DE1794068A1 - Preparations for treating textiles - Google Patents
Preparations for treating textilesInfo
- Publication number
- DE1794068A1 DE1794068A1 DE19681794068 DE1794068A DE1794068A1 DE 1794068 A1 DE1794068 A1 DE 1794068A1 DE 19681794068 DE19681794068 DE 19681794068 DE 1794068 A DE1794068 A DE 1794068A DE 1794068 A1 DE1794068 A1 DE 1794068A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- methyl
- carbon atoms
- hydrogen
- acid
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000004753 textile Substances 0.000 title claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- -1 alkyl radical Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 10
- 239000002979 fabric softener Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229940050176 methyl chloride Drugs 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 4
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- KQIXMZWXFFHRAQ-UHFFFAOYSA-N 1-(2-hydroxybutylamino)butan-2-ol Chemical compound CCC(O)CNCC(O)CC KQIXMZWXFFHRAQ-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
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical class ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000005406 washing 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
- C11D1/62—Quaternary ammonium compounds
-
- 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
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- 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
-
- 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
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (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)
Description
F A R B M ERKE HOECHST AG.FARB M ERKE HOECHST AG.
vormals Meister Lucius & Brüiiing I /94-068 formerly Master Lucius & Brüiiing I / 94-068
Frankfurt (Mai ή)*Ηö ch s t 29. August 196δ Dr.Gr/Mu Frankfurt (May ή) * Ηö ch st August 29, 196δ Dr. Gr / Mu
Anlage IAppendix I.
zur Patentanmeldung Fw 55&1to the patent application Fw 55 & 1
"Mittel zur Behandlung von Textilien""Agents for the treatment of textiles"
Zusatz zu Patent .. ... ... (Patentanmeldung P l6 19 058.2-43)Addition to patent ... ... ... (patent application P 16 19 058.2-43)
Gegenstand des Hauptpatentes- .... ... (PatentanmeldungSubject of the main patent .... ... (patent application
P l6 19 O58.2 - 43) ist die Verwendung von wäßrigen Zubereitungen, welche Verbindungen der allgemeinen Formel IP 16 19 O58.2 - 43) is the use of aqueous preparations, which compounds of the general formula I
CH9-CH-OCH 9 -CH-O
CH9-CH-O-(CrI-CH-O) -Rz.CH 9 -CH-O- (CrI-CH-O) -R e.g.
R_R_
enthalten, in der R für einen geradkettigen oder verzweigten Alkylrest mit 1 - 4 C-Atomen, R2 für einen geradkettigen oder verzweigten Alkyl- oder Alkoxy-methylenrest mit bis zu 8 C-Atomen, einen Benzylrest, Wasserstoff oder den Rest -CH2-COOY steht,, wobeiin which R stands for a straight-chain or branched alkyl radical with 1-4 carbon atoms, R 2 for a straight-chain or branched alkyl or alkoxymethylene radical with up to 8 carbon atoms, a benzyl radical, hydrogen or the radical -CH 2 -COOY stands ,, where
10 9 8 4 7/177910 9 8 4 7/1779
Fw 5581 aFw 5581 a
Y ein Alkalimetall oder Wasserstoff bedeutet, R und R. für Acylreste von gesättigten oder ungesättigten Monocarbonsäuren mit etwa 12 - 22 C-Atomen, R_ für den Methyl- oder Äthylrest:, Rg für Wasserstoff, den Methylrest oder den Äthylrest, X für das Anion einer organischen oder anorganischen Säure steht, und die Summe von m und η einen Wert von 0-12 besitzt, zur Behandlung von Textilien.Y is an alkali metal or hydrogen, R and R. for Acyl radicals of saturated or unsaturated monocarboxylic acids with about 12 - 22 carbon atoms, R_ for the methyl or ethyl radical :, Rg for hydrogen, the methyl radical or the ethyl radical, X for is the anion of an organic or inorganic acid, and the sum of m and η has a value of 0-12, for Treatment of textiles.
