EP0184741A2 - Method of greasing leather and skins - Google Patents
Method of greasing leather and skins Download PDFInfo
- Publication number
- EP0184741A2 EP0184741A2 EP85115218A EP85115218A EP0184741A2 EP 0184741 A2 EP0184741 A2 EP 0184741A2 EP 85115218 A EP85115218 A EP 85115218A EP 85115218 A EP85115218 A EP 85115218A EP 0184741 A2 EP0184741 A2 EP 0184741A2
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- EP
- European Patent Office
- Prior art keywords
- fatty acid
- leather
- mol
- aminoalkylalkanolamine
- condensation
- 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.)
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- 239000010985 leather Substances 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 8
- 239000000194 fatty acid Substances 0.000 claims abstract description 26
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 25
- 229930195729 fatty acid Natural products 0.000 claims abstract description 25
- 239000002280 amphoteric surfactant Substances 0.000 claims abstract description 20
- 230000029936 alkylation Effects 0.000 claims abstract description 10
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000009833 condensation Methods 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 22
- 239000003921 oil Substances 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- -1 fatty acid esters Chemical class 0.000 claims description 5
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
- 239000008041 oiling agent Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical group NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 235000016068 Berberis vulgaris Nutrition 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 4
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000013830 Eruca Nutrition 0.000 description 2
- 241000801434 Eruca Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
- C14C9/02—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes using fatty or oily materials, e.g. fat liquoring
Definitions
- amphoteric surfactants are described for example in DE-OS 30 18 201. Then they are prepared by condensation of C 6 -C 22 fatty acids with the aminoalkylalkanolamides of the general formula given in a molar ratio of 1: 1 to 1: 1.5 and subsequent alkylation with vinylogenic compounds, the alkylation products, depending on the structure and extent of the reaction, if appropriate can have quaternized nitrogen atoms. Since the condensation products of fatty acid and aminoalkylalkanolamine generally contain a more or less high proportion of diamide, it is preferred Before the alkylation, an alkaline pretreatment is carried out, the diamide being converted into the monoamide. In the subsequent alkylation, this leads to improved amphoteric surfactants with, in particular, increased storage stability.
- saturated or unsaturated C 12 -C 22 fatty acids or corresponding fatty acid esters preference is given to using saturated or unsaturated C 12 -C 22 fatty acids or corresponding fatty acid esters. These can be present as pure components or preferably as mixtures of natural or synthetic origin. Examples of this are mixtures of coconut fatty acid, tallow fatty acid, trans-fatty acid, rapeseed oil fatty acid, and corresponding methyl esters or triglycerides.
- the amine component is preferably aminoethylethanolamine.
- the reaction is preferably carried out in the molar ratio of fatty acid or fatty acid residue: aminoalkylalkanolamine, such as 1: 1 to 1: 1.5.
- Particularly suitable vinylogous compounds are acrylic acid and methacrylic acid and their esters, such as methyl acrylate or methyl methacrylate.
- the amphoteric surfactants are formed by subsequent saponification of the alkylation products with aqueous sodium hydroxide solution.
- amphoteric surfactants described have high emulsion resistance to the hardness constituents of water and to alkali salts.
- leather and fur greasing with good greasing of the leather they result in a pleasantly soft, slimy and supple handle. Colorings are very brilliant with good levelness.
- Suede leather has a silky fiber with a nice writing effect.
- amphoteric surfactants can be used alone or in combination with conventional leather fatliquoring agents based on sulfated, sulfitized or chlorosulfonated oils or fats, as well as in combination with anionic and / or nonionic emulsifiers, such as alkyl benzene, fatty alcohol sulfates, Fettalkoholethosulfaten, Fettklarealkanolamidethosulfaten, sulfosuccinates, fatty alcohol and alkylphenol ethylene oxide adducts be used.
- the proportion of amphoteric surfactants can be 10-100% by weight, based on the fatty substance.
- amphoteric surfactants are leather and fur greasing agents which can be used without problems. They are used in the customary manner in the form of aqueous emulsions in an amount of 3-15% by weight of active substance, based on the shaved weight of the leather.
- amphoteric surfactant 97.2 g (0.25 mol) of the aminoamide were mixed in a three-necked flask with stirring and a thermometer at 90 ° C. with 4 g of 50% sodium hydroxide solution and 25 g of water and for 1 hour at 90-95 ° C. stirred to destroy diamide. Then 316.6 g of water and 18.0 g (0.25 mol) of acrylic acid were added and the mixture was stirred at 85 ° C. for 5 hours. A finely divided dispersion with 25% active substance was obtained.
