CN104927052A - Method for preparing polyaniline solution in organic solvent - Google Patents
Method for preparing polyaniline solution in organic solvent Download PDFInfo
- Publication number
- CN104927052A CN104927052A CN201510340156.9A CN201510340156A CN104927052A CN 104927052 A CN104927052 A CN 104927052A CN 201510340156 A CN201510340156 A CN 201510340156A CN 104927052 A CN104927052 A CN 104927052A
- Authority
- CN
- China
- Prior art keywords
- organic solvent
- acid
- initiator
- polyaniline solutions
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000767 polyaniline Polymers 0.000 title claims abstract description 55
- 239000003960 organic solvent Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003999 initiator Substances 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 150000007524 organic acids Chemical class 0.000 claims abstract description 6
- 230000005855 radiation Effects 0.000 claims abstract description 6
- 150000001448 anilines Chemical class 0.000 claims abstract description 3
- -1 alkyl carboxylic acid Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000009467 reduction Effects 0.000 abstract description 3
- 150000001451 organic peroxides Chemical class 0.000 abstract 2
- 238000012856 packing Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000010612 desalination reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005054 agglomeration Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- BVWCFOXBDSMXEP-UHFFFAOYSA-N 1-(5-acetyl-2-methoxyphenyl)-3-methylbutan-1-one Chemical compound COC1=CC=C(C(C)=O)C=C1C(=O)CC(C)C BVWCFOXBDSMXEP-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 238000005502 peroxidation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical group CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- AMKPQMFZCBTTAT-UHFFFAOYSA-N 3-ethylaniline Chemical compound CCC1=CC=CC(N)=C1 AMKPQMFZCBTTAT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropyl alcohol Natural products CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- JUMYIBMBTDDLNG-OJERSXHUSA-N hydron;methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;chloride Chemical compound Cl.C([C@@H]1[C@H](C(=O)OC)C=2C=CC=CC=2)CCCN1 JUMYIBMBTDDLNG-OJERSXHUSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940099204 ritalin Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention belongs to the technical field of high molecular material synthesis, and particularly relates to a method for preparing a polyaniline solution in organic solvent. The method includes the steps that 1, monomer aniline or an aniline derivative and organic acid are dissolved in the first organic solvent to obtain monomer organic solvent; 2, an initiator is added into the monomer organic solvent obtained in the step 1, the components react under the condition of ultrasonic wave radiation to obtain the polyaniline solution, or the initiator is dissolved in second organic solvent, the components react under the condition of ultrasonic wave radiation to obtain the polyaniline solution. The method for preparing the polyaniline solution in the organic solvent has the advantages that a reaction system is in full oil phase, and no water is involved. The polyaniline solution obtained through preparation is composed of conductive polyaniline, the solvent and reduction products of organic peroxides, wherein the reduction products of the organic peroxides can be dissolved in the solvent to serve as organic packing, and it is avoided that use in the next step is affected, and performance is reduced.
Description
Technical field
The invention belongs to the synthesis technical field of macromolecular material, particularly relate to a kind of method preparing polyaniline solutions in organic solvent.
Background technology
Paint most at present and ink mostly are oleaginous system, the necessary desalination of polyaniline of the synthesis condition polymerization participated in there being water, dehydration, tretolite, purifying, directly cannot add the paint of oiliness or ink or water-borne coatings, because reaction solution is containing emulsifying agent by the polyaniline liquid that the synthesis condition having water to participate in is polymerized, a large amount of inorganic salt, produce serious disadvantageous effect to paint and coating property.
Summary of the invention
For solving the deficiencies in the prior art: polyaniline aftertreatment can be reunited, twice dispersing is difficult, and waste amount is large, the invention provides a kind of method preparing polyaniline solutions in organic solvent.By the method, the polyaniline solutions that homogeneity is good can be obtained, not need to isolate polyaniline (polyaniline can not be reunited, without waste), just can be directly used in the preparation of the material such as coating and ink.There is good dispersity, step of preparation process is few, can directly be used and avoid the advantages such as polyaniline secondary agglomeration.For the nano application of polyaniline lays the foundation.Do not produce waste.There is environmental protection and energy saving feature.
