NO174691B - Anvendelse av 1-hydroksymetylpyrazoler for kontroll av mikroorganisasjoner i vandige systemer - Google Patents
Anvendelse av 1-hydroksymetylpyrazoler for kontroll av mikroorganisasjoner i vandige systemer Download PDFInfo
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- NO174691B NO174691B NO885493A NO885493A NO174691B NO 174691 B NO174691 B NO 174691B NO 885493 A NO885493 A NO 885493A NO 885493 A NO885493 A NO 885493A NO 174691 B NO174691 B NO 174691B
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- Prior art keywords
- aqueous system
- dimethyl
- hydroxymethylpyrazole
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- 244000005700 microbiome Species 0.000 title claims description 8
- BYUMAPPWWKNLNX-UHFFFAOYSA-N pyrazol-1-ylmethanol Chemical class OCN1C=CC=N1 BYUMAPPWWKNLNX-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000003973 paint Substances 0.000 claims description 14
- 239000000839 emulsion Substances 0.000 claims description 12
- OBENDWOJIFFDLZ-UHFFFAOYSA-N (3,5-dimethylpyrazol-1-yl)methanol Chemical compound CC=1C=C(C)N(CO)N=1 OBENDWOJIFFDLZ-UHFFFAOYSA-N 0.000 claims description 7
- 230000015556 catabolic process Effects 0.000 claims description 7
- 238000006731 degradation reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000002906 microbiologic effect Effects 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- DLGMQZRYWBFVKO-UHFFFAOYSA-N (3,5-dimethylpyrazol-1-yl)methanol;hydrochloride Chemical compound Cl.CC=1C=C(C)N(CO)N=1 DLGMQZRYWBFVKO-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 4
- 238000005555 metalworking Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims 3
- 239000000047 product Substances 0.000 description 10
- 230000002335 preservative effect Effects 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- NVICRVZMUABBKZ-UHFFFAOYSA-N (4-chloro-3,5-dimethylpyrazol-1-yl)methanol Chemical compound CC1=NN(CO)C(C)=C1Cl NVICRVZMUABBKZ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012009 microbiological test Methods 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- -1 polishes Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
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Description
Den foreliggende oppfinnelse vedrører anvendelse av en forbindelse med formel
hvori R og R' uavhengig velges fra hydrogen eller en metyl-gruppe, R" er en enhet valgt fra gruppen som består av (a) hydrogen, (b) et halogenatom valgt fra gruppen som består av F, Cl, Br og I, og (c) en nitrogruppe; eller hydrokloridsaltet av nevnte forbindelse, og hvori nevnte forbindelse eller nevnte hydrokloridsalt av nevnte forbindelse tilsettes i en mengde som er tilstrekkelig til å hemme vekst og formering av minst én mikroorganisme i nevnte vandige system til konservering av et vandig system som er utsatt for mikrobiologisk nedbrytning. Typisk omfatter slike systemer vandige oppløsninger, emulsjoner og suspensjoner.
Et stort antall kommersielle og industrielle produkter omfatter vandige systemer som inneholder organiske materialer. Eksempler er lateksprodukter, overflateaktive stoffer, dispergeringsmidler, stabiliseringsmidler, fortykningsmidler, klebemidler, stivelser, voksarter, proteiner, emulgerings-midler, rensemidler, celluloseprodukter og harpikser tilberedt i' vandige oppløsninger, emulsjoner eller suspensjoner. Slike produkter inneholder ofte relativt store mengder vann. Temperaturen hvorved disse produkter lagres, og også deres pH gjør at disse produkter har tendens til vekst av mikroorganismer. Disse mikroorganismer kan føres inn under tillaging av disse produkter (ved eksponering til luft, tanker, rør, utstyr og mennesker), og/eller under bruk av disse (ved gjentatte åpninger og lukninger av pakkede produkter, og innføring av forurensede objekter for å røre eller fjerne materiale).
Mikrobiologisk nedbrytning av vandige systemer som inneholder organisk materiale kan tilkjennegi seg i en rekke forskjellige problemer. Disse omfatter tap av viskositet, gassdannelse, ubehagelige lukter, nedsatt pH, emulsjoner som skjærer seg, fargeforandring og gelering.
