CN1222163A - Photoactive compounds for use with narrow wavelength band ultraviolet (UV) curing systems - Google Patents
Photoactive compounds for use with narrow wavelength band ultraviolet (UV) curing systems Download PDFInfo
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Abstract
Novel substituted diaryl ketones, photopolymerization compositions including the compounds, 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 ultraviolet light using conventional techniques and radiation sources to give greatly improved cure speeds. The compounds of the invention also show a significantly elevated level of reactivity at a narrow wavelength band, with a peak emission wavelength at or near 308 nm. Because of the increased level of activity, the photoinitiator can be used in considerably lower amounts.
Description
The present invention relates generally to new Photoactive compounds with and application and method for making.More particularly, the present invention relates to the diaryl ketone that replaces and be used for the photoactivation paradigmatic system.
Alefinically unsaturated compounds, especially acrylate derivative can polymerizations under the uviolizing of using 200-450 millimicron wavelength in the presence of the light-initiated system of bimolecular.Light-initiated system generally comprises (1) diaryl ketone light trigger and (2) coinitiator or synergist, promptly gives the molecule of body as hydrogen atom.Coinitiator or synergist generally are alcohol, tertiary amine or have ether with the hydrogen that links to each other adjacent to heteroatomic carbon atom.
The diaryl ketone light trigger that is used for the light-initiated system of bimolecular that can buy on the market includes benzophenone, 2,4-dimethyl benzophenone, isopropyl thioxanthone and 2,4-diethyl thioxanthone.Yet the ultra-violet absorption spectrum separately of these light triggers can not be effectively be complementary with the ultraviolet emission spectrum of the commercially available mercuryvapour bulb of standard.
Therefore, coml ultraviolet curing process may add quite a large amount of initiators and synergist in prescription.This may make the solidified product contain a large amount of residual light initiator and synergist, and this can make the performance of photostabilization and resistance to oxidation degraded reduce again.In addition, Can Yu light trigger and synergist can extract or wash out or move to the surface of product from the solidified product.Because the remaining light trigger and the existence of synergist, the physical properties of product can reduce manyfold.
The invention provides the diaryl ketone of the photopolymerisable new replacement that is used for alefinically unsaturated compounds.New compound of the present invention is specially adapted to make the acrylate derivative photopolymerization under the uviolizing with wavelength 200-450 millimicron in the presence of coinitiator or the synergist.The present invention also provides the photopolymerization system, and this system comprises the method for using compound of the present invention as the of the present invention new diaryl ketone compound of its composition and in the photopolymerization system.
Some characteristic of the present invention and advantage were mentioned, other can and obviously see in the accompanying drawing from being described in detail subsequently, wherein:
Fig. 1 illustrates United States Patent (USP) 5,504, the ultraviolet emission spectrum of the exciter lamp of narration in 391;
Fig. 2 illustrates the ultra-violet absorption spectrum of 4,4 ＇-two (4-sec.-propyl phenoxy group) benzophenone;
Fig. 3 illustrates the ultra-violet absorption spectrum of 4,4 ＇-two (phenoxy group) benzophenone;
Fig. 4 illustrates the ultra-violet absorption spectrum of 4-(N-morpholino) benzophenone;
Fig. 5 illustrates the ultra-violet absorption spectrum of 4,4 ＇-two (2,4-two-tert-pentyl phenoxy group) benzophenone.
