CN1504448A - Ketone photo initiator compound having active side chain, preparing process and application thereof - Google Patents

Ketone photo initiator compound having active side chain, preparing process and application thereof Download PDF

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Publication number
CN1504448A
CN1504448A CNA02149181XA CN02149181A CN1504448A CN 1504448 A CN1504448 A CN 1504448A CN A02149181X A CNA02149181X A CN A02149181XA CN 02149181 A CN02149181 A CN 02149181A CN 1504448 A CN1504448 A CN 1504448A
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Prior art keywords
hydroxyl
phenyl
methyl
compound
hydroxy
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Inventor
赵文超
阎庆金
王永林
钟振楼
尹应武
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Yingli Science And Technology Development Co Ltd Beijing
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Yingli Science And Technology Development Co Ltd Beijing
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Priority to CNA02149181XA priority Critical patent/CN1504448A/en
Priority to AU2003221292A priority patent/AU2003221292A1/en
Priority to PCT/CN2003/000181 priority patent/WO2004048307A1/en
Publication of CN1504448A publication Critical patent/CN1504448A/en
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    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • 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
    • G03F7/031—Organic compounds not covered by group G03F7/029

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a ketone photo-initiation agent compound with active lateral chains, the process for preparing it and use thereof, wherein the compound is odor free and can formed into macromolecule, it possesses water-solubility, thus is suitable to act as photo-initiation agent for the free radical aggregation of carbon-carbon double bond compounds such as acrylic acid ester compounds.

