EP0052517B1 - Konzentrierte Textilweichmacherzusammensetzungen - Google Patents
Konzentrierte Textilweichmacherzusammensetzungen Download PDFInfo
- Publication number
- EP0052517B1 EP0052517B1 EP81305438A EP81305438A EP0052517B1 EP 0052517 B1 EP0052517 B1 EP 0052517B1 EP 81305438 A EP81305438 A EP 81305438A EP 81305438 A EP81305438 A EP 81305438A EP 0052517 B1 EP0052517 B1 EP 0052517B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- component
- alkyl
- methylsulfate
- same
- 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.)
- Expired
Links
- 0 CC*N(C)** Chemical compound CC*N(C)** 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
- C11D1/645—Mixtures of compounds all of which are cationic
-
- 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
- C11D3/0015—Softening compositions liquid
-
- 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
Definitions
- This invention relates to fabric softening compositions and, in particular, to compositions in aqueous medium which contain a relatively high proportion of cationic fabric softening ingredients.
- Conventional rinse-added fabric softening compositions contain fabric softening agents which are substantially water-insoluble cationic materials usually having two long alkyl chains. Typical of such materials are distearyl dimethyl ammonium chloride and imidazolinium compounds substituted with two stearyl groups. These materials are normally prepared in the form of an aqueous dispersion or emulsion, and it is generally not possible to prepare such aqueous dispersions with more than about 6% of cationic materials without taking special precautions to ensure acceptable viscosity and stability characteristics. Indeed, with cationic levels in excess of about 8% the problems of physical instability and high viscosity become, in the case of conventional fabric softening products, almost intractable. The formulation of fabric softener compositions with low levels of the active softener ingredients adds substantially to distribution and packaging costs.
- a more concentrated fabric softening composition in addition to shipping and packaging economy, another advantage of a more concentrated fabric softening composition is that it permits the consumer to exercise choice in the type of performance desired, in that the concentrated product can either be used as such or can be diluted to a conventional concentration before use. This opens up the possibility of supplying the concentrated fabric softening composition in a more economically packaged form intended for making up by the consumer into a conventional bottle.
- concentrated fabric softeners which comprise three active softening ingredients, one of which is a highly soluble cationic fabric substantive agent. While such compositions do allow a high concentration of active ingredient, their overall softening performance is less cost effective than is the case with compositions containing predominantly a water-insoluble cationic softener.
- mixtures of cationic softener and paraffinic materials are proposed in a certain ratio which can allow the preparation of concentrated softening compositions when relatively high proportions of paraffinic materials are employed. Paraffins are not essential components of the compositions of the present invention and are preferably absent therefrom.
- NL-A-6706178 relates to viscosity control in fabric softening compositions with up to 12% of cationic softener, and suggests the use of low molecular weight hydrocarbons for this purpose.
- GB-A-1,538,094 discloses a complex softener/disinfectant composition in which a long-chain fatty alcohol used at a relatively low ratio of cationic softener to alcohol is suggested as a solubilization aid.
- EP-A-0013780 discloses concentrated aqueous fabric softener compositions comprising a cationic softener and a viscosity control agent selected from the group consisting of hydrocarbons, fatty acids, fatty acid esters and fatty alcohols.
- EP-A-0018039 discloses concentrated aqueous fabric softening compositions comprising an insoluble cationic softener, a water-soluble nonionic or cationic surfactant and a hydrophobic adjunct selected from C 12 to C 20 paraffins and esters of C 12 to C 24 fatty acids and C, to C s fatty alcohols.
- Water-insoluble fatty nonionic materials are not essential to the compositions herein and are preferably absent therefrom.
- the object of the present invention is to provide highly concentrated aqueous fabric softening compositions, based on cationic softener systems, which do not require substantial quantities of materials other than the cationic softeners to ensure physical stability and acceptable viscosity.
