EP0404471A1 - Fabric softening composition - Google Patents
Fabric softening composition Download PDFInfo
- Publication number
- EP0404471A1 EP0404471A1 EP19900306600 EP90306600A EP0404471A1 EP 0404471 A1 EP0404471 A1 EP 0404471A1 EP 19900306600 EP19900306600 EP 19900306600 EP 90306600 A EP90306600 A EP 90306600A EP 0404471 A1 EP0404471 A1 EP 0404471A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- fabric softening
- materials
- weight
- composition according
- 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.)
- Granted
Links
Images
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
-
- 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
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
Abstract
- (i) at least 20% by weight of a fabric softening material; and
- (ii) at least 5% by weight of an organic acid
Description
- The present invention relates to fabric softening compositions suitable for softening fabrics in the rinse step of a fabric laundry process.
- It has been proposed in
DE 33 12 328 (BENCKISER) to prepare fabric softening compositions comprising a combination of fabric softening materials and organic acids, in specific polycarboxylic acids. The compositions as disclosed in this document, however, are of low active levels of up to about 10% by weight. These compositions of low active level are of lamellar structure, wherein the molecules of the fabric softening material form an onion-like configuration comprising concentric bilayers of softening material, between which is trapped an aqueous phase containing the dissolved acid ingredient. By increasing the active level of these formulations, an onset of instability and/or gel formation is observed when the active level exceeds a certain critical level of about 13% by weight of the composition. Therefore up till now it was believed to be impossible to formulate stable fabric softening compositions containing high levels of fabric softening materials in combination with organic acids. - Surprisingly, it has now been found that by further increasing the active level of these compositions, a second class of stable liquid fabric softening compositions can be made. These compositions, unexpectedly are isotropic, they do not comprise a structure of active ingredients. These isotropic compositions are preferred over lamellar compositions in that they are more resistant to temperature fluctuations, and they allow a more flexible use of ingredients.
- Accordingly, the present invention relates to isotropic liquid fabric softening compositions comprising
- (i) at least 20% by weight of a fabric softening material; and
- (ii) at least 5% by weight of an organic acid.
- Preferably the isotropic compositions of the present invention are clear or translucent. Softening compositions which are clear are sometimes particularly appreciated by the consumer, because of their fresh and natural appearance. Clear compositions can be made by ensuring that all ingredients of the composition are completely dissolved in the liquid phase.
- Compositions according to the invention contain at least 20% by weight of a fabric softening material. This material may be selected from cationic, nonionic and amphoteric softening materials, and mixtures thereof.
- Suitable cationic fabric softener materials include water-insoluble cationic materials having a solubility in water at pH 2.5 and 20°C of less than 10g/l. Highly preferred materials are cationic quaternary ammonium salts having two C₁₂₋₁₄ hydrocarbyl chains.
- Well-known species of substantially water-insoluble quaternary ammonium compounds have the formula
- Representative examples of these quaternary softeners include ditallow dimethyl ammonium chloride; ditallow dimethyl ammonium methyl sulfate; dihexadecyl dimethyl ammonium chloride; di(hydrogenated tallow) dimethyl ammonium methyl sulfate; dihexadecyl diethyl ammonium chloride; di(coconut) dimethyl ammonium chloride. Ditallow dimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammonium chloride, di(coconut) dimethyl ammonium methosulfate are preferred.
- Suitable materials also include dialkyl ethoxyl methyl ammonium methosulphate based on soft fatty acid, dialkyl ethoxyl methyl ammonium methosulphate based on hard fatty acid, and a material in which R₃ and R₄ represent methyl, R₁ is C₁₃₋₁₅, R₂ is CH₂CH₂OCOR, where R is stearyl, and X is methosulphate. Materials in which R₂, R₃ and R₄ each represent methyl, R₁ is the group
R₃ and R₄ each represent
-CH₂--C-R, where R is hardened tallow, R₁ is CH₂CH₂OH and X is methosulphate are also suitable. - Preferably cationic softeners are used which have an active melting point (transition from Lb to L state) of less than 25°C, more preferred less than 20°C. Examples of these materials are di-unhardened-tallow dimethyl ammonium chloride and di coconut dimethyl ammonium chloride.
- Other preferred cationic compounds include those materials as disclosed in EP 239,910 (P&G), which is included herein by reference.
- In this specification the expression hydrocarbyl group refers to alkyl or alkenyl groups optionally substituted or interrupted by functional groups such as -OH, -O-, -CONH, -COO-, etc.