In weiterer Ausgestaltung des Hauptpatentes wurde nun gefunden, daß man mit gleichem Vorteil bei der Behandlung von Textilien, insbesondere als Weichspülmittel von Wäschestücken, wäßrige Zubereitungen von Verbindungen der allgemeinen Formel:In a further embodiment of the main patent, it has now been found that with the same advantage in the treatment of textiles, especially as a fabric softener for items of laundry, aqueous preparations of compounds of the general formula:
1111
R,R,
CH0-CH-O-(CH0-CH-O) -R, 3 2 m 3CH 0 -CH-O- (CH 0 -CH-O) -R, 3 2 m 3
verwenden kann, in der R. für einen geradkettigen oder verzweigten Alkylrest mit 1 - k C-Atomen, R0 für einen geradkettigen oder verzweigten Alkyl- oder Alkoxy-methylenrest mit bis zu 8 C-Atomen, einen Benzylrest, Wasserstoff oder den Rest - CH0COOY steht, wobei Y ein Alkalimetall oder Wasserstoff bedeutet, R„und R. für Acylreste von gesättigten oder ungesättigten Monocarbonsäure mit etwa 12 bis 22 C-Atomen, R für den Methyl- oder den Äthylrest, Rg für Wasserstoff, den Methyl- oder Äthylrest, X für das Anion einer organischen oder anorganischen Säure steht, und die Summe von m und η 0 - 12 bedeutet.can use, in which R. for a straight-chain or branched alkyl radical with 1 - k carbon atoms, R 0 for a straight-chain or branched alkyl or alkoxymethylene radical with up to 8 carbon atoms, a benzyl radical, hydrogen or the radical - CH 0 COOY, where Y is an alkali metal or hydrogen, R "and R. for acyl radicals of saturated or unsaturated monocarboxylic acid with about 12 to 22 carbon atoms, R for the methyl or the ethyl radical, Rg for hydrogen, the methyl or ethyl radical, X stands for the anion of an organic or inorganic acid, and the sum of m and η is 0-12.
Mit diesen Hilfsmitteln werden ebenfalls sehr gute weichmachende Effekte erhalten, ohne daß die Produkte die nachteilige, unzureichende Kältebeständigkeit der bekanntenWith these auxiliaries, very good softening effects are also obtained without the products having the disadvantageous, insufficient cold resistance of the known
10 9 8 47/177910 9 8 47/1779
- 3 - ■ ■ " ' 'Tv 55θΐ a- 3 - ■ ■ "'' Tv 55θΐ a
179Λ068179-068
Hilfsmittel besitzen.Own resources.
Die erfindungsgemäß zu verwendenden Verbindungen, die der o"bengenannten allgemeinen Formel entsprechen, erhält man beispielsweise durch Veresterung von N-substituierten Diisopropanolaminen oder Diisobutanolarainen sowie gegebenenfalls deren Anlagerungsprodukte mit bis zu etwa 12, vorzugsweise bis zu 4 Mol Athylenoxid, Propylenoxid und/oder Butylen- ©xid, die nachfolgend allgemein als Hydroxyalkylamine bezeichnet werden, mit 2 Mol einer. Carbonsäure und anschließende Umsetzung der Veresterungsprodukte mit einer anorganischen oder organischen Saure und/oder einem Quaternisierungsmittel. Bei der Herstellung der,erfindungsgemäß zu verwendenden Ver- ™ bindungen ist es auch möglich, für die Veresterung auf je 1 Mol des tertiären Hydroxyalkylamins weniger als 2 Mol der Carbonsäure einzusetzen. So werden beispielsweise bei Verwendung von 1,5 Mol der Carbonsäure pro Mol Aiain Gemische erhalten, die neben dem Monoester die der obengenannten Formel entsprechenden Bisester enthalten. Diese Gemische können in gleicher Weise eingesetzt werden, wie die reinen, der allgemeinen Formel entsprechenden Verbindungen,The compounds to be used according