NO162961B - PROCEDURE FOR RELEASING GLUTARALDEHYDE FROM A MAJOR EQUAL WEIGHT MIXTURE. - Google Patents
PROCEDURE FOR RELEASING GLUTARALDEHYDE FROM A MAJOR EQUAL WEIGHT MIXTURE. Download PDFInfo
- Publication number
- NO162961B NO162961B NO864341A NO864341A NO162961B NO 162961 B NO162961 B NO 162961B NO 864341 A NO864341 A NO 864341A NO 864341 A NO864341 A NO 864341A NO 162961 B NO162961 B NO 162961B
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- Norway
- Prior art keywords
- glutaraldehyde
- mixture
- freezing point
- releasing
- carbon atoms
- Prior art date
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- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 9
- 230000008014 freezing Effects 0.000 claims abstract description 24
- 238000007710 freezing Methods 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229920005862 polyol Polymers 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- -1 aliphatic polyol Chemical class 0.000 claims abstract description 9
- 230000003197 catalytic effect Effects 0.000 claims abstract description 6
- 150000003077 polyols Chemical class 0.000 claims abstract description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 5
- 150000001298 alcohols Chemical class 0.000 claims abstract description 5
- 238000007865 diluting Methods 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000243 solution Substances 0.000 description 19
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 235000001916 dieting Nutrition 0.000 description 1
- 230000037228 dieting effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
En fremgangsmåte for frisetting av glutaraldehyd fra en vandig likevektsblanding med stabilt, redusert frysepunkt, omfattende glutaraldehyd og en alifatisk alkohol med 1-4 karbonatomer eller en alifatisk polyol med 2-6 karbonatomer eller en blanding av de nevnte alkoholer og polyoler, omfatter først å fortynne blandingen med vann og derefter å tilsette en katalytisk mengde av en sterk syre.A process for releasing glutaraldehyde from an aqueous equilibrium mixture with a stable, reduced freezing point, comprising glutaraldehyde and an aliphatic alcohol having 1-4 carbon atoms or an aliphatic polyol having 2-6 carbon atoms or a mixture of said alcohols and polyols, first comprises diluting the mixture with water and then adding a catalytic amount of a strong acid.
Description
Foreliggende oppfinnelse angår en fremgangsmåte for frisetting av glutaraldehyd fra en vandig likevektsblanding med stabilt, redusert frysepunkt, omfattende glutaraldehyd og en alifatisk alkohol med 1-4 karbonatomer eller en alifatisk polyol med 2-6 karbonatomer eller en blanding av de nevnte alkoholer og polyoler. The present invention relates to a method for releasing glutaraldehyde from an aqueous equilibrium mixture with a stable, reduced freezing point, comprising glutaraldehyde and an aliphatic alcohol with 1-4 carbon atoms or an aliphatic polyol with 2-6 carbon atoms or a mixture of the aforementioned alcohols and polyols.
Vandige oppløsninger av glutaraldehyd er velkjente kommer-sielt tilgjengelige materialer som kan brukes for å drepe eller å inhibere veksten av mikroorganismer. Disse vandige oppløsninger av glutaraldehyd er benyttet for å regulere veksten av bakterier i et antall forskjellige omgivelser. For eksempel er glutaraldehydoppløsninger benyttet for å desinfisere medisinske og kirurgiske materialer og hushold-ningsgjenstander. Videre er, som beskrevet i US-PS 2 801 216, glutaraldehydoppløsninger benyttet for å kontrollere bakterievekst ved vanngjennomflømmingsarbeider i forbindelse med sekundergjenvinning av olje, og benyttet for å forhindre korrosjon og tilstopping av jernutstyr på grunn av påvirkning av bakterier i lagringsbeholdere og tilhørende rørledninger og utstyr. Således er det klart at det foreligger tilfeller der glutaraldehydoppløsninger lagres utendørs og kan utsettes for frost. Frysepunktet for en 25#-ig vandig oppløsning av glutaraldehyd er ca. -5,5'C. Derfor ville det under disse betingelser være ønskelig ytterligere å redusere frysepunktet for de vandige glutaraldehydoppløsninger. Imidlertid må additiver som benyttes i forbindelse med vandige glutar-aldehydoppløsninger og som kan redusere frysepunktet for oppløsningen, ikke redusere den kjemiske eller biologiske virkning for oppløsningen på brukstidspunktet