NO850289L - POWDER DETERGENTS AND PROCEDURES FOR PREPARING THIS - Google Patents
POWDER DETERGENTS AND PROCEDURES FOR PREPARING THISInfo
- Publication number
- NO850289L NO850289L NO850289A NO850289A NO850289L NO 850289 L NO850289 L NO 850289L NO 850289 A NO850289 A NO 850289A NO 850289 A NO850289 A NO 850289A NO 850289 L NO850289 L NO 850289L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- weight
- atoms
- fabric softener
- component
- Prior art date
Links
- 239000003599 detergent Substances 0.000 title claims abstract description 29
- 239000000843 powder Substances 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
- 239000002979 fabric softener Substances 0.000 claims abstract description 24
- 235000012239 silicon dioxide Nutrition 0.000 claims abstract description 20
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000001450 anions Chemical class 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 239000000654 additive Substances 0.000 claims abstract description 8
- 239000000194 fatty acid Substances 0.000 claims abstract description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 8
- 239000013543 active substance Substances 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 6
- 229930195729 fatty acid Natural products 0.000 claims abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 10
- 230000002745 absorbent Effects 0.000 claims description 9
- 239000002250 absorbent Substances 0.000 claims description 9
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000000087 stabilizing effect Effects 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000003205 fragrance Substances 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000009736 wetting Methods 0.000 claims 1
- 239000003945 anionic surfactant Substances 0.000 abstract description 7
- 239000002736 nonionic surfactant Substances 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004902 Softening Agent Substances 0.000 abstract description 2
- 125000000129 anionic group Chemical group 0.000 abstract description 2
- 150000002431 hydrogen Chemical group 0.000 abstract description 2
- 239000003463 adsorbent Substances 0.000 abstract 2
- 238000005406 washing Methods 0.000 description 27
- 239000000203 mixture Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- 238000005520 cutting process Methods 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000002752 cationic softener Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
- SYWYECMALNGDPC-UHFFFAOYSA-N 2,2-dioxo-1,3,2-dioxathietan-4-ol Chemical compound OC1OS(=O)(=O)O1 SYWYECMALNGDPC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical group 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000004665 cationic fabric softener Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- -1 fatty acid amines Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005029 sieve analysis Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
- C11D3/124—Silicon containing, e.g. silica, silex, quartz or glass beads
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
Trommelvaskemaskiner, som hovedsakelig er vanligeDrum washing machines, which are mainly ordinary
i europeiske husholdinger, vasker som regel i to arbeids-operasjoner. I hovedvaskeoperasjonen blir vasken først renset ved hjelp av et vaskepulver. Derpå følger flere spyleoperasjoner. I det siste spylebad tilsettes et vaskemykningsmiddel ved efterbehandlingen. Dette skal gi vasken et mykt, flosset grep og behagelige bæreegenskaper, også når vasken må tørres under ugunstige betingelser. in European households, as a rule, washes in two working operations. In the main washing operation, the sink is first cleaned using a washing powder. This is followed by several flushing operations. In the last rinse bath, a fabric softener is added during the finishing process. This should give the wash a soft, frayed grip and comfortable carrying properties, even when the wash has to be dried under unfavorable conditions.
Forsøk på å forene vaskebehandlingene i en enkelt vaskeoperasjon, dvs. tilsette mykneren allerede til vaskepulveret, er allerede foretatt i mange tilfelle. Attempts to combine the washing treatments in a single washing operation, i.e. adding the softener already to the washing powder, have already been carried out in many cases.
De tidligere løsningsforsøk har overveiende den ulempe at den myknende virkning går tapt. Dette skyldes at det kationiske mykningsmiddel med det i overskudd tilstedeværende anioniske tensid i vaskemidlet danner tungtoppløselige salter og forblir uvirksomt i vaskevæsken. Derved er efter den avsluttende spyling neppe noen kationisk mykner påvisbar på tekstilet ennå. Slike produkter viser da også en meget utilfredsstillende mykgjørende virkning. The previous solution attempts mainly have the disadvantage that the softening effect is lost. This is because the cationic softener with the anionic surfactant present in excess in the detergent forms poorly soluble salts and remains inactive in the washing liquid. Thereby, after the final rinse, hardly any cationic softener is still detectable on the textile. Such products then also show a very unsatisfactory softening effect.
Allerede fremstillingen av slike vaskemidler inneholdende vaskemykningsmidler er problematisk. Ved fremstillingen av vaskepulver blir som reget et flytende forkonsentrat fremstilt (slurry) som derpå underkastes sprøytetørring. Already the production of such detergents containing fabric softeners is problematic. In the production of washing powder, as usual, a liquid pre-concentrate is produced (slurry) which is then subjected to spray drying.