Prepare a method for polyaniline solutions in organic solvent, comprise the steps:
1) derivative of monomer aniline or aniline and organic acid are dissolved in the first organic solvent, obtain monomer organic solvent.
Concrete, step 1) described in the structural formula of derivative of aniline as follows:
Wherein, R is selected from hydrogen, methyl, ethyl or halogen.Halogen is preferably chlorine or bromine.
Concrete, step 1) described in organic acid be selected from any one or multiple mixing in alkyl benzene sulphonate (ABS), alkylsurfuric acid, alkylphosphonic acid carboxylic acid or alkyl carboxylic acid.
Preferred:
Described alkyl benzene sulphonate (ABS) to be carbonatoms be 2 ~ 18 alkyl or haloalkyl Phenylsulfonic acid;
Described alkylsurfuric acid to be carbonatoms be 2 ~ 18 alkyl or haloalkyl sulfuric acid;
Described alkylphosphonic acid carboxylic acid to be carbonatoms be 2 ~ 18 alkyl or haloalkyl phosphoric acid;
Described alkyl carboxylic acid to be carbonatoms be 2 ~ 18 alkyl or alkylcarboxylic acid.
2) initiator is joined step 1) in the monomer organic solvent that obtains, react under Ultrasonic Radiation condition and under the temperature condition of 0 ~ 30 DEG C, obtain polyaniline solutions, or, initiator is dissolved in the second organic solvent, obtains initiator organic solvent, then initiator organic solvent is mixed with described monomer organic solvent, react under Ultrasonic Radiation condition and under the temperature condition of 0 ~ 30 DEG C again, obtain polyaniline solutions.
Concrete, the reaction times is 24 ~ 48 hours.
Concrete, step 2) described in initiator be organo-peroxide.Organo-peroxide can be selected from acyl class superoxide, hydroperoxide, dialkyl peroxide, ester class superoxide, ketone superoxide, two carbonic ether superoxide or percarboxylic acids any one.
Preferred:
Acyl class superoxide is selected from benzoyl peroxide etc.;
Hydroperoxide are selected from the different phenylpropyl alcohol of hydrogen peroxide etc.;
Dialkyl peroxide is selected from dicumyl peroxide etc.;
Peroxy esters class is selected from any one or multiple mixing in peroxide new enanthic acid 1,1-dimethyl-3-hydroxy butyl ester, peroxidation neodecanoic acid, isopropyl phenyl ester, peroxidation neodecanoic acid tert-pentyl ester, t-butylperoxy pivarate, peroxybenzoic acid tert-pentyl ester or t-butylperoxyl benzoate, t-butyl peroxy ketal or t-amyl peroxy ketal etc.;
Ketone superoxide is selected from methyl ethyl ketone peroxide etc.;
Peroxydicarbonate is selected from 2-ethylhexyl peroxy dicarbonate etc.;
Percarboxylic acids is selected from perbenzoic acid etc.
Above, step 1) described in the first organic solvent be arene, fat hydrocarbon, alicyclic hydrocarbon type, halogenated hydrocarbon, alcohols, ethers, ester class, ketone, alcohol ethers, nitrile or carboxylic-acid with the second described organic solvent, described first organic solvent and described second organic solvent can select identical component, also can select race's different components.
Concrete, arene be selected from benzene,toluene,xylene etc. any one; Fat hydrocarbon be selected from pentane, hexane, octane etc. any one; Alicyclic hydrocarbon type be selected from hexanaphthene, pimelinketone, toluene pimelinketone etc. any one; Halogenated hydrocarbon be selected from chlorobenzene, dichlorobenzene, methylene dichloride etc. any one; Alcohols be selected from methyl alcohol, ethanol, Virahol etc. any one; Ethers be selected from ether, propylene oxide etc. any one; Ester class be selected from ritalin, vinyl acetic monomer, propyl acetate etc. any one; Ketone be selected from acetone, espeleton, mibk etc. any one; Alcohol ethers is diol, derivatives, is selected from any one in ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether etc.; Nitrile is acetonitrile etc.; Carboxylic-acid be selected from formic acid, acetic acid etc. any one.