Ved den foreliggende oppfinnelse konserveres et vandig system som har tendens til mikrobiologisk nedbrytning ved at det tilsettes en forbindelse som har formel
hvori R og R' uavhengig velges fra hydrogen eller en metyl-gruppe, R" er en enhet som velges fra gruppen som består av (a) hydrogen, (b) et halogenatom valgt fra gruppen som består av F, Cl, Br og I, og (c) en nitrogruppe; eller hydrokloridsaltet av nevnte forbindelse, idet forbindelsen eller hydrokloridsaltet av forbindelsen tilsettes i en mengde tilstrekkelig til å hemme veksten og spredningen av minst én mikroorganisme i det vandige systemet.
Oppfinnelsen kan benyttes for å forhindre mikrobiologisk nedbrytning i alle vandige systemer som har tendens til slik nedbrytning, såsom vandige oppløsninger, emulsjoner og suspensj oner.
Eksempler på vandige oppløsninger, emulsjoner og suspensjoner som utsettes for mikrobiolgoisk nedbrytning omfatter vannbaserte malinger, lateksemulsjoner, såsom akryl- og polyvinylacetatemulsjoner, klebeoppløsninger og emulsjoner, voksemulsjoner, polermidler, flytende oppløsninger og emulsjoner til metallbearbeiding, tetnings- og forseglingspro-dukter, kjemiske produkter til papirfabrikasjon såsom alu-miniumsulfatoppløsninger, leire og pigmentdispersjoner, stivelsesoppslemminger og oppløsninger og proteinovertrekks-preparater og kosmetiske preparater.
Den konserverende virkning av forbindelsene som anvendes ifølge oppfinnelsen er overraskende ettersom N-metyloiforbin-delser med tilsvarende stabilitet, f.eks. N-hydroksymetyl-ftalimid, ikke er særlig effektive når det gjelder deres antimikrobielle og konserverende virkning.
Forbindelsene kan fremstilles ved å omsette enten fast paraformaldehyd eller en vandig formaldehydoppløsning med et pyrazolderivat. Foretrukne fremgangsmåter for fremstilling er gitt i Dvoretzky et al., Formaldehvde Condensation in the Pvrazole Series. 15 Journ. Org. Chem. 1285-8 (1952) og Huttel et al., Mannichsche Reaktion der Pvrazole, 85 Chemische Berichte 820-26 (1952).
Den antimikrobielle~virkning av forbindelsene anvendt i henhold til oppfinnelsen gjelder en rekke forskjellige mikroorgansimer, inkludert bakterier såsom Escherichia coli, Staphylococcus aureus, Pseudomonas aeru<g>inosa, Enterobacter aero<g>enes og Bacillus subtilis. og sopper såsom Candida albicans og Aspergillus niger.
Konsentrasjonen av forbindelsene i denne oppfinnelsen som hemmer vekst og formering av en mikroorganisme og således gir den konserverende virkning beskrevet her, kan lett bestemmes av en som har fagkunnskap uten omfattende eksperimentering og, vil fortrinnsvis variere fra rundt 0,1 deler til rundt 1000 deler av forbindelsen i en million deler av det vandige system som skal konserveres.
For å illustrere oppfinnelsens natur, gis de følgende eksempler. Det må imidlertid være klart at oppfinnelsen ikke begrenses til de spesifikke forhold eller detaljer angitt i disse eksempler.
EKSEMPEL 1
Den konserverende virkning av disse forbindelser ble bestemt i en nyfremstilt vannbasert maling tilberedt med titandioksyd og kalsiumkarbonat som pigmenter, en akryl-harpiksemulsjon, dispergeringsmidler og hydroksyetylcellulose som fortykningsmiddel. pH i denne malingen var omtrent 9,0. Testen ble gjennomført på følgende måte: 3,5-dimetyl-l-hydroksymetylpyrazol ble tilsatt til den ferdige akryl1ateksmaling i nivåer som varierte fra 75 til 1500 deler pr. million deler av malingen. 100 g av test-malingen ble inokulert ukentlig i en ti ukers utfordringstest med 1,0 milliliter maling som inneholdt Pseudomonas aeruginosa i et nivå på omtrent 1,5 x 10<6> organismer pr. milliliter. Etter kraftig rysting, ble den inokulerte maling inkubert ved 28°C. Testmalingene ble streket på næringsagarplater 24, 48, 168 timer etter inokulering. De strekede plater ble inkubert ved 37°C og undersøkt med hensyn på bakterievekst etter 48 tiemr. Tabell I representerer de endelige data akkumulert fra en 10 ukers utfordringstest med malinger som inneholdt 75 til 1500 deler 3,5-dimetyl-l-hydroksymetylpyrazol pr. million deler maling.
