CA1057894A - Fabrication de la polyvinylpyrrolidone - Google Patents

Fabrication de la polyvinylpyrrolidone

Info

Publication number: CA1057894A
Authority: CA; Canada
Prior art keywords: polymerization; polyvinylpyrrolidone; vinylpyrrolidone; tert; parts
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

CA233,155A

Other languages

English (en)

Other versions

CA233155S (en

Inventor

Karl Herrle

Walter Denzinger

Kurt Seelert

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

1975-08-08

Publication date

1979-07-03

1975-08-08 Application filed by BASF SE filed Critical BASF SE

1979-07-03 Application granted granted Critical

1979-07-03 Publication of CA1057894A publication Critical patent/CA1057894A/fr

Status Expired legal-status Critical Current

Links

235000013855 polyvinylpyrrolidone Nutrition 0.000 title claims abstract description 41
239000001267 polyvinylpyrrolidone Substances 0.000 title claims abstract description 28
238000004519 manufacturing process Methods 0.000 title claims abstract description 16
229920000036 polyvinylpyrrolidone Polymers 0.000 title abstract description 38
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 35
238000006116 polymerization reaction Methods 0.000 claims abstract description 26
239000012190 activator Substances 0.000 claims abstract description 11
229910001385 heavy metal Inorganic materials 0.000 claims abstract description 10
239000003960 organic solvent Substances 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 5
150000007524 organic acids Chemical class 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
238000000034 method Methods 0.000 claims description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
150000004996 alkyl benzenes Chemical class 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000002736 metal compounds Chemical class 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
239000005749 Copper compound Substances 0.000 claims 1
150000001880 copper compounds Chemical class 0.000 claims 1
239000011630 iodine Substances 0.000 abstract description 20
229910052740 iodine Inorganic materials 0.000 abstract description 20
239000002537 cosmetic Substances 0.000 abstract description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 15
239000000243 solution Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 13
239000007864 aqueous solution Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
-1 alkyl hydroperoxides Chemical class 0.000 description 10
229960004592 isopropanol Drugs 0.000 description 10
229920000642 polymer Polymers 0.000 description 10
239000002904 solvent Substances 0.000 description 9
238000002474 experimental method Methods 0.000 description 8
238000009835 boiling Methods 0.000 description 5
239000000872 buffer Substances 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000000178 monomer Substances 0.000 description 5
150000002978 peroxides Chemical class 0.000 description 5
230000001954 sterilising effect Effects 0.000 description 5
238000004659 sterilization and disinfection Methods 0.000 description 5
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 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
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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 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
238000007796 conventional method Methods 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
239000011521 glass Substances 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
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 2
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
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 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
230000003081 coactivator Effects 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
BNGNANCNFVQZBM-UHFFFAOYSA-N cobalt;ethyl hexanoate Chemical compound [Co].CCCCCC(=O)OCC BNGNANCNFVQZBM-UHFFFAOYSA-N 0.000 description 2
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 2
238000000354 decomposition reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-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
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
235000005985 organic acids Nutrition 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
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
238000010526 radical polymerization reaction Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
238000001694 spray drying Methods 0.000 description 2
238000001256 steam distillation Methods 0.000 description 2
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 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
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
JBPBJJJEAHNMLH-UHFFFAOYSA-N CCC(C)O.OO Chemical compound CCC(C)O.OO JBPBJJJEAHNMLH-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
239000008351 acetate buffer Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001412 amines 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
159000000032 aromatic acids Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
239000001273 butane Substances 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000013522 chelant Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000012933 diacyl peroxide Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000001599 direct drying Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000002036 drum drying Methods 0.000 description 1
VKOBVWXKNCXXDE-UHFFFAOYSA-N ethyl stearic acid Natural products CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052742 iron Inorganic materials 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
229940071125 manganese acetate Drugs 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
244000005700 microbiome Species 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
229910052757 nitrogen Inorganic materials 0.000 description 1
WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical class CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 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
239000003279 phenylacetic acid Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
229920006316 polyvinylpyrrolidine Polymers 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
239000002510 pyrogen Substances 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
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
238000005245 sintering Methods 0.000 description 1
239000008149 soap solution Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 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
239000003039 volatile agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F126/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F126/06—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F126/10—N-Vinyl-pyrrolidone

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Polymerization Catalysts (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polymerisation Methods In General (AREA)
Medicinal Preparation (AREA)
Cosmetics (AREA)

CA233,155A 1974-08-16 1975-08-08 Fabrication de la polyvinylpyrrolidone Expired CA1057894A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742439196 DE2439196C3 (de)	1974-08-16	1974-08-16	Verfahren zur Herstellung von Polyvinylpyrrolidon

Publications (1)

Publication Number	Publication Date
CA1057894A true CA1057894A (fr)	1979-07-03

Family

ID=5923266

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA233,155A Expired CA1057894A (fr)	1974-08-16	1975-08-08	Fabrication de la polyvinylpyrrolidone

Country Status (10)

