CN106554430A - A kind of acylphosphanes light trigger - Google Patents
A kind of acylphosphanes light trigger Download PDFInfo
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- CN106554430A CN106554430A CN201610442542.3A CN201610442542A CN106554430A CN 106554430 A CN106554430 A CN 106554430A CN 201610442542 A CN201610442542 A CN 201610442542A CN 106554430 A CN106554430 A CN 106554430A
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- alkyl
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- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- -1 3-C5Thiazolinyl Chemical group 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000007711 solidification Methods 0.000 claims description 5
- 230000008023 solidification Effects 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 6
- 230000005855 radiation Effects 0.000 abstract description 5
- 239000011347 resin Substances 0.000 abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 5
- 239000000178 monomer Substances 0.000 abstract description 4
- 238000006116 polymerization reaction Methods 0.000 abstract description 4
- 238000013508 migration Methods 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 3
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 11
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- FZRCKLPSHGTOAU-UHFFFAOYSA-N 6-amino-1,4-dimethylcyclohexa-2,4-diene-1-carbaldehyde Chemical compound CC1=CC(N)C(C)(C=O)C=C1 FZRCKLPSHGTOAU-UHFFFAOYSA-N 0.000 description 3
- 208000035126 Facies Diseases 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000004807 desolvation Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- UDUIPQVSFOXFMI-UHFFFAOYSA-N bis(2-chloroethoxy)phosphane Chemical class ClCCOPOCCCl UDUIPQVSFOXFMI-UHFFFAOYSA-N 0.000 description 2
- AWYDVYYDVPFOMZ-UHFFFAOYSA-N dichloromethylphosphane Chemical class PC(Cl)Cl AWYDVYYDVPFOMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C07F9/3241—Esters of arylalkanephosphinic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The invention discloses a kind of acylphosphanes light trigger as depicted and preparation method thereof; the difunctional acylphosphanes light trigger has macromolecular structure; eliminate the animal migration during light trigger use; improve the phenomenon of xanthochromia; significantly tertiary amine structure has been coupled on such compound aromatic ring; so that uv absorption red shift of wavelength can effectively cause polymerization of unsaturated monomers to 380nm 395nm under the radiation of UV LEDs；In addition, dissolubility of such compound in various types of resins and its oligomer is good, it is a kind of new macromole acylphosphanes light trigger.
Description
Technical field
The present invention relates to a kind of acylphosphanes light trigger and preparation method thereof, specifically one kind can be suitably used for UV-LED solidifications
Light trigger and preparation method thereof.
Technical background
At present, photocuring technology mainly still adopts ultraviolet light polymerization, ultraviolet source major part still to adopt high voltage mercury lamp；
There are some obvious shortcomings in high voltage mercury lamp solidification：
Power is big, big using process thermal discharge, needs strong cooling medium；
High energy consumption in solidification process；
Starting time length, preheating are slow；
Base material is had high demands；
There is mercury pollution.
Emerging UV-LED light sources compare high voltage mercury lamp obvious advantage：
Cold light source, power are little, energy consumption is low, substrate applications scope is wide；
Plug and play, without the need for preheating；
Stable output power, can be worked for a long time；
UV-LED light sources cause its making in curing field because of characteristics such as which is green, environmental protection, energy consumption are low, luminous efficiency is high
With more and more extensively, in the long run, it is necessarily becoming for industry development to replace high voltage mercury lamp to carry out photocuring with UV-LED light sources
Gesture.But, the single characteristic of UV-LED radiation of light source crests (main wavelength is in 365nm, 395nm) also defines alternative
Light trigger species, in existing light trigger product, only acylphosphanes, thiaxanthone, three kinds of light triggers of amino ketones are in UV-LED
There is absorption in radiated wavelength range, but there is also that absorption is weak, need to improve the shortcoming of initiator addition.
In sum, develop a kind of light for having stronger absorption, high efficiency of initiation, low VOC emission under UV-LED radiation to draw
Send out the big current demand that agent is still photocuring industry instantly.
The compound that a class meets the present invention of above-mentioned requirements is we have found, such compound contains difunctionality unity
Structure, while high initiating activity is ensured, greatly reduces the animal migration during acylphosphanes use, improves showing for xanthochromia
As significantly such compound has stronger absorption under UV-LED light sources, can have under the radiation of UV-LED light sources
The initiation resin monomer polymerization of effect；In addition, dissolubility of such compound in various types of resins and its oligomer is good, be it is a kind of very
Good crack type photoinitiator.
