EP0197578A2 - Textile treatment compositions - Google Patents
Textile treatment compositions Download PDFInfo
- Publication number
- EP0197578A2 EP0197578A2 EP86200430A EP86200430A EP0197578A2 EP 0197578 A2 EP0197578 A2 EP 0197578A2 EP 86200430 A EP86200430 A EP 86200430A EP 86200430 A EP86200430 A EP 86200430A EP 0197578 A2 EP0197578 A2 EP 0197578A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- dispersion according
- amine
- siloxane
- higher alkyl
- 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
Classifications
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/61—Polyamines polyimines
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
Definitions
- This invention relates to textile treatment compositions. More particularly it relates to textile treatment compositions suitable for use in the rinse cycle of a textile laundering operation to provide fabric softening/static control benefits, the compositions being characterized by excellent softening, water dispersibility and storage properties after prolonged storage at both elevated and sub-normal temperatures.
- rinse-added fabric softening compositions contain, as the active component, substantially water-insoluble cationic materials having two long alkyl chains. Typical of such materials are di-hardened tallow dimethylammonium chloride, and imidazolinium compounds substituted with two tallow groups. These materials are normally prepared in the form of a dispersion in water and it is generally not possible to prepare such aqueous dispersions with more than about 10 % of cationic softener without encountering severe product viscosity and storage-stability problems. Although more concentrated dispersions of softener materials can be prepared as described in European Patent Application No.
- U.S. Patent 4 454 049 issued June 12, 1984 to MacGilp et al discloses concentrated liquid fabric softeners comprising substantial amounts at least . 10%, more typically about 30 -40%, of water miscible organic solvent.
- U.S. Patent 2 995 520 issued August 8, 1961 to Luvisi et al discloses the use of the acid salts of certain imidazoline derivatives for softening of fibrous materials such as cotton and paper.
- the treatment baths used for treating textiles contain from 0.001% to 1% of an acid salt of an imidazoline derivative.
- compositions of the present invention have excellent stability at both elevated and sub-normal temperatures, even under prolonged storage conditions. These compositions further provide excellent softening, antistatic and fabric rewettabifity characteristics across a broad range of fabric types.
- the present invention provides a stable aqueous dispersion comprising:
- compositions of the present invention are based upon the discovery that stable aqueous dispersion can be formulated with certain cyclic amines, even at high amine concentration, and a conventional di(higher alkyl) quartemary ammonium salt, without the use of substantial amounts of organic solvent.
- compositions of the present invention are selected from the group consisting of:
- compositions of the present invention comprise from 1 % to 40% by weight of the amine, preferably from 2% to 35%, and more preferably from 2% to 20%.
- the dispersions herein contain a conventional di(higher alkyl) quaternary ammonium softening agent.
- “higher alkyl” as used in the context of the quarternary ammonium salts herein is meant alkyl groups having from 8 to 30 carbon atoms, preferably from 11 to 22 carbon atoms.
- Examples of such conventional quaternary ammonium salts include (i) acyclic quaternary ammonium salts having the formula: wherein R 2 is an acyclic aliphatic C 15 -C 22 hydrocarbon group.
- R 3 is a C 1 -C 4 saturated alkyl or hydrox- yaikyi group, R 4 is selected from R 2 and R 3 , and A is an anion.
- Component (i) are the well-known dialkyldimethylammoniums salts such as ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, di-(hydrodrogenated tallow) dimethylammonium chloride, distearyldimethylammonium chloride, dibehendyldimethylammonium chloride.
- Component (ii) are methylbis-(tallowamidoethyl) (2-hydroxyethyl) ammonium methylsulfate and methylbis(hydrogenated tal- lowamidoethyl) (2-hydroxyethyl) ammonium methylsulfate wherein R, is an acyclic aliphatic C 15 -C 17 hydrocarbon group, R 2 is an ethylene group, R 5 is a methyl group, R 8 is a hydroxyalkyl group and A is a methylsulfate anion; these materials are available from Sherex Chemical Company under the trade names Varisoft (R) 222 and Varisoft (R) 110, respectively.
