CA1081394A - Production industrielle de polyvinylepyrrolidone-iode - Google Patents

Production industrielle de polyvinylepyrrolidone-iode

Info

Publication number: CA1081394A
Authority: CA; Canada
Prior art keywords: iodine; pvp; polyvinylpyrrolidone; parts; vinylpyrrolidone
Prior art date: 1974-08-16
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.): Expired

Application number

CA334,554A

Other languages

English (en)

Inventor

Karl Herrle

Kurt Seelert

Walter Denzinger

Wolfgang Schwarz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1974-08-16

Filing date

1979-08-28

Publication date

1980-07-08

1974-08-16 Priority claimed from DE19742439197 external-priority patent/DE2439197B2/de

1975-05-28 Priority claimed from DE19752523618 external-priority patent/DE2523618C3/de

1975-08-08 Priority claimed from CA233,153A external-priority patent/CA1079443A/fr

1979-08-28 Application filed by BASF SE filed Critical BASF SE

1979-08-28 Priority to CA334,554A priority Critical patent/CA1081394A/fr

1980-07-08 Application granted granted Critical

1980-07-08 Publication of CA1081394A publication Critical patent/CA1081394A/fr

Status Expired legal-status Critical Current

Links

239000011630 iodine Substances 0.000 title claims abstract description 68
229910052740 iodine Inorganic materials 0.000 title claims abstract description 68
238000004519 manufacturing process Methods 0.000 title claims abstract description 19
239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 64
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 64
229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 62
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
239000000243 solution Substances 0.000 claims abstract description 33
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 31
238000006116 polymerization reaction Methods 0.000 claims abstract description 30
239000007864 aqueous solution Substances 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 17
230000008569 process Effects 0.000 claims abstract description 14
239000003960 organic solvent Substances 0.000 claims abstract description 13
150000003254 radicals Chemical class 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
150000001298 alcohols Chemical class 0.000 claims abstract description 5
125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 5
238000011282 treatment Methods 0.000 claims abstract description 5
238000001035 drying Methods 0.000 claims abstract description 4
238000010526 radical polymerization reaction Methods 0.000 claims abstract description 4
239000012190 activator Substances 0.000 claims description 8
-1 organic acid salt Chemical class 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
239000000203 mixture Substances 0.000 description 37
CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 29
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
239000007787 solid Substances 0.000 description 16
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 14
229960004592 isopropanol Drugs 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000000843 powder Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
238000009835 boiling Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
238000001694 spray drying Methods 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 5
229910001385 heavy metal Inorganic materials 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
239000007921 spray Substances 0.000 description 5
238000003860 storage Methods 0.000 description 5
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
239000011521 glass Substances 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
239000000178 monomer Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 3
ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000012265 solid product Substances 0.000 description 3
238000001256 steam distillation Methods 0.000 description 3
238000004448 titration Methods 0.000 description 3
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
229910001516 alkali metal iodide Inorganic materials 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
239000000645 desinfectant Substances 0.000 description 2
239000012969 di-tertiary-butyl peroxide Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001599 direct drying Methods 0.000 description 2
238000002036 drum drying Methods 0.000 description 2
238000011010 flushing procedure Methods 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000002453 shampoo Substances 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
229910000406 trisodium phosphate Inorganic materials 0.000 description 2
235000019801 trisodium phosphate Nutrition 0.000 description 2
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
IEOJTQSWHLGOQI-UHFFFAOYSA-L 2-aminoacetate;nickel(2+) Chemical compound [Ni+2].NCC([O-])=O.NCC([O-])=O IEOJTQSWHLGOQI-UHFFFAOYSA-L 0.000 description 1
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
JXSRRBVHLUJJFC-UHFFFAOYSA-N 7-amino-2-methylsulfanyl-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound N1=CC(C#N)=C(N)N2N=C(SC)N=C21 JXSRRBVHLUJJFC-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000013011 aqueous formulation Substances 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000000337 buffer salt Substances 0.000 description 1
239000001273 butane Substances 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
239000013522 chelant Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
230000003081 coactivator Effects 0.000 description 1
BNGNANCNFVQZBM-UHFFFAOYSA-N cobalt;ethyl hexanoate Chemical compound [Co].CCCCCC(=O)OCC BNGNANCNFVQZBM-UHFFFAOYSA-N 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000012933 diacyl peroxide Substances 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
VKOBVWXKNCXXDE-UHFFFAOYSA-N ethyl stearic acid Natural products CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
229940058172 ethylbenzene Drugs 0.000 description 1
238000005187 foaming Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000002070 germicidal effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
GTNLRWSWRMVLFI-UHFFFAOYSA-N n-[[2-[2-[2-(hydroxyiminomethyl)phenoxy]ethoxy]phenyl]methylidene]hydroxylamine Chemical compound ON=CC1=CC=CC=C1OCCOC1=CC=CC=C1C=NO GTNLRWSWRMVLFI-UHFFFAOYSA-N 0.000 description 1
125000005608 naphthenic acid group Chemical group 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
150000002976 peresters Chemical class 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000008149 soap solution Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA334,554A 1974-08-16 1979-08-28 Production industrielle de polyvinylepyrrolidone-iode Expired CA1081394A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA334,554A CA1081394A (fr)	1974-08-16	1979-08-28	Production industrielle de polyvinylepyrrolidone-iode

