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US 9,938,232 B2Granted
LED photoinitiators
AssigneeSun Chemical Corporation
InventorsKai-Uwe W. Gaudl, Juergen Dieker
Life of this patent
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Abstract
Amine derivatives of benzoylbenzoic acid, benzoylbenzoic acid esters and salts were prepared, which are suitable as photo initiators for UV & LED curable compositions. The derivatives are compounds of Formula I, Ia, and II wherein R1, R1a, R2, R3, n and r are as defined herein.
Claims15
A compound of Formula I:
- wherein:
- R1and R1a are each independently selected from the group consisting of tertiary amine, C1-C12 alkoxy, C1-C12 alkyl, C3-C12 cycloalkyl, and C6-C12 aryl radical, each of which is optionally substituted with one or more independently selected oxygen, nitrogen, sulfur, or C1-C12 alkoxy;
- provided that at least one of R1and R1a is a tertiary amine;
- Each R2 is independently selected from the group consisting of hydrogen, a tertiary amine, C1-C12 alkoxy, C1-C12 alkyl, C3-C12 cycloalkyl, and C6-C12 aryl radical, each of which is optionally substituted with one or more independently selected oxygen, nitrogen, sulfur, or C1-C12 alkoxy;
- R3 is selected from the group consisting of a mono-, di-, tri-, tetra-, penta-, hexa-, or polyvalent alkyl or alkoxy radical, optionally substituted with one or more independently selected oxygen, sulfur, nitrogen, OH, carbonyl, (hydroxyl)alkyl, COOH, (carboxy)alkyl, R4, carboxamido, (carboxamido)alkyl, or OCONR5;
- R4 is selected from the group consisting of C3-C12 cycloalkyl, (cycloalkyl)alkyl, C6-C12 aryl, C3-C12 heterocycle, C6-C12 heteroaryl, aralkyl, and alkaryl, each of which is optionally substituted with one or more independently selected OH, (hydroxy)alkyl, C1-C12 alkyl, carboxamido, (carboxamido)alkyl, COOH, or (carboxy)alkyl;
- R5 is selected from the group consisting of H, C1-C12 alkyl, and C1-C12 alkoxy;
- and
- n denotes an integer from 1-100;
- provided that n is less than or equal to the valency of the alkyl or alkoxy radical of R3.
7 more elements
A compound of Formula Ia:
- wherein:
- R1 and R1a are each independently selected from the group consisting of tertiary amine, C1-C12 alkoxy, C1-C12 alkyl, C3-C12 cycloalkyl, and C6-C12 aryl radical, each of which is optionally substituted with one or more independently selected oxygen, nitrogen, sulfur, or C1-C12 alkoxy;
- provided that at least one of R1 and R1a is a tertiary amine;
- Each R2 is independently selected from the group consisting of hydrogen, a tertiary amine, C 1-C12 alkoxy, C1-C12 alkyl, C3-C12 cycloalkyl, and C6-C12 aryl radical, each of which is optionally substituted with one or more independently selected oxygen, nitrogen, sulfur, or C1-C12 alkoxy;
- r denotes an integer from 1-6;
- M is selected from the group consisting of a mono-, di-, tri-, tetra-, penta- or hexavalent metal cation, a protonated tertiary amine, tetraalkyl ammonium group radical, phosphonium, sulfonium, and pyridinium, each of which can be optionally substituted by one or more C1-C12 alkyl radicals.
3 more elements
A method of preparing a UV-curable ink or coating composition comprising adding to the ink or coating composition:
- a) a photoinitiator compound of Formula II:
- wherein:
- R1 and R1a are each independently selected from the group consisting of tertiary amine, C1-C12 alkoxy, C1-C12 alkyl, C3-C12 cycloalkyl, and C6-C12 aryl radical, each of which is optionally substituted with one or more independently selected oxygen, nitrogen, sulfur, or C1-C12 alkoxy;
- provided that at least one of R1 and R1a is a tertiary amine;
- and
- each R2 is independently selected from the group consisting of hydrogen, a tertiary amine, C1-C12 alkoxy, C1-C12 alkyl, C3-C12 cycloalkyl, and C6-C12 aryl radical, each of which is optionally substituted with one or more independently selected oxygen, nitrogen, sulfur, or C1-C12 alkoxy,
- b) at least one acrylate or methacrylate compound;
- and
- c) optionally, a colorant.
6 more elements
Dependencies are inferred from the claim text.