to the invention, which the o "correspond to the aforementioned general formula, one obtains for example by esterification of N-substituted ones Diisopropanolamines or diisobutanolaraines and optionally their addition products with up to about 12, preferably up to 4 moles of ethylene oxide, propylene oxide and / or butylene © xid, hereinafter generally referred to as hydroxyalkylamines be, with 2 moles one. Carboxylic acid and subsequent reaction of the esterification products with an inorganic one or organic acid and / or a quaternizing agent. In the production of the Ver ™ to be used according to the invention bonds, it is also possible for the esterification to less than 2 moles of the carboxylic acid for each 1 mole of the tertiary hydroxyalkylamine to use. For example, when using 1.5 moles of the carboxylic acid per mole of Aiain, mixtures are obtained which in addition to the monoester, those corresponding to the above formula Bisester included. These mixtures can be used in the same way are used, such as the pure compounds corresponding to the general formula,
Bei der Herstellung der erfindungsgemäß zu verwendenden Produkte können als N-substituierte Dialkanolamine beispielsweise li-Methyl?, N-Äthyl-, N-Butyl-dipropanolamin, N-Methyl-, N-Äthyl-, N-Butyl- Jj dibutanolamine sowie die Anlagerungsverbindungen dieser Amine mit bis zu etwa 12 Mol Propylenoxid bzw. Butylenoxid eingesetzt werden. .In the manufacture of the products to be used according to the invention can be used as N-substituted dialkanolamines, for example, li-methyl ?, N-ethyl-, N-butyl-dipropanolamine, N-methyl-, N-ethyl-, N-butyl- Jj dibutanolamine and the addition compounds of these amines used with up to about 12 moles of propylene oxide or butylene oxide will. .
FuV die Veresterung der Hydroxyalkylamine kommen aliphatisch^ etwa 12 - 22 C-Atome enthaltende Carbonsäuren in Betracht, Beispielsweise seien genannt Laurinsäure, Myristinsäure, Palmitinsäure, Stearinsäure, Ärachinsäure und Behensäure. Neben diesen^ aus natürlichen Fetten stammenden Säuren können auch synthetisch hergestellte Carbonsäuren mit entsprechender Kohlenstoffatoin-Anzahl verwendet werden. Selbstverständlich können auch Gemische d,er genannten Carbonsäuren eingesetzt werden. So ist beispiels-FuV the esterification of the hydroxyalkylamines come aliphatic ^ Carboxylic acids containing about 12-22 carbon atoms are suitable, for example lauric acid, myristic acid, palmitic acid, Stearic acid, arachidic acid and behenic acid. Besides these ^ Acids derived from natural fats can also be synthetic produced carboxylic acids with a corresponding number of carbon atoms be used. It is of course also possible to use mixtures of the carboxylic acids mentioned. So for example
109847/1779-109847 / 1779-
».-. -.:.-■ 8AD ORKaINAL».-. -.:.-■ 8AD ORKaINAL
- 4 - Fw 55Ö1 a- 4 - Fw 55Ö1 a
weise ein aus natürlichen Fetten gewonnenes Gemisch von Palmitin- und Stearinsäure besonders gut geeignet. In gleicher Weise können auch komplexe Carbonsäuregemische, wie sie z.B. bei der Hydrolyse von Talg oder Kokosfett anfallen, eingesetzt werden.wise a mixture of natural fats Palmitic and stearic acid are particularly suitable. In the same Complex carboxylic acid mixtures, such as those obtained from the hydrolysis of tallow or coconut oil, can also be used will.