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19742439197 DE2439197B2 (de)	1974-08-16	1974-08-16	Verwendung von in organischer loesung hergestelltem polyvinylpyrrolidon zur herstellung von polyvinylpyrrolidon- jod
DE19752523618 DE2523618C3 (de)	1975-05-28	1975-05-28	Verfahren zur Herstellung von Polyvinylpyrrolidon-Jod
CA233,153A CA1079443A (fr)	1974-08-16	1975-08-08	Preparation industrielle de l'iodure de polyvinylpyrrolidone
CA334,554A CA1081394A (fr)	1974-08-16	1979-08-28	Production industrielle de polyvinylepyrrolidone-iode

Publications (1)

Publication Number	Publication Date
CA1081394A true CA1081394A (fr)	1980-07-08

Family

ID=27425860

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA334,554A Expired CA1081394A (fr)	1974-08-16	1979-08-28	Production industrielle de polyvinylepyrrolidone-iode

Country Status (1)

Country	Link
CA (1)	CA1081394A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113855628A (zh) *	2021-11-02	2021-12-31	广东托尔沃登卫生用品有限公司	一种聚维酮碘消毒液的生产工艺及其产品

1979
- 1979-08-28 CA CA334,554A patent/CA1081394A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113855628A (zh) *	2021-11-02	2021-12-31	广东托尔沃登卫生用品有限公司	一种聚维酮碘消毒液的生产工艺及其产品
CN113855628B (zh) *	2021-11-02	2023-03-14	广东托尔沃登卫生用品有限公司	一种聚维酮碘消毒液的生产工艺及其产品

Legal Events

Date	Code	Title	Description
1997-07-08	MKEX	Expiry

Publication	Publication Date	Title
US4027083A (en)	1977-05-31	Manufacture of polyvinylpyrrolidone-iodine
US4320114A (en)	1982-03-16	Manufacture of aqueous polyvinylpyrrolidone-iodine solutions
US5108742A (en)	1992-04-28	Anhydrous complexes of PVP and H2 O2
US5008093A (en)	1991-04-16	Anhydrous complexes of PVP and hydrogen peroxide
US3480557A (en)	1969-11-25	Solid stabilized hydrogen peroxide compositions
US4113857A (en)	1978-09-12	Process for the preparation of iodophor compounds and methods for stabilizing iodophor pharmaceutical compositions containing the same
US3136755A (en)	1964-06-09	Insoluble polymeric-iodine complexes
CA2363730A1 (fr)	2001-12-20	Procede de preparation de polymere de vinylpirrolidone
WO1989000006A1 (fr)	1989-01-12	Composition germicide
CA1158798A (fr)	1983-12-13	Preparation de pvp-iode
CA1081394A (fr)	1980-07-08	Production industrielle de polyvinylepyrrolidone-iode
US4200710A (en)	1980-04-29	Preparation of polyvinylpyrrolidone-iodine
US5190749A (en)	1993-03-02	Copolymers of vinyl pyrrolidone and a quaternary ammonium monomer complexed with H2 O2 in the form of free-flowing powders
US3029183A (en)	1962-04-10	Germicidal iodine compositions
CA1155854A (fr)	1983-10-25	Preparation de polyvinylpyrrolidone-iode
CA1057894A (fr)	1979-07-03	Fabrication de la polyvinylpyrrolidone
US5066488A (en)	1991-11-19	Semi-anhydrous, suspension process for preparing uniform, free-flowing, fine, white powders of substantially anhydrous complexes of PVP and H2 O2 containing about 18 to about 22% H2 O2
US4830851A (en)	1989-05-16	Polymeric halophors
EP0201192A2 (fr)	1986-11-12	Polymères contenant des groupes isonitriles et leur procédé de préparation
US20020173608A1 (en)	2002-11-21	Process for preparing vinylpyrrolidone polymer
JP2003509347A (ja)	2003-03-11	ポリビニルピロリドン−ヨードを含む水溶液を製造する方法
US4064166A (en)	1977-12-20	Etherification of bark extracts
DE2523618B2 (fr)	1979-07-26
US4182806A (en)	1980-01-08	Process for the manufacture of salts of poly-alpha-hydroxyacrylic acids
DE2439197B2 (de)	1977-06-16	Verwendung von in organischer loesung hergestelltem polyvinylpyrrolidon zur herstellung von polyvinylpyrrolidon- jod