- Other preferred materials are the materials of formula
and - Another class of preferred water-insoluble cationic materials are the hydrocarbylimidazolinium salts believed to have the formula:
- Preferred imidazolinium salts include 1-methyl-1-(tallowylamido-) ethyl -2-tallowyl-4,5-dihydro imidazolinium methosulfate and 1-methyl-1-(palmitoylamido) ethyl -2-octadecyl-4,5-dihydroimidazolinium chloride. Other useful imidazolinium materials are 2-heptadecyl-1-methyl-1- (2-stearylamido)ethyl-imidazolinium chloride and 2-lauryl-1-hydroxyethyl-1-oleyl-imidazolinium chloride. Also suitable herein are the imidazolinium fabric softening components of US patent No 4 127 489, incorporated by reference.
- Representative commercially available materials of the above classes are the quaternary ammonium compounds Arquad 2HT (ex AKZO); Noramium M2SH (ex CEKA); Aliquat-2HT (Trade Mark of General Mills Inc), Stepantex Q185 (ex Stepan); Stepantex VP85 (ex Stepan); Stepantex VRH90 (ex Stepan); Synprolam FS (ex ICI) and the imidazolinium compounds Varisoft 475 (Trade Mark of Sherex Company, Columbus Ohio) and Rewoquat W7500 (Trade Mark of REWO).
- The fabric softening materials may also comprise instead of or in addition to cationic fabric softening agents, one or more amines.
- The term "amine" as used herein can refer to
- (i) amines of formula
- (ii) amines of formula
- (iii)imidazolines of formula
- (iv) condensation products formed from the reaction of fatty acids with a polyamine selected from the group consisting of hydroxy alkylalkylenediamines and dialkylenetriamines and mixtures thereof. Suitable materials are disclosed in European Patent Application 199 382 (Procter and Gamble), incorporated herein by reference.
- When the amine is of the formula I above, R₁₅ is a C₆ to C₂₄, hydrocarbyl group, R₁₆ is a C₁ to C₂₄ hydrocarbyl group and R₁₇ is a C₁ to C₁₀ hydrocarbyl group. Suitable amines include those materials from which the quaternary ammonium compounds disclosed above are derived, in which R₁₅ is R₁, R₁₆ is R₂ and R₁₇ is R₃. Preferably, the amine is such that both R₁₅ and R₁₆ are C₆-C₂₀ alkyl with C₁₆-C₁₈ being most preferred and with R₁₇ as C₁₋₃ alkyl, or R₁₅ is an alkyl or alkenyl group with at least 22 carbon atoms and R₁₆ and R₁₂ are C₁₋₃ alkyl. Preferably these amines are protonated with hydrochloric acid, orthophosphoric acid (OPA), C₁₋₅ carboxylic acids or any other similar acids, for use in the fabric conditioning compositions of the invention.
- When the amine is of formula II above, R₁₈ is a C₆ to C₂₄ hydrocarbyl group, R₁₉ is an alkoxylated group of formula -(CH₂CH₂O)yH, where y is within the range from 0 to 6, R₂₀ is an a group of formula -(CH₂CH₂O)zH where z is within the range from 0 to 6 and m is an integer within the range from 0 to 6, and is preferably 13. When m is 0, it is preferred that R₁₈ is a C₁₆ to C₂₂ alkyl and that the sum total of z and y is within the range from 1 to 6, more preferably 1 to 3. When m is 1, it is preferred that R₁₈ is a C₁₆ to C₂₂ alkyl and that the sum total of x and y and z is within the range from 3 to 10.
- Representative commercially available materials of this class include Ethomeen (ex Armour) and Ethoduomeen (ex Armour).
- Preferably the amines of type (ii) or (iii) are also protonated for use in the fabric conditioning compositions of the invention.
- When the amine is of type (iv) given above, a particularly preferred material is
- Alkoxylated fatty amides or amines may also be used as fabric softening materials in compositions of the invention. Suitable materials are for instance disclosed in EP 159 921 (Unilever) and Ep 159 919 (Unilever). The fabric softening material may also comprise instead of or in addition to the above mentioned softening materials one or more fabric substantive amphoteric fabric softening materials. Suitable amphoteric materials form a particulate dispersion at a concentration of less than 1g/l at least one temperature between 0 and 100°C. For the purpose of this invention a fabric substantive amphoteric material is preferably an amphoteric or zwitterionic tertiary or quaternary ammonium compound having either one single very long hydrocarbyl side chain or two long hydrocarbyl chains. From these compounds the use of amphoteric or zwitterionics ammonium compounds having two long hydrocarbyl chains is particularly preferred for many reasons including costs, ease of processing and better stability and performance.