Description

With ketone photoinitiator compound of active side chain and its production and application
Invention field
The present invention relates to a kind of ketone photoinitiator compound with active side chain and its production and application.This compound odorlessness, but high molecular have water-solublely, are suitable as light trigger and are used for for example radical polymerization of acrylic ester compound of carbon-carbon double bond compound.
Background of invention
The present invention relates to ketone new compound and their manufacture method and the photocurable systems that contains them of the active side chain of a series of bands.
Photocuring technology is a kind of green technology in the fields such as coating, printing ink, tamanori; body of material generally is made up of the resin that contains acryl and polyalcohol acrylate and light trigger; under enough luminous energy (for example ultraviolet ray) effect; all solidify; with traditional solvent system ratio that contains; solvent-free discharging, efficient height, energy-conservation etc. with conspicuous characteristics have been applied in various fields.But still have a lot of shortcomings, and big as: the smell of acrylate and residual initiator, certain pungency is arranged, be difficult to realize spraying that the film shrinking percentage is big.Therefore people constantly study, and existing so far many progress just combine water-borne coatings as the photocuring system of water-based and easily transfer, are convenient to construct and photocuring dual characteristics rapidly and efficiently without organic solvent, performance.But the commercial light trigger that is fit to the water-based system use is fewer, and existing light trigger is not that solvability is bad, be exactly lose with moisture evaporation easily.2-hydroxy-2-methyl-4 '-(2-hydroxyl-oxethyl) phenyl-1-acetone that U.S. Pat 4861916 inventors propose is fit to water-based system to be used, and commercialization is sold.But its price is expensive, causes user's production cost height.
At the deficiencies in the prior art, the present inventor has carried out intensive research.Found that this patent describes a new compounds and have good performance, the special side chain that this compounds had, but make it to have water-soluble high molecular and extremely low smell, can be used for for example light-initiated radical polymerization of acrylic ester compound of carbon-carbon double bond compound.Provide their manufacture method and methods for using them simultaneously, so finished the present invention.
Summary of the invention
The invention provides a kind of ketone photoinitiator compound with active side chain and its production and application.Hydroxypropyl is introduced in phenyl ring contraposition in alpha-hydroxy ketones or benzophenone, but makes this compounds have water-soluble high molecular and extremely low smell; With propylene glycol phenyl ether is that raw material has prepared target compound through steps such as acylation reaction, bromo-reaction, alkaline hydrolysis reactions; This compounds is suitable as light trigger and is used for for example light-initiated radical polymerization of acrylic ester compound of carbon-carbon double bond compound.
Detailed Description Of The Invention
One of purpose of the present invention is that design one class has the light trigger of special side chain, but makes it to have the character of water-soluble high molecular and extremely low smell.
Another object of the present invention provides the preparation method of described compound, and Using such method can be synthesized them easily.
A further object of the present invention is the described application of compound method of research, and described application of compound example is provided.
The series compound of the present invention by following structural formula I is provided be as light trigger, and the preparation method of this compound and use brief overview.
Adopt photoinitiator compound of the present invention, not only can be used in the water-based UV system formulation and use, and be suitable for the use of 100%UV system, simultaneously, it has also satisfied the requirement of user to the low smell of light trigger.Moreover, it can also be used for the preparation of high molecular light trigger as the light trigger unit, and the distribution of light trigger in system of process high molecular more is tending towards evenly, do not have smell, do not have surface transport.
Figure A0214918100051
R wherein 1Be H,, R 2Be CH 3Or
R 1Be CH 3,, R 2Be H
Z is CR 3R 4(OR 5) or phenyl;
R 3Be H, C 1-3Alkyl or phenyl,
R 4Be H, C 1-3Alkyl, C 1-3Alkoxyl group
Or R 3R 4Be-(CH 2) 5-
R 5Be C 1-3Alkyl;
X is O, S;
N=1,2 integer
