WO2000018750A2 - Chelates comprising chinoid groups as photoinitiators - Google Patents
Chelates comprising chinoid groups as photoinitiators Download PDFInfo
- Publication number
- WO2000018750A2 WO2000018750A2 PCT/US1999/022590 US9922590W WO0018750A2 WO 2000018750 A2 WO2000018750 A2 WO 2000018750A2 US 9922590 W US9922590 W US 9922590W WO 0018750 A2 WO0018750 A2 WO 0018750A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- photoinitiator
- group
- alkyl group
- photoinitiators
- present
- Prior art date
Links
- 230000005855 radiation Effects 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 51
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- 239000000463 material Substances 0.000 claims abstract description 32
- 229910052751 metal Inorganic materials 0.000 claims abstract description 31
- 239000002184 metal Substances 0.000 claims abstract description 31
- 229910052755 nonmetal Inorganic materials 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 22
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 16
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052796 boron Inorganic materials 0.000 claims abstract description 10
- 150000002148 esters Chemical group 0.000 claims abstract description 6
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 6
- 125000001033 ether group Chemical group 0.000 claims abstract description 5
- 150000002466 imines Chemical group 0.000 claims abstract description 5
- 125000000468 ketone group Chemical group 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 150000001768 cations Chemical class 0.000 claims description 13
- 229910052753 mercury Inorganic materials 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 9
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- 150000002843 nonmetals Chemical group 0.000 claims description 8
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- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- 239000012952 cationic photoinitiator Substances 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- 229910052745 lead Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052718 tin Inorganic materials 0.000 claims description 3
- 229910052726 zirconium Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003277 amino group Chemical group 0.000 claims 1
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- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000012632 extractable Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- JUHDUIDUEUEQND-UHFFFAOYSA-N methylium Chemical compound [CH3+] JUHDUIDUEUEQND-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- WTXMTPLATLKWQS-UHFFFAOYSA-N propane Chemical compound CC[CH2+] WTXMTPLATLKWQS-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000005838 radical anions Chemical class 0.000 description 1
- 150000005839 radical cations Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229940080262 sodium tetrachloroaurate Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
Definitions
- the present invention relates to novel photoinitiators and methods for generating a reactive species using the photoinitiators.
- the present invention further relates to methods of polymerizing or photocuring polymerizable material using the above-mentioned photoinitiators.
- the photoinitiators of the present invention find particular utility in photocurable inks as used in ink jet printers or on a printing press with and without nitrogen blanketing.
- polymers have served essential needs in society. For many years, these needs were filled by natural polymers. More recently, synthetic polymers have played an increasingly greater role, particularly since the beginning of the 20th century.
- Especially useful polymers are those prepared by an addition polymerization mechanism, i.e., free radical chain polymerization of unsaturated monomers, and include, by way of example only, coatings and adhesives.
- chain polymerization is initiated by a reactive species, which often is a free radical.
- the source of the free radicals is termed an initiator or photoinitiator. Improvements in free radical chain polymerization have focused both on (1) more reactive monomer and pre- polymer materials and (2) the photoinitiator.
- Whether a particular unsaturated monomer can be converted to a polymer requires structural, thermodynamic, and kinetic feasibility. Even when all three exist, kinetic feasibility is achieved in many cases only with a specific type of photoinitiator. Moreover, the photoinitiator can have a significant effect on reaction rate which, in turn, may determine the commercial success or failure of a particular polymerization process or product.
- a free radical-generating photoinitiator may generate free radicals in several different ways. For example, the thermal, homolytic dissociation of an initiator typically directly yields two free radicals per initiator molecule.
- a photoinitiator i.e., an initiator which absorbs light energy, may produce free radicals by one of three pathways:
- the photoinitiator undergoes excitation by energy absorption with subsequent decomposition into one or more radicals
- the photoinitiator undergoes excitation and the excited species interacts with a second compound (by either energy transfer or a redox reaction) to form free radicals from the latter and /or former compound(s); or (3) the photoinitiator undergoes an electron transfer to produce a radical cation and a radical anion.
- photoinitiators including IRGACURE® 369
- IRGACURE® 369 are presently used in ink compositions to accelerate ink drying in " radiation-drying printing."
- radiation-drying prmting refers to any printing method which utilizes radiation as a drying means. Radiation-drying printing includes, for example, off-set prmting operations, such as on a Heidelberg press, flexographic printing, and flat-bed printing.
- Commercially available photoinitiator systems have a number of shortcomings. First, most of the commercially available photoinitiator systems require a relatively large amount of photoinitiator in the ink composition to fully cure/dry the ink composition. This leads to undesirable extractables within the ink composition.
- X is a conjugated system such as one or more aryl groups or substituted aryl groups
- z is -O, -S, an alkyl group having from one to six carbon atoms, an ester moiety, a ketone moiety, an amine moiety, an imine moiety, an ether moiety, an aryl or substituted aryl group, a metal or non- metal, or a metal or non-metal containing group, such as a zinc-containing group or a boron-containing group, respectively
- M 1 is an alkyl group, a substituted alkyl group, or forms a five-member ring with Z
- the present invention is directed to the above- described photoinitiators, compositions containing the same, and methods for generating a reactive species which includes providing one or more of the photoinitiators and irradiating the one or more photoinitiators.