Für die Salzbildung der veresterten Hydroxyalkylamine kommen beliebige anorganische oder organische Säuren in Frage, die mit den veresterten Hydroxyalkylaminen wasserlösliche oder in Wasser dispergierbare Salze bilden. Genannt seien beispielsweise: Salzsäure, Schwefelsäure, Phosphorsäure, Ameisensäure, und Essigsäure.Any inorganic or organic acids can be used for the salt formation of the esterified hydroxyalkylamines with the esterified hydroxyalkylamines water-soluble or in Form water dispersible salts. Examples include: hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, and acetic acid.
Vorzugsweise werden aber die veresterten Hydroxyalkylamine durch Umsetzung mit geeigneten Quaternisierungsmittel, wie Methylchlorid, Dimethyl- oder Diäthylsulfat, Benzylchlorid, Chloressigsäure in Form ihrer Alkalisalze oder den Chlormethyläthern von tnonofunktionellen Alkoholen in quaternäre Ammoniumverbindungen überführt. Die Quaternisierung kann in an sich bekannter Weise ggf. in Gegenwart eines organischen Lösungsmittels, wie z.B. eines niederen aliphatischen Alkohols vorgenommen werden. Eine Abtrennung dieses Lösungsmittels ist im allgemeinen nicht erforderlich, da seine Anwesenheit in dem Weichspülmittel meist nicht stört.Preferably, however, the esterified hydroxyalkylamines by reaction with suitable quaternizing agents, such as Methyl chloride, dimethyl or diethyl sulfate, benzyl chloride, Chloroacetic acid in the form of its alkali salts or the chloromethyl ethers of non-functional alcohols in quaternary ammonium compounds convicted. The quaternization can be carried out in a manner known per se, if appropriate in the presence of an organic solvent, such as a lower aliphatic alcohol. A separation of this solvent is generally not necessary, since its presence in the fabric softener is mostly not bother.
Die wäßrigen Zubereitungen der erfindungsgemäß zu verwendenden Verbindungen frieren zwar auch bei Temperaturen unter -5 C ein. Sie werden aber im Gegensatz zu den bekannten Produkten nach dem Auftauen überraschenderweise wieder in ihrer ursprünglichen Konsistenz zurück erhalten. Auch die weichmachenden Eigenscharten der Hilfsmittel bleiben in vollem Umfange erhalten. Es wurde ferner festgestellt, daß durch einen Zusatz der erfindungsgemäß zu verwendenden Verbindungen die oben beschriebene Erscheidung des ,Gelierens von wäßrigen Zubereitungen der bekannten kationaktivenThe aqueous preparations to be used according to the invention Compounds freeze even at temperatures below -5 C. In contrast to the well-known products, however, they are after the Thawing surprisingly returned to its original consistency. Also the softening properties the aids are retained in full. It was also found that by adding the invention to Compounds using the above-described decision of the gelling of aqueous preparations of the known cation-active
109 847/1779109 847/1779
- 5 — Fw 55Ö1 a- 5 - Fw 55Ö1 a
Weichspülmittel, beispielsweise von Distearyldimethylammoriiumchlorid, je nach der Zugabemenge ganz oder teilweise aufgehoben werden kann. Die erfindungsgemäß zu verwendenden Produkte können somit auch zusammen mit bekannten andern kationaktiven Weichspülmitteln eingesetzt werden. Der Anteil der erfindungsgemäß zu verwendenden Verbindungen in diesen Mischungen soll jedoch wenigstens etwa ^iO Gew./S, vorzugsweise wenigstens 60 Gew./6, bezogen auf die Gesamtwirksubstanz betragen.Fabric softener, such as distearyldimethylammoriium chloride, can be wholly or partially canceled depending on the amount added. The products to be used according to the invention can thus also be used together with known other cation-active Fabric softeners are used. The proportion of the invention Compounds to be used in these mixtures should, however, be at least about 10% by weight, preferably at least 60% by weight based on the total active substance.
