US 6,284,813 B1Granted

Alkylphenylbisacylphosphine oxides and photoinitiator mixtures

AssigneeCiba Specialty Chemicals Corporation

InventorsDavid George Leppard, Manfred Köhler, Andreas Valet

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Abstract

Compounds of the formula I in which R1 is C1-C4alkyl, R2 is hydrogen, C1-C4alkyl or C1-C4alkoxy and R3, R3, R4, R5, R6, and R7 independently of one another are hydrogen, halogen, C1-C20alkyl, cyclopentyl, cyclohexyl, C2-C12alkenyl, C2-C18 alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C1-C4alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C1-C4alkyl and/or C1-C4alkoxy, with the provisos that at least one of the radicals R3, R4, R5, R6 and R7 is other than hydrogen and that, if R1 and R2 are methyl, R3 and R6 are not methyl, and mixtures of such compounds with α-hydroxy ketones, benzophenones and α-amino ketones, are suitable as photoinitiators.

Claims4

Dependent claims

A photoinitiator mixture consisting essentially of at least one compound of formula Ia and two compounds of formula II

in which
R1 is C1-C4alkyl;
R2 is hydrogen, C1-C4alkyl or C1-C4alkoxy, and
R3, R4, R5, R6 and R7 independently of one another are hydrogen, halogen, C1-C20alkyl, cyclopentyl, cyclohexyl, C2-C12alkenyl, C2-C18alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C1-C4alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C1-C4alkyl and/or C1-C4alkoxy;
in which
R8 is hydrogen, C1-C18alkyl, C1-C18 alkoxy, —OCH2CH2—OR12, a group
or a group
in which I is a number from 2 to 10 and A is a radical
R9 and R10 independently of one another are hydrogen, C1-C6 alkyl, phenyl, C1-C18- alkoxy, OSiR13R14R14a or —O(CH2CH2O)q—C1-C16alkyl, in which q is a number from 1 to 20, or
R9 and R10, together with the carbon atom to which they are attached, form a cyclohexyl ring;
R11 is hydroxyl, C1-C16alkoxy or —O(CH2CH2O)q—C1-C16alkyl;
where R9, R10 and R11, are not all simultaneously C1-C16alkoxy or —O(CH2CH2O)q—C1-C16alkyl,
R12 is hydrogen, C1-C8alkyl,
R13 R14a and R14 independently of one another are C1-C4alkyl or phenyl.

11 more elements

A photoinitiator mixture consisting essentially of

5% bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 95% 1-benzoyl-1-hydroxy-1-methylethane;
or
5% bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 95% 1-benzoylcyclohexanol;
or
25% bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 75% 2,2-dimethoxy-1.2-diphenylethan-1-one;
or
5% bis(2,4,6trimethylbenzoyl)phenylphosphine oxide and 95% 2,2-dimethoxy-1,2-diphenylethan1-one;
or
25% bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 75% 4-(2hydroxyethoxy)benzoyl-1-hydroxy-1-methylethane;
or
5% bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and 95% 4-(2-hydroxyethoxy)benzoyl-1-hydroxy-1-methylethane;
or
5% bis(2,4,6-trimethylbenzoyl)-2,5-diisopropylphenylphosphine oxide and 95% 1-benzoylcyclohexanol;
or
5% bis(2,4,6-trimethylbenzoyl)-2,5-diisopropylphenylphosphine oxide and 95% 1-benzoyl-1-hydroxy-1-methylethane;
or
25% bis(2,4,6-trimethylbenzoyl)-2,5-diisopropylphenylphosphine oxide and 75% 1-benzoylcyclohexanol;
or
25% bis(2,4,6-trimethylbenzoyl)-2.5-diisopropylphenylphosphine oxide and 75% 1-benzoyl-1-hydroxy-1-mothylethane, or
5% bis(2,4,6-trimethylbenzoyl)-4-tert-butyl2,6-dimethylphenylphosphine oxide and 95% 1-benzoylcyclohexanol;
or
5% bis(2,4,6-trimethylbenzoyl)4-tert-butyl-2,6-dimethylphenylphosphine oxide and 95% 1-benzoyl-1-hydroxy-1-methylethane;
or
25% bis(2,4,6-trimethylbenzoyl)-4-tert-butyl-2,6-dimethylphenylphosphine oxide and 75% 1-benzoylcyclohexanol;
or
25% bis(2,4,6-trimethylbenzoyl)-4-tert-butyl-2,6-dimethylphenylphosphine oxide and 75% 1-benzoyl-1-hydroxy-1-methylethane;
or
5% bis(2,6-dimethylbenzoyl)phenylphosphine oxide and 95% 1-benzoyl-1-hydroxy-1-methylethane:
or
5% bis(2,6-dimethylbenzoyl)phenylphosphine oxide and 95% 1-benzoylcyclohexanol;
or
25% bis(2,6-dimethylbenzoyl)phenylphosphine oxide and 76% 1-benzoyl-1-hydroxy-1-methylethane;
or
25% bis(2,6-dimethylbenzoyl)phenylphosphine oxide and 75% 1-benzoylcyclohexanol;
or
5% bis(2,4,6-trimethylbenzoyl)2,M5imethylphenylphosphine oxide and 95% 1-benzoylcyclohexanol;
or
5% bis(2,4,6-trimethylbenzoyl)-2,5-dimethylphenyl-phosphine oxide and 95% 1-benzoyl-1-hydroxy-1-methylethane;
or
25% bis(2,4,6-tnrmethylbenzoyl)-2,5imethylphenylphosphine oxide and 75% 1-benzoylcyclohexanol;
or
25% bis(2,4,6-trimethylbenzoyl)-2,5dimethylphenylphosphine oxide and 75% 1-benzoyl-1-hydroxy-1-methylethane;
or
25% bis(2,4,6-trimethylbenzoyl)2,5-dimethylphenylphosphine oxide and 75% 2,2-dimethoxy-1,2-diphenylethan-1-one;
or
25% bis(2,4,6-trimethylbenzoyl2,5-dimethylphenylphosphinoxide and 75% 4-(2-hydroxyethoxy)benzoyl-1-hydroxy-1-methylethane.

43 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/009,827Filed 20 Jan 1998 · division
Priority: CH 558/964 Mar 1996
Granted: 4 Sep 2001
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

G03F 7/029
With photosensitivity-increasing substances, e.g. photoinitiators: inorganic compounds; Onium compounds; Organic compounds having hetero atoms…
C07F 9/5337
Organo-phosphine oxides; Organo-phosphine thioxides: phosphine oxides or thioxides containing the structure -C-P or NC-P
C08F 2/50
By ultraviolet or visible light: with sensitising agents
C09D 4/00
Coating compositions