The content of the invention
The present invention provides a kind of acylphosphanes light trigger, and its molecular structure is as follows：
Wherein,
R1, R2Can be single substituted radical or R1With R2The rear and N atoms that are connected collectively form cyclic substituents group；
R1, R2For independent substituted radical when can be independently each C1-C12Alkyl, C3-C5Thiazolinyl, C5-C12Cycloalkyl,
Unsubstituted phenyl or by halogen, C1-C12Alkyl, C1-C4Alkoxyl or-COO (C1-C4Alkyl) phenyl that replaces；It is described
C1-C12Alkyl also can be by OH, SH, C1-C4Alkoxyl, CN, halogen or-COO (C1-C4Alkyl) replaced, R1, R2Can be respective
It is identical, it is also possible to different.
R1, R2It is C jointly when connected3-C7Alkylidene, the alkylidene can be introduced into-O- ,-S- ,-CO-, or-N (R4)-and
The C3-C7Alkylidene can be by OH, SH, C1-C4Alkoxyl, CN, halogen or-COO (C1-C4Alkyl) replaced.
R3Can be H, C1-C6Alkyl, C1-C6Alkoxyl, halogen.
R4For C1-C6Alkyl, C1-C6Alkoxyl, unsubstituted phenyl or by halogen, C1-C12Alkyl, C1-C4
Alkoxyl or-COO (C1-C4Alkyl) phenyl that replaces；The C1-C6Alkyl by OH, SH, C1-C4Alkoxyl, CN, halogen or-
COO(C1-C4Alkyl) replaced.
Light trigger shown in formula [I], it is characterised in that it can be used for UV-LED solidifications.
Present invention also offers the preparation method of formula [I] initiator, its concrete preparation process is：
(1) in a solvent and in the presence of catalyst, react with active metal by raw material of organic phosphorus halide [II], generate
Formula [II a] compound, such as following formula react：
(2) and then with the aliphatic alcohol containing active hydrogen react production [II b] compound：
(3) and then respectively with fragrant aldehyde reaction production [I a] compound shown in formula [III]：
(4) after the completion of reaction (3) after purification of products, with compound shown in oxidant effect formula [I]：
Wherein R1, R2, R3,R4Meaning is identical with formula [I], and X is chlorine or bromine, and M is active metal.
Preferably, the aromatic aldehyde shown in formula [III] includes following compound, but is not limited only to following compound：
Preferably, include following structure with formula [I] compound, but be not limited only to these compounds：
Light trigger of the present invention has the prominent advantages that：
(1) the characteristics of macromolecular photoinitiator of the present invention has low migration, low volatility, odorlessness, low-yellowing, difunctionality
The structure of group ensure that its initiating activity is suitable with the acylphosphanes light trigger of small molecule.
(2) in the molecular structure of light trigger of the present invention, aromatic ring has coupled tertiary amine structure, and strong conjugation causes to absorb ripple
Long red shift, has relatively strong absorption under UV-LED radiation wavelengths, can effectively produce free radical and cause resin monomer rapid polymerization.
(3) light trigger of the present invention dissolubility in various types of resins monomer, oligomer, diluent is good, and trigger rate is fast, especially
Which is applied to the surface cure of coating, ink etc..
Description of the drawings
Infrared spectrum of the figure one for P6511 products prepared by embodiment 1
Specific embodiment
The following example describes the present invention in detail, but example below is not limited only to the present invention again.
Embodiment 1：The preparation of light trigger P6511
A, P is carried out under the conditions of 98 DEG C -100 DEG C in toluene, the metal of bis- chloroethoxy phosphines of P- replaces
Under atmosphere of inert gases, at room temperature sodium block (9.2g, 0.4mol) is suspended in toluene (500ml), is warming up to
Backflow, starts strong agitation when temperature reaches 98 DEG C, is dispersed into Deca P after the droplet of sodium, bis- chloroethoxy phosphines of P-
(14.7g, 0.1mol) more than one hours, then reaction 16h is heated at reflux, yellow suspension thing is formed, it is not purified directly to carry out down
Step reaction.