The preferred diaryl ketone of the present invention is suitably to replace, to have the ultraviolet spectra of obvious absorption band at the 250-350 millimicron, more preferably at the 290-325 millimicron. Noval chemical compound of the present invention comprises the biaryl compound of the replacement of following general formula (I):In the formula: A is-CO-or-CO-CO-;
Z is (H, H) ,-CH2-、-S-、-O-、-CO-、-NR
9-or connect the key of two aromatic rings, namely
R
1And R
2Be independent of each other, be selected from H,
In the formula, W=2-6
In the formula, X is 4-5
And
X-R
7：
X is O or S;
R
3, R
4, R
5And R
6Be independent of each other, be selected from-H ,-Cl ,-Br ,-NO
2,-CN ,-OH, C
1-C
8Alkyl, C
6-C
8Aryl, C
7-C
24Alkaryl or aralkyl, C
1-C
8Alkoxyl group, C
6-C
18Aryloxy, C
7-C
24Alkyl-aryloxy or alkoxy aryl, C
1-C
8Alkyl thioether ,-COOH and-COOR
7And
R
7, R
8And R
9Be selected from C with being independent of each other
1-C
8Alkyl and C
7-C
24Alkaryl or aralkyl.
The exemplary compounds of general molecular formula I includes but not limited to 4,4 ＇-two (4-sec.-propyl phenoxy group) benzophenone, 4,4 ＇-two (phenoxy group) benzophenone, 4-(N-morpholino) benzophenone and 4,4 ＇-two (2,4-two tert-pentyl phenoxy groups) benzophenone.
In general, the compound of logical formula I can be with having known preparation 4,4 ＇-dibasic diaryl ketone now, the method for 4,4 ＇-two phenoxy group benzophenone and other substituted diphenylamine oxygen base-benzophenone preparation specifically.These methods are known in open source literature and patent documentation.For example, the method for Crochemore (French Patent 2,617,160) is to make phenyl ether with the phenoxy benzoic acid reaction that replaces at about 50 ℃ in liquid HF.The method of Towle (European patent 262,919) is to make phenyl ether obtain the product of higher isomer purity with the phenoxy group Benzoyl chloride reaction that replaces in the presence of Friedel-Crafts catalyzer and proton control agent in chlorinated solvents.The method of Keller (United States Patent (USP) 3,366,691) is to make the same AlCl of phenyl ether under about 80 ℃
3Photoreactive gas prepared in reaction two phenoxy group benzophenone.People's such as Janson (United States Patent (USP) 4,843,179) method is under temperature about 148 ℃ and pressure phenyl ether and carbonic acid gas to be reacted in the presence of promotor such as the phosphoryl chloride.Above-mentioned Crochemore, Towle, the method for Keller and Janson is fully incorporated in this.
In another specific embodiments of the present invention, provide to comprise the photopolymerizable composition of above-mentioned logical formula I compound as light trigger.Photopolymerisable composition that staff used at this and that be familiar with understands is meant and is exposed to sclerosis or cured compositions under the radiation.
In general, composition of the present invention comprises alefinically unsaturated compounds, comprise monomer, oligopolymer, polymkeric substance, prepolymer, resin material and their mixture, these materials are optional disperse or be dissolved under being exposed to the uviolizing source can The suitable solvent with its copolymerization in.As be familiar with the staff and understand, these photopolymerization compounds or simple function group, or can in each molecule, comprise the polymerisable ethylenically unsaturated group of two or more ends.
Typical photopolymerisable compound or precursor include but not limited to reaction-ity ethylene base monomer, comprise Acrylic Acid Monomer, as vinylformic acid and methacrylic acid and their acid amides, ester, salt and corresponding nitrile.Suitable vinyl monomer includes but not limited to methyl acrylate, ethyl propenoate, vinylformic acid just or the tert-butyl ester, Isooctyl acrylate monomer, methyl methacrylate, Jia Jibingxisuanyizhi, methacrylic acid 2-ethylhexyl, butyl acrylate, Propenoic acid, 2-methyl, isobutyl ester, corresponding hydroxy acrylate, hydroxyl acrylic ethyl ester for example, the hydroxyl acrylic propyl ester, the hydroxymethyl EHA, the vinylformic acid diol ester, Ethylene glycol dimethacrylate for example, dimethacrylate hexylene glycol ester, allyl acrylate, allyl methacrylate(AMA) for example, the methacrylic diallyl phthalate, acrylic acid epoxy ester, for example, glycidyl methacrylate, and acrylic-amino plastics, for example acrylic melamine ester.Other vinyl acetate between to for plastic base ester, halogen ethene and vinylidene halide and acid amides, for example Methacrylamide, acrylamide, diacetone acrylamide, divinyl, vinylbenzene, Vinyl toluene etc. in addition.Prepolymer comprises epoxide, polyester and the urethane of acrylated, is generally control viscosity and mixes use with suitable monomer.Photopolymerization compounds can polymerization forms homopolymer or with other different monomer copolymerization.
