Polymerization processes using aliphatic maleimides
AssigneesAlbemarle Corporation, The University of Southern Mississippi
InventorsCharles E. Hoyle, Shan Christopher Clark, E. Sonny Jönsson
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Abstract
Aliphatic maleimides and methods using the same are disclosed. Polymerization of compositions which include the compounds of the invention may be activated by irradiating the composition with radiation.
Claims84
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond as a majority component and at least one multifunctional maleimide photoinitiator resulting from the reaction of a maleimide compound of the formula
- wherein
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) R is linear or branched C1 to C10 alkylene;
- and
- (c) FG comprises a functional group selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium,
- with a spacer group to link said maleimide unit with at least one other maleimide unit to form a multifunctional maleimide compound,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond and at least one multifunctional maleimide photoinitiator resulting from the reaction of a maleimide compound of the formula
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) R is linear or branched C1 to C10 alkylene;
- and
- (c) FG comprises a urethane functional group,
- with a spacer group to link said maleimide unit with at least one other maleimide unit to form a multifunctional maleimide compound.
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond and at least one multifunctional maleimide photoinitiator isophorone bisurethane bisethylmaleimide (IPBUBEMI).
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing a composition comprising said photopolymerizable compound as a majority component to radiation in the presence of at least one multi-functional maleimide photoinitiator resulting from the reaction of a maleimide compound of the formula
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) R is linear or branched C1 to C10 alkylene;
- and
- (c) FG comprises a functional group selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium,
- with a spacer group to link said maleimide unit with at least one other maleimide unit to form a multifunctional maleimide compound,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing a photopolymerizable compound to radiation in the presence of at least one multi-functional maleimide photoinitiator resulting from the reaction of a maleimide compound of the formula
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) R is linear or branched C1 to C10 alkylene;
- and
- (c) FG comprises a urethane functional group,
- with a spacer group to link said maleimide unit with at least one other maleimide unit to form a multifunctional maleimide compound.
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing a photopolymerizable compound to radiation in the presence of isophorone bisurethane bisethylmaleimide (IPBUBEMI)
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond as a majority component and at least one di-maleimide functional aliphatic photoinitiator resulting from the reaction of a maleimide compound of the formula:
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) R is linear or branched C1 to C10 alkylene;
- and
- (c) FG comprises a functional group selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium,
- with a spacer group to link said maleimide unit with at least one other maleimide unit to form a di-functional maleimide compound,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing a composition comprising said photopolymerizable compound as a majority component to radiation in the presence of at least one di-maleimide functional photoinitiator resulting from the reaction of a maleimide compound of the formula
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) R is linear or branched C1 to C10 alkylene;
- and
- (c) FG comprises a functional group selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium,
- with a spacer group to link said maleimide unit with at least one other maleimide unit to form a di-functional maleimide compound,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond as a majority component and at least one di-functional maleimide photoinitiator of the formula
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) R is linear or branched C1 to C10 alkylene;
- (c) FG″ is independently a residue of a functional group FG selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium reacted with a spacer group SP;
- and
- (d) SP is a spacer group,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond and at least one di-functional maleimide photoinitiator of the formula
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ comprises a residue of a urethane functional group reacted with a spacer group SP;
- and
- (d) SP is a spacer group.
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing a composition comprising said photopolymerizable compound as a majority component to radiation in the presence of at least one di-functional maleimide photoinitiator of the formula
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ is independently a residue of a functional group FG selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium reacted with a spacer group SP;
- and
- (d) SP is a spacer group,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing a composition comprising said photopolymerizable compound as a majority component to radiation in the presence of at least one di-functional maleimide photoinitiator of the formula
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ comprises a residue of a urethane functional group reacted with a spacer group SP;
- and
- (d) SP is a spacer group.
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond as a majority component and at least one multi-functional aliphatic maleimide photoinitiator of the formula:
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ independently comprises a residue of a functional group FG selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium reacted with a spacer group SP;
- (d) SP comprises a spacer group;
- and
- (e) n is greater than 2,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing a composition comprising said photopolymerizable compound as a majority component to radiation in the presence of at least one multi-functional aliphatic maleimide photoinitiator of the formula:
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ independently comprises a residue of a functional group FG selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium reacted with a spacer group SP;
- (d) SP comprises a spacer group;
- and
- (e) n is greater than 2,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing said photopolymerizable compound to radiation in the presence of at least one multi-functional aliphatic maleimide photoinitiator of the formula:
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen,
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ independently comprises a residue of a urethane functional group reacted with a spacer group SP;
- (d) SP comprises a spacer group;
- and
- (e) n is greater than 2.
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond as a majority component and at least one di-functional aliphatic maleimide photoinitiator of the formula:
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ independently comprises a residue of a functional group FG selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium reacted with the R group,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A method of photopolymerizing a photopolymerizable compound having at least one ethylenically unsaturated double bond, comprising exposing a composition comprising said photopolymerizable compound as a majority component to radiation in the presence of at least one di-functional aliphatic maleimide photoinitiator of the formula:
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ independently comprises a residue of a functional group FG selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, —CH2N-aryl-FG′, —CH2N-aryl-R3-FG′, sulfonic acid, quaternary ammonium, and salts thereof, in which each R3 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, arylalkyl, and alkylaryl and in which FG′ is selected from the group consisting of —OR3, —SR3, —Si(R3)3, —OC(O)N(R3)2, —OC(O)C(═CHR3)R3, —OC(O)R3, —C(O)R3, —N(R3)2, —C(O)OR3, —NCO, —C(O)N(R3)2, —OC(O)OR3, —CN, halogen, sulfonic acid, and quaternary ammonium reacted with the R group,
- wherein said composition optionally further comprises a compound to accelerate polymerization of the photopolymerizable compound by the maleimide photoinitiator.
A photopolymerizable composition comprising a photopolymerizable compound having at least one ethylenically unsaturated double bond and at least one multi-functional aliphatic maleimide photoinitiator of the formula:
- wherein:
- (a) each R1 and R2 is independently selected from the group consisting of hydrogen, linear or branched C1 to C4 alkyl, and halogen;
- (b) each R is independently linear or branched C1 to C10 alkylene;
- (c) each FG″ comprises a residue of a urethane functional group reacted with a spacer group SP;
- (d) SP comprises a spacer group;
- and
- (e) n is greater than 2.
Dependencies are inferred from the claim text.