- Amphoteric or zwitterionic ammonium compounds preferably have two long hydrocarbyl chains, each chain having 8-24C-atoms, preferably 10-20C-atoms, most preferred around 16C-atoms.
- Suitable amphoteric fabric substantive materials for use in a fabric treatment composition according to the invention are for instance: ampholytes, hydrocarbyl betaines, hydrocarbylamide betaines, glycinates, propionates and tertiary amine oxides. These materials are described in our co-pending patent application EP 89200545.5.
-
- a) R₂₅ and R₂₆ are C₈₋₂₅ hydrocarbyl chains, R₂₇ is an hydrocarbyl group containing 1-4 carbon atoms or a group -(CH₂,CH₂O)nH, R₂₈, R₂₉, R₃₀ are -(CH₂)-, which can be interrupted with -O-, -CONH-, -COO- etc, R₃₁ is R₂₇, r is 0 or 1, n is an integer from 1-6, X, Y are SO₃, SO²- or COO⁻;
or - b) R₂₅ is a C₁₆₋₅₀ hydrocarbyl chain, R₂₆, R₂₇ are hydrocarbyl groups containing 1-4 carbon atoms or a group -(CH₂CH₂O)nH-, R₂₈, R₂₉, R₃₀ are -(CH₂)n- which can be interrupted by -O-, -COHN-, -COO-, etc, R₃₁ is R₂₇, r is 0 or 1, n is an integer from 1-6, X, Y are SO₃, SO²⁻ or COO-.
- Preferably the amphoteric fabric substantive materials are water soluble and have a solubility in water at pH 2.5 at 20°C of less than 10g/l.
- The HLB of the amphoteric fabric substantive material is preferably less than 10.0.
- Examples of amphoteric materials of the above groups and their method of preparation are given in our co-pending European patent application 89200113.2.
- The compositions may also contain, instead of or in addition to the above mentioned fabric softening agents, non-cationic fabric softening agents, such as nonionic fabric softening agents. Suitable nonionic fabric softening agents, include glycerol esters, such as glycerol mono-stearate, fatty alcohols, such as stearyl alcohol, alkoxylated fatty alcohols C₉-C₂₄ fatty acids such as Dobanol 91-6 (SHELL) and lanolin and derivatives thereof. Suitable materials are disclosed in European Patent Application 88 520 (Unilever PLC/NV case C1325), 122 141 (Unilever PLC/NV case C1363) and 79 746 (Procter and Gamble), the disclosure of which are incorporated herein by reference.
- Preferably compositions of the invention contain at least some cationic fabric softening materials. Preferably at least 50% of the fabric softening material is a cationic fabric softener material.
- The total level of softening material is more than 20% by weight, more preferred more than 30% by weight, most preferred more than 35% by weight of the composition. Generally the total level of softening materials in the composition will be less than 70% by weight, more preferred less than 60% by weight, typically between 40 and 50% by weight.
- Preferably, the compositions of the present invention contain substantially no anionic material, in particular no anionic surface active material. If such materials are present, the weight ratio of the cationic fabric softening agent to the anionic material should preferably be more than 5:1.
- The organic acid material for use in compositions of the present invention may be selected from the group of mono-, di-, tri- or polycarboxylic acids preferably having a total number of carbon atoms of 8 or less, preferably 4 or less.
- Examples of suitable organic acid materials are succinic acid, malic acid, tartaric acid, citric acid, glutaric acid, acetic acid, propionic acid, and lactic acid or mixtures thereof. For obtaining stable products within a wide range of concentrations, the use of lactic acid and acetic acid is preferred. For obtaining products with a particularly interesting appearance and good colour stability it is preferred to use citric acid.
- The level of acid material in the composition (calculated on an anhydrous basis) of the acid material, is at least 5% by weight of the composition more preferred more than 10%. Generally the level of acid material will be less than 50%, more preferred less than 40%, typically between 15% and 35% by weight of the composition.
- The composition can also contain one or more optional ingredients selected from non-aqueous solvents such as C₁-C₄ alkanols and polyhydric alcohols, pH buffering agents, rewetting agents, viscosity modifiers such as electrolytes, for example calcium chloride, antigelling agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, hydrocarbons, antiredeposition agents, enzymes, optical brightening agents, opacifiers, stabilisers such as guar gum and polyethylene glycol, emulsifiers, anti-shrinking agents, lanolin or lanolin like materials, anti-wrinkle agents, fabric crisping agents, anti-spotting agents, soil-release agents, germicides, linear or branched silicones, fungicides, anti-oxidants, anti-corrosion agents, preservatives such as Bronopol (Trade Mark), a commercially available form of 2-bromo-2-nitropropane-1,3-diol, dyes, bleaches and bleach precursors, drape imparting agents, antistatic agents and ironing aids.
