CN103525178A - Application of aluminum salt compound as polymerization inhibitor - Google Patents

Application of aluminum salt compound as polymerization inhibitor Download PDF

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Publication number
CN103525178A
CN103525178A CN201210224085.2A CN201210224085A CN103525178A CN 103525178 A CN103525178 A CN 103525178A CN 201210224085 A CN201210224085 A CN 201210224085A CN 103525178 A CN103525178 A CN 103525178A
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hydrogen atom
application
stopper
alkyl
compound
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赵文超
麻忠利
张卓
张珏
姚丽秀
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Yingli Science And Technology Development Co Ltd Beijing
INSIGHT HIGH TECHNOLOGY (TIANJIN) Co Ltd
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Yingli Science And Technology Development Co Ltd Beijing
INSIGHT HIGH TECHNOLOGY (TIANJIN) Co Ltd
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Abstract

The invention relates to application of a compound shown by a structural formula (I) in the specification as a polymerization inhibitor. The compound serving as the polymerization inhibitor has the advantages of no release of benzene, good storage stability, good polymerization inhibiting performance and the like, and can be used for benzene-free UV (Ultraviolet) printing ink.

Description

A kind of aluminium salt compound is as the application of stopper
Technical field
The present invention relates to a kind of three [N-nitroso-group-N-(substituted-phenyl) azanol] aluminium salt compound, as the application of structure formula I compound as stopper.
Background technology
Stopper is the material that can stop Raolical polymerizable, and conventional stopper has phenols, ketone, arylamine class, arene nitro compound etc.Three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt is that UV solidifies the conventional a kind of high-efficiency polymerization inhibitor in field, it share and can prevent the auto-polymerization in production, storage process containing unsaturated double-bond compound such as Acrylic Acid Monomer, prepolymer separately or with other key element, and for example Japanese kokai publication hei 8-311079 patent is just combined it use in the heating synthetic reaction process of organic silicon acrylic ester with oxygen; Also can prevent that UV coating, ink formulations product from auto-polymerization reaction, the period of storage that effectively extends UV coating, ink formulations, for example disclosed scheme of CN102208559A patent P11 occurring in storage process.This good product performance, Application Areas is wide.But development and maturation along with the curing art of UV; in order to meet the requirement of human health and environment protection increasingly stringent; countries in the world have been formulated more strict chemical producting safety Performance Evaluation and control regime successively; require exploitation and use out various more high-performance, more environmental protection, more healthy product innovation; prevent the migration of noxious chemical itself or the harm that volatilization brings human health and environment; and benzene is as raw material or the main composition of existing numerous products; it is confirmed as serious carcinogenic substance by expert, especially the strict object of controlling.Find that after deliberation three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt in use can discharge free benzene molecular, this disadvantageous factor, is restricted its application in a lot of fields, as the pattern and character printing on Cigarette pack.
Summary of the invention
Three the invention provides a kind of aluminium salt compound, [N-nitroso-group-N-(substituted-phenyl) azanol] aluminium salt is as application and the synthetic method thereof of stopper, and aluminium salt compound is as shown in structure formula I.
Figure BDA00001841345700011
Wherein, R 1, R 2, R 3, R 4, R 5independently hydrogen atom, C separately 1-C 12alkyl, C 1-C 12alkoxyl group, with optional OH and/or OR 6the C replacing 2-C 40alkoxyl group, the C interrupting with one or more O 2-C 40alkoxyl group, CN, CF 3, F, Cl, Br, phenyl, substituted-phenyl; R wherein 6for C 1-C 12alkyl, cyclohexyl, phenyl, substituted-phenyl; R 1, R 2, R 3, R 4, R 5when different, are hydrogen atoms; Or R 1, R 2, R 5be hydrogen atom, R 3, R 4form propylidene, butylidene or benzo base; Or R 1, R 2, R 3be hydrogen atom, R 4, R 5form benzo base.
