Photoinitiator formulations

Details Photoinitiator formulations Photoinitiator formulations

2002-03-18

2004-10-12

Seidleck, James J. (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Compositions to be polymerized by wave energy wherein said...

C522S084000, C522S038000, C522S086000, C522S087000, C522S088000, C522S101000, C522S102000, C522S104000, C522S108000, C522S150000, C522S153000, C522S178000, C522S182000, C502S005000, C502S164000, C502S162000, C502S155000, C502S152000

Reexamination Certificate

active

06803392

ABSTRACT:

The present application relates to aqueous suspensions of photoinitiators and to the preparation and use thereof.
It is known in the art to add additives in dispersed form, that is to say in the form of emulsions or suspensions, to polymerisable formulations, especially in order to facilitate incorporation of the additives into those formulations. The additives are for that purpose usually homogeneously dissolved in one phase or melted with one another and then dispersed in water. For example, in U.S. Pat. No. 5,196,142 and U.S. Pat. No. 5,116,534 aqueous emulsions of antioxidants are described and in U.S. Pat. No. 5,549,847 aqueous dispersions of corrosion inhibitors are disclosed. Published in U.S. Pat. No. 4,965,294 and U.S. Pat. No. 5,168,087 are aqueous emulsions of photoinitiators, especially hydroxyketones.
There is a need in the art for effective, stable photoinitiators that can readily be incorporated.
The invention relates to aqueous, storage-stable, non-sedimenting suspensions comprising
(a) at least one mono- or bis-acylphosphine oxide of formula I
 wherein
R
1
is C
1
-C
20
alkyl; C
2
-C
20
alkyl interrupted by one or more O atoms; C
1
-C
12
alkoxy; phenyl-C
1
-C
4
alkyl; or phenyl that is unsubstituted or substituted by C
1
-C
20
alkyl, C
1
-C
12
alkoxy, halogen, cyclopentyl, cyclohexyl, C
2
-C
12
alkenyl, C
2
-C
18
alkyl interrupted by one or more O atoms, and/or by phenyl-C
1
-C
4
alkyl; or R
1
is biphenylyl;
R
2
is the radical
 or has one of the meanings given for R
1
;
R
3
and R
4
are each independently of the other C
1
-C
12
alkyl, C
1
-C
12
alkoxy or halogen; and
R
5
is hydrogen, C
1
-C
12
alkyl, C
1
-C
12
alkoxy or halogen;
(b) at least one dispersant;
(c) water; and, optionally,
(d) further additives.
C
1
-C
20
Alkyl is linear or branched and is, for example, C
1
-C
12
-, C
1
-C
8
-, C
1
-C
8
- or C
1
-C
4
-alkyl. Examples are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, ten-butyl, pentyl, hexyl, heptyl, 2,4,4-trimethylpentyl, 2-ethylhexyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl. For example, R
1
is C
1
-C
12
alkyl, especially C
1
-C
8
alkyl, preferably branched octyl, for example 2,4,4-trimethylpentyl.
R
3
, R
4
and R
5
are, for example, C
1
-C
8
alkyl, especially C
1
-C
4
alkyl. Butyl and, especially, methyl are preferred.
C
1
-C
12
Alkyl, C
1
-C
8
alkyl and C
1
-C
4
alkyl are likewise linear or branched and have, for example, the meanings given above up to the corresponding number of carbon atoms.
C
2
-C
20
Alkyl interrupted one or more times by —O— is interrupted, for example, from 1 to 9 times, e.g. from 1 to 7 times or once or twice, by —O—. If the radicals are interrupted by more than one —O—, then the O atoms are each separated from the other(s) by at least one methylene group, yielding, for example, structural units such as —CH
2
—O—CH
3
, —CH
2
CH
2
—O—CH
2
CH
3
, —[CH
2
CH
2
O]
y
—CH
3
, wherein y=1-9, —(CH
2
CH
2
O)
7
CH
2
CH
3
, —CH
2
—CH(CH
3
)—O—CH
2
—CH
2
CH
3
or —CH
2
—CH(CH
3
)—O—CH
2
—CH
3
.
C
2
-C
18
Alkyl interrupted by one or more O atoms is as defined above up to the corresponding number of carbon atoms.
C
1
-C
12
Alkoxy is a linear or branched radical and is, for example, C
1
-C
8
-, C
1
-C
6
- or C
1
-C
4
-alkoxy. Examples are methoxy, ethoxy, propoxy, isopropoxy, n-butyloxy, sec-butyloxy, isobutyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, 2,4,4-trimethylpentyloxy, 2-ethyl-hexyloxy, octyloxy, nonyloxy, decyloxy and dodecyloxy, especially methoxy, ethoxy, propoxy, isopropoxy, n-butyloxy, sec-butyloxy, isobutyloxy and tert-butyloxy, preferably methoxy. C
1
-C
8
Alkoxy, C
1
-C
6
alkoxy and C
1
-C
4
alkoxy are likewise linear or branched and have, for example, the meanings given above up to the corresponding number of carbon atoms. R
