CN1321100C - Cation light initiator hydroxy alkoxy substituted diphenyl iodine onium salt and its preparation method - Google Patents
Cation light initiator hydroxy alkoxy substituted diphenyl iodine onium salt and its preparation method Download PDFInfo
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- CN1321100C CN1321100C CNB2005100411175A CN200510041117A CN1321100C CN 1321100 C CN1321100 C CN 1321100C CN B2005100411175 A CNB2005100411175 A CN B2005100411175A CN 200510041117 A CN200510041117 A CN 200510041117A CN 1321100 C CN1321100 C CN 1321100C
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Abstract
The present invention relates to a cationic light initiator, namely hydroxy alkoxy substituted diphenyl iodine onium salt, and a preparation method thereof, which belongs to the technical field of organic synthesis and cationic polymerization. The present invention provides the compound which is named [4-(2-hydroxyl-3-alkoxy-1-propoxy) phenyl] phenyl iodonium salt and is used as a photoinitiator in cationic polymerization. The preparation method comprises: firstly, hydroxyl p-toluenesulfonyl oxy iodobenzene is prepared; then, hydroxyl p-toluenesulfonyl oxy iodobenzene reacts with 1-alkoxy-3-phenoxy propylene glycol; finally, reaction products continue to react with hexafluoro antimony group acid salt to obtain the product of [4-(2-hydroxy-3-alkoxyl-1-propoxy) phenyl] phenyl iodonium-hexafluoro antimony group acid salt. The compound is a cationic light curing initiator with the advantages of simple and convenient preparation and low cost, and have good solubility in nonpolar resin; the introduction of alkoxyl enables the maximum ultraviolet absorption wavelength of iodonium salt to be shifted to 245 nm at the red end of the visible spectrum.
Description
Technical field
The present invention relates to the preparation of the initiator in the cationoid polymerisation, synthesized a series of diphenyl iodnium that have hydroxyl on alkoxy substituted, belong to organic synthesis and cationoid polymerisation technical field.
Background technology
Ultraviolet light polymerization (UV curing) has characteristics such as speed is fast, energy consumption is low, non-environmental-pollution, coating performance excellence.It is the research basis that UV the earliest solidifies with the free radical mechanism, and cationic curing is just to grow up the end of the seventies, compares with radically curing, and the cationic curing system has the following advantages: 1. not by oxygen inhibition; 2. volumetric shrinkage is little during the positively charged ion ring-opening polymerization, and formed coating adhesion is stronger; 3. curing reaction is difficult for stopping, and is applicable to the photocuring of thick film and colored paint.
Diaryl group iodized salt (A) and triaryl sulfonium salts (B) have preferable thermostability, and are easy to synthesize as a kind of cation light initiator commonly used, therefore very fast the and shiploads of merchandiseization of development.
Its maximum shortcoming is to cost an arm and a leg, and the solvability of salt in non-polar resin is not enough.
Summary of the invention
It is simple to the purpose of this invention is to provide a kind of preparation, convenient, the cation photocuring initiator that cost is low.
The objective of the invention is to be achieved through the following technical solutions:
The present invention proposes the compound that a kind of name is called [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene salt compounded of iodine, and its general formula is:
R is that H or R are that alkyl or the R of C=1-14 is allyl group, and X is proton acid type negatively charged ion: SbF
6, AsF
6, PF
6, BF
4, ClO
4, CF
3SO
3, FSO
3, CH
3SO
3Or C
4F
9SO
3This compound is in cationoid polymerisation, as light trigger.
When R be C=4, when alkyl is butyl, X is SbF
6, this compound is [4-(2-hydroxyl-3-butoxy-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate, structural formula is:
When R be C=8, when alkyl is the 2-ethylhexyl, X is SbF
6, this compound is [4-(2-hydroxyl-3-(2-ethylhexyl) Oxy-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate, structural formula is:
When R was allyl group, X was AsF
6, this compound is [4-(2-hydroxyl-3-allyl group Oxy-1-propoxy-) phenyl] benzene iodo-hexafluoro arsenate, structural formula is:
The preparation method of compound [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene salt compounded of iodine is:
(1) makes the diacetyl iodobenzene by phenyl-iodide and superoxol, acetic anhydride, continue reaction with tosic acid again and make product (I) hydroxyl tolysulfonyl oxygen base iodobenzene.Reaction formula is:
Reaction conditions is: add the 0.1mol phenyl-iodide in three-necked flask, 30% superoxol 0.45mol, diacetyl oxide 0.75mol is behind 40 ℃ of stirred in water bath reaction 9h, add tosic acid 0.11mol again, continue reaction 2h under this temperature, white solid is separated out in cooling, suction filtration, with the ether washing, oven dry obtains hydroxyl tolysulfonyl oxygen base iodobenzene.