Hvis mykningsmidlet allerede tilsettes dette forkonsentrat, danner det seg straks ved vaskemiddelfremstillingen et salt med de anioniske tensider. If the softener is already added to this pre-concentrate, a salt with the anionic surfactants is immediately formed during the preparation of the detergent.
Den ønskede forsinkede virksomhet er altså bare opp-nåelig når det kationiske mykningsmiddel foreligger i pulver-form og vaskepulveret deretter tilblandes. Da det kationiske mykningsmiddel imidlertid har en lavere krystallisa-sjonstilbøyelighet, er fremgangsmåten ved sprøytetørring ikke anvendbar. Også fremgangsmåten ved valsetørring gir på grunn av den langsomme krystallisasjon og konsolidering av produktet betraktelige vanskeligheter. Dessuten blir derved betraktelig krystallisasjonsvarme frigjort, hvilket fører til at det ferdig fremstilte pulver igjen sammenbakes. The desired delayed operation is therefore only achievable when the cationic softener is in powder form and the washing powder is then mixed in. However, since the cationic plasticizer has a lower crystallisation tendency, the method of spray drying is not applicable. Due to the slow crystallization and consolidation of the product, the method of roller drying also presents considerable difficulties. In addition, considerable heat of crystallization is thereby released, which causes the finished powder to be baked together again.
Det er derfor et behov for et pulverformig vaskemykningsmiddel som kan fremstilles problemfritt og kan til blandes til vanlige vaskemiddelpulvere og ved hvilket de ønskede mykningsegenskaper ikke går tapt i vaskeoperasjonen. There is therefore a need for a powdered detergent softener which can be produced without problems and can be mixed into ordinary detergent powders and in which the desired softening properties are not lost during the washing operation.
Et slikt pulverformig vaskemykningsmiddel fremstilles ifølge oppfinnelsen. Det består ifølge oppfinnelsen av: A) 60 til 80 vekt% av et vaskemykningsmiddel på basis av ett eller flere nitrogenholdige kationiske overflateaktive stoffer med i det minste en til nitrogenatomet bundet hydrocarbongruppe med minst 8 carbonatomer som eventuelt inneholder vanlige hjelpestoffer med stabiliserende eller gjenfuktende virkning og/eller tilsetningsstoffer, B) 20 til 40 vekt% høysugedyktig kiselsyre, idet komponenten A) er adsorbert på komponenten B). Such a powdered fabric softener is produced according to the invention. According to the invention, it consists of: A) 60 to 80% by weight of a fabric softener based on one or more nitrogen-containing cationic surface-active substances with at least one hydrocarbon group with at least 8 carbon atoms bound to the nitrogen atom, which possibly contains common auxiliary substances with a stabilizing or re-moistening effect and /or additives, B) 20 to 40% by weight highly absorbent silicic acid, the component A) being adsorbed on the component B).
Som kationiske overflateaktive stoffer kan man anvende de som vaskemyknere kjente lipofile grupper inneholdende kvartære ammoniumforbindelser og alkylimidazoliniumforbindelser med overflateaktive egenskaper. Slike forbindelser er f.eks. beskrevet i Chemistry and Industry, 1969, s. 893 - 894. As cationic surfactants, the lipophilic groups known as detergent softeners containing quaternary ammonium compounds and alkylimidazolinium compounds with surface-active properties can be used. Such compounds are e.g. described in Chemistry and Industry, 1969, pp. 893-894.
Fortrinnsvis består de pulverformige overflateaktive stoffer i komponent A) av minst én av de følgende forbindelser : Preferably, the powdered surfactants in component A) consist of at least one of the following compounds:
a) kvartære ammoniumforbindelser med formel:a) quaternary ammonium compounds of formula:
hvor R 1 og R 2er alkylgrupper med 8-24 carbonatomer, og where R 1 and R 2 are alkyl groups with 8-24 carbon atoms, and
R 3 og R<4>er alkylgrupper med 1-4 carbonatomer, og A- er et anion. b) Alkylimidazoliniumforbindelser med den generelle formel: R 3 and R<4> are alkyl groups with 1-4 carbon atoms, and A- is an anion. b) Alkylimidazolinium compounds with the general formula:
hvor R 5 er en alkylgruppe med 1-4 carbonatomer, R<6>er en alkylgruppe med 8-25 carbonatomer, R<7>er en alkylgruppe med 1-4 carbonatomer eller hydrogen, og R ger en alkylgruppe med 8-25 carbonatomer, og A- er et anion, eksempelvis methosulfat, ethosulfat eller et halogen. c) Kvartære ammoniumforbindelser med den generelle formel: where R 5 is an alkyl group with 1-4 carbon atoms, R<6>is an alkyl group with 8-25 carbon atoms, R<7>is an alkyl group with 1-4 carbon atoms or hydrogen, and R gives an alkyl group with 8-25 carbon atoms , and A- is an anion, for example methosulfate, ethosulfate or a halogen. c) Quaternary ammonium compounds with the general formula:
9 10 9 10
hvor R og R er alkylgrupper med 8 og 24 carbonatomer inneholdende fettsyreamidoalkylgrupper, R"^ er en alkylgruppe med 1-4 carbonatomer, R " er hydrogen eller methyl, x er et tall fra 1 - 5, og A- er et anion. where R and R are alkyl groups with 8 and 24 carbon atoms containing fatty acid amidoalkyl groups, R"^ is an alkyl group with 1-4 carbon atoms, R " is hydrogen or methyl, x is a number from 1 - 5, and A- is an anion.
