WO1992008837A2 - Biodegradable fabric softeners - Google Patents
Biodegradable fabric softeners Download PDFInfo
- Publication number
- WO1992008837A2 WO1992008837A2 PCT/EP1991/002178 EP9102178W WO9208837A2 WO 1992008837 A2 WO1992008837 A2 WO 1992008837A2 EP 9102178 W EP9102178 W EP 9102178W WO 9208837 A2 WO9208837 A2 WO 9208837A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- fabric softening
- carbon atoms
- softening agent
- agent according
- Prior art date
Links
- 239000002979 fabric softener Substances 0.000 title abstract description 21
- -1 diester amines Chemical class 0.000 claims abstract description 23
- 125000004185 ester group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000004744 fabric Substances 0.000 claims description 18
- 239000004902 Softening Agent Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000003760 tallow Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 150000002148 esters Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 31
- 230000002349 favourable effect Effects 0.000 abstract description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229960004106 citric acid Drugs 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 6
- 229960002303 citric acid monohydrate Drugs 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 230000005588 protonation Effects 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000006065 biodegradation reaction Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000238578 Daphnia Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- KGOGNDXXUVELIQ-UHFFFAOYSA-N dioctadecylazanium;chloride Chemical compound Cl.CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC KGOGNDXXUVELIQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 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
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
-
- 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
-
- 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
- D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Definitions
- the present invention relates to fabric softening agents, more particularly a ine compounds containing one or more long-chain alkyl or al enyl groups.
- Fabric softeners are commonly used to render textiles soft to the touch after a laundry treatment and are incorporated into commercial laundry products such as detergents, rinsing agents, and laundry drying agents.
- Representative commercially available fabric softeners include dimethyl distearyl ammonium chloride and 1-methyl-2-tal1owalkyl-3-tal1owamido-ethyl imidazoliniurn methosulphate.
- These known fabric softeners display a serious drawback in that they have no or only very slow biodegradability, whereas their primarily domestic wide-scale use is attended with large amounts of them ending up, via the sewerage system, in the city waste water and complicating its purification.
- Canadian Patent No. 1 164470 discloses the use of a wide range of protonated amines as additives for a number of formulations, including fabric softener formulations. No indication is given as to whether any of the disclosed compounds could themselves exhibit softening activity.
- EP A 281 975 a wide range of amines is disclosed which act as a softening-activity imparting ingredient if formulated together with a carboxylic acid having of from 1 to 24 carbon atoms. No indication is given as to whether any of the disclosed compounds would be biodegradable.
- EP 293953 pertains to fabric softeners comprising quaternary ammonium fabric softeners containing a single ester group.
- the disclosed quaternary ammonium compounds are stated to be biodegradable, but further improvement in this respect is desired.
- the disclosure does not pertain to the problem of formulating effective, biodegradable softeners based on amines.
- DE-PS-2728841 discloses fabric softeners based on quaternary ammonium compounds containing two ester moieties. The disclosure does not pertain to biodegradability, nor does it address the aforementioned problem of formulating effective softeners based on amine compounds.
- the present invention provides a biodegradable fabric softening agent which comprises as essential constituent an ester group-containing cationic nitrogen compound of the formula 1:
- R represents an alkyl or alkenyl group having 7-22 carbon atoms
- R' represents an alkyl or alkenyl group having 7-21 carbon lb atoms
- R" and R 1 may be the same or different and represent an alkyl or hydroxyalkyl group having 1-6 carbon atoms, p equals 0 or 1, and Q X" represents an anion.
- the amine is required to be protonated to provide a favourable softening action. This is generally effected by employing the amine in fabric softening compositions having a low enough pH to have the amine 5 present in the rinse in the protonated form. This means that the amine is present in softener compositions in conjunction with an acid. Hence the counterion X" is an acid radical.
- an effective softener is 0 provided by the instant select group of protonated amines without additional steps being required.
- additional steps such as described in EP 417987 referred to above, will negatively affect the performance of the instant softening agents.
- the steps according to EP 417987 are applied to the amines according to the present invention, an even better softening performance is attained as compared with Armeen ® M2HT. Rather, it is stressed that no additional steps being required shows the unexpected and unique performance of the instant selected amines.
- the cationic nitrogen compound is of the formula 2:
- R' wherein R represents an alkyl or alkenyl group having 8-22 carbon atoms and R', R", R"', and X- may have the above-disclosed meanings.