- the invention relates to highly concentrated aqueous liquid fabric softener compositions which comprise a mixture of specific types of cationic softeners and an ionizable salt, wherein the mixture of cationic softeners has an Iodine Value of at least 4.2.
- compositions which contain from 15% to 22.5% by weight of cationic softener ingredients.
- the present invention is directed to concentrated aqueous fabric softener compositions which are pourable at 4.4°C (40°F), the said compositions comprising:
- compositions of the invention are stable and pourable at normally encountered temperatures (4.4°C-37.8°C) and are easily dispersible in water.
- "pourable” means having a viscosity below 5000 mPa's as measured by a Brookfield Synchro-lectric Viscometer with Spindle #4 at 60 rpm.
- the compositions provide excellent fabric softening and antistatic performance in laundry rinse solutions containing from 25 ppm to 90 ppm of the combination of Components A, B and C.
- the mono nitrogen quaternary ammonium salt softener of the compositions herein has the structure: wherein R 1 and R 2 can be the same or different from each other and are selected from C 14 to C 20 alkyl and alkenyl groups and R 3 and R 4 are the same or different from each other and are selected from C 1 to C 3 alkyls, or ⁇ (C n H 2n O) x H wherein n is 2 or 3, x is from 1 to 3, and wherein X - is halide, methylsulfate or ethylsulfate. It is preferred that X- be halide, and the preferred halides are chloride and bromide.
- R, and R 2 be alkyl, i.e., it is preferred that the unsaturation in the cationic active system come from Components B or C, or mixtures thereof.
- Exemplary compounds are dimyristyldimethyl ammonium chloride, dipalmityldiethyl ammonium bromide, distearyldimethyl ammonium chloride, distearyldimethyl ammonium bromide, distearyldiisopropyl ammonium bromide, diarachidyldimethyl ammonium chloride, distearyl-2-hydroxypropylmethyl ammonium chloride, oleylstearyldimethyl ammonium ethylsulfate and distearyl-2-hydroxyethylmethyl ammonium methylsulfate.
- the R 1 and R 2 groups are derived from tallow and the R 3 and R 4 groups are methyl.
- the tallow can be hydrogenated or unhydrogenated. Hydrogenated (i.e., saturated) tallow is preferred, and halides are the preferred anions. Accordingly, preferred mono nitrogen quaternary ammonium salt softener compounds herein are dihydrogenatedtallowdimethyl ammonium chloride and dihydrogenatedtallowdimethyl ammonium bromide. Hydrogenated tallow often has some residual degree of unsaturation such that the lodine Value of hydrogenated ditallowdimethyl ammonium salts can be up to about 5.
- Examplary commercial quaternary ammonium salts which are suitable for use as Component A in the compositions herein are dihydrogenatedtallowdimethyl ammonium chloride sold under the name Adogen (RTM) 442, and ditallowdimethyl ammonium chloride (I.V. about 20-30) sold under the name Adogen (RTM) 470, both from Sherex Chemical Company.
- the quaternary ammonium salts are used in the compositions herein at levels of from 2% to 11%, preferably from 5% to 10%. (All percentages and proportions herein are "by weight” unless specified otherwise).
- the di(2-amidoethyl) methyl quaternary ammonium salt of the invention herein has the structure wherein R 5 and R 6 are the same or different from each other and are selected from C 14 to C 20 alkyl and alkenyl groups, wherein R 7 is selected from H, methyl, ethyl and ⁇ (C n H 2n O) x H wherein n is 2 to 3 and x is from 1 to 5 (preferably 3), and wherein X- is an anion selected from halide, ethylsulfate or methylsulfate.
- R 5 and R 6 are alkyl and R 7 is ⁇ (C n H 2n O) x H.
- These compounds are used at levels of from 2% to 14%, preferably from 5% to about 10%, in the compositions herein. This class of compounds is disclosed in US-A-4,134,840.