Særlig foretrukket er herunder l-methyl-2-alkyl-3-fettsyreamidoethylimidazoliniummethosulfat. Among them, 1-methyl-2-alkyl-3-fatty acid amidoethylimidazolium methosulphate is particularly preferred.
Som grupper R"*", R", R^, R^, R^ og R anvendes vanligvis fettsyrealkylgrupper, fortrinnsvis med en C-kjedelengde på C 16 til C 18. As groups R"*", R", R^, R^, R^ and R, fatty acid alkyl groups are usually used, preferably with a C chain length of C 16 to C 18.
En rekke andre forbindelser som kommer på tale, er nevnt i EU - A - 406 og DE - A - 30 25 369. Særlig nevnes: methyl-bis-(talgamidoethyl)-2-hydroxypropylammoniummetholsul-fat, N,N-dimethyl-bis-(isopropanol-oljesyreester)-ammonium-metholsulfat, N-talg-pentamethylpropylendiammoniumklorid. A number of other compounds that come into question are mentioned in EU - A - 406 and DE - A - 30 25 369. Particular mention is made of: methyl-bis-(talgamidoethyl)-2-hydroxypropylammonium metholsulphate, N,N-dimethyl-bis -(isopropanol-oleic acid ester)-ammonium-methol sulfate, N-tallow-pentamethylpropylenediammonium chloride.
Som egnede hjelpestoffer kommer særlig ikke-ionogene tensider -i betraktning, som de f.eks. er beskrevet i DE - A - 30 25 369, særlig reaksjonsprodukter av fettsyre-ethanolamid eller fettsyreaminer med ethylenoxyd og/eller propylenoxyd som virker som dispergerings- eller emulgerings-midler, og eventuelt oppviser en ytterligere mykgjørende virkning. Non-ionic surfactants in particular come into consideration as suitable excipients, such as those e.g. is described in DE - A - 30 25 369, in particular reaction products of fatty acid ethanolamide or fatty acid amines with ethylene oxide and/or propylene oxide which act as dispersing or emulsifying agents, and possibly exhibit a further softening effect.
Andre ikke-ionogene emulgatorer er slike på basis av oxyalkylater, f.eks. reaksjonsprodukter av ethylenoxyd med alkylfenoler eller fettalkoholer. Som eksempel på slike hjelpestoffer kan nevnes: oleylalkoholpolyglycolether, nonylfenolpolyglycolether eller stearinsyremonoglycerid-polyglycolether. Other non-ionic emulsifiers are those based on oxyalkylates, e.g. reaction products of ethylene oxide with alkylphenols or fatty alcohols. Examples of such auxiliary substances can be mentioned: oleyl alcohol polyglycol ether, nonylphenol polyglycol ether or stearic acid monoglyceride polyglycol ether.
Vanlige tilsetningsstoffer er særlig duftstoffer, farvestoffer og optiske lysnere. Common additives are in particular fragrances, dyes and optical brighteners.
Som komponent B) anvendes en høysugedyktig kiselsyre særlig en med 250 til 600 m 2 /g, fortrinnsvis 350 til 500 m 2/g As component B) a highly absorbent silicic acid is used, particularly one with 250 to 600 m 2 /g, preferably 350 to 500 m 2 /g
(BET) .(BET) .
Egnede findelte, høysugedyktige bærer-kiselsyrer med størst mulig spesifikk overflate, fremstilles ved felning og sprøytetørring og kan erholdes i handelen. Suitable finely divided, highly absorbent carrier silicic acids with the largest possible specific surface are produced by felting and spray drying and can be obtained commercially.
