EP0038862B1 - Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles - Google Patents
Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles Download PDFInfo
- Publication number
- EP0038862B1 EP0038862B1 EP19790301558 EP79301558A EP0038862B1 EP 0038862 B1 EP0038862 B1 EP 0038862B1 EP 19790301558 EP19790301558 EP 19790301558 EP 79301558 A EP79301558 A EP 79301558A EP 0038862 B1 EP0038862 B1 EP 0038862B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition according
- amido amine
- water
- groups
- foregoing
- 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
- 239000000203 mixture Substances 0.000 title claims description 23
- -1 amido amine salts Chemical class 0.000 title claims description 19
- 239000002979 fabric softener Substances 0.000 title claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000006185 dispersion Substances 0.000 claims description 12
- 239000004744 fabric Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003760 tallow Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000002862 amidating effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/405—Acylated polyalkylene polyamines
Definitions
- This invention relates to fabric softener compositions containing amido amino salts, and the use thereof for the treatment of fabrics.
- the five most commonly found active softening agents in consumer products purchased in the U.S.A. are all quaternary nitrogen compounds: (1) a methyl chloride quaternised tertiary amine, (II) a dimethyl sulphate quaternised tertiary amine, (III) a dimethyl sulfphate quaternised polyethoxylated di amido amine, (IV) a dimethyl sulphate quaternised polypropoxylated diamido amine and (V) a dimethyl sulphate quaternised alkyl amido alkyl imidazoline.
- German Patent Application No. 2520150 (Brit. Pat. 1,483,984) for example describes the preparation of a quaternised mixture of a diamido diethylenetriamine and an imidazoline.
- the presence of the quaternised diamido diethylenetriamine is said to lower the softening effect of the mixture compared with the quaternised imidazoline alone but to improve the rewettability of the fabric after washing, which most known fabric softeners reduce.
- the patent implies that quaternised diamido diethylenetriamines alone are not effective fabric softeners.
- unquaternised diamido amines, their salts and partial salts tend to be intractable solids at room temperature, which even on dilution with a suitable solvent e.g. 25% of a lower alkanol such as isopropanol, hexylene glycol, propylene glycol or mixtures thereof, are still to viscous for convenient handling.
- a suitable solvent e.g. 25% of a lower alkanol such as isopropanol, hexylene glycol, propylene glycol or mixtures thereof, are still to viscous for convenient handling.
- Our invention therefore provides a novel composition which comprises (A) a water dispersible salt or partial salt of an amido amine of the average formula: wherein an average of from 20% to 80% of the R groups per molecule are acyl groups having an average of from 12 to 22 and preferably 16 to 18 carbon atoms, at least 20% of the R groups are -CH 2 CH 2 0H or -CH Z CH(OH)CH 3 or mixtures of these groups and any other R group is hydrogen, n is 2 or 3 and m is an integer from 2 to 5; which amido amine is at least partially (e.g. from 10% to 80%, preferably 20 to 60%) neutralised with a lower carboxylic or hydroxycarboxylic acid, e.g.
- acetic, formic, propionic, lactic or glycollic acid and (B) a compatible amount, up to 70% preferably 10 to 50%, e.g. 25% by weight, of a fluid, water miscible hydroxyaliphatic solvent.
- R groups are acyl they can be saturated, e.g. stearoyl, monounsaturated, e.g. oleoyl, polyunsaturated or may be mixtures of these types.
- the preferred compounds are those wherein n and m are each 2.
- the acyl groups are derived from tallow or lard.
- any water miscible hydroxy-, or polyhydroxy- alkane or alkylether having a viscosity of less than 0.03 N.S.M.- 2 (30 centipoise) at 20°C may be used as the solvent.
- Preferred examples include isopropanol, hexylene glycol, propylene glycol, ethylene glycol monomethylether and mixtures thereof.
- the product may additionally contain a minor proportion of salts of inorganic acids especially sulphites, which help to stabilise the product against oxidation.
- the amido amines may be obtained by controlled alkoxylation of an amido amine prepared by amidating a polyalkylene polyamine, e.g. by heating it with the necessary amount of a glyceryl ester to provide the desired alkyl groups in the correct proportions.
- the polyamine may be heated with a fatty acid or methyl ester thereof while distilling off water or methanol respectively.
- the heating is carried out at temperatures above 100°C but not sufficiently high to decompose any glycerol formed.
- the temperature should be maintained below 180°C and preferably at 120 to 160°C, e.g. 140°C.
- Heating is preferably carried in an inert atmosphere to prevent colour degradations, e.g. under nitrogen for from 2 to 6, preferably 4 hours.