Country	Link
JP (1)	JPS5146388A (fr)
BE (1)	BE832352A (fr)
CA (1)	CA1057894A (fr)
CH (1)	CH617214A5 (fr)
DE (1)	DE2439196C3 (fr)
ES (1)	ES440275A1 (fr)
FR (1)	FR2281942A1 (fr)
GB (1)	GB1513258A (fr)
NL (1)	NL7508762A (fr)
SE (1)	SE406914B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3642633A1 (de) *	1986-12-13	1988-06-23	Basf Ag	Verfahren zur herstellung von vinylpyrrolidon-polymerisaten
DE19915420A1 (de) *	1999-04-06	2000-10-12	Basf Ag	Stabilisierte Polyvinylpyrrolidon-Zubereitungen
CN102603949B (zh) *	2011-12-22	2014-03-19	张家口市珂玛精细化工有限公司	利用低纯度乙烯基吡咯烷酮制备聚维酮k30的方法

1974
- 1974-08-16 DE DE19742439196 patent/DE2439196C3/de not_active Expired
1975
- 1975-07-22 NL NL7508762A patent/NL7508762A/xx not_active Application Discontinuation
- 1975-08-08 CA CA233,155A patent/CA1057894A/fr not_active Expired
- 1975-08-12 BE BE159133A patent/BE832352A/fr not_active IP Right Cessation
- 1975-08-13 FR FR7525189A patent/FR2281942A1/fr active Granted
- 1975-08-13 CH CH1055675A patent/CH617214A5/de not_active IP Right Cessation
- 1975-08-14 ES ES440275A patent/ES440275A1/es not_active Expired
- 1975-08-14 SE SE7509114A patent/SE406914B/xx not_active IP Right Cessation
- 1975-08-15 JP JP9865075A patent/JPS5146388A/ja active Pending
- 1975-08-15 GB GB3402075A patent/GB1513258A/en not_active Expired

Also Published As

Publication number	Publication date
FR2281942B1 (fr)	1980-04-04
DE2439196A1 (de)	1976-02-26
SE7509114L (sv)	1976-02-17
CH617214A5 (en)	1980-05-14
NL7508762A (nl)	1976-02-18
GB1513258A (en)	1978-06-07
DE2439196B2 (de)	1978-03-09
SE406914B (sv)	1979-03-05
FR2281942A1 (fr)	1976-03-12
JPS5146388A (ja)	1976-04-20
ES440275A1 (es)	1977-06-01
BE832352A (fr)	1976-02-12
DE2439196C3 (de)	1978-11-02

Publication	Publication Date	Title
US4320114A (en)	1982-03-16	Manufacture of aqueous polyvinylpyrrolidone-iodine solutions
US4027083A (en)	1977-05-31	Manufacture of polyvinylpyrrolidone-iodine
US4053696A (en)	1977-10-11	Manufacture of vinylpyrrolidone polymers
US3759880A (en)	1973-09-18	Pyrrolidone-2 manufacture of insoluble and only slightly swellable poly - n - vinyl
CA2363730A1 (fr)	2001-12-20	Procede de preparation de polymere de vinylpirrolidone
JPS5850604B2 (ja)	1983-11-11	低分子ポリ−ｎ−ビニルピロリドン−２の製法
EP0299025B1 (fr)	1993-05-19	Resines ameliorees pour traitement capillaire
KR20240167823A (ko)	2024-11-28	살생물제-무함유 유기 불투명화 안료 입자의 수성 분산액
RU2190626C2 (ru)	2002-10-10	Агенты подавления образования нароста, способ их получения, композиция, содержащая агенты, способ подавления образования нароста, способ полимеризации, реактор полимеризации
TW200405898A (en)	2004-04-16	Preparation of expandable styrene polymers
JP5577637B2 (ja)	2014-08-27	アミンオキシド基含有樹脂溶液、及びそれを用いた毛髪化粧料用樹脂組成物
Baranovsky et al.	1992	Template polymerization of methacrylic acid in the presence of poly (ethylene glycol) and poly (N-vinylpyrrolidone) in benzene
US3129210A (en)	1964-04-14	Process for polymerizing n-vinyl lactams
US6465592B1 (en)	2002-10-15	Process for preparing vinylpyrrolidone polymer
CN103044596A (zh)	2013-04-17	一种聚乙烯吡咯烷酮的聚合方法
DE2439196C3 (de)	1978-11-02	Verfahren zur Herstellung von Polyvinylpyrrolidon
US5663253A (en)	1997-09-02	Policarboxylic acids
CN119816203A (zh)	2025-04-11	抗微生物苯乙烯胶乳组合物
DE2523618C3 (de)	1980-03-27	Verfahren zur Herstellung von Polyvinylpyrrolidon-Jod
EP1198483B1 (fr)	2004-07-28	Procede pour la fabrication de fines poudres blanches exemptes de solvant de copolymeres a poids moleculaire elevee d'anhydride maleique et d'ether vinylique d'alkyle c1-c4 inodore et insipide
US4977240A (en)	1990-12-11	Unsaturated alkyd-containing organic peroxide composition
FR2468628A1 (fr)	1981-05-08	Composition pour la preparation de polymeres d'acrylamide et d'acides acryliques ameliores contenant une 1,3 dione et procede de preparation de ces polymeres
EP1198486B1 (fr)	2005-10-05	Fines poudres blanches exemptes de solvant d'un anhydre maleique et d'un ether vinylique d'alkyle c1-c4 sensiblement exempt de poly(ether vinylique d'alkyle) homopolymere
Imai et al.	1978	Polymerization of monoallyl phthalate
JPH04226113A (ja)	1992-08-14	マレイン酸のモノアルキルエステル又はマレイン酸及びその塩とビニルアルキルエーテルとの共重合体の製造法