- Exemplary compounds are di(2-hydrogenatedtallowamidoethyl) ethoxylated (2 ethoxy groups) methyl ammonium methylsulfate, di(2-hydrogenatedtallowamidoethyl) dimethyl ammonium ethylsulfate, di(2-palmitylamidoethyl) methyl ammonium chloride, di(2-oleylamidoethyl) propoxylated (3 propoxy groups) methyl ammonium bromide, di(2-palmitoleylamidoethyl) dimethyl ammonium ethylsulfate and di(2- stearylamidoethyl) propoxylated (2 propoxy groups) methyl ammonium methylsulfate.
- Exemplary commercial materials suitable for use as Component B herein are di(2-hydrogenated- tallowamidoethyl) ethoxylated methyl ammonium methylsulfate sold under the name Varisoft (RTM) 110, and di(2-tallowamidoethyl) ethyoxylated methyl ammonium methylsulfate (I.V. about 31).sold under the name Varisoft (RTM) 222, both from Sherex Chemical Company.
- Component C which is present at a level of from 2% to 13% (preferably from 3% to 10%) of the compositions of the present invention is a cationic softener selected from three different types of imidazolinium salts. These Component C materials are designated herein as C.(1), C.(2) and C.(3).
- Component C.(1) has the formula: wherein R 8 and R 9 are the same or different from each other and are selected from C 14 to C 20 alkyl and alkenyl groups, wherein X - is halide, ethylsulfate or methylsulfate.
- R 8 and R 9 are a mixture of alkly and alkenyl groups such that Component C.(1) has an I.V. of from 25 to 125, more preferably from 25 to 45.
- Exemplary compounds of this type are: 1-methyl-1-tallowamidoethyl-2-tallowimidazolinium methylsulfate, 1-methyl-1-oleylamidoethyl-2-oleylimidazolinium chloride, 1-methyl-1-palmitoleylamidoethyl-2-palmitoleylimidazolinium ethylsulfate, 1-methyl-1-soyaamidoethyl-2-soyaimidazolinium methylsulfate and 1-methyl-1-hydrogenatedtallowamidoethyl-2-hydrogenatedtallowimidazolinium methylsulfate.
- Exemplary commercial materials are 1-methyl-1-tallowamidoethyl-2-tallowimidazolinium methylsulfate (I.V. about 42) sold under the name Varisoft (RTM) 475, and 1-methyl-1-hydrogenatedtallowamidoethyl-2-hydrogenated- tallowimidazolinium methylsulfate sold under the name Varisoft (RTM) 445, both available from Sherex Chemical Company.
- Component C.(2) has the formula: wherein R 10 and R 11 can be the same or different from each other and are selected from C 14 to C 20 alkyl and alkenyl and X- is halide, methylsulfate or ethylsulfate.
- Exemplary compounds of this type are: 1-ethylene bis(2-stearyl, 1-methyl, imidazolinium methylsulfate), 1-ethylene bis(2-oleyl, 1-methyl, imidazolinium methylsulfate) and 1-ethylene bis(2-tallow, 1-methyl, imidazolinium methylsulfate).
- the tallow derivative, in hydrogenated or unhydrogenated form, is commercially available from Sherex Chemical Company under the name Varisoft (RTM) 6112.
- the unhydrogenated material has an I.V. of about 29.
- Component C.(3) has the formula: wherein R 12 , R 13 , and R 14 are the same or different from each other and are selected from C 14 to C 20 alkyl or alkenyl, wherein X- is halide, methylsulfate or ethylsulfate.
- Exemplary compounds of this type are: 1-methyl-2-stearyl-3[(stearylamidoethyl-stearylamino)-ethylene]imidazolinium ethylsulfate, 1-methyl-2-oleyl-3[(oleylamidoethyl-oleylamino)ethylene]imidazolinium ethylsulfate and 1-methyl-2-tallow-3[tallowamidoethyl-tallowamino)ethylene]imidazolinium ethylsulfate.
