AU640152B2 - Fabric softening composition - Google Patents
Fabric softening composition Download PDFInfo
- Publication number
- AU640152B2 AU640152B2 AU59007/90A AU5900790A AU640152B2 AU 640152 B2 AU640152 B2 AU 640152B2 AU 59007/90 A AU59007/90 A AU 59007/90A AU 5900790 A AU5900790 A AU 5900790A AU 640152 B2 AU640152 B2 AU 640152B2
- Authority
- AU
- Australia
- Prior art keywords
- fabric softening
- softening composition
- fatty acid
- materials
- quaternary ammonium
- 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.)
- Ceased
Links
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
-
- 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
- C11D3/2079—Monocarboxylic acids-salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Ut, AW; 0 1
AUSTRALIA
PATENTS ACT 1952 COMPLETE SPECIFICATION Form
(ORIGINAL)
FOR OFFICE USE Short Title: Int. Cl: Application Number: Lodged: Complete Specification-Lodged: Accepted: Lapsed: Published:
I-
-"I
S
S
Priority: Related Art: TO BE COMPLETED BY APPLICANT Name of Applicant: Address of Applicant: C '9 9 UNILEVER PLC UNILEVER HOUSE
BLACKFRIARS
LONDON EC4
ENGLAND
Actual Inventor: Address for Service: GRIFFITH HACK CO., 601 St. Kilda Road, Melbourne, Victoria 3004, Australia.
S#1 Complete Specification for the invention entitled: FABRIC SOFTENING COMPOSITION The following statement is a full description of this invention including the best method of performing it known to me:- 1 C7190 FABRIC SOFTENING COMPOSITION The present invention relates to a fabric softening composition and to a method for its preparation.
0.0. Specifically, the present invention relates to a fabric *0 softening composition for use in the rinse step of a fabric washing process.
It has been proposed in EP 239 910 (PROCTER GAMBLE) to incorporate biodegradable quaternary ammonium compounds in fabric softening compositions. US 3 915 867 (STEPAN) discloses the use of N-methyl,N,N-di(S-C 14 -18 acyloxy
*SS*
ethyl) N- -hydroxy ethyl ammonium methosulphate in softening compositions.
It is an object of the present invention to provide fabric softening compositions which comprise biodegradable quaternary ammonium compounds. It is a second object of S. the invention to provide biodegradable fabric softening compositions which are of acceptable stability. Further 4 objects of the invention are to provide fabric softening compositions which can easily be prepared and which provide surprisingly good softening to fabrics treated therewith.
2 Accordingly, the present invention relates to a fabric softening composition comprising: (i) compound a quaternary ammonium material, which comprises a
R
1
OOCR
2 R1 (CH CH R1 CH2COOR2 1 2 2 a.
a wherein each R i is independently selected from C,_ 4 alkyl, alkenyl or hydroxyalkyl groups; and wherein each R 2 group is independently selected from C 8 2 alkyl or alkenyl groups, and n is an integer from 0 to 5; and (ii) a C,_2 8 fatty acid material or salt thereof.
The compositions of the invention may take a variety of 25 forms such as pastes, liquids, tablets, etc. and also they may be impregnated with substrates, for example for use in tumble dryers. Preferably, compositions of the invention are liquids comprising an aqueous base, wherein the active ingredients are dispersed.
Preferred materials of the above formula and their method of preparation are, for example, described in US 4 137 18P (LEVER BROTHERS). Preferably these materials comprise small amounts of the corresponding monoester as described rr 1 3 in US 4 137 180 for example 1-tallowoxy, 2-hydroxy trimethyl ammonium propane chloride.
Preferably, the level of ester-linked quaternary ammonium compounds is at least 1% by weight cf the composition, more preferably more than 3% by weight of ':he composition; especially interesting are compositions of high active level, e.g. which comprise more than 8% of the ester-linked quaternary ammonium compound. The level of ester-linked quaternary ammonium compounds preferably is o eas
S
So
S
*oo *o* *t 4 C7190 less than 70% by weight of the composition, more preferably less than 50%, typically from 3 to 30% by weight of the composition.