og må også være en som bibeholder frysepunktet på den ønskede temperatur. Dette vil si at additivet må være et som er istand til å opprettholde den ønskede temperatur over utstrakte tidsrom. For eksempel er både alkoholer og glykoler som metanol og etylenglykol kjent å reagere med glutaraldehyd slik at, selv om tilsetning av metanol og etylenglykol til en vandig oppløsning av glutaraldehydet til å begynne med reduserer frysepunktet, ved lagring vil føre til en frysepunktstigning etter hvert som alkohol og glykol reagerer med glutaraldehyd og danner en blanding inneholdende acetalbindinger. Derfor er det ønskelig å ha et stabilt fiksert frysepunkt. Aqueous solutions of glutaraldehyde are well known commercially available materials that can be used to kill or inhibit the growth of microorganisms. These aqueous solutions of glutaraldehyde have been used to regulate the growth of bacteria in a number of different environments. For example, glutaraldehyde solutions are used to disinfect medical and surgical materials and household items. Furthermore, as described in US-PS 2,801,216, glutaraldehyde solutions are used to control bacterial growth during water flooding operations in connection with the secondary recovery of oil, and are used to prevent corrosion and clogging of iron equipment due to the influence of bacteria in storage containers and associated pipelines and equipment. Thus, it is clear that there are cases where glutaraldehyde solutions are stored outdoors and can be exposed to frost. The freezing point of a 25# aqueous solution of glutaraldehyde is approx. -5.5'C. Therefore, under these conditions, it would be desirable to further reduce the freezing point of the aqueous glutaraldehyde solutions. However, additives used in connection with aqueous glutaraldehyde solutions and which can reduce the freezing point of the solution must not reduce the chemical or biological effect of the solution at the time of use and must also be one that maintains the freezing point at the desired temperature. This means that the additive must be one that is able to maintain the desired temperature over extended periods of time. For example, both alcohols and glycols such as methanol and ethylene glycol are known to react with glutaraldehyde so that, although addition of methanol and ethylene glycol to an aqueous solution of the glutaraldehyde initially lowers the freezing point, on storage will cause a freezing point rise as the alcohol and glycol reacts with glutaraldehyde and forms a mixture containing acetal bonds. It is therefore desirable to have a stable fixed freezing point.
Ifølge NO-søknad 814404 tilveiebringes det en fremgangsmåte for fremstilling av en vandig oppløsning inneholdende glutaraldehyd og med et stabilt, redusert frysepunkt. According to NO application 814404, a method for producing an aqueous solution containing glutaraldehyde and with a stable, reduced freezing point is provided.
Diette skjer ved at en blanding av glutaraldehyd og en alifatisk alkohol med 1-4 karbonatomer eller en alifatisk polyol med 2-6 karbonatomer eller blandinger av de nevnte alkoholer og polyoler, tilsettes en katalytisk mengde av en sterk syre. Dieting takes place by adding a catalytic amount of a strong acid to a mixture of glutaraldehyde and an aliphatic alcohol with 1-4 carbon atoms or an aliphatic polyol with 2-6 carbon atoms or mixtures of the aforementioned alcohols and polyols.
Tilsetningen av en katalytisk mengde av en sterk syre til den vandige glutaraldehydholdige oppløsning katalyserer hurtig dannelsen av likevektsblanding av glutaraldehydet, acetalet og frysepunktsreduksjonsmidler, hvorved likevektsblandingen oppviser et stabilt og fastlagt redusert frysepunkt. The addition of a catalytic amount of a strong acid to the aqueous glutaraldehyde-containing solution catalyzes the rapid formation of the equilibrium mixture of the glutaraldehyde, acetal and freezing point depressants, whereby the equilibrium mixture exhibits a stable and determined reduced freezing point.
Ifølge foreliggende oppfinnelse er det funnet at man kan oppnå en hurtig og virksom frisetting av aldehyd for aktiv kjemisk eller biologisk reaksjon. According to the present invention, it has been found that a rapid and effective release of aldehyde for active chemical or biological reaction can be achieved.