En fremgangsmåte ifølge oppfinnelsen til fremstilling av pulverformige vaskemykningsmidler, erkarakterisert vedat man påfører 60 - 80 vektdeler av et vaskemykningsmiddel på basis av ett eller flere nitrogenholdige kationiske overflateaktive stoffer med minst én til nitrogenatomet bundet hydrocarbongruppe med minst 8 carbonatomer som eventuelt inneholder vanlige hjelpestoffer med stabiliserende eller gjenfuktende virkning og/eller tilsetningsstoffer, i en pulverblander, eventuelt sammen med hjelpe- og/eller duftstoffer på 20 - 40 vektdeler høysugedyktig kiselsyre. A method according to the invention for the production of powdery fabric softeners is characterized by applying 60 - 80 parts by weight of a fabric softener based on one or more nitrogen-containing cationic surface-active substances with at least one hydrocarbon group bound to the nitrogen atom with at least 8 carbon atoms, which possibly contain common auxiliary substances with stabilizing or moisturizing effect and/or additives, in a powder mixer, possibly together with auxiliaries and/or fragrances of 20 - 40 parts by weight highly absorbent silicic acid.
En egnet blander er eksempelvis den i handelen værende "Pflugschar-blander". A suitable mixer is, for example, the commercially available "Pflugschar mixer".
Kiselsyren tilblandes den kationiske mykner, idet hver av de ovenfor nevnte kvartære imidazolinium- og ammoniumforbindelser kan medanvendes, likegyldig hvilken struktur den enkelte har. Videre påvirkes ikke egenskapene av mykneren ved typen av anionet. Det er herved også likegyldig om mykneren foreligger i flytende form eller først må smeltes for å tilsettes kiselsyren som smelte. De i handelen til-gjengelige kvartære myknere inneholder videre ofte oppløs-ningsmidler, særlig lavere alkoholer og glycoler, som f.eks. isopropanol, 1,2-propylenglycol eller hexylenglycol. Disse oppløsningsmidler forstyrrer i alminnelighet ikke, dvs. The silicic acid is mixed with the cationic plasticizer, as each of the quaternary imidazolinium and ammonium compounds mentioned above can be used together, regardless of the structure of the individual. Furthermore, the properties of the plasticizer are not affected by the type of anion. It is also irrelevant whether the plasticizer is in liquid form or must first be melted in order to add the silicic acid as a melt. The commercially available quaternary plasticizers also often contain solvents, especially lower alcohols and glycols, such as e.g. isopropanol, 1,2-propylene glycol or hexylene glycol. These solvents generally do not interfere, i.e.
en mykner med inntil 25% isopropanol kan blandes med f.eks. kiselsyre til et fint pulver. a plasticizer with up to 25% isopropanol can be mixed with e.g. silicic acid to a fine powder.
Herved er det i alminnelighet ved viderebearbeidelsen av pulveret nødvendig å treffe sikkerhetsforholdsregler på grunn av de dannede oppløsningsmiddeldamper. In this way, it is generally necessary to take safety precautions during the further processing of the powder due to the solvent vapors formed.
Likeledes kan vaskemykningsmidler som bringes i handelen i de ovennevnte ikke-ionogene tensider, påføres på slike oppløsninger på kiselsyren. De sammen med den kationiske vaskemykner påførte ikke-ioniske tensider, forstyrrer selvsagt ikke ved vaskebehandlingen. Likewise, detergent softeners that are sold in the above-mentioned non-ionic surfactants can be applied to such solutions on the silicic acid. The non-ionic surfactants applied together with the cationic fabric softener obviously do not interfere with the washing process.
Oppfinnelsen angår videre et vaskemiddel med mykgjør-ende egenskaper som erkarakterisert vedat det som vaskemykningsmiddel inneholder 5 til 2 5 vekt% av et pulverformig vaskemykningsmiddel som består av A) 60 til 80 vekt% av et vaskemykningsmiddel på basis av ett eller flere nitrogenholdige, kationiske, overflateaktive stoffer med minst én til nitrogenatomet bundet hydrocarbongruppe med minst 8 carbonatomer, som eventuelt inneholder vanlige hjelpestoffer med stabiliserende eller gjenværende virkning og/eller tilsetningsstoffer, The invention further relates to a detergent with softening properties which is characterized in that it contains, as detergent softener, 5 to 25% by weight of a powdered detergent softener consisting of A) 60 to 80% by weight of a detergent softener based on one or more nitrogen-containing, cationic, surface-active substances with at least one hydrocarbon group with at least 8 carbon atoms bound to the nitrogen atom, which possibly contain common auxiliary substances with a stabilizing or residual effect and/or additives,
og and
B) 20 til 40 vekt% høysugedyktig kiselsyre, idet komponenten A) er adsorbert på komponenten B). B) 20 to 40% by weight highly absorbent silicic acid, the component A) being adsorbed on the component B).
Det pulverformige vaskemykningsmiddel kan ifølge oppfinnelsen problemfritt blandes til de vanlige husholdnings-vaskemidler for fullvask eller 60°-vask. According to the invention, the powdered fabric softener can easily be mixed with the usual household detergents for full washing or 60° washing.