- the tallow derivative (I.V. about 32) is sold under the name Varisoft (RTM) 3012 by the Sherex Chemical Company.
- Components C.(1), C.(2) and C.(3) can be used singly or in mixtures with each other.
- Component C in the compositions herein is Component C.(1), wherein R 8 and R 9 are a mixture of alkenyl and alkyl groups such that the compound has an I.V. of from 25 to 125.
- Components A and B will be saturated compounds and the weight ratio of Component C to Components A + B will be at least 0.2:1 and the sum of Components A + B + C will be from 15% to 21%.
- compositions herein are that the cationic active system in the composition has an lodine Value (LV.) of at least 4.2, i.e., a substantial amount of unsaturation must be present.
- LV. lodine Value
- high active compositions which are based on substantially water-insoluble cationic softeners, such as those of the invention, cannot be made without having a substantial amount of unsaturation in the cationic active system.
- the compositions will gel and become unusable at room temperature and below.
- the I.V. is at least 10.5 and is most preferably from 10.5 to 34.
- the unsaturation can come from Component A, B or C, or any combination thereof. I.V.
- the I.V. is defined as the number of decigrams of iodine which will react with one gram of the cationic active system.
- the standard technique for determining I.V. is well known in the art. If one knows the LV. of the individual components which are used in the active system, then the I.V. of the system can simply be calculated by multiplying the I.V. of each component by the percentage of that component in the composition and then dividing by the total percentage of components in the composition.
- the I.V. of the cationic active system is 10 (i.e., 5 x 40 - 20).
- compositions of the invention wherein the total cationic level and the source and amount of unsaturation are varied are illustrated in the following table.
- ionizable salts can be used as Component D in the compositions herein.
- the particular salt should be sufficiently soluble in the compositions to produce a concentration in solution of from 500 to 6000 ppm (preferably 500 to 4000 ppm) and should not adversely interact with the fabric softener compounds.
- suitable salts are the halides of the Group 1A and 2A metals of the Periodic Table of Elements, e.g., sodium chloride, potassium bromide, lithium chloride, calcium chloride and magnesium chloride.
- the ionizable salts provide viscosity control, particularly during the process of mixing the ingredients to make the compositions herein.
- the water used in the compositions herein is preferably distilled or deionized water and is generally present at levels of from 76% to 84%.
- compositions of the invention are those wherein Components A and B are substantially saturated and Component C is unsaturated and is of the type identified herein as C.(1). These preferred compositions can be defined as follows.
- compositions herein Various optional materials such as are ordinarily used in fabric softening compositions can be used in the compositions herein. These include, for example, perfumes at 0.1 % to 1.0%, antimicrobials at 0.01 % to 0.1% and dyes at 0.001% to 0.01%.
- the softening ingredients are normally sold to the formulator in the form of 70% to 90% pastes in which a lower alcohol is a diluent. It has been found that the compositions herein should preferably be substantially free of lower aliphatic alcohols, and that in any event these alcohols should not be present in said compositions at levels in excess of about 3%.
- the softener ingredients are purchased as dispersions in amounts of alcohol which would produce alcohol levels in excess of about 3% in the finished compositions herein, some or all of the alcohol should be removed (e.g., by heat-assisted evaporation) before use in preparing the compositions herein.
- Lower alcohols tend to cause viscosity increase during storage (particularly at higher storage temperatures) and if the alcohol is isopropanol, the odor imparted to the finished product is undesirable.
- freeze-thaw recovery agents are the di-polyethoxy monoalkyl amines of the formula wherein R 19 is an alkyl or alkenyl group of from 14 to 20 carbon atoms and the sum of m + n is from 10 to 25.
- a preferred material is sold under the name Varonic (RTM) T220 by Sherex Chemical Company wherein R 19 is unhydrogenated tallow and the sume of m + n is about 20.