Die erfindungsgemäß zu verwendenden kai;ionaktiveii Weichspülmittel ziehen im allgemeinen Substantiv auf die Paser auf. Für die Anwendung sind daher in den meisten Fällen sehr geringe Radkonzentrationen ausreichend. So werden beispielsweise bei einem Flotteiiverhältnis von 1 : 10 im allgemeinen Anivtendungskonzentraticrm von etwa 0,05 - etwa 0,5 g/l gewählt. " "The kai; ionaktivii fabric softeners to be used according to the invention generally draw nouns on the paser. For the Therefore, in most cases, very low wheel concentrations are sufficient. For example, one Liquor ratio of 1:10 in general application concentrate from about 0.05 to about 0.5 g / l. ""
Die Anwendung der srfindungsgemäßen Weichspülmittel erfolgt jeweils nach dem Waschprozeß. Die Mittel werden den üblichen Spülbädern, zweckmäßig dem letzten Spülbad zugesetzt. Die mit den erfindungsgemäßen Produkten behandelten Textilien fühlen sich geschmeidig und füllig an. Sie besitzen einen angenehmen weichen Griff.The fabric softeners according to the invention are used in each case after the washing process. The means are used in the usual rinsing baths, expediently added to the last rinsing bath. The textiles treated with the products according to the invention feel supple and plump. They are pleasantly soft to the touch.
109847/1779109847/1779
- 6 - Fw 5581 a- 6 - Fw 5581 a
Zur Demonstration des günstigen Viskositätsverhaltens und der Beständigkeit von wäßrigen Zubereitungen, welche die erfindungsgeraäß zu verwendenden Verbindungen (Beispiel A, B, C, D, E, und F) enthalten, werden diese Zubereitungen einem Gefriertest unterworfen, bei dem sie 6 mal abwechselnd jeweils 24 Stunden einer Temperatur von -10 C und +2OC ausgesetzt werden.To demonstrate the favorable viscosity behavior and the stability of aqueous preparations which the erfindungsgeraäß to be used compounds (Example A, B, C, D, E, and F) contain, these preparations are subjected to a freeze test, in which they alternate 6 times each 24 hours Temperatures of -10 C and + 2OC.
Zum Vergleich wird eine wäßrige Zubereitung eines bekannten Weichspülmittels (Beispiel G) in gleicher Weise behandelt.For comparison, an aqueous preparation of a known fabric softener is used (Example G) treated in the same way.
Sämtliche wäßrigen Zubereitungen stellen vor dem Test viskose, leicht gießbare Dispersionen dar.All aqueous preparations are viscous, slightly before the test pourable dispersions.
A) 5,0 Gew.So des niit Methylchlorid quaternisierten Bis-stearin-A) 5.0% by weight of the bis-stearin quaternized with methyl chloride
säureesters von N-Methyl-di-isopropanolamin 95,0 Gew.5ό ¥asseracid ester of N-methyl-di-isopropanolamine 95.0 Gew.5ό ¥ water
B) 1,0 Gew.SS Distearyl-dimethyl-ammoniumchloridB) 1.0 wt. SS distearyl dimethyl ammonium chloride
4,0 Gew./S des mit Methylchlorid quaternisierten Bis-stearin-4.0 wt / S of the bis-stearin quaternized with methyl chloride
säureesters von N-Methyl-di-isopropanolamin 95,0 Gew. 0A Wasseracid ester of N-methyl-di-isopropanolamine 95.0 wt. 0 A water
C) 2,0 Gew./S Distearyl-dimethyl-ammoniurnchloridC) 2.0 wt / S distearyl dimethyl ammonium chloride
3,0 Gew.% des mit Methylchlorid quaternisierten Bis-§tearin-3.0 wt.% Of the quaternized with methyl chloride, bis-§tearin-
säureesters von N-Methyl-di-isopropanolamin 95,0 Gew.% Wassersäureesters of N-methyl-di-isopropanolamine 95.0 wt.% water
D) 51O G.ev.% des mit Methylchlorid quaternisierten Bis-stearin-D) 51O G.ev.% of the bis-stearin quaternized with methyl chloride
säureesters von N-Methyl-di-isobutanolamin 95,0 Gew.Si Wasseracid esters of N-methyl-di-isobutanolamine 95.0 wt% water
E) 1,0 GeW.^i Distearyl-dimethylainmoniumchloridE) 1.0 wt. ^ I distearyl-dimethylainmonium chloride
4,0 Gew.>S des mit Methylchlorid quaternisierten Bis-staarinsäureesters von N-Methyl-di-isobutanolamin4.0 wt.> S of the bis-staaric acid ester quaternized with methyl chloride of N-methyl-di-isobutanolamine
10-9847/177910-9847 / 1779
- 7 - Fw 558i a- 7 - Fw 558i a
95,0 Gew.?o Wasser95.0% by weight of water
F) 2,0Gew.% Distearyl-dimethylammoniumchloridF) 2.0 wt. % Distearyl dimethyl ammonium chloride
3 »Ο Gew.?» des mit Methylchlorid quaternxsxerten. Bis-stearinsäureesters von N'-Methyl-di-isobutanolamin3 »Ο weight?» quaternxsxerten with methyl chloride. Bis-stearic acid ester of N'-methyl-di-isobutanolamine
G) 5»0 Gew./S Distearyl-dimethyl-ammoniumchlorid 95,0 Gew,?o WasserG) 5 »0 wt / S distearyl dimethyl ammonium chloride 95.0% by weight of water
Die Beurteilung der wäßrigen.Zubereitungen nach dem Test, ergibt: Das Muster G stellt eine weiche, nicht mehr gießbare, gallertige Paste dar; die Muster A1 B, C, D, E und F haben dagegen ihre ursprüngliche Beschaffenheit (viskos, gießbar) behalten.Assessment of the aqueous preparations after the test shows: Sample G is a soft, gelatinous paste that can no longer be poured; the samples A 1 B, C, D, E and F, however, have retained their original properties (viscous, pourable).
10984*7/177910984 * 7/1779
Claims (2)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19671619058 DE1619058A1 (en) | 1967-12-01 | 1967-12-01 | Preparations for treating textiles |
DE19681794068 DE1794068A1 (en) | 1967-12-01 | 1968-09-02 | Preparations for treating textiles |
CH1780468D CH1780468A4 (en) | 1967-12-01 | 1968-11-29 | |
CH496138D CH496138A (en) | 1967-12-01 | 1968-11-29 | Process for the finishing of textiles |
AT1163368A AT293332B (en) | 1967-12-01 | 1968-11-29 | Method for treating textiles |
FR1593921D FR1593921A (en) | 1967-12-01 | 1968-12-02 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19671619058 DE1619058A1 (en) | 1967-12-01 | 1967-12-01 | Preparations for treating textiles |
DEF0054180 | 1967-12-01 | ||
DE19681794068 DE1794068A1 (en) | 1967-12-01 | 1968-09-02 | Preparations for treating textiles |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1794068A1 true DE1794068A1 (en) | 1971-11-18 |
Family
ID=27180919
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19671619058 Pending DE1619058A1 (en) | 1967-12-01 | 1967-12-01 | Preparations for treating textiles |
DE19681794068 Pending DE1794068A1 (en) | 1967-12-01 | 1968-09-02 | Preparations for treating textiles |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19671619058 Pending DE1619058A1 (en) | 1967-12-01 | 1967-12-01 | Preparations for treating textiles |
Country Status (4)
Country | Link |
---|---|
AT (1) | AT293332B (en) |
