Highly efficient free radical photopolymerizations through enabled dark cure
AssigneeThe Regents of the University of Colorado, a body corporate
InventorsJeffrey W. Stansbury, Kangmin Kim, Charles B. Musgrave, Jasmine Sinha
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Abstract
A quaternary ammonium salt comprising a chromophore constituent, a tertiary amine cation constituent connected to the para-position of the chromophore constituent via a methylene linkage, and a borate anion constituent, wherein chromophore constituent is a 3-ketocoumarin constituent or a benzophenone constituent. Also, a photobase-redox initiating system comprising the quaternary ammonium salt and a peroxide.
Claims11
A quaternary ammonium salt comprising a chromophore constituent, a tertiary amine cation constituent connected to the para-position of the chromophore constituent via a methylene linkage, and a borate anion constituent, wherein chromophore constituent is a 3-ketocoumarin constituent and the quaternary ammonium salt has the formula (I)
- wherein:
- R1 and R2, identical or different, are independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group,
- where R″ is a linear or branched C1-C8 alkyl group, unsubstituted or substituted -phenyl group, unsubstituted or substituted -naphthyl group, unsubstituted or substituted -vinyl group, -halogen, and halogenated C1-C8-alkyl group;
- R3 is selected from the group consisting of independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group, -halogen, and halogenated -alkyl group;
- R4 is selected from the group consisting of independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group, -halogen, and halogenated C1-C8-alkyl group;
- R5, identical or different, is independently selected from the group consisting of linear or branched C1-C8 N-alkyl group;
- hydroxyl-substituted C1-C8 N-alkyl group;
- fused 5-7 member heterocyclic ring;
- and unsubstituted or substituted aromatic ring, wherein the substituent on the aromatic ring is selected from the group consisting of linear or branched C1-C8 alkyl group and linear or branched C1-C8 alkoxy group;
- and
- R6, identical or different, is independently selected from the group consisting of linear or branched C1-C8 alkyl group, and unsubstituted or substituted aromatic ring wherein the substituent on the aromatic ring is selected from the group consisting of linear or branched C1-C8 alkyl group, linear or branched C1-C8 alkoxy group, and halogen.
A quaternary ammonium salt comprising a chromophore constituent, a tertiary amine cation constituent connected to the para-position of the chromophore constituent via a methylene linkage, and a borate anion constituent, wherein chromophore constituent is a 3-ketocoumarin constituent and the quaternary ammonium salt has the formula (I) or the chromophore constituent is a benzophenone constituent and the quaternary ammonium salt has the formula (II)
- wherein
- R1 and R2, identical or different, are independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group,
- where R″ is a linear or branched C1-C8 alkyl group, unsubstituted or substituted -phenyl group, unsubstituted or substituted -naphthyl group, unsubstituted or substituted -vinyl group, -halogen, and halogenated C1-C8-alkyl group;
- R3 is selected from the group consisting of independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group, -halogen, and halogenated -alkyl group;
- R4 is selected from the group consisting of independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group, -halogen, and halogenated C1-C8-alkyl group;
- R5, identical or different, is independently selected from the group consisting of linear or branched C1-C8 N-alkyl group;
- hydroxyl-substituted C1-C8 N-alkyl group;
- fused 5-7 member heterocyclic ring;
- and unsubstituted or substituted aromatic ring, wherein the substituent on the aromatic ring is selected from the group consisting of linear or branched C1-C8 alkyl group and linear or branched C1-C8 alkoxy group;
- and
- R6, identical or different, is independently selected from the group consisting of linear or branched C1-C8 alkyl group, and unsubstituted or substituted aromatic ring wherein the substituent on the aromatic ring is selected from the group consisting of linear or branched C1-C8 alkyl group, linear or branched C1-C8 alkoxy group, and halogen;
- and
- wherein the amine cation constituent is selected from the group consisting of N-methyl morpholine, N-methyl pyrrolidine, N,N-dimethyl aniline, N,N,4-trimethyl aniline, N,N-dimethyl-4-methoxyaniline, N,N-pyrrolidine-4-methoxyaniline, and N,N-ethoxy-4-methylaniline.
A photobase-redox initiating system comprising a quaternary ammonium salt and a peroxide,
- wherein the quaternary ammonium salt comprises a chromophore constituent, a tertiary amine cation constituent connected to the para-position of the chromophore constituent via a methylene linkage, and a borate anion constituent, wherein chromophore constituent is a 3-ketocoumarin constituent and the quaternary ammonium salt has the formula (I) or the chromophore constituent is a benzophenone constituent and the quaternary ammonium salt has the formula (II)
- wherein
- R1 and R2, identical or different, are independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group,
- where R″ is a linear or branched C1-C8 alkyl group, unsubstituted or substituted -phenyl group, unsubstituted or substituted -naphthyl group, unsubstituted or substituted -vinyl group, -halogen, and halogenated C1-C8-alkyl group;
- R3 is selected from the group consisting of independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group, -halogen, and halogenated -alkyl group;
- R4 is selected from the group consisting of independently selected from the group consisting of —H, —OH, linear or branched C1-C8-alkoxy group, -halogen, and halogenated C1-C8-alkyl group;
- R5, identical or different, is independently selected from the group consisting of linear or branched C1-C8 N-alkyl group;
- hydroxyl-substituted C1-C8 N-alkyl group;
- fused 5-7 member heterocyclic ring;
- and unsubstituted or substituted aromatic ring, wherein the substituent on the aromatic ring is selected from the group consisting of linear or branched C1-C8 alkyl group and linear or branched C1-C8 alkoxy group;
- and
- R6, identical or different, is independently selected from the group consisting of linear or branched C1-C8 alkyl group, and unsubstituted or substituted aromatic ring wherein the substituent on the aromatic ring is selected from the group consisting of linear or branched C1-C8 alkyl group, linear or branched C1-C8 alkoxy group, and halogen;
- and
- wherein the peroxide is selected from the group consisting of benzoyl peroxide, dilauroyl peroxide, dialkylperoxydicarbonate, phthaloyl peroxide, dicumyl peroxide, and combinations thereof.
Dependencies are inferred from the claim text.