EKSEMPEL 2
Den antimikrobielle virkning av 1-hydroksymetylpyrazol, 3 , 5-dimetyl-l-hydroksymetylpyrazol, 3,5-dimetyl-l-hydroksy-metylpyrazolhydroklorid og 4-klor-3,5-dimetyl-l-hydroksymetylpyrazol ble bestemt ved fremgangsmåten for konservering av en organisk substans beskrevet i United States Pharmacopeia, 21. reviderte utgave (1. januar 1985), "Microbiological Test #51" s. 1151. Testresultatene er gitt i tabell II.
Claims (13)
1. Anvendelse av en forbindelse med formel
hvori R og R' uavhengig velges fra hydrogen eller en metyl-gruppe, R" er en enhet valgt fra gruppen som består av (a) hydrogen, (b) et halogenatom valgt fra gruppen som består av F, Cl, Br og I, og (c) en nitrogruppe; eller hydrokloridsaltet av nevnte forbindelse, og hvori nevnte forbindelse eller nevnte hydrokloridsalt av nevnte forbindelse tilsettes i en mengde som er tilstrekkelig til å hemme vekst og formering av minst én mikroorganisme i nevnte vandige system til konservering av et vandig system som er utsatt for mikrobiologisk nedbrytning.
2. Anvendelse i henhold til krav 1, hvori nevnte vandige system tilhører gruppen vandige oppløsninger, emulsjoner og suspensjoner.
3. Anvendelse av 3,5-dimetyl-l-hydroksymetylpyrazol i henhold til krav 1.
4. Anvendelse av 3,5-dimetyl-l-hydroksymetylpyrazol-hydroklorid i henhold til krav 1.
5. Anvendelse i henhold til krav 1, hvori nevnte vandige system er en vannbasert maling.
6. Anvendelse i henhold til krav 1, hvori nevnte vandige system er en vannbasert maling og nevnte forbindelse er 3,5-dimetyl-l-hydroksymetylpyrazol.
7. Anvendelse av 3,5-dimetyl-l hydroksymetylpyrazol-hydroklorid i henhold til krav 1, hvori nevnte vandige system er en vannbasert maling.
8. Anvendelse i henhold til krav 1, hvori nevnte vandige system er et kosmetisk preparat.
9. Anvendelse av 3,5-dimetyl-l-hydroksymetylpyrazol i henhold til krav 1, hvori nevnte vandige system er et kosmetisk preparat.
10. Anvendelse av 3,5-dimetyl-l-hydroksymetyl-pyrazolhydroklorid i henhold til krav 1, hvori nevnte vandige system er et kosmetisk preparat.
11. Anvendelse i henhold til krav 1, hvori nevnte vandige system er en væske til metallbearbeiding.
12. Anvendelse av 3,5-dimetyl-l-hydroksymetylpyrazol
i henhold til krav 1, hvori nevnte vandige system er en væske til metallbearbeiding.
13. Anvendelse av 3,5-dimetyl-l-hydroksymetylpyrazol-hydroklorid i henhold til krav 1, hvori nevnte vandige system er en væske til metallbearbeiding.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/131,733 US4801362A (en) | 1987-12-11 | 1987-12-11 | Control of microorganisms in aqueous systems with 1-hydroxymethylpyrazoles |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO885493D0 NO885493D0 (no) | 1988-12-09 |
| NO885493L NO885493L (no) | 1989-06-12 |
| NO174691B true NO174691B (no) | 1994-03-14 |
| NO174691C NO174691C (no) | 1994-06-22 |
Family
ID=22450774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO885493A NO174691C (no) | 1987-12-11 | 1988-12-09 | Anvendelse av 1-hydroksymetylpyrazoler for kontroll av mikroorganisasjoner i vandige systemer |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4801362A (no) |
| EP (1) | EP0320309B1 (no) |
| JP (1) | JP2577786B2 (no) |
| AR (1) | AR247815A1 (no) |
| AT (1) | ATE109185T1 (no) |
| AU (1) | AU605367B2 (no) |
| CA (1) | CA1329851C (no) |
| DE (1) | DE3850862T2 (no) |
| ES (1) | ES2060663T3 (no) |