- One of the main advantages of the photoinitiators of the present invention is that they efficiently generate one or more reactive species under extremely low energy lamps, such as excimer lamps and mercury lamps, as compared to prior art photoinitiators.
- the photoinitiators of the present invention also efficiently generate one or more reactive species in air or in a nitrogen atmosphere. Unlike many prior photoinitiators, the photoinitiators of the present invention are not sensitive to oxygen.
- the photoinitiators of the present invention are as much as ten times faster than the best prior art photoinitiators.
- the present invention is further directed to a method of efficiently generating a reactive species by matching a photoinitiator having an absorption maximum to an emission band of a radiation source, which corresponds to the absorption maximum. By adjusting the substituents of the photoinitiator, one can shift the absorption maximum of the photoinitiator from less than about 222 nm to greater than 445 nm.
- the present invention is also directed to methods of using the above-described photoinitiators to polymerize and/or photocure a polymerizable material.
- the photoinitiators of the present invention result in rapid curing times in comparison to the curing times of prior art photoinitiators, even with relatively low output lamps.
- the present invention includes a method of polymerizing an polymerizable material by exposing the polymerizable material to radiation in the presence of the efficacious wavelength specific photoinitiator composition described above. When an unsaturated oligomer/monomer mixture is employed, curing is accomplished.
- the present invention further includes a film and a method for producing a film, by drawing an admixture of polymerizable material and one or more photoinitiators of the present invention, into a film and irradiating the film with an amount of radiation sufficient to polymerize the composition.
- the admixture may be drawn into a film on a nonwoven web or on a fiber, thereby providing a polymer- coated nonwoven web or fiber, and a method for producing the same.
- the present invention is also directed to an adhesive composition comprising a polymerizable material admixed with one or more photoinitiators of the present invention.
- the present invention includes a laminated structure comprising at least two layers bonded together with the above-described adhesive composition, in which at least one layer is a nonwoven web or film. Accordingly, the present invention provides a method of laminating a structure wherein a structure having at least two layers with the above-described adhesive composition between the layers is irradiated to polymerize the adhesive composition.
- the present invention is further directed to a method of printing, wherein the method comprises incorporating one or more photoinitiators of the present invention into an ink composition; printing the ink onto a substrate; and drying the ink with a source of radiation.
- the present invention is directed to energy-efficient, reactive, photoinitiators and methods for utilizing the same. More particularly, the present invention is directed to new photoinitiators having the following general formula:
- X comprises a conjugated system such as one or more aryl groups or substituted aryl groups
- Z is -O, -S, an alkyl group having from one to six carbon atoms, an ester moiety, a ketone moiety, an amine moiety, an imine moiety, an ether moiety, an aryl or substituted aryl group, a metal or non-metal, or a metal or non-metal containing group, such as a zinc-containing group or a boron-containing group, respectively
- M comprises an alkyl group, a substituted alkyl group, or forms a five-member ring with Z x .
- the present invention is further directed to a method of efficiently generating a reactive species by matching a photoinitiator having an absorption maximum to an emission band of a radiation source, which corresponds to the absorption maximum.
- a photoinitiator having an absorption maximum to an emission band of a radiation source, which corresponds to the absorption maximum.
- the present invention also includes a method of polymerizing a polymerizable material by exposing the polymerizable material to electromagnetic radiation in the presence of one or more of the photoinitiators described above. Further, the present invention is directed to a film and a method for producing a film, by drawing an admixture of polymerizable material and one or more of the photoinitiators described above, into a film and irradiating the film with an amount of electromagnetic radiation sufficient to polymerize the admixture.
- the present invention is further directed to an adhesive composition comprising a polymerizable material admixed and one or more photoinitiators of the present invention.
- the present invention includes a laminated structure comprising at least two layers bonded together with the above-described adhesive composition.
- the present invention further provides a method of laminating a structure wherein a structure having at least two layers with the above-described adhesive composition between the layers is irradiated with appropriate electromagnetic radiation to polymerize the adhesive composition.
- reactive species is used herein to mean any chemically reactive species including, but not limited to, free-radicals, cations, anions, nitrenes, and carbenes. Illustrated below are examples of several of such species.
- carbenes include, for example, methylene or carbene, dichlorocarbene, diphenylcarbene, alkylcarbonyl-carbenes, siloxycarbenes, and dicarbenes.
- nitrenes include, also by way of example, nitrene, alkyl nitrenes, and aryl nitrenes.
- Cations include, by way of illustration, a proton; primary, secondary, and tertiary alkyl carbocations, such as methyl cation, ethyl cation, propyl cation, f-butyl cation, f-pentyl cation, -hexyl cation; allylic cations; benzylic cations; aryl cations, such as triphenyl cation; cyclopropylmethyl cations; methoxymethyl cation; triarylsulphonium cations; and acyl cations.
- Cations also include those formed from various metal salts, such as tetra- ⁇ -butylammonium tetrahaloaurate(III) salts; sodium tetrachloroaurate(III); vanadium tetrachloride; and silver, copper(I) and (II), and thallium(I) triflates.
- metal salts such as tetra- ⁇ -butylammonium tetrahaloaurate(III) salts; sodium tetrachloroaurate(III); vanadium tetrachloride; and silver, copper(I) and (II), and thallium(I) triflates.