- the product may then be reacted with ethylene or propylene oxide at a temperature between 100 and 200°C.
- the presence of a catalyst should generally be avoided in order to prevent formation of polyoxyalkylene chains.
- the solvent may be added after alkoxylation to facilitate dispersion of the product in water.
- the invention provides softening compositions comprising the amido amine salts, any glycerol remaining from the preparation of the diamide and the added solvent.
- the novel products of our invention may be used in conventional manner, e.g. as a post-rinse after washing.
- substantially monoethoxylated products of our invention are significantly more fluid in the presence of organic solvent than corresponding non-ethoxylated diamidoamines.
- the vessel was evacuated and flushed with nitrogen to displace most of the air.
- the reactor charge was then cooled to 120°C and 132 kg of ethylene oxide fed in slowly cooling to maintain 120°C.
- the product is a hazy, mobile, pumpable liquid at 20°C.
- the above preparation was repeated but without the addition of solvents.
- the product was a waxy solid which was fluid at 40 to 45°C. On dilution to 75% with isopropanol the product became pourable at 20°C.
- Domestic fabric softener formulations normally consist of concentrated fabric softener solutions as prepared in examples 1 and 2 dispersed into water to yield translucent liquids containing normally 2% to 8% "active" softener.
- active we mean the non solvent component in a fabric softener concentrate.
- Example 3 the appearance and stability of the aqueous dispersion of the concentrates is important for consumer acceptability. Products which yield stable dispersions with viscosities in the range 0.1 to 0.5 N.S.M.- 2 (100 to 500 centipoise) as measured by a "Brookfield" viscometer, model LVT, find ready consumer acceptability. Products which give dispersions which change viscosity on storage are obviously undesirable.
- types II, III, IV and V give dispersions at 6% "active" with viscosities in the range 0.01 to 0.03 N.S.M.- 2 (10 to 30 cp) and are often formulated with other additives to increase their viscosity.
- Dispersions prepared from products of examples 1 and 2 are stable to extend storage.
- the weight of active material used was in the range 0.1 to 0.3% of the napkin weight.
- the napkins were then wrung out by hand and dried on a clothes line under the same conditions.
- Example 2 shows better rewettability properties than type I which has a similar softening ability.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (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)
Claims (8)
1. Composition fluide, dispersable dans l'eau pour utilisation comme adoucissant pour matières textiles, caractérisée en ce qu'elle comprend:
(A) un sel ou un sel partiel, dispersable dans l'eau, d'une amido-amine de formule moyenne:
dans laquelle une moyenne de 20 à 80% des groupes R par molécule sont des groupes acyles ayant en moyenne de 12 à 22 atomes de carbone, au moins 20% des groupes R sont ―CH2CH2OH ou -CHZCHOHCH3 ou des mélanges de ces groupes et tout autre groupe R est l'hydrogène, n est 2 ou 3 et m est un nombre entier compris entre 2 et 5; cette amido-amine ayant été au moins partiellement neutralisée avec un acide carboxylique ou hydroxy-carboxylique ayant de 1 à 3 atomes de carbone, et
(B) jusqu'à 70% en poids d'un solvant hydroxylé aliphatique, fluide, miscible à l'eau.
2. Composition selon la revendication 1, caractérisée en ce que le groupe acyle dérive du suif ou du lard.
3. Composition selon l'une des revendications 1 et 2, caractérisée en ce que l'amido-amine est neutralisée entre 10% et 80% avec l'acide lactique ou l'acide acétique.
4. Composition selon l'une quelconque des revendications précédentes, contenant de 10 à 50% en poids de la composition, en solvant hydroxylé aliphatique.
5. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que le solvant hydroxylé aliphatique est un hydroxy- ou polyhydroxyalcane ou éther alkylique.
6. Composition selon la revendication 5, caractérisée en ce que le solvant hydroxylé aliphatique a moins de 4 atomes de carbone.
