Photopolymerization compositions including maleimides and processes for using the same
AssigneeAlbemarle Corporation
InventorsCharles E. Hoyle, Rajamani Nagarajan, Christopher W. Miller, Shan Christopher Clark, E. Sonny Jönsson, Liying Shao
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Abstract
Photopolymerization compositions which include maleimides and processes using the same are disclosed. Polymerization of compositions which include maleimides in combination with a benzophenone compound/hydrogen atom donor sensitizer system may be activated by irradiating the composition with radiation.
Claims64
A photopolymerizable composition comprising at least one photopolymerizable compound having at least one ethylenically unsaturated double bond, at least one maleimide compound capable of initiating photopolymerization of said ethylenically unsaturated compound in an amount of about 0.01 to about 2 mole percent, and at least one photoactive benzophenone compound which is a sensitizer capable of sensitizing initiation of the ethylenically unsaturated compound by said maleimide.
A photopolymerizable composition comprising at least one photopolymerizable compound having at least one ethylenically unsaturated double bond, at least one maleimide compound capable of initiating photopolymerization of said ethylenically unsaturated compound of the formula
- wherein each R1 and R2 is independently selected from the group consisting of hydrogen, C1 to C10 alkyl, cycloalkyl, aryl, alkoxy, and halogen, or R1 and R2 together form a fused substituted or unsubstituted saturated or unsaturated five or six membered cyclic hydrocarbon or heterocyclic ring system, and at least one photoactive compound without a maleimide functionality which is a sensitizer capable of sensitizing initiation of the ethylenically unsaturated compound by said maleimide.
A photopolymnerizable composition comprising at least one photopolymerizable compound having at least one ethylenically unsaturated double bond at least one maleic anhydride capable of initiating photopolymeration of said ethylenically unsaturated compound of the formula
- wherein each R1 and R2 is independently selected from the group consisting of hydrogen, C1 to C10 alkyl, cycloalkyl, aryl, alkoxy, and halogen, or R1 and R2 together form a fused substituted or unsubstituted saturated or unsaturated five or six membered cyclic hydrocarbon or heterocyclic ring system, and at least one photoactive compound without a maleimide functionality which is a sensitizer capable of sensitizing initiation of the ethylenically unsaturated compound by said maleic anhydride.
A method of polymerizing a polymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing said compound to radiation in the presence of at least one maleimide compound in an amount of about 0.01 to about 2 mole percent and at least one photoactive benzophenone compound, wherein said maleimide initiates photopolymerization of said ethylenically unsaturated compound and wherein said photoactive benzophenone compound sensitizes initiation of the ethylenically unsaturated compound by said maleimide.
A method of polymerizing a compound having at least one ethylenically unsaturated double bond, comprising exposing said compound to radiation in the presence of at least one maleimide compound of the formula
- wherein each R1 and R2 is independently selected from the group consisting of hydrogen, C1 to C10 alkyl, cycloalkyl, aryl, alkoxy, and halogen, or R1 and R2 together form a fused substituted or unsubstituted saturated or unsaturated five or six membered cyclic hydrocarbon or heterocyclic ring system, and at least one photoactive compound without a maleimide functionality, wherein said maleimide compound initiates photopolymerization of said ethylenically unsaturated compound and wherein said photoactive compound sensitizes initiation of the ethylenically unsaturated compound by said maleimide.
A method of polymerizing a compound having at least one ethylenicaUy unsaturated double bond, comprising exposing said compound to radiation in the presence of at least one maleic anhydride of the formula
- wherein each R1 and R2 is independently selected from the group consisting of hydrogen, C1 to C10 alky), cycloalkyl, aryl, alkoxy, and halogen, or R1 and R2 together form a fused substituted or unsubstituted saturated or unsaturated five or six membered cyclic hydrocarbon or heterocyclic ring system, and at least one photoactive compound without a maleimide functionality, wherein said maleimide compound initiates photopolymerization of said ethylenically unsaturated compound and wherein said photoactive compound sensitizes initiation of the ethylenically unsaturated compound by said maleic anhydride.
A photopolymerizable composition comprising at least one photopolymerizable compound having at least one ethylenically unsaturated double bond, di(4-maleimidophenyl)methane and 4-phenylbenzophenone.
A method of polymerizing a polymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing said compound to radiation in the presence of di(4-maleimidophenyl)methane and 4-phenylbenzophenone.
A photopolymerizable composition comprising at least one photopolymerizable compound having at least one ethylenically unsaturated double bond, at least one maleimide capable of initiating photopolymerization of said ethylenically unsaturated compound in an amount of about 0.01 to about 2 mole percent, and at least one photoactive compound without a maleimide functionality which is a sensitizer capable of sensitizing initiation of the ethylenically unsaturated compound by said maleimide, wherein said maleimide compound comprises an alkyl maleimide of the formula
- wherein:
- each R1 and R2 is independently selected from the group consisting of hydrogen, C1 to C10 alkyl, cycloalkyl, aryl, alkoxy, and halogen, or R1 and R2 together form a fused substituted or unsubstituted saturated or unsaturated five or six membered cyclic hydrocarbon or heterocyclic ring system;
- and
- R is straight chain, branched or cyclic C1-C10 alkyl, optionally substituted with one or more C1-C4 alkyl.
A photopolymerizable composition comprising at least one photopolymerizable compound having at least one ethylenically unsaturated double bond, at least one maleimide capable of initiating photopolymerization of said ethylenically unsaturated compound in an amount of about 0.01 to about 2 mole percent, and at least one photoactive benzophenone compound which is a sensitizer capable of sensitizing initiation of the ethylenically unsaturated compound by said maleimide, wherein said benzophenone compound comprises a compound of the formula
- wherein:
- B is (H,H), —CH2—, —S—, —CO—, —NR15—, or a bond bridging the two aromatic rings;
- each R14 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkoxy, aryl, alkylaryl, arylalkyl, halogen, trihaloalkyl, —CN, —NO2, —C(O)OR15, —C(O)R15, —OR15, —N(R15)2, —OC(O)CR15═CHR15, R16, —OR16, —R17—OC(O)CR15, polymerizable moieties, and oligomeric and polymeric moieties;
- R15 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl;
- R16 is one or more saturated or unsaturated five or six membered hydrocarbon or heterocyclic ring system, optionally substituted with one or more alkyl, cycloalkyl, or halogen;
- and
- R17 is selected from the group consisting of alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl.
A photopolymerizable composition, comprising at least one photopolymerizable compound having at least one ethylenically unsaturated double bond, at least one maleimide capable of initiating photopolymerization of said ethylenically unsaturated compound in an amount of about 0.01 to about 2 mole percent, and at least one photoactive benzophenone compound which is a sensitizer capable of sensitizing initiation of the ethylenically unsaturated compound by said maleimide, wherein said benzophenone compound is selected from the group consisting benzophenone, thioxanthone, isopropylthioxanthone, chloroxanthone, 4-morpholinobenzophenone, 4,4′-diphenoxybenzophenone, methyl o-benzoylbenzoate, 1-methyl-2-(2-ethylhexyloxy)thioxanthone, 4,4′-di-(4-isopropylphenoxy)benzophenone, acrylic acid 4-benzoylphenyl ester, 4,4′-diphenylbenzophenone, 4-phenylbenzophenone, and mixtures thereof.
A method of polymerizing a polymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing said compound to radiation in the presence of at least one maleimide compound in an amount of about 0.01 to about 2 mole percent and at least one photoactive compound without a maleimide functionality, wherein said maleimide initiates photopolymerization of said ethylenically unsaturated compound and wherein said photoactive compound sensitizes initiation of the ethylenically unsaturated compound by said maleimide, wherein said maleimide compound comprises an alkyl maleimide of the formula
- wherein:
- each R1 and R2 is independently selected from the group consisting of hydrogen, C1 to C10 alkyl, cycloalkyl, aryl, alkoxy, and halogen, or R1 and R2 together form a fused substituted or unsubstituted saturated or unsaturated five or six membered cyclic hydrocarbon or heterocyclic ring system;
- and
- R is straight chain, branched or cyclic C1-C10 alkyl, optionally substituted with one or more C1-C4 alkyl.
A method of polymerizing a polymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing said compound to radiation in the presence of at least one maleimide compound in an amount of about 0.01 to about 2 mole percent and at least one photoactive benzophenone compound without a maleimide functionality, wherein said maleimide initiates photopolymerization of said ethylenically unsaturated compound and wherein said photoactive benzophenone compound sensitizes initiation of the ethylenically unsaturated compound by said maleimide, wherein said benzophenone compound has the formula
- wherein:
- B is (H,H), —CH2—, —S—, —O—, —CO—, —NR15—, or a bond bridging the two aromatic rings;
- each R14 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkoxy, aryl, alkylaryl, arylalkyl, halogen, trihaloalkyl, —CN, —NO2, —C(O)OR15, —C(O)R15, —OR15, —N(R15)2, —OC(O)CR15═CHR15, R16, —OR16, —R17—OC(O)CR15═CHR15, polymerizable moieties, and oligomeric and polymeric moieties;
- R15 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl;
- R16 is one or more saturated or unsaturated five or six membered hydrocarbon or heterocyclic ring system, optionally substituted with one or more alkyl, cycloalkyl, or halogen;
- and
- R17 is selected from the group consisting of alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl.
A method of polymerizing a polymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing said compound to radiation in the presence of at least one maleimide compound in an amount of about 0.01 to about 2 mole percent and at least one photoactive benzophenone compound without a maleimide functionality, wherein said maleimide initiates photopolymerization of said ethylenically unsaturated compound and wherein said photoactive benzophenone compound sensitizes initiation of the ethylenically unsaturated compound by said maleimide, wherein said benzophenone compound is selected from the group consisting benzophenone, thioxanthone, isopropylthioxanthone, chlorothioxanthone, 4-morpholinobenzophenone, 4,4′-diphenoxybenzophenone, methyl o-benzoylbenzoate, 1-methyl-2-(2-ethylhexyloxy)thioxanthone, 4,4′-di-(4-isopropylphenoxy)benzophenone, acrylic acid 4-benzoylphenyl ester, 4,4′-diphenylbenzophenone, 4-phenylbenzophenone, and mixtures thereof.
A method of polymerizing a polymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing said compound to radiation in the presence of at least one maleimide compound in an amount of about 0.01 to about 2 mole percent and at least one photoactive benzophenone compound, wherein said maleimide initiates photopolymerization of said ethylenically unsaturated compound and wherein said photoactive benzophenone compound sensitizes initiation of the ethylenically unsaturated compound by said maleimide, wherein said photoactive benzophenone compound comprises a benzophenone compound of the formula
- wherein:
- B is (H,H);
- at least one R14 is aryl and the other R14 are hydrogen;
- R15 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl;
- R16 is one or more saturated or unsaturated five or six membered hydrocarbon or heterocyclic ring system, optionally substituted with one or more alkyl, cycloalkyl, or halogen;
- and
- R17 is selected from the group consisting of alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl.
Dependencies are inferred from the claim text.