- Examples of (iv) are 1-methyl-1-tallowamido-ethyl-2-tallowimidazolinium methylsulfate and 1-methyl-1 -(hydrogenated tallowamidoethyl)-methylsulfate.
- the weight ration amine (a): quaternary ammonium salt (b) is in the range from 10:1 to 1:10, preferably from 3:1 to 1:3.
- di(higher alkyl)imidazolinium compounds are preferred for use herein, in particular the 1-(lower alkyl)-1-(higher alkyl)amidoethyl-2-(higher alkyl)imidazolinium compounds, wherein “lower alkyl” signifies alkyl having from 1 to 4 carbon atoms, and “higher alkyl” signifies alkyl having from 11 to 22 carbon atoms.
- the dispersion may further comprise Bronstedt acids having a pKa value of 6 or less.
- suitable acids include the inorganic mineral acids, carboxylic acids, in particular the low molecular weight (C I- C s ) carboxylic acids, aromatic carboxylic acids, like benzoic acid, and alkylsulfonic acids.
- compositions of the present invention can be formulated without the use of any organic solvent.
- organic solvents - for example, low molecular weight, water mascible aliphatic alcohols, does not harm the storage stability, the viscosity, or the softening performance of the compositions of this invention.
- the amine will be obtained from a supplier of bulk chemicals in solid form of as a solution in an organic solvent, e.g. isopropanol. There is no need, whatsoever, to remove such a solvent in making the compositions of this invention. Indeed, additional solvent may be added, if this is deemed desirable.
- organic solvent e.g. isopropanol
- organic solvents are expensive, and difficult to handle because of their flammability and, sometimes, toxicity. It is therefore desirable to formulate the present compositions with low levels of organic solvent, i.e., less than 10%, preferably less than 2%.
- compositions herein can optionally contain an aqueous emulsion of a predominantly linear polydialkyl or alkyl, aryl siloxane in which the alkyl groups can have from one to five carbon atoms and may be wholly or partially fluorinated.
- Suitable silicones are polydimethyl siloxanes having a viscosity at 25°C in the range from 100 to 100,000 centistokes, preferably in the range from 300 to 6,000 centistokes.
- Silicones having cationic character show an enhanced tendency to deposit. Silicones found to be of value in providing fabric feel benefits have a predominantly linear character and are preferably polydialkyl siloxanes in which the alkyl group is most commonly methyl. Such silicone polymers are frequently manufactured commercially by emulsion polymerisation using a strong acid or strong alkali catalyst in the presence of a nonionic or mixed nonionic-anionic emulsifier system.
- the optional silicone component embraces a silicone of cationic character. which is defined as being one of
- the weight ratio of the siloxane to the amine component of the composition herein typically ranges from 5:1 to 1:100, preferably from 2:1 to 1:10.
- silicone component suitable for use herein are more fully disclosed in British Patent No. 1.549.180.
- compositions optionally contain nonionics as have been disclosed for use in softener compositions.
- nonionics and their usage levels have been disclosed in U.S. Patent 4,454,049, issued June 12,1984 to Mac Gilp et al., the disclosures of which are incorporated herein by reference.
- these compositions can contain relatively small amounts of electrolyte.
- a highly preferred electrolyte is CaCl 2 . It has been found that the Brookfield viscosities of highly concentrated dispersions can be reduced to less than 100 cps, using relatively small amounts of CaCl 2 (e.g., 600 ppm).
- compositions herein can optionally contain other ingredients known to be suitable for use in textile softeners.
- adjuvents include perfumes, preservatives, germicides, colorants, dyes, fungicides, stabilizers, brighteners and opacifiers. These adjuvents, if used, are normally added at their conventional levels
- composition ingredients utilized for a fabric treatment effect e.g., perfumes
- these materials can be added at higher than normal levels, corresponding to the degree of concentration of the product.