I henhold til dette angår foreliggende oppfinnelse en fremgangsmåte av den innledningsvis nevnte art og denne fremgangsmåte karakteriseres ved først å fortynne blandingen med vann og deretter å tilsette en katalytisk mengde av en sterk syre. According to this, the present invention relates to a method of the nature mentioned at the outset and this method is characterized by first diluting the mixture with water and then adding a catalytic amount of a strong acid.
De alifatiske alkoholer som kan benyttes som frysepunktsredu-serende midler inneholder som nevnt 1-4 karbonatomer slik som metanol, etanol og lignende, samt blandinger derav. Metanol er den foretrukne alkohol. The aliphatic alcohols which can be used as freezing point reducing agents contain, as mentioned, 1-4 carbon atoms such as methanol, ethanol and the like, as well as mixtures thereof. Methanol is the preferred alcohol.
De alifatiske polyoler som kan benyttes som frysepunktsredu-serende midler inneholder som nevnt 1-4 karbonatomer slik som metanol, etanol samt blandinger derav. Den foretrukne polyol er etylenglykol. The aliphatic polyols which can be used as freezing point reducing agents contain, as mentioned, 1-4 carbon atoms such as methanol, ethanol and mixtures thereof. The preferred polyol is ethylene glycol.
Det er klart at én eller flere alifatiske alkoholer kan blandes med én eller flere alifatiske polyoler. It is clear that one or more aliphatic alcohols can be mixed with one or more aliphatic polyols.
Syrene som er egnet for bruk ifølge oppfinnelsen er syrer istand til å gi en vandig pH-verdi under ca. 3,0 og for-trinnsvis under ca. 2,0 og omfatter fosforsyre, saltsyre, svovelsyre, trifluormetylsulfonsyre, para-toluensulfonsyre såvel som bårede sure katalysatorer som "Amberlyst" (en båret arylsulfonsyre) samt en kommersiell tilgjengelig båret fluorsulfonsyre "Nafion". The acids which are suitable for use according to the invention are acids capable of giving an aqueous pH value below approx. 3.0 and preferably below approx. 2.0 and includes phosphoric acid, hydrochloric acid, sulfuric acid, trifluoromethylsulfonic acid, para-toluenesulfonic acid as well as supported acid catalysts such as "Amberlyst" (a supported arylsulfonic acid) as well as a commercially available supported fluorosulfonic acid "Nafion".
For å oppnå et stabilt frysepunktsredusert produkt inneholder den vandige oppløsning generelt fra ca. 0,1 til ca. 50 vekt-# glutaraldehyd, fra ca. 5 til ca. 40 vekt-# alkohol og/eller glykol med resten vann slik at den totale oppløsning er 100 vekt-#. En foretrukket oppløsning inneholder 25 vekt-# glutaraldehyd, 30 vekt-£ alkohol og/eller glykol og 45 vekt-# vann. In order to achieve a stable freezing-point-reduced product, the aqueous solution generally contains from approx. 0.1 to approx. 50 wt-# glutaraldehyde, from approx. 5 to approx. 40 wt-# alcohol and/or glycol with the rest water so that the total solution is 100 wt-#. A preferred solution contains 25 wt-# glutaraldehyde, 30 wt-£ alcohol and/or glycol and 45 wt-# water.
For ifølge oppfinnelsen hurtig og effektivt å frigjøre glutaraldehydet for aktiv kjemisk og biologisk reaksjon bør den vandige oppløsning inneholde fra ca. 0,01 til ca. 10 vekt-# glutaraldehyd og en katalytisk mengde av en syre og kan inneholde opptil ca. 40 vekt-# alkohol og/eller polyol med resten vann slik at den totale oppløsning utgjør 100 vekt-#. According to the invention, in order to quickly and effectively release the glutaraldehyde for active chemical and biological reaction, the aqueous solution should contain from approx. 0.01 to approx. 10 wt-# of glutaraldehyde and a catalytic amount of an acid and can contain up to approx. 40 wt-# alcohol and/or polyol with the rest water so that the total solution amounts to 100 wt-#.
Oppløsningen kan inneholde andre additiver, for eksempel fargestoffer, overflateaktive midler, chelateringsmidler, pH-buffermidler eller lignende. The solution may contain other additives, for example dyes, surfactants, chelating agents, pH buffering agents or the like.
Eksempler. Examples.
De følgende eksempler er ment å gi spesifikke illustrasjoner på gjennomføring av oppfinnelsen, uten på noen måte å begrense denne. The following examples are intended to provide specific illustrations of the implementation of the invention, without limiting it in any way.
Kontroll A Control A
Frysepunktet for en blanding av 25 vekt-56 glutaraldehyd og 75 vekt-5fe vann er -5,5°C (bestemt ved fremgangsmåten som angitt i ASTM D-1177-65). The freezing point of a mixture of 25 wt-56 glutaraldehyde and 75 wt-5fe of water is -5.5°C (determined by the method specified in ASTM D-1177-65).
Kontroll B Control B
De følgende bestanddeler ble blandet: The following ingredients were mixed:
25 vekt-£ glutaraldehyd, 25 wt-£ glutaraldehyde,
25 vekt-# metanol og 25 wt-# methanol and
50 vekt-Sé vann. 50 weight-See water.
Frysepunktet for blandingen var -20"C og pH-verdien var 4 ,0. Etter lagring i 55 dager ved ca. 25'C ble frysepunktet for blandingen målt og funnet å være -22'C. The freezing point of the mixture was -20°C and the pH value was 4.0. After storage for 55 days at about 25°C, the freezing point of the mixture was measured and found to be -22°C.
Kontroll C Control C
De følgende bestanddeler ble blandet: The following ingredients were mixed:
25 vekt-# glutaraldehyd, 25 wt-# of glutaraldehyde,
25 vekt-# etylenglykol og 25 wt-# ethylene glycol and
5 0 vekt-% vann. 50% by weight water.
Frysepunktet for blandingen var -25,5°C og pH-verdien var ca. 4,0. Etter lagring i 55 dager ved ca. 25°C ble blandingens frysepunkt målt og funnet å være -22°C. The freezing point of the mixture was -25.5°C and the pH value was approx. 4.0. After storage for 55 days at approx. 25°C, the freezing point of the mixture was measured and found to be -22°C.
De følgende eksempler viser fremstilling av en oppløsning ifølge N0-søknad 814404. The following examples show the preparation of a solution according to NO application 814404.
Eksempel I Example I
De følgende bestanddeler ble blandet: The following ingredients were mixed:
25 vekt-# glutaraldehyd, 25 wt-# of glutaraldehyde,
25 vekt-# metanol og 25 wt-# methanol and
50 vekt-# vann. 50 wt-# of water.
En l#-ig oppløsning av fosforsyre ble tilsatt oppløsningen Inntil det var oppnådd en pH-verdi på 1-2. A l# solution of phosphoric acid was added to the solution until a pH value of 1-2 was achieved.
Frysepunktet for 1lkevektsblandlngen var -22,8°C. The freezing point for the 1-weight mixture was -22.8°C.
Eksempel II Example II
De følgende bestanddeler ble blandet: The following ingredients were mixed:
25 vekt-5É glutaraldehyd, 25 wt-5É glutaraldehyde,
25 vekt-& etylenglykol og 25 wt. & ethylene glycol and
50 vekt-5É vann. 50 weight-5É water.
En 1%- lg oppløsning av fosforsyre ble tilsatt til oppløsning-en inntil det var oppnådd en pH-verdi på 1-2. A 1% solution of phosphoric acid was added to the solution until a pH value of 1-2 had been achieved.
Frysepunktet for blandingen var -16,1°C. The freezing point of the mixture was -16.1°C.
Den vandige likevektsblanding i eksempel I og eksempel II ble tildannet i løpet av mindre enn 3 timer. Disse likevekts-blandinger er" istand til å bibeholde det angitte frysepunkt over lange tidsrom, selv etter 6 måneders lagring. The aqueous equilibrium mixture of Example I and Example II was formed in less than 3 hours. These equilibrium mixtures are capable of maintaining the specified freezing point over long periods of time, even after 6 months of storage.
I motsetning til dette varierte frysepunktene for blandingene i kontrollprøvene A og B betydelig etter kun 55 dager og opp til 3 måneder kunne være nødvendig for at det ble oppnådd likevekt. In contrast, the freezing points of the mixtures in control samples A and B varied significantly after only 55 days and up to 3 months could be required for equilibrium to be achieved.
De følgende eksempler illusterer oppfinnelsen. The following examples illustrate the invention.
Eksemplene 1- 5 Examples 1-5
I disse eksempler ble de følgende bestanddeler blandet: In these examples, the following ingredients were mixed:
25 vekt-56 glutaraldehyd, 25 wt-56 glutaraldehyde,
30 vekt-56 metanol og 30 wt-56 methanol and
45 vekt-56 vann. 45 weight-56 water.
Disse blandinger ble lagret i ca. 6 måneder. På dette tidspunkt var likevekt oppnådd for blandingen. Denne blanding ble fortynnet til 0, 1% av teoretisk glutaraldehyd. For å separere deler av blandingen ble det tilsatt 1%- ig oppløsning av fosforsyre inntil den ønskede pH-verdi var oppnådd. Prosentandelen glutaraldehyd gjenvunnet fra blandingen på forskjellige tidsrom og pH-verdier er vist i Tabell I. Glutaraldehydnivåene ble bestemt ved gasskromatografi. These mixtures were stored for approx. 6 months. At this point, equilibrium had been reached for the mixture. This mixture was diluted to 0.1% of theoretical glutaraldehyde. To separate parts of the mixture, a 1% solution of phosphoric acid was added until the desired pH value was achieved. The percentage of glutaraldehyde recovered from the mixture at various times and pH values is shown in Table I. Glutaraldehyde levels were determined by gas chromatography.
Eksemplene 6- 11 Examples 6-11
I disse eksempler ble de følgende bestanddeler blandet: In these examples, the following ingredients were mixed:
25 vekt-56 glutaraldehyd 25 wt-56 glutaraldehyde
30 vekt-& etylenglykol og 30 wt. & ethylene glycol and
45 vekt-5G vann. 45 weight-5G water.
Blandingen ble lagret i 6 måneder. På dette tidspunkt hadde blandingen nådd sin likevekt. Blandingen ble fortynnet til 0,1$ av teoretisk glutaraldehyd. For å separere deler av blandingen ble det tilsatt en l$-ig oppløsning av fosforsyre inntil den ønskede pH-verdi var oppnådd. Prosentandelen glutaraldehyd gjenvunnet fra blandingen på forskjellige tidsrom og pH-verdier er vist i Tabell II. Glutaraldehyd-nivået ble bestemt ved gasskromatografi. The mixture was stored for 6 months. At this point, the mixture had reached its equilibrium. The mixture was diluted to 0.1% of theoretical glutaraldehyde. In order to separate parts of the mixture, a 1% solution of phosphoric acid was added until the desired pH value was achieved. The percentage of glutaraldehyde recovered from the mixture at different times and pH values is shown in Table II. The glutaraldehyde level was determined by gas chromatography.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO864341A NO162961C (en) | 1980-12-30 | 1986-10-30 | PROCEDURE FOR RELEASEING GLUTARALDEHYDE FROM A MAJOR EQUAL WEIGHT MIXTURE. |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22150680A | 1980-12-30 | 1980-12-30 | |
| NO814404A NO156784C (en) | 1980-12-30 | 1981-12-22 | PROCEDURE FOR PREPARING A STABLE, Aqueous SOLUTION OF GLUTARALDEHYDE WITH STABLE, REDUCED FREEZING POINT. |
| NO864341A NO162961C (en) | 1980-12-30 | 1986-10-30 | PROCEDURE FOR RELEASEING GLUTARALDEHYDE FROM A MAJOR EQUAL WEIGHT MIXTURE. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO864341L NO864341L (en) | 1982-07-01 |
| NO162961B true NO162961B (en) | 1989-12-04 |
| NO162961C NO162961C (en) | 1990-03-14 |
Family
ID=27352813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO864341A NO162961C (en) | 1980-12-30 | 1986-10-30 | PROCEDURE FOR RELEASEING GLUTARALDEHYDE FROM A MAJOR EQUAL WEIGHT MIXTURE. |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO162961C (en) |
-
1986
- 1986-10-30 NO NO864341A patent/NO162961C/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO162961C (en) | 1990-03-14 |
| NO864341L (en) | 1982-07-01 |
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