- Freeze-thaw agents are used in the compositions herein at levels of about 1%.
- a particularly preferred method of preparation is as follows. Components A, B and C (and dyes, if used) are heated and blended together to form a melt at 79.4-85°C (175-185°F). This melt is then added gradually to 43.3°C (110°F) water with vigorous agitation. A portion of the ionizable salt is added to the water concurrently with the melted softeners at a rate necessary to keep the aqueous mix fluid and stirrable.
- the remainder of the ionizable salt is added to produce the desired viscosity.
- Optional ingredients such as perfume, etc., are added after the viscosity of the mix has been reduced by the addition of most of the ionizable salt.
- the composition is cooled to room temperature before filling into containers.
- compositions herein have a pH of from 5.5 to 6.5.
- Acids such as hydrochloric, sulfuric or citric or bases such as sodium hydroxide or sodium carbonate can be added, as needed, to the compositions to achieve the desired pH. Normally, only very small amounts of such pH adjusting agents are required.
- This example illustrates the preparation of a 90.7 kg (200 Ib) batch of a composition of the present invention.
- the pre-mix tank was charged with the molten softener actives in the sequence DTDMAC, Varisoft (RTM) 110, Varisoft (RTM) 475.
- the resulting mixture was heated with stirring to 76.7°C (170°F), at which time the dye solution was added. Heating of the mixture then continued until a temperature of 85°C (185°F) was reached.
- the main-mix tank was charged with 66.6 litre (17.6 gal) of deionized water which was then heated to 43.3°C (110°F).
- the agitator was set at 150 rpm and the contents of the pre-mix tank (at 85°C) were pumped into the main-mix tank over a period of 5 minutes. During this 5 minute period the agitator speed was gradually increased to 275 ⁇ 300 rpm as the main-mix thickened. Also, beginning at the point where about one-half of the premix had been added, the CaCI 2 solution was added in portions (see table below) at such a rate as to maintain a stirrable, flowable mixture. As the viscosity decreased the agitator speed was gradually reduced back to 150 rpm. The 120 g of 20% NaOH solution was added about 7 minutes after the start of addition of the active pre-mix to the main-mix tank. (This solution of NaOH serves to adjust the final product pH to 6.0 and also reduces product viscosity:)
- the perfume was added 20 minutes after the start of addition of the active pre-mix to the main-mix tank. Addition of CaCl 2 solution continued until the viscosity of the warm product was 0.14 Pa.s (140 cP). This required a final concentration of 2650 ppm (0.265% CaCl 2 ). Upon cooling to room temperature the resulting 90.7 kg (200 lbs) of product had a viscosity of 0.095 Pa.s (95 cP).
- the lodine Value of the total cationic active system was 10.5.
- This composition exhibits excellent softening and antistatic performance and has excellent physical stability and pourability between 4.4°C (40°F) and 37.8°C (100°F).
- Another formula which exhibits comparable performance, physical stability and pourability is made as above except that the active system consists of 5% dihydrogenatedtallowdimethyl ammonium chloride, 10% di(2-hydrogenatedtallowamido- ethyl)ethoxylated methyl ammonium methylsulfate and 5% 1-methyl-1-tallowamidoethyl-2-tallowimidazo- linium methylsulfate (Varisoft 475). This formula also has an lodine Value of 10.5 for the total cationic active system.