- the cationic nitrogen compound is of the formula 3:
- R and R' represent an alkyl or alkenyl group having 8-22 carbon atoms and R", R'", and X ⁇ may have the above-disclosed meanings.
- amine compounds of the latter formula display a further advantage in that they are more readily biodegradable than Armeen ® M2HT disclosed in EP-A-417 987, particularly if R" and R" 1 are methyl and R and R' are C15/17 saturated hydrocarbon.
- R and R' preferably represent essentially linear alkyl or alkenyl groups that may be derived from fatty acids or mixtures thereof.
- alk(en)yl groups usually derived from natural fatty acid mixtures, such as tallow alkyl, hydrogenated tallow alkyl (H-tallow alkyl), and coco alkyl, that are made use of.
- These groups are also preferred for use in the biodegradable fabric softeners according to the present invention on account of their easy availability at a low price.
- the proton in the protonated amine may be hydrogen derived from the acid fabric softener medium.
- the counterion X" is an acid radical, preferably of an organic carboxylic acid and more particularly of a hydroxycarboxylic acid. Most suitable are citric acid, malic acid, and glycolic acid. Of course, acids are well-known to the person of ordinary skill in the art, and need no further elucidation here. To affect protonation of the instant amines the acid may simply be mixed with an equivalent amount of amine. Complicated melting processes, such as disclosed in EP-A-281975, are not required.
- the present cationic nitrogen compounds can be prepared in the manner known for the preparation of analogous compounds.
- preparation of a representative cationic nitrogen compound according to the present invention is described in detail, and the remaining biodegradable fabric softening agents according to the present invention are directly accessible to the skilled man through adaptation of the starting substances concerned.
- the manner in which the present biodegradable fabric softening agent is applied is the same as for the conventional, now commercially available fabric softeners.
- the usual possibilities in this respect are either using the agent in admixture with detergent, or adding it separately, i.e. during the rinse-cycle as a rinsing agent or else in the dryer.
- the instant softening agents are particularly advantageous as rinse-cycle added softeners.
- the fabric softening action envisaged and actualised here is at least the same as for the conventional quaternary ammonium fabric softeners.
- a portion of the fabric softener will end up in the waste water, where, because of the present invention, there will be less harm to the environment as a result of accelerated biodegradability.
- the present biodegradable fabric softening agents were tested for their fabric softening performance and found to be comparable with dimethyl dihardened tallow ammonium chloride, distearyl ammonium chloride and l-methyl-2-tallowalkyl-3-tallowamido-ethyl imidazoliniu methosulphate.
- test towels treated with the fabric softeners in question were line dried for 24 hours and then cut up into STRIPS of 10 x 20 cm*--.
- a test panel evaluated the softening action as compared with that of the standard test detergents (IEC), whereupon the observational data was statistically processed in accordance with DIN standard 10954.
- the present quaternary ammonium compounds were tested for biodegradability in accordance with the EEC/OECD guidelines OECD 301D "closed bottle test".
- OECD 301D closed bottle test
- a test compound is added to an aqueous solution of mineral salts and exposed for 28 days under aerobic conditions to a relatively small number of micro-organisms.
- the formal test regulations were departed from on the following minor issues:
- the inoculum was taken from an apparatus containing activated sludge preconditioned in accordance with proposed amendments to the EEC guidelines; ammonium chloride was not included in the medium to avoid nitrification;
- the dissolved oxygen concentrations were determined electrochemically using an oxygen electrode (WTW Trioxmatic EO 200) and an oxygen gauge (WTW 0X1 530), and biodegradability was calculated as the ratio of biological oxygen demand (BOD) to theoretical oxygen demand (ThOD) : BOD/ThOD.
- the conversion was monitored with the aid of either TLC or GC. After 6 hours, the composition of the product was as follows: 90.4% of diester amine, 4.9% of onoester amine, and 4.7% of free fatty acid.
- the diesteramine was converted into the corresponding cationic nitrogen compound by protonation with citric acid monohydrate. Said protonation was carried through by adding to water, with stirring, 5 wt% of the diester amine and the equivalent amount of 1.66 wt% of citric acid monohydrate. In the case of the embodiment using excess acid 5 wt% of the diester amine and 5 wt% of citric acid monohydrate were ' added to water. The addition of the diester amine to water resulted in a stable dispersion.