On the one hand, the feature preparing the method for polyaniline solutions in organic solvent provided by the present invention is not relate to water in reaction system, is full oil phase.The polyaniline solutions prepared by the method preparing polyaniline solutions in organic solvent provided by the present invention consist of electrically conductive polyaniline, solvent, organo-peroxide reduzate.Organo-peroxide reduzate wherein can dissolve in a solvent, as organic filler, does not affect next step and uses and performance reduction.
On the other hand, polymerization polyaniline solutions of the present invention adopts organo-peroxide, and system is saliferous not, emulsifying agent, does not need traditional post-treatment method.Can be applied directly in coating and printing ink making processes and go.Economize the breakdown of emulsion that the polyaniline of the synthesis condition polymerization having water to participate in is necessary, desalination, dehydration, the process of tretolite, solves in breakdown of emulsion desalination, dehydration, in tretolite process, polyaniline must cause reunion, abraum salt, solves polyaniline in the application of polyaniline in paint and ink and is difficult to a difficult problem of disperseing, make the excellent properties of polyaniline be played and embody.
In addition, advantage of the present invention is also embodied in the aspect such as agglomeration and the feature of environmental protection of product.
Agglomeration aspect: original solution polyaniline is liquid state, and the particle diameter 10 ~ 30 microns of powder, meet the requirement of commercial polyaniline.
Feature of environmental protection aspect: traditional synthesis in water per kilogram polyaniline needs ammonium persulfate 3 ~ 6kg, emulsifying agent 0.1 ~ 2.5kg, water 50kg, assistant for emulsifying agent 0.1 ~ 0.5, this synthetic method can not need breakdown of emulsion, desalination, cleaning, reduce abraum salt 3 ~ 6kg, emulsifying agent 0.1 ~ 2.5kg, alcohol 5kg, water 50kg, reduce a large amount of artificial, spillage of material, the energy uses.
Embodiment
Be described principle of the present invention and feature below, example, only for explaining the present invention, is not intended to limit scope of the present invention.Prove the evidence that viewpoint above needs.
Embodiment 1
0.1mol aniline, the Witco 1298 Soft Acid of 0.05mol, add 0.2mol dimethylbenzene, 0.5mol propyl carbinol high speed is stirred in 1000rpm and stirs 30min, until solution clarification, 10min adds the benzoyl peroxide solution (0.1mol benzoyl peroxide is dissolved into 0.3mol propyl carbinol) of 0.1mol, under 100 watts of power ultrasonic effects, react 24 hours, temperature controls at 25 DEG C.The conductive polyaniline solution obtained.Further, if need solid polyaniline, can get conductive polyaniline solution and dry, grinding obtains polyaniline powder.
In other examples, other disclosed in the present invention solvent selected respectively by solvent, and other disclosed in the present invention superoxide selected by initiator, and other reaction conditionss are constant, can obtain polyaniline powder equally.
By the conductive polyaniline solution 10 grams obtained, directly can add same moral vinylformic acid 1260 resin 45 grams and stir evenly, grinding can prepare other multiple products such as electrically conductive polyaniline varnish or ink.This varnish film can wait until the conducting film of 7 powers of 4.5*10.This varnish is according to GB salt mist experiment and blank resin model contrast contrast, and the salt fog time rose to 168 hours from 96 hours, performance boost 70%.
Embodiment 2
0.05mol aniline, adds 2.0mol acetic acid, and 0.03mol dodecyl sulphate adds 0.75mol hydrogen peroxide, high-speed stirring, and temperature controls at 25 DEG C, under 100 watts of hyperacoustic effects, can obtain polyaniline solutions and directly use.
In other examples, select disclosed in the present invention other solvent, organic acid, initiator, other reaction conditionss are constant, can prepare the polyaniline solutions that can directly use equally.
