EP0025165A1 - Esters quaternaires d'hydroxyalkylamidoamines, procédé pour leur préparation et leur utilisation comme agents d'adoucissement de textiles - Google Patents
Esters quaternaires d'hydroxyalkylamidoamines, procédé pour leur préparation et leur utilisation comme agents d'adoucissement de textiles Download PDFInfo
- Publication number
- EP0025165A1 EP0025165A1 EP19800105053 EP80105053A EP0025165A1 EP 0025165 A1 EP0025165 A1 EP 0025165A1 EP 19800105053 EP19800105053 EP 19800105053 EP 80105053 A EP80105053 A EP 80105053A EP 0025165 A1 EP0025165 A1 EP 0025165A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- formula
- hydrogen
- methyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002148 esters Chemical group 0.000 title abstract description 7
- 150000001412 amines Chemical class 0.000 title description 2
- 239000004744 fabric Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 239000002979 fabric softener Substances 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkyl phosphate anion Chemical group 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 150000001805 chlorine compounds Chemical group 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- SEPFQHJECFKHGD-UHFFFAOYSA-N henicos-2-ene Chemical group CCCCCCCCCCCCCCCCCCC=CC SEPFQHJECFKHGD-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 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
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines
Definitions
- the invention relates to quaternary esters of hydroxyalkylamidoamines having the general formula 1.
- R 1 and P 3 are alkyl or alkenyl with 7 to 24 C atoms, R 2 alkyl or hydroxyalkyl with 1 to 4 C atoms or benzyl, R 4 is hydrogen or methyl, R 5 is hydrogen or alkyl with 1 to 6 C atoms , m 2 or 3, n is a number from 1 to 8 and X is a halogen, alkyl sulfate or alkyl phosphate anion.
- R 1 and R 3 are alkyl having 15 to 22 carbon atoms
- R 2 is methyl
- R 4 is hydrogen
- R 5 is hydrogen or methyl
- m 3 is a number from 1 to 3
- X. is a chloride or methosulfate anion.
- These compounds are prepared by first using a diamine of the general formula 2 in an equimolar amount with a carboxylic acid of the general formula 3 implements.
- the resulting amidoamine of Formula 4 is in the second reaction step with an alkylene oxide of formula 5 to the hydroxyalkylamidoamine of the formula 6 implemented.
- This compound is esterified with a fatty acid R 3 COOH and reacted in the last step with an alkylating agent of the formula R 2 X to the quaternary esters according to the invention.
- the reaction of the diamine (2) in the first stage with the carboxylic acid (3) is carried out in an inert solvent or, preferably, in bulk at temperatures from 120 to 200 ° C., preferably at 140 to 180 ° C. with simultaneous removal of the water of reaction formed. It goes without saying that derivatives such as acid chlorides or acid anhydrides can also be used instead of the free acids. The complete course of the reaction is controlled via the acid number.
- the resulting amidoamines (4) are in a known manner with an alkylene oxide such as ethylene oxide or propylene oxide, mixtures of these two or with both agents successively, but preferably with ethylene oxide alone to the Hydroxialkylamidoaminen (6).
- an alkylene oxide such as ethylene oxide or propylene oxide
- the esterification of the hydroxiamidoamines (6) is carried out by known methods in higher-boiling inert solvents such as toluene or xylene or preferably in bulk with stoichiometric or slightly sub-stoichiometric amounts of a fatty acid R 3 COOH.
- the reflux temperature of the reaction mixture is expediently chosen as the reaction temperature and the water of reaction formed is removed azeotropically.
- the water of reaction is distilled off directly from the reaction mixture.
- the reaction temperatures here are 140 to 220 ° C, preferably 150 to 180 ° C.
- An acid catalyst such as p-toluenesulfonic acid is used to accelerate the reaction. The completeness of the reaction is checked by determining the acid number.
- esters of hydroxyalkylamidoamines thus obtained are then dissolved in an alcohol or, preferably, dispersed in water and reacted with an alkylating agent R 2 X at temperatures below 100 ° C., preferably at 40 to 80 ° C., to give the quaternary products according to the invention.
- This reaction can also be carried out without any solvent.
- the pure compounds of the formula (1) are obtained.
- the process is carried out in aqueous dispersion, with 20% aqueous dispersions of the compounds (1) being obtained directly, which, after appropriate dilution with water and preparation, can be used directly as fabric softener.