- anions include, by way of example, alkyl anions, such as ethyl anion, n-propyl anion, isobutyl anion, and neopentyl anion; cycloalkyl anions, such as cyclopropyl anion, cyclobutyl anion, and cyclopentyl anion; allylic anions; benzylic anions; aryl cations; and sulfur- or phosphorus-containing alkyl anions.
- alkyl anions such as ethyl anion, n-propyl anion, isobutyl anion, and neopentyl anion
- cycloalkyl anions such as cyclopropyl anion, cyclobutyl anion, and cyclopentyl anion
- allylic anions such as cyclopropyl anion, cyclobutyl anion, and cyclopentyl anion
- benzylic anions
- organometallic photoinitiators include titanocenes, fluorinated diaryltitanocenes, iron arene complexes, manganese decacarbonyl, and methylcyclopentadienyl manganese tricarbonyl.
- Organometallic photoinitiators generally produce free radicals or cations.
- quantum yield is used herein to indicate the efficiency of a photochemical process. More particularly quantum yield is a measure of the probability that a particular molecule will absorb a quantum of light during its interaction with a photon. The term expresses the number of photochemical events per photon absorbed.
- quantum yields may vary from zero (no absorption) to 1.
- polymerization is used herein to mean the combining, e.g. covalent bonding, of a number of smaller molecules, such as monomers, to form large molecules, i.e., macromolecules or polymers.
- the monomers may be combined to form only linear macromolecules or they may be combined to form three-dimensional macromolecules, commonly referred to as crosslinked polymers.
- curing means the polymerization of functional oligomers and monomers, or even polymers, into a crosslinked polymer network.
- curing is the polymerization of unsaturated monomers or oligomers in the presence of crosslinking agents.
- unsaturated monomer “functional oligomer”
- crosslinking agent is used herein with their usual meanings and are well understood by those having ordinary skill in the art. The singular form of each is intended to include both the singular and the plural, i.e., one or more of each respective material.
- unsaturated polymerizable material is meant to include any unsaturated material capable of undergoing polymerization.
- the term encompasses unsaturated monomers, oligomers, and crosslinking agents.
- the singular form of the term is intended to include both the singular and the plural.
- the term "fiber” as used herein denotes a threadlike structure.
- the fibers used in the present invention may be any fibers known in the art.
- the term "nonwoven web” as used herein denotes a web-like matter comprised of one or more overlapping or interconnected fibers in a nonwoven manner. It is to be understood that any nonwoven fibers known in the art may be used in the present invention.
- the present invention is directed to new photoinitiators having the following general formula:
- X is a conjugated system such as one or more aryl groups or substituted aryl groups; 7 is -O, -S, an alkyl group having from one to six carbon atoms, an ester moiety, a ketone moiety, an amine moiety, an imine moiety, an ether moiety, an aryl or substituted aryl group, a metal or non- metal, or a metal or non-metal containing group, such as a zinc-containing group or a boron-containing group, respectively; and M 1 is an alkyl group, a substituted alkyl group, or forms a five-member ring with Z .
- X t comprises
- R 6 and R 7 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; and wherein y 1 and y 2 each independently represent a hydrogen, an alkyl group having from one to six carbon atoms, an aryl group,
- X 3 represents a hydrogen, an alkyl or substituted alkyl group, or an aryl or substituted aryl group.
- Other suitable X x groups include, but are not limited to, the following:
- R 6 and R 7 each independently represent a methyl group, an ethyl group, an isopropyl group, a methoxy group, an ethoxy group, or a trifluoromethyl group.
- M ⁇ comprises a tertiary alkyl group having the following formula:
- y 3 , y 4 and y 5 each independently represent a hydrogen, an alkyl group having from one to six carbon atoms, a tertiary amine group, an aryl group, or a substituted aryl group.
- the photoinitiator has the following structure:
- a calcium ion forms a five member ring, which includes the oxygen atom ("Z ') and the electron-rich nitrogen atom.
- Z ' oxygen atom
- an arrow represents a coordinate covalent bond between an electron- rich nitrogen atom and a metal or non-metal cation.
- Other suitable cations include, but are not limited to, beryllium, magnesium, strontium, barium, zinc, aluminum, and copper (II).
- z in the above-described general formula comprises an ester moiety.
- photoinitiators include, but are not limited to, photoinitiators having the following structure:
- the -C(0)CH 3 group (“Z,") may be substituted with other groups including, but not limited to, -CH 3 , -BF 3 and phenyl groups.
- the photoinitiators of the present invention have the following general formula:
- X ⁇ is as defined above;
- Z 2 is a metal or non-metal cation, such as Zn 2+ , Ca 2+ , or boron, or a salt thereof, or -C(0)R, which forms a covalent bond with the oxygen atom;
- R, R l R 2 , R 3 , and R 4 are each independently a hydrogen atom, an alkyl or substituted alkyl group, or an aryl or substituted aryl group.
- R x and R 2 may form one or more aromatic rings with X
- Photoinitiators having the above formula include, but are not limited to, the following photoinitiators:
- R ⁇ , R 12 , R ⁇ 3 , and R 14 are each independently a hydrogen atom; an alkyl group or substituted alkyl group.
- the photoinitiator has the following structure:
- the photoinitiator has the following structure:
- the calcium atom forms a five member ring, which includes the oxygen atom and the electron-rich nitrogen atom.