The content of light trigger is enough to cause the polymerization of photopolymerization compounds wherein under uviolizing in photopolymerizable composition.An advantage of compound of the present invention is that the amount of comparing used initiator with traditional light trigger will be lacked.This composition can contain the light trigger of the 0.001-10% weight that accounts for the photopolymerization compounds gross weight, preferably about 0.005-0.10%.
Also may be an advantage be that a composition as composition also has coinitiator or synergist, promptly give the molecule of body as hydrogen atom.Coinitiator or synergist are known in the present technique field, are generally alcohol, tertiary amine or ether, have hydrogen to be connected in the carbon atom adjacent with heteroatoms on it.The general content of these coinitiators accounts for about 0.2-25% of composition total weight.Suitable compounds comprises the ester of trolamine, methyl-diethanolamine (MDEA), ethyldiethanolamine and dimethylaminobenzoic acid.These compounds can increase the efficient and the speed of polymerization process as the coinitiator or the accelerator of key light initiator.
In addition, photopolymerizable composition can contain polymerization starter, filler, uv-absorbing agent and organo-peroxide.
This photopolymerizable composition can impose on traditional method and apparatus or be deposited on the surface of matrix.This composition spreads as successive film basically or with discontinuous pattern.Composition of the present invention generally is a fluid under common service temperature (room temperature-Yue 60 ℃).
The sedimentary thickness of this composition depends on the desired thickness of the solidifying product that obtains and becomes.It is that about 1 micron-5 mil is advisable with the thickness that solidified coating is provided that this composition is put on matrix surface with capacity.
Usually, matrix is coated with uncured photopolymerizable composition, uses the travelling belt that moves at a predetermined velocity then by the ultraviolet ray of light beam is provided.The matrix that is coated with can be, for example, and metal, timber, mineral, glass, paper, plastics, fabric, pottery etc.
Being used for activation beam of the present invention can be visible light or ultraviolet ray, or existing visible light also has UV-light in its spectrum.Any known method that ultraviolet radiation is provided in the present technique field can be used, for example, the polymerization activation can be made with the ultraviolet radiation composition in the ultraviolet radiation of 200-450 millimicron.Radiation can be natural or artificial, and is unicolor or pleochroic, incoherent or relevant, and intensity is enough to make light trigger activation of the present invention and carries out polymerization.Traditional source of radiation includes the lamp and the electric arc lamp of luminescent lamp, mercury lamp, interpolation metal.Coherent source is nitrogen, helium, argon ion and the Ionized Ne laser of pulse, and their emmission spectrum is positioned within the ultraviolet of The compounds of this invention or the visible absorption frequency band or overlaid.
As mentioned above, diaryl ketone of the present invention is preferably suitably replaced, and makes its UV spectrum with tangible 250-350 millimicron absorption band, particularly 290-325 millimicron.Therefore, this compound can be with the narrow wavelength band that is known as exciter lamp, high pressure ultra-violet curing light irradiation, this light fixture has spectrum 250-350 millimicron scope, particularly peak emission wavelength or near 308 millimicrons, as at United States Patent (USP) 5, discuss in 504,391, this patent documentation is fully incorporated in this.The compound of logical formula I shows quite high reactive behavior at these wavelength.Because active increasing, this light trigger consumption can reduce greatly.
During polymerization, this composition can provide the product of essentially no adhesion, the anti-general processing of this product under being exposed to uv-radiation.This composition can be used in the application of any kind in the known photopolymerization field, comprises that the solid tackiness agent is to make products such as coating, paint, enamel, lacquer, tinting material or printing ink.This composition is specially adapted to make the photopolymerization top coat of printing process, as planography, screen printing etc.
The present invention will further be illustrated with following non-limiting example.
Synthesizing of 4,4 ＇-dibromo benzophenone
4,4 ＇-dibromo benzophenone is a kind of tuning (tuned) light trigger precursor, can be by the normal-temperature reaction preparation of right under Aluminum chloride anhydrous catalysis-bromobenzene formyl chloride and bromobenzene.This method for making, was discussed in the 2537-2549 page or leaf at Canadian Journal of Chemistry (Can.J.Chem.) 58,1980 by W.J.Leigh etc.
3,6-dibromo anthrone synthetic
3,6-dibromo anthrone is a kind of tuned light initiator precursor, can be at first obtain 2 by anthraquinone under about 160 ℃ and pressure with the direct bromination of elemental bromine, the 7-dibromo-anthraquinone, and as Diehl, chemistry report (Chem.Ber.) is discussed for 11,1878,181 pages.Then, dibromo-anthraquinone is become 3 with aluminum metal with sulfate reduction, 6-dibromo anthrone, as R.Biehl etc. in JACS (J.Amer.Chem.Soc.) 99 (13), 1977, discuss among the 4278-4286.
Embodiment 3
2,7-dibromo xanthone synthetic
2,7-dibromo xanthone is a kind of tuned light initiator precursor, can and make catalyzer with trace iodine under about 100 ℃ in acetic acid and directly the xanthone bromination be made with elemental bromine.As by P.R.J.Gaffney etc. in Englishize association will, Perkin collection of thesis (J.Chem.Soc., Perkin Trans.) 1,1991 (6) is discussed in the 1355-1360 page or leaf.
2,7-dibromo xanthone can also be by making the phosgenation of 4,4 ＇-two bromo-phenyl ether with aluminum chloride as catalyzer.This method is at United States Patent (USP) 2,776, once discusses in 299.
Embodiment 4
Synthesizing of the amino thio-xanthene-one of 2-
Be dissolved in thiosalicylic acid (6 gram) in 200 grams, 98% sulfuric acid and be chilled to 5 ℃ 16 hours, be added in the frozen water suddenly then.To precipitate with the 5% caustic soda aqueous solution and stir 2 hours, and filter, and wash with water.Acetonitrile/acetone of 50/50 stirs to remove unreacted Acetanilide together then.The product that obtains hydrolysis 8 hours in the sulfuric acid 70% under 80-105 ℃ obtains the amino thio-xanthene-one of tuning light trigger precursor 2-, fusing point 227-229 ℃ after neutralization, washing and drying.Its structure is confirmed by IR, NMR, C-13 NMR and MS.
Embodiment 5
Synthesizing of 2-morpholino thio-xanthene-one
With the amino thio-xanthene-one of 2-(4.9 gram), Anhydrous potassium carbonate (4.5 gram) and two (ethylene glycol) Anaesthetie Ether (150 milliliters) reflux (180 ℃), add 5.2 gram dibromo ethyl ethers.To react maintenance and reflux 24 hours, filtered while hot is removed under vacuum and is desolvated.With resistates recrystallization in acetone, obtain 2-morpholino thio-xanthene-one, fusing point 166-167 ℃.Its structure is confirmed by IR, NMR, C-13 NMR and MS.
Embodiment 6
Synthesizing of Michler's keton type compound
Michler's keton type compound, as right, right-two cyclobutyl Uvinul A Pluss, N-benzyl ring butylamine that can be by making about 4.3 molar equivalents under 24 ℃ forms 4-cyclobutyl amino-Benzoyl chloride with the phosgene reaction of 1 molar equivalent.Then, add ZnCl
2Finish reaction and obtain desired compound.This method is at United States Patent (USP) 2,882, discusses in 472.
Embodiment 7
Synthesizing of 4,4 ＇-two (4-sec.-propyl phenoxy group) benzophenone
In the solution of 30 milliliters of dimethyl formamides, slowly be added in mineral oil (6.0 gram) sodium hydride 60% at 4-isopropyl-phenol (20.4 gram) and be dissolved in the slurry of 150 milliliters of dimethyl formamides.After reaction is finished, add 8.5 gram 4,4 ＇-dibromo benzophenone and 1.0 gram dendroid copper powders, the reaction mixture reflux is also kept refluxing 24 hours, under vacuum, boil off solvent, in resistates impouring frozen water.With crude product recrystallization in ethanol, obtain desired compound, fusing point 104-105 ℃.Its structure is confirmed by IR, NMR, C-13NMR and MS.
Embodiment 8
4,4 ＇-two (2,4-two (1, the 1-dimethyl propyl) phenoxy group benzophenone synthetic
Identical with the method for embodiment 7, but replace the 4-isopropyl-phenol with two-tert.-amyl phenol.Behind recrystallization from ethanol, obtain the compound that requires, fusing point 54-56 ℃.Its structure is confirmed by IR, NMR, C-13NMR and MS.
Embodiment 9
Synthesizing of 4-morpholino benzophenone
4-morpholino benzophenone is buied by Aldrich Chemical Co. in market.
Embodiment 10
Synthesizing of 4,4 ＇-two phenoxy group benzophenone
4,4 ＇-two phenoxy group benzophenone can be by as catalyzer phenyl ether being made with aluminum chloride in about 3 hours with phosgene reaction under the pressure of 80 ℃ and 45 pounds/square inch.The fusing point of the product that obtains is 146-147 ℃.This method is at United States Patent (USP) 3,366, discusses in 691.We are by having prepared 4,4 ＇-two phenoxy group benzophenone with embodiment 7 preparation 4,4 ＇-two (4-sec.-propyl phenoxy group) methods that benzophenone is identical, and different is to replace the 4-isopropyl-phenol with phenol.The fusing point of product compound is consistent with the document record, and its structure is confirmed by IR, NMR, C-13NMR and MS.
Embodiment 11
3,6-two phenoxy group anthracyclinone derivatives synthetic
With 3,6-dibromo anthrone is a raw material, and two phenoxy group anthracyclinone derivatives can prepare with embodiment 7 identical methods, but with 3,6-dibromo anthrone replaces 4,4 ＇-dibromo benzophenone, replaces the 4-isopropyl-phenol with suitable phenol.
Embodiment 12
The merchant who is sold by the 501 UCB Radcure that restrain is called the polyester polyols alcohol derivate of EB80, glyceryl propoxy-triacrylate and the 250 gram tripropylene glycol diacrylates that 120 gram merchants are called OTA-480 prepare resin compound.This mixture is used to all photopolymerization reactions.Methyldiethanolamine, MDEA are added in the partial confounding compound so that the MEDA of 1.5% weight to be provided.With the amount in table 1 and the table 2 light trigger is added, and mixture is applied to the film that obtains 2 mils on the cardboard.With cardboard by exciter lamp, the high emission wavelength of this lamp or near 308 millimicrons.For comparing, cardboard also passes through medium pressure mercury lamp.Two lamps are set to 400 watts of per inchs.Curing speed is with the decision of the belt speed of maximum, under this speed with film by reversing hand test (thumb twist test), the results are shown in following table.
Table 1
| Initiator | Curing speed (feet per minute clock) | The photoinitiator concentration (weight %) that is used for medium pressure mercury lamp | The photoinitiator concentration (weight %) that is used for the light trigger of exciter lamp |
| Benzophenone | ????150 | ????1.5 | ????- |
| 4,4 ＇-two (4-sec.-propyl phenoxy group) benzophenone | ????270 | ????0.04 | ????0.01 |
| 4,4 ＇-two (phenoxy group) benzophenone | ????425 | ????0.053 | ????0.013 |
| 4-(N-morpholino) benzophenone | ????325 | ????0.02 | ????0.007 |
| 4,4 ＇-two (2,4-two tert-pentyl phenoxy groups) benzophenone | ????325 | ????0.056 | ????0.011 |
Table 2
| Initiator | Photoinitiator concentration (weight %) | The curing speed (feet per minute clock) that is used for medium pressure mercury lamp | The curing speed (feet per minute clock) that is used for exciter lamp |
| Benzophenone | ????1.5 | ????150 | ????290 |
| 4,4 ＇-two (4-sec.-propyl phenoxy group) benzophenone | ????0.04 | ????270 | ????＞590 |
| 4,4 ＇-two (phenoxy group) benzophenone | ????0.053 | ????425 | ????＞590 |
| 4-(N-morpholino) benzophenone | ????0.02 | ????325 | ????＞590 |
| 4,4 ＇-two (2,4-two tert-pentyl phenoxy groups) benzophenone | ????0.055 | ????325 | ????＞590 |
The presentation of results of table 1 will obtain same curing speed, and compound of the present invention uses exciter lamp, and consumption is only for being used for about 1/4 of medium pressure mercury lamp.
The presentation of results of table 2, when exciter lamp and medium pressure mercury lamp during with the light trigger of same concentrations, then the curing speed of exciter lamp is much bigger.
Two table explanations, the curing speed of compound of the present invention is than big many of benzophenone.
Use exciter lamp and four compounds 4 in an embodiment, 4 ＇-two (4-sec.-propyl phenoxy group) benzophenone, 4,4 ＇-two (phenoxy group) benzophenone, 4-(N-morpholino) benzophenone and 4, the UV spectrum of 4 ＇-two (2,4-two tert-pentyl phenoxy groups) benzophenone quite is Fig. 1,2,3,4 and 5 respectively.
Top embodiment is explanation the present invention, is not to be used to limit the present invention.The present invention is by following claim and will comprise that claim equivalent is wherein determined.
Claims (20)
1. the compound that has logical formula I:
In the formula: A is-CO-or-CO-CO-;
Z be (H, H) ,-CH
2-,-S-,-O-,-CO-,-NR
9-or connect the key of two aromatic rings,
R
1And R
2Be selected from H with being independent of each other,
W=2-6 in the formula
X is 4-5 in the formula
With
X-R
7, condition is R
1And R
2Not all be H;
X is O or S;
R
3, R
4, R
5And R
6Be independent of each other, all be selected from-H ,-Cl ,-Br ,-NO
2,-CN ,-OH, C
1-C
8Alkyl, C
6-C
8Aryl, C
7-C
24Alkaryl or aralkyl, C
1-C
8Alkoxyl group, C
6-C
18Aryloxy, C
7-C
24Alkyl-aryloxy or alkoxy aryl, C
1-C
8Alkyl thioether ,-COOH and-COOR
7And
R
7, R
8And R
9Be selected from C with being independent of each other
1-C
8Alkyl and C
7-C
24Alkylaryl or arylalkyl.
2. the compound of claim 1, wherein R
1And R
2In at least one is
3. the compound of claim 1, wherein R
1And R
2In at least one is
4. the compound of claim 1, wherein R
1And R
2In at least one is
5. the compound of claim 1, wherein R
1And R
2In at least one is
W=2-6 in the formula
6. the compound of claim 1, wherein R
1And R
2In at least one is
X is 4-5 in the formula
7. the compound of claim 1, wherein R
1And R
2In at least one is
8. the compound of claim 1, wherein R
1And R
2In at least one is
9. the compound of claim 1, wherein R
1And R
2In at least one is
10. the compound of claim 1, wherein R
1And R
2In at least one is X-R
7
11. the compound of claim 1, wherein A is-CO-.
12. the compound of claim 1, wherein Z be (H, H).
13. the compound of claim 1, wherein said compound are 4,4 ＇-two (4-sec.-propyl phenoxy group) benzophenone.
14. the compound of claim 1, wherein said compound are 4,4 ＇ pairs of (phenoxy group) benzophenone.