- Diamines of the formula (2) used with preference are the industrially available products tallow fat propylene diamine or stearyl propylene diamine. But it is according to the inven It is equally possible to use other diamines with a more or less wide alkyl chain distribution. Such diamines are produced in a known manner by adding acrylonitrile to primary fatty amines and then catalytically hydrogenating the propionitriles. For the amidation with the carboxylic acid 3, formic acid or acetic acid is preferably used.
- Fatty acids suitable for esterification are natural or synthetic products such as Palmitic acid, stearic acid, behenic acid or branched chain compounds from oxo synthesis such as e.g. Isostearic acid or mixtures of the ones mentioned, e.g. accrued from natural cuts derived from coconut oil or tallow.
- the alkylating agent used is preferably methyl chloride or dimethyl sulfate.
- the crfindungsdorfen compounds of formula (1) are suitable as a laundry Weichs p ülstoff and be in the form of aqueous dispersions with an active substance content of 1 to 15 wt .-%, usually 4 - 10 wt .-% of compounds of formula 1 following the wash the textile material in the last rinsing bath. The textile material is then dried.
- These fabric softeners can also contain other substances and auxiliaries that are commonly used in fabric softeners. These include, for example, cationic or nonionic surface-active substances, electrolytes, acidifying agents, organic complexing agents, optical brighteners or solubilizers as well as colorants and fragrances.
- the products are used to additionally influence the handle of the goods or other properties of the textiles to be treated or to adjust the viscosity, regulate the pH or increase the cold stability of the solutions.
- the compounds according to the invention give any textile materials, especially those made from natural or regenerated cellulose, wool cellulose acetate, triacetate, polyamide, polyacrylonitrile, polyester, polypropylene, a pleasant and soft feel.
- Use as a laundry treatment agent for terry and underwear is particularly advantageous.
- the mixture is stirred at 140 ° C. for 2 hours and allowed to cool.
- a medium-strong nitrogen stream is passed through the reaction mixture at 50 ° C. under vacuum for 1 hour.
- 235 g of pourable, viscous product are obtained, which is transferred to a glass flask.
- 122 g (0.45 mol) of technical stearic acid, 0.3 g of p-toluenesulfonic acid and 0.25 g of hydrazine hydrate are added and the mixture is heated to 170 ° C. with a blanket of nitrogen. Water distills off via a descending cooler. After four hours of stirring at 170 ° C., the acid number is less than 5.
- Example 1 The procedure described in Example 1 is followed with the following amounts: To simplify matters, the entire synthesis can be carried out in an autoclave. In this case, devices for dropping and distilling off must be attached during the condensation steps.
- A statistical mixture of 1 mol -CH 2 -CH 2 -O- and 0.7 mol
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2936121 | 1979-09-07 | ||
| DE19792936121 DE2936121A1 (de) | 1979-09-07 | 1979-09-07 | Quaternaere ester von hydroxialkylamidoaminen, verfahren zu deren herstellung und deren verwendung als waescheweichspuelmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0025165A1 true EP0025165A1 (fr) | 1981-03-18 |
Family
ID=6080249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19800105053 Withdrawn EP0025165A1 (fr) | 1979-09-07 | 1980-08-26 | Esters quaternaires d'hydroxyalkylamidoamines, procédé pour leur préparation et leur utilisation comme agents d'adoucissement de textiles |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0025165A1 (fr) |
| JP (1) | JPS5645446A (fr) |
| AR (1) | AR221961A1 (fr) |
| BR (1) | BR8005664A (fr) |
| DE (1) | DE2936121A1 (fr) |
| ES (1) | ES494707A0 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0316701A2 (fr) * | 1987-11-14 | 1989-05-24 | Henkel Kommanditgesellschaft auf Aktien | Sels quaternaires d'amidoammonium, procédé de préparation et utilisation |