- These optional ingredients, if added, are each present at levels up to 5% by weight of the composition, except for the hydrocarbons and the non-aqueous solvents which may be included at levels of up to 30%. The pH of the composition is preferably below the pK of the organic acid, more preferred at least one unit below the pK, typically between 2.0 and 5.0.
- Soil-release agents particularly preferred in the compositions according to the invention are polymers. Suitable polymers include alkyl and hydroxyalkyl cellulose ethers, such as methyl cellulose, and polyvinylpyrrolidone.
- Silicones can be included in the compositions as the ironing aid, rewetting agent or the antifoaming agent. Suitable silicones for use in the compositions according to the invention include predominantly linear polydialkyl or alkylaryl siloxanes in which the alkyl groups contain one to five carbon atoms. The siloxanes can be amido or amino substituted. When the siloxane is amine substituted the amine group may be quaternised.
- Fatty acid materials or other nonionic extenders can also be included in compositions of the present invention. Suitable materials and their amounts are for instance disclosed in EP 13780 (P&G) and
DE 29 43 606 (Unilever). - The balance of the composition is preferably water. Although water-free systems are also within the ambit of the invention, preferably the amount of water in the composition is more than 20% by weight, more preferred more than 25% by weight. Generally the water level will be less than 70%, more preferred less than 60%, most preferred less than 55%, typically between 55% and 25%.
- The viscosity of the product is preferably less than 250 mPas at 106 s-1.
- In use compositions of the present invention may be prediluted or dosed in concentrated form into the rinse-cycle of a fabric washing process. Preferably the material is used at a concentration of between 0.01 and 2g/l, especially between 0.1 and 1g/l.
- The invention will be further illustrated by means of the following examples:
- Fabric softening compositions containing water, tartaric acid (on a dry basis) and a cationic fabric softening material Prapagen 3445 (70% di-unhardened tallow di-
methyl ammonium chloride 20% isopropylalcohol, 10% water) were prepared by mixing under light agitation. - For each composition the structure and appearance were assessed, the results are given in table 1, and graphically expressed in figure 1.
COMPOSITION WATER/PRAPAGEN/TARTARIC (%) RESULT 1. 80/10/10 lamellar/milky 2. 70/10/20 lamellar/milky 3. 60/10/30 lamellar/milky 4. 50/10/40 lamellar/milky 5. 40/10/50 gel 6. 70/20/10 gel 7. 60/20/20 gel 8. 50/20/30 gel 9. 40/20/40 gel 10. 60/30/10 gel 11. 50/30/20 gel 12. 40/30/30 isotropic/clear 13. 30/30/40 phase separation 14. 50/40/10 gel 15. 40/40/20 isotropic/clear 16. 30/40/30 phase separation 17. 20/40/40 phase separation 18. 40/50/10 isotropic/clear 19. 30/50/20 isotropic/clear (some phase separation) - These examples clearly show that lamellar/milky products are formed at low active concentrations; by increasing the active level, unacceptable gelled products are obtained, but surprisingly by further increasing the active levels isotropic/clear compositions can be obtained (
compoisitions - Example 1 was repeated while tartaric acid was replaced by citric acid. The results are expressed in table 1 and figure 2.
COMPOSITION WATER/PRAPAGEN/CITRIC (%) RESULT 20. 80/10/10 lamellar/milky 21. 70/10/20 lamellar/milky 22. 60/10/30 lamellar/milky 23. 50/10/40 gel 24. 70/20/10 gel 25. 60/20/20 gel 26. 50/20/30 gel 27. 40/20/40 gel 28. 60/30/10 gel 29. 50/30/20 gel 30. 40/30/30 isotropic/clear 31. 30/30/40 phase separation 32. 50/40/10 isotropic/clear 33. 40/40/20 isotropic/clear 34. 30/40/30 isotropic/clear 35. 40/50/10 phase separation 36. 30/50/20 phase separation - Again, surprisingly isotropic liquids according to the invention (
Compositions - Example I was repeated while replacing tartaric acid by acetic acid or by lactic acid.
- By using acetic acid isotropic/clear compositions could be formulated even at levels of PRAPAGEN of 50% or more. At lower concentrations a similar behaviour as observed for tartaric acid was observed: lamellar systems at low concentrations, and gelled systems at intermediate concentrations of softening material.