The fatty acid material or salt thereof can be any mono-, di- or tri-carboxylic acid comprising an alkyl or alkenyl chain having from 8 to 28 carbon atoms or salts thereof. Preferred fatty acid materials or their salts may be represented by the formula:
R
1
COOR
2 wherein R 1 is a straight or branched alkyl or alkenyl chain having from 8 to 28 carbon atoms, and wherein R 2 is hydrogen or a cation. Preferred cations are alkali metal ions or alkali earth metal ions; more preferred are sodium, potassium or calcium.
o Preferred is the use of a non-saponified fatty acid material. Especially preferred is the use of free fatty acids having a chain length of from 12 to 18, such as oleic acid, lauric acid, tallow fatty acid etc.
Preferably, the level of fatty acid material is more than 0.1% by weight of the composition, more preferably eri more than especially preferred are concentrated systems comprising more than 0.5% of fatty acid material.
The level of fatty acid material will usually not exceed by weight of the composition, more preferably the level of fatty acid material is less than 30%, typically from 0.5 to 10% by weight of the composition.
The weight ratio of ester-linked quaternary ammonium materials to fatty acid materials is preferably from 10:1 5 C7190 to 1:10, more preferably from 8:1 to 1:1, especially preferably from 7:1 to 3:1.
The compositions of the invention preferably have a pH of more than 2.0. For compositions containing free fatty acids, the pH is preferably less than 5.0 to prevent saponification of the fatty acids. For compositions containing the salts of the fatty acid, preferably the pH is 5.0 or more, more preferably between 5.0 and Compositions of the invention may, in addition to the above described two ingredients, also comprise other active ingredients such as further fabric conditioning materials.
In selecting the optional ingredients it is preferred to use materials which do not substantially affect the biodegradability of the composition. Therefore it is preferred to minimize the level of non-biodegradable or less bio-degradable materials.
Preferably, the compositions of the invention do not comprise large amounts of conventional non-ester-linked quaternary ammonium comounds, more preferably the compositions of the invention are substantially free of these quaternary ammonium compounds.
"o Suitable conditioning materials for inclusion in compositions of the invention comprise nonionic materials.
Suitable nonionic fabric softening agents includ glycerol esters, such as glycerol monostearate, fatty alcohols, such as stearyl alcohol, alkoxylated fatty alcohols, C -C24 fatty acids and lanolin and derivatives thereof.
Suitable materials are disclosed in European Patent Applications 88 520 (Unilever PLC/NV Case C1325), 6 C7190 122 141 (Unilever PLC/NC Case C1363) and 79 746 (Procter Gamble).
Other softening materials which may be incorporated in a composition of the invention are amines, such as, for instance, described in EP 89200545.5, or biodegradable amphoteric softening materials such as, for instance, described in EP 89200113.2.
Preferably, the amount of softening materials other than the above mentioned ester-linked materials and fatty acid materials is relatively low, i.e. the weight ratio of other softener materials to the total of the two essential softener components is preferably less than 2:1, more preferably less than 1:1, most preferably less than 0.5:1.
The composition can also contain one or more optional ingredients selected from non-aqueous solvents such as C -C 4 alkanols and polyhydric alcohols, pH buffering agents such as strong or weak acids, e.g. HC1, H 2
SO
4 to* phosphoric, benzoic or citric acids, rewetting agents, viscosity modifiers such as electrolytes, for example calcium chloride, anti-gelling agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, anti-foaming agents, anti-redeposition agents, enzymes, optical brightening agents, opacifiers, stabilizers such as guar gum and polyethylene glycol, emulsifiers, antishrinking agents, 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, anti-static agents and ironing aids.
-7 C7190 These optional ingredients, if added, are preferably present at levels up to 5% by weight of the composition.