- compositions are prepared:
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
- This invention relates to textile treatment compositions. More particularly it relates to textile treatment compositions suitable for use in the rinse cycle of a textile laundering operation to provide fabric softening/static control benefits, the compositions being characterized by excellent softening, water dispersibility and storage properties after prolonged storage at both elevated and sub-normal temperatures.
- Textile treatment compositions suitable for providing fabric softening and static control benefits during laundering are well known in the art and have found widespread commercial application. Conventionally, rinse-added fabric softening compositions contain, as the active component, substantially water-insoluble cationic materials having two long alkyl chains. Typical of such materials are di-hardened tallow dimethylammonium chloride, and imidazolinium compounds substituted with two tallow groups. These materials are normally prepared in the form of a dispersion in water and it is generally not possible to prepare such aqueous dispersions with more than about 10 % of cationic softener without encountering severe product viscosity and storage-stability problems. Although more concentrated dispersions of softener materials can be prepared as described in European Patent Application No. 0 000 406 and British Patent No. 1 601 360 by incorporating certain nonionic adjunct softening materials therein, such compositions tend to be relatively inefficient in terms of softening benefit/unit weight of active; moreover, product viscosity and stability problems become increasingly unmanageable in more concentrated aqueous dispersions and effectively limit the commercial range of applicability to softener active levels in the range from about 15% to about 20%.
- U.S. Patent 4 454 049, issued June 12, 1984 to MacGilp et al discloses concentrated liquid fabric softeners comprising substantial amounts at least . 10%, more typically about 30 -40%, of water miscible organic solvent.
- U.S. Patent 2 995 520, issued August 8, 1961 to Luvisi et al discloses the use of the acid salts of certain imidazoline derivatives for softening of fibrous materials such as cotton and paper. The treatment baths used for treating textiles contain from 0.001% to 1% of an acid salt of an imidazoline derivative. For shipment, it is said to be desirable to place the materials in a low molecular weight aliphatic alcohol to prevent freezing.
- Other patents, more recent than U.S. 2 995 520, also disclose the use of an acid salt of an imidazoline derivative for the softening of fabrics. However, according to the state of the art, quaternary ammonium salts are, in the context of fabric softening, preferred over acid salts of, e.g., acyclic tertiary amines or cyclic amines.
- It is therefore an object of the present invention to provide liquid fabric softening compositions that can be formulated as both diluted and concentrated aqueous dispersions without the need of significant amounts of organic solvents. The compositions of the present invention have excellent stability at both elevated and sub-normal temperatures, even under prolonged storage conditions. These compositions further provide excellent softening, antistatic and fabric rewettabifity characteristics across a broad range of fabric types.
- - The present invention provides a stable aqueous dispersion comprising:
- (a) from 1% to 40% of an amine selected from the group consisting of the di(higher alkyl) cyclic amines of formula I herein; and mixtures thereof; and
- (b) a compound selected from the group of conventional quaternary ammonium softening agents;
- The compositions of the present invention are based upon the discovery that stable aqueous dispersion can be formulated with certain cyclic amines, even at high amine concentration, and a conventional di(higher alkyl) quartemary ammonium salt, without the use of substantial amounts of organic solvent.
- The amines used in the compositions of the present invention are selected from the group consisting of:
- (I) compounds of the formula 1.
- The compositions of the present invention comprise from 1 % to 40% by weight of the amine, preferably from 2% to 35%, and more preferably from 2% to 20%.
- Detergent carryover, as may take place in a laundry process, particularly under conditions as prevail in U.S. washing machines, tends to negatively affect the softening performance of rinse added softeners. It has been found that the amines of formula I are less sensitive to detergent carryover than, e.g. ditallowdimethylammonium chloride. b) Quaternary ammonium salt
- As a second component, the dispersions herein . contain a conventional di(higher alkyl) quaternary ammonium softening agent. By "higher alkyl" as used in the context of the quarternary ammonium salts herein is meant alkyl groups having from 8 to 30 carbon atoms, preferably from 11 to 22 carbon atoms. Examples of such conventional quaternary ammonium salts include (i) acyclic quaternary ammonium salts having the formula:
- (ii) diamido quaternary ammonium salts having the formula:
- (iii) diamido alkoxylated quaternary ammonium salts having the formula:
- (vi) quaternary imidazolinium compounds.
