CA2412607A1 - Novel photoinitiators and applications therefor - Google Patents

Novel photoinitiators and applications therefor Download PDF

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Publication number
CA2412607A1
CA2412607A1 CA002412607A CA2412607A CA2412607A1 CA 2412607 A1 CA2412607 A1 CA 2412607A1 CA 002412607 A CA002412607 A CA 002412607A CA 2412607 A CA2412607 A CA 2412607A CA 2412607 A1 CA2412607 A1 CA 2412607A1
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Prior art keywords
carbon atoms
alkyl group
photoinitiator
group
generating
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Granted
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CA002412607A
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French (fr)
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CA2412607C (en
Inventor
Ronald Sinclair Nohr
John Gavin Macdonald
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Tamiras Per Pte Ltd LLC
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Individual
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors

Abstract

The present invention is directed to new, energy-efficient, photoinitiators having the following formula: whrein Z each independlently represent the formula (II) wherein R1, R2, R3 and R4 each independently represent hydrogen, an alkyl group having from one to six carbon atoms, an alkoxy group having from one to six carbon atoms, or a halogen-substituted alkyl group; R5, R6, R7 and R8 each independently represent an alkyl group having from one to six carbon atoms, an aryl group, or a halogen-substituted alkyl group having from one to six carbon atoms; wherein R9 represents (R10)2O or (R10)3N, wherein R10 represents H or an alkyl group having from one to eight carbon atoms; and wherein R11 represents H, an alkyl group having from one to eight carbon atoms, a benzyl group or an aralkyl group. The present invention is also directed to a method of generating a reactive species, methods of polymerizing polymerizable materials, methods of curing an unsaturated oligomer/monomer mixture, and methods of laminating using the photoinitiators of the present invention. In addition, the present invention is directed to ink compositions, adhesive compositions and resins, and methods of printing using the above-described photoinitiators.

Claims (20)

1. A photoinitiator having the general formula:

wherein Z each independently represents wherein R1, R2, R3 and R4 each independently represent hydrogen, an alkyl group having from one to six carbon atoms, an alkoxy group having from one to six carbon atoms, or a halogen-substituted alkyl group; R5, R6, R7 and R8 each independently represent an alkyl group having from one to six carbon atoms, an aryl group, or a halogen-substituted alkyl group having from one to six carbon atoms; wherein R9 represents (R10)2O or (R10)3N;
wherein R10 represents H or an alkyl group having from one to eight carbon atoms; and wherein R11 represents H, an alkyl group having from one to eight carbon atoms, a benzyl group or an aralkyl group.
2. The photoinitiator of Claim 1, wherein the photoinitiator comprises:

or
3. The photoinitiator of Claim 1, wherein the photoinitiator is associated with one or more counterions.
4. The photoinitiator of Claim 1, wherein the one or more counterions comprise tetraphenylboron, tetrachloroboron, tetrafluoroboron, hexafluorophosphate, perchlorate, or a combination thereof.
5. The photoinitiator of Claim 4, wherein the one or more counterions comprise tetraphenylboron or tetrafluoroboron.
6. The photoinitiator of Claim 3, wherein the photoinitiator and the one or more counterions comprise
7. A method of generating a reactive species, comprising:
irradiating the photoinitiator of Claim 1 with radiation.
8. A method of polymerizing a polymerizable material, comprising:
irradiating an admixture of a polymerizable material and the photoinitiator of Claim 1.
9. A method of generating a reactive species, comprising:
irradiating a photoinitiator with radiation, wherein at least one cationic free radical and at least one nitrogen radical species are generated.
10. The method of generating a reactive species of Claim 9, wherein the photoinitiator has the general formula:

wherein Z each independently represent wherein R1, R2, R3 and R4 each independently represent hydrogen, an alkyl group having from one to six carbon atoms, an alkoxy group having from one to six carbon atoms, or a halogen-substituted alkyl group; R5, R6, R7 and R8 each independently represent an alkyl group having from one to six carbon atoms, an aryl group, or a halogen-substituted alkyl group having from one to six carbon atoms; wherein R9 represents (R10)2O or (R10)3N;
wherein R10 represents H or an alkyl group having from one to eight carbon atoms; and wherein R11 represents H, an alkyl group having from one to eight carbon atoms, a benzyl group or an aralkyl group.
11. The method of generating a reactive species of Claim 10, wherein the photoinitiator comprises:

12. The method of generating a reactive species of Claim 10, wherein the photoinitiator is associated with one or more counterions.
13. The method of generating a reactive species of Claim 12, wherein the one or more counterions comprise tetraphenylboron, tetrachloroboron, tetrafluoroboron, hexafluorophosphate, perchlorate, or a combination thereof.
14. The method of generating a reactive species of Claim 13, wherein the one or more counterions comprise tetraphenylboron or tetrafluoroboron.
15. The method of generating a reactive species of Claim 12, wherein the photoinitiator and the one or more counterions comprise
16. A photoreactive composition comprising at least one photoinitiator and at least one counterion, wherein the composition is capable of generating at least one cationic free radical and at least one nitrogen radical species.
17. The photoreactive composition of Claim 16, wherein the photoinitiator having the general formula:

wherein Z each independently represent wherein R1, R2, R3 and R4 each independently represent hydrogen, an alkyl group having from one to six carbon atoms, an alkoxy group having from one to six carbon atoms, or a halogen-substituted alkyl group; R5, R6, R7 and R8 each independently represent an alkyl group having from one to six carbon atoms, an aryl group, or a halogen-substituted alkyl group having from one to six carbon atoms; wherein R9 represents (R10)2O or (R10)3N;
wherein R10 represents H or an alkyl group having from one to eight carbon atoms; and wherein R11 represents H, an alkyl group having from one to eight carbon atoms, a benzyl group or an aralkyl group.
18. The photoreactive composition of Claim 16, wherein the photoinitiator comprises:

19. The photoreactive composition of Claim 16, wherein the at least one counterion comprises tetraphenylboron, tetrachloroboron, tetrafluoroboron, hexafluorophosphate, perchlorate, or a combination thereof.
20. The photoreactive composition of Claim 16, wherein the composition comprises
CA2412607A 2000-06-19 2001-06-19 Novel photoinitiators and applications therefor Expired - Fee Related CA2412607C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US21242800P 2000-06-19 2000-06-19
US60/212,428 2000-06-19
PCT/US2001/019525 WO2002000735A1 (en) 2000-06-19 2001-06-19 Novel photoinitiators and applications therefor

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CA2412607A1 true CA2412607A1 (en) 2002-01-03
CA2412607C CA2412607C (en) 2010-12-21

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US (1) US6486227B2 (en)
EP (1) EP1297022B1 (en)
JP (1) JP2004501987A (en)
KR (1) KR100772772B1 (en)
AT (1) ATE333471T1 (en)
AU (1) AU2001269905A1 (en)
CA (1) CA2412607C (en)
DE (1) DE60121588T2 (en)
MX (1) MXPA02012011A (en)
WO (1) WO2002000735A1 (en)

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