EP1018541A1 - Compositions adoucissantes et transparentes - Google Patents
Compositions adoucissantes et transparentes Download PDFInfo
- Publication number
- EP1018541A1 EP1018541A1 EP99100154A EP99100154A EP1018541A1 EP 1018541 A1 EP1018541 A1 EP 1018541A1 EP 99100154 A EP99100154 A EP 99100154A EP 99100154 A EP99100154 A EP 99100154A EP 1018541 A1 EP1018541 A1 EP 1018541A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fabric softener
- fatty acids
- parts
- mass
- softener according
- 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.)
- Withdrawn
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- 239000000203 mixture Substances 0.000 title claims abstract description 31
- 239000002979 fabric softener Substances 0.000 title claims abstract description 27
- 238000009472 formulation Methods 0.000 claims abstract description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- 229940050176 methyl chloride Drugs 0.000 claims abstract description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 34
- 239000000194 fatty acid Substances 0.000 claims description 34
- 229930195729 fatty acid Natural products 0.000 claims description 34
- 150000004665 fatty acids Chemical class 0.000 claims description 32
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 6
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003784 tall oil Substances 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 235000019486 Sunflower oil Nutrition 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 3
- 229940008406 diethyl sulfate Drugs 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- 239000002600 sunflower oil Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 210000000003 hoof Anatomy 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 description 31
- 239000000047 product Substances 0.000 description 12
- 239000000975 dye Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000002304 perfume Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 101000916289 Ctenocephalides felis Salivary antigen 1 Proteins 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 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
- -1 Ester compounds Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical group CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101500021084 Locusta migratoria 5 kDa peptide Proteins 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic 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
- C11D3/0005—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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2068—Ethers
Definitions
- the invention relates to fabric softener formulations based on or more cationic surfactants and at least one other Component that gives the overall formulation a water-bright and clear Give appearance.
- the object of the present invention was therefore to overcome these disadvantages of the prior art to avoid technology and fabric softener formulations ask which one in comparison to the comparable products of the State of the art an at least equally good spectrum of activity have, but also have a clear and water-bright appearance, whose production can be carried out with reduced energy expenditure and their handling is easy for end users Application guaranteed.
- aqueous fabric softeners in which as Alkanolamines methyldiethanolamine, methylethanolisopropanolamine, methyldiisopropanolamine, Triisopropanolamine or triethanolamine can be used.
- aqueous fabric softeners based on esters from fatty acids and alkanolamines in a molar ratio of 1: 1.6 to 1: 2 be implemented.
- the quaternary compounds of general use which are also used according to the invention Formula (I) are according to those well known in the art Processes by esterification of alkanolamines such as triethanolamine (TEA), Methyl-diethanolamine (MDEA), methyl-diisopropanolamine (MDIA), methylethanol-isopropanolamine (MEIPA), triisopropanolamine (TIPA) with fatty acid and subsequent quaternization.
- TIPA triethanolamine
- MDEA Methyl-diethanolamine
- MDIA methyl-diisopropanolamine
- MEIPA methylethanol-isopropanolamine
- TIPA triisopropanolamine
- Ester compounds based on triethanolamine such as N-methyl, N, N-bis (beta-C 14-18 -acyloxyethyl), N-beta-hydroxyethyl ammonium methosulfate, are particularly widespread and are available under trade names such as TETRANYL® AT 75 (trademark of KAO Corp.), STEPANTEX® VRH 90 (trademark of Stepan Corp.) or REWOQUAT® WE 18 (trademark of Witco Surfactants GmbH).
- the fatty acids for the esterification or transesterification are those on this Field known and usual monobasic fatty acids based on natural vegetable or animal oils with 6-22 carbon atoms, especially with 14-18 carbon atoms, such as oleic acid, linoleic acid, linolenic acid, and in particular rapeseed oil fatty acid, soybean oil fatty acid, sunflower oil fatty acid, Tall oil fatty acid which alone or in a mixture in the form of its glycerides, methyl or Ethyl esters or as free acids can be used.