Embodiment 3
0.1mol o-toluidine, the dodecylphosphoric acid of 0.045mol, add 0.2mol dimethylbenzene, 0.5mol propyl carbinol high speed stirs, until solution clarification, drip the benzoyl peroxide solution (0.1mol benzoyl peroxide is dissolved into 0.3mol propyl carbinol) of 0.1mol, under 100 watts of power ultrasonic effects, react 24 ~ 48 hours, temperature controls at 0 ~ 30 DEG C.The solution obtained directly can add resin-made for other products such as coating or ink, can also wait until thick polyaniline by spraying dry, can wait until high-purity polyaniline through absolute ethanol washing.
In other enforcement, monomer selects m-toluidine, open-chain crown ether, o ethyl aniline, m-ethyl aniline, to ethylaniline etc., other reaction conditionss are constant, can prepare high-purity polyaniline equally.
The foregoing is only better embodiment of the present invention, not in order to limit the present invention, within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (7)
1. prepare a method for polyaniline solutions in organic solvent, it is characterized in that, comprise the steps:
1) derivative of monomer aniline or aniline and organic acid are dissolved in the first organic solvent, obtain monomer organic solvent;
2) initiator is joined step 1) in the monomer organic solvent that obtains, react under Ultrasonic Radiation condition and under the temperature condition of 0 ~ 30 DEG C, obtain polyaniline solutions; Or, initiator is dissolved in the second organic solvent, obtains initiator organic solvent, then initiator organic solvent is mixed with described monomer organic solvent, react under Ultrasonic Radiation condition and under the temperature condition of 0 ~ 30 DEG C again, obtain polyaniline solutions.
2. the method preparing polyaniline solutions in organic solvent according to claim 1, is characterized in that, step 1) described in the structural formula of derivative of aniline as follows:
Wherein, R is selected from hydrogen, methyl, ethyl or halogen.
3. the method preparing polyaniline solutions in organic solvent according to claim 1, is characterized in that: step 1) described in organic acid be selected from any one or multiple mixing in alkyl benzene sulphonate (ABS), alkylsurfuric acid, alkylphosphonic acid carboxylic acid or alkyl carboxylic acid.
4. the method preparing polyaniline solutions in organic solvent according to claim 3, is characterized in that:
Described alkyl benzene sulphonate (ABS) to be carbonatoms be 2 ~ 18 alkyl benzene sulphonate (ABS) or carbonatoms be 2 ~ 18 haloalkyl Phenylsulfonic acid;
Described alkylsurfuric acid to be carbonatoms be 2 ~ 18 alkyl or haloalkyl sulfuric acid;
Described alkylphosphonic acid carboxylic acid to be carbonatoms be 2 ~ 18 alkyl or haloalkyl phosphoric acid;
Described alkyl carboxylic acid to be carbonatoms be 2 ~ 18 alkyl or alkylcarboxylic acid.
5. the method preparing polyaniline solutions in organic solvent according to claim 1, is characterized in that: step 2) described in initiator be organo-peroxide.
6. the method preparing polyaniline solutions in organic solvent according to claim 5, is characterized in that: step 2) described in organo-peroxide be acyl class superoxide, hydroperoxide, dialkyl peroxide, ester class superoxide, ketone superoxide, two carbonic ether superoxide or percarboxylic acids.