(2) make product (II) 1-alkoxyl group-3-phenoxy group propan-2-ol by phenol and alkyl glycidyl ether reaction, reaction formula is:
Reaction conditions is: add sodium hydroxide 0.02mol in the 250ml three-necked bottle, alkyl glycidyl ether 0.1mol and phenol 0.11mol, at 120～150 ℃ of following stirring reaction 3～5h, reaction finishes, and reactant cooling back is soluble in water, uses ether extraction, the organic phase NaOH solution washing of 0.1mol/l, use anhydrous magnesium sulfate drying, reclaim solvent, obtain [1-alkoxyl group-3-phenoxy group propan-2-ol].
(3) make product (III) [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-tolysulfonyl oxygen base salt by product (I) and product (II) reaction, reaction formula is:
Reaction conditions is: 0.01mol1-alkoxyl group-3-phenoxy group propan-2-ol is dissolved in 40～50mlCH
2Cl
2In, adding 0.01mol hydroxyl tolysulfonyl oxygen base iodobenzene again, 3～6ml Glacial acetic acid reacts 2～4h down at 40 ℃, and reaction is finished, and rotary evaporation boils off CH
2Cl
2, obtain [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-tolysulfonyl oxygen base salt.
(4) by product (III) and the acid sodium reaction of hexafluoro antimony family, make product (IV) [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-hexaflouroantimonate family salts, reaction formula is:
Reaction conditions is: add 50ml ethanol in the product (III) of gained, add 0.01mol hexafluoro antimony family acid sodium again, stir, generate the paratoluenesulfonic acid sodium salt white precipitate at once.Suction filtration, rotary evaporation boils off ethanol and gets yellow oil, spends the night crystallization.Behind toluene/methylene dichloride recrystallization, get [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-hexaflouroantimonate family salts.
Hexafluoro antimony family acid sodium is NaSbF
6, NaAsF
6Or NaPF
6
Beneficial effect of the present invention: [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene salt compounded of iodine is that a kind of preparation is simple, convenient, the cation photocuring initiator that cost is low, have solvability preferably in non-polar resin, the introducing of alkoxyl group makes the ultraviolet maximum absorption wavelength red shift of salt compounded of iodine to 245nm.
Embodiment
Synthesizing of embodiment 1 hydroxyl tolysulfonyl oxygen base iodobenzene
In three-necked flask, add 0.1mol phenyl-iodide, 30% superoxol 0.45mol, diacetyl oxide 0.75mol, behind 40 ℃ of stirred in water bath reaction 9h, add tosic acid 0.11mol again, under this temperature, continue reaction 2h, cooling, separate out white solid, suction filtration is with ether washing, oven dry, obtain hydroxyl tolysulfonyl oxygen base iodobenzene, productive rate 49%.
Embodiment 2 preparation [4-(2-hydroxyl-3-butoxy-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonates
Add sodium hydroxide 0.02mol, butylglycidyl ether 0.1mol and phenol 0.11mol in the 250ml three-necked bottle.At 130 ℃ of following stirring reaction 4h.Reaction finishes, and reactant cooling back is soluble in water, uses ether extraction.Organic phase is with behind the NaOH solution washing of 0.1mol/l, and anhydrous magnesium sulfate drying reclaims solvent, obtains colourless liquid [1-butoxy-3-phenoxy group propan-2-ol].
0.01mol1-butoxy-3-phenoxy group propan-2-ol is dissolved in 50mlCH
2Cl
2In, add 0.01mol hydroxyl tolysulfonyl oxygen base iodobenzene again, the 4ml Glacial acetic acid.40 ℃ of reactions 2.5 down.Reaction is finished, and rotary evaporation boils off CH
2Cl
2In the pale yellow oily liquid of gained, add 50ml ethanol, add 0.01molNaSbF again
6, stir, generate the paratoluenesulfonic acid sodium salt white precipitate at once.Suction filtration, rotary evaporation boils off ethanol and gets yellow oil, spends the night crystallization.Behind toluene/methylene dichloride recrystallization, get product [4-(2-hydroxyl-3-butoxy-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate.