1
is, for example, C
1
-C
4
alkoxy, especially methoxy or ethoxy, preferably ethoxy. R
3
, R
4
and R
5
are, for example, C
1
-C
4
alkoxy, especially methoxy.
Phenyl-C
1
-C
4
alkyl is phenyl-substituted C
1
-C
4
alkyl and is, for example, benzyl, phenylethyl, &agr;-methylbenzyl, phenylpropyl or &agr;,&agr;-dimethylbenzyl, especially benzyl. Phenyl-C
1
-C
2
alkyl is preferred.
Halogen is fluorine, chlorine, bromine or iodine, especially chlorine or bromine, preferably chlorine.
C
2
-C
12
Alkenyl radicals may be mono- or poly-unsaturated and linear or branched and are, for example, C
2
-C
8
-, C
2
-C
6
- or C
2
-C
4
-alkenyl. Examples are allyl, methallyl, 1,1-dimethylallyl, 1-butenyl, 2-butenyl, 1,3-pentadienyl, 1-hexenyl, 1-octenyl, decenyl and dodecenyl, especially allyl. R
1
as C
2
-C
12
alkenyl is, for example, C
2
-C
8
-, C
2
-C
6
- or, especially, C
2
-C
4
-alkenyl.
R
1
as substituted phenyl is mono- to penta-substituted, for example mono-, di- or tri-substituted, especially mono- or di-substituted, on the phenyl ring. Preferred substituents for R
1
as substituted phenyl are C
1
-C
4
alkyl, especially methyl, and C
1
-C
6
alkoxy, especially pentyloxy and methoxy.
When R is the radical
the meanings of R
3
, R
4
and R
5
in that radical do not necessarily have to be identical to those of the radicals R
3
, R
4
and R
5
in the other benzoyl group in the compound of formula I, that is to say, suitable compounds of formula I also include asymmetrical bisacylphosphine oxides.
The expression “and/or” in relation to the definition of the present invention indicates that not only one of the defined alternatives (substituents) but several different defined alternatives (substituents) may be present together, that is to say, mixtures of different alternatives (substituents) may be present.
The expression “at least one” defines “one” or “more than one”, for example one, two or three, preferably one or two.
The preparation of the compounds of formula I is known to the person skilled in the art and is widely described in the literature. For example, corresponding processes are described in the following specifications: U.S. Pat. No. 4,737,593, U.S. Pat. No. 4,792,632, U.S. Pat. No. 5,218,009, U.S. Pat. No. 4,298,738, U.S. Pat. No. 5,504,236, U.S. Pat. No. 5,399,770, U.S. Pat. No. 5,767,169.
For example, compounds of formula I having two benzoyl groups (bisacylphosphine oxides) can be prepared, for example, by double acylation of a primary phosphine using at least two equivalents of an acid chloride in the presence of at least two equivalents of a base, and subsequent oxidation of the resulting diacylphosphine. The reaction conditions can be obtained from the above-mentioned literature sources.
The monoacylphosphine oxides can be obtained in an analogous manner.
Some of the compounds of formula I are also obtainable commercially, such as, for example, 2,4,6-trimethylbenzoyldiphenylphosphine oxide (
RTM
Lucirin TPO, BASF); bis(2,4,6-trimethyl-benzoyl)phenylphosphine oxide (
RTM
Irgacure 819, Ciba Spezialitätenchemie) and bis(2,6-di-methoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide (as
RTM
Irgacure 1700,
RTM
Irgacure 1800 and
RTM
Irgacure 1850 in admixture with a-hydroxyketones from Ciba Spezialitätenchemie).
In the suspensions according to the invention, preference is given to the compounds of formula I wherein
R
1
is C
1
-C
20
alkyl; C
1
-C
4
alkoxy; or phenyl that is unsubstituted or substituted by C
1
-C
12
alkyl, C
1
-C
12
alkoxy and/or by halogen;
R
2
is the radical
or has one of the meanings given for R
1
;
R
3
and R
4
are each independently of the other C
1
-C
4
alkyl or C
1
-C
4
alkoxy; and R
5
is hydrogen, C
1
-C
12
alkyl or C
1
-C
12
alkoxy.
Preference is given also lo an aqueous suspension comprising as component (a) a compound of formula I wherein
R
1
is C
1
-C
20
alkyl; C
2
-C
20
alkyl interrupted by one or more O atoms; benzyl; or phenyl that is unsubstituted or substituted by C
1
-C
20
alkyl, C
1
-C
12
alkoxy and/or by halogen;
R
2
is the radical
or has one of the meanings given for R
1
;
R
3
and R
4
are each independently of the other C
1
-C
4
alkyl, C
1
-C
4
alkoxy or halogen; and R
5
is hydrogen, C
1
-C
12
alkyl, C
1
-C
12
alkox

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