The liquid compositions according to the invention may be prepared by a variety of methods. One suitable method is to form a molten mixture of the ester-linked quaternary ammonium materials and the fatty acid materials, optionally in combination with other softening materials, and adding this premix to water with stirring to form a dispersion and thereafter adding any other optional ingredients.
In use, the fabric conditioning composition of the invention may be added to a large volume of water to form a liquor with which the fabrics to be treated are contacted. Generally, the total concentration of the ester-linked quaternary ammonium compound and the fatty acid compound in this liquor will be between about 30 ppm *oo and 1000 ppm. The weight ratio of the fabrics to the e• liquor will generally be between 1:1 and 1:20.
The invention will be further illustrated by the following Examples.
EXAMPLE I The softening performance of compositions A-C was tested. Composition A is a commercially available fabric conditioner (KUSCHELWEICH) containing 4.5% by weight of dihardened tallow dimethyl ammonium chloride dispersed in water, pH 2.7. Composition B is a 5% by weight dispersion in water of Stepantex VRH 90; the pH of the product is 2.3. Composition C is a dispersion in water of Stepantex VRH 90 and 0.83% of hardened tallow fatty acid; the pH of the product was -8 C7190 loads of desized terry towelling cloths were washed in an AEG LAVAMAT 570 at 500C with water of 24 FH and 100g of a commercially available washing powder (PERSIL AUTOMATIC). Compositions A-C were added to the last rinse cycle of the washing process in the amounts as indicated. The cloths were line-dried and assessed for softness by a trained panel of 9 persons by a round robin test method. A higher softness score indicates a better softness. The following results were obtained: Relative Softness Scores on Terry Towelling softening material dosage 4 7 A 2.0 2.9 3.3 B 1.9 2.9 2.8 C 3.6 3.9 S* In grams of active material (cationic softener plus optionally fatty acid) per rinse.
These results show a clearly better softening performance for composition C compared to compositions A and B. This illustrates the surprisingly good performance O* of compositions comprising a combination of ester-linked quaternary ammonium compounds and fatty acid materials.
EXAMPLE 2 *s*e The softening performance of compositions DEF was tested. Composition D is a commercially available fabric conditioner (COCCOLINO CONCENTRATE). The compositions were prepared by heating the active ingredients until molten and dispersing the molten active into demineralised water at 70°C whilst stirring.
I
9 C7190 Component DTTMAPC THTMAPC DHTDMAC Hardened tallow fatty acid Isopropylalcohol Water 12.00 13.00 12.80 3.20 2.13 2.70 balance 10.29 2.57 2.14 2.27
C.
C
e g.
S
e g.
Oeg* C C S*
C.
S
C
U
S U C. S 1,2-ditallowoxytrimethyl ammonium propane chloride prepared according to US 4 137 180 1-tallowoxy, 2-hydroxy trimethyl ammonium propane chloride prepared according to US 4 137 180 dihardened tallow dimethyl ammonium chloride 40g loads of terry towelling test monitors were washed in a MIELE front loading automatic with a ballast load of terry and polyester cotton to bring the total to The load was washed with 100g of New System Persil Automatic at 60 0 C. 35ml of the compositions D, E or F was added during the final rinse. The monitors were line dried and assessed for softness using a round robin paired comparison protocol by an expert panel. A higher softness score indicates a better softness. The following results were obtained.
Composition Softness Score 0.00 0.23 1.00 10 C7190 A difference between compositions of 0.89 was requried for a 95% significance.
These results show a better softening performance for composition F compared to compositions D and E. This illustrates the surprisingly good performance of compositions comprising a combination of ester-linked quaternary ammonium compounds and fatty acid materials.