- other salts may be used instead of the calcium chloride.
- suitable salts include, but are not limited to, salts containing beryllium, magnesium, strontium, barium, zinc, aluminum, scandium, and copper (II).
- another photoinitiator of the present invention may have the following structure:
- R R 2 , and X of the above-described general formula form one or more aromatic rings to form a photoinitiator having the structure below:
- Z 2 , R 3 , and R 4 are substituents as defined above and y u and y 12 are each independently represent a hydrogen; an alkyl group having from one to six carbon atoms; an aryl group;
- the present invention is further directed to novel photoinitiators having the following general formula:
- Y is -O- or -N(R 5 )-; ⁇ is a metal or nonmetal cation or a salt containing the cation; and X l7 R lr R 2 , R 3 , R 4 , and R 5 are as defined above.
- Suitable Z 3 groups include, but are not limited to, metals and metal salts containing Cd, Hg, Zn, Al, Ga, In, Tl, Sc, Ge, Pb, Si, Ti, Sn, and Zr, as well as, nonmetals and nonmetal salts containing boron and phosphorus.
- Z 3 comprises a chloride-containing salt such as zinc chloride, zinc benzyl chloride, or boron chloride.
- "R" comprises hydrogen, a methyl group, an ethyl group, a propyl group, or a benzyl group.
- the photoinitiator has the following structure:
- X 4 comprises any nitrogen-containing group, which donates a pair of electrons to the nitrogen-carbon double bond
- Ri, R 2 , R 3 , R 4/ R 6 , and R 7 are as defined above.
- the above photoinitiator has an absorption maximum of about 360 nm.
- the photoinitiator has the following structure:
- photoinitiators of the present invention have the following structure:
- the photoinitiator has the following structure:
- the absorption maximum of the photoinitiator shifts further to greater than about 410 nm.
- other metal and nonmetal salts may be used in place of the metal and nonmetal chlorides.
- the above photoinitiator may have the following structure:
- the above-described photoinitiators of the present invention may be produced by the following reaction mechanism:
- a first compound reacts with a metal or metal salt or a nonmetal or nonmetal salt, Z 3 , to produce a photoinitiator of the present invention, having a five- member ring containing a metal or nonmetal atom, at least one nitrogen atom, two carbon atoms, and possibly an oxygen atom.
- the photoinitiators have the following general formula:
- X l7 Y, R l7 R 2 , R 3 , R , and R 5 are as defined above;
- Z 4 is a metal or nonmetal atom; and Z 5 and are halogen- containing anions or form one or more rings with or without R 3 or R 4 .
- the nitrogen atom donates its lone electron pair to metal or nonmetal atom, Z 4 , to form a five member ring.
- Suitable , Z 4 groups include, but are not limited to, metals such as Cd,
- Z 4 comprises Cd, Zn, Mg, Ti, boron or phosphorus. More desirably, Z 4 comprises Zn.
- Suitable Z 5 and ⁇ groups include, but are not limited to, halogen- containing anions. Desirably, Z 5 and Z ⁇ each independently comprise fluorine, chlorine or bromine-containing anions. More desirably, Z 5 and Z 6 each independently comprise fluorine-containing anions. Even more desirably, Z 5 and Z 6 each independently comprise BF 4 , AsF 6 , PF 6 , or SbF 6 .
- Ri, R 2 , R 3 , and R 4 each independently comprise hydrogen, a methyl group, an ethyl group, a propyl group, or a benzyl group.
- the photoinitiator has the following structure:
- the photoinitiator has the following structure:
- the photoinitiator of the present invention has the following structure:
- the photoinitiator of the present invention has the following structure:
- the above-described photoinitiators of the present invention may be produced by the following reaction mechanism:
- a first compound reacts with a metal or nonmetal salt, Z 4 Z 5 Z 6 , to produce a photoinitiator of the present invention, having a five-member ring containing a metal or nonmetal atom, at least one nitrogen atom, two carbon atoms, and possibly an oxygen atom.
- the present invention is further directed to novel photoinitiators having the following general structure:
- Y 2 and Y 3 each independently represent -O- or -N(R 3 )(R 4 )-; and X y Ri, R 2 , R 3 , R 4 , Z 4 , Z 5 , and Z ⁇ are as defined above.
- X y Ri, R 2 , R 3 , R 4 , Z 4 , Z 5 , and Z ⁇ are as defined above.
- Y 3 represents -N(R 3 )(R 4 )- £ind Z 5 and Zg form two five member rings: one five member ring which includes Z 4 , Z 5 , and Z 6 , and one five member rings which includes with Z 4 , Z ⁇ 3 and one of R 3 or R 4 .
- the resulting photoinitiator has the following structure:
- Z 5 , Z 6 and R 4 comprise any combination of carbon, nitrogen and oxygen atoms to form two five member rings.
- Z 5 , Z & and R 4 may form two similar ring structures or two different ring structures. Also, each ring formed by Z 5 , Z 6 and R 4 may contain more than five ring members. In one embodiment of the present invention, the resulting photoinitiator has the following structure:
- Xi, Y 2 , R l R 2 , R 3 , and Z 4 are as defined above; and n 2 and n 2 each independently represent an integer from 1 to 5.