7. Composition selon l'une quelconque des revendications précédentes, caractérisée en ce que n et m sont chacun 2.
8. Procédé d'adoucissement des matières textiles, caractérisé en ce qu'il consiste à mettre sur les matières textiles une solution ou une dispersion aqueuse d'une composition selon l'une quelconque des revendications précédentes.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE7979301558T DE2966608D1 (en) | 1979-08-03 | 1979-08-03 | Compositions containing amido amine salts, and their use as fabric softeners |
| EP19790301558 EP0038862B1 (fr) | 1979-08-03 | 1979-08-03 | Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19790301558 EP0038862B1 (fr) | 1979-08-03 | 1979-08-03 | Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0038862A1 EP0038862A1 (fr) | 1981-11-04 |
| EP0038862B1 true EP0038862B1 (fr) | 1984-02-01 |
Family
ID=8186412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19790301558 Expired EP0038862B1 (fr) | 1979-08-03 | 1979-08-03 | Compositions contenant les sels d'amidoamines et leur utilisation comme agents adoucissants pour matières textiles |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0038862B1 (fr) |
| DE (1) | DE2966608D1 (fr) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8508129D0 (en) * | 1985-03-28 | 1985-05-01 | Procter & Gamble Ltd | Textile treatment composition |
| DE3601856A1 (de) * | 1986-01-23 | 1987-07-30 | Henkel Kgaa | Textilbehandlungsmittel |
| FR2613386B1 (fr) * | 1987-04-04 | 1993-06-18 | Sandoz Sa | Nouvelles compositions pour le finissage des matieres fibreuses |
| US4762645A (en) * | 1987-11-16 | 1988-08-09 | The Procter & Gamble Company | Detergent plus softener with amide ingredient |
| DE3842057A1 (de) * | 1988-12-14 | 1990-06-28 | Henkel Kgaa | Textile weichmacher fuer flotten mit hohen gehalten an elektrolyten und/oder optischen aufhellern |
| DE3901820A1 (de) * | 1989-01-23 | 1990-08-09 | Henkel Kgaa | Textilbehandlungsmittel |
| DE4111648A1 (de) * | 1991-04-10 | 1992-10-15 | Henkel Kgaa | Textilbehandlungsmittel mit verbesserter wasserdispergierbarkeit |
| US5433869A (en) * | 1992-12-22 | 1995-07-18 | Colgate-Palmolive Co. | Liquid fabric conditioning composition containing amidoamine softening compound |
| MY108928A (en) * | 1992-12-22 | 1996-11-30 | Colgate Palmolive Co | Liquid fabric softening composition containing amidoamine softening compound |
| GB9301811D0 (en) * | 1993-01-29 | 1993-03-17 | Unilever Plc | Fabric softener composition |
| DE19625937A1 (de) | 1996-06-28 | 1997-01-23 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Mono-, Di- oder Oligoamidalkoxylaten |
| US5747108A (en) * | 1997-03-19 | 1998-05-05 | Colgate-Palmolive Co. | Super-concentrated liquid rinse cycle fabric softening composition |
| US5747109A (en) * | 1997-03-19 | 1998-05-05 | Colgate-Palmolive Co. | Method of preparing super-concentrated liquid rinse cycle fabric softening composition |
| DE19756680A1 (de) * | 1997-12-19 | 1999-06-24 | Henkel Kgaa | Fettsäureamidoamide |
| US6780834B2 (en) | 2002-07-31 | 2004-08-24 | Colgate-Palmolive Co. | Fabric conditioning compositions containing an amine acid softening compound |
| EP1902083B1 (fr) | 2005-06-29 | 2010-10-20 | Colgate-Palmolive Company | Amidoamines ou amidoquats oligomères pour des compositions de traitement de tissu ou des cheveux |
| JP2010531324A (ja) | 2007-06-28 | 2010-09-24 | ニコックス エス エイ | １，４−ブタンジオールモノナイトレートの製造方法 |
| EP3547994A1 (fr) | 2016-12-01 | 2019-10-09 | Croda, Inc. | Ingrédients destinés à être utilisés dans des compositions de soins personnels |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3844959A (en) * | 1972-10-16 | 1974-10-29 | Procter & Gamble | Detergent composition with an amido-amine fabric softening agent |
| US3933871A (en) * | 1973-11-12 | 1976-01-20 | Armstrong Chemical Company, Inc. | Fabric softener compound and processes for preparing and using the same |
| FR2273901A1 (fr) * | 1974-06-06 | 1976-01-02 | Azote & Prod Chim | Composition pour le traitement de textiles |
| US4039565A (en) * | 1975-06-26 | 1977-08-02 | Ashland Oil, Inc. | Quaternized amidoamines |
| DE2539310A1 (de) * | 1975-09-04 | 1977-03-17 | Hoechst Ag | Textilweichmacher |
-
1979
- 1979-08-03 DE DE7979301558T patent/DE2966608D1/de not_active Expired
- 1979-08-03 EP EP19790301558 patent/EP0038862B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0038862A1 (fr) | 1981-11-04 |
| DE2966608D1 (en) | 1984-03-08 |
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