| EP0643128A1 (fr) * | 1993-09-10 | 1995-03-15 | Kao Corporation | Compositions adoucinants aqueuses, nouveau sel d'ammonium quaternaire et procédé pour la préparation de ce sel |
| EP0707059A3 (fr) * | 1994-10-14 | 2001-04-18 | Kao Corporation | Composition adoucissante liquide, son utilisation et procédé de préparation d'un sel d'ammonium quaternaire |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4577196A (en) * | 1983-04-01 | 1986-03-18 | Hughes Aircraft Company | Missile mounted waveguide antenna |
| US4737741A (en) * | 1986-10-20 | 1988-04-12 | Hughes Aircraft Company | Orthogonal mode electromagnetic wave launcher |
| JPH0618287B2 (ja) * | 1987-01-28 | 1994-03-09 | 富士通株式会社 | 超小形広帯域アンテナ |
| SE9001862D0 (sv) * | 1990-05-23 | 1990-05-23 | Berol Nobel Ab | Nya kvaeveinnehaallande foereningar, foerfarande foer deras framstaellning samt anvaendning av foereningarna |
| DE4135115A1 (de) * | 1991-10-24 | 1993-04-29 | Trigon Chemie Gmbh | Kationaktive tenside |
| WO2017151552A1 (fr) | 2016-03-01 | 2017-09-08 | Ecolab Usa Inc. | Rinçage désinfectant basé sur une synergie d'agents tensioactifs anioniques quaternaires |
| CA3031505C (fr) | 2016-08-11 | 2021-09-14 | Ecolab Usa Inc. | Interaction entre des composes quaternaires antimicrobiens et des tensioactifs anioniques |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2104475A1 (en) * | 1971-02-01 | 1972-08-17 | Henkel & Cie GmbH, 4000 Düsseldorf | N-(acylaminoalkyl)-n-(3-hydroxy-1-propenyl)-dialkylammonium - salts - useful as textile-softening agents |
| US4039565A (en) * | 1975-06-26 | 1977-08-02 | Ashland Oil, Inc. | Quaternized amidoamines |
| DE2725780A1 (de) * | 1977-06-03 | 1978-12-14 | Miranol Chemical Co | Stickstoffhaltige kondensationsprodukte |
-
1979
- 1979-09-07 DE DE19792936121 patent/DE2936121A1/de not_active Withdrawn
-
1980
- 1980-08-26 EP EP19800105053 patent/EP0025165A1/fr not_active Withdrawn
- 1980-09-02 ES ES494707A patent/ES494707A0/es active Granted
- 1980-09-05 AR AR28242280A patent/AR221961A1/es active
- 1980-09-05 BR BR8005664A patent/BR8005664A/pt unknown
- 1980-09-05 JP JP12244180A patent/JPS5645446A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2104475A1 (en) * | 1971-02-01 | 1972-08-17 | Henkel & Cie GmbH, 4000 Düsseldorf | N-(acylaminoalkyl)-n-(3-hydroxy-1-propenyl)-dialkylammonium - salts - useful as textile-softening agents |
| US4039565A (en) * | 1975-06-26 | 1977-08-02 | Ashland Oil, Inc. | Quaternized amidoamines |
| DE2725780A1 (de) * | 1977-06-03 | 1978-12-14 | Miranol Chemical Co | Stickstoffhaltige kondensationsprodukte |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0316701A2 (fr) * | 1987-11-14 | 1989-05-24 | Henkel Kommanditgesellschaft auf Aktien | Sels quaternaires d'amidoammonium, procédé de préparation et utilisation |
| EP0316701A3 (fr) * | 1987-11-14 | 1990-10-17 | Henkel Kommanditgesellschaft auf Aktien | Sels quaternaires d'amidoammonium, procédé de préparation et utilisation |
| EP0643128A1 (fr) * | 1993-09-10 | 1995-03-15 | Kao Corporation | Compositions adoucinants aqueuses, nouveau sel d'ammonium quaternaire et procédé pour la préparation de ce sel |
| US5476597A (en) * | 1993-09-10 | 1995-12-19 | Kao Corporation | Liquid softener composition, novel quaternary ammonium salt, and process for the preparation of said salt |
| US5580481A (en) * | 1993-09-10 | 1996-12-03 | Kao Corporation | Aqueous fabric softener composition, novel quaternary ammonium salt, and process for the preparation of said salt |
| EP0707059A3 (fr) * | 1994-10-14 | 2001-04-18 | Kao Corporation | Composition adoucissante liquide, son utilisation et procédé de préparation d'un sel d'ammonium quaternaire |
| EP1445303A3 (fr) * | 1994-10-14 | 2004-10-20 | Kao Corporation | Composition adoucissante liquide |
Also Published As
| Publication number | Publication date |
|---|---|
| BR8005664A (pt) | 1981-03-17 |
| ES8104986A1 (es) | 1981-05-16 |
| DE2936121A1 (de) | 1981-03-26 |
| JPS5645446A (en) | 1981-04-25 |
| AR221961A1 (es) | 1981-03-31 |
| ES494707A0 (es) | 1981-05-16 |
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