- amphoteric surfactant 862.5 g (1.9 mol) of the aminoamide, 30.5 g of 50% sodium hydroxide solution, 2969.5 g of water and 137.5 g (1.91 mol) of acrylic acid were added in the order given below 1 specified, implemented. Here too, a finely dispersed product with 25% active substance was obtained.
- amphoteric surfactant 847 g (2.14 mol) of the aminoamide were dispersed in 2000 g of water and reacted with 153 g (2.13 mol) of acrylic acid by stirring at 80-90 ° C. for 8 hours.
- the product obtained was a viscous brown liquid with 33% active substance.
- amphoteric surfactant 1267 g (3.5 mol) of the aminoamide, 252 g (3.5 mol) of acrylic acid and 4500 g of water were reacted. A viscous brown liquid with 25% active substance was obtained.
- Example 3 50 parts of product Example 3 50 parts of sulfited ester oil 1: 1 to 1: 2 emulsify with water and apply with a brush. Soft, plump, light furs.
- the leather is very soft (softyl leather) with good fullness, uniform, brilliant aniline coloring.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Abstract
Verfahren zur Fettung von Leder und Pelzen unter Verwendung eines Amphotensids als Fettungsmittel, das hergestellt ist durch Kondensation von C6-C22-Fettsäuren oder entsprechenden Estern mit Aminoalkylalkanolaminen und nachfolgende Alkylierung mit vinylogen Verbindungen.Process for greasing leather and furs using an amphoteric surfactant as a greasing agent, which is produced by condensation of C6-C22 fatty acids or corresponding esters with aminoalkylalkanolamines and subsequent alkylation with vinylogenic compounds.
Description
Gegenstand der Erfindung ist ein Verfahren zur Fettung von Leder und Pelzen, dadurch gekennzeichnet, daß man als Fettungsmittel ein Amphotensid verwendet, das hergestellt ist durch Kondensation von C6-C22-Fettsäuren oder entsprechenden Fettsäureestern mit Aminoalkylalkanolaminen der allgemeinen Formel
- m = 2 - 6
- n = 2 oder 3
und nachfolgende Alkylierung durch Umsetzung mit vinylogen Verbindungen.The invention relates to a process for oiling leather and furs, characterized in that an amphoteric surfactant is used as the oiling agent, which is produced by condensation of C 6 -C 22 fatty acids or corresponding fatty acid esters with aminoalkylalkanolamines of the general formula
- m = 2-6
- n = 2 or 3
and subsequent alkylation by reaction with vinylogenic compounds.
Die Herstellung derartiger Amphotenside ist beispielsweise in der DE-OS 30 18 201 beschrieben. Danach werden diese hergestellt durch Kondensation von C6-C22-Fettsäuren mit den Aminoalkylalkanolamiden der angegebenen allgemeinen Formel im Molverhältnis 1 : 1 bis 1 : 1,5 und nachfolgende Alkylierung mit vinylogen Verbindungen, wobei die Alkylierungsprodukte je nach Struktur und Ausmaß der Umsetzung ggf. quaternierte Stickstoffatome aufweisen können. Da die Kondensationsprodukte aus Fettsäure und Aminoalkylalkanolamin in der Regel einen mehr oder weniger hohen Anteil an Diamid enthalten, wird vorzugsweise vor der Alkylierung eine alkalische Vorbehandlung durchgeführt, wobei das Diamid in das Monoamid übergeführt wird. Dies führt bei der anschließenden Alkylierung zu verbesserten Amphotensiden mit insbesondere erhöhter Lagerstabilität.The production of such amphoteric surfactants is described for example in DE-OS 30 18 201. Then they are prepared by condensation of C 6 -C 22 fatty acids with the aminoalkylalkanolamides of the general formula given in a molar ratio of 1: 1 to 1: 1.5 and subsequent alkylation with vinylogenic compounds, the alkylation products, depending on the structure and extent of the reaction, if appropriate can have quaternized nitrogen atoms. Since the condensation products of fatty acid and aminoalkylalkanolamine generally contain a more or less high proportion of diamide, it is preferred Before the alkylation, an alkaline pretreatment is carried out, the diamide being converted into the monoamide. In the subsequent alkylation, this leads to improved amphoteric surfactants with, in particular, increased storage stability.
