WO1994005754A1 - Dispersions aqueuses d'assouplissants pour textiles - Google Patents
Dispersions aqueuses d'assouplissants pour textiles Download PDFInfo
- Publication number
- WO1994005754A1 WO1994005754A1 PCT/EP1993/002308 EP9302308W WO9405754A1 WO 1994005754 A1 WO1994005754 A1 WO 1994005754A1 EP 9302308 W EP9302308 W EP 9302308W WO 9405754 A1 WO9405754 A1 WO 9405754A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dispersions
- textile
- fatty
- quaternary ammonium
- ammonium compounds
- Prior art date
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 39
- 239000004753 textile Substances 0.000 title claims abstract description 31
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 19
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 6
- 239000004014 plasticizer Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002979 fabric softener Substances 0.000 description 4
- -1 fatty acid esters Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002190 fatty acyls Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000005486 organic electrolyte Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 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
- 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
-
- 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
- C11D1/40—Monoamines or polyamines; Salts thereof
-
- 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
Definitions
- the present patent application relates to aqueous textile softener dispersions which are acidic and are therefore able not only to give the textiles a soft feel in the aftertreatment of washed textiles in a rinsing bath, but also possibly to return them to the textiles from the previous washing cycle neutralize remaining alkaline detergent residues.
- Such quaternary ammonium compounds in particular have recently Interest obtained that contain fatty acyloxyalkyl residues bound to nitrogen.
- Such compounds have also been known for a long time, for example from DE-A-16 19 058, DE-A-19 35 499 or US 3,915,867.
- These compounds can be easily prepared, for example, by esterification of alkanolamines with fatty acids or by transesterification of fatty acid esters with alkanolamines and subsequent quaternization.
- Corresponding processes for the production on an industrial scale have also been known for a long time.
- the object of the present invention was therefore to provide aqueous plasticizer dispersions based on quaternary ammonium compounds with one, two or three long-chain acyloxyalkyl groups which are acidic and are hydrolysis-stable even after prolonged storage.
- This object is achieved according to the invention solved by dispersions which are adjusted to a pH of less than 5 with a content of the dispersions of quaternary ammonium compounds in the range of 3 to 20% by weight, preferably 5 to 15, and which are obtained by adding a long-chain primary and / or se ⁇ secondary amines are marked.
- the textile-soft acher dispersions according to the invention are surprisingly stable despite their high acid content even after prolonged storage.
- the textile softener dispersions described above can in principle contain quaternary ammonium compounds as the active ingredient which contain either one or two or three fatty acyloxyalkyl radicals. However, since such compounds can only be prepared on an industrial scale in a complex manner, textile plasticizer dispersions are preferred which contain quaternary ammonium compounds in the form of a mixture of compounds having one, two or three fatty acyloxyalkyl radicals, in particular one, two or three fatty acyloxyethyl radicals.
- quaternary ammonium compounds with fatty acyloxyalkyl radicals in addition to the compounds with fatty acyloxyethyl radicals already mentioned, those products are also suitable which contain quaternary ammonium compounds with fatty acyloxyalkyl radicals other than fatty acyloxyethyl radicals, for example quaternary arnmonium compounds with fatty acyloxypropyl radicals and with fatty acyloxy propyl radicals.
- the fatty acyl radicals can be derived from saturated and unsaturated, branched or unbranched fatty acids. In general, they are derived from fatty acids containing 12 to 22 carbon atoms.
- those are preferably used quaternary ammonium compounds which have a high proportion of fatty acyl residues which are wholly or partly derived from unsaturated fatty acids which are predominantly present in cis-For.
- Long-chain primary and / or secondary amine which is important according to the invention, surprisingly brings about, in addition to the associated slight increase in the pH, a significant improvement in the storage stability of the acidified textile-plasticizer dispersions.
- Long-chain primary or secondary amines for the purposes of the present invention are to be understood as compounds which contain a long-chain fatty alkyl or alkene radical.
- compounds which contain only one long-chain fatty alkyl or alkenyl radical may also contain a C 1 -C 3 -alkyl radical. They have their effect in particular in textile plasticizer dispersions which are adjusted to a pH of less than 3, preferably less than 2.
- Acids suitable for setting such a low pH are preferably acids from the group comprising glycolic acid, lactic acid, citric acid or phosphoric acid. They are added to the textile softener dispersions in such amounts that they set the desired low pH. In addition to the preferred acids mentioned for setting the low pH, other organic or inorganic acids can be used if required, provided they are sufficiently acidic and with the materials and textiles with which they are used in the treatment Come, are tolerated.
- a secondary amine with two C12 to C22 alkyl or alkenyl groups has proven particularly useful as the amine.
- the ditallow alkylamine is particularly preferred. Only a relatively small amount is needed to achieve the stability-improving effect Addition of amine required. In general, 0.5 to 5% by weight, based on the fabric softener dispersions, is sufficient, with an addition of 1 to 3% by weight being preferred.
- the textile plasticizer dispersions according to the invention can additionally contain auxiliaries customary in aqueous textile plasticizer dispersions, such as, for example, dispersants, preservatives, inorganic or organic electrolytes, buffer substances, viscosity regulators, dyes, fragrances or solvents.
- auxiliaries customary in aqueous textile plasticizer dispersions such as, for example, dispersants, preservatives, inorganic or organic electrolytes, buffer substances, viscosity regulators, dyes, fragrances or solvents.
- the textile softener dispersions according to the invention can additionally contain one or more other plasticizing active ingredients of other classes of compounds.
- Examples include sorbitan esters, swellable layered silicates, fatty acid condensation products with polyaines, quaternary ammonium compounds with fatty alkyl or alkenyl radicals, alkypolyglycosides or fatty acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Des dispersions acides d'assouplissants pour textiles, à base de composés d'ammonium quaternaire ayant un, deux ou trois groupes acyloxyalkyle gras sont particulièrement stables au stockage, si elles contiennent une amine primaire et/ou secondaire.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4229649.8 | 1992-09-04 | ||
DE19924229649 DE4229649A1 (de) | 1992-09-04 | 1992-09-04 | Wäßrige Textilweichmacher-Dispersionen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994005754A1 true WO1994005754A1 (fr) | 1994-03-17 |
Family
ID=6467284
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1993/002308 WO1994005754A1 (fr) | 1992-09-04 | 1993-08-26 | Dispersions aqueuses d'assouplissants pour textiles |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE4229649A1 (fr) |
WO (1) | WO1994005754A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015075063A1 (fr) * | 2013-11-21 | 2015-05-28 | Unilever Plc | Composition |
US10588839B2 (en) | 2013-11-21 | 2020-03-17 | Conopco, Inc. | Method of shaping hair |
US10617615B2 (en) | 2013-11-21 | 2020-04-14 | Conopco, Inc. | Method of treating hair |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2609058A1 (fr) | 2005-05-18 | 2006-11-23 | Stepan Company | Compositions contenant des agents adoucissants, a faible teneur en solides et a haute viscosite destinees aux textiles et leur procede de production |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0206375A1 (fr) * | 1985-05-28 | 1986-12-30 | Unilever N.V. | Compositions liquides de nettoyage et d'adoucissement |
EP0239910A2 (fr) * | 1986-04-02 | 1987-10-07 | The Procter & Gamble Company | Adoucissants biodégradables pour tissus |
EP0404471A1 (fr) * | 1989-06-19 | 1990-12-27 | Unilever Plc | Composition adoucissante pour le linge |
-
1992
- 1992-09-04 DE DE19924229649 patent/DE4229649A1/de not_active Withdrawn
-
1993
- 1993-08-26 WO PCT/EP1993/002308 patent/WO1994005754A1/fr active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0206375A1 (fr) * | 1985-05-28 | 1986-12-30 | Unilever N.V. | Compositions liquides de nettoyage et d'adoucissement |
EP0239910A2 (fr) * | 1986-04-02 | 1987-10-07 | The Procter & Gamble Company | Adoucissants biodégradables pour tissus |
EP0404471A1 (fr) * | 1989-06-19 | 1990-12-27 | Unilever Plc | Composition adoucissante pour le linge |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015075063A1 (fr) * | 2013-11-21 | 2015-05-28 | Unilever Plc | Composition |
US10588839B2 (en) | 2013-11-21 | 2020-03-17 | Conopco, Inc. | Method of shaping hair |
US10617615B2 (en) | 2013-11-21 | 2020-04-14 | Conopco, Inc. | Method of treating hair |
Also Published As
Publication number | Publication date |
---|---|
DE4229649A1 (de) | 1994-03-10 |
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DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
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122 | Ep: pct application non-entry in european phase |