CH (2) | CH1780468A4 (en) |
DE (2) | DE1619058A1 (en) |
FR (1) | FR1593921A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5296622A (en) * | 1990-05-17 | 1994-03-22 | Henkel Kommanditgesellschaft Auf Aktien | Quaternized esters |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE377349C (en) * | 1971-11-19 | 1983-09-12 | Berol Kemi Ab | WANT TO REDUCE THE MECHANICAL HALF STRENGTH AND / OR IMPROVE THE SOFTWARE OF CELLULOSA OR PAPER |
SE388222C (en) * | 1974-01-25 | 1985-09-09 | Berol Kemi Ab | SETS AND MEANS TO REDUCE THE MECHANICAL BALANCE SHEETS AND / OR IMPROVE THE SOFTNESS OF CELLULOSA OR PAPER |
DE2843659C3 (en) * | 1978-10-06 | 1984-05-24 | Hoechst Ag, 6230 Frankfurt | Use of quaternized ether amines as fiber finishes |
DE3608093A1 (en) * | 1986-03-12 | 1987-09-17 | Henkel Kgaa | MADE-UP TEXTILE SOFTENER CONCENTRATE |
GB2188653A (en) * | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
DE3638918A1 (en) * | 1986-11-14 | 1988-05-26 | Henkel Kgaa | QUARTER AMMONIUM COMPOUNDS, THEIR PRODUCTION AND USE AS A TEXTILE POST-TREATMENT AGENT |
US5128473A (en) * | 1991-02-01 | 1992-07-07 | Sherex Chemical Company, Inc. | Nitrogen-heterocyclic compounds and quaternary salts thereof |
US5182033A (en) * | 1991-06-14 | 1993-01-26 | Sherex Chemical Company, Inc. | Polyamide salts |
FR2693665B1 (en) † | 1992-07-17 | 1994-09-23 | Stepan Europe | Cationic surfactant compositions, based on mono or polyalkyl ester and / or amido ammonium, and methods for their preparation. |
US5734069A (en) * | 1992-08-05 | 1998-03-31 | Sherex Chemical Co., Inc. | Biodegradable amidoaminoesters |
DE4243550C1 (en) * | 1992-12-22 | 1994-06-01 | Henkel Kgaa | Fiber auxiliaries and their use |
DE4243701A1 (en) * | 1992-12-23 | 1994-06-30 | Henkel Kgaa | Aqueous textile softener dispersions |
US5916863A (en) | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
EP0890671A3 (en) * | 1997-07-10 | 2000-02-23 | Ciba SC Holding AG | Use of modified fatty amines for preventing deposition of low molecular weight by-products on textile materials |
US5919750A (en) * | 1997-07-24 | 1999-07-06 | Akzo Nobel Nv | Fabric softener composition |
DE19829787A1 (en) * | 1998-07-03 | 2000-01-05 | Henkel Kgaa | Finishing agent |
DE102016207063A1 (en) | 2016-04-26 | 2017-10-26 | Wacker Chemie Ag | Compositions containing carbamato-functionalized organopolysiloxanes and cationic surfactants |
-
1967
- 1967-12-01 DE DE19671619058 patent/DE1619058A1/en active Pending
-
1968
- 1968-09-02 DE DE19681794068 patent/DE1794068A1/en active Pending
- 1968-11-29 CH CH1780468D patent/CH1780468A4/xx unknown
- 1968-11-29 CH CH496138D patent/CH496138A/en not_active IP Right Cessation
- 1968-11-29 AT AT1163368A patent/AT293332B/en not_active IP Right Cessation
- 1968-12-02 FR FR1593921D patent/FR1593921A/fr not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5296622A (en) * | 1990-05-17 | 1994-03-22 | Henkel Kommanditgesellschaft Auf Aktien | Quaternized esters |
Also Published As
Publication number | Publication date |
---|---|
FR1593921A (en) | 1970-06-01 |
DE1619058A1 (en) | 1971-01-28 |
CH1780468A4 (en) | 1970-05-29 |
CH496138A (en) | 1970-09-15 |
AT293332B (en) | 1971-10-11 |
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