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Siloxane polyphotoinitiators of the substituted acetophenone type
| Details |
Inventors: Lin, Samuel Q. S.; Jacobine, Anthony F.;
Assignee: Loctite Corporation (Newington, CT)
Primary Examiner:
Assistant Examiner:
Attorney, Agent or Firm:
An organopolysiloxane photoinitiator having an average of at least two siloxane units, of which at least an average of one siloxane unit per organopolysiloxane molecule has the formula: X.sub.a R.sub.b SiO(.sub.4-a-b)/2 (I) wherein a is an integer of 1-3, b is an integer of 0-2 and a plus b equals 1-3; R is C.sub.1 -C.sub.10 hydrocarbyl or halogen substituted C.sub.1 -C.sub.10 hydrocarbyl; and X is a substituted acetophenone photomoiety selected from: ##STR1## where R.sup.1 is any substituent which will not interfere with hydrosilation, n is an integer between 0 and 5 in formulas (II), (IIa), (III), (IIIa), (IV) and (IVa) and between 0 and 4 in formula (III) and (IIIa); m is 0 or 1; R.sup.2 is alkyl or substituted alkyl; R.sup.3 is H, alkyl or aryl; R.sup.4 is a divalent hydrocarbon group having between 2 and 10 carbon atoms or an alkylene oxy alkylene group; R.sup.5 is a group selected from H, alkyl, aryl, organosilyl, or the reaction product of an isocyanate esterification reagent or an etherification reagent with the hydroxyl product formed when R.sup.5 is H and R.sup.6 is a trivalent hydrocarbon or hydrocarbon oxyhydrocarbon group. The silicones are prepared by hydrosilation of the corresponding olefinically or acetylenically unsaturated acetophenones. |
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DETAILED DESCRIPTION OF THE INVENTION The inventive polyphotoinitiators are organopolysiloxanes having an average of at least two siloxane units, of which at least an average of one siloxane unit per organopolysiloxane molecule has the formula: X.
sub.
a R.
sub.
b SiO.
sub.
(4-a-b)/2 (I) wherein a is an integer of 1-3, b is an integer of 0-2 and a plus b equals 1-3; R is C.
sub.
1 -C.
sub.
10 hydrocarbyl or halogen substituted C.
sub.
1 -C.
sub.
10 hydrocarbyl; and X is a substituted acetophenone photomoiety selected from: ##STR2## where R.
sup.
1 is any substitutent which will not interfere with hydrosilation, n is an integer between 0 and 5 in formulas (II) and (III) and between 0 and 4 in formula (III); m is 0 or 1; R.
sup.
2 is alkyl or substituted alkyl; R.
sup.
3 is H, alkyl or aryl; R.
sup.
4 is a divalent hydrocarbon group having between 2 and 10 carbon atoms; R.
sup.
5 is a group selected from H, aryl, organosilyl, or the reaction product of an isocyanate, esterifying reagent or etherification reagent with the hydroxyl product formed when R.
sup.
5 is H.
Suitable R groups in the above formula include alkyls such as methyl and ethyl, halogen substituted alkyls such as trifluoropropyl and aryls such as phenyl.
Suitable R.
sup.
1 substituents include halo, alkyl, and alkoxy.
The R.
sup.
2 groups may be linear, branched or cyclic alkyls or substituted alkyls, including methyl, ethyl, cyclohexyl, cyclooctyl, trichloroethyl, trifluoropropyl and organosilylalkyl such as (pentamethyldisiloxy)propyl and trimethylsilylpropyl.
In general the R.
sup.
2 alkyl groups may be substituted with any radical which will not interfere with hydrosilation or the photoinitiating ability of the photomoiety.
It should be understood that combined cyclic structures are intended to be encompassed within the invention.
Thus, cyclic acetal or ketal structures may be formed by a carbon-to-carbon linkage of R.
sup.
2 and R.
sup.
4 in formula (II) or the R.
sup.
2 groups in formula (III).
Cycloaliphatic structures may be formed by a carbon-to-carbon linkage of R
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