- By using lactic acid, similar results as with acetic acid are observed. This indicates that for stability reasons, especially at high levels of softening materials the use of acetic acid and lactic acid is preferred.
- By replacing tartaric acid by propionic acid isotropic/clear compositions can be formulated even at levels of acid as low as 5%. Typical formulations are:
Formulation % by weight A B C D Arquad 2T 40 40 40 40 Isopropylalcohol 0 5 11 0 Propylene glycol 10 10 10 0 Propionic acid 10 10 5 30 Water balance
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898914054A GB8914054D0 (en) | 1989-06-19 | 1989-06-19 | Fabric softening composition |
GB8914054 | 1989-06-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0404471A1 true EP0404471A1 (en) | 1990-12-27 |
EP0404471B1 EP0404471B1 (en) | 1995-05-10 |
Family
ID=10658680
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90306600A Revoked EP0404471B1 (en) | 1989-06-19 | 1990-06-18 | Fabric softening composition |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0404471B1 (en) |
JP (1) | JP2562843B2 (en) |
KR (1) | KR930008695B1 (en) |
AU (1) | AU623019B2 (en) |
BR (1) | BR9002886A (en) |
CA (1) | CA2018789A1 (en) |
DE (1) | DE69019236T2 (en) |
ES (1) | ES2072981T3 (en) |
GB (1) | GB8914054D0 (en) |
ZA (1) | ZA904745B (en) |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0409502A2 (en) * | 1989-07-17 | 1991-01-23 | Unilever Plc | Fabric softening composition |
WO1994004643A1 (en) * | 1992-08-21 | 1994-03-03 | Colgate-Palmolive Company | Rinse cycle fabric softener |
WO1994005754A1 (en) * | 1992-09-04 | 1994-03-17 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous textile softener dispersions |
US5376286A (en) * | 1992-03-16 | 1994-12-27 | The Procter & Gamble Company | Process for preparing concentrated imidazoline fabric softener compositions |
WO1995004802A1 (en) * | 1993-08-06 | 1995-02-16 | The Procter & Gamble Company | Dryer-activated fabric conditioning and antistatic compositions containing biodegradable compounds having unsaturation |
US5399272A (en) * | 1993-12-17 | 1995-03-21 | The Procter & Gamble Company | Clear or translucent, concentrated biodgradable quaternary ammonium fabric softener compositions |
US5427697A (en) * | 1993-12-17 | 1995-06-27 | The Procter & Gamble Company | Clear or translucent, concentrated 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 |
WO1996014375A1 (en) * | 1994-11-05 | 1996-05-17 | Henkel Kommanditgesellschaft Auf Aktien | Aftertreatment agent for laundry |
US5545340A (en) * | 1993-03-01 | 1996-08-13 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
WO1997003172A1 (en) * | 1995-07-11 | 1997-01-30 | The Procter & Gamble Company | Concentrated, stable fabric softening compositions including chelants |
WO1997009403A1 (en) * | 1995-09-04 | 1997-03-13 | Unilever Plc | Fabric softening composition |
US5670476A (en) * | 1991-04-30 | 1997-09-23 | The Procter & Gamble Company | Fabric softening compositions containing mixtures of substituted imidazoline fabric softener materials and highly ethoxylated curd dispersant |
WO1997034972A1 (en) * | 1996-03-22 | 1997-09-25 | The Procter & Gamble Company | Fabric softening compound/composition |
US5700387A (en) * | 1994-04-07 | 1997-12-23 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening composition |
WO1998008924A2 (en) * | 1996-08-30 | 1998-03-05 | The Procter & Gamble Company | Concentrated premix with reduced flammability for forming fabric softening composition |
US5750491A (en) * | 1993-08-02 | 1998-05-12 | The Procter & Gamble Company | Super concentrate emulsions with fabric actives |
US5773409A (en) * | 1994-04-07 | 1998-06-30 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening composition |
WO1999006509A1 (en) * | 1997-07-29 | 1999-02-11 | The Procter & Gamble Company | Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener |
US6559117B1 (en) | 1993-12-13 | 2003-05-06 | The Procter & Gamble Company | Viscosity stable concentrated liquid fabric softener compositions |
EP1352948A1 (en) * | 1995-07-11 | 2003-10-15 | The Procter & Gamble Company | Concentrated, stable, fabric softening composition |
WO2018007201A1 (en) * | 2016-07-06 | 2018-01-11 | Henkel Ag & Co. Kgaa | Acceleration of the drying of laundry |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE181956T1 (en) * | 1992-05-12 | 1999-07-15 | Procter & Gamble | CONCENTRATED LIQUID FABRIC PLASTENER COMPOSITIONS WITH BIODEGRADABLE TISSUE PLASTICIZERS |
EP1292664A2 (en) * | 2000-06-20 | 2003-03-19 | The Procter & Gamble Company | Multi-phase fabric care composition for delivering multiple fabric care benefits |
KR100880669B1 (en) * | 2008-07-08 | 2009-02-10 | 주식회사 제이미크론 | A manufacturing method for flexibleflat cable |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3954630A (en) * | 1972-09-07 | 1976-05-04 | Colgate-Palmolive Company | Post-wash fabric treating composition and method |
US3984335A (en) * | 1975-01-16 | 1976-10-05 | Basf Wyandotte Corporation | Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom |
US4060505A (en) * | 1975-01-16 | 1977-11-29 | Basf Wyandotte Corporation | Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom |
EP0043622A1 (en) * | 1980-01-07 | 1982-01-13 | THE PROCTER & GAMBLE COMPANY | Fabric softening composition |
DE3312328A1 (en) * | 1983-04-06 | 1984-10-11 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | Rinsing agent for the mechanical washing of laundry |
EP0123999A2 (en) * | 1983-04-22 | 1984-11-07 | Henkel Kommanditgesellschaft auf Aktien | Ready-made textile softener concentrate |
US4832856A (en) * | 1987-03-13 | 1989-05-23 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous fabric softener for the treatment of fabrics: containing alkylamine, hydroxyalkylamine or quaternary ammonium derivative and a carboxylic acid |
WO1989011522A2 (en) * | 1988-05-27 | 1989-11-30 | Henkel Kommanditgesellschaft Auf Aktien | Liquid aqueous laundry-conditioning agent |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI55396C (en) * | 1974-02-11 | 1979-07-10 | Neles Oy | MANOEVRERINGSANORDNING |
US4769159A (en) * | 1986-02-18 | 1988-09-06 | Ecolab Inc. | Institutional softener containing cationic surfactant and organic acid |
GB2188653A (en) * | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
GB8704711D0 (en) * | 1987-02-27 | 1987-04-01 | Unilever Plc | Fabric softening composition |
JPS63295764A (en) * | 1987-05-22 | 1988-12-02 | 花王株式会社 | Softening finish agent |
-
1989
- 1989-06-19 GB GB898914054A patent/GB8914054D0/en active Pending
-
1990
- 1990-06-12 CA CA002018789A patent/CA2018789A1/en not_active Abandoned
- 1990-06-15 AU AU57119/90A patent/AU623019B2/en not_active Ceased
- 1990-06-18 EP EP90306600A patent/EP0404471B1/en not_active Revoked
- 1990-06-18 DE DE69019236T patent/DE69019236T2/en not_active Revoked
- 1990-06-18 ES ES90306600T patent/ES2072981T3/en not_active Expired - Lifetime
- 1990-06-19 KR KR1019900008977A patent/KR930008695B1/en not_active IP Right Cessation
- 1990-06-19 JP JP2161182A patent/JP2562843B2/en not_active Expired - Lifetime
- 1990-06-19 BR BR909002886A patent/BR9002886A/en not_active Application Discontinuation
- 1990-06-19 ZA ZA904745A patent/ZA904745B/en unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3954630A (en) * | 1972-09-07 | 1976-05-04 | Colgate-Palmolive Company | Post-wash fabric treating composition and method |
US3984335A (en) * | 1975-01-16 | 1976-10-05 | Basf Wyandotte Corporation | Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom |
US4060505A (en) * | 1975-01-16 | 1977-11-29 | Basf Wyandotte Corporation | Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom |
EP0043622A1 (en) * | 1980-01-07 | 1982-01-13 | THE PROCTER & GAMBLE COMPANY | Fabric softening composition |
DE3312328A1 (en) * | 1983-04-06 | 1984-10-11 | Joh. A. Benckiser Gmbh, 6700 Ludwigshafen | Rinsing agent for the mechanical washing of laundry |
EP0123999A2 (en) * | 1983-04-22 | 1984-11-07 | Henkel Kommanditgesellschaft auf Aktien | Ready-made textile softener concentrate |
US4832856A (en) * | 1987-03-13 | 1989-05-23 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous fabric softener for the treatment of fabrics: containing alkylamine, hydroxyalkylamine or quaternary ammonium derivative and a carboxylic acid |
WO1989011522A2 (en) * | 1988-05-27 | 1989-11-30 | Henkel Kommanditgesellschaft Auf Aktien | Liquid aqueous laundry-conditioning agent |
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0409502A2 (en) * | 1989-07-17 | 1991-01-23 | Unilever Plc | Fabric softening composition |
EP0409502A3 (en) * | 1989-07-17 | 1991-11-13 | Unilever Plc | Fabric softening composition |
US5670476A (en) * | 1991-04-30 | 1997-09-23 | The Procter & Gamble Company | Fabric softening compositions containing mixtures of substituted imidazoline fabric softener materials and highly ethoxylated curd dispersant |
US5376286A (en) * | 1992-03-16 | 1994-12-27 | The Procter & Gamble Company | Process for preparing concentrated imidazoline fabric softener compositions |
WO1994004643A1 (en) * | 1992-08-21 | 1994-03-03 | Colgate-Palmolive Company | Rinse cycle fabric softener |
WO1994005754A1 (en) * | 1992-09-04 | 1994-03-17 | Henkel Kommanditgesellschaft Auf Aktien | Aqueous textile softener dispersions |
US5545340A (en) * | 1993-03-01 | 1996-08-13 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
US5562849A (en) * | 1993-03-01 | 1996-10-08 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
US5574179A (en) * | 1993-03-01 | 1996-11-12 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compouds containing intermediate iodine value unsaturated fatty acid chains |
US5750491A (en) * | 1993-08-02 | 1998-05-12 | The Procter & Gamble Company | Super concentrate emulsions with fabric actives |
WO1995004802A1 (en) * | 1993-08-06 | 1995-02-16 | The Procter & Gamble Company | Dryer-activated fabric conditioning and antistatic compositions containing biodegradable compounds having unsaturation |
US6559117B1 (en) | 1993-12-13 | 2003-05-06 | The Procter & Gamble Company | Viscosity stable concentrated liquid fabric softener compositions |
US5399272A (en) * | 1993-12-17 | 1995-03-21 | The Procter & Gamble Company | Clear or translucent, concentrated biodgradable quaternary ammonium fabric softener compositions |
US5427697A (en) * | 1993-12-17 | 1995-06-27 | The Procter & Gamble Company | Clear or translucent, concentrated fabric softener compositions |
US5773409A (en) * | 1994-04-07 | 1998-06-30 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening composition |
US5700387A (en) * | 1994-04-07 | 1997-12-23 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric softening composition |
WO1996014375A1 (en) * | 1994-11-05 | 1996-05-17 | Henkel Kommanditgesellschaft Auf Aktien | Aftertreatment agent for laundry |
US5861371A (en) * | 1994-11-05 | 1999-01-19 | Henkel-Ecolab Gmbh & Co. Ohg | Laundry aftertreatment 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 |
WO1997003172A1 (en) * | 1995-07-11 | 1997-01-30 | The Procter & Gamble Company | Concentrated, stable fabric softening compositions including chelants |
EP1352948A1 (en) * | 1995-07-11 | 2003-10-15 | The Procter & Gamble Company | Concentrated, stable, fabric softening composition |
WO1997009403A1 (en) * | 1995-09-04 | 1997-03-13 | Unilever Plc | Fabric softening composition |
WO1997034972A1 (en) * | 1996-03-22 | 1997-09-25 | The Procter & Gamble Company | Fabric softening compound/composition |
WO1998008924A3 (en) * | 1996-08-30 | 1998-05-07 | Procter & Gamble | Concentrated premix with reduced flammability for forming fabric softening composition |
WO1998008924A2 (en) * | 1996-08-30 | 1998-03-05 | The Procter & Gamble Company | Concentrated premix with reduced flammability for forming fabric softening composition |
WO1999006509A1 (en) * | 1997-07-29 | 1999-02-11 | The Procter & Gamble Company | Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener |
US6630441B2 (en) | 1997-07-29 | 2003-10-07 | The Procter & Gamble Company | Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener |
US6998381B2 (en) | 1997-07-29 | 2006-02-14 | The Procter & Gamble Company | Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener |
WO2018007201A1 (en) * | 2016-07-06 | 2018-01-11 | Henkel Ag & Co. Kgaa | Acceleration of the drying of laundry |
KR20190028369A (en) * | 2016-07-06 | 2019-03-18 | 헨켈 아게 운트 코. 카게아아 | Accelerating the drying of laundry |
Also Published As
Publication number | Publication date |
---|---|
BR9002886A (en) | 1991-08-20 |
DE69019236T2 (en) | 1995-10-05 |
AU5711990A (en) | 1990-12-20 |
KR910001155A (en) | 1991-01-30 |
DE69019236D1 (en) | 1995-06-14 |
AU623019B2 (en) | 1992-04-30 |
CA2018789A1 (en) | 1990-12-19 |
ES2072981T3 (en) | 1995-08-01 |
EP0404471B1 (en) | 1995-05-10 |
ZA904745B (en) | 1992-02-26 |
KR930008695B1 (en) | 1993-09-13 |
GB8914054D0 (en) | 1989-08-09 |
JP2562843B2 (en) | 1996-12-11 |
JPH0327180A (en) | 1991-02-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0404471B1 (en) | Fabric softening composition | |
EP0331237B1 (en) | Fabric softening composition | |
EP0199383B1 (en) | Textile treatment compositions | |
EP0326213B1 (en) | A fabric treatment composition and the preparation thereof | |
EP0385749B1 (en) | Fabric softening composition | |
US5403499A (en) | Concentrated fabric conditioning compositions | |
EP0043622B1 (en) | Fabric softening composition | |
EP0361593B1 (en) | Conditioning of fabrics | |
EP0056695A2 (en) | Textile treatment compositions | |
EP0392764B1 (en) | Fabric conditioning article | |
CA1341483C (en) | Fabric conditioning composition | |
EP0415698A2 (en) | Fabric softening composition | |
US4622154A (en) | Aqueous fabric softening composition | |
EP0387064A2 (en) | Fabric conditioning | |
EP0409503B1 (en) | Fabric softening composition | |
EP0417987B1 (en) | Fabric softening | |
EP0159196A2 (en) | Aqueous concentrated fabric softening composition | |
EP0159919A2 (en) | Aqueous concentrated fabric softening composition | |
EP0408279B1 (en) | Fabric softening composition | |
EP0371534A2 (en) | Fabric treatment composition | |
GB2197666A (en) | Method of preparing fabric softening compositions | |
EP0360331B1 (en) | Fabric treatment composition | |
EP0159922A2 (en) | Aqueous fabric softening composition | |
NZ203582A (en) | Fabric softening compositions containing imidazolinium softeners |
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 |
Kind code of ref document: A1 Designated state(s): CH DE ES FR GB IT LI NL SE |
|
17P | Request for examination filed |
Effective date: 19901115 |
|
RAP3 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: UNILEVER N.V. Owner name: UNILEVER PLC |
|
17Q | First examination report despatched |
Effective date: 19930713 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): CH DE ES FR GB IT LI NL SE |
|
REF | Corresponds to: |
Ref document number: 69019236 Country of ref document: DE Date of ref document: 19950614 |
|
ITF | It: translation for a ep patent filed |
Owner name: JACOBACCI & PERANI S.P.A. |
|
ET | Fr: translation filed | ||
REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2072981 Country of ref document: ES Kind code of ref document: T3 |
|
PLBQ | Unpublished change to opponent data |
Free format text: ORIGINAL CODE: EPIDOS OPPO |
|
PLAV | Examination of admissibility of opposition |
Free format text: ORIGINAL CODE: EPIDOS OPEX |
|
PLBI | Opposition filed |
Free format text: ORIGINAL CODE: 0009260 |
|
PLBF | Reply of patent proprietor to notice(s) of opposition |
Free format text: ORIGINAL CODE: EPIDOS OBSO |
|
26 | Opposition filed |
Opponent name: PROCTER & GAMBLE EUROPEAN TECHNICAL CENTER N.V. Effective date: 19960212 |
|
NLR1 | Nl: opposition has been filed with the epo |
Opponent name: PROCTER & GAMBLE EUROPEAN TECHNICAL CENTER N.V. |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19960606 Year of fee payment: 7 |
|
PLBF | Reply of patent proprietor to notice(s) of opposition |
Free format text: ORIGINAL CODE: EPIDOS OBSO |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19970510 Year of fee payment: 8 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 19970520 Year of fee payment: 8 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 19970523 Year of fee payment: 8 Ref country code: DE Payment date: 19970523 Year of fee payment: 8 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: ES Payment date: 19970609 Year of fee payment: 8 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19970619 Year of fee payment: 8 |
|
RDAH | Patent revoked |
Free format text: ORIGINAL CODE: EPIDOS REVO |
|
RDAG | Patent revoked |
Free format text: ORIGINAL CODE: 0009271 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: PATENT REVOKED |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
27W | Patent revoked |
Effective date: 19970630 |
|
GBPR | Gb: patent revoked under art. 102 of the ep convention designating the uk as contracting state |
Free format text: 970630 |
|
NLR2 | Nl: decision of opposition |