- oleic acid linoleic acid, linolenic acid
- rapeseed oil fatty acid soybean oil fatty acid
- sunflower oil fatty acid Tall oil fatty acid which alone or in a mixture in the form of its glycerides, methyl or Ethyl esters or as free acids can be used.
- Tall oil fatty acid which alone or in a mixture in the form of its glycerides, methyl
- the iodine number is the amount of iodine required by 100 g of the compound to saturate the Double bonds is added.
- fatty acids with iodine numbers in the range from approximately 40 to 160 are preferred, but in particular rapeseed oil fatty acids, sunflower oil fatty acids, soybean oil fatty acids and tall oil fatty acids, with iodine numbers in the range from approximately 80 to 150. They are commercially available products and are offered by various companies under their respective trade names.
- the esterification or transesterification is carried out according to known methods.
- the alkanolamine with the desired degree of esterification corresponding amount of fatty acid or fatty acid ester optionally in the presence of a catalyst, for.
- methanesulfonic acid reacted under nitrogen at 160-240 ° C and the water of reaction or alcohol formed is distilled off continuously, the pressure being able to be reduced to complete the reaction.
- the fatty acids and Alkanolamine in the ratio implemented so that in view of the desired application properties of the end products a degree of esterification from 1.6 to 2.0 results, a is particularly preferred according to the invention Degree of esterification from 1.8 to 2.0.
- the connections thus made are technical reaction mixtures, which are predominantly in the form of diesters.
- the subsequent quaternization is also carried out using known methods.
- the procedure according to the invention is such that the ester, optionally under Use of a solvent, preferably isopropanol, ethanol, 1,2-propylene glycol and / or dipropylene glycol, at 60-90 ° C with equimolar Amounts of the quaternizing agent with stirring, if appropriate under pressure, and the completion of the reaction by controlling the Total number of amines is monitored.
- a solvent preferably isopropanol, ethanol, 1,2-propylene glycol and / or dipropylene glycol
- quaternizing agents used are organic or inorganic acids, but preferably short-chain dialkyl phosphates and sulfates such as in particular dimethyl sulfate, diethyl sulfate, dimethyl phosphate, Diethyl phosphate, short chain halogenated hydrocarbons, in particular Methyl chloride.
- alkoxylated phenols which have one or more May contain alkyl substituents, such as ethoxylated and / or propoxylated phenol, o / m / p-cresol, thymol, p-tert.
- alkyl substituents such as ethoxylated and / or propoxylated phenol, o / m / p-cresol, thymol, p-tert.
- Butyl phenol benzyl alcohol.
- alkoxylated branched short-chain alcohols with 3 to 6 carbon atoms such as Isopropanol, butanol-2,2-methyl-propanol-1,3-methyl-butanol-1,2-methyl-butanol-1, and their alkoxylation products.
- the degree of alkoxylation is 0 to about 8, with technical ones according to the invention Mixtures with an average degree of alkoxylation of 0 or> 2.5 to about 3.5 are preferred.
- the compounds of component B can be used as a mixture with one another and / or with one another in amounts of about 5 to 30% by weight, based on the total mixture, preferably in amounts of 10 to 25 % Are used.
- the fabric softeners are prepared by emulsifying or dissolving the quaternized compounds A 1 - A 5 with the use of compounds of the general formula B, by adding the respective individual components to water with stirring. In principle, the usual procedures in this field can be applied.
- the procedure according to the invention is such that water is initially introduced at room temperature, with good stirring first the dye solution, then the antifoam emulsion which may be required and finally the plasticizer and component B) are stirred in as a mixture or in any order. Perfume oil is then metered in and, if necessary, a certain amount of an electrolyte solution in order to reduce the viscosity of the finished formulation.
- the fabric softeners according to the invention can contain the stated components within the limits customary in this field, such as, for example, 15 to 35% by weight of the compounds of the general formula A; 5 to 30% by weight of at least one of the compounds of the general formula B; 0.5 to 18% by weight of one or more of the customary auxiliaries and additives, for example 0.05 to 1% by weight of dyes, 0.05 to 1% by weight of preservatives, 0.1 to 12% by weight of short-chain alcohols / diols with 2 to 6 C atoms, 0.1 to 1% by weight of defoaming agents and in particular 0.1 to 1.5% by weight of an alkali and / or alkaline earth salt; 0.1 to 1.5% by weight perfume oil and the rest 100% (ad 100) water.
- the customary auxiliaries and additives for example 0.05 to 1% by weight of dyes, 0.05 to 1% by weight of preservatives, 0.1 to 12% by weight of short-chain alcohols / diols with
- the application concentration after dilution with water lies in the range depending on the application from 0.1 to 10 g of fabric softener per liter of treatment liquor.
- Demineralized water is initially introduced at room temperature, the dye solution is added and the quaternary ammonium compound (Quat; component A) is slowly mixed into the water phase with constant stirring. Subsequently, component B is added to the mixture of water and quat with stirring until it is clearly dissolved at 20 ° C. This formulation is then cooled to 4 ° C and must be clearly transparent at this temperature. If necessary, an additional amount of solubilizer B is stirred in until the mixture is clear at 4 ° C. At the same time as, before or after the addition of component B, alcohols, preferably glycols with boiling points> 120 ° C., can be stirred into the reaction mixture to increase the flash point of the finished formulation.
- solvents preferably glycols with boiling points> 120 ° C.
- the perfume oil is then added at room temperature with stirring and, if necessary, mineral salts are added to adjust the viscosity in the case of highly viscous solutions in order to improve the stirrability and flowability of the mixture.
- the chlorides of the alkali or alkaline earth metals can be used as mineral salts in amounts of about 0.1 to 1.5% by weight, preferably in the form of their 10 to 30% aqueous solutions, in particular an aqueous calcium chloride solution.
- Example 1 water 47.4 parts by mass dye 0.8 parts by mass Component A1 30.6 parts by mass Component B1 18.0 parts by mass Product is clear at 20 ° C Propylene glycol 2.0 parts by mass Product is clear at 4 ° C Perfume oil 0.8 parts by mass
- Example 2 water 47.4 parts by mass dye 0.8 parts by mass Component A4 30.6 parts by mass Component B1 22.0 parts by mass Product is clear at 20 ° C Component B2 2.0 parts by mass Product is clear at 4 ° C Perfume oil 0.8 parts by mass
- Example 3 water 59.4 parts by mass dye 0.8 parts by mass Component A3 30.6 parts by mass Component B2 10.0 parts by mass Perfume oil 0.8 parts by mass CaCl 2 solution 1.0 parts by mass Product is clear at 20 ° C and at 4 ° C
- Example 4 water 51.4 parts by mass dye 0.8 parts by mass Component A4 30.6 parts by mass Component B2 6.0 parts by mass Hexylene glycol 12.0 parts by mass Perf
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Health & Medical Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Developing Agents For Electrophotography (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99100154A EP1018541A1 (fr) | 1999-01-07 | 1999-01-07 | Compositions adoucissantes et transparentes |
| AT99940160T ATE226621T1 (de) | 1999-01-07 | 1999-08-06 | Klare weichspülmittelformulierungen |
| DE59903208T DE59903208D1 (de) | 1999-01-07 | 1999-08-06 | Klare weichspülmittelformulierungen |
| PCT/EP1999/005692 WO2000040681A1 (fr) | 1999-01-07 | 1999-08-06 | Formulations claires d'assouplissants |
| PL99348776A PL348776A1 (en) | 1999-01-07 | 1999-08-06 | Clear softening agent formulations |
| EP99940160A EP1141189B1 (fr) | 1999-01-07 | 1999-08-06 | Formulations claires d'assouplissants |
| CA002359654A CA2359654C (fr) | 1999-01-07 | 1999-08-06 | Formulations claires d'assouplissants |
| US09/856,581 US6653275B1 (en) | 1999-01-07 | 1999-08-06 | Clear softening agent formulations |
| ES99940160T ES2188217T3 (es) | 1999-01-07 | 1999-08-06 | Formulaciones transparentes de agentes suavizantes. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99100154A EP1018541A1 (fr) | 1999-01-07 | 1999-01-07 | Compositions adoucissantes et transparentes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1018541A1 true EP1018541A1 (fr) | 2000-07-12 |
Family
ID=8237315
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP99100154A Withdrawn EP1018541A1 (fr) | 1999-01-07 | 1999-01-07 | Compositions adoucissantes et transparentes |
| EP99940160A Expired - Lifetime EP1141189B1 (fr) | 1999-01-07 | 1999-08-06 | Formulations claires d'assouplissants |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP99940160A Expired - Lifetime EP1141189B1 (fr) | 1999-01-07 | 1999-08-06 | Formulations claires d'assouplissants |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6653275B1 (fr) |
| EP (2) | EP1018541A1 (fr) |
| AT (1) | ATE226621T1 (fr) |
| CA (1) | CA2359654C (fr) |
| DE (1) | DE59903208D1 (fr) |
| ES (1) | ES2188217T3 (fr) |
| PL (1) | PL348776A1 (fr) |
| WO (1) | WO2000040681A1 (fr) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002086044A1 (fr) * | 2001-04-24 | 2002-10-31 | Henkel Kommanditgesellschaft Auf Aktien | Adoucissant transparent |
| US6966696B1 (en) | 1998-10-24 | 2005-11-22 | The Procter & Gamble Company | Methods for laundering delicate garments in a washing machine |
| US6995124B1 (en) | 1998-10-24 | 2006-02-07 | The Procter & Gamble Company | Methods for laundering delicate garments in a washing machine |
| US7185380B2 (en) | 1998-10-24 | 2007-03-06 | The Procter & Gamble Company | Methods for laundering delicate garments in a washing machine comprising a woven acrylic coated polyester garment container |
| WO2011123284A1 (fr) * | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Produit assouplissant thermostable |
| WO2011120822A1 (fr) | 2010-04-01 | 2011-10-06 | Evonik Degussa Gmbh | Composition active d'adoucissant pour étoffe |
| WO2011123733A1 (fr) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Produit assouplissant thermiquement stable |
| US8361953B2 (en) | 2008-02-08 | 2013-01-29 | Evonik Goldschmidt Corporation | Rinse aid compositions with improved characteristics |
| US8507425B2 (en) | 2010-06-29 | 2013-08-13 | Evonik Degussa Gmbh | Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making |
| US8563499B2 (en) | 2010-04-01 | 2013-10-22 | Evonik Degussa Gmbh | Fabric softener active composition |
| US8883713B2 (en) | 2012-01-30 | 2014-11-11 | Evonik Industries Ag | Fabric softener active composition |
| US8883712B2 (en) | 2010-04-28 | 2014-11-11 | Evonik Degussa Gmbh | Fabric softening composition |