Aluminium salt compound provided by the present invention, as shown in structure formula I, wherein, R 1, R 2, R 3, R 4, R 5independently H, C separately 1-C 12alkyl, with optional OH and/or OR 6the C replacing 2-C 40alkoxyl group, the C interrupting with one or more O 2-C 40alkoxyl group; R wherein 6for C 1-C 12alkyl; R 1, R 2, R 3, R 4, R 5when different, are hydrogen atoms; Or R 1, R 2, R 5be hydrogen atom, R 3, R 4form benzo base; Or R 1, R 2, R 3be hydrogen atom, R 4, R 5form benzo base.
Above-mentioned aluminium salt compound provided by the present invention, as shown in structure formula I, wherein, R 1, R 2, R 3, R 4, R 5independently hydrogen atom, C separately 1-C 12alkyl; R 1, R 2, R 3, R 4, R 5when different, are hydrogen atoms.
Aluminium salt compound compound provided by the present invention, as shown in structure formula I, wherein, R 1c 1-C 12alkyl, R 2, R 3, R 4, R 5it is hydrogen atom; Or R 2c 1-C 12alkyl, R 1, R 3, R 4, R 5it is hydrogen atom; Or R 3c 1-C 12alkyl, R 1, R 2, R 4, R 5it is hydrogen atom.
Aluminium salt compound compound provided by the present invention, as shown in structure formula I, wherein, R 1methyl, R 2, R 3, R 4, R 5it is hydrogen atom; Or R 2methyl, R 1, R 3, R 4, R 5hydrogen; Or R 3methyl, R 1, R 2, R 4, R 5it is hydrogen atom.
Aluminium salt compound compound provided by the present invention, as shown in structure formula I, wherein, R 3methyl, R 1, R 2, R 4, R 5it is hydrogen atom.
Provided by the invention three [N-nitroso-group-N-(substituted-phenyl) azanol] aluminium salt compound can be used as stopper and is applied to UV and solidifies field, the especially stopper of UV ink composite product shelf stability.With three (N-nitroso-group-N-Phenylhydroxylamine aluminium salt is compared, and has the advantages that not discharge benzene molecular, can be used for without in benzene UV ink.
The invention provides a kind of synthetic method of structure formula I compound, with containing substituent oil of mirbane (structural formula a compound), it is starting raw material, through reduction, obtain corresponding substituted-phenyl azanol, reductive agent can be used zinc powder/ammonium chloride/alcohol water, magnesium powder/ammonium chloride/alcohol water or other hydrogen supply reduction systems, the reduction of preferably magnesium powder/ammonium chloride/alcohol-water system, the selectivity of body series azanol is high, and yield is high; Wherein alcohol can be used methyl alcohol, ethanol, n-propyl alcohol, Virahol or propyl carbinol.Substituted-phenyl azanol (structural formula b compound) is dissolved in organic solvent, pass into saturated ammonia, react with nitrous acid ester, obtain N-nitroso-group-N-(substituted-phenyl) azanol (structural formula c compound), wherein solvent can be used the ether solvents such as ether, isopropyl ether, methyl tertiary butyl ether, also available benzene, toluene, chlorobenzene, methylene dichloride, ethylene dichloride equal solvent.N-nitroso-group-N-(substituted-phenyl) azanol reacts in buffered soln with inorganic aluminate and obtains product three [N-nitroso-group-N-(substituted-phenyl) azanol] aluminium salt, and crude product can carry out crystallization as solvent by alcohols.Buffered soln used can be NaAc_HAc buffer solution, SODIUM PHOSPHATE, MONOBASIC-disodium hydrogen phosphate buffer solution or boric acid-sodium borate buffer solution, preferably phosphoric acid sodium dihydrogen-disodium hydrogen phosphate buffer solution, the pH value scope 4.0-7.0 of reaction, preferable range 5.0-6.0; Inorganic aluminate used can be aluminum chloride, Tai-Ace S 150, aluminum nitrate or Aluctyl; Extraction solvent can be used methylene dichloride, ethylene dichloride or chloroform, preferably methylene dichloride; Recrystallisation solvent can be used methyl alcohol, ethanol, n-propyl alcohol or Virahol.Reaction formula is as follows:
Figure BDA00001841345700031