When Z is phenyl, then is the equal of the benzophenone that has active side chain, thereby makes the benzophenone photoinitiator can be used for water-based system and carry out high molecular.
When Z is CR 3R 4(OR 5), R wherein 3=R 4=CH 3, R 5During=H, be equivalent to the alpha-alcohol ketone photoinitiator and have active side chain, can be used for water-based UV system and 100%UV system and carry out high molecular.Or R 3Be phenyl, R 4Be alkoxyl group, R 5When being alkyl, being equivalent to benzil dme photoinitiator and having active side chain.
In the prior art, do not find this compound and its production and application example.
Below be some examples of compounds:
(1) 2-hydroxy-2-methyl-4 '-(2-hydroxyl propoxy-) phenyl-1-acetone
(2) 1-hydroxyl-1-cyclohexyl-4 '-(2-hydroxyl propoxy-) benzophenone
(3) 2-hydroxy-2-methyl-4 '-[2-(2-hydroxyl propoxy-) propoxy-] phenyl-1-acetone
(4) 2-hydroxy-2-methyl-4 '-(2-hydroxyl-1-methyl ethoxy) phenyl-1-acetone
(5) 1-hydroxyl-1-cyclohexyl-4 '-(2-hydroxyl-1-methyl ethoxy) benzophenone
(6) 2-hydroxy-2-methyl-4 '-[2-(2-hydroxyl-1-methyl ethoxy)-1-methyl ethoxy] phenyl-1-acetone
(7) methodology of organic synthesis has been adopted in 4-(2-hydroxyl propoxy-) their preparation of benzophenone, with propylene glycol phenyl ether is raw material, in reflux temperature acetic anhydride esterification, again with a kind of acyl chlorides such as isobutyryl chloride, cyclohexanecarbonyl chloride, carry out acylation reaction at 0-10 ℃, steps such as bromo-reaction, alkaline hydrolysis reaction, purifying have prepared the alpha-alcohol ketone class target compound that has side chain; Carboxylate obtains 4-(2-hydroxyl propoxy-) benzophenone through alkaline hydrolysis, purifying after using the Benzoyl chloride acylations.
About they application in photocuring system, usually addition is 0.01%～10% with respect to resin, and is preferred 0.5%～5%, and they can be dissolved in prepolymer or the reactive thinner easily.In prescription, can use other known light triggers as coinitiator; Can use necessary auxiliary agent such as tertiary amine, pigment etc.
As prepolymer or reactive thinner the C=C group must be arranged, especially acryl compound is more commonly used.In water-based system, resin is water miscible or emulsifying water, solids content 10～85%.
Photocuring system is usually used in paper, timber, plastics, metallic surface coating and printing with the product form of coating, printing ink or tackiness agent.Adopt UV radiation, the high voltage mercury lamp of preferred wavelength range 250～500nm during curing.
Photoinitiator compound of the present invention is compared its superiority and is that but it has water-soluble high molecular and extremely low smell with existing photoinitiator compound.
Embodiment
The present invention can be further described with indefiniteness embodiment hereinafter.
Preparation (a) 305g (2.0mol) the 1-phenoxy group of embodiment 1:2-hydroxy-2-methyl-4 '-(2-hydroxyl propoxy-) phenyl-1-acetone-2-propyl alcohol (2-hydroxypropyl phenylate) and 245g (2.4mol) acetic anhydride, being heated to reflux temperature kept 2 hours for 143 ℃, acetic acid and excessive acetic anhydride are removed in underpressure distillation, get light yellow liquid 380g (yield 98%)
(b) 440g (3.3mol) aluminum trichloride (anhydrous) stirs in the 800ml ethylene dichloride and cools to-5 ℃, keep below 0 ℃, drip 291.5g (1.5mol) acetate 2-(1-phenoxy group) propyl ester in 1 hour, drip 168g (1.6mol) isobutyryl chloride then in 2 hours, same temperature continues to stir 2 hours.The careful in batches impouring of reaction solution contains in the 2.5Kg trash ice of 900ml hydrochloric acid.Tell organic phase, washing once concentrates and underpressure distillation after the siccative dried overnight.Obtain 396g (yield 95%) 4-(2-acetoxyl group propoxy-) phenyl isobutyl ketone.150～155 ℃/0.5mmHg. of boiling point
(c) 264g (1.0mol) 4-(2-acetoxyl group propoxy-) phenyl isobutyl ketone is dissolved in the 500ml ethylene dichloride, adds the 100ml Glacial acetic acid, stirs, and drips 176g (1.1mol) liquid bromine, stirs 5 hours after washing reaction solutions, concentrated 332g yellow oil.In above-mentioned oily matter with phase-transfer catalyst 6g, dripped 45 ℃ of following high degree of agitation of 400g 30% sodium hydroxide solution 2 hours, add water stratification, oil reservoir is dissolved in the 250ml ethyl acetate, be washed to neutrality, the dry recovery ethyl acetate that concentrates gets yellow oil crude product 202.3g, obtains white powdered 2-hydroxy-2-methyl-4 '-(2-hydroxyl propoxy-) phenyl-1-acetone 143g (yield 60%) with the ethanol decolorization recrystallization.76～79 ℃ of fusing points; Results of elemental analyses: C65.25% (theoretical value 65.52%), H7.70 (theoretical value 7.61%); Ultra-violet absorption spectrum is gone into max275.5nm.
NMR hydrogen spectrum data: two groups of δ 8.07-6.94ppm (phenyl ring 4H); δ 4.26-4.19ppm multiplet (CH); Two groups of δ 4.03-3.86 (CH2); δ 1.63 unimodal (2CH3); δ 1.30,1.28 bimodal (CH3)
(d) crude product is collected 180-185 ℃/60Pa cut with the method for underpressure distillation, obtains near colourless liquid, becomes white solid after the condensation.Analytical results is with (c).
The preparation of embodiment 2:2-hydroxy-2-methyl-4 '-(2-hydroxyl-1-methyl ethoxy) phenyl-1-acetone
Use 2-phenoxy group-1-propyl alcohol to be raw material, synthetic method obtains the crude product underpressure distillation with embodiment 1, collects 180-185 ℃/60Pa cut, is thick liquid after the condensation.NMR hydrogen spectrum data: two groups of δ 8.07-6.95ppm (phenyl ring 4H); δ 4.68-4.58ppm sextet (CH) δ 3.79,3.77 bimodal (CH2); δ 1.63 unimodal (2CH3); δ 1.38,1.36 bimodal (CH3)
The preparation of embodiment 3:4-(2-hydroxyl propoxy-) benzophenone
(a) 440g (3.3mol) aluminum trichloride (anhydrous) stirs in the 800ml ethylene dichloride and cools to-5 ℃, keep below 0 ℃, drip 291.5g (1.5mol) acetate 2-(1-phenoxy group) propyl ester in 1 hour, drip 225g (1.6mol) Benzoyl chloride then in 2 hours, same temperature continues to stir 2 hours.The careful in batches impouring of reaction solution contains in the 2.0Kg trash ice of 900ml hydrochloric acid.Tell organic phase, washing once concentrates after the siccative dried overnight, obtains 425g (yield 95%) 4-(2-acetoxyl group propoxy-) benzophenone.
(b) in 150g (0.5mol) oily matter with phase-transfer catalyst 3g, dripped 45 ℃ of following high degree of agitation of 100g 30% sodium hydroxide solution 2 hours, add water stratification, oil reservoir is dissolved in the 250ml ethyl acetate, be washed to neutrality, the dry recovery ethyl acetate that concentrates gets light yellow oil crude product 115.3g, obtains 4-(2-hydroxyl propoxy-) the benzophenone 102g (yield 80%) of white solid with the ethanol decolorization recrystallization.66.5～68.3 ℃ of fusing points.Results of elemental analyses: C74.17% (theoretical value 74.98%), H6.34 (theoretical value 6.29%); Ultra-violet absorption spectrum is gone into max288.5nm.NMR hydrogen spectrum data: five groups of δ 7.85-6.96ppm (two phenyl ring 9H); δ 4.28-4.21ppm multiplet (CH); Two groups of δ 4.04-3.86ppm (CH2); δ 2.308,2.296ppm bimodal (OH); δ 1.33,1.31ppm bimodal (CH3)
Embodiment 4: the UV of varnish solidifies
46 parts of urethane acrylates (EB264, UCB. S.A. (BE) Bruxelles Belgium) add 5 parts of 2-hydroxy-2-methyls-4 '-(2-hydroxyl propoxy-) phenyl-1-acetone, 3 parts of trolamines in the system of 16 parts of Resins, epoxy acrylate and 30 parts of HDDA.
The 40um that films on sheet glass uses high voltage mercury lamp (80w/cm, test plate (panel) and lamp are apart from 20cm), and the 45s surface is little glues the 60s completely solidified.The transparent not xanthochromia of cured film does not have residual smell.
Use embodiment 2 and 3 prepared compounds also to obtain analog result
Embodiment 5: the UV of printing-ink solidifies
16 parts of urethane acrylate (EB264, UCB. S.A. (BE) Bruxelles Belgium), add 5 parts of 2-hydroxy-2-methyls-4 '-(2-hydroxyl propoxy-) phenyl-1-acetone in the system of 46 parts of Resins, epoxy acrylate and 30 parts of HDDA, 3 parts of trolamines and 8 parts of phthalocyanine blues (7072FR, BASF AG).
The 2um that films on sheet glass uses high voltage mercury lamp (80w/cm, test plate (panel) and lamp are apart from 20cm), and the 60s surface is little glues the 90s completely solidified.
Embodiment 6: the UV of water-based system solidifies
100 parts of solid content 30% aqueous polyurethane acrylates, 0.3 part of 2-hydroxy-2-methyl-4 '-(2-hydroxyl propoxy-) phenyl-1-acetone can dissolve rapidly, adds 0.2 part of trolamine again,
The 45um that films on sheet glass dries back 16um, uses high voltage mercury lamp (80w/cm, test plate (panel) and lamp are apart from 20cm), and the 25s surface is little glues the 48s completely solidified.The transparent not xanthochromia of cured film does not have residual smell.
Use embodiment 2 and 3 prepared compounds also to obtain analog result.
Comparative examples 1: the UV of varnish solidifies
2-hydroxy-2-methyl-4 ' among the embodiment 4-(2-hydroxyl propoxy-) phenyl-1-acetone changes Darocur2959 into, carries out identical curing operation, and the 45s surface is little sticking, the 60s completely solidified.
Comparative examples 2: the UV of water-based system solidifies
2-hydroxy-2-methyl-4 ' among the embodiment 7-(2-hydroxyl propoxy-) phenyl-1-acetone changes Darocur2959 into, carries out identical curing operation, and the 25s surface is little sticking, the 48s completely solidified.