- the resulting photoinitiator has the following structure:
- Ri, R , R 3 , R 6 , R 7 , ni, and n 2 are as defined above.
- Z 5 and Z form a single ring.
- the resulting photoinitiator has the following structure:
- Z 5 and Z ⁇ comprise any combination of carbon, nitrogen and oxygen atoms to form a ring.
- Z 5 and Z ⁇ form a five member ring so that the resulting photoinitiator has a dimeric structure.
- One example of the resulting photoinitiator has the following structure:
- photoinitiators of the present invention having the above-described structure include, but are not limited to, the following photoinitiators:
- photoinitiators include, but are not limited to, the following photoinitiators:
- Z 4 comprises boron or zinc in the dimeric structures above.
- Z 4 comprises boron or zinc in the dimeric structures above.
- the resulting photoinitiators are relatively stable at room temperature (from about 15°C to 25°C) and normal room humidity (from about 5% to 60%; desirably from 5% to 30%). However, upon exposure to radiation at an appropriate wavelength, the photoinitiators efficiently produce one or more reactive species.
- the photoinitiators of the present invention have a high intensity of absorption.
- the photoinitiators of the present invention have a molar extinction coefficient (absorptivity) greater than about 20,000 l mole _1 cm- l .
- the photoinitiators of the present invention have a molar extinction coefficient greater than about 25,000 1 mole ⁇ cm "1 .
- the present invention is further directed to a method of generating a reactive species.
- the method of generating a reactive species involves generating a reactive species by exposing one or more of the above-described photoinitiators to radiation. The exposure of the photoinitiators to a radiation source triggers a photochemical process.
- quantum yield is used herein to indicate the efficiency of a photochemical process. More particularly, quantum yield is a measure of the probability that a particular molecule (photoinitiator) will absorb a quantum of light during its interaction with a photon. The term expresses the number of photochemical events per photon absorbed. Thus, quantum yields may vary from zero (no absorption) to 1.
- the photoinitiators of the present invention absorb photons having a relatively specific wavelength and transfers the absorbed energy to one or more excitable portions of the molecule.
- the excitable portion of the molecule absorbs enough energy to cause a bond breakage, which generates one or more reactive species.
- the efficiency with which a reactive species is generated with the photoinitiators of the present invention is significantly greater than that experienced with photoinitiators of the prior art as indicated by faster cure times.
- the photoinitiators of the present invention desirably will have a quantum yield greater than about 0.8. More desirably, the quantum yield of the photoinitiators of the present invention will be greater than about 0.9.
- the quantum yield of the photoinitiators of the present invention will be greater than about 0.95. Still more desirably, the quantum yield of the photoinitiators of the present invention will be greater than about 0.99, with the most desirable quantum yield being about 1.0.
- Exposing the photoinitiators of the present invention to radiation results in the generation of one or more reactive species.
- the photoinitiators may be employed in any situation where reactive species are required, such as for the polymerization of an unsaturated monomer and the curing of an unsaturated oligomer/monomer mixture.
- the unsaturated monomers and oligomers may be any of those known to one having ordinary skill in the art.
- the polymerization and curing media also may contain other materials as desired, such as pigments, extenders, amine synergists, and such other additives as are well known to those having ordinary skill in the art.
- examples of unsaturated monomers and oligomers include ethylene, propylene, vinyl chloride, isobutylene, styrene, isoprene, acrylonitrile, acrylic acid, methacylic acid, ethyl acrylate, methyl methacrylate, vinyl acrylate, allyl methacrylate, tripropylene glycol diacrylate, trimethylol propane ethoxylate acrylate, epoxy acrylates, such as the reaction product of a bisphenol A epoxide with acrylic acid; polyether acrylates, such as the reaction product of acrylic acid with an adipic acid/ hexanediol-based polyether, urethane acrylates, such as the reaction product of hydroxypropyl acrylate with diphenylmethane-4,4'-diisocyanate, and polybutadiene diacrylate oligomer.
- the types of reactions that various reactive species enter into include, but are not limited to, addition reactions, including polymerization reactions; abstraction reactions; rearrangement reactions; elimination reactions, including decarboxylation reactions; oxidation-reduction (redox) reactions; substitution reactions; and conjugation/ deconjugation reactions.
- addition reactions including polymerization reactions; abstraction reactions; rearrangement reactions; elimination reactions, including decarboxylation reactions; oxidation-reduction (redox) reactions; substitution reactions; and conjugation/ deconjugation reactions.
- the present invention also comprehends a method of polymerizing a polymerizable material, such as an unsaturated monomer or epoxy compound, by exposing the polymerizable material to radiation in the presence of the effacious photoinitiators of the present invention described above.
- a polymerizable material such as an unsaturated monomer or epoxy compound
- the polymerizable material admixed with the photoinitiators of the present invention is to be admixed by means known in the art, and that the mixture will be irradiated with an amount of radiation sufficient to polymerize the material.
- the amount of radiation sufficient to polymerize the material is readily determinable by one of ordinary skill in the art, and depends upon the identity and amount of photoinitiators, the identity and amount of the polymerizable material, the intensity and wavelength of the radiation, and the duration of exposure to the radiation.
- one or more photoinitiators of the present invention are used to polymerize an epoxy resin. It is believed that the following reaction mechanism takes place in the presence of a hydrogen-donating compound, such as an alcohol, cumene or amine:
- Reactive species ⁇ Z 1 and/or HZ 2
- an epoxy resin then react with an epoxy resin according to the following mechanism to produce a polyether:
- the weak conjugate bases, Z ⁇ and/or Z 2 ⁇ which are non- nucleophilic, enable the polymerization reaction to take place, unlike other anions, which may prematurely terminate the polymerization reaction.
- the present invention further includes a film and a method for producing a film, by drawing an admixture of a polymerizable material and one or more photoinitiators of the present invention, into a film and irradiating the film with an amount of radiation sufficient to polymerize the composition.
- the polymerizable material is an unsaturated oligomer/monomer mixture
- curing is accomplished. Any film thickness may be produced, as per the thickness of the admixture formed, so long as the admixture sufficiently polymerizes upon exposure to radiation.
- the admixture may be drawn into a film on a nonwoven web or on a fiber, thereby providing a polymer- coated nonwoven web or fiber, and a method for producing the same.
- the present invention also includes an adhesive composition comprising a polymerizable material admixed with one or more photoinitiators of the present invention.
- the present invention includes a laminated structure comprising at least two layers bonded together with the above-described adhesive composition.
- a laminate is produced wherein at least one layer is a cellulosic or polyolefin nonwoven web or film. Accordingly, the present invention provides a method of laminating a structure wherein a structure having at least two layers with the above-described adhesive composition between the layers is irradiated to polymerize the adhesive composition. When the unsaturated polymerizable material in the adhesive is an unsaturated oligomer/monomer mixture, the adhesive is irradiated to cure the composition.
- any layers may be used in the laminates of the present invention, on the condition that at least one of the layers allows sufficient radiation to penetrate through the layer to enable the admixture to polymerize sufficiently.
- any cellulosic or polyolefin nonwoven web or film known in the art may be used as one of the layers so long as they allow radiation to pass through.
- the amount of radiation sufficient to polymerize the admixture is readily determinable by one of ordinary skill in the art, and depends upon the identity and amount of photoinitiator, the identity and amount of the polymerizable material, the thickness of the admixture, the identity and thickness of the layer, the intensity and wavelength of the radiation, and the duration of exposure to the radiation.
- the radiation to which the photoinitiators of the present invention may be exposed generally will have a wavelength of from about 4 to about 1,000 nanometers.
- the radiation may be ultraviolet radiation, including near ultraviolet and far or vacuum ultraviolet radiation; visible radiation; and near infrared radiation.
- the radiation will have a wavelength of from about 100 to about 900 nanometers. More desirably, the radiation will have a wavelength of from about 100 to 700 nanometers.
- the radiation will be ultraviolet radiation having a wavelength of from about 4 to about 400 nanometers. More desirably, the radiation will have a wavelength of from about 100 to about 420 nanometers, and even more desirably will have a wavelength of from 320 to about 420 nanometers.
- the radiation desirably will be incoherent, pulsed ultraviolet radiation from a dielectric barrier discharge excimer lamp or radiation from a mercury lamp.
- Excimers are unstable excited-state molecular complexes which occur only under extreme conditions, such as those temporarily existing in special types of gas discharge. Typical examples are the molecular bonds between two rare gaseous atoms or between a rare gas atom and a halogen atom. Excimer complexes dissociate within less than a microsecond and, while they are dissociating, release their binding energy in the form of ultraviolet radiation.
- the dielectric barrier excimers in general emit in the range of from about 125 ran to about 500 nm, depending upon the excimer gas mixture.
- Dielectric barrier discharge excimer lamps (also referred to hereinafter as “excimer lamp”) are described, for example, by U. Kogelschatz, "Silent discharges for the generation of ultraviolet and vacuum ultraviolet excimer radiation.” Pure & Appl. Chem., 62, No. 9, pp. 16671674 (1990); and E. Eliasson and U. Kogelschatz, "UV Excimer Radiation from Dielectric- Barrier Discharges.” Appl. Phys. B. 46, pp. 299-303 (1988).
- Excimer lamps were developed by ABB Infocom Ltd., Lenzburg, Switzerland, and at the present time are available from Heraeus Noblelight GmbH, Kleinostheim, Germany.
- the excimer lamp emits incoherent, pulsed ultraviolet radiation.
- Such radiation has a relatively narrow bandwidth, i.e., the half width is of the order of approximately 5 to 100 nanometers.
- the radiation will have a half width of the order of approximately 5 to 50 nanometers, and more desirably will have a half width of the order of 5 to 25 nanometers.
- the half width will be of the order of approximately 5 to 15 nanometers.
- the ultraviolet radiation emitted from an excimer lamp can be emitted in a plurality of wavelengths, wherein one or more of the wavelengths within the band are emitted at a maximum intensity. Accordingly, a plot of the wavelengths in the band against the intensity for each wavelength in the band produces a bell curve.
- the "half width" of the range of ultraviolet radiation emitted by an excimer lamp is defined as the width of the bell curve at 50% of the maximum height of the bell curve.
- excimer lamp typically is identified or referred to by the wavelength at which the maximum intensity of the radiation occurs, which convention is followed throughout this specification and the claims.
- excimer lamp radiation is essentially monochromatic.
- excimer lamps are highly desirable for use in the present invention, the source of radiation used with the photoinitiators of the present invention may be any radiation source known to those of ordinary skill in the art.
- a mercury lamp with a D-bulb which produces radiation having an emission peak of about 360 nm is used to produce free radicals from the above-described photoinitiators.
- This radiation source is particularly useful when matched with one or more photoinitiators of the present invention having an absorption maximum of about 360 nanometers, corresponding to the emission peak of the mercury lamp.
- Other specialty doped lamps which emit radiation at about 420 nm, may be used with photoinitiators of the present invention which have an absorption maximum at about 420 nm.
- One lamp, the V-bulb available from Fusion Systems is another suitable lamp for use in the present invention.
- specialty lamps having a specific emission band may be manufactured for use with one or more specific photoinitiators of the present invention.
- New lamp technology provides the following potential advantages:
- the photoinitiators of the present invention As a result of the photoinitiators of the present invention absorbing radiation in the range of about 250 to about 390 nanometers, some of the photoinitiators of the present invention will generate one or more reactive species upon exposure to sunlight. Accordingly, these photoinitiators of the present invention provides a method for the generation of reactive species that does not require the presence of a special light source.
- the photoinitiators of the present invention enable the production of adhesive and coating compositions that consumers can apply to a desired object and polymerize or cure upon exposure to sunlight. These photoinitiators also enable numerous industry applications wherein polymerizable materials may be polymerized merely upon exposure to sunlight. Therefore, depending upon how the photoinitiator is designed, the photoinitiator of the present invention can eliminate the cost of purchasing and maintaining light sources in numerous industries wherein such light sources are necessary without the photoinitiators of the present invention.
- the effective tuning of the photoinitiators of the present invention for a specific wavelength band permits the photoinitiators of the present invention to more efficiently utilize the target radiation in the emission spectrum of the radiating source corresponding to the "tuned" wavelength band, even though the intensity of such radiation may be much lower than, for example, radiation from a narrow band emitter, such as an excimer lamp.
- a narrow band emitter such as an excimer lamp.
- the effectiveness of the photoinitiators of the present invention is not necessarily dependent upon the availability or use of a narrow wavelength band radiation source.
- the above-described photoinitiators of the present invention may be incorporated into ink compositions.
- one or more of the photoinitiators are incorporated into an ink jet ink composition for use on ink jet ink printers.
- the ink composition may be used on commercially available ink jet printing machines alone or in combination with a radiation source in series with the ink jet printing machine for instantaneous curing of the ink jet ink composition.
- Any radiation source known to those of ordinary skill in the art may be used to cure the ink jet ink composition.
- one of the above-described radiation sources is used to cure the ink composition.
- a further use of the above-described photoinitiators of the present invention involves the incorporation of one or more of the photoinitiators into an ink composition for use on a radiation-drying printing press.
- Radiation-drying printing refers to any printing method which utilizes radiation as a drying means. Radiation- drying printing includes, for example, off-set printing operations, such as on a Heidelberg press, flexographic printing, and flat-bed printing.
- the photoinitiators of the present invention enable increased press output due to the photoreactivity of the photoinitiators. Further, the increased output may be obtained while using a minimal amount of photoinitiator and a low energy light source. In one embodiment of the present invention, complete curing at an output rate of 10,000 printed sheets per hour may be obtained using a 50 W cold lamp as the light source.
- the amount of photoinitiator added to the ink composition, adhesive composition or resin is less than about 4.0 wt% of the total weight of the composition. More desirably, the amount of photoinitiator added to the composition is from about 0.25 to about 3.0 wt% of the total weight of the composition. Most desirably, the amount of photoinitiator added to the composition is from about 0.25 to about 2.0 wt% of the total weight of the composition.
- a major advantage of the photoinitiators of the present invention is that they enable rapid curing times of ink compositions, adhesive compositions and/ or resins in comparison to the curing times of prior art photoinitiators.
- Ink compositions containing the photoinitiators of the present invention possess rapid curing times from 5-10 times faster than the curing times of ink compositions containing the best known photoinitiators.
- the use of the photoinitiators of the present invention in ink compositions, adhesive compositions or resins for printing presses enables print speeds, which were at one time thought to be unobtainable.
- the printed sheet output is greater than 6,000 sheets per hour. More desirably, the printed sheet output is greater than 8,000 sheets per hour. Most desirably, the printed sheet output is greater than
- Ciba Geigy photoinitiator 369 (CGI 369) in the form of a powder was added to a 1 g sample of red flexo ink (Gamma Graphics). The mixture was exposed to UV radiation while positioned within an FTIR machine to monitor the decrease in carbon-carbon double bonds within the mixture. The curing rate was measured.
- the mixture was exposed to UV radiation while positioned within an FTIR machine to monitor the decrease in carbon- carbon double bonds within the mixture.
- the curing rate was measured.
- the photoinitiator had a curing rate relative to the CGI 369 photoinitiator of greater than 220%.
- zinc chloride containing water was heated under an argon gas atmosphere to produce zinc chloride free of water.
- Into a 250 ml, three-necked, round- bottom flask fitted with condenser, argon gas inlet, and bubbler outlet was placed 2.6 g ( 0.019 mole) of ZnCl 2 .
- the flask was continuously flushed with argon while the ZnCl 2 was heated with a propane torch.
