CN1005735B - Textile finishing agent - Google Patents
Textile finishing agent Download PDFInfo
- Publication number
- CN1005735B CN1005735B CN86102993.3A CN86102993A CN1005735B CN 1005735 B CN1005735 B CN 1005735B CN 86102993 A CN86102993 A CN 86102993A CN 1005735 B CN1005735 B CN 1005735B
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- Prior art keywords
- alkyl
- dispersion
- carbon atoms
- amine
- group
- Prior art date
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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
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
含有布伦斯特（Ｂｒｏｎｓｔｅｄｔ）酸，其ＰＫａ值至少是６的含胺类水分散体，其性能稳定。在织物冲洗过程中加入，作织物柔软剂使用。申请号８６１０２９９３．３ Ｉｎｔ．Ｃ１．4 Ｄ０６Ｍ１３／４６ 审定公告日１９８９．１１．０８Aqueous dispersions containing amines containing Bronstedt acid and having a pKa value of at least 6 are stable. Added in fabric washing process, used as fabric softener. Application No. 86102993.3 Int. C1. 4 D06M13/46 Examination and announcement date 1989.11.08
Description
The invention relates to a textile finishing agent. The textile finishing agent is especially suitable for softening fabrics in the cyclic washing process during textile washing, and is beneficial to static control. Its structural features are excellent softness, water dispersibility and storability. It can be stored for a long period of time under the condition of above or below normal temperature.
Textile finishes that soften fabrics during fabric laundering and facilitate static control will be described in detail herein. And find wide commercial use. Typically, the softening agent applied to the fabric during washing comprises a reactive group, essentially a water-insoluble cationic species with two long chain alkyl groups. A common material is dimethyl ammonium chloride with two animal stearates or the substitution of imidazolines with two animal stearates. These prepared substances are generally in the form of aqueous dispersions. In general, the preparation of aqueous dispersions containing more than about 10% of cationic softeners will seriously affect the viscosity of the product and also create shelf life stability problems. Although it has been stated in European patent No.0,000,406 and British patent No.1601360 that certain nonionic additives may be incorporated into the softener in the preparation of high concentrations of softener, the efficiency of such a structure is relatively low in terms of the softening effect per unit weight of active agent. In addition, the viscosity and stability problems of the denser aqueous dispersion products become more pronounced, and the commercial application range of softeners provides 15% -20% active agent content, which is difficult to control.
Concentrated liquid fabric softeners containing at least 10% water miscible organic solvent, typically about 30% to 40% are disclosed in U.S. patent 4454049, 6.12. MacGilp in 1984.
In 1961, 8/luvisi et al, U.S. patent 2995520, disclose acid salts using certain imidazoline derivatives for softening of fiber materials such as cotton and paper. In a treatment tank for textile finishing, containing an acid salt of an imidazoline derivative in a concentration of 0.001% -1%, the product is said to be placed in a low molecular weight aliphatic alcohol for transport to prevent it from freezing.
Another patent more recent than us 2995520 is an imidazoline derivative hydrochloride, which is used to soften fabrics. However, as stated herein, quaternary ammonium salts are more effective than salts of acids such as acyclic tertiary or cyclic amines from the softening point of view of the fabric.
It is therefore an object of the present invention to provide liquid fabric softeners which can be prepared as aqueous dispersions in diluted or concentrated form without the addition of organic solvents. The product of the present invention has excellent stability even in long-term storage at above or below normal temperature, and the composition can further provide excellent softness, antistatic property, fabric rewettability and other characteristics, and can be widely applied to various fabrics.
The present invention provides a stable aqueous dispersion comprising:
(a) The molecular formula I contains di (higher alkyl) cyclic amine, and the amine content is selected to be 1% -40%. And then mixed.
(B) A compound is selected from conventional quaternary ammonium softeners, which contains two higher alkyl groups each containing 8 to 30 carbon atoms.
The invention is based on the formulation of stable aqueous dispersions with certain cyclic amines, even in high concentrations of amine, with a conventional medium di (higher alkyl) quaternary ammonium salt, without the need for large amounts of organic solutions.
(A) Amines:
the amine used in the product of the invention is selected from the group comprising formula I as component (I).
Formula I
Wherein n represents 2,3 or 4, preferably 2, R 1 and R 2 are independently an alkyl or alkenyl group having 8 to 30 carbon atoms, preferably an alkyl group having 11 to 22 carbon atoms, preferably an alkyl group having 15 to 18 carbon atoms, or a mixture of such alkyl groups. The alkyl radicals of such compounds are obtained, for example, from coconut oil, "soft" (not hard) tallow and hard tallow.