Claims (10)
dadurch gekennzeichnet, daß die Zusammensetzung zusätzlich enthält:
wobei die Gesamtmenge der Komponenten A + B + C 15 Gew.-% bis 22,5 Gew.-% beträgt und wobei an wenigstens einer der Komponenten A, B oder C eine Unsättigung derart vorhanden ist, daß das kationenaktive System, Komponenten A + B + C, einen lodwert von 4,2 bis 40 hat.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT81305438T ATE12947T1 (de) | 1980-11-18 | 1981-11-17 | Konzentrierte textilweichmacherzusammensetzungen. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US20786280A | 1980-11-18 | 1980-11-18 | |
US207862 | 1980-11-18 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0052517A1 EP0052517A1 (de) | 1982-05-26 |
EP0052517B1 true EP0052517B1 (de) | 1985-04-24 |
Family
ID=22772284
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP81305438A Expired EP0052517B1 (de) | 1980-11-18 | 1981-11-17 | Konzentrierte Textilweichmacherzusammensetzungen |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0052517B1 (de) |
JP (1) | JPS57154463A (de) |
AT (1) | ATE12947T1 (de) |
AU (1) | AU544660B2 (de) |
DE (1) | DE3170187D1 (de) |
MX (1) | MX157118A (de) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4439335A (en) * | 1981-11-17 | 1984-03-27 | The Procter & Gamble Company | Concentrated fabric softening compositions |
US4772404A (en) * | 1986-12-24 | 1988-09-20 | Lever Brothers Company | Concentrated liquid fabric softener with whiteners |
US4994193A (en) * | 1988-12-15 | 1991-02-19 | The Procter & Gamble Company | Liquid fabric softener |
AU620785B3 (en) * | 1990-04-26 | 1992-01-09 | D.T.A. Pty Ltd | Transmission sleeve for a down hole hammer |
GB9114540D0 (en) | 1991-07-05 | 1991-08-21 | Unilever Plc | Fabric softening composition |
DE4203489A1 (de) * | 1992-02-07 | 1993-08-12 | Henkel Kgaa | Verfahren zur herstellung niedrigviskoser waessriger esterquat-konzentrate |
US5433869A (en) * | 1992-12-22 | 1995-07-18 | Colgate-Palmolive Co. | Liquid fabric conditioning composition containing amidoamine softening compound |
EP0687291B2 (de) * | 1993-03-01 | 2005-08-24 | The Procter & Gamble Company | Konzentrierte biologisch abbaubare weichspülerzusammensetzungen auf der basis von quartären ammoniumverbindungen |
WO1995016766A1 (en) * | 1993-12-13 | 1995-06-22 | The Procter & Gamble Company | Viscosity stable concentrated liquid fabric softener compositions |
US5474690A (en) * | 1994-11-14 | 1995-12-12 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains |
EP0768369A1 (de) * | 1995-10-11 | 1997-04-16 | The Procter & Gamble Company | Weichspülerzusammensetzungen |
BR9811584A (pt) * | 1997-07-29 | 2000-08-22 | Procter & Gamble | Composição concentrada estável, de preferência transparente, para amaciamento de tecidos contendo amaciante de tecidos de amina |
EP2553068A1 (de) * | 2010-03-26 | 2013-02-06 | The Procter & Gamble Company | Verfahren zur herstellung von weichspülern |
JP7145741B2 (ja) * | 2018-11-30 | 2022-10-03 | 花王株式会社 | 繊維製品の処理方法 |
JP7145787B2 (ja) * | 2019-02-25 | 2022-10-03 | 花王株式会社 | 繊維製品の処理方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3583912A (en) * | 1968-01-29 | 1971-06-08 | Cpc International Inc | Detergent compatible fabric softener |
US3681241A (en) * | 1968-03-04 | 1972-08-01 | Lever Brothers Ltd | Fabric softening |
US3933871A (en) * | 1973-11-12 | 1976-01-20 | Armstrong Chemical Company, Inc. | Fabric softener compound and processes for preparing and using the same |
JPS5338794A (en) * | 1976-09-17 | 1978-04-10 | Kao Corp | Composition for fabric softening agent |
EP0013780B2 (de) * | 1979-01-11 | 1988-08-31 | THE PROCTER & GAMBLE COMPANY | Konzentrierte Textilweichmachungs-Zusammensetzung |
-
1981
- 1981-11-17 AU AU77559/81A patent/AU544660B2/en not_active Expired
- 1981-11-17 MX MX190145A patent/MX157118A/es unknown
- 1981-11-17 AT AT81305438T patent/ATE12947T1/de not_active IP Right Cessation
- 1981-11-17 EP EP81305438A patent/EP0052517B1/de not_active Expired
- 1981-11-17 DE DE8181305438T patent/DE3170187D1/de not_active Expired