Claims (7)

1, a kind of compound, its general structure:
Figure A0214918100021
R wherein 1Be H,, R 2Be CH 3Or
R 1Be CH 3,, R 2Be H
Z is CR 3R 4(OR 5) or phenyl;
R 3Be H, C 1-3Alkyl or phenyl,
R 4Be H, C 1-3Alkyl, C 1-3Alkoxyl group
Or R 3R 4Be-(CH 2) 5-
R 5Be C 1-3Alkyl;
X is O, S;
N=1,2 integer
2, compound according to claim 1, it comprises:
(1) 2-hydroxy-2-methyl-4 '-(2-hydroxyl propoxy-) phenyl-1-acetone
(2) 1-hydroxyl-1-cyclohexyl-4 '-(2-hydroxyl propoxy-) benzophenone
(3) 2-hydroxy-2-methyl-4 '-[2-(2-hydroxyl propoxy-) propoxy-] phenyl-1-acetone
(4) 2-hydroxy-2-methyl-4 '-(2-hydroxyl-1-methyl ethoxy) phenyl-1-acetone
(5) 1-hydroxyl-1-cyclohexyl-4 '-(2-hydroxyl-1-methyl ethoxy) benzophenone
(6) 2-hydroxy-2-methyl-4 '-[2-(2-hydroxyl-1-methyl ethoxy)-1-methyl ethoxy] phenyl-1-acetone
(7) 4 '-(2-hydroxyl propoxy-) benzophenone
3, the preparation method of compound according to claim 2 is that raw material has prepared target compound through steps such as acylation reaction, bromo-reaction, alkaline hydrolysis reactions with propylene glycol phenyl ether, is able to purifying through underpressure distillation and/or crystallization again.
4, a kind of photocurable systems comprises at least a methyl and/or acrylic ester compound, light trigger described in prepolymer and/or reactive thinner and at least a claim 1;
5, light trigger according to claim 4, its addition are 0.01～10%;
6, a kind of photocurable water-based system comprises polymkeric substance and the described light trigger of at least a claim 1 and the necessary assistant of at least a aqueous dimethylformamide and/or acroleic acid esterification.
7, light trigger according to claim 6, its addition are 0.01～10%;
CNA02149181XA 2002-11-28 2002-11-28 Ketone photo initiator compound having active side chain, preparing process and application thereof Pending CN1504448A (en)

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CNA02149181XA CN1504448A (en) 2002-11-28 2002-11-28 Ketone photo initiator compound having active side chain, preparing process and application thereof
AU2003221292A AU2003221292A1 (en) 2002-11-28 2003-03-13 Ketones photoinitiators with reactive side chains and the photocuring system thereof
PCT/CN2003/000181 WO2004048307A1 (en) 2002-11-28 2003-03-13 Ketones photoinitiators with reactive side chains and the photocuring system thereof

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2018090354A1 (en) * 2016-11-21 2018-05-24 北京英力科技发展有限公司 Photocurable composition without benzene release

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JP6318111B2 (en) * 2015-03-27 2018-04-25 富士フイルム株式会社 Photopolymerization initiator and ink composition, ink set and image forming method using the same
CN110467692A (en) 2018-05-11 2019-11-19 北京英力科技发展有限公司 A kind of polyacrylate macromolecular photoinitiator and its synthetic method and application

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DE3512179A1 (en) * 1985-04-03 1986-12-04 Merck Patent Gmbh, 6100 Darmstadt PHOTO INITIATORS FOR PHOTOPOLYMERIZATION IN AQUEOUS SYSTEMS

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018090354A1 (en) * 2016-11-21 2018-05-24 北京英力科技发展有限公司 Photocurable composition without benzene release

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