EXAMPLE 3 The biodegradability of ester-linked quaternary ammonium materials was compared to that exhibited by more generally used quaternary ammonium materials such as dihardened tallow dimethyl ammonium chloride by using a modified STURM test as described in OECD Paris 1981 Test •c 'Guideline 301B, Decision of the Council C(81)30 Final, Consistent-with the requirements of official Journal of the European Communities No. L251/179 C.5 BIODEGRADATION.
Essentially the test measures the amount of carbon dioxide evolved from a sample undergoing biodegradation as a percentage of the theoretical maximum.
CO evolved **2 DHTDMAC .Stepantex VRH 90 67.1 8.7 (8 determinations) DTTMAPC 78.9 10.1 (10 determinations) dihardened tallow dimethyl ammonium chloride 1,2-ditallowoxy trimethyl ammonium propane chloride These results show that ester-linked quaternary ammonium materials suitable for use in compositions according to the invention are more biodegradable than 11. C7190 quaternary ammonium materials which are -more generally used.
sBee too* v o* *6 4 Sb.
dO*6 *go
Claims (4)
1. A fabric softening composition comprising: a quaternary ammonium material, which comprises a compound R 1 OOCR R 1 N (CH2)n CH R1 CH2COOR2 wherein each R3 is independently selected from C_. 4 alkyl, alkenyl or hydoxyalkyl groups; and wherein each R 2 group 20 is independently selected from C 8 alkyl or alkenyl S.groups, and n is an integer from 0 to 5; and (ii) a C_- 28 fatty acid material or salt thereof. 25 2. A fabric softening composition according to claim S1, being a liquid and comprising an aqueous base.
3. A fabric softening composition according to claim o 1 or claim 2 having a pH of from 2.0 to
4. A fabric softening composition according to any preceding claim, wherein the fatty acid material is not saponified. r,, 13 A fabric softening composition according to any preceding claim, wherein the weight ratio of the quaternary ammonium materials to the fatty acid materials (ii) is from 10:1 to 1:10.
6. A fabric softening composition according to any preceding claim wherein the quaternary ammonium material comprises 1,2-ditallowoxy trimethyl ammonium propane chloride. DATED THIS 28TH DAY OF MAY 1993 UNILEVER PLC By its Patent Attorneys: GRIFFITH HACK CO Fellows Institute of Patent 20 Attorneys of Australia. S S looo /y o o~ooo6 ii\
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898916306A GB8916306D0 (en) | 1989-07-17 | 1989-07-17 | Fabric softening composition |
GB8916306 | 1989-07-17 |
Publications (2)
Publication Number | Publication Date |
---|---|
AU5900790A AU5900790A (en) | 1991-01-17 |
AU640152B2 true AU640152B2 (en) | 1993-08-19 |
Family
ID=10660145
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU59007/90A Ceased AU640152B2 (en) | 1989-07-17 | 1990-07-16 | Fabric softening composition |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0409502B1 (en) |
JP (1) | JP2611036B2 (en) |
AU (1) | AU640152B2 (en) |
BR (1) | BR9003453A (en) |
CA (1) | CA2021322C (en) |
DE (1) | DE69023561T2 (en) |
ES (1) | ES2080119T3 (en) |
GB (1) | GB8916306D0 (en) |
ZA (1) | ZA905607B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU669886B2 (en) * | 1992-04-22 | 1996-06-27 | Unilever Plc | Hair care composition |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0557343A1 (en) * | 1990-11-16 | 1993-09-01 | Akzo Nobel N.V. | Biodegradable fabric softeners |