- the ono ⁇ steramine was converted into the corresponding cationic nitrogen compound by protonation with citric acid monohydrate. Said protonation was carried through by adding to water, with stirring, 5 wt% of the monoester amine and the equivalent amount of 2.8 wt% of citric acid monohydrate. In the case of the embodiment using excess acid 5 wt% of the monoester amine and 5 wt% of citric acid monohydrate were added to water. The addition of the monoester amine to water resulted in a clear solution.
- Biodegradability is indicated by means of the percentage of degradation after 28 days. A compound is considered to be “readily biodegradable” if biodegradation is ⁇ 60%. Further improved biodegradability is shown if the percentage is over 70%, which may be regarded as ultimate biodegradation. The margin of error in these tests usually is 10%.
- R and R 1 are saturated C15/17 hydrocarbon
- R" is a hardened tal low al kyl radical
- Citri c acid equiv. amt. ++ 78
- Citric acid excess amt. +++
- Citric acid equiv. amt. 63 B Citric acid, excess amt.
- Citric acid equiv. amt. 59 C Citric acid, excess amt.
- protonated amines according to the present invention are favourable biodegradable softeners. It is also apparent that protonated amine formulations not in accordance with the present invention may make viable softeners but will not exhibit said surprising softening effect without additional steps.
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP51799591A JPH07500637A (en) | 1991-11-14 | 1991-11-14 | biodegradable fabric softener |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL9002506 | 1990-11-16 | ||
NL9002506 | 1990-11-16 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1992008837A2 true WO1992008837A2 (en) | 1992-05-29 |
WO1992008837A3 WO1992008837A3 (en) | 1992-07-09 |
Family
ID=19857989
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1991/002178 WO1992008837A2 (en) | 1990-11-16 | 1991-11-14 | Biodegradable fabric softeners |
Country Status (2)
Country | Link |
---|---|
EP (1) | EP0557343A1 (en) |
WO (1) | WO1992008837A2 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0568297A1 (en) * | 1992-04-28 | 1993-11-03 | Unilever Plc | Rinse conditioner |
US5429755A (en) * | 1994-06-16 | 1995-07-04 | Lever Brothers Company | Fabric conditioning molecules derived from glycerol and betaine |
WO2002050354A1 (en) * | 2000-12-19 | 2002-06-27 | M & J Fibretech A/S | Method and plant for without a base web producing an air-laid hydroentangled fibre web |
WO2003095601A1 (en) * | 2002-05-13 | 2003-11-20 | Firmenich Sa | Branched fatty acid derivatives as anti-gelling or viscosity-control ingredients |
WO2020227322A1 (en) * | 2019-05-06 | 2020-11-12 | Stepan Company | Esteramine compositions |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3342840A (en) * | 1964-03-23 | 1967-09-19 | Shell Oil Co | Cationic ester production |
FR2356627A1 (en) * | 1976-07-02 | 1978-01-27 | Unilever Nv | CLOTH TREATMENT AGENTS |
EP0000225A1 (en) * | 1977-06-29 | 1979-01-10 | THE PROCTER & GAMBLE COMPANY | Solid detergent composition for improved greasy soil removal |
EP0295739A2 (en) * | 1987-06-09 | 1988-12-21 | The Procter & Gamble Company | Method for preparing biodegradable fabric treatment compositions |
EP0330261A2 (en) * | 1988-02-25 | 1989-08-30 | The Procter & Gamble Company | Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts |
EP0409502A2 (en) * | 1989-07-17 | 1991-01-23 | Unilever Plc | Fabric softening composition |
-
1991
- 1991-11-14 EP EP19910919783 patent/EP0557343A1/en not_active Withdrawn
- 1991-11-14 WO PCT/EP1991/002178 patent/WO1992008837A2/en not_active Application Discontinuation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3342840A (en) * | 1964-03-23 | 1967-09-19 | Shell Oil Co | Cationic ester production |
FR2356627A1 (en) * | 1976-07-02 | 1978-01-27 | Unilever Nv | CLOTH TREATMENT AGENTS |
EP0000225A1 (en) * | 1977-06-29 | 1979-01-10 | THE PROCTER & GAMBLE COMPANY | Solid detergent composition for improved greasy soil removal |
EP0295739A2 (en) * | 1987-06-09 | 1988-12-21 | The Procter & Gamble Company | Method for preparing biodegradable fabric treatment compositions |
EP0330261A2 (en) * | 1988-02-25 | 1989-08-30 | The Procter & Gamble Company | Stable biodegradable fabric softening compositions containing 2-hydroxypropyl monoester quaternized ammonium salts |
EP0409502A2 (en) * | 1989-07-17 | 1991-01-23 | Unilever Plc | Fabric softening composition |
Non-Patent Citations (1)
Title |
---|
J. AM. CHEM. SOC. vol. 109, no. 20, 1987, pages 6209 - 6210; R.A. MOSS ET AL.: 'An Imidazole-Functionalized Phosphatidylcholine Derivate: Nucleophilic Vesicles with Adjustable Reactivity' * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0568297A1 (en) * | 1992-04-28 | 1993-11-03 | Unilever Plc | Rinse conditioner |
EP0569184A1 (en) * | 1992-04-28 | 1993-11-10 | Unilever Plc | Rinse conditioner |
US5403500A (en) * | 1992-04-28 | 1995-04-04 | Lever Brothers Company | Rinse conditioner |
US5525244A (en) * | 1992-04-28 | 1996-06-11 | Levers Brothers Company, Division Of Conopco, Inc. | Rinse conditioner |
US5429755A (en) * | 1994-06-16 | 1995-07-04 | Lever Brothers Company | Fabric conditioning molecules derived from glycerol and betaine |
US5527477A (en) * | 1994-06-16 | 1996-06-18 | Lever Brothers Company, Division Of Conopco, Inc. | Fabric conditioning molecules derived from glycerol and betaine |
WO2002050354A1 (en) * | 2000-12-19 | 2002-06-27 | M & J Fibretech A/S | Method and plant for without a base web producing an air-laid hydroentangled fibre web |
WO2003095601A1 (en) * | 2002-05-13 | 2003-11-20 | Firmenich Sa | Branched fatty acid derivatives as anti-gelling or viscosity-control ingredients |
WO2020227322A1 (en) * | 2019-05-06 | 2020-11-12 | Stepan Company | Esteramine compositions |
Also Published As
Publication number | Publication date |
---|---|
WO1992008837A3 (en) | 1992-07-09 |
EP0557343A1 (en) | 1993-09-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5637743A (en) | Quaternary ammonium surfactants derived from tertiary amines and fabric softeners containing quaternary ammonium surfactants | |
EP1639067B1 (en) | Mdea ester quats with high content of monoester in blends with tea ester quats. | |
EP0721936B1 (en) | Liquid softener composition and quaternary ammonium salt | |
RU98105781A (en) | STABLE COMPOSITIONS OF TENSION AGENTS | |
JP2001131871A (en) | Quaternary ammonium salt composition | |
JP2941297B2 (en) | Imidazole compound and cloth treating composition containing the same | |
US4622154A (en) | Aqueous fabric softening composition | |
WO1992008837A2 (en) | Biodegradable fabric softeners | |
EP0638639B1 (en) | Biodegradable fabric softening composition | |
JPH07505189A (en) | Concentrated fabric softening composition | |
JP2956274B2 (en) | Liquid softener composition | |
AU643858B2 (en) | Polyamide salts | |
US5456846A (en) | Method of conditioning fabrics with glyceric acid based biodegradable moelcules | |
US5543066A (en) | Biodegradable fabric softening composition | |
JP3256747B2 (en) | Liquid softener composition | |
EP0486113A2 (en) | Biodegradable fabric softeners derived from aspartic acid or glutaminic acid | |
JPH0819619B2 (en) | Softener composition for textile products and method for softening textile materials using the same | |
WO1993017085A1 (en) | Biodegradable fabric softeners | |
US5734069A (en) | Biodegradable amidoaminoesters | |
JPH04333666A (en) | Liquid softening agent composition | |
JPH07102479A (en) | Liquid softener composition | |
JPH10251972A (en) | Hydrolysis inhibitor for cationic surfactant and cationic surfactant composition | |
JP4271562B2 (en) | Triester cation composition and process for producing the same | |
DE60010059T2 (en) | ESTERQUATS, THEIR INTERMEDIATES, METHOD FOR THEIR PRODUCTION AND THEIR USE | |
JP3827864B2 (en) | Softener composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): JP US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): AT BE CH DE DK ES FR GB GR IT LU NL SE |
|
AK | Designated states |
Kind code of ref document: A3 Designated state(s): JP US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A3 Designated state(s): AT BE CH DE DK ES FR GB GR IT LU NL SE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1991919783 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 1991919783 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1991919783 Country of ref document: EP |