) and the compound (B).

12. The article of claim 1 , wherein the mixture comprises less than 5 parts by weight of water or solvent, based on 100 parts by weight of a sum by weight of the polymer (A) and compound (B).

13. The article of claim 1 , wherein at least 80% by weight of the compound (B) is compound (B1).

14. The article of claim 1 , wherein 100% by weight of the compound (B) is compound (B1).

15. The article of claim 1 , wherein at least one polymerizable group of the compound (B) is a methacrylic group.

16. The article of claim 1 , wherein all polymerizable groups of the compound (B) are methacrylic groups.

17. The article of claim 1 , wherein all polymerizable groups of the compound (B) are acrylic groups.

18. The article of claim 1 , wherein the compound B) is liquid at 21° C. and 1 bar.

19. The article of claim 1 , wherein
the photoinitiator is attached to the polymer in amounts of 0.0001 to 0.5 mol of a photoinitiator group per 100 g of a sum by weight of the polymer (A) and the compound (B); and
the weight amount of polymer (A) is from 95% to 70% by weight based on the sum by weight of (A) and (B) and the weight amount of compound (B) is from 5% to 30% by weight based on the sum by weight of (A) and (B).

20. The article of claim 1 , wherein the self-adhesive article has a peel strength of from 22.6 to 27.0 N/25 mm.

21. The article of claim 1 , wherein the pressure-sensitive adhesive mixture comprises:
70 to 95% by weight of the acrylate polymer (A), based on the sum by weight of (A) and (B), comprising at least 80% by weight of n-butylacrylate, wherein the photoinitiator is attached to the polymer in amounts of 0.0002 to 0.01 mol of a photoinitiator group per 100 g of a sum by weight of the polymer (A) and the compound (B); and
5 to 30% by weight of the compound (B), based on the sum by weight of (A) and (B).

22. The article of claim 20 , wherein the pressure-sensitive adhesive mixture comprises:
70 to 95% by weight of the acrylate polymer (A), based on the sum by weight of (A) and (B), comprising at least 80% by weight of n-butylacrylate, wherein the photoinitiator is attached to the polymer in amounts of 0.0002 to 0.01 mol of a photoinitiator group per 100 g of a sum by weight of the polymer (A) and the compound (B); and
5 to 30% by weight of the compound (B), based on the sum by weight of (A) and (B).

23. A method of producing the article of claim 1 , the method comprising:
applying the mixture to a backing; and
exposing the mixture to high-energy radiation.

Assignees

• Licht Ulrike
• Wulff Dirk
• Duesterwald Uwe
• Basf Se

Inventors

• Licht Ulrike
• Wulff Dirk
• Duesterwald Uwe

Classifications

• C09J7/0217

  Chemistry & Metallurgy · mapped topic

• C08F290/061

  Polyesters; Polycarbonates · CPC title

• C09J2433/00

  Presence of (meth)acrylic polymer · CPC title

• C08F265/04

  on to polymers of esters · CPC title

• Y10T428/2852

  Adhesive compositions · CPC title