Aziridine-functional photoactive crosslinking compounds
Assignee3M Innovative Properties Company
InventorsPeiwang Zhu, Maureen A. Kavanagh, Kelly S. Anderson, Larry R. Krepski, Guy D. Joly, Belma Erdogan, Babu N. Gaddam
Life of this patent
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Abstract
A photoactive compound that is the Michael addition reaction product of an aziridine compound and a photoinitiator-functional (meth)acrylate is described. The compound can be used to crosslink (meth)acrylic polymers via a hydrogen abstracting or an alpha-cleavage mechanism.
Claims26
A photoactive crosslinking compound having the general formula:
- wherein R1 is H or a C1 to C4 alkyl group;
- o is 0 to 2;
- X1 and X2 are each independently —O— or —NH—;
- R2 is a divalent alkylene of 2 to 10 carbon atoms or —(R3)2C(CH2)m(CO)OR9—, where m is 0 or 1, R3 is H or a C1 to C4 alkyl group, and R9 is a C2-C6 alkylene;
- n is 0 or 1,
- R7 is H or CH3;
- and
- Z is a photoinitiator group.
A crosslinkable composition comprising an acid-functional (meth)acrylate copolymer and a photoactive crosslinking compound of the formula:
- wherein R1 is H or a C1 to C4 alkyl group;
- o is 0 to 2;
- X1 and X2 are each independently —O— or —NH—;
- R2 is a divalent alkylene of 2 to 10 carbon atoms or —(R3)2C(CH2)m(CO)OR9—, where m is 0 or 1, R3 is H or a C1 to C4 alkyl group, and R9 is a C2-C6 alkylene;
- n is 0 or 1,
- R7 is H or CH3;
- and
- Z is a photoinitiator group.
A method of preparing a pressure sensitive adhesive comprising combining;
- (a) a copolymer comprising
- i. 85 to 99 parts by weight of an (meth)acrylic acid ester of non-tertiary alcohol;
- ii. 1 to 15 parts by weight of an acid functional monomer;
- iii. 0 to 10 parts by weight of a second, non-acid functional, polar monomer;
- iv. 0 to 5 parts vinyl monomer, with
- (b) a photoactive crosslinking compound of the formula:
- wherein R1 is H or a C1 to C4 alkyl group;
- o is 0 to 2;
- X1 and X2 are each independently —O— or —NH—;
- R2 is a divalent alkylene of 2 to 10 carbon atoms or —(R3)2C(CH2)m(CO)OR9—, where m is 0 or 1, R3 is H or a C1 to C4 alkyl group, and R9 is a C2-C6 alkylene;
- n is 0 or 1,
- R7 is H or CH3;
- and
- Z is a photoinitiator group;
- and
- (c) heating the mixture, and
- (d) exposing to UV to effect photocrosslinking.
Syrup polymer composition comprising:
- a) first component solute polymer comprising:
- i. 85 to 99 parts by weight of an (meth)acrylic acid ester of non-tertiary alcohol;
- ii. 1 to 15 parts by weight of an acid functional monomer;
- iii. 0 to 10 parts by weight of a second, non-acid functional, polar monomer;
- iv. 0 to 5 parts vinyl monomer, and
- b) a second component comprising at least one free-radically polymerizable solvent monomer, and
- an aziridine crosslinking compound of the formula:
- wherein R1 is H or a C1 to C4 alkyl group;
- o is 0 to 2;
- X1 and X2 are each independently —O— or —NH—;
- R2 is a divalent alkylene of 2 to 10 carbon atoms or —(R3)2C(CH2)m(CO)OR9—, where m is 0 or 1, R3 is H or a C1 to C4 alkyl group, and R9 is a C2-C6 alkylene;
- n is 0 or 1,
- R7 is H or CH3;
- and
- Z is a photoinitiator group.
Dependencies are inferred from the claim text.