Herved skal det passes på at kornstørrelsen av vaskepulver og vaskemykningspulver ifølge oppfinnelsen ikke er for forskjellig slik at en adskillelse unngåes. Vaskepulver ligger for det meste i et størrelsesområde fra 450 til 500^u. Et typisk- mykningspulver ifølge eksempel 2 oppviser en korn-størrelsesfordeling ifølge følgende siktanalyse: 100 - 200 u : 10,9 % Hereby, care must be taken that the grain size of washing powder and washing softening powder according to the invention is not too different so that a separation is avoided. Washing powder is mostly in a size range from 450 to 500 ^u. A typical softening powder according to example 2 exhibits a grain size distribution according to the following sieve analysis: 100 - 200 u : 10.9%
200 - 300 n : 47,2 % 200 - 300 n : 47.2%
300 - 400 n : 29,1 % 300 - 400 n : 29.1%
400 - 500 n : 12,8 % 400 - 500 n : 12.8%
Denne fordeling er som regel egnet. For bedre til-pasning til kornstørrelsen av vaskemidlet kan myknings-pulveret ved en passende føring av hastighet og temperatur av plogskjærblanderen pågranuleres. Derved økes kornstørr-elsen til det to- til tredobbelte. This distribution is usually suitable. For a better adaptation to the grain size of the detergent, the softening powder can be granulated by suitable control of speed and temperature of the ploughshare mixer. Thereby, the grain size is increased two to threefold.
Egnede typiske vaskemiddelformuleringer med tilsvarende rammereseptur er eksempelvis beskrevet i Tensid-Taschenbuch, 2. oppi., Carl Hanser Verlag, Miinchen/Wien og i "Wasch-mittelchemie", Hiithig-Verlag, Heidelberg (1976). Suitable typical detergent formulations with corresponding framework recipes are described, for example, in Tensid-Taschenbuch, 2nd oppi., Carl Hanser Verlag, Munich/Vienna and in "Wasch-mittelchemie", Hiithig-Verlag, Heidelberg (1976).
Slike vaskemidler er vanligvis basert på anioniske og ikke-ioniske tensider såvel som eventuelt skuminhibitorer, og inneholder vanligvis kompleksdanner, ioneutbytter, bleke-midler, blekeaktivatorer, stabilisatorer, forgrånings-inhibitorer, enzymer, optiske lysningsmidler, korrosjons-inhibitorer, duftsstoffer, farvestoffer, elektrolytter. Such detergents are usually based on anionic and non-ionic surfactants as well as possibly foam inhibitors, and usually contain complex formers, ion exchangers, bleaching agents, bleaching activators, stabilizers, graying inhibitors, enzymes, optical brighteners, corrosion inhibitors, fragrances, dyes, electrolytes .
Overraskende oppviser vaskemykningsmidlene ifølge oppfinnelsen ikke de ovennevnte ulemper ved vaskemykningsmidler tilsatt til kjente vaskemidler. Surprisingly, the fabric softeners according to the invention do not exhibit the above-mentioned disadvantages of fabric softeners added to known detergents.
Vaskemykningsmidlene ifølge oppfinnelsen kan fremstilles problemfritt og som pulver tilblandes vanlige vaskemiddelpulvere. Kompleksdannelsen med de kationiske bestanddeler av vaskemykningsmidlet ifølge oppfinnelsen med anioniske tensider opptrer ikke. I stedet danner den krystallinske struktur av vaskemykningsmidlet ifølge oppfinnelsen en sikker forsinket oppløsning av den kationiske vaskemiddelmykner-komponent slik at under vaskeoperasjoner blir ved det lett oppløselige anioniske tensid smusset løst fra trådene og opp-løst i vaskevannet, hvorved anion-tensidet forbrukes tilsvarende. Det forsinket oppløsende kationiske mykningsmiddel kan herunder uhindret tiltrekkes på fibrene. Den i vaskemyk ningsmidlet inneholdte bærerkiselsyre forblir i vaskevannet og er ikke lenger påvisbar på det ferdigvaskede tekstil. Negativ innvirkning på vaskeoperasjonen, vasketøyet eller vaskemaskinen har ikke kunnet påvises. The detergent softeners according to the invention can be produced without any problems and ordinary detergent powders are mixed as a powder. Complex formation with the cationic components of the fabric softener according to the invention with anionic surfactants does not occur. Instead, the crystalline structure of the detergent softener according to the invention forms a safe delayed dissolution of the cationic detergent softener component so that during washing operations the dirt is loosened from the threads and dissolved in the wash water by the easily soluble anionic surfactant, whereby the anionic surfactant is consumed accordingly. The delayed-dissolving cationic softener can therefore be attracted to the fibers unimpeded. The carrier silicic acid contained in the fabric softener remains in the wash water and is no longer detectable on the finished textile. A negative impact on the washing operation, the laundry or the washing machine has not been demonstrated.