GB9115255D0 (en) * | 1991-07-15 | 1991-08-28 | Unilever Plc | Fabric softening composition |
GB9114540D0 (en) * | 1991-07-05 | 1991-08-21 | Unilever Plc | Fabric softening composition |
WO1993017085A1 (en) * | 1992-02-20 | 1993-09-02 | Akzo Nobel N.V. | Biodegradable fabric softeners |
WO1993019147A1 (en) * | 1992-03-16 | 1993-09-30 | The Procter & Gamble Company | Fabric softening compositions containing mixtures of softener material and highly ethoxylated curd dispersant |
GB9209170D0 (en) * | 1992-04-28 | 1992-06-10 | Unilever Plc | Rinse conditioner |
ATE181956T1 (en) * | 1992-05-12 | 1999-07-15 | Procter & Gamble | CONCENTRATED LIQUID FABRIC PLASTENER COMPOSITIONS WITH BIODEGRADABLE TISSUE PLASTICIZERS |
WO1993025648A1 (en) * | 1992-06-10 | 1993-12-23 | The Procter & Gamble Company | Stable biodegradable fabric softening compounds and compositions |
GB9218342D0 (en) * | 1992-08-28 | 1992-10-14 | Unilever Plc | Use of fabric softening composition |
US5543067A (en) * | 1992-10-27 | 1996-08-06 | The Procter & Gamble Company | Waterless self-emulsiviable biodegradable chemical softening composition useful in fibrous cellulosic materials |
CN1066188C (en) * | 1993-03-01 | 2001-05-23 | 普罗格特-甘布尔公司 | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
EP0637625A1 (en) * | 1993-08-02 | 1995-02-08 | The Procter & Gamble Company | Super concentrate emulsions with fabric actives |
US5750491A (en) * | 1993-08-02 | 1998-05-12 | The Procter & Gamble Company | Super concentrate emulsions with fabric actives |
MA23554A1 (en) * | 1994-05-18 | 1995-12-31 | Procter & Gamble | SOFTENING COMPOSITIONS FOR BIODEGRADABLE AND CONCENTRATED QUATERNARY AMMONIUM BASED LAUNDRY CONTAINING QUATERNARY AMMONIUM COMPOUNDS WITH SHORT FATTY ACID ALKYL CHAINS |
US5463094A (en) * | 1994-05-23 | 1995-10-31 | Hoechst Celanese Corporation | Solvent free quaternization of tertiary amines with dimethylsulfate |
EP0773982B2 (en) * | 1994-07-26 | 2005-03-23 | The Procter & Gamble Company | Rinse added fabric softener compositions containing antioxidants for sun-fade protection for fabrics |
US5552137A (en) * | 1994-08-05 | 1996-09-03 | Witco Corporation | Biodegradable quaternary hair conditioners |
US5503756A (en) * | 1994-09-20 | 1996-04-02 | The Procter & Gamble Company | Dryer-activated fabric conditioning compositions containing unsaturated fatty acid |
US5460736A (en) * | 1994-10-07 | 1995-10-24 | The Procter & Gamble Company | Fabric softening composition containing chlorine scavengers |
US5505866A (en) * | 1994-10-07 | 1996-04-09 | The Procter & Gamble Company | Solid particulate fabric softener composition containing biodegradable cationic ester fabric softener active and acidic pH modifier |
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 |
GB9517432D0 (en) * | 1995-08-25 | 1995-10-25 | Unilever Plc | Fabric softening composition |
DE69534903T2 (en) * | 1995-08-31 | 2007-01-18 | The Procter & Gamble Company, Cincinnati | Use of allyl alcohol as a bad odor reducing agent |
US6022845A (en) * | 1995-11-03 | 2000-02-08 | The Procter & Gamble Co. | Stable high perfume, low active fabric softener compositions |
GB2301843A (en) * | 1996-05-10 | 1996-12-18 | Unilever Plc | Stable fabric conditioning composition |
US6083899A (en) * | 1996-09-19 | 2000-07-04 | The Procter & Gamble Company | Fabric softeners having increased performance |
GB0002877D0 (en) * | 2000-02-08 | 2000-03-29 | Unilever Plc | Fabric conditioning composition |