Zur Herstellung der erfindungsgemäß zu verwendenden Amphotenside geht man vorzugsweise von gesättigten oder ungesättigten C12-C22-Fettsäuren oder entsprechenden Fettsäureestern aus. Diese können als reine Komponenten oder vorzugsweise als Gemische natürlichen oder synthetischen Ursprungs vorliegen. Beispiele hierfür sind Kokosfettsäure-, Talgfettsäure-, Tranfettsäure-, Rübölfettsäuregemische, sowie entsprechende Methylester oder Triglyceride. Die Aminkomponente ist vorzugsweise Aminoethylethanolamin. Die Umsetzung erfolgt vorzugsweise im Molverhältnis von Fettsäure bzw. Fettsäurerest : Aminoalkylalkanolamin wie 1 : 1 bis 1 : 1,5. Als vinyloge Verbindungen eignen sich insbesondere Acrylsäure und Methacrylsäure sowie deren Ester, wie Acrylsäuremethylester oder Methacrylsäureethylester. In letzterem Falle entstehen die Amphotenside durch nachfolgende Verseifung der Alkylierungsprodukte mit wäßriger Natronlauge.To produce the amphoteric surfactants to be used according to the invention, preference is given to using saturated or unsaturated C 12 -C 22 fatty acids or corresponding fatty acid esters. These can be present as pure components or preferably as mixtures of natural or synthetic origin. Examples of this are mixtures of coconut fatty acid, tallow fatty acid, trans-fatty acid, rapeseed oil fatty acid, and corresponding methyl esters or triglycerides. The amine component is preferably aminoethylethanolamine. The reaction is preferably carried out in the molar ratio of fatty acid or fatty acid residue: aminoalkylalkanolamine, such as 1: 1 to 1: 1.5. Particularly suitable vinylogous compounds are acrylic acid and methacrylic acid and their esters, such as methyl acrylate or methyl methacrylate. In the latter case, the amphoteric surfactants are formed by subsequent saponification of the alkylation products with aqueous sodium hydroxide solution.
Die beschriebenen Amphotenside weisen eine hohe Emulsionsbeständigkeit gegenüber den Härtebildnern des Wassers sowie gegenüber Alkalisalzen auf. Sie ergeben bei der Leder- und Pelzfettung bei guter Durchfettung der Leder einen angenehm weichen, schmalzigen und geschmeidigen Griff. Färbungen fallen bei guter Egalität sehr brillant aus. Bei Veloursledern wird eine seidige Faser mit einem schönen Schreibeffekt erhalten.The amphoteric surfactants described have high emulsion resistance to the hardness constituents of water and to alkali salts. In the case of leather and fur greasing with good greasing of the leather, they result in a pleasantly soft, slimy and supple handle. Colorings are very brilliant with good levelness. Suede leather has a silky fiber with a nice writing effect.
Die Amphotenside können allein oder in Kombination mit üblichen Lederfettungsmitteln auf der Basis von sulfatierten, sulfitierten oder sulfochlorierten Ölen oder Fetten sowie in Kombination mit anionischen und/oder nichtionischen Emulgatoren, wie Alkylbenzolsulfonaten, Fettalkoholsulfaten, Fettalkoholethosulfaten, Fettsäurealkanolamidethosulfaten, Sulfosuccinaten, Fettalkohol-und Alkylphenol-Ethylenoxidaddukten eingesetzt werden. Der Anteil der Amphotenside kann 10 - 100 Gew.-%, bezogen auf fettende Substanz, betragen. Wegen des amphoteren Charakters der beanspruchten Produkte sind auch Kombinationen mit kationischen Fettungsmitteln bzw. Emulgatoren, wie z. B. Dimethyldistearylammoniumchlorid möglich. Die Amphotenside stellen problemlos anzuwendende Leder- und Pelzfettungsmittel dar. Sie werden in üblicher Weise in Form wäßriger Emulsionen in einer Menge von 3 - 15 Gew.-% Aktivsubstanz, bezogen auf das Falzgewicht des Leders, angewendet.The amphoteric surfactants can be used alone or in combination with conventional leather fatliquoring agents based on sulfated, sulfitized or chlorosulfonated oils or fats, as well as in combination with anionic and / or nonionic emulsifiers, such as alkyl benzene, fatty alcohol sulfates, Fettalkoholethosulfaten, Fettsäurealkanolamidethosulfaten, sulfosuccinates, fatty alcohol and alkylphenol ethylene oxide adducts be used. The proportion of amphoteric surfactants can be 10-100% by weight, based on the fatty substance. Because of the amphoteric character of the claimed products, combinations with cationic fatliquoring agents or emulsifiers, such as. B. Dimethyldistearylammoniumchlorid possible. The amphoteric surfactants are leather and fur greasing agents which can be used without problems. They are used in the customary manner in the form of aqueous emulsions in an amount of 3-15% by weight of active substance, based on the shaved weight of the leather.
2117,0 g (8,0 Mol) Talgfettsäure wurden in Gegenwart von 3 g 50%iger unterphosphoriger Säure (zwecks Farbstabilisierung) mit 915 g (8,8 Mol) Aminoethylethanolamin in einem Dreihalskolben, versehen mit Rührer, Thermometer, Stickstoffspülung und Destillationsaufsatz, unter langsamen Aufheizen auf 200 °C zur Reaktion gebracht; bei ca. 151 °C setzte die Wasserabspaltung ein. Nach 1 Std. Rühren bei 200 °C unter Normaldruck sowie einer weiteren Stunde bei 20 mbar wurden als Rückstand erhalten: 2626 g Aminoamid (talgartige, gelbliche Masse der Aminzahl 144)2117.0 g (8.0 mol) of tallow fatty acid were in the presence of 3 g of 50% hypophosphorous acid (for the purpose of color stabilization) with 915 g (8.8 mol) of aminoethylethanolamine in a three-necked flask equipped with a stirrer, thermometer, nitrogen purge and distillation attachment, reacted with slow heating to 200 ° C; at approx. 151 ° C the water split off. After stirring for 1 hour at 200 ° C. under normal pressure and for a further hour at 20 mbar, the residue obtained: 2626 g of aminoamide (tallow-like, yellowish mass of the amine number 144)
Zur Herstellung des Amphotensids wurden 97,2 g (0,25 Mol) des Aminoamids in einem Dreihalskolben mit Rührung und Thermometer bei 90 °C mit 4 g 50%iger Natronlauge und 25 g Wasser versetzt und 1 Std. bei 90 - 95 °C zur Zerstörung von Diamid gerührt. Dann wurden 316,6 g Wasser und 18,0 g (0,25 Mol) Acrylsäure hinzugefügt und das Gemisch 5 Std. bei 85 °C nachgerührt. Es wurde eine feinteilige Dispersion mit 25 % Aktivsubstanz erhalten.To produce the amphoteric surfactant, 97.2 g (0.25 mol) of the aminoamide were mixed in a three-necked flask with stirring and a thermometer at 90 ° C. with 4 g of 50% sodium hydroxide solution and 25 g of water and for 1 hour at 90-95 ° C. stirred to destroy diamide. Then 316.6 g of water and 18.0 g (0.25 mol) of acrylic acid were added and the mixture was stirred at 85 ° C. for 5 hours. A finely divided dispersion with 25% active substance was obtained.
2191 g (7,0 Mol) Rübölfettsäure, erucareich, 800,8 g (7,7 Mol) Aminoethylethanolamin und 3,0 g 50%ige unterphosphorige Säure wurden wie unter 1 angegeben zum Aminoamid umgesetzt.2191 g (7.0 mol) of beet oil fatty acid, rich in eruca, 800.8 g (7.7 mol) of aminoethylethanolamine and 3.0 g of 50% hypophosphorous acid were converted to the aminoamide as indicated under 1.
Ausbeute: 2635 g eines viskosen, braunen Öls, Aminzahl 124.Yield: 2635 g of a viscous, brown oil, amine number 124.
Zur Herstellung des Amphotensids wurden 862,5 g (1,9 Mol) des Aminoamids, 30,5 g 50%ige Natronlauge, 2969,5 g Wasser und 137,5 g (1,91 Mol) Acrylsäure in der angeführten Reihenfolge wie unter 1 angegeben, umgesetzt. Auch hier wurde ein feindisperses Produkt mit 25 % Aktivsubstanz erhalten.To prepare the amphoteric surfactant, 862.5 g (1.9 mol) of the aminoamide, 30.5 g of 50% sodium hydroxide solution, 2969.5 g of water and 137.5 g (1.91 mol) of acrylic acid were added in the order given below 1 specified, implemented. Here too, a finely dispersed product with 25% active substance was obtained.
1109 g (1,25 Mol) Rüböl, erucasäurearm,und 391 g (3,75 Mol) Aminoethylethanolamin wurden in einem Dreihalskolben, versehen mit Rührer, Thermometer, StickstoffSpülung und Destillationsaufsatz in Gegenwart von 22,5 g 30%iger Natriummethylatlösung in 3 Std. auf 180 °C aufgeheizt, dann 3 Std. bei 180 °C gerührt. Das rohe Umsetzungsprodukt (Aminoamid) war ein bräunliches Ö1, Aminzahl 142.1109 g (1.25 mol) of beet oil, low erucic acid, and 391 g (3.75 mol) of aminoethylethanolamine were in a three-necked flask equipped with a stirrer, thermometer, nitrogen purge and distillation head in the presence of 22.5 g of 30% sodium methylate solution in 3 hours heated to 180 ° C., then stirred at 180 ° C. for 3 hours. The crude reaction product (aminoamide) was a brownish oil, amine number 142.
Zur Herstellung des Amphotensids wurden 847 g (2,14 Mol) des Aminoamids in 2000 g Wasser dispergiert und mit 153 g (2,13 Mol) Acrylsäure durch 8 Std. Rühren bei 80 - 90 °C zur Umsetzung gebracht. Das erhaltene Produkt war eine viskose braune Flüssigkeit mit 33 % Aktivsubstanz.To prepare the amphoteric surfactant, 847 g (2.14 mol) of the aminoamide were dispersed in 2000 g of water and reacted with 153 g (2.13 mol) of acrylic acid by stirring at 80-90 ° C. for 8 hours. The product obtained was a viscous brown liquid with 33% active substance.
2014 g (7 Mol) Tranfettsäure (J. Z. 117), 800,8 g (7,7 Mol) Aminoethylethanolamin und 3,0 g unterphosphorige Säure wurden wie unter 1 angegeben zum Aminoamid umgesetzt.2014 g (7 mol) of trans fatty acid (J. Z. 117), 800.8 g (7.7 mol) of aminoethylethanolamine and 3.0 g of hypophosphorous acid were converted to the aminoamide as indicated under 1.
Ausbeute: 2450 g braunes Ö1, Aminzahl 155.Yield: 2450 g of brown oil, amine number 155.
Zur Herstellung des Amphotensids wurden 1267 g (3,5 Mol) des Aminoamids, 252 g (3,5 Mol) Acrylsäure und 4500 g Wasser umgesetzt. Es wurde eine viskose braune Flüssigkeit mit 25 % Aktivsubstanz erhalten.To prepare the amphoteric surfactant, 1267 g (3.5 mol) of the aminoamide, 252 g (3.5 mol) of acrylic acid and 4500 g of water were reacted. A viscous brown liquid with 25% active substance was obtained.
412,0 g (2,0 Mol) Kokosölfettsäure wurden in Gegenwart von 0,5 ml 50%iger unterphosphoriger Säure mit 228,8 g (2,2 Mol) Aminoethylethanolamin in einem Dreihalskolben, versehen mit Rührer, Thermometer, Stickstoffspülung und Destillationsaufsatz unter langsamem Aufheizen auf ca. 200 °C zur Reaktion gebracht. Nach lstündigem Rühren bei 200 °C hatten sich 46,5 ml Reaktionswasser abgeschieden. Es wurde eine weitere Stunde bei ca. 20 mbar gerührt, wobei weiteres Reaktionswasser sowie überschüssiges Amin abdestillierten (insgesamt 47 g). Als Rückstand verblieben 540,5 g eines schwach gelben, bei Raumtemperatur langsam erstarrenden Öls, Aminzahl 180.412.0 g (2.0 mol) of coconut oil fatty acid were in the presence of 0.5 ml of 50% hypophosphorous acid with 228.8 g (2.2 mol) of aminoethylethanolamine in a three-necked flask equipped with a stirrer, thermometer, nitrogen purge and distillation head brought to slow reaction to about 200 ° C to react. After stirring for 1 hour at 200 ° C., 46.5 ml of water of reaction had separated out. The mixture was stirred for a further hour at about 20 mbar, further water of reaction and excess amine distilling off (a total of 47 g). 540.5 g of a pale yellow oil which slowly solidified at room temperature, amine number 180, remained as the residue.
a) Zur Herstellung des Amphotensids wurden 311,8 g (1 Mol) des Aminoamids, 16,2 g 50%ige Natronlauge, 599,0 g Wasser und 72,0 g (1 Mol) Acrylsäure in der angegebenen Reihenfolge wie unter 1 angegeben, umgesetzt. Das erhaltene Produkt war eine viskose, klare Flüssigkeit mit ca. 40 % Aktivsubstanz.a) To prepare the amphoteric surfactant, 311.8 g (1 mol) of the aminoamide, 16.2 g of 50% sodium hydroxide solution, 599.0 g of water and 72.0 g (1 mol) of acrylic acid were in the order given as indicated under 1 , implemented. The product obtained was a viscous, clear liquid with about 40% active substance.
b) Eine weitere Umsetzung wurde wie unter a) angegeben durchgeführt, jedoch wurden statt 72,0 g Acrylsäure 86 g (1 Mol) Acrylsäuremethylester eingesetzt. Nach 4stündigem Rühren bei 70 "C wurde nicht umgesetzter Acrylsäuremethylester im Vakuum abgezogen und das rohe Umsetzungsprodukt durch Zugabe von 40 g NaOH und 650 ml Wasser durch 4stündiges Erwärmen auf 80 "C verseift. Es wurde eine viskose, klare Flüssigkeit mit ca. 40 % Aktivsubstanz erhalten.b) A further reaction was carried out as indicated under a), but instead of 72.0 g of acrylic acid, 86 g (1 mol) of methyl acrylate were used. After stirring for 4 hours at 70 ° C., unreacted methyl acrylate was removed in vacuo and the crude reaction product was saponified by adding 40 g of NaOH and 650 ml of water by heating to 80 ° C. for 4 hours. A viscous, clear liquid with about 40% active substance was obtained.
Material: wet-blue Gew.-% auf Falzgewicht
50 Teile Produkt Beispiel 3 50 Teile sulfitiertes Esteröl 1 : 1 bis 1 : 2 mit Wasser emulgieren und mit der Bürste auftragen. Weiche, mollige, leichte Pelze.50 parts of product Example 3 50 parts of sulfited ester oil 1: 1 to 1: 2 emulsify with water and apply with a brush. Soft, plump, light furs.
Material: wet-blue Gew.-% auf Falzgewicht
Material: Crustleder Gew.-% auf Trockengewicht
Material: wet-blueMaterial: wet blue
Gew.-% auf Falzgewicht
Das Leder ist sehr weich (Softyleder) mit guter Fülle, gleichmäßiger, brillanter Anilinfärbung.The leather is very soft (softyl leather) with good fullness, uniform, brilliant aniline coloring.
Claims (5)
und nachfolgende Alkylierung durch Umsetzung mit vinylogen Verbindungen.1. A process for oiling leather and furs, characterized in that an amphoteric surfactant is used as the oiling agent, which is prepared by condensation of C 6 -C 22 fatty acids or corresponding fatty acid esters with aminoalkylalkanolamines of the general formula
and subsequent alkylation by reaction with vinylogenic compounds.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19843444864 DE3444864A1 (en) | 1984-12-08 | 1984-12-08 | METHOD FOR GREATING LEATHER AND FURS |
DE3444864 | 1984-12-08 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0184741A2 true EP0184741A2 (en) | 1986-06-18 |
EP0184741A3 EP0184741A3 (en) | 1987-05-13 |
EP0184741B1 EP0184741B1 (en) | 1989-07-26 |
Family
ID=6252278
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85115218A Expired EP0184741B1 (en) | 1984-12-08 | 1985-11-30 | Method of greasing leather and skins |
Country Status (5)
Country | Link |
---|---|
US (1) | US4729767A (en) |
EP (1) | EP0184741B1 (en) |
BR (1) | BR8506116A (en) |
DE (2) | DE3444864A1 (en) |
ES (1) | ES8609486A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0372746A2 (en) * | 1988-12-02 | 1990-06-13 | Rohm And Haas Company | The use of selected amphiphilic copolymers in the treatment of leather |
WO1995025816A1 (en) * | 1994-03-23 | 1995-09-28 | Henkel Kommanditgesellschaft Auf Aktien | Use of alkylene diamine tetrapropionic acids for the oiling off of leathers |
WO1995027800A1 (en) * | 1994-04-12 | 1995-10-19 | Allied Colloids Limited | Leather softening |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5330537A (en) * | 1990-06-07 | 1994-07-19 | Rohm And Haas Company | Leather treatment selected amphiphilic copolymer |
DE4435398A1 (en) * | 1994-10-04 | 1996-04-11 | Henkel Kgaa | Process for the production of leather greasing agents |
US5630847A (en) * | 1995-03-30 | 1997-05-20 | The Procter & Gamble Company | Perfumable dry cleaning and spot removal process |
PL323618A1 (en) * | 1996-12-20 | 1998-06-22 | Tfl Ledertechnik Gmbh & Co Kg | Hide processing compositions |
GB0118156D0 (en) * | 2001-07-25 | 2001-09-19 | Pittards Plc | Leather production |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR962038A (en) * | 1950-05-27 | |||
GB773825A (en) * | 1954-02-18 | 1957-05-01 | Nopco Chem Co | Fat-liquoring compositions |
DE2219806A1 (en) * | 1972-04-22 | 1973-10-31 | Basf Ag | Oiling leather and pelts -with acylaminocarboxylic acid - (salts) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB599261A (en) * | 1944-05-18 | 1948-03-09 | Nat Oil Prod Co | Improvements in or relating to the fat liquoring of hides and skins |
US2974000A (en) * | 1956-10-05 | 1961-03-07 | Nopco Chem Co | Fat-liquoring process |
DE3018201A1 (en) * | 1980-05-13 | 1981-11-19 | Henkel KGaA, 4000 Düsseldorf | METHOD FOR REFINING THE RAW CONDENSATION PRODUCT FROM AMINOALKYLALKANOLAMINES AND FATTY ACIDS, AND IF NECESSARY FOR THE FOLLOWING DETERMINATION OF AMPHOTENSIDE WITH INCREASED STORAGE STABILITY |
-
1984
- 1984-12-08 DE DE19843444864 patent/DE3444864A1/en not_active Withdrawn
-
1985
- 1985-11-30 EP EP85115218A patent/EP0184741B1/en not_active Expired
- 1985-11-30 DE DE8585115218T patent/DE3571835D1/en not_active Expired
- 1985-12-06 ES ES549667A patent/ES8609486A1/en not_active Expired
- 1985-12-06 BR BR8506116A patent/BR8506116A/en not_active IP Right Cessation
- 1985-12-09 US US06/806,740 patent/US4729767A/en not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR962038A (en) * | 1950-05-27 | |||
GB773825A (en) * | 1954-02-18 | 1957-05-01 | Nopco Chem Co | Fat-liquoring compositions |
DE2219806A1 (en) * | 1972-04-22 | 1973-10-31 | Basf Ag | Oiling leather and pelts -with acylaminocarboxylic acid - (salts) |
Non-Patent Citations (1)
Title |
---|
Römpps Chemielexikon, Seite 3817 (1977) * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0372746A2 (en) * | 1988-12-02 | 1990-06-13 | Rohm And Haas Company | The use of selected amphiphilic copolymers in the treatment of leather |
EP0372746A3 (en) * | 1988-12-02 | 1992-04-22 | Rohm And Haas Company | The use of selected amphiphilic copolymers in the treatment of leather |
EP0579267A1 (en) * | 1988-12-02 | 1994-01-19 | Rohm And Haas Company | Leather treatment with selected amphiphilic copolymers |
WO1995025816A1 (en) * | 1994-03-23 | 1995-09-28 | Henkel Kommanditgesellschaft Auf Aktien | Use of alkylene diamine tetrapropionic acids for the oiling off of leathers |
WO1995027800A1 (en) * | 1994-04-12 | 1995-10-19 | Allied Colloids Limited | Leather softening |
US5603733A (en) * | 1994-04-12 | 1997-02-18 | Allied Colloids Limited | Leather softening |
Also Published As
Publication number | Publication date |
---|---|
US4729767A (en) | 1988-03-08 |
ES549667A0 (en) | 1986-09-01 |
BR8506116A (en) | 1986-08-26 |
DE3444864A1 (en) | 1986-06-12 |
DE3571835D1 (en) | 1989-08-31 |
EP0184741B1 (en) | 1989-07-26 |
ES8609486A1 (en) | 1986-09-01 |
EP0184741A3 (en) | 1987-05-13 |
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