Structure formula I aluminium salt provided by the present invention three [N-nitroso-group-N-(substituted-phenyl) azanol] aluminium salt is compared as stopper and three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt, in the stability contrast experiment of compound, preferred three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol] aluminium salt is more stable, not xanthochromia.In the stability in storage experiment of ink formulations, (N-nitroso-group-N-Phenylhydroxylamine aluminium salt is suitable for the polymerization inhibition performance and three of preferred three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol] aluminium salt.Therefore three benzene in the detection of ink benzene residual quantity, do not detected, [N-nitroso-group-N-(substituted-phenyl) azanol] aluminium salt can be used for without in benzene UV ink, has overcome the benzene molecular release And Spread of Solute that uses three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt to occur.
Specific embodiment
Embodiment 1 N-nitroso-group-N-(4-aminomethyl phenyl) preparation of azanol ammonium salt
Under nitrogen protection, in 250ml there-necked flask, add 20g(0.146mol) 4-nitrotoluene, ammonium chloride 9.15g(0.171mol), 150ml water, stirring and dissolving, adds 36g(0.551mol) Zn powder, when reinforced, control temperature of reaction at 60-70 ℃.Stirring reaction after reinforced end.React complete, filter, filtrate makes it to become saturated salt solution with sodium-chlor, add extracted with diethyl ether, after diethyl ether solution is dry, be cooled to 0 ℃, pass into dry ammonia, after approximately 15 minutes, drip freshly prepd 17g(0.165mol) butyl nitrite, control temperature below 10 ℃, drip and finish the logical ammonia stirring reaction of rear continuation, filtration washing obtains white plates crystallization 17.8g, yield 72.3%, fusing point: 148.2-150.3 ℃.
The preparation of embodiment 2 three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol] aluminium salt
In the 50ml of dried and clean there-necked flask, add N-nitroso-group-N-(4-aminomethyl phenyl) azanol ammonium salt 8.0g, add deionized water 20g, methylene dichloride 20g, adds the buffered soln 8g that pH value is 5.0-6.0; Stirring at normal temperature drips aluminum nitrate aqueous solution 9g(3g nine water aluminum nitrates and is dissolved in 6g deionized water), dropwise stirring reaction, react complete, standing separatory, deionized water wash, separatory; Organic phase Distillation recovery methylene dichloride, adds ethanol stirring and crystallizing to obtain white solid, filters, the dry 6.96g, yield 92% of obtaining.Content 99.79%, fusing point: 142.4-144.9 ℃. 1h-NMR data δ 2.4037ppm (s, 3H, CH 3); 7.2489,7.2764ppm (d, 2H, Ar); 7.8815,7.9088ppm (d, 2H, Ar).
The preparation of embodiment 3 N-nitroso-group-N-(2-aminomethyl phenyl) azanol ammonium salt
Under nitrogen protection, in 250ml there-necked flask, add 20g(0.146mol) 2-nitrotoluene, ammonium chloride 9.15g(0.171mol), 150ml water, stirring and dissolving adds 36g(0.551mol in batches) Zn powder, when reinforced, control temperature of reaction at 60-70 ℃.Stirring reaction after reinforced end, reaction finishes.Filter, filtrate is saturated with sodium-chlor, add extracted with diethyl ether, after ether dissolution anhydrous sodium sulfate drying, be cooled to 0 ℃, pass into dry ammonia, after approximately 15 minutes, drip freshly prepd 17g(0.165mol) butyl nitrite, control temperature below 10 ℃, drip and finish the logical ammonia stirring reaction of rear continuation half an hour.Filtration washing obtains white plates crystallization 9.2g, fusing point: 98.8-109.8 ℃.
The preparation of embodiment 4 three [N-nitroso-group-N-(2-aminomethyl phenyl) azanol] aluminium salt
In the 50ml of dried and clean there-necked flask, add N-nitroso-group-N-(2-aminomethyl phenyl) azanol ammonium salt 8.0g, add deionized water 20g, methylene dichloride 20g, adds the buffered soln 8.0g that pH value is 5.0-6.0; Stirring at normal temperature drips aluminum nitrate aqueous solution 9.0g (3.0g nine water aluminum nitrates are dissolved in 6g deionized water), dropwises and stirs 3 hours; Stir complete, standing separatory, organic phase is used deionized water wash successively, organic phase distilled dichloromethane adds ethanol stirring and crystallizing to obtain white solid, filters, the dry 4.26g product that obtains.Content 99.23%, fusing point: 90.3-137.1 ℃.
Embodiment 5 N-nitroso-group-N-(3-aminomethyl phenyls) preparation of azanol ammonium salt