15. the compound of claim 1, wherein said compound are 4,4 ＇ pairs of (2,4-two tert-pentyl phenoxy groups) benzophenone.
16. contain the photopolymerizable composition of photopolymerization compounds, contain at least one ethylenical unsaturated double bonds and light trigger in the photopolymerizable composition with logical formula I,
In the formula:: A is-CO-or-CO-CO-;
Z be (H, H) ,-CH
2-,-S-,-O-,-CO-,-NR
9-or connect the key of two aromatic rings,
R
1And R
2Be selected from H with being independent of each other,
W=2-6 in the formula
X is 4-5 in the formula
With
X-R
7, condition is R
1And R
2Not all be H;
X is O or S;
R
3, R
4, R
5And R
6Be independent of each other, all be selected from-H ,-Cl ,-Br ,-NO
2,-CN ,-OH, C
1-C
8Alkyl, C
6-C
8Aryl, C
7-C
24Alkaryl or aralkyl, C
1-C
8Alkoxyl group, C
6-C
18Aryloxy, C
7-C
24Alkyl-aryloxy or alkoxy aryl, C
1-C
8Alkyl thioether ,-COOH and-COOR
7And
R
7, R
8And R
9Be selected from C with being independent of each other
1-C
8Alkyl and C
7-C
24Alkaryl or aralkyl.
17. make the polymerization process of the photopolymerization compounds that contains at least one ethylenical unsaturated double bonds, this method is included under the existence with logical formula I compound said compound is exposed under the uv-radiation
In the formula: A is-CO-or-CO-CO-; (I)
Z be (H, H) ,-CH
2-,-S-,-O-,-CO-,-NR
9-or connect the key of two aromatic rings,
R
1And R
2All be selected from with being independent of each other H,
W=2-6 in the formula
X is 4-5 in the formula
With
X-R
7, condition is R
1And R
2Not all be H;
X is O or S;
R
3, R
4, R
5And R
6Be independent of each other, all be selected from-H ,-Cl ,-Br ,-NO
2,-CN ,-OH, C
1-C
8Alkyl, C
6-C
8Aryl, C
7-C
24Alkaryl or aralkyl, C
1-C
8Alkoxyl group, C
6-C
18Aryloxy, C
7-C
24Alkyl-aryloxy or alkoxy aryl, C
1-C
8Alkyl thioether ,-COOH and-COOR
7And
R
7, R
8And R
9Be selected from C with being independent of each other
1-C
8Alkyl and C
7-C
24Alkylaryl or arylalkyl.
18. the method for claim 17, wherein said step of exposure comprises exposes said composition under the spectral radiance of the about 250-350 millimicron of wavelength band.
19. the method for claim 17, wherein said step of exposure comprises exposes said composition under the spectral radiance of the about 290-325 millimicron of wavelength band.
20. the method for claim 17, wherein said step of exposure comprise said composition is exposed under the about 308 millimicrons spectral radiance of wavelength band.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 97195665 CN1222163A (en) | 1996-05-20 | 1997-05-19 | Photoactive compounds for use with narrow wavelength band ultraviolet (UV) curing systems |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60/017,127 | 1996-05-20 | ||
| CN 97195665 CN1222163A (en) | 1996-05-20 | 1997-05-19 | Photoactive compounds for use with narrow wavelength band ultraviolet (UV) curing systems |
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| Publication Number | Publication Date |
|---|---|
| CN1222163A true CN1222163A (en) | 1999-07-07 |
Family
ID=5179302
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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| Country | Link |
|---|---|
| CN (1) | CN1222163A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101891844B (en) * | 2010-02-05 | 2012-05-23 | 北京化工大学 | Iridoid compounds used as ultraviolet-aided initiating agents |
-
1997
- 1997-05-19 CN CN 97195665 patent/CN1222163A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101891844B (en) * | 2010-02-05 | 2012-05-23 | 北京化工大学 | Iridoid compounds used as ultraviolet-aided initiating agents |
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