| US9441187B2 (en) | 2012-05-07 | 2016-09-13 | Evonik Degussa Gmbh | Fabric softener active composition and method for making it |
| US10011806B2 (en) | 2013-11-05 | 2018-07-03 | Evonik Degussa Gmbh | Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester |
| US10113137B2 (en) | 2014-10-08 | 2018-10-30 | Evonik Degussa Gmbh | Fabric softener active composition |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2119821A1 (fr) | 2008-05-13 | 2009-11-18 | The Procter and Gamble Company | Procédé de traitement de textiles |
| US8188027B2 (en) | 2009-07-20 | 2012-05-29 | The Procter & Gamble Company | Liquid fabric enhancer composition comprising a di-hydrocarbyl complex |
| CN102834498B (zh) * | 2010-04-01 | 2014-04-30 | 宝洁公司 | 织物软化剂 |
| EP2997959B1 (fr) | 2014-09-22 | 2019-12-25 | Evonik Operations GmbH | Formulation contenant des esterquats a base d'isopropanolamine et de tetrahydroxypropylethylenediamine |
| EP2997958B1 (fr) | 2014-09-22 | 2021-03-10 | Evonik Operations GmbH | Émulsion contenant des esterquats liquides et polymères épaississants |
| WO2020061658A1 (fr) | 2018-09-28 | 2020-04-02 | L'oreal | Compositions de traitement des cheveux comportant un ester d'ammonium quaternaire |
| EP3911795B1 (fr) | 2019-01-17 | 2025-10-01 | ISP Investments LLC | Procédé de renforcement de fibres non kératiniques et leurs utilisations |
| JP7193405B2 (ja) * | 2019-04-01 | 2022-12-20 | 川研ファインケミカル株式会社 | 身体洗浄剤組成物 |
| JP2023098218A (ja) * | 2021-12-28 | 2023-07-10 | ライオン株式会社 | 透明液体柔軟剤組成物と別容器に充填された香料組成物とを備える繊維製品処理用物品およびその使用方法 |
| FR3145684A1 (fr) | 2023-02-10 | 2024-08-16 | L'oreal | Composition oxydante comportant un tensioactif cationique spécifique |
| FR3158637B3 (fr) | 2024-01-29 | 2026-02-13 | Oreal | Composition comprenant une émulsion de silicone particulière, un polysaccharide cationique, un alcool gras solide et un tensioactif cationique |
| FR3159744B3 (fr) | 2024-02-29 | 2026-03-13 | Oreal | Composition comprenant un tensioactif cationique spécifique, un polymère amphotère et un agent oxydant et/ou une teinture d’oxydation, et procédé de traitement des cheveux |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0082457A2 (fr) * | 1981-12-18 | 1983-06-29 | Hoechst Aktiengesellschaft | Agents concentrés adoucissant le linge |
| US5399272A (en) * | 1993-12-17 | 1995-03-21 | The Procter & Gamble Company | Clear or translucent, concentrated biodgradable quaternary ammonium fabric softener compositions |
| US5492636A (en) * | 1994-09-23 | 1996-02-20 | Quest International Fragrances Company | Clear concentrated fabric softener |
| US5545340A (en) * | 1993-03-01 | 1996-08-13 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11506810A (ja) * | 1995-07-11 | 1999-06-15 | ザ、プロクター、エンド、ギャンブル、カンパニー | 安定な濃縮布帛柔軟化組成物 |
| GB9526182D0 (en) * | 1995-12-21 | 1996-02-21 | Unilever Plc | Fabric softening composition |
| US5830845A (en) * | 1996-03-22 | 1998-11-03 | The Procter & Gamble Company | Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor |
-
1999
- 1999-01-07 EP EP99100154A patent/EP1018541A1/fr not_active Withdrawn
- 1999-08-06 CA CA002359654A patent/CA2359654C/fr not_active Expired - Fee Related
- 1999-08-06 WO PCT/EP1999/005692 patent/WO2000040681A1/fr not_active Ceased
- 1999-08-06 US US09/856,581 patent/US6653275B1/en not_active Expired - Fee Related
- 1999-08-06 EP EP99940160A patent/EP1141189B1/fr not_active Expired - Lifetime
- 1999-08-06 ES ES99940160T patent/ES2188217T3/es not_active Expired - Lifetime
- 1999-08-06 DE DE59903208T patent/DE59903208D1/de not_active Expired - Lifetime
- 1999-08-06 PL PL99348776A patent/PL348776A1/xx unknown
- 1999-08-06 AT AT99940160T patent/ATE226621T1/de not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0082457A2 (fr) * | 1981-12-18 | 1983-06-29 | Hoechst Aktiengesellschaft | Agents concentrés adoucissant le linge |
| US5545340A (en) * | 1993-03-01 | 1996-08-13 | The Procter & Gamble Company | Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains |
| US5399272A (en) * | 1993-12-17 | 1995-03-21 | The Procter & Gamble Company | Clear or translucent, concentrated biodgradable quaternary ammonium fabric softener compositions |
| US5492636A (en) * | 1994-09-23 | 1996-02-20 | Quest International Fragrances Company | Clear concentrated fabric softener |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6966696B1 (en) | 1998-10-24 | 2005-11-22 | The Procter & Gamble Company | Methods for laundering delicate garments in a washing machine |
| US6995124B1 (en) | 1998-10-24 | 2006-02-07 | The Procter & Gamble Company | Methods for laundering delicate garments in a washing machine |
| US7185380B2 (en) | 1998-10-24 | 2007-03-06 | The Procter & Gamble Company | Methods for laundering delicate garments in a washing machine comprising a woven acrylic coated polyester garment container |
| WO2002086044A1 (fr) * | 2001-04-24 | 2002-10-31 | Henkel Kommanditgesellschaft Auf Aktien | Adoucissant transparent |
| US8361953B2 (en) | 2008-02-08 | 2013-01-29 | Evonik Goldschmidt Corporation | Rinse aid compositions with improved characteristics |
| WO2011123284A1 (fr) * | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Produit assouplissant thermostable |
| RU2524954C2 (ru) * | 2010-04-01 | 2014-08-10 | Эвоник Дегусса Гмбх | Активная композиция мягчителя ткани |
| CN102834496A (zh) * | 2010-04-01 | 2012-12-19 | 赢创德固赛有限公司 | 织物柔软剂活性组合物 |
| WO2011120822A1 (fr) | 2010-04-01 | 2011-10-06 | Evonik Degussa Gmbh | Composition active d'adoucissant pour étoffe |
| WO2011123733A1 (fr) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Produit assouplissant thermiquement stable |
| US8563499B2 (en) | 2010-04-01 | 2013-10-22 | Evonik Degussa Gmbh | Fabric softener active composition |
| US8569224B2 (en) | 2010-04-01 | 2013-10-29 | Evonik Degussa Gmbh | Fabric softener active composition |
| CN102834496B (zh) * | 2010-04-01 | 2014-01-15 | 赢创德固赛有限公司 | 织物柔软剂活性组合物 |
| US8883712B2 (en) | 2010-04-28 | 2014-11-11 | Evonik Degussa Gmbh | Fabric softening composition |
| US8507425B2 (en) | 2010-06-29 | 2013-08-13 | Evonik Degussa Gmbh | Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making |
| US8883713B2 (en) | 2012-01-30 | 2014-11-11 | Evonik Industries Ag | Fabric softener active composition |
| US9441187B2 (en) | 2012-05-07 | 2016-09-13 | Evonik Degussa Gmbh | Fabric softener active composition and method for making it |
| US10011806B2 (en) | 2013-11-05 | 2018-07-03 | Evonik Degussa Gmbh | Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester |
| US10113137B2 (en) | 2014-10-08 | 2018-10-30 | Evonik Degussa Gmbh | Fabric softener active composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59903208D1 (de) | 2002-11-28 |
| EP1141189B1 (fr) | 2002-10-23 |
| ATE226621T1 (de) | 2002-11-15 |
| CA2359654A1 (fr) | 2000-07-13 |
| CA2359654C (fr) | 2007-05-29 |
| WO2000040681A1 (fr) | 2000-07-13 |
| EP1141189A1 (fr) | 2001-10-10 |
| US6653275B1 (en) | 2003-11-25 |
| ES2188217T3 (es) | 2003-06-16 |
| PL348776A1 (en) | 2002-06-17 |
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