B, protonation
The tert-butyl alcohol (14.8g 0.2mol) is added dropwise under the conditions of 98 DEG C -100 DEG C in above-mentioned yellow suspension thing, is flowed back
Reaction is complete up to sodium total overall reaction, and product is not required to purification and directly carries out the next step.
C, condensation
Addition paradime thylaminobenzaldehyde (29.8g, 0.2mol) in the reactant liquor of b, Deca triethylamine (20.2g,
0.2mol), normal-temperature reaction 4h, after the completion of TLC detection reactions, desolvation is recrystallized to give binary benzyl alcohol intermediate 25.6g,
Yield 68%.
D, oxidation
Gained intermediate (25.6g, 68mmol), activity MnO in C2(59.2g, 680mmol) is in the dichloromethane of 500ml
In, reaction 18h is stirred at room temperature, TLC monitoring reaction process is filtered after reaction completely, and organic faciess are concentrated to give crude product, toluene weight
Light trigger P6511 (22.95g, product content are obtained after crystallization, drying：97.8%), product yield 87.2%.
Embodiment 2：The preparation of light trigger P6512
A, P is carried out under the conditions of 98 DEG C -100 DEG C in toluene, the metal of P- dichlorophenyl phosphines replaces
Under atmosphere of inert gases, at room temperature sodium block (9.2g, 0.4mol) is suspended in toluene (500ml), is warming up to
Backflow, starts strong agitation when temperature reaches 98 DEG C, is dispersed into Deca P after the droplet of sodium, P- dichlorophenyl phosphines (17.8g,
0.1mol) more than one hours, then reaction 16h is heated at reflux, yellow suspension thing is formed, it is not purified directly to carry out the next step.
B, protonation
The tert-butyl alcohol (14.8g 0.2mol) is added dropwise under the conditions of 98 DEG C -100 DEG C in above-mentioned yellow suspension thing, is flowed back
Reaction is complete up to sodium total overall reaction, and product is not required to purification and directly carries out the next step.
C, condensation
Addition paradime thylaminobenzaldehyde (29.8g, 0.2mol) in the reactant liquor of b, Deca triethylamine (20.2g,
0.2mol), normal-temperature reaction 4h, after the completion of TLC detection reactions, desolvation is recrystallized to give binary benzyl alcohol intermediate 31.7g,
Yield 77.6%.
D, oxidation
Gained intermediate (31.7g, 77.6mmol), activity MnO in C2(67.5g, 776mmol) is in the dichloromethane of 500ml
In alkane, reaction 18h is stirred at room temperature, TLC monitoring reaction process is filtered after reaction completely, and organic faciess are concentrated to give crude product, toluene
Light trigger P6512 (29.1g, product content are obtained after recrystallization, drying：98.4%)；Yield 89.3%.
Embodiment 3：The preparation of light trigger P6513
A, P is carried out under the conditions of 98 DEG C -100 DEG C in toluene, the metal of P- dichloromethyl phosphines replaces
Under atmosphere of inert gases, at room temperature sodium block (9.2g, 0.4mol) is suspended in toluene (500ml), is warming up to
Backflow, starts strong agitation when temperature reaches 98 DEG C, is dispersed into Deca P after the droplet of sodium, P- dichloromethyl phosphines (11.6g,
0.1mol) more than one hours, then reaction 16h is heated at reflux, yellow suspension thing is formed, it is not purified directly to carry out the next step.
B, protonation
The tert-butyl alcohol (14.8g 0.2mol) is added dropwise under the conditions of 98 DEG C -100 DEG C in above-mentioned yellow suspension thing, is flowed back
Reaction is complete up to sodium total overall reaction, and product is not required to purification and directly carries out the next step.
C, condensation
Addition paradime thylaminobenzaldehyde (29.8g, 0.2mol) in the reactant liquor of b, Deca triethylamine (20.2g,
0.2mol), normal-temperature reaction 4h, after the completion of TLC detection reactions, desolvation is recrystallized to give binary benzyl alcohol intermediate 25.8g,
Yield 74.5%.
D, oxidation
Gained intermediate (25.8g, 74.5mmol), activity MnO in C2(64.8g, 745mmol) is in the dichloromethane of 500ml
In alkane, reaction 18h is stirred at room temperature, TLC monitoring reaction process is filtered after reaction completely, and organic faciess are concentrated to give crude product, toluene
Light trigger P6513 (22.6g, product content are obtained after recrystallization, drying：98.9%), product yield 87.2%.