SE523426C2 (en) | 2001-08-23 | 2004-04-20 | Akzo Nobel Nv | A nitrogen-containing orthoester-based surfactant, its manufacture and use |
GB0121807D0 (en) | 2001-09-10 | 2001-10-31 | Unilever Plc | Fabric conditioning compositions |
GB0121806D0 (en) | 2001-09-10 | 2001-10-31 | Unilever Plc | A method of reducing the viscosity of fabric conditioning compositions |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0240727A2 (en) * | 1986-03-12 | 1987-10-14 | Henkel Kommanditgesellschaft auf Aktien | Concentrated textile softener |
US4789491A (en) * | 1987-08-07 | 1988-12-06 | The Procter & Gamble Company | Method for preparing biodegradable fabric softening compositions |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1567947A (en) * | 1976-07-02 | 1980-05-21 | Unilever Ltd | Esters of quaternised amino-alcohols for treating fabrics |
FR2440433A1 (en) * | 1978-11-03 | 1980-05-30 | Unilever Nv | FABRIC SOFTENING COMPOSITION AND PROCESS FOR PREPARING THE SAME |
JPS6039791B2 (en) * | 1981-07-10 | 1985-09-07 | ライオン株式会社 | Softener composition |
JPS628427A (en) * | 1985-07-04 | 1987-01-16 | Mitsubishi Electric Corp | Manufacture of glareless cathode-ray tube |
JPS6361426A (en) * | 1986-08-22 | 1988-03-17 | Csk Corp | Data postscripting system for optical recording medium |
DE3818061A1 (en) * | 1988-05-27 | 1989-12-07 | Henkel Kgaa | LIQUID, AQUEOUS LAUNDRY TREATMENT AGENT |
GB8914054D0 (en) * | 1989-06-19 | 1989-08-09 | Unilever Plc | Fabric softening composition |
GB8916307D0 (en) * | 1989-07-17 | 1989-08-31 | Unilever Plc | Fabric softening composition |
-
1989
- 1989-07-17 GB GB898916306A patent/GB8916306D0/en active Pending
-
1990
- 1990-07-13 ES ES90307691T patent/ES2080119T3/en not_active Expired - Lifetime
- 1990-07-13 EP EP90307691A patent/EP0409502B1/en not_active Expired - Lifetime
- 1990-07-13 DE DE69023561T patent/DE69023561T2/en not_active Expired - Fee Related
- 1990-07-16 AU AU59007/90A patent/AU640152B2/en not_active Ceased
- 1990-07-17 BR BR909003453A patent/BR9003453A/en not_active IP Right Cessation
- 1990-07-17 JP JP2189298A patent/JP2611036B2/en not_active Expired - Lifetime
- 1990-07-17 ZA ZA905607A patent/ZA905607B/en unknown
- 1990-07-17 CA CA002021322A patent/CA2021322C/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0240727A2 (en) * | 1986-03-12 | 1987-10-14 | Henkel Kommanditgesellschaft auf Aktien | Concentrated textile softener |
US4789491A (en) * | 1987-08-07 | 1988-12-06 | The Procter & Gamble Company | Method for preparing biodegradable fabric softening compositions |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU669886B2 (en) * | 1992-04-22 | 1996-06-27 | Unilever Plc | Hair care composition |
Also Published As
Publication number | Publication date |
---|---|
DE69023561T2 (en) | 1996-04-18 |
JPH03113077A (en) | 1991-05-14 |
JP2611036B2 (en) | 1997-05-21 |
AU5900790A (en) | 1991-01-17 |
EP0409502B1 (en) | 1995-11-15 |
EP0409502A3 (en) | 1991-11-13 |
ZA905607B (en) | 1992-03-25 |
ES2080119T3 (en) | 1996-02-01 |
BR9003453A (en) | 1991-08-27 |
DE69023561D1 (en) | 1995-12-21 |
GB8916306D0 (en) | 1989-08-31 |
CA2021322A1 (en) | 1991-01-18 |
CA2021322C (en) | 2000-10-31 |
EP0409502A2 (en) | 1991-01-23 |
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Legal Events
Date | Code | Title | Description |
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MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |