CN102924509A - Bisphosphono phosphonate compound - Google Patents

Bisphosphono phosphonate compound Download PDF

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Publication number
CN102924509A
CN102924509A CN 201110227608 CN201110227608A CN102924509A CN 102924509 A CN102924509 A CN 102924509A CN 201110227608 CN201110227608 CN 201110227608 CN 201110227608 A CN201110227608 A CN 201110227608A CN 102924509 A CN102924509 A CN 102924509A
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compound
methyl
phosphorous acid
acrylate
reaction
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陈婷
王瑜
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Shenzhen Youwei Chemical Technology Co., Ltd.
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陈婷
王瑜
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Priority to CN 201110227608 priority Critical patent/CN102924509A/en
Priority to PCT/CN2012/079445 priority patent/WO2013020469A1/en
Publication of CN102924509A publication Critical patent/CN102924509A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3247—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se)
    • C07F9/3252—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se) containing the structure -C(=X)-P(=X)(R)(XR), (X = O, S, Se)
    • 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

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

The present invention relates to the technical field of new UV light radiation free radical polymerization materials, particularly to a bisphosphono phosphonate compound having the following structural general formula, a preparation method of the bisphosphono phosphonate compound, uses of the bisphosphono phosphonate compound as a photoinitiator for carrying out UV free radical photo polymerization curing on an alkene-containing unsaturated compound system, and a UV free radical photo polymerization curing material system containing the compound.

Description

Two phosphono phosphonate compounds
[technical field]
The present invention relates to UV optical radiation radical polymerization new material technology field, be particularly related to structural formula two phosphono phosphonate compounds as follows, its preparation method, its conduct contains the purposes that the unsaturated allyl compound system is carried out the light trigger of UV radical photopolymerization curing, and the UV radical photopolymerization solidify material system that contains this compounds.
[background technology]
Some phosphono type structural compounds are because its longwave optical absorbs and photobleaching Properties is important light trigger in UV uv radiation curing field, quite abundant disclosure has been arranged in patent documentation, US5218009 for example, EP0615980A2, and CN1659175A etc.Also be in recent years research emphasis about the new preparation technology of some phosphono type structural compounds, the representative patents document is WO2006/056541A1 for example.Yet, phosphono type photoinitiator compound cost and price usually is significantly higher than other kind photoinitiator compound (for example amido ketone or hydroxyketone type light trigger), the preparation technology who has disclosed uses the basic metal (sodium of height air-sensitive unavoidablely, potassium, or lithium metal) tediously long reaction times and the operation steps of experience prepares corresponding metal phosphinate compound, productive rate low (for example the end product yield that obtains of above-mentioned up-to-date technique WO2006/056541A1 is usually less than 30%), production safety hidden danger is very large, and this economy type friendly to environmental protection that has seriously limited this compounds is applied.Therefore, identifying the phosphono type structural compounds of finding new more economical close friend, open up simultaneously its brand-new preparation technology and application purpose, is the challenge that has using value that current UV radiation curing field of new faces.
[summary of the invention]
This application has now unexpectedly been found that the two phosphono phosphonate compounds of structure shown in general formula I are effectively to contain unsaturated allyl compound system UV radical photopolymerization to solidify light trigger.Compound I (following claim defines) is not only the new texture that has no report, and of equal importance is that they must realize preparation with the economy novel process that is different from document disclosure method fully.
In general formula I, R is the alkyl that contains the straight or branched of 1-24 carbon atom, and this alkyl can be for being no more than 4 discontinuity Sauerstoffatom, nitrogen-atoms, and Siliciumatom, sulphur atom is interrupted, or this alkyl can contain 1-40 fluorine atom; Or R contains the phenyl of 6-24 carbon atom or contains 1-4 substituent substituted-phenyl, and these substituting groups also can be for being no more than 4 discontinuity Sauerstoffatom, nitrogen-atoms, and Siliciumatom, or sulphur atom is interrupted.Preferably, R=methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, phenyl, tolyl.
Being worth ben is, although the two phosphono type compound manufacture method that disclose via document can prepare the structure that contains alkyl (side chain or straight chain) or aryl (multiple substituting group) on a series of phosphorus atom, for example patented technology WO2006/056541A1 and CN1659175A, but its phosphorus-to-carbon bonds generate chemical reaction characteristic determined its can not for the preparation of the general formula I structrual description that contains OR group (alkoxyl group or aryloxy) on the phosphorus atom phosphorous-the oxygen key compound.
The application has now found that compound of Formula I can the easily manufacturing via following reaction expression economy.With industrial cheap and easy to get and safe ortho phosphorous acid H 3PO 2(hypophosphorous acid) is crucial starting raw material, obtains intermediate time industry phosphoric acid ester A via R base esterification, A then and sym-trimethylbenzene formaldehyde carry out pair contracting carbonyl nucleophilic additions and obtain senior intermediate B.B can obtain target compound I through the hydroxyl catalyzed oxidation.The core feature of this technological process is to have used general formula to carry out two contracting carbonyl nucleophilic additions as the ortho phosphorous acid ester of A and sym-trimethylbenzene formaldehyde to prepare general formula and be the senior intermediate of the hydroxy phosphonate of B.A can participate in reaction with the pure compound form, and the original position form of mixtures after also can the following phosphitylated reaction is finished under conditions suitable participates in reaction.
Figure BSA00000554026100022
Suitable enzymatic synthesis condition can be that [or its corresponding form is as MOP (O) H take ortho phosphorous acid 2Amine salt, the preferred NH of M 4, PhNH 3, HNEt 3, lower with] and alkyl orthoformate reaction, or promote lower and alcohol roh reacts with ortho phosphorous acid (or its corresponding amine salt) and acyl chlorides, or take ortho phosphorous acid (or its corresponding amine salt) and form as Si (OR) 4Siloxane reactions.Have been reported about these reactions and some ortho phosphorous acid ester synthesis documents, for example: R is methyl, Phosphorus, Sulfur and Silicon and the Related Elements, 177 (6-7), 1793-1796; 2002; R is ethyl, Tetrahedron Letters, 42 (30), 5033-5036; 2001; R is sec.-propyl, Chemistry Letters, 33 (2), 116-117; 2004 and ACS Medicinal Chemistry Letters, 2 (1), 11-16; 2011; R is the tertiary butyl, Tetrahedron Letters, 37 (4), 425-8; 1996; R is normal-butyl, Journal of Organic Chemistry, 70 (10), 4064-4072; 2005 and Journal of Organometallic Chemistry, 643-644,154-163; 2002; R is phenyl, Journal of Organometallic Chemistry, 643-644,154-163; 2002.
The condensation of ortho phosphorous acid ester A and aldehyde can be used suitable alkali promotor, and preferred alkali is for example Et of trimethylamine compound 3N, Bu 3N, or iPr 2NEt.
Suitable oxide catalyst is to be selected to contain Mo, the metal-salt of W or V, and bis-acetylacetonate vanadium oxide ， Molybdenum acid anhydrides ， Molybdenum hydrochlorate ， Lin Molybdenum hydrochlorate for example, tungstic anhydride, tungstate, or contain one or more of the heteropolyacid of these metals or heteropolyacid salt.Suitable terminal oxygenant can be organo-peroxide such as tertbutanol peroxide etc.
This application discloses the suitable UV photocuring system of a class simultaneously.Such system comprises and at least aly polymerisablely contains the unsaturated component of ethylene linkage, and to comprise at least a compound of Formula I be one of light trigger or light trigger component.Calculate to contain the per 100 parts of weight of the unsaturated component total amount of ethylene linkage in the system, the appropriate vol of the compound of Formula I that contains is the 0.05-15 weight part, preferred 0.5-8 weight part.The polymerisable unsaturated component of ethylene linkage that contains that the suitable UV photocuring system of this application disclosure comprises is compound or the mixture that can be crosslinked by the Raolical polymerizable of this pair key, this unsaturated component of ethylene linkage that contains can be monomer, oligopolymer or prepolymer, or their mixture or multipolymer.The monomer of suitable radical polymerization is for example to contain the ethylene linkage polymerisable monomer, includes but not limited to (methyl) acrylate, propenal, alkene, conjugated diolefin, vinylbenzene, maleic anhydride, fumaric acid anhydride, vinyl-acetic ester, vinyl pyrrolidone, vinyl imidazole, (methyl) vinylformic acid, (methyl) acrylic acid derivative is (methyl) acrylamide for example, vinyl halide, vinylidene halide etc.Suitable prepolymer and oligopolymer includes but not limited to (methyl) acrylic copolymer of (methyl) acryloyl functional group, urethane manthanoate (methyl) acrylate, polyester (methyl) acrylate, unsaturated polyester, polyethers (methyl) acrylate, siloxanes (methyl) acrylate, Resins, epoxy (methyl) acrylate etc.Its suitable number-average molecular weight can be in for example 500 to 10000 changes, preferred 500-5000 span.
[embodiment]
Embodiment one:
Figure BSA00000554026100041
Under nitrogen protection, the anhydrous ortho phosphorous acid of 6.6 grams is placed 50 milliliters fresh distilled tetrahydrofuran and toluene Mixed Solvent (volume ratio 1/1); keep temperature of reaction about 5 degrees centigrade, under agitation slowly add 44 milliliters trimethyl orthoformate to it.React that system naturally is warming up to room temperature and continued stirring reaction 3 hours after 2 hours.Reaction solution adds 34 gram 1，3，5-trimethyl-benzene formaldehyde with backward its of 200 ml methanol dilution, and the mixed system back flow reaction is until the disappearance of TLC detection display ortho phosphorous acid methyl esters raw material.Reaction solution decompression desolvation and volatile constituent.Resistates and 300 milliliters of chlorobenzenes mix, and add successively 45 milliliters of peroxidation and count butanols, 20 ml waters, and 3.6 gram Vanadium Pentoxide in FLAKES complex compounds, reaction solution stirs and spends the night.Reaction mixture is regulated as for alkalescence with 2N sodium hydroxide, organic phase saturated aqueous common salt and Na after the aqueous phase discarded 2SO 310% solution wash respectively once the reclaim under reduced pressure chlorobenzene solvent.Resistates obtains target compound sterling 22 grams by one 30 centimetres wide and 80 centimetres of high silicagel columns with the ethyl acetate/hexane wash-out, and total recovery is in initial ortho phosphorous acid approximately 60%.Ultimate analysis: C 21H 25O 4P, theoretical value: C%67.73%; H6.77%; Experimental value: C%67.87%; H6.81%.
Other embodiment two to five compounds are with as above similarly operation steps preparation, and institute does not exist together and only is corresponding ortho phosphorous acid ester H 2P (O) OR is with reference to reacting with addition and the subsequent oxidation of 1，3，5-trimethyl-benzene formaldehyde as carrying out behind the independent preparation of front literature cited step and the purifying again.Yield and C/H analytical results are as follows:
Figure BSA00000554026100051
UV photocuring Application Example:
Prepare the photocuring specimen according to following weight percent:
30 parts: epoxy acrylate;
35 parts: polyester acrylate;
5 parts: hexanediyl ester;
3 parts: pentaerythritol triacrylate;
23 parts: TiO 2 pigment;
4 parts: the embodiment photoinitiator compound.
Be sprayed on the white substrate after fully grinding said components evenly, form approximately 5 microns coating.Take the 200W high voltage mercury lamp as light source in distance sample 12 centimeters irradiation.Finger pressure is scraped embrocation judgement coating and is solidified situation fully.Above-described embodiment compound one to five all causes the rete completion of cure, has shown good photo sensitized initiation performance.

Claims (4)

1. one kind for general structure I describes compound, and wherein R is the alkyl that contains the straight or branched of 1-24 carbon atom, and this alkyl can be for being no more than 4 discontinuity Sauerstoffatom, nitrogen-atoms, Siliciumatom, or sulphur atom is interrupted, or this alkyl can contain 1-40 fluorine atom; Or R contains the phenyl of 6-24 carbon atom or contains 1-4 substituent substituted-phenyl, and these substituting groups also can be for being no more than 4 discontinuity Sauerstoffatom, nitrogen-atoms, and Siliciumatom, or sulphur atom is interrupted.Preferably, R=methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, phenyl, tolyl.
Figure FSA00000554026000011
2. the manufacture method of compound of Formula I.Shown in the following reaction expression, with industrial cheap and easy to get and safe ortho phosphorous acid H 3PO 2Be crucial starting raw material, obtain intermediate ortho phosphorous acid ester A via R base esterification, A then and sym-trimethylbenzene formaldehyde carry out pair contracting carbonyl nucleophilic additions and obtain senior intermediate B.B can obtain target compound I through the hydroxyl catalyzed oxidation.The core feature of this technological process is to have used general formula to carry out two contracting carbonyl nucleophilic additions as the ortho phosphorous acid ester of A and sym-trimethylbenzene formaldehyde to prepare general formula and be the senior intermediate of the hydroxy phosphonate of B.A can participate in reaction with the pure compound form, and the original position form of mixtures after also can the following phosphitylated reaction is finished under conditions suitable participates in reaction.
Figure FSA00000554026000012
Suitable enzymatic synthesis condition can be that [or its corresponding form is as MOP (O) H take ortho phosphorous acid 2Amine salt, the preferred NH of M 4, PhNH 3, HNEt 3, lower with] and alkyl orthoformate reaction, or with ortho phosphorous acid (or its corresponding amine salt) under acyl chlorides promotes and the alcohol roh reaction, or take ortho phosphorous acid (or its corresponding amine salt) and form as Si (OR) 4Siloxane reactions.
The condensation of ortho phosphorous acid ester A and aldehyde can be used suitable alkali promotor, and preferred alkali is for example Et of trimethylamine compound 3N, Bu 3N, or iPr 2NEt.
Suitable oxide catalyst is to be selected to contain Mo, the metal-salt of W or V, and bis-acetylacetonate vanadium oxide ， Molybdenum acid anhydrides ， Molybdenum hydrochlorate ， Lin Molybdenum hydrochlorate for example, tungstic anhydride, tungstate, or contain one or more of the heteropolyacid of these metals or heteropolyacid salt.Suitable terminal oxygenant can be organo-peroxide such as tertbutanol peroxide etc.
3. compound of Formula I is carried out the purposes of the radical-cured light trigger of UV photopolymerization as the mixture system that contains the ethylene linkage unsaturated compound or contain the ethylene linkage unsaturated compound.
4. the UV photocuring system that a class is suitable.Such system comprises and at least aly polymerisablely contains the unsaturated component of ethylene linkage, and to comprise at least a compound of Formula I be one of light trigger or light trigger component.Calculate to contain the per 100 parts of weight of the unsaturated component total amount of ethylene linkage in the system, the appropriate vol of the compound of Formula I that contains is the 0.05-15 weight part, preferred 0.5-8 weight part.The polymerisable unsaturated component of ethylene linkage that contains that the suitable UV photocuring system of this application disclosure comprises is compound or the mixture that can be crosslinked by the Raolical polymerizable of this pair key, this unsaturated component of ethylene linkage that contains can be monomer, oligopolymer or prepolymer, or their mixture or multipolymer.The monomer of suitable radical polymerization is for example to contain the ethylene linkage polymerisable monomer, includes but not limited to (methyl) acrylate, propenal, alkene, conjugated diolefin, vinylbenzene, maleic anhydride, fumaric acid anhydride, vinyl-acetic ester, vinyl pyrrolidone, vinyl imidazole, (methyl) vinylformic acid, (methyl) acrylic acid derivative is (methyl) acrylamide for example, vinyl halide, vinylidene halide etc.Suitable prepolymer and oligopolymer includes but not limited to (methyl) acrylic copolymer of (methyl) acryloyl functional group, urethane manthanoate (methyl) acrylate, polyester (methyl) acrylate, unsaturated polyester, polyethers (methyl) acrylate, siloxanes (methyl) acrylate, Resins, epoxy (methyl) acrylate etc.Its suitable number-average molecular weight can be in for example 500 to 10000 changes, preferred 500-5000 span.
CN 201110227608 2011-08-09 2011-08-09 Bisphosphono phosphonate compound Pending CN102924509A (en)

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CN103333202A (en) * 2013-06-08 2013-10-02 广州市博兴化工科技有限公司 Epoxy compound-based phosphate ester-containing long wave light-absorbing initiator and preparation method thereof
CN104870456A (en) * 2012-12-19 2015-08-26 巴斯夫欧洲公司 Derivatives of bisacylphosphinic acid, their preparation and use as photoinitiators
WO2017120743A1 (en) * 2016-01-11 2017-07-20 Henkel IP & Holding GmbH Silicone-compatible compounds
CN109867693A (en) * 2019-01-08 2019-06-11 广东博兴新材料科技有限公司 Modified phosphorous acid esters acrylate compounds of a kind of fluorocarbon chain and its preparation method and application
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CN105339375A (en) 2013-07-08 2016-02-17 巴斯夫欧洲公司 Liquid bisacylphosphine oxide photoinitiator

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ATE496928T1 (en) * 2004-11-23 2011-02-15 Basf Se BISACYLPHOSPHANES AND THEIR USE AS PHOTOINITIATORS, PROCESS FOR PRODUCING ACYLPHOSPHANES
JP5515070B2 (en) * 2010-06-30 2014-06-11 ディーエスエム アイピー アセッツ ビー．ブイ． D1492 liquid BAPO photoinitiator and its use in radiation curable compositions

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US10040810B2 (en) 2012-12-19 2018-08-07 Basf Se Derivatives of bisacylphosphinic acid, their preparation and use as photoinitiators
CN104870456A (en) * 2012-12-19 2015-08-26 巴斯夫欧洲公司 Derivatives of bisacylphosphinic acid, their preparation and use as photoinitiators
CN103333202B (en) * 2013-06-08 2016-09-07 广东博兴新材料科技有限公司 A kind of longwave absorption light trigger of phosphoric acid ester group based on epoxide and preparation method thereof
CN103333202A (en) * 2013-06-08 2013-10-02 广州市博兴化工科技有限公司 Epoxy compound-based phosphate ester-containing long wave light-absorbing initiator and preparation method thereof
CN108779192A (en) * 2016-01-11 2018-11-09 汉高知识产权控股有限责任公司 The compatible compound of organosilicon
KR20180103877A (en) * 2016-01-11 2018-09-19 헨켈 아이피 앤드 홀딩 게엠베하 Silicone-Compatible Compounds
WO2017120743A1 (en) * 2016-01-11 2017-07-20 Henkel IP & Holding GmbH Silicone-compatible compounds
US10597413B2 (en) 2016-01-11 2020-03-24 Henkel Ag & Co. Kgaa Silicone-compatible compounds
CN108779192B (en) * 2016-01-11 2021-01-26 汉高知识产权控股有限责任公司 Silicone compatible compounds
KR102575896B1 (en) 2016-01-11 2023-09-07 헨켈 아게 운트 코. 카게아아 Silicone-compatible compounds
US10858380B2 (en) 2017-04-03 2020-12-08 Hewlett-Packard Development Company, L.P. Photo active agents
CN109867693A (en) * 2019-01-08 2019-06-11 广东博兴新材料科技有限公司 Modified phosphorous acid esters acrylate compounds of a kind of fluorocarbon chain and its preparation method and application
CN109867693B (en) * 2019-01-08 2021-08-10 广东博兴新材料科技有限公司 Fluorocarbon chain modified phosphite ester acrylate compound and preparation method and application thereof

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