Claims (5)
1. a kind of acylphosphanes light trigger, its molecular structure are as follows：
Wherein,
R1, R2Can be single substituted radical or R1With R2The rear and N atoms that are connected collectively form cyclic substituents group；
R1, R2For independent substituted radical when can be independently each C1-C12Alkyl, C3-C5Thiazolinyl, C5-C12Cycloalkyl, do not taken
The phenyl in generation or by halogen, C1-C12Alkyl, C1-C4Alkoxyl or-COO (C1-C4Alkyl) phenyl that replaces；The C1-C12
Alkyl also can be by OH, SH, C1-C4Alkoxyl, CN, halogen or-COO (C1-C4Alkyl) replaced, R1, R2Can be each identical,
Can also be different.
R1, R2It is C jointly when connected3-C7Alkylidene, the alkylidene can be introduced into-O- ,-S- ,-CO-, or-N (R4)-and should
C3-C7Alkylidene can be by OH, SH, C1-C4Alkoxyl, CN, halogen or-COO (C1-C4Alkyl) replaced.
R3Can be H, C1-C6Alkyl, C1-C6Alkoxyl, halogen.
R4For C1-C6Alkyl, C1-C6Alkoxyl, unsubstituted phenyl or by halogen, C1-C12Alkyl, C1-C4Alkoxyl
Or-COO (C1-C4Alkyl) phenyl that replaces；The C1-C6Alkyl by OH, SH, C1-C4Alkoxyl, CN, halogen or-COO
(C1-C4Alkyl) replaced.
2. light trigger according to claim 1, it is characterised in that it can be used for UV-LED solidifications.
3., according to claim 1, present invention also offers the preparation method of the initiator, its concrete preparation process is：
(1) in a solvent and in the presence of catalyst, react by raw material of organic phosphorus halide [II] with active metal, production
[II a] compound, such as following formula react：
(2) and then with the aliphatic alcohol containing active hydrogen react production [II b] compound：
(3) and then respectively with fragrant aldehyde reaction production [I a] compound shown in formula [III]：
(4) after the completion of reaction (3) after product separating-purifying, with compound shown in oxidant effect formula [I]：
Wherein R1, R2, R3,R4Meaning is identical with formula [I], and X is chlorine or bromine, and M is active metal.
4. the preferably following compound of aromatic aldehyde according to claim 3, shown in formula [III], but it is not limited only to following chemical combination
Thing：
。
5. according to claim 1, structure is preferably as follows with formula [I] compound, but be not limited only to these compounds：
。
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107033185A (en) * | 2017-04-24 | 2017-08-11 | 长沙新宇高分子科技有限公司 | A kind of light trigger, its preparation method and application solidified suitable for LED |
| EP3409680A1 (en) * | 2017-05-30 | 2018-12-05 | IGM Group B.V. | Synthesis of bis(acyl)phosphines by activation of unreactive metal phosphides |
| EP3539969A1 (en) | 2018-03-14 | 2019-09-18 | ETH Zurich | Novel photo-initiators and their application |
| CN110343134A (en) * | 2019-08-04 | 2019-10-18 | 张震 | A kind of preparation method of bis- (2,4,6- trimethylbenzoyl) phenyl phosphine oxides of photoinitiator |
| CN112694548A (en) * | 2020-12-28 | 2021-04-23 | 天津久日新材料股份有限公司 | Acylphosphine oxide photoinitiator and preparation method and application thereof |
| EP4206183A1 (en) * | 2021-12-31 | 2023-07-05 | Arkema France | Polyhydroxylated photoinitiators |
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| JP2012062280A (en) * | 2010-09-16 | 2012-03-29 | Kuraray Medical Inc | Bisacylphosphine oxide compound and polymerizable composition containing the same |
| CN102863848A (en) * | 2012-09-03 | 2013-01-09 | 杭华油墨化学有限公司 | Ultraviolet-light-emitting diode (UV-LED) low-energy cured printing ink |
| CN103980310A (en) * | 2014-05-30 | 2014-08-13 | 天津久日化学股份有限公司 | Preparation method of phenyl bis(2,4,6-trimethylbenzoyl)phosphine oxide |
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