- Examples of Component (i) are the well-known dialkyldimethylammoniums salts such as ditallowdimethylammonium chloride, ditallowdimethylammonium methylsulfate, di-(hydrodrogenated tallow) dimethylammonium chloride, distearyldimethylammonium chloride, dibehendyldimethylammonium chloride.
- Examples of Component (ii) are methylbis-(tallowamidoethyl) (2-hydroxyethyl) ammonium methylsulfate and methylbis(hydrogenated tal- lowamidoethyl) (2-hydroxyethyl) ammonium methylsulfate wherein R, is an acyclic aliphatic C15-C17 hydrocarbon group, R2 is an ethylene group, R5 is a methyl group, R8 is a hydroxyalkyl group and A is a methylsulfate anion; these materials are available from Sherex Chemical Company under the trade names Varisoft (R) 222 and Varisoft (R) 110, respectively.
- Examples of (iv) are 1-methyl-1-tallowamido-ethyl-2-tallowimidazolinium methylsulfate and 1-methyl-1 -(hydrogenated tallowamidoethyl)-methylsulfate.
- The quaternary ammonium salt (b) preferably comprises from 1% to 20%, more preferably 2% to 20% by weight of the composition herein.
- The weight ration amine (a): quaternary ammonium salt (b) is in the range from 10:1 to 1:10, preferably from 3:1 to 1:3.
- The di(higher alkyl)imidazolinium compounds are preferred for use herein, in particular the 1-(lower alkyl)-1-(higher alkyl)amidoethyl-2-(higher alkyl)imidazolinium compounds, wherein "lower alkyl" signifies alkyl having from 1 to 4 carbon atoms, and "higher alkyl" signifies alkyl having from 11 to 22 carbon atoms.
- The dispersion may further comprise Bronstedt acids having a pKa value of 6 or less.
- The amount of acid should be such that the pH of the dispersion, after mixing, is not greater than 5, preferably not greater than 4, and most preferably in the range of from 2.5 -4. Typically, the amount of acid is from 1 % to 50% by weight of the amine, preferably from 2% to 30%, most preferably from 3 to 15%.
- Examples of suitable acids include the inorganic mineral acids, carboxylic acids, in particular the low molecular weight (CI-Cs) carboxylic acids, aromatic carboxylic acids, like benzoic acid, and alkylsulfonic acids.
- Suitable ionorganic acids include HCI, HBr, HIS04, HNO, and H3PO4. Suitable organic acids include benzoic acid, formic, acetic, methylsulfonic and ethylsulfonic acid. Preferred acids are phosphoric, formic and methylsulfonic acid.
- The compositions of the present invention can be formulated without the use of any organic solvent. However, the presence of organic solvents - (for example, low molecular weight, water mascible aliphatic alcohols,) does not harm the storage stability, the viscosity, or the softening performance of the compositions of this invention.
- Typically, the amine will be obtained from a supplier of bulk chemicals in solid form of as a solution in an organic solvent, e.g. isopropanol. There is no need, whatsoever, to remove such a solvent in making the compositions of this invention. Indeed, additional solvent may be added, if this is deemed desirable.
- However, compared to water, organic solvents are expensive, and difficult to handle because of their flammability and, sometimes, toxicity. It is therefore desirable to formulate the present compositions with low levels of organic solvent, i.e., less than 10%, preferably less than 2%.
- The compositions herein can optionally contain an aqueous emulsion of a predominantly linear polydialkyl or alkyl, aryl siloxane in which the alkyl groups can have from one to five carbon atoms and may be wholly or partially fluorinated. Suitable silicones are polydimethyl siloxanes having a viscosity at 25°C in the range from 100 to 100,000 centistokes, preferably in the range from 300 to 6,000 centistokes.
- It has been found that the ionic charge characteristics of the silicone as used in the combination are important in determining both the extent of deposition and the evenness of distribution of the silicone and hence the properties of a fabric treated therewith.
- Silicones having cationic character show an enhanced tendency to deposit. Silicones found to be of value in providing fabric feel benefits have a predominantly linear character and are preferably polydialkyl siloxanes in which the alkyl group is most commonly methyl. Such silicone polymers are frequently manufactured commercially by emulsion polymerisation using a strong acid or strong alkali catalyst in the presence of a nonionic or mixed nonionic-anionic emulsifier system.
- In the present invention, the optional silicone component embraces a silicone of cationic character. which is defined as being one of
- (a) a predominantly linear di C,-CS alkyl or C,-Cs alkyl, aryl siloxane, prepared by emulsion polymerisation using a cationic surfactant as emulsifier;
- (b) an alpha-omega-di quaternised di C1-C5 alkyl or C,-Cs alkyl, aryl siloxane polymer or
- (c) an amino-functional di C,-CS alkyl or alkyl aryl siloxane polymer in which the amino group may be substituted and may be quaternised and in which the degree of substitution - (d.s.) lies in the range 0.001 to 0.1, preferably 01-0.075;
- The weight ratio of the siloxane to the amine component of the composition herein typically ranges from 5:1 to 1:100, preferably from 2:1 to 1:10.
- The silicone component suitable for use herein are more fully disclosed in British Patent No. 1.549.180.
- The compositions optionally contain nonionics as have been disclosed for use in softener compositions. Such nonionics and their usage levels, have been disclosed in U.S. Patent 4,454,049, issued June 12,1984 to Mac Gilp et al., the disclosures of which are incorporated herein by reference.
- Specific examples of nonionics suitable for the compositions herein include glycerol esters (e.g., glycerol monostearate), fatty alcohols (e.g., stearyl alcohol), and alkoxylated fatty alcohols. The nonionics, if used, are typically used at a level in the range of from 0.5 -10% by weight of the composition.
- In order to further improve the stability of the compositions herein, and further adjust their viscosities, these compositions can contain relatively small amounts of electrolyte. A highly preferred electrolyte is CaCl2. It has been found that the Brookfield viscosities of highly concentrated dispersions can be reduced to less than 100 cps, using relatively small amounts of CaCl2 (e.g., 600 ppm).
- The compositions herein can optionally contain other ingredients known to be suitable for use in textile softeners. Such adjuvents include perfumes, preservatives, germicides, colorants, dyes, fungicides, stabilizers, brighteners and opacifiers. These adjuvents, if used, are normally added at their conventional levels
- However, in the case of composition ingredients utilized for a fabric treatment effect, e.g., perfumes, these materials can be added at higher than normal levels, corresponding to the degree of concentration of the product.
-
- 1) ditallow imidazolinium
- (1-methyl-1-tallow-amido-ethyl-2-imidazolinium chloride)
- 2) ditallowdimethylammonium chloride
- 3) polydimethyl siloxane, viscosity 500 centistokes
- 4) formic acid
- 5) methylsulfonic acid
- 6) glycerolmonostearate
- 7) 1-tallowamidoethyI-2-tallowimidazoline
- Some hydrolysis of the ditallow imidazolinium component is observed to take place during processing. This is not found to markedly affect the softening performance of the compositions.
-
- 1. DTDMAC -As in Examples II, III and IV.
- 2. PDMS -Polydimethylsiloxane, viscosity 5000 cs.
- 3. Amine -1-(2-C14-C18-Amidoethyl)-2-C13-C17-alkyl -4.5 dihydroo-imidazoline; CAS number 72623-82-6.
- 4: Emulsifier -As "Sapogenat T 100" (Trade Mark) for triisobutylphenol decaglycolether, Hoechst.
having two higher alkyl groups, each comprising from 8 to 30 carbon atoms.
provided that the viscosity at 25°C of the silicone is from 100 to 100,000 cs.
Claims (9)
provided that the weight ratio of (a):(b) is in the range of from 10:1 to 1:10.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT86200430T ATE64752T1 (en) | 1985-03-28 | 1986-03-19 | MEANS FOR TREATMENT OF TEXTILES. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8508130 | 1985-03-28 | ||
GB858508130A GB8508130D0 (en) | 1985-03-28 | 1985-03-28 | Textile treatment composition |
GB858520803A GB8520803D0 (en) | 1985-08-20 | 1985-08-20 | Textile treatment compositions |
GB8520803 | 1985-08-20 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0197578A2 true EP0197578A2 (en) | 1986-10-15 |
EP0197578A3 EP0197578A3 (en) | 1987-12-02 |
EP0197578B1 EP0197578B1 (en) | 1991-06-26 |
Family
ID=26289058
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86200430A Expired - Lifetime EP0197578B1 (en) | 1985-03-28 | 1986-03-19 | Textile treatment compositions |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP0197578B1 (en) |
JP (1) | JPH0768668B2 (en) |
KR (1) | KR930008698B1 (en) |
CN (1) | CN1005735B (en) |
AU (1) | AU591108B2 (en) |
CA (1) | CA1279447C (en) |
DE (1) | DE3679927D1 (en) |
DK (1) | DK139886A (en) |
EG (1) | EG17723A (en) |
FI (1) | FI861341A (en) |
GB (1) | GB2174422B (en) |
HK (1) | HK103892A (en) |
IE (1) | IE59115B1 (en) |
MA (1) | MA20655A1 (en) |
MX (1) | MX165248B (en) |
MY (1) | MY100080A (en) |
TR (1) | TR23492A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0239910A2 (en) * | 1986-04-02 | 1987-10-07 | The Procter & Gamble Company | Biodegradable fabric softeners |
EP0295386A2 (en) * | 1987-06-19 | 1988-12-21 | Hüls Aktiengesellschaft | Concentrated fabric softener |
EP0316996A2 (en) * | 1987-11-18 | 1989-05-24 | The Procter & Gamble Company | Method for preparing textile treatment compositions |
EP0345842A2 (en) * | 1988-05-27 | 1989-12-13 | The Procter & Gamble Company | Fabric softening compositions containing mixtures of substituted imidazoline esters and quartenized ester-ammonium salts |
EP0544493A1 (en) * | 1991-11-26 | 1993-06-02 | Unilever Plc | Fabric conditioning composition containing an emulsified silicone mixture |
EP0885283B2 (en) † | 1996-02-29 | 2005-02-16 | The Procter & Gamble Company | Liquid laundry detergent compositions containing cationic surfactants and silicone emulsions |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8508129D0 (en) * | 1985-03-28 | 1985-05-01 | Procter & Gamble Ltd | Textile treatment composition |
US4668234A (en) * | 1985-08-15 | 1987-05-26 | E. I. Du Pont De Nemours And Company | Aromatic polyamide fibers and process for stabilizing such fibers with surfactants |
US4661267A (en) * | 1985-10-18 | 1987-04-28 | The Procter & Gamble Company | Fabric softener composition |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2995520A (en) * | 1956-06-11 | 1961-08-08 | Nalco Chemical Co | Treatment of fibrous materials and compositions therefor |
FR2322963A1 (en) * | 1975-09-04 | 1977-04-01 | Hoechst Ag | SOFTENERS FOR TEXTILE MATERIALS |
FR2391312A1 (en) * | 1977-05-16 | 1978-12-15 | Basf Ag | LIQUID AQUEOUS TEXTILE PLASTICIZER |
EP0056695A2 (en) * | 1981-01-16 | 1982-07-28 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8508129D0 (en) * | 1985-03-28 | 1985-05-01 | Procter & Gamble Ltd | Textile treatment composition |
-
1986
- 1986-03-19 EP EP86200430A patent/EP0197578B1/en not_active Expired - Lifetime
- 1986-03-19 DE DE8686200430T patent/DE3679927D1/en not_active Expired - Fee Related
- 1986-03-25 DK DK139886A patent/DK139886A/en not_active Application Discontinuation
- 1986-03-26 MX MX001997A patent/MX165248B/en unknown
- 1986-03-26 CA CA000505176A patent/CA1279447C/en not_active Expired - Lifetime
- 1986-03-27 EG EG156/86A patent/EG17723A/en active
- 1986-03-27 MA MA20880A patent/MA20655A1/en unknown
- 1986-03-27 GB GB08607691A patent/GB2174422B/en not_active Expired
- 1986-03-27 IE IE83186A patent/IE59115B1/en not_active IP Right Cessation
- 1986-03-27 AU AU55353/86A patent/AU591108B2/en not_active Ceased
- 1986-03-27 FI FI861341A patent/FI861341A/en not_active Application Discontinuation
- 1986-03-28 TR TR157/86A patent/TR23492A/en unknown
- 1986-03-28 JP JP61070640A patent/JPH0768668B2/en not_active Expired - Lifetime
- 1986-03-28 CN CN86102993.3A patent/CN1005735B/en not_active Expired
- 1986-03-28 KR KR1019860002330A patent/KR930008698B1/en not_active IP Right Cessation
-
1987
- 1987-09-21 MY MYPI87001824A patent/MY100080A/en unknown
-
1992
- 1992-12-24 HK HK1038/92A patent/HK103892A/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2995520A (en) * | 1956-06-11 | 1961-08-08 | Nalco Chemical Co | Treatment of fibrous materials and compositions therefor |
FR2322963A1 (en) * | 1975-09-04 | 1977-04-01 | Hoechst Ag | SOFTENERS FOR TEXTILE MATERIALS |
FR2391312A1 (en) * | 1977-05-16 | 1978-12-15 | Basf Ag | LIQUID AQUEOUS TEXTILE PLASTICIZER |
EP0056695A2 (en) * | 1981-01-16 | 1982-07-28 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0239910A2 (en) * | 1986-04-02 | 1987-10-07 | The Procter & Gamble Company | Biodegradable fabric softeners |
EP0239910A3 (en) * | 1986-04-02 | 1989-07-05 | The Procter & Gamble Company | Biodegradable fabric softeners |
EP0295386A2 (en) * | 1987-06-19 | 1988-12-21 | Hüls Aktiengesellschaft | Concentrated fabric softener |
EP0295386A3 (en) * | 1987-06-19 | 1990-03-28 | Hüls Aktiengesellschaft | Concentrated fabric softener |
EP0316996A2 (en) * | 1987-11-18 | 1989-05-24 | The Procter & Gamble Company | Method for preparing textile treatment compositions |
EP0316996A3 (en) * | 1987-11-18 | 1990-04-04 | The Procter & Gamble Company | Method for preparing textile treatment compositions |
EP0345842A2 (en) * | 1988-05-27 | 1989-12-13 | The Procter & Gamble Company | Fabric softening compositions containing mixtures of substituted imidazoline esters and quartenized ester-ammonium salts |
EP0345842A3 (en) * | 1988-05-27 | 1990-04-11 | The Procter & Gamble Company | Fabric softening compositions containing mixtures of substituted imidazoline esters and quartenized ester-ammonium salts |
EP0544493A1 (en) * | 1991-11-26 | 1993-06-02 | Unilever Plc | Fabric conditioning composition containing an emulsified silicone mixture |
EP0885283B2 (en) † | 1996-02-29 | 2005-02-16 | The Procter & Gamble Company | Liquid laundry detergent compositions containing cationic surfactants and silicone emulsions |
Also Published As
Publication number | Publication date |
---|---|
MA20655A1 (en) | 1986-10-01 |
JPH0768668B2 (en) | 1995-07-26 |
DK139886D0 (en) | 1986-03-25 |
EG17723A (en) | 1990-10-30 |
CN86102993A (en) | 1986-10-01 |
FI861341A (en) | 1986-09-29 |
HK103892A (en) | 1992-12-31 |
IE59115B1 (en) | 1994-01-12 |
CN1005735B (en) | 1989-11-08 |
JPS61275473A (en) | 1986-12-05 |
CA1279447C (en) | 1991-01-29 |
GB8607691D0 (en) | 1986-04-30 |
GB2174422B (en) | 1989-01-11 |
AU591108B2 (en) | 1989-11-30 |
IE860831L (en) | 1986-09-28 |
TR23492A (en) | 1990-02-01 |
AU5535386A (en) | 1986-10-02 |
MY100080A (en) | 1989-08-18 |
DK139886A (en) | 1986-09-29 |
KR860007415A (en) | 1986-10-13 |
GB2174422A (en) | 1986-11-05 |
KR930008698B1 (en) | 1993-09-13 |
MX165248B (en) | 1992-11-04 |
FI861341A0 (en) | 1986-03-27 |
EP0197578A3 (en) | 1987-12-02 |
EP0197578B1 (en) | 1991-06-26 |
DE3679927D1 (en) | 1991-08-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4806255A (en) | Textile treatment compositions | |
EP0199383B1 (en) | Textile treatment compositions | |
US4661267A (en) | Fabric softener composition | |
US4767547A (en) | Biodegradable fabric softeners | |
US4439330A (en) | Textile treatment compositions | |
EP0060003B1 (en) | Textile treatment compositions and preparation thereof | |
US4157307A (en) | Liquid fabric softener | |
EP0197578B1 (en) | Textile treatment compositions | |
US4622154A (en) | Aqueous fabric softening composition | |
EP0107479B1 (en) | Fabric conditioning composition | |
US4556502A (en) | Liquid fabric-softening composition | |
JP2566177B2 (en) | Textile softening composition and method for producing the same | |
EP0354856A2 (en) | New softening compositions and methods for making and using same | |
JP2757892B2 (en) | Composition for softening liquid textile products | |
JP3283264B2 (en) | Textile softening composition | |
US5484540A (en) | Concentrated fabric softening compositions | |
US5051196A (en) | Softening compositions and methods for making and using same | |
JPH11511802A (en) | Fabric softening composition |
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: A2 Designated state(s): AT BE CH DE FR IT LI LU NL SE |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
RHK1 | Main classification (correction) |
Ipc: C11D 1/645 |
|
AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): AT BE CH DE FR IT LI LU NL SE |
|
17P | Request for examination filed |
Effective date: 19880513 |
|
17Q | First examination report despatched |
Effective date: 19890123 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AT BE CH DE FR IT LI LU NL SE |
|
REF | Corresponds to: |
Ref document number: 64752 Country of ref document: AT Date of ref document: 19910715 Kind code of ref document: T |
|
ITF | It: translation for a ep patent filed |
Owner name: ING. C. GREGORJ S.P.A. |
|
REF | Corresponds to: |
Ref document number: 3679927 Country of ref document: DE Date of ref document: 19910801 |
|
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 | ||
EPTA | Lu: last paid annual fee | ||
EAL | Se: european patent in force in sweden |
Ref document number: 86200430.6 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: AT Payment date: 19950313 Year of fee payment: 10 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 19950315 Year of fee payment: 10 Ref country code: CH Payment date: 19950315 Year of fee payment: 10 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19950322 Year of fee payment: 10 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19950331 Year of fee payment: 10 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: LU Payment date: 19950401 Year of fee payment: 10 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 19950428 Year of fee payment: 10 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19960126 Year of fee payment: 11 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19960319 Ref country code: AT Effective date: 19960319 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Effective date: 19960320 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Effective date: 19960331 Ref country code: CH Effective date: 19960331 Ref country code: BE Effective date: 19960331 |
|
BERE | Be: lapsed |
Owner name: PROCTER & GAMBLE EUROPEAN TECHNICAL CENTER Effective date: 19960331 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19961001 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 19961001 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19961203 |
|
EUG | Se: european patent has lapsed |
Ref document number: 86200430.6 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19971128 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED. Effective date: 20050319 |