Embodiment 3 preparation [4-(2-hydroxyl-3-(2-ethylhexyl) Oxy-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonates
Add sodium hydroxide 0.02mol, 2-ethylhexyl glycidyl ether 0.1mol and phenol 0.11mol in the 250ml three-necked bottle.At 150 ℃ of following stirring reaction 3h.Reaction finishes, and reactant cooling back is soluble in water, uses ether extraction.Organic phase is with behind the NaOH solution washing of 0.1mol/l, and anhydrous magnesium sulfate drying reclaims solvent, obtains colourless liquid [1-(2-ethylhexyl) oxygen base-3-phenoxy group propan-2-ol].
0.01mol1-(2-ethylhexyl) oxygen base-3-phenoxy group propan-2-ol is dissolved in 50mlCH
2Cl
2In, add 0.01mol hydroxyl tolysulfonyl oxygen base iodobenzene again, the 6ml Glacial acetic acid.React 4h down at 40 ℃.Reaction is finished, and rotary evaporation boils off CH
2Cl
2In the pale yellow oily liquid of gained, add 50ml ethanol, add 0.01molNaSbF again
6, stir, generate the paratoluenesulfonic acid sodium salt white precipitate at once.Suction filtration, rotary evaporation boils off ethanol and gets yellow oil, spends the night crystallization.Behind toluene/methylene dichloride recrystallization, get product [4-(2-hydroxyl-3-(2-ethylhexyl) Oxy-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate.
Embodiment 4 preparation [4-(2-hydroxyl-3-allyl group Oxy-1-propoxy-) phenyl] benzene iodo-hexafluoro arsenates
Add sodium hydroxide 0.02mol, glycidyl allyl ether 0.1mol and phenol 0.11mol in the 250ml three-necked bottle.At 120 ℃ of following stirring reaction 5h.Reaction finishes, and reactant cooling back is soluble in water, uses ether extraction.After organic phase was used the 0.1mol/lNaOH solution washing, anhydrous magnesium sulfate drying reclaimed solvent, obtains weak yellow liquid [1-allyl group oxygen base-3-phenoxy group propan-2-ol].
0.01mol1-allyl group oxygen base-3-phenoxy group propan-2-ol is dissolved in 40mlCH
2Cl
2In, add 0.01mol hydroxyl tolysulfonyl oxygen base iodobenzene again, the 3ml Glacial acetic acid.React 2h down at 40 ℃.Reaction is finished, and rotary evaporation boils off CH
2Cl
2In the pale yellow oily liquid of gained, add 50ml ethanol, add 0.01mol NaAsF again
6, stir, generate the paratoluenesulfonic acid sodium salt white precipitate at once.Suction filtration, rotary evaporation boils off ethanol and gets yellow oil, spends the night crystallization.Behind toluene/methylene dichloride recrystallization, get product [4-(2-hydroxyl-3-allyl group Oxy-1-propoxy-) phenyl] benzene iodo-hexafluoro arsenate.
Claims (5)
1. name is called the compound of [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene salt compounded of iodine, and its general formula is:
R is that H or R are that alkyl or the R of C=1-14 is allyl group, and X is: SbF
6, AsF
6, PF
6, BF
4, ClO
4, CF
3SO
3, FSO
3, CH
3SO
3Or C
4F
9SO
3This compound is in cationoid polymerisation, as light trigger.