Under nitrogen protection, in 250ml there-necked flask, add 20g(0.146mol) 3-nitrotoluene, ammonium chloride 9.15g(0.171mol), 150ml water, stirring and dissolving adds 36g(0.551mol in batches) Zn powder, when reinforced, control temperature of reaction at 60-70 ℃.Stirring reaction after reinforced end, reaction finishes.Filter, filtrate is saturated with sodium-chlor, add extracted with diethyl ether, after ether dissolution anhydrous sodium sulfate drying, be cooled to 0 ℃, pass into dry ammonia, after approximately 15 minutes, drip freshly prepd 17g(0.165mol) butyl nitrite, control temperature below 10 ℃, drip and finish the logical ammonia stirring reaction of rear continuation half an hour.Filtration washing obtains white plates crystallization 11.34g, fusing point: 128.3-130.8 ℃.
The preparation of embodiment 6 three [N-nitroso-group-N-(3-aminomethyl phenyl) azanol] aluminium salt
In the 50ml of dried and clean there-necked flask, add N-nitroso-group-N-(3-aminomethyl phenyl) azanol ammonium salt 8.0g, add deionized water 20g, methylene dichloride 20g, adds the buffered soln 8.0g that pH value is 5.0-6.0; Stirring at normal temperature drips aluminum nitrate aqueous solution 9.0g (3.0g nine water aluminum nitrates are dissolved in 6g deionized water), dropwises and stirs 3 hours; Stir complete, standing separatory, organic phase is used deionized water wash successively, organic phase distilled dichloromethane adds ethanol stirring and crystallizing to obtain white solid, filters, and dryly obtains 4.92g product, content 99.04%, fusing point: 118.4-119.4 ℃.
Embodiment 7 three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol] the polymerization inhibition performance evaluation contrast in ink product of aluminium salt and three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt
Sample preparation:
In the yellow UV ink of sample a:50g, add 0.1g tri-[N-nitroso-group-N-(4-aminomethyl phenyl) azanol] aluminium salt;
In the yellow UV ink of sample b:50g, add 0.1g tri-(N-nitroso-group-N-Phenylhydroxylamine) aluminium salt;
In the yellow UV ink of sample c:50g, do not add any stopper.
Three samples use respectively 50ml glass sample bottled good, and the sample bottle that installs ink is positioned in 60 ℃ of baking ovens of constant temperature, and whether have gel phenomenon occur, thereby evaluate its storage stability if observing ink.The time that gelation occurs more illustrates that ink storage stability is poorer.Through the insulations of continuous 12 days, place experiment, within 2 days, observe afterwards and survey with glass rod: sample a and sample b do not find gelation, the whole gelations of sample c; Continue to observe the 12nd day, the bottle wall of sample a and sample b has a small amount of gelation.Experimental result is in Table 1
Table 1
Figure BDA00001841345700051
The experimental result of table 1 shows, of the present invention three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol], and aluminium salt and three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt has all shown good polymerization inhibition performance, and both polymerization inhibition effects are identical.
Embodiment 8
The benzene content analysis of three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol] aluminium salt and three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt
Sample preparation: sample 1: accurately take three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt sample 0.0357g in 20ml head space bottle, then add 2ml vanay; Sample 2: accurately take sample three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol] aluminium salt 0.0365g in 20ml head space bottle, then add 2ml vanay.
Plant and instrument: Agilent G1888 head-space sampler, Agilent 7890A gas chromatograph install HP-5 capillary column (30m * 0.32mm * 0.25 μ m), two lamp 2000W of photo solidification machine additional.
Analytic process: after sample prepares, directly carry out headspace sampling analysis, analytical results is in Table 2.
Table 2
Compound Benzene content before illumination Benzene content after illumination
Three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt 55ppm 102ppm
Three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol] aluminium salt Do not detect Do not detect
The analytical results of table 2 shows, in the sample of three (N-nitroso-group-N-Phenylhydroxylamine) aluminium salt, detects benzene content 55ppm; In provided by the invention three [N-nitroso-group-N-(4-aminomethyl phenyl) azanol] aluminium salt sample, do not detect benzene (detectability 0.003ppm).