| FI (1) | FI92641C (no) |
| MX (1) | MX165561B (no) |
| NO (1) | NO174691C (no) |
| NZ (1) | NZ225589A (no) |
| ZA (1) | ZA885730B (no) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02242890A (ja) * | 1989-03-16 | 1990-09-27 | Yushiro Chem Ind Co Ltd | 抗菌性水溶性切削油剤 |
| US5028458A (en) * | 1990-01-16 | 1991-07-02 | Warren F. B. Lindsley | Antiseptic polish |
| NZ238917A (en) * | 1990-07-20 | 1994-04-27 | Buckman Labor Inc | Microbicidal compositions containing a 1-hydroxymethylpyrazole derivative |
| NZ238916A (en) * | 1990-07-20 | 1993-09-27 | Buckman Labor Inc | Preparation of 1-hydroxymethylpyrazoles |
| DE4309690A1 (de) * | 1993-03-25 | 1994-09-29 | Bayer Ag | Anstrichmittel |
| US5661149A (en) * | 1995-12-29 | 1997-08-26 | Buckman Laboratories International, Inc. | Synergistic antimicrobial compositions containing 1-hydroxymethylpyrazole and a preservative |
| JP4851930B2 (ja) * | 2006-12-27 | 2012-01-11 | 松山株式会社 | 農作業機用制御装置 |
| DE102019005628B9 (de) | 2019-08-09 | 2021-11-18 | GbR Dr. Holger Brill, Dr. Herbert Widulle, Peter Waitszies (vertretungsberechtigter Gesellschafter Dr. Herbert Widulle, Buntspechtweg 7a, 22547 Hamburg) | Verfahren zur Reinigung von sulfidhaltigen Rohstoffen und gleichzeitigen Gewinnung von elementarem Schwefel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD222471A3 (de) * | 1982-09-06 | 1985-05-15 | Piesteritz Stickstoff | Wirkstoffkombination zur hemmung bzw. regelung der nitrifikation von ammoniumstickstoff in kulturboeden |
-
1987
- 1987-12-11 US US07/131,733 patent/US4801362A/en not_active Expired - Lifetime
-
1988
- 1988-07-27 NZ NZ225589A patent/NZ225589A/en unknown
- 1988-08-04 ZA ZA885730A patent/ZA885730B/xx unknown
- 1988-08-09 AR AR88311620A patent/AR247815A1/es active
- 1988-08-24 CA CA000575619A patent/CA1329851C/en not_active Expired - Fee Related
- 1988-09-26 JP JP63240640A patent/JP2577786B2/ja not_active Expired - Fee Related
- 1988-10-14 AU AU23745/88A patent/AU605367B2/en not_active Ceased
- 1988-11-01 FI FI885017A patent/FI92641C/fi not_active IP Right Cessation
- 1988-11-10 MX MX013739A patent/MX165561B/es unknown
- 1988-12-09 NO NO885493A patent/NO174691C/no not_active IP Right Cessation
- 1988-12-12 ES ES88311749T patent/ES2060663T3/es not_active Expired - Lifetime
- 1988-12-12 DE DE3850862T patent/DE3850862T2/de not_active Expired - Fee Related
- 1988-12-12 EP EP88311749A patent/EP0320309B1/en not_active Expired - Lifetime
- 1988-12-12 AT AT88311749T patent/ATE109185T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO174691C (no) | 1994-06-22 |
| FI92641B (fi) | 1994-09-15 |
| MX165561B (es) | 1992-11-23 |
| AU605367B2 (en) | 1991-01-10 |
| CA1329851C (en) | 1994-05-24 |
| JP2577786B2 (ja) | 1997-02-05 |
| FI92641C (fi) | 1994-12-27 |
| EP0320309A3 (en) | 1991-07-03 |
| ZA885730B (en) | 1989-05-30 |
| DE3850862D1 (de) | 1994-09-01 |
| DE3850862T2 (de) | 1995-03-02 |
| FI885017A0 (fi) | 1988-11-01 |
| FI885017A (fi) | 1989-06-12 |
| ES2060663T3 (es) | 1994-12-01 |
| US4801362A (en) | 1989-01-31 |
| AU2374588A (en) | 1989-06-15 |
| NO885493L (no) | 1989-06-12 |
| EP0320309B1 (en) | 1994-07-27 |
| NO885493D0 (no) | 1988-12-09 |
| NZ225589A (en) | 1990-04-26 |
| ATE109185T1 (de) | 1994-08-15 |
| EP0320309A2 (en) | 1989-06-14 |
| AR247815A1 (es) | 1995-04-28 |
| JPH01172305A (ja) | 1989-07-07 |
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