De følgende eksempler viser fremstillingen av vaskemykningsmidlet ifølge oppfinnelsen. The following examples show the production of the fabric softener according to the invention.
Som vaskepulver anvendes et i handelen værende fullvaskemiddel med følgende sammensetning: As washing powder, a commercially available full detergent with the following composition is used:
Eksempel 1 Example 1
30 vektdeler kiselsyre med en overflate på 500 m 2/g (Sipernat 50 S, Degussa) anbringes i en 'Loedige" blander. Under stadig omrøring tilsettes langsomt en smelte av 70 deler dimethyldistearylammoniumklorid. Blandingen blir slik innstilt på optimal skjæring. Man rører fortsatt i ca. 30 parts by weight of silicic acid with a surface area of 500 m 2 /g (Sipernat 50 S, Degussa) is placed in a 'Loedige' mixer. With constant stirring, a melt of 70 parts dimethyldistearylammonium chloride is slowly added. The mixture is thus set to optimal cutting. Stirring is continued for approx.
30 minutter og får et frittflytende pulver.30 minutes and get a free-flowing powder.
Eksempel 2Example 2
28 vektdeler kiselsyre med en overflate på 450 m 2/g ("Sipernat" 50, Degussa) anbringes under langsom omrøring i en "Loedige" blander under langsom omrøring, og 7 2 vektdeler av en oppløsning av 75% l-methyl-2-talgalkyl-3-talgamido-ethylimidazoniniummethosulfat i 25% isopropanol blir under løpende blander påsprøytet ved hjelp av en egnet dyse med et trykk på 3 bar. Blanderen innstilles på optimal skjæring. 28 parts by weight of silicic acid with a surface area of 450 m 2 /g ("Sipernat" 50, Degussa) are placed under slow stirring in a "Loedige" mixer under slow stirring, and 7 2 parts by weight of a solution of 75% l-methyl-2- tallow alkyl-3-tallow gamido-ethylimidazoninium methosulphate in 25% isopropanol is sprayed on while stirring using a suitable nozzle at a pressure of 3 bar. The mixer is set to optimal cutting.
Man blander i ytterligere 20 minutter inntil et jevnt, flytende pulver fritt for klumper erholdes. Mix for a further 20 minutes until a smooth, liquid powder free of lumps is obtained.
Eksempel 3Example 3
I en plogskjæremaskin (Loedige) anbringes 24 vektdeler bærerkiselsyre, og under stadig blanding med en hastighet på 120 o/min innsprøytes så 68 vektdeler l-methyl-2-oleyl-alkyl-3-amidoethyl-imidazoliniummethosulfat ufortynnet. In a ploughshare machine (Loedige) 24 parts by weight of carrier silicic acid are placed, and under constant mixing at a speed of 120 rpm, 68 parts by weight of undiluted 1-methyl-2-oleyl-alkyl-3-amidoethyl-imidazolium methosulphate are injected.
Derpå påsprøytes på samme måte 8 vektdeler nonylfenolpolyglycolether. Blanderen innstilles så på optimal skjæring og kjøres under skjæring i 30 minutter inntil pulverets korn-størrelse har stabilisert seg. Pulveret er da ferdig til av-fylling. Then 8 parts by weight of nonylphenol polyglycol ether are sprayed on in the same way. The mixer is then set to optimum cutting and run during cutting for 30 minutes until the powder's grain size has stabilised. The powder is then ready for filling.
Eksempel 4Example 4
For fremstilling av et mykningsgjørende vaskepulver anbringes i en plogskjærblander (Loedige) først 4,5 vektdeler bærerkiselsyre, og derpå blir under stadig blanding 10,5 vektdeler at en smeltet blanding av 75% N,N-bis-talgamidoethyl-N-(2-hydroxyethyl)-N-methylammoniummethosulfat og 25% 1,2-propylenglycol påsprøytet på kiselsyren. Blandingsoperasjonen fortsettes deretter i 30 minutter under optimal skjæring inntil kornstørrelsen er avpasset til det vaskepulver som ska,l anvendes. For the production of a softening washing powder, first 4.5 parts by weight of carrier silicic acid are placed in a plowshare mixer (Loedige), and then, with constant mixing, 10.5 parts by weight become a molten mixture of 75% N,N-bis-talgamidoethyl-N-(2- hydroxyethyl)-N-methylammonium methosulfate and 25% 1,2-propylene glycol sprayed onto the silicic acid. The mixing operation is then continued for 30 minutes under optimal cutting until the grain size is adapted to the washing powder to be used.