Claims (9)

1. structure formula I aluminium salt compound is as an application for stopper,
Figure FDA00001841345600011
Wherein, R 1, R 2, R 3, R 4, R 5independently hydrogen atom, C separately 1-C 12alkyl, C 1-C 12alkoxyl group, with optional OH and/or OR 6the C replacing 2-C 40alkoxyl group, the C interrupting with one or more O 2-C 40alkoxyl group, CN, CF 3, F, Cl, Br, phenyl, substituted-phenyl; R wherein 6for C 1-C 12alkyl, cyclohexyl, phenyl, substituted-phenyl, but R 1, R 2, R 3, R 4, R 5when different, are hydrogen atoms; Or R 1, R 2, R 5be hydrogen atom, R 3, R 4form propylidene, butylidene or benzo base; Or R 1, R 2, R 3be hydrogen atom, R 4, R 5form benzo base.
2. structure formula I compound according to claim 1 is as the application of stopper, wherein, and R 1, R 2, R 3, R 4, R 5independently H, C separately 1-C 12alkyl, with optional OH and/or OR 6the C replacing 2-C 40alkoxyl group, the C interrupting with one or more O 2-C 40alkoxyl group; R wherein 6for C 1-C 12alkyl; But R 1, R 2, R 3, R 4, R 5when different, are hydrogen atoms; Or R 1, R 2, R 5be hydrogen atom, R 3, R 4form benzo base; Or R 1, R 2, R 3be hydrogen atom, R 4, R 5form benzo base.
3. structure formula I compound according to claim 2 is as the application of stopper, wherein, and R 1, R 2, R 3, R 4, R 5independently H, C separately 1-C 12alkyl; But R 1, R 2, R 3, R 4, R 5when different, are hydrogen atoms.
4. structure formula I compound according to claim 3 is as the application of stopper, wherein, and R 1c 1-C 12alkyl, R 2, R 3, R 4, R 5it is hydrogen atom; Or R 2c 1-C 12alkyl, R 1, R 3, R 4, R 5hydrogen; Or R 3c 1-C 12alkyl, R 1, R 2, R 4, R 5it is hydrogen atom.
5. structure formula I compound according to claim 4 is as the application of stopper, wherein, and R 1methyl, R 2, R 3, R 4, R 5it is hydrogen atom; Or R 2methyl, R 1, R 3, R 4, R 5it is hydrogen atom; Or R 3methyl, R 1, R 2, R 4, R 5it is hydrogen atom.
6. structure formula I compound according to claim 5 is as the application of stopper, wherein, and R 3methyl, R 1, R 2, R 4, R 5it is hydrogen atom.
7. the structure formula I compound application in UV curing composition as stopper as described in one of claim 1-6.
Structure formula I compound as described in one of claim 1-6 as stopper in the application without in benzene UV ink.
9. the synthetic method of a structure formula I aluminium salt compound, the structural formula (a) of take is raw material, through reduction, obtain corresponding structural formula (b), structural formula (b) reacts with nitrous acid ester and obtains structural formula (c), structural formula (c) reacts with inorganic aluminate and obtains product structure formula I compound, reaction formula is as follows
Figure FDA00001841345600021
Wherein, R 1-R 5definition described in claim 1.
CN201210224085.2A 2012-07-02 2012-07-02 Application of aluminum salt compound as polymerization inhibitor Pending CN103525178A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113150604A (en) * 2021-03-16 2021-07-23 上海抚佳精细化工有限公司 Printing ink and preparation method and application thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08311079A (en) * 1995-05-18 1996-11-26 Toagosei Co Ltd Production of gamma-(meth)acryloxyropylsilane compound
JP2007077038A (en) * 2005-09-12 2007-03-29 Teruo Kutsuma Method for producing crystalline n-nitroso-n-phenylhydroxylamine aluminum salt

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08311079A (en) * 1995-05-18 1996-11-26 Toagosei Co Ltd Production of gamma-(meth)acryloxyropylsilane compound
JP2007077038A (en) * 2005-09-12 2007-03-29 Teruo Kutsuma Method for producing crystalline n-nitroso-n-phenylhydroxylamine aluminum salt

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113150604A (en) * 2021-03-16 2021-07-23 上海抚佳精细化工有限公司 Printing ink and preparation method and application thereof

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Application publication date: 20140122