- the ZnCl 2 was heated for about 15 minutes until it melted. Heating was continued for about ten minutes and then the ZnCl 2 was allowed to cool under an argon atmosphere.
- the product was ground to form a powder, still under an argon atmosphere.
- zinc chloride containing water was heated under an argon gas atmosphere to produce zinc chloride free of water.
- Into a 1 -liter, three-necked flask was placed 7.4 g ( 0.05 mole) of ZnCl 2 .
- the flask was continuously flushed with argon while the ZnCl 2 was heated with a propane torch.
- the ZnCl 2 was heated until it liquified. Heating was continued for about ten minutes and then the ZnCl 2 was allowed to cool.
- the product was ground to form a powder, still under an argon atmosphere.
- the resulting modified-369 compound had the following structure:
- the yellow solid was found to have a similar retention time and UV absorption compared to IRGACURE® 369. However, the cure rate of a resin containing the yellow solid was 3 to 5 times faster than the cure rate of an identical resin containing the IRGACURE® 369 photoinitiator.
- the flask was continuously flushed with argon and cooled in an ice bath. Into the flask was added 38.8 g (0.0275 mole) of boron trifluoride etherate. The reaction was carried out in the dark and stirred at 0°C for about 10 hours.
- Zn-containing photoinitiator Two lots of Zn-containing photoinitiator were prepared as in Examples 2-5 above. The lots were designated Z1029 and Z106. Offset printing trials were performed at the Institute for Surface Modification (Leipzig, Germany) using Gerber Schmidt highly pigmented black ink compositions. The photoinitiator was added to the ink composition and mixed using a high speed vortex mixer. After mixing for about 15 minutes, the temperature was measured to be about 60°C. Similar ink compositions were prepared using IRGACURE® 369.
- a sheet-fed offset press manufactured by Heidelberg Press, Model No. GT052 was used to print sheets using the above ink compositions.
- the press ran up to 8,000 sheets per hour.
- the curing took place in a nitrogen atmosphere or in air.
- the results of the printing test are given below in Table 1.
- photoinitiator systems of the present invention consistently provided better cure than IRGACURE® 369 alone.
- the photoinitiators of the present invention provided good cure results in a nitrogen atmosphere, as well as, in air.
- zinc tetrafluoroborate available from Aldrich
- a vacuum oven (0.01 mm Hg)
- the dried solid and ether were mixed to form a 0.5M solution of zinc tetrafluoroborate in ether.
- IRGACURE® 369 available from Ciba Geigy having the following structure
- Example 15 Into a 1-liter, three-necked round-bottom flask was placed 15.0 g (0.05 mole) of l-(2,6-dimethoxy-4- morpholinophenyl)-2-methylpropan-l-one produced in Example 13 and 150 ml. of glacial acetic acid. Hydrogen bromide gas was bubbled through the mixture for about 40 minutes. The product was then used in the next step, disclosed in Example 15.
- Example 14 Into a 1-liter, three-necked round-bottom flask was placed 19.1 g (0.05 mole) of the product produced in Example 14. The mixture was chilled to 5°C. To the chilled mixture was added dropwise 8.0 g of Br 2 over a period of about one hour. The mixture was then stirred for about one hour. The solvent was removed under vacuum to yield a pale yellow /orange solid. The yield of the final product was 20.9 g of product (92%).
- a sample containing 0.1 g of the photoinitiator produced in Example 19 and 1.0 g of a red flexographic resin was prepared. A drop of the resin sample was drawn down on a white panel. The thin film was exposed to a 50W excimer lamp (308 nm). The resin fully cured after 4 flashes
Priority Applications (9)
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CA002353685A CA2353685A1 (en) | 1998-09-28 | 1999-09-28 | Chelates comprising chinoid groups as photoinitiators |
PL99366326A PL366326A1 (en) | 1998-09-28 | 1999-09-28 | Novel photoinitiators and applications therefor |
SK417-2001A SK4172001A3 (en) | 1998-09-28 | 1999-09-28 | Chelates comprising chinoid groups as photoinitiators |
ES99956500T ES2263291T3 (es) | 1998-09-28 | 1999-09-28 | Quelatos que comprenden grupos quinoides como fotoiniciadores. |
JP2000572210A JP2003533548A (ja) | 1998-09-28 | 1999-09-28 | 光重合開始剤であるキノイド基を含むキレート |
BRPI9914123-0A BR9914123B1 (pt) | 1998-09-28 | 1999-09-28 | fotoiniciadores e aplicações para os mesmos. |
AU13098/00A AU1309800A (en) | 1998-09-28 | 1999-09-28 | Novel photoinitiators and applications therefor |
EP99956500A EP1117698B1 (en) | 1998-09-28 | 1999-09-28 | Chelates comprising chinoid groups as photoinitiators |
DE69930948T DE69930948T2 (de) | 1998-09-28 | 1999-09-28 | Chelate mit chinoiden gruppen als photoinitiatoren |
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JP2003533548A (ja) | 2003-11-11 |
EP1117698A2 (en) | 2001-07-25 |
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BR9914123A (pt) | 2002-06-18 |
WO2000018750A9 (en) | 2001-07-26 |
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EP1117698B1 (en) | 2006-04-19 |
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ATE323725T1 (de) | 2006-05-15 |
WO2000018750A8 (en) | 2000-09-28 |
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