Deretter blir uten skjæring under stadig blanding ved ca, 100 o/min 85 vektdeler av et i handelen vanlig, ved sprøytetørring fremstilt vaskepulver tilsatt, og blandingen ble fortsatt (ca. 20 min) inntil det ble dannet et homogent pulver, Then, without cutting, while constantly mixing at approx. 100 rpm, 85 parts by weight of a commercially available, spray-dried washing powder is added, and the mix was continued (approx. 20 min) until a homogeneous powder was formed,
Eksempel 5Example 5
De i tabellen angitte mykningsmiddelformuleringer ble fremstilt på samme måte som beskrevet i eksempel 3. The plasticizer formulations indicated in the table were prepared in the same way as described in example 3.
Virkningsraåten av vaskemidlet inneholdende vaskemykningsmidlet ifølge oppfinnelsen, blir påvist ved følgende vaskeforsøk. Som vaskemiddel ble anvendt et i handelen vanlig produkt med den ovenfor angitte sammensetning. Som mykningsmiddel ble de følgende i handelen vanlige kvartære ammoniumforbindelser anvendt: The effectiveness of the detergent containing the fabric softener according to the invention is demonstrated by the following washing test. A commercially available product with the above-mentioned composition was used as detergent. The following commercially common quaternary ammonium compounds were used as softeners:
1. dimethyldistearylammoniumklorid1. dimethyldistearylammonium chloride
2. l-methyl-2-talgalkyl-3-talgamidoethylimidazolinium-methosulfat 2. 1-methyl-2-tallow alkyl-3-tallow gamidoethylimidazolinium methosulfate
Begge mykningsmidler inneholder ca. 25% isopropanol. Hver gang ble 70 vektdeler av mykneren adsorbert på 30 vektdeler felt bærerkiselsyre med en spesiell overflate på Both softeners contain approx. 25% isopropanol. Each time, 70 parts by weight of the plasticizer were adsorbed on 30 parts by weight of field silica support with a special surface of
450 m 2/g (etter BET) i en plogskjærblander.450 m 2 /g (after BET) in a ploughshare mixer.
Vaskingen ble gjort med standardvalkefrottévev i enThe washing was done with standard valke terry cloth in one
i handelen vanlig husholdnings-fullvaskemaskin. Vasketempera-turen utgjorde fortrinnsvis 60°C. Bedømmelsen av den myk-gjørende virkning skjedde ved parvis statistiske sammenlign-inger med 25 forsøkspersoner. I denne test betyr 50 punkter = meget myk og 0 punkter = ubehandlet råvev. Resultatene kan taes ut av følgende tabell: in the trade ordinary household full washing machine. The washing temperature was preferably 60°C. The assessment of the softening effect took place by pairwise statistical comparisons with 25 subjects. In this test, 50 points = very soft and 0 points = untreated raw tissue. The results can be taken from the following table:
På samme måte ble vaskemiddel som inneholder myknings-middelformuleringene i tabellen, prøvet med hensyn på deres mykningsgjørende virkning (tilsatt ble igjen et i handelen vanlig fullvaskemiddel med den ovenfor angitte sammensetning). Resultatene er angitt i tabell 3: In the same way, detergents containing the softening agent formulations in the table were tested with regard to their softening effect (a commercially available full detergent with the above-mentioned composition was again added). The results are shown in table 3:
Claims (7)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843402437 DE3402437A1 (en) | 1984-01-25 | 1984-01-25 | POWDERED SOFT SOFT DETERGENT, METHOD FOR THE PRODUCTION THEREOF AND DETERGENT CONTAINING THIS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO850289L true NO850289L (en) | 1985-07-26 |
Family
ID=6225822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO850289A NO850289L (en) | 1984-01-25 | 1985-01-24 | POWDER DETERGENTS AND PROCEDURES FOR PREPARING THIS |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0151936B1 (en) |
| JP (1) | JPS60221492A (en) |
| AT (1) | ATE42763T1 (en) |
| AU (1) | AU578261B2 (en) |
| CA (1) | CA1230454A (en) |
| DE (2) | DE3402437A1 (en) |
| DK (1) | DK162657B (en) |
| NO (1) | NO850289L (en) |