2. compound according to claim 1, wherein R is a butyl, X is SbF
6, this compound is [4-(2-hydroxyl-3-butoxy-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate, structural formula is:
3. compound according to claim 1, wherein R is the 2-ethylhexyl, X is SbF
6, this compound is [4-(2-hydroxyl-3-(2-ethylhexyl) Oxy-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate, structural formula is:
4. compound according to claim 1, wherein R is an allyl group, X is AsF
6, this compound is [4-(2-hydroxyl-3-allyl group Oxy-1-propoxy-) phenyl] benzene iodo-hexafluoro arsenate, structural formula is:
5. the preparation method of one kind [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate or hexaflouroantimonate family salts is characterized in that:
(1) make the diacetyl iodobenzene by phenyl-iodide and superoxol, acetic anhydride, continue reaction with tosic acid again and make product (I) hydroxyl tolysulfonyl oxygen base iodobenzene, reaction formula is:
Reaction conditions is: add the 0.1mol phenyl-iodide in three-necked flask, 30% superoxol 0.45mol, diacetyl oxide 0.75mol is behind 40 ℃ of stirred in water bath reaction 9h, add tosic acid 0.11mol again, continue reaction 2h under this temperature, white solid is separated out in cooling, suction filtration, with the ether washing, oven dry obtains hydroxyl tolysulfonyl oxygen base iodobenzene;
(2) make product (II) 1-alkoxyl group-3-phenoxy group propan-2-ol by phenol and alkyl glycidyl ether reaction, reaction formula is:
Reaction conditions is: add sodium hydroxide 0.02mol in the 250ml three-necked bottle, alkyl glycidyl ether 0.1mol and phenol 0.11mol, at 120～150 ℃ of following stirring reaction 3～5h, reaction finishes, and reactant cooling back is soluble in water, uses ether extraction, the organic phase NaOH solution washing of 0.1mol/l, use anhydrous magnesium sulfate drying, reclaim solvent, obtain 1-alkoxyl group-3-phenoxy group propan-2-ol;
(3) make product (III) [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-tolysulfonyl oxygen base salt by product (I) and product (II) reaction, reaction formula is:
Reaction conditions is: 0.01mol1-alkoxyl group-3-phenoxy group propan-2-ol is dissolved in 40～50mlCH
2Cl
2In, adding 0.01mol hydroxyl tolysulfonyl oxygen base iodobenzene again, 3～6ml Glacial acetic acid reacts 2～4h down at 40 ℃, and reaction is finished, and rotary evaporation boils off CH
2Cl
2, obtain [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-tolysulfonyl oxygen base salt;
(4) by product (III) and sodium hexafluoroantimonate reaction, make product (IV) [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate, reaction formula is:
Reaction conditions is: add 50ml ethanol in the product (III) of gained, add the 0.01mol sodium hexafluoroantimonate again, stir, generate the paratoluenesulfonic acid sodium salt white precipitate at once, suction filtration, rotary evaporation boils off ethanol and gets yellow oil, spends the night, crystallization gets [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-hexafluoro antimonate behind toluene/methylene dichloride recrystallization;
Used sodium hexafluoroantimonate NaSbF
6, use hexafluoroarsenate sodium NaAsF instead
6Or sodium hexafluoro phosphate NaPF
6Replace, the same process products therefrom is respectively [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-hexafluoro arsenate or [4-(2-hydroxyl-3-alkoxyl group-1-propoxy-) phenyl] benzene iodo-hexafluorophosphate.
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| CN101121695B (en) * | 2007-09-06 | 2011-05-11 | 苏州大学 | Method for preparing nitrogen-containing onium salt compounds |
| CN109879783A (en) * | 2019-01-11 | 2019-06-14 | 河南清水源科技股份有限公司 | A kind of water-soluble fluorescent monomer, water soluble fluorescence tracer type water treatment agent and preparation method thereof |
| CN114315531A (en) * | 2021-12-31 | 2022-04-12 | 宁波南大光电材料有限公司 | Photosensitizer with high photosensitive activity and preparation method thereof |
| CN116675628A (en) * | 2023-05-10 | 2023-09-01 | 南通新纳希新材料有限公司 | Novel iodonium salt purification method |
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| US5144051A (en) * | 1990-05-29 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Branched alkoxyphenyl iodonium salt photoinitiators |
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2005
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Patent Citations (8)
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| US5144051A (en) * | 1990-05-29 | 1992-09-01 | Minnesota Mining And Manufacturing Company | Branched alkoxyphenyl iodonium salt photoinitiators |
| US5079378A (en) * | 1990-07-27 | 1992-01-07 | Polyset Corporation | Preparation of diaryliodonium salt photoinitiators having long chain ester groups concatenated with aryl groups |
| CN1080740C (en) * | 1996-04-26 | 2002-03-13 | 国际壳牌研究有限公司 | UV curable composition |
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| US6632960B2 (en) * | 2002-06-21 | 2003-10-14 | Goldschmidt Ag | Diaryliodonium salt catalysts made from iodotoluene and a method for preparing them |
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