Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Reexamination Certificate
2000-04-11
2001-05-22
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...
C522S168000, C522S167000, C522S122000, C522S170000, C522S169000, C528S413000, C528S414000, C528S411000, C527S503000, C527S503000, C527S503000
Reexamination Certificate
active
06235808
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel radiation-curable cycloaliphatic epoxy compounds, to radiation-curable compositions containing such compounds, and to processes for forming radiation-cured products from such compounds and compositions.
BACKGROUND OF THE INVENTION
Radiation curing has become an important and useful technique for applying and curing coatings, inks, and adhesives. As described herein, radiation curing involves presenting a radiation-curable monomer, typically in combination with a photoinitiator, and exposing the composition to radiation in the form of ultraviolet or electron-beam radiation to cause the radiation-curable compound to polymerize.
Radiation curing presents many advantages, such as high rates of throughput, low energy requirements, and low equipment costs. In addition, it is advantageous that users are able to avoid using a solvent when the composition to be radiation-cured is prepared. Solvents typically would lead to environmental and/or safety hazards, and would require additional equipment and handling steps to remove the solvent.
There remains a need for radiation-curable compounds, photopolymerizable or otherwise, which provide improved polymerizability and which can be formulated into a variety of coatings, films and the like readily and rapidly.
BRIEF SUMMARY OF THE INVENTION
The present invention is directed to compounds which contain 1 to 3 cycloaliphatic epoxy groups and an oxidizable group containing an ether linkage or an ethylenic or acetylenic bond, and which undergo photopolymerization when exposed to ultraviolet, electron beam or X-ray irradiation in the presence of a photoinitiator.
Included among these are compounds of formulas (1), (2), (3) and (4):
wherein
i is 1, 2, or 3;
R
b
is hydrogen or straight or branched alkyl containing 1 to 20 carbon atoms;
R
c
is hydrogen or straight or branched alkyl containing 1 to 20 carbon atoms;
R
e
is a single bond or straight or branched divalent alkyl containing 1 to 20 carbon atoms;
a is 0 or 1, and f is 0 or 1;
Y is hydrogen or straight or branched alkyl containing up to 12 carbon atoms;
one of L and M is —CH
2
— and the other is a single bond;
when i is 1, AG is —OM or a monovalent heterocyclic group containing 3, 4 or 5 carbon atoms and 1 or 2 oxygen atoms, wherein M is straight or branched alkyl containing 2 to 20 carbon atoms which contains a C═C bond, a C≡C bond, or an ether oxygen, or M is phenyl, benzyl, or a monovalent heterocyclic group containing 3, 4 or 5 carbon atoms and 1 or 2 oxygen atoms, and AG is optionally substituted with an R group;
when i is 2, AG is —O—D—O— wherein D is divalent straight or branched alkyl containing up to 20 carbon atoms which optionally contains a C═C bond or a C≡C bond, and which is optionally substituted with an R group, wherein D can optionally be interrupted with an ether oxygen, C
6
H
4
phenylene, or cycloalkyl containing 2 to 20 carbon atoms and 0-2 oxygen atoms;
when i is 3, AG is —O—T(—O—)—O—, wherein T is trivalent straight or branched alkyl containing up to 25 carbon atoms which optionally contains a C═C bond or a C≡C bond, wherein T can optionally be interrupted with an ether oxygen; or T is a cycloalkyl group of 3 to 25 carbon atoms or a phenyl group and is substituted with 3 groups each independently having the formula C
t
H
2t
wherein t is 1 to 20;
R is phenyl optionally substituted with a G group, or cycloalkyl or cycloalkyl-alkyl containing 5 to 25 carbon atoms wherein up to 2 ring carbon atoms are replaced with oxygen atoms, and R is optionally substituted with a G group; and
G is alkyl containing 1 to 20 carbon atoms, —CHO, alkoxy containing 1 to 20 carbon atoms, cycloalkoxy or cycloalkyl containing 5 to 25 carbon atoms, —COOH, —NO
2
, phenyl, halo, or vinyl.
Another aspect of the present invention is compositions comprising one or more of said compounds of formulas (1)-(4) and also comprising one or more photoinitiators in an amount effective to mediate polymerization of said compound when the composition is irradiated with, for instance, ultraviolet radiation or electron beam radiation or X-ray radiation.
Yet another aspect of the present invention is a process of forming a polymeric structure, such as a coating, film, or solid body, comprising forming the aforementioned composition of one or more compounds of formula (1)-(4) and a photoinitiator, and then irradiating the composition with ultraviolet, or X-ray or electron beam radiation effective to polymerize said one or more compounds of formula (1)-(4).
Methods of making the aforementioned compounds are also within the scope of the present invention.
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McClendon Sanza L
Rensselaer Polytechnic Institute
Scully Scott Murphy & Presser
Seidleck James J.
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