Q is CH, CH 2, NL or N. N is preferably used.
X is
In the above formula, T is 0 or NR 5,R5 is H or an alkyl group having 1 to 4 carbon atoms, preferably H. R 4 is a divalent alkylene group having 1 to 3 carbon atoms or (C 2H4 O) m, where m is 1 to 8.X may also be R 4.
The amine content of the composition is 1% -40%, preferably 2% -35%, and most preferably 2% -20%.
Detergent residues may be generated during the washing process. Particularly in the case of the popular washing machines in the united states, there is a tendency to negate the effect of the softener added to the water. It can be seen that the amines of formula I are not readily available for the remainder of the detergent. Such as for example a diocta dimethyl ammonium chloride compound.
(B) Quaternary ammonium salt:
The dispersion contains a conventional di (higher alkyl) quaternary ammonium salt softener as a second component. The higher alkyl groups in the quaternary ammonium salts referred to in this context are alkyl groups having 8 to 30 carbon atoms. Preferably 11 to 20 carbon atoms are used. For example, conventional quaternary ammonium salts include (I) acyclic quaternary ammonium salts of the formula:
R 2 is an acyclic aliphatic hydrocarbon group having 15 to 22 carbon atoms. R 3 is a saturated alkyl or hydroxyalkyl group containing 1 to 4 carbon atoms. R 4 is selected from R 2 or R 3. A is an anion.
(II) diamido quaternary ammonium salt of formula:
R 1 is an acyclic aliphatic hydrocarbon group containing 15 to 21 carbon atoms. R 2 is a divalent alkylene group containing 1 to 3 carbon atoms. R 5 and R 8 are saturated alkyl or hydroxyalkyl groups having 1 to 4 carbon atoms. A - is an anion.
(III) diamide alkoxy quaternary ammonium salt of formula:
( Where n is from 1 to about 5.R 1,R2,R5,A- is as defined above. )
(VI) quaternary ammonium salt imidazoline compounds:
component (I) in the examples is well known.
Dialkyl dimethyl ammonium salts such as ditalloil dimethyl ammonium chloride, ditalloil dimethyl ammonium methyl sulfate, di (hydrogenated tallow) dimethyl ammonium chloride, distearoyl dimethyl ammonium chloride, dibehendyl dimethyl ammonium chloride.
Component (II) in the examples is methyl bis (ethylamide tallow) (2-hydroxyethyl) ammonium methyl sulfate, methyl bis (hydrogenated ethylamide tallow) (2-hydroxyethyl) amine methyl sulfate. R 1 is an acyclic aliphatic hydrocarbon group having 15 to 17 carbon atoms. R 2 is a vinyl group. R 5 is a methyl group. R 8 is a hydroxyalkyl group. A is methyl sulfate anion. These compounds are all available from Sherex chemical company under the trade names Uarisoft (R) 222 and Uarisoft (R) 110, respectively.
In the example (IV), it is:
1-methyl-1-tallow amido-ethyl-2-tallow imidazoline methyl sulfate and 1-methyl-1- (hydrogenated tallow amidoethyl) -methyl sulfate.
The content of the quaternary ammonium salt (b) is preferably 1% -20% of the total weight of the product, and most preferably 2% -20%.
The weight ratio of amine (a) to quaternary ammonium salt (b) is in the range of from 10:1 to 1:10, preferably from 3:1 to 1:3.
Di (higher alkyl) imidazoline compounds, especially 1- (lower alkyl) -1- (higher alkyl) amidoethyl-2- (higher alkyl) imidazolyl compounds, are preferred herein, wherein "lower alkyl" refers to alkyl groups containing 1 to 4 carbon atoms and "higher" refers to alkyl groups containing 11 to 22 carbon atoms.
(C) Brensted (Bronstedt) acid was selected.
The dispersion has a brensted acid PKa value of 6 or less.
The acid content is required to ensure that the pH value of the dispersant after mixing is not more than 5, preferably not more than 4, and the most suitable pH value range is 2.5-4. Typical acid content is 1% -50% by weight of amine, preferably 2% -30% by weight, most preferably 3% -15% by weight.
Suitable classes of acids include inorganic mineral acids, carboxylic acids. In particular low molecular weight carboxylic acids having 1 to 5 carbon atoms, aromatic carboxylic acids such as benzoic acid and alkylsulfonic acid.
Suitable inorganic acids include hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and suitable organic acids include benzoic acid, formic acid, acetic acid, methanesulfonic acid, and ethanesulfonic acid. Phosphoric acid, formic acid and methanesulfonic acid are preferred.
(D) Organic solvents
The preparation of the product does not use any organic solvent. However, organic solvents (such as low molecular weight water-miscible fatty alcohols) do not affect the storage stability, viscosity or softness of the product.
Typically, the amine is derived mostly from solid chemicals, which are dissolved in an organic solvent as a solution. Such as isopropanol organic solvents. No removal of the organic solvent is necessary in any way in the preparation of the present product. In fact, some desirable additive solutions are fully allowable.
In addition, organic solutions are expensive, flammable, even toxic, and difficult to manage as compared to water. The invention is desirably formulated with a small amount of organic solution, i.e., less than 10%, preferably less than 2%.
(E) Selection of organosiloxane components
The product is selected from aqueous emulsion, mainly linear polydialkylsiloxane or alkylaryl siloxane, wherein alkyl can contain 1-5 carbon atoms and can be fully or partially fluorinated. Suitable organosiloxanes are polydimethylsiloxanes having viscosities ranging from 100 to 100,000 centistokes at 25C with a preferred use range of 300 to 6000 centistokes.
The charge characteristics of the organosiloxane ions used have been found to be important, and they play a decisive role in the degree of precipitation and uniformity of distribution of the organosilicon, affecting the properties after finishing of the fabric.
Organic with cations the silicone accelerates precipitation. It has been found that organosiloxanes are advantageous for improving the hand of fabrics and have a predominantly linear chain, preferably polydialkylsiloxanes, with the alkyl groups typically being methyl groups. Organosiloxane polymers the emulsion polymers commonly commercially produced are prepared using strong acids or bases as catalysts in nonionic surfactant emulsifiers or nonionic-anionic mixed surfactant emulsifier systems.
The organosiloxane chosen for use in the present invention is determined by its cationic character. The meaning is as follows.
(A) One of the main chains is two alkyl groups having 1 to 5 carbon atoms or alkylaryl siloxanes having 1 to 5 carbon atoms, preferably with cationic surfactants as emulsion polymer emulsifiers.
(B) Alpha-omega-2 is reacted with two alkyl groups containing 1 to 5 carbon atoms or alkylaryl siloxane polymers containing 1 to 5 carbon atoms through quaternary ammonium reaction
(C) Two alkyl or alkylaryl siloxane polymers containing 1 to 5 carbon atoms of one amino function. The amino group may be used as a substituent or a quaternary ammonium reaction may be carried out, and the degree of substitution (d.s) thereof is kept within a range of 0.001 to 0.1, preferably 0.1 to 0.075.
The viscosity of the organosiloxane is 100 to 100,000 centistokes at 25 ℃.
The content ratio of the siloxane to the amine of the product can be 5:1 to 1:100, and preferably 2:1 to 1:10.
The organosiloxane compositions well disclosed in British patent No.1549180 are suitable for use in the present product.
(F) Nonionic surfactant is selected
The use of nonionic surfactants as softeners has been disclosed. Nonionic surfactants and their amounts are disclosed in U.S. patent 4454049, 6.12. Mac Gilp et al, 1984. Reference is made to the disclosure of which.
Specific nonionic surfactants suitable for use in the present product include glycerolipids (e.g., glycerol monostearate), fatty alcohols (e.g., stearyl alcohol), and alkoxy fatty alcohols. The content of the nonionic surfactant is usually 0.5% -10% of the total weight of the product.
(G) Other optional ingredients
To further increase stability, the viscosity of the products may be further adjusted, and the products may contain a small amount of electrolyte. The most preferred electrolyte is calcium chloride (CaCl 2). It has been found that very small amounts of calcium chloride (example 600 PPm) can reduce the Brookfield viscosity (Brookfield) of high concentration dispersions to below 100 centistokes.
The product may be formulated with other textile softening aids including perfumes, preservatives, bactericides, colorants, dyes, mildewcides, stabilizers, brighteners and opacifiers, in conventional amounts.
Furthermore, to increase some effect of the finished fabric, for example, the amount of perfume product adjuvant (relative to product concentration) may be suitably greater.
Examples I to IV
Preparation of several products:
example 1 example 2 example 3 example 4
DTI1） 20% 10% 8% -
DTDMAC2） - 10% 12% 15%
PDMS3） - - 1% -
Acid 0.2% 4） - - 0.4%5）
Calcium chloride (PPm) 600 800 900 1200
GMS6） - 1% - -
Octadecanol-1%)
Amines 7） 10% 8% 5% 10%
Perfume 0.9% 0.9% 0.9% 0.7%
Water residue and volume residue
1) Ditallow imidazolines
(1-Methyl-1-tallow-amide-ethyl-2-imidazoline chloride)
2) Ditallow dimethyl chloride ammonium salt
3) Polydimethyl siloxane with a viscosity of 500 centistokes
4) Formic acid
5) Methanesulfonic acid
6) Mono-stearin glycerol
7) 1-Tallow amide ethyl-2-tallow imidazole
The two animal fat imidazoline components can be hydrolyzed during processing, but have little effect on the softening effect of the product.
Examples V to VIII
In the following formulation examples, each pH ranges from 2.5 to 5.
Component example V example VI example VII example VIII
DTDMAC1 2.33 7.0 1.26 3.78
PDMS2 1.33 5.0 0.333 1.0
Amines 3 4.33 13 2.34 7.02
Hydrochloric acid 0.268 0.805 0.145 0.435
0.005.17-0.1% Of calcium chloride
Emulsifying agent 4 0.133 0.5 0.033 0.1
Perfume/dye 0.252 0.753 0.251 0.752
Water is matched to is matched to
100% 100% 100% 100%
* The listed component content refers to the percentage of the total weight of the product.
DTDMAC had the same meaning as examples II, III and IV
PDMS refers to polydimethylsiloxane having a viscosity of 5000 centistokes.
3. Amine-1- (2-C 14-C18 -amidoethyl) -2-C 13-C17 -alkyl-4, 5-dihydroimidazoline with CAS number 72623-82-6.
4. The emulsifier "Sapogenat T-100" (commercial number) is triisobutylphenol decagly eolether Hoechst.
Claims (10)
1. A stable aqueous dispersion of a polymer and a polymer, the aqueous dispersion comprises
(A) 1% -40% of an amine mixture selected from di (higher alkyl) cyclic amines of the formula;
(wherein N is 2, 3 or 4, R 1 and R 2 are each C 8-C30 alkyl or alkenyl or a mixture of these groups; Q is CH, CH 2, NH or N, X is 
,
Wherein T is NR 5,R5 is H or C 1-4 alkyl, R 4 is a divalent C 1-C3 alkenyl group or (C 2H4 O) m, m is an integer from 1 to 8, X or R 4;
(b) 1% to 20% of a compound selected from conventional quaternary ammonium softeners having two higher alkyl groups each containing 8 to 30 carbon atoms;
(c) About 1% to about 50% by weight of the amine of a dispersing aid which is a brenstedt (Bronstedt) acid having a pKa value of no greater than 6, the acid being present in an amount to provide a pH of the composition of 5 or less;
(d) 0% to less than 10% of an organic solvent;
(e) The remainder of the composition is water.
2. The dispersion of claim 1, wherein the weight ratio of (a) to (b) is in the range of 3:1 to 1:3.
3. The dispersion of claim 2, comprising from 2% to 35% amine.
4. The dispersion of claim 3 wherein Q is N, N is 2, X is
5. The dispersion of claim 4 wherein the amine is 1- (higher alkyl) amidoethyl-2- (higher alkyl) imidazoline and the higher alkyl represents an alkyl group of 11 to 22 carbon atoms.
6. The dispersion of claim 5 wherein (b) is selected from the group consisting of 1- (lower alkyl) -1- (higher alkyl) amidoethyl-2- (higher alkyl) imidazolinium compounds, the lower alkyl representing an alkyl group of 1 to 4 carbon atoms and the higher alkyl representing an alkyl group of 11 to 22 carbon atoms.
7. A dispersion according to any one of the preceding claims which further comprises an emulsion based on linear di (C 1-C5) alkyl or C 1-C5 alkylaryl siloxanes wherein the alkyl groups may be partially or fully fluorinated or substituted with nitrogen containing cationic groups, the siloxanes having viscosities (25 ℃) of at least 100 centistokes up to 100,000 centistokes and the weight ratio of siloxane to amine in the emulsion being from 5:1 to 1:100.
8. The dispersion of claim 7 wherein the silicone is polydimethylsiloxane.
9. The dispersion of claim 7, further comprising 0.5% to 10% of a nonionic compound selected from the group consisting of glycerides, fatty alcohols, or alkoxylated fatty alcohols.
10. The dispersion of claim 7, wherein the pH of the dispersion is from 2.5 to 4.
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 |
| GB8520803 | 1985-08-20 | ||
| GB858520803A GB8520803D0 (en) | 1985-08-20 | 1985-08-20 | Textile treatment compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN86102993A CN86102993A (en) | 1986-10-01 |
| CN1005735B true CN1005735B (en) | 1989-11-08 |
Family
ID=26289058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN86102993.3A Expired CN1005735B (en) | 1985-03-28 | 1986-03-28 | Textile finishing agent |
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) | FI861341A7 (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) |
Families Citing this family (9)
| 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 |
| GB2188653A (en) * | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
| DE3720331A1 (en) * | 1987-06-19 | 1988-12-29 | Huels Chemische Werke Ag | CONCENTRATED SOFT SOFTENER |
| EP0316996A3 (en) * | 1987-11-18 | 1990-04-04 | The Procter & Gamble Company | Method for preparing textile treatment compositions |
| 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 |
| US5254269A (en) * | 1991-11-26 | 1993-10-19 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric conditioning composition containing an emulsified silicone mixture |
| US5723426A (en) † | 1996-02-29 | 1998-03-03 | Zhen; Yueqian | Liquid laundry detergent compositions containing surfactants and silicone emulsions |
Family Cites Families (5)
| 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 |
| NL7609621A (en) * | 1975-09-04 | 1977-03-08 | Hoechst Ag | TEXTILE TREATMENT AGENT. |
| DE2722079C3 (en) * | 1977-05-16 | 1979-12-06 | Basf Ag, 6700 Ludwigshafen | Liquid softener for textiles |
| DE3263800D1 (en) * | 1981-01-16 | 1985-07-04 | Procter & Gamble | Textile treatment compositions |
| GB8508129D0 (en) * | 1985-03-28 | 1985-05-01 | Procter & Gamble Ltd | Textile treatment composition |
-
1986
- 1986-03-19 DE DE8686200430T patent/DE3679927D1/en not_active Expired - Fee Related
- 1986-03-19 EP EP86200430A patent/EP0197578B1/en not_active Expired - Lifetime
- 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 GB GB08607691A patent/GB2174422B/en not_active Expired
- 1986-03-27 EG EG156/86A patent/EG17723A/en active
- 1986-03-27 MA MA20880A patent/MA20655A1/en unknown
- 1986-03-27 IE IE83186A patent/IE59115B1/en not_active IP Right Cessation
- 1986-03-27 FI FI861341A patent/FI861341A7/en not_active Application Discontinuation
- 1986-03-27 AU AU55353/86A patent/AU591108B2/en not_active Ceased
- 1986-03-28 TR TR157/86A patent/TR23492A/en unknown
- 1986-03-28 CN CN86102993.3A patent/CN1005735B/en not_active Expired
- 1986-03-28 KR KR1019860002330A patent/KR930008698B1/en not_active Expired - Fee Related
- 1986-03-28 JP JP61070640A patent/JPH0768668B2/en not_active Expired - Lifetime
-
1987
- 1987-09-21 MY MYPI87001824A patent/MY100080A/en unknown
-
1992
- 1992-12-24 HK HK1038/92A patent/HK103892A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3679927D1 (en) | 1991-08-01 |
| AU591108B2 (en) | 1989-11-30 |
| GB2174422B (en) | 1989-01-11 |
| EG17723A (en) | 1990-10-30 |
| DK139886A (en) | 1986-09-29 |
| GB2174422A (en) | 1986-11-05 |
| MY100080A (en) | 1989-08-18 |
| JPH0768668B2 (en) | 1995-07-26 |
| EP0197578A3 (en) | 1987-12-02 |
| FI861341A0 (en) | 1986-03-27 |
| MX165248B (en) | 1992-11-04 |
| JPS61275473A (en) | 1986-12-05 |
| IE59115B1 (en) | 1994-01-12 |
| FI861341A7 (en) | 1986-09-29 |
| MA20655A1 (en) | 1986-10-01 |
| EP0197578B1 (en) | 1991-06-26 |
| HK103892A (en) | 1992-12-31 |
| EP0197578A2 (en) | 1986-10-15 |
| TR23492A (en) | 1990-02-01 |
| KR860007415A (en) | 1986-10-13 |
| CA1279447C (en) | 1991-01-29 |
| AU5535386A (en) | 1986-10-02 |
| GB8607691D0 (en) | 1986-04-30 |
| DK139886D0 (en) | 1986-03-25 |
| CN86102993A (en) | 1986-10-01 |
| IE860831L (en) | 1986-09-28 |
| KR930008698B1 (en) | 1993-09-13 |
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