| ZA (1) | ZA85625B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3243983C2 (en) * | 1982-11-27 | 1984-11-22 | Degussa Ag, 6000 Frankfurt | Laundry softener concentrate |
| DE3434709A1 (en) * | 1984-09-21 | 1986-04-03 | Hoechst Ag, 6230 Frankfurt | ADSORBENTS BASED ON ORGANOPHILIC MODIFIED LAYERED SILICA |
| US4919846A (en) * | 1986-05-27 | 1990-04-24 | Shiseido Company Ltd. | Detergent composition containing a quaternary ammonium cationic surfactant and a carboxylate anionic surfactant |
| JPH0633405B2 (en) * | 1986-05-27 | 1994-05-02 | 株式会社資生堂 | Cleaning composition |
| FR2636342A1 (en) * | 1988-09-13 | 1990-03-16 | Rhone Poulenc Chimie | SUPPORTED LIQUID CONSTITUENTS AND DETERGENT FORMULAS CONTAINING THE SAME |
| EP0523287A1 (en) * | 1991-07-18 | 1993-01-20 | The Procter & Gamble Company | Perfume additives for fabric-softening compositions |
| DE4301266C2 (en) * | 1993-01-19 | 1996-02-01 | Wolfgang Metzger | New perfume complex composition with improved substantivity and its use |
| GB2313602A (en) * | 1996-05-31 | 1997-12-03 | Procter & Gamble | Detergent compositions |
| US7288498B1 (en) | 1997-03-18 | 2007-10-30 | Selecto, Inc | Transition metal oxide-aluminosilicate purification media |
| DE19721885A1 (en) * | 1997-05-26 | 1998-12-03 | Henkel Kgaa | Process for the production of granules containing cationic surfactants |
| WO2002081612A1 (en) * | 2001-04-03 | 2002-10-17 | Ciba Specialty Chemicals Holding Inc. | Fabric softene compositions |
| JP4884848B2 (en) * | 2006-06-01 | 2012-02-29 | 花王株式会社 | Rheology modifier |
| GB2507750A (en) * | 2012-11-07 | 2014-05-14 | Intelligent Fabric Technologies Plc | Fabric softener with colloidal silica for imparting stain resistant properties |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA755347B (en) * | 1974-09-06 | 1977-04-27 | Colgate Palmolive Co | Fabric softening composition containing molecular sieve zeolite |
| CH646742A5 (en) * | 1977-07-06 | 1984-12-14 | Procter & Gamble | CONCENTRATED LIQUID SOFTENER COMPOSITION. |
| US4149977A (en) * | 1978-01-10 | 1979-04-17 | Economics Laboratory, Inc. | Treatment of fabrics in machine dryers |
| DE2948921A1 (en) * | 1978-03-13 | 1980-11-06 | Procter & Gamble | LOW PHOSPHATE LAUNDRY DETERGENTS |
| US4203851A (en) * | 1978-06-16 | 1980-05-20 | Colgate-Palmolive Company | Fabric softening compositions and methods for manufacture thereof |
| EP0008829A1 (en) * | 1978-09-09 | 1980-03-19 | THE PROCTER & GAMBLE COMPANY | Controlled sudsing detergent compositions |
| JPS598794A (en) * | 1982-07-05 | 1984-01-18 | ライオン株式会社 | Additive for granular detergent |
| DE3243983C2 (en) * | 1982-11-27 | 1984-11-22 | Degussa Ag, 6000 Frankfurt | Laundry softener concentrate |
| US4642258A (en) * | 1983-07-05 | 1987-02-10 | Economics Laboratory, Inc. | Treatment of fabrics in machine dryers using treating means containing fabric treating composition having resistance to change in viscosity and release rate with temperature change |
-
1984
- 1984-01-25 DE DE19843402437 patent/DE3402437A1/en not_active Withdrawn
-
1985
- 1985-01-12 DE DE8585100278T patent/DE3569939D1/en not_active Expired
- 1985-01-12 EP EP85100278A patent/EP0151936B1/en not_active Expired
- 1985-01-12 AT AT85100278T patent/ATE42763T1/en not_active IP Right Cessation
- 1985-01-14 DK DK016885A patent/DK162657B/en not_active Application Discontinuation
- 1985-01-16 CA CA000472217A patent/CA1230454A/en not_active Expired
- 1985-01-16 AU AU37722/85A patent/AU578261B2/en not_active Ceased
- 1985-01-23 JP JP60009308A patent/JPS60221492A/en active Pending
- 1985-01-24 NO NO850289A patent/NO850289L/en unknown
- 1985-01-25 ZA ZA85625A patent/ZA85625B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0151936A2 (en) | 1985-08-21 |
| DK16885D0 (en) | 1985-01-14 |
| DE3569939D1 (en) | 1989-06-08 |
| EP0151936A3 (en) | 1986-11-20 |
| DK16885A (en) | 1985-07-26 |
| DK162657B (en) | 1991-11-25 |
| ATE42763T1 (en) | 1989-05-15 |
| AU3772285A (en) | 1985-08-01 |
| EP0151936B1 (en) | 1989-05-03 |
| ZA85625B (en) | 1985-09-25 |
| AU578261B2 (en) | 1988-10-20 |
| JPS60221492A (en) | 1985-11-06 |
| DE3402437A1 (en) | 1985-07-25 |
| CA1230454A (en) | 1987-12-22 |
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