7., according to the arbitrary described method preparing polyaniline solutions in organic solvent of claim 1 to 6, it is characterized in that:
Step 1) described in the first organic solvent be arene, fat hydrocarbon, alicyclic hydrocarbon type, halogenated hydrocarbon, alcohols, ethers, ester class, ketone, alcohol ethers, nitrile or carboxylic-acid;
Step 1) described in the second organic solvent be arene, fat hydrocarbon, alicyclic hydrocarbon type, halogenated hydrocarbon, alcohols, ethers, ester class, ketone, alcohol ethers, nitrile or carboxylic-acid;
Described first organic solvent and described second organic solvent identical or different.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510340156.9A CN104927052A (en) | 2015-06-18 | 2015-06-18 | Method for preparing polyaniline solution in organic solvent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510340156.9A CN104927052A (en) | 2015-06-18 | 2015-06-18 | Method for preparing polyaniline solution in organic solvent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104927052A true CN104927052A (en) | 2015-09-23 |
Family
ID=54114491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510340156.9A Pending CN104927052A (en) | 2015-06-18 | 2015-06-18 | Method for preparing polyaniline solution in organic solvent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104927052A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1141310A (en) * | 1995-07-27 | 1997-01-29 | 中国科学院长春应用化学研究所 | Preparation of full-soluble polyaniline with different molecular weights and derivatives thereof |
| CN101139440A (en) * | 2007-10-17 | 2008-03-12 | 天津大学 | Preparation method of high-purity nanosheet polyaniline |
| US20080142074A1 (en) * | 2003-10-08 | 2008-06-19 | The Yokohama Rubber Co., Ltd. | Method for producing conductive polyaniline |
| CN101492569A (en) * | 2008-07-01 | 2009-07-29 | 南京理工大学 | Oxidized graphite flake layer/polyaniline composite material and method for preparing the same |
-
2015
- 2015-06-18 CN CN201510340156.9A patent/CN104927052A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1141310A (en) * | 1995-07-27 | 1997-01-29 | 中国科学院长春应用化学研究所 | Preparation of full-soluble polyaniline with different molecular weights and derivatives thereof |
| US20080142074A1 (en) * | 2003-10-08 | 2008-06-19 | The Yokohama Rubber Co., Ltd. | Method for producing conductive polyaniline |
| CN101139440A (en) * | 2007-10-17 | 2008-03-12 | 天津大学 | Preparation method of high-purity nanosheet polyaniline |
| CN101492569A (en) * | 2008-07-01 | 2009-07-29 | 南京理工大学 | Oxidized graphite flake layer/polyaniline composite material and method for preparing the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106543381B (en) | A kind of hydroxyl polyacrylate aqueous dispersion and preparation method thereof | |
| CN103130943A (en) | Preparation method of water-borne acrylic resin emulsion for wood paint | |
| CN103555115A (en) | Paint for galvanized sheet and preparation method thereof | |
| CN102268214A (en) | Preparation method of aqueous epoxy resin paint | |
| CN104293075B (en) | A kind of modified polyphenyl amine type anticorrosive paint and preparation method thereof | |
| CN102627752B (en) | Preparation method for waterborne epoxy resin emulsion | |
| CN104004204B (en) | A kind of sulfonate type dianion emulsifying agent containing epoxide group and preparation method thereof | |
| CN104927052A (en) | Method for preparing polyaniline solution in organic solvent | |
| CN106432706A (en) | Novel self-emulsifying water-based polyester emulsion and preparation method thereof | |
| CN109880496A (en) | A kind of bumper quick-dry type coating and preparation method thereof | |
| CN107227093B (en) | A kind of epoxy polypyrrole metal anti-corrosive paint and preparation method thereof | |
| CN102977688A (en) | A kind of water-oil universal color paste and preparation method thereof | |
| CN104479136A (en) | Nonionic epoxy emulsifier and preparation method thereof | |
| CN105131305A (en) | Aqueous hyperbranched polymer emulsifier, and applications thereof in preparing water-borne epoxy resin emulsion | |
| CN106800854A (en) | A kind of aqueous double-component plastic paint and preparation method thereof | |
| CN106752205A (en) | A kind of resistance to compression anticorrosion weaving connecting rod and preparation method thereof | |
| CN106117519B (en) | The preparation method of the low peculiar smell Diamond Search aqueous epoxy curing agent of environment-friendly type | |
| CN109206633A (en) | A kind of preparation method of aqueous epoxy emulsion | |
| CN104830196B (en) | One pack system high film build energy water paint and preparation method thereof | |
| CN107652837A (en) | A kind of preparation method of epoxy polyamide coating | |
| CN109280154A (en) | A kind of self-emulsifying aqueous Low-temperature epoxy resin curing agent based on heterocyclic compound | |
| CN104830215B (en) | Application of the alkyd resin esterification waste water in alkyd resin coating preparation | |
| CN104829849B (en) | A kind of alkyd phase inversion emulsion and preparation method and application | |
| CN104910761A (en) | Electromagnetic wave absorbing coating and preparation method thereof | |
| CN103773163A (en) | Alcohol-resistant hydroxyl acrylic resin refinishing paint used for automobile |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150923 |