- 1981-11-18 JP JP56185146A patent/JPS57154463A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS57154463A (en) | 1982-09-24 |
MX157118A (es) | 1988-10-28 |
AU7755981A (en) | 1982-05-27 |
EP0052517A1 (de) | 1982-05-26 |
ATE12947T1 (de) | 1985-05-15 |
JPH0152507B2 (de) | 1989-11-09 |
DE3170187D1 (en) | 1985-05-30 |
AU544660B2 (en) | 1985-06-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4439335A (en) | Concentrated fabric softening compositions | |
EP0013780B2 (de) | Konzentrierte Textilweichmachungs-Zusammensetzung | |
US4399045A (en) | Concentrated fabric softening compositions | |
AU674014B2 (en) | Fabric conditioning compositions and process for making them | |
EP0052517B1 (de) | Konzentrierte Textilweichmacherzusammensetzungen | |
EP0060003B1 (de) | Textilbehandlungsmittel und deren Zubereitung | |
EP0056695B2 (de) | Textilbehandlungsmittel | |
EP0122141B1 (de) | Weichmacherzusammensetzungen für Textilien | |
US3954634A (en) | Stable, low-viscosity fabric softener | |
US4701268A (en) | Fabric conditioners | |
US4772403A (en) | Fabric softener composition | |
CA1204562A (en) | Method for preparing fabric softening compositions | |
CA1204563A (en) | Liquid fabric-softening composition | |
EP0128231B1 (de) | Stabile konzentrierte wässrige Dispersionen von wasserunlöslichen kationischen Verbindungen und deren Zubereitung | |
EP0394133B1 (de) | Gewebeweichmacherzusammensetzungen | |
CA1232415A (en) | Aqueous concentrated fabric softening composition | |
EP0159919A2 (de) | Konzentrierte wässrige Weichmacherzusammensetzung für Textilien | |
EP1254203B2 (de) | Wäscheweichspülmittel |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): AT BE CH DE FR GB IT NL SE |
|
17P | Request for examination filed |
Effective date: 19821118 |
|
ITF | It: translation for a ep patent filed |
Owner name: ING. C. GREGORJ S.P.A. |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Designated state(s): AT BE CH DE FR GB IT LI NL SE |
|
REF | Corresponds to: |
Ref document number: 12947 Country of ref document: AT Date of ref document: 19850515 Kind code of ref document: T |
|
REF | Corresponds to: |
Ref document number: 3170187 Country of ref document: DE Date of ref document: 19850530 |
|
ET | Fr: translation filed | ||
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed | ||
ITTA | It: last paid annual fee | ||
EAL | Se: european patent in force in sweden |
Ref document number: 81305438.4 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 19951108 Year of fee payment: 15 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19951109 Year of fee payment: 15 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: AT Payment date: 19951113 Year of fee payment: 15 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 19951116 Year of fee payment: 15 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19951128 Year of fee payment: 15 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19951129 Year of fee payment: 15 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19951207 Year of fee payment: 15 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 19960109 Year of fee payment: 15 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Effective date: 19961117 Ref country code: AT Effective date: 19961117 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Effective date: 19961118 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Effective date: 19961130 Ref country code: CH Effective date: 19961130 Ref country code: BE Effective date: 19961130 |
|
BERE | Be: lapsed |
Owner name: THE PROCTER & GAMBLE CY Effective date: 19961130 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19970601 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 19961117 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Effective date: 19970731 |
|
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 19970601 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19970801 |
|
EUG | Se: european patent has lapsed |
Ref document number: 81305438.4 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |