CA1152707A - Fabric softener - Google Patents
Fabric softenerInfo
- Publication number
- CA1152707A CA1152707A CA000355973A CA355973A CA1152707A CA 1152707 A CA1152707 A CA 1152707A CA 000355973 A CA000355973 A CA 000355973A CA 355973 A CA355973 A CA 355973A CA 1152707 A CA1152707 A CA 1152707A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- weight
- methyl
- alkyl
- fabric softener
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/645—Mixtures of compounds all of which are cationic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
-
- 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
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
Abstract
FABRIC SOFTENER
Abstract of the Disclosure:
1) Fabric softeners in the form of an aqueous solution or dispersion which contain from 3 to 15 weight % of one or more compounds of the formulae I to IV
I
II
III
, IV
in which R1 is alkyl or alkenyl having from 6 to 18, preferably 8 to 14, carbon atoms, R2 is alkyl having from 1 to 4 carbon atoms, preferably methyl, R3 is methyl or hydrogen, x and y are hydrogen or methyl with the proviso that x and y are not simultaneously methyl, n is a number of from 1 to 20, preferably 3 to 10, m is a number of from 1 to 15, preferably 1, and A is an - 1a -anion;from 3 to 15 weight % of a compound of the formula V
V
Abstract of the Disclosure:
1) Fabric softeners in the form of an aqueous solution or dispersion which contain from 3 to 15 weight % of one or more compounds of the formulae I to IV
I
II
III
, IV
in which R1 is alkyl or alkenyl having from 6 to 18, preferably 8 to 14, carbon atoms, R2 is alkyl having from 1 to 4 carbon atoms, preferably methyl, R3 is methyl or hydrogen, x and y are hydrogen or methyl with the proviso that x and y are not simultaneously methyl, n is a number of from 1 to 20, preferably 3 to 10, m is a number of from 1 to 15, preferably 1, and A is an - 1a -anion;from 3 to 15 weight % of a compound of the formula V
V
Description
~527~7
- 2 - H0~ 79/~ 179 It is known that textiles whicll have been washed, es-pecially in an automatic washer~ and particularly thoqe made from cellulose fibers, are in a disagreeable har-dened state after drying. This undesirably hardened feel can be overcome by treating the textiles aftcr washing in a rinsing bath with cationic subqtance~ which contain at least two long-chain aliphatic radicals in the mole-cule. Especially the dialkyl-dimethylammonium salts dis-persible in water have proved in the practice to be suitable for this application. However, on overdosage, these product~ have the disadvantage of making the treated fabric too hydrophobic, thus retarding rewetting. More-over, it is very difficult to combine ~uch long-chain dialkyl-dimethylammonium salts with short-chain dialkyl-quats, for example in order to prepare fabric softener formulations having a bactericidal activity. Furthermore, these dispersions have the disadvantage of a milky, turbid appearance, while nowadays fabric softeners in the form of transparent aqueou~ solutions are in demand.
It has now been found that these disadvantages are overcome by combining the quaternary ammonium compounds used as fabric softeners with a fatty acid alkylol-amidoxethylate. Subject of the invention are therefore fabric softeners in the form of an agueous solution or dispersion which contain from 3 to 15, preferably 3 to 8, weight % of one or more compounds of the formulae I to IV
R1 / R2 ~
/ ~ _ j A
Rl R2 ~ N - CH2 ~ A II
R2 CH2-CH2 ~H C R1 .~
~11 527U7
It has now been found that these disadvantages are overcome by combining the quaternary ammonium compounds used as fabric softeners with a fatty acid alkylol-amidoxethylate. Subject of the invention are therefore fabric softeners in the form of an agueous solution or dispersion which contain from 3 to 15, preferably 3 to 8, weight % of one or more compounds of the formulae I to IV
R1 / R2 ~
/ ~ _ j A
Rl R2 ~ N - CH2 ~ A II
R2 CH2-CH2 ~H C R1 .~
~11 527U7
- 3 - HOE 79/F 179 X y ' `, R1(0-CH-C~-)n \ ~ / 2 \ A III
R1(0-CH-CH-)n / R2 x y 1 \ ~ / 2 10 R ~ (CH2-CH-O)H l A IV
in which R1 is alkyl or alkenyl having from 6 to 18, pre-ferably 8 to 14l carbon atom3, R~ i~ alkyl having from 1 to 4 carbon atoms, preferably methyl, R3 is methyl or hydrogen, x and ~ are hydrogen or methyl with the provi30 that x and y are not simultaneously methyl, n i~ a number of from 1 to 20, preferably 3 to 10, m is a number of from 1 to 15, preferably 1, and A i~ an anion such as Cl(-), Br( ), CH30S03 or (CH3)20 3 weight ~o of a compound of the formula V
R4-CONH-CH-CH-O-(CH-CHO)nH V
X y x y in which R4 i~ alXyl having from 8 to 30, preferably 10 to 18, carbon atoms, and n, x, and y are as defined above;
and optionally from 3 to 5 weight % of a bactericidal quaternary ammonium compound, and further usual auxi-liaries and additives.
This combination of the compounds I to V impart~ an pleasant and soft feel to any textile material, es-pecially those made from natural or regenerated cellu-lose, wool, cellulose acetate, cellulose triacetate, polyamide, polyacrylonitrile, polyesters or polypropylene.
Especially advantageous is its use for the after-treat-ment of terry fabrics and underwear. The fabric softeners of the invention are prepared by simply mixing or dis-., .
~L5~7;~7
R1(0-CH-CH-)n / R2 x y 1 \ ~ / 2 10 R ~ (CH2-CH-O)H l A IV
in which R1 is alkyl or alkenyl having from 6 to 18, pre-ferably 8 to 14l carbon atom3, R~ i~ alkyl having from 1 to 4 carbon atoms, preferably methyl, R3 is methyl or hydrogen, x and ~ are hydrogen or methyl with the provi30 that x and y are not simultaneously methyl, n i~ a number of from 1 to 20, preferably 3 to 10, m is a number of from 1 to 15, preferably 1, and A i~ an anion such as Cl(-), Br( ), CH30S03 or (CH3)20 3 weight ~o of a compound of the formula V
R4-CONH-CH-CH-O-(CH-CHO)nH V
X y x y in which R4 i~ alXyl having from 8 to 30, preferably 10 to 18, carbon atoms, and n, x, and y are as defined above;
and optionally from 3 to 5 weight % of a bactericidal quaternary ammonium compound, and further usual auxi-liaries and additives.
This combination of the compounds I to V impart~ an pleasant and soft feel to any textile material, es-pecially those made from natural or regenerated cellu-lose, wool, cellulose acetate, cellulose triacetate, polyamide, polyacrylonitrile, polyesters or polypropylene.
Especially advantageous is its use for the after-treat-ment of terry fabrics and underwear. The fabric softeners of the invention are prepared by simply mixing or dis-., .
~L5~7;~7
- 4 - ~IOE 79~F t7~
per~ing the individual components in water. They may con-tain one compound each of the formula I to IV, or a mix-ture of two or more compounds of these formulae within the ranges a~ indicated. In the case of a mixture of two or more compo~nd~ of the formulae I to IV, the mixing ratio thereof with one another is not at all critical and may have any value.
In addition to the compounds of the formulae I to V, the softeners of the invention may contain from 3 to 5 weight % of a bactericidal compound, especially selected from the group of compounds of the following formulae VI to VIII
R~ ~ ] A~ VI
r~ - N~ - C~12_~-Cl ] A~3 VII
\ ] VIII
in which R1, R2 and A are as defined above and R7 is an aliphatic radical having from 6 to 12, preferably 10, carbon atoms.
The fabric softeners of the invention may also con-tain further substances and auxiliaries which are either mixed already with the concentrate of the fabric softener or are ad~ed ~epa~ate~y~ to the ready-to-use , dilute composition. These are substances or auxiliaries which are conventionally used in softening compositions; they -~ 1 527~7
per~ing the individual components in water. They may con-tain one compound each of the formula I to IV, or a mix-ture of two or more compounds of these formulae within the ranges a~ indicated. In the case of a mixture of two or more compo~nd~ of the formulae I to IV, the mixing ratio thereof with one another is not at all critical and may have any value.
In addition to the compounds of the formulae I to V, the softeners of the invention may contain from 3 to 5 weight % of a bactericidal compound, especially selected from the group of compounds of the following formulae VI to VIII
R~ ~ ] A~ VI
r~ - N~ - C~12_~-Cl ] A~3 VII
\ ] VIII
in which R1, R2 and A are as defined above and R7 is an aliphatic radical having from 6 to 12, preferably 10, carbon atoms.
The fabric softeners of the invention may also con-tain further substances and auxiliaries which are either mixed already with the concentrate of the fabric softener or are ad~ed ~epa~ate~y~ to the ready-to-use , dilute composition. These are substances or auxiliaries which are conventionally used in softening compositions; they -~ 1 527~7
- 5 - HOE 79/F 179 include, for example, cationic and nonionic surface-active substances, electrolytes, neutralizing a~ents, organic complexing agent~, optical brighteners and ~olu-bilizers, as well as dye~tuffs and perfumes. Additives of this kind serve, for example, to further influence the feel of the fabric or other properties of the textile goods to be treated, or the ~djustment of the visco~ity or pH or further promote the stability of the solution~
at low temperatures.
The fabric softeners are applied as usual, that i8 they are added to the last rinsing water after the washing operations are complete. The textiles so treated are subsequently dried.
The above fabric softeners are absolutely trans-parent and have the advantage of providing a considerablyimproved rewettability of cotton as compared to commer-cial products. It is furthermore surprising to ob~erve that even those compounds of the formulae I to IV have ~ good softening effect in combination with a compound of the formula V which contain more than 50 % of alkyl groups containing only 12 carbon atoms, although it is known that such compounds per se have only a moderate ~oftening effect as compared to di-tallow fatty alkyl-dimethylammonium chloride. The fatty acid alkylolamidox-ethylates per se have no softening activity.
The following example~ describe some softeners ofthe invention; percentages being by weight in all cases.
All these softeners are prepared by simply mixing aqueous solutions of the individual components with agitation 30 at low temperature.
E X A M P L E _1:
Di-coconut alkyl-dimethylammonium chloride 6.7 %
Fatty acid alkylolamide + 5 EO5.0 %
Perfumes, dyestuff, water remainder up to 100.0 %
35 E X A M P L E 2:
Di-coconut alkyl-dimethylammonium chloride 5.0 %
Fatty acid alkylolamide ~ 5 EO5.0 %
.
1~L52707
at low temperatures.
The fabric softeners are applied as usual, that i8 they are added to the last rinsing water after the washing operations are complete. The textiles so treated are subsequently dried.
The above fabric softeners are absolutely trans-parent and have the advantage of providing a considerablyimproved rewettability of cotton as compared to commer-cial products. It is furthermore surprising to ob~erve that even those compounds of the formulae I to IV have ~ good softening effect in combination with a compound of the formula V which contain more than 50 % of alkyl groups containing only 12 carbon atoms, although it is known that such compounds per se have only a moderate ~oftening effect as compared to di-tallow fatty alkyl-dimethylammonium chloride. The fatty acid alkylolamidox-ethylates per se have no softening activity.
The following example~ describe some softeners ofthe invention; percentages being by weight in all cases.
All these softeners are prepared by simply mixing aqueous solutions of the individual components with agitation 30 at low temperature.
E X A M P L E _1:
Di-coconut alkyl-dimethylammonium chloride 6.7 %
Fatty acid alkylolamide + 5 EO5.0 %
Perfumes, dyestuff, water remainder up to 100.0 %
35 E X A M P L E 2:
Di-coconut alkyl-dimethylammonium chloride 5.0 %
Fatty acid alkylolamide ~ 5 EO5.0 %
.
1~L52707
- 6 - I:~OE 79/F 179 Di-tallow fatty allcyl-dimethylamlllonium chloride 1. 7 %
Perfumes~ dyestuff, w~ter remainder to 100.0 %
E X A M P L E ~:
Di-coconut alkyl-imidazolinium derivative 6.7 %
5 Fatty acid alkylolamide + 5 E0 5.0 %
Perfumes~ dyestuff, water remainder to ~00.0 %
E X A M P L E 4:
Di-coconut alkyl-dimethylammonium chloride 6.7 %
Fatty acid alkylolamide ~ 5 E0 5.0 %
10 Coconut alkyl-dimethylbenzylammonium chloride 4.0 %
Perfumes, dyestuff, water remainder to 100.0 %
.
Di-coconut alkyl-dimethylammonium chloride 6.7 Fatty Acid alkylolamide + 5 E0 5.0 ~
15 Didecyl-dimethylammonium chloride 4.0 %
Perfumes, dyestuff, water remainder to 100.0 %
E X A M P L E 6:
Di-coconut alkyl-dimethylammonium chloride 6.7 %
~atty acid alkylolamide + 5 E0 5.0 %
Coconut alkyl-2l4-dichlorobenzyl-dimethylammonium chloride 4.0 X
Perfumes, dyestuff, water remainder to lO0.0 %
E X A M P L E 7: (Comparative formulation) Di-tallow fatty alkyl-dimethylammonium chloride 8.7 %
Perfume~, dyestuff, water remainder to 100.0 %
These fabric ~ofteners were tested according to German Indu4trial Standard DIN 53924 with respect to their influence on the rewettability. Smooth cotton and polyester fabrics (satin blouse cloth) were treated with the mixture of the invention. A commercial softener ~E~ample 7) wa~ used for a compari~on. According to this test method, the results listed in the following Tables were obtained for the mixtures of Examples 1 to 7. The rise of non-finished fabrics is defined as being 100 %.
~S27(~7
Perfumes~ dyestuff, w~ter remainder to 100.0 %
E X A M P L E ~:
Di-coconut alkyl-imidazolinium derivative 6.7 %
5 Fatty acid alkylolamide + 5 E0 5.0 %
Perfumes~ dyestuff, water remainder to ~00.0 %
E X A M P L E 4:
Di-coconut alkyl-dimethylammonium chloride 6.7 %
Fatty acid alkylolamide ~ 5 E0 5.0 %
10 Coconut alkyl-dimethylbenzylammonium chloride 4.0 %
Perfumes, dyestuff, water remainder to 100.0 %
.
Di-coconut alkyl-dimethylammonium chloride 6.7 Fatty Acid alkylolamide + 5 E0 5.0 ~
15 Didecyl-dimethylammonium chloride 4.0 %
Perfumes, dyestuff, water remainder to 100.0 %
E X A M P L E 6:
Di-coconut alkyl-dimethylammonium chloride 6.7 %
~atty acid alkylolamide + 5 E0 5.0 %
Coconut alkyl-2l4-dichlorobenzyl-dimethylammonium chloride 4.0 X
Perfumes, dyestuff, water remainder to lO0.0 %
E X A M P L E 7: (Comparative formulation) Di-tallow fatty alkyl-dimethylammonium chloride 8.7 %
Perfume~, dyestuff, water remainder to 100.0 %
These fabric ~ofteners were tested according to German Indu4trial Standard DIN 53924 with respect to their influence on the rewettability. Smooth cotton and polyester fabrics (satin blouse cloth) were treated with the mixture of the invention. A commercial softener ~E~ample 7) wa~ used for a compari~on. According to this test method, the results listed in the following Tables were obtained for the mixtures of Examples 1 to 7. The rise of non-finished fabrics is defined as being 100 %.
~S27(~7
- 7 - HOE 79/F 179 Table 1 cotto~fabric, smooth 1 g FS/kg cloth 2 g FS/k~ Cloth Example 1 85 % 80 %
" 2 76 ~ 69 %
" 3 83 % 73 %
" ~ 82 % 72 %
" 5 ~0 % 71 %
" 6 82 ~ 71 %
" 7 (comparative formulation) 60 % 55 %
Blank test~esult 100 %
(cotton fabric, not finished) Table 2 100 % polyester satin fabric (blouse cloth~
;
1 g FS/k~ cloth 2 g FS/kg cloth Blank test result 100 %
(non~finished fabric) Example 7 . 90 % 100 %
" 1 190 % 190 %
20 " 2 180 % 176 %
" 3 186 % 178 %
4 184 % 173 ~
~i 5 181 % 170 %
- 6 183 % 174 %
The results of the two Tables prove that the specimens provided with the mixtures of the invention have an improved absorption.
" 2 76 ~ 69 %
" 3 83 % 73 %
" ~ 82 % 72 %
" 5 ~0 % 71 %
" 6 82 ~ 71 %
" 7 (comparative formulation) 60 % 55 %
Blank test~esult 100 %
(cotton fabric, not finished) Table 2 100 % polyester satin fabric (blouse cloth~
;
1 g FS/k~ cloth 2 g FS/kg cloth Blank test result 100 %
(non~finished fabric) Example 7 . 90 % 100 %
" 1 190 % 190 %
20 " 2 180 % 176 %
" 3 186 % 178 %
4 184 % 173 ~
~i 5 181 % 170 %
- 6 183 % 174 %
The results of the two Tables prove that the specimens provided with the mixtures of the invention have an improved absorption.
Claims (6)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A fabric softener in the form of an aqueous solution or dispersion which contains (a) from 3 to 15 weight % of one or more compounds of the formulae I to IV
A- I
A- II
A- III
A-IV
in which R1 is an alkyl or alkenyl group having from 6 to 18 carbon atoms, R2 is an alkyl group having from 1 to 4 carbon atoms, R3 is methyl or hydrogen, x and y are hydrogen or methyl with the proviso that x and y are not simultaneously methyl, n is a number of from 1 to 20, m is a number of from 1 to 15, and A is an anion;
(b) from 3 to 15 weight % of a compound of the formula V
V
in which R4 is an alkyl group having from 8 to 30 carbon atoms, and n, x, and y are as defined above; and (c) optionally from 3 to 5 weight % of a bactericidal quaternary ammonium compound.
A- I
A- II
A- III
A-IV
in which R1 is an alkyl or alkenyl group having from 6 to 18 carbon atoms, R2 is an alkyl group having from 1 to 4 carbon atoms, R3 is methyl or hydrogen, x and y are hydrogen or methyl with the proviso that x and y are not simultaneously methyl, n is a number of from 1 to 20, m is a number of from 1 to 15, and A is an anion;
(b) from 3 to 15 weight % of a compound of the formula V
V
in which R4 is an alkyl group having from 8 to 30 carbon atoms, and n, x, and y are as defined above; and (c) optionally from 3 to 5 weight % of a bactericidal quaternary ammonium compound.
2. A fabric softener as claimed in claim 1, which contains from 3 to 8 weight % of one or more compounds of the formulae I to IV and from 3 to 8 weight % of a compound of the formula V.
3. A fabric softener as claimed in claim 1 or 2, wherein R1 is an alkyl or alkenyl group having from 8 to 14 carbon atoms, R2 is methyl and R4 is an alkyl group having 10 to 18 carbon atoms.
4. A fabric softener as claimed in claim 1 or 2, wherein n is a number of from 3 to 10 and m is 1.
5. A fabric softener as claimed in claim 1 or 2, which contains as the bactericidal quaternary ammonium compound a compound selected from the group of compounds of the following formulae VI
to VIII
A.theta. (VI) A.theta.
(VII) (VIII) in which R1, R2 and A are as defined in claim 1, and R7 is an aliphatic radical having from 6 to 12 carbon atoms.
to VIII
A.theta. (VI) A.theta.
(VII) (VIII) in which R1, R2 and A are as defined in claim 1, and R7 is an aliphatic radical having from 6 to 12 carbon atoms.
6. A fabric softener as claimed in claim 1 or 2, wherein A is Cl, Br, CH3OSO3 or (CH3)2OPO3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2928141.2 | 1979-07-12 | ||
| DE19792928141 DE2928141A1 (en) | 1979-07-12 | 1979-07-12 | SOFT SOFTENER |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1152707A true CA1152707A (en) | 1983-08-30 |
Family
ID=6075520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000355973A Expired CA1152707A (en) | 1979-07-12 | 1980-07-11 | Fabric softener |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0022555B1 (en) |
| JP (1) | JPS5615472A (en) |
| AR (1) | AR224163A1 (en) |
| AT (1) | ATE10383T1 (en) |
| BR (1) | BR8004320A (en) |
| CA (1) | CA1152707A (en) |
| DE (2) | DE2928141A1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3150179A1 (en) * | 1981-12-18 | 1983-06-23 | Hoechst Ag, 6230 Frankfurt | CONCENTRATED PRE-MIXTURES OF SOFT SOFTENER |
| JPS58144175A (en) * | 1982-02-23 | 1983-08-27 | ライオン株式会社 | Article for treating fiber product |
| US4497716A (en) * | 1982-12-23 | 1985-02-05 | Lever Brothers Company | Fabric softening composition |
| GB8334226D0 (en) * | 1983-12-22 | 1984-02-01 | Learonal Uk Ltd | Electrodeposition of gold alloys |
| GB8410320D0 (en) * | 1984-04-19 | 1984-05-31 | Unilever Plc | Aqueous fabric softening composition |
| GB8410321D0 (en) * | 1984-04-19 | 1984-05-31 | Unilever Plc | Aqueous concentrated fabric softening composition |
| CN1157511C (en) * | 1999-11-12 | 2004-07-14 | 花王株式会社 | Softener composition |
| US6780833B1 (en) | 1999-11-12 | 2004-08-24 | Kao Corporation | Softener composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3451927A (en) * | 1964-07-08 | 1969-06-24 | Lever Brothers Ltd | Fabric conditioner |
| FR2082249A5 (en) * | 1970-03-09 | 1971-12-10 | Colgate Palmolive Co | |
| US4155882A (en) * | 1973-08-01 | 1979-05-22 | Lever Brothers Company | Process for preparing particulate detergent compositions containing nonionic surfactants |
| GB1474688A (en) * | 1973-08-01 | 1977-05-25 | Unilever Ltd | Process for producing particulate detergent compositions |
| DE2605502A1 (en) * | 1976-02-12 | 1977-08-18 | Exquisit Kosmetik Gmbh | Washing and rinsing composition for softening textiles - nonionic surfactant, softening agent and polyglycol difatty acid ester |
| IT1097290B (en) * | 1977-06-29 | 1985-08-31 | Procter & Gamble | DETERGENT COMPOSITIONS FOR LAUNDRY |
| DE2733970A1 (en) * | 1977-07-28 | 1979-02-15 | Henkel Kgaa | Alpha-cyano-fatty acid hydroxyalkyl-amide detergent components - used in combination with surfactant(s) for cold washing textiles e.g. by machine |
-
1979
- 1979-07-12 DE DE19792928141 patent/DE2928141A1/en not_active Withdrawn
-
1980
- 1980-07-09 DE DE8080103918T patent/DE3069660D1/en not_active Expired
- 1980-07-09 AT AT80103918T patent/ATE10383T1/en active
- 1980-07-09 EP EP80103918A patent/EP0022555B1/en not_active Expired
- 1980-07-10 JP JP9335780A patent/JPS5615472A/en active Pending
- 1980-07-10 AR AR281716A patent/AR224163A1/en active
- 1980-07-11 BR BR8004320A patent/BR8004320A/en unknown
- 1980-07-11 CA CA000355973A patent/CA1152707A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3069660D1 (en) | 1985-01-03 |
| BR8004320A (en) | 1981-01-27 |
| AR224163A1 (en) | 1981-10-30 |
| ATE10383T1 (en) | 1984-12-15 |
| EP0022555B1 (en) | 1984-11-21 |
| EP0022555A1 (en) | 1981-01-21 |
| JPS5615472A (en) | 1981-02-14 |
| DE2928141A1 (en) | 1981-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4447343A (en) | Concentrated fabric softeners | |
| USRE34062E (en) | Fabric softening composition contains water-insoluble surfactant and aliphatic mono-carboxylic acid | |
| EP0021476B1 (en) | Liquid fabric softener containing a quaternary ammonium salt and method of conditioning fabrics | |
| US5880086A (en) | Laundry softener concentrates | |
| CA1167054A (en) | Mono acyl esters of bis-polyoxyalkylene ammonium compounds, their preparation and use as fabric softeners | |
| FI61713B (en) | PROCEDURE FOR FOIL TEXTILES AND FREQUENCY FRAMEWORK | |
| CA1153510A (en) | Fabric softeners | |
| IE52809B1 (en) | Textile treatment compositions and preparation thereof | |
| JP2633242B2 (en) | Fabric treatment composition and fabric treatment method | |
| US4659487A (en) | Concentrated fabric softeners | |
| CA2118368A1 (en) | Liquid fabric softener compositions | |
| JPH05106166A (en) | Fiber product softened composition and manufacture of said composition | |
| CA1152707A (en) | Fabric softener | |
| US4399043A (en) | Fabric softener | |
| US5705663A (en) | Quaternized triethanolamine difatty acid esters | |
| SE447916B (en) | TEXTILE SOFTING AND ANTISTATIC COMPOSITION CONTAINING AN ANIONIC PHOSPHORIC ACID AND A COTTONIC SOFTENING AGENT | |
| JPS6252073B2 (en) | ||
| CA1109610A (en) | Fabric softeners | |
| DE69534903T2 (en) | Use of allyl alcohol as a bad odor reducing agent | |
| US2929788A (en) | Detergent compositions composed of alkylaryl sulfonates and n-alkyl beta-aminopropionates | |
| US3625891A (en) | Wash cycle fabric softeners and method of preparing and using same | |
| AT396690B (en) | PHOSPHATE-FREE LAUNDRY DETERGENT COMPOSITION | |
| EP0803283B1 (en) | Cationic compositions containing hydroxyester | |
| GB2194561A (en) | Fabric softening compositions | |
| KR20050108004A (en) | Fabric softener composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |