EP0470102B1 - Use of Triacetin in Textile Gliding Agents - Google Patents
Use of Triacetin in Textile Gliding Agents Download PDFInfo
- Publication number
- EP0470102B1 EP0470102B1 EP90906172A EP90906172A EP0470102B1 EP 0470102 B1 EP0470102 B1 EP 0470102B1 EP 90906172 A EP90906172 A EP 90906172A EP 90906172 A EP90906172 A EP 90906172A EP 0470102 B1 EP0470102 B1 EP 0470102B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- triacetin
- textile
- weight
- agents
- fiber
- 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.)
- Expired - Lifetime
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- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000001087 glyceryl triacetate Substances 0.000 title claims abstract description 26
- 235000013773 glyceryl triacetate Nutrition 0.000 title claims abstract description 26
- 239000004753 textile Substances 0.000 title claims abstract description 26
- 229960002622 triacetin Drugs 0.000 title claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 22
- 239000000314 lubricant Substances 0.000 claims description 27
- 238000009499 grossing Methods 0.000 claims description 14
- 239000002216 antistatic agent Substances 0.000 claims description 11
- 239000003995 emulsifying agent Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 26
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- -1 alkyl glycols Chemical class 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002657 fibrous material Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- AFSHUZFNMVJNKX-UHFFFAOYSA-N 1,2-di-(9Z-octadecenoyl)glycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCC=CCCCCCCCC AFSHUZFNMVJNKX-UHFFFAOYSA-N 0.000 description 1
- AFSHUZFNMVJNKX-LLWMBOQKSA-N 1,2-dioleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC\C=C/CCCCCCCC AFSHUZFNMVJNKX-LLWMBOQKSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229920003299 Eltex® Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007786 electrostatic charging Methods 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229940037626 isobutyl stearate Drugs 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CPXCDEMFNPKOEF-UHFFFAOYSA-N methyl 3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1 CPXCDEMFNPKOEF-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Classifications
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- 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
- D06M13/10—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 oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- D06M13/2243—Mono-, di-, or triglycerides
-
- 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
- D06M13/10—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 oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- 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
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Definitions
- the invention relates to the use of triacetin in textile lubricants and a method for reducing the viscosity of textile lubricants.
- Melting should ensure optimal yarn production from loose or upstream fiber materials and must therefore in particular improve the adhesive and sliding properties of synthetic staple fibers, natural fibers and / or mixtures of natural and synthetic fiber materials (Chwala / Anger: "Handbuch der Textilhilhilstoff", chapter 3.7, publisher Chemistry, Weinheim 1977).
- Fiber preparations and lubricants which contain smoothing agents, antistatic agents and / or emulsifiers as their main active substances, are solid, pasty or viscous. Since preference is given to liquid fiber preparations and slicing for processing reasons, fiber preparations and slicing are converted into a liquid form using adjusting agents (diluents). However, the higher the leveling agent content required for the desired viscosity, the more the effectiveness, in particular the effectiveness of the lubricant, of the preparations and lubricants decreases. Glycols and / or alkyl glycols are usually used as adjusting agents, but their toxicology is not harmless.
- the object on which the invention is based was therefore the development of fiber preparations and lubricants which have a viscosity suitable for the application, which prevent the tendency of fiber preparations and lubricants to curl, but at least considerably reduce them, and give the fiber materials excellent smoothness properties and very good antistatic properties. Furthermore the fiber preparations and lubricants to be developed are subject to the condition of being physiologically harmless.
- the invention accordingly relates to the use of triacetin in textile lubricants based on smoothing agents, antistatic agents and / or emulsifiers.
- Another object of the invention is a method for reducing the viscosity of textile lubricants, which is characterized in that textile lubricants based on smoothing agents, antistatic agents and / or emulsifiers are mixed with triacetin.
- textile lubricant includes in particular fiber preparations and finishing agents, for example smelting ("Ullmanns Encyclopedia of Industrial Chemistry", volume 23, pages 5-6, Verlag Chemie Weinheim 1983).
- the triacetin to be used according to the invention can be prepared in a manner known per se, for example according to EP-A-33 929, by reacting glycerol with acetic acid and acetic anhydride, if appropriate in the presence of catalysts.
- the textile lubricants can be used as smoothing agents, for example mineral oils, fatty acid esters with 8 to 22 carbon atoms in the fat residue and 1 to 22 carbon atoms in the alcohol residue, for example methyl palmitate, isobutyl stearate and / or 2-ethylhexyl tallow fatty acid, polyol carboxylic acid esters, for example coconut fatty acid esters of glycerol and / or alkoxylated glycerols, silicones, for example dimethylpolysiloxane and / or polyalkylene glycols, for example ethylene oxide / propylene oxide mixed polymers with average molecular weights between 600 and 6,000 (chemical fibers / textile industry 1977 335) included.
- mineral oils for example mineral oils, fatty acid esters with 8 to 22 carbon atoms in the fat residue and 1 to 22 carbon atoms in the alcohol residue, for example methyl palmitate, isobutyl stearate and / or 2-ethyl
- Suitable emulsifiers, wetting agents and / or antistatic agents are anionic, cationic and / or nonionic surfactants, such as mono- and / or diglycerides, for example glycerol mono- and / or glycerol dioleate, alkoxylated, preferably ethoxylated and / or propoxylated fats, oils, fatty alcohols 8 to 24 carbon atoms and / or C8 ⁇ 18 alkylphenols, for example castor oil with 25 moles of ethylene oxide (EO) and / or C16 ⁇ 18 fatty alcohol with 8 moles of propylene oxide and 6 moles of EO, if desired alkoxylated C8 ⁇ 24 fatty acid mono- and / or -diethanolamides, for example optionally ethoxylated oleic acid mono- and / or -diethanolamide, tallow fatty acid mono- and / or -diethanolamide and / or coconut fatty acid mono-
- smoothing agents In this exemplary list of smoothing agents, emulsifiers, antistatic agents and / or wetting agents, it must be taken into account that a large number of the substances mentioned have not only one function, but several functions: for example, a smoothing agent can simultaneously act as an antistatic agent and / or as an emulsifier.
- the optional triacetin-containing textile lubricants contain thread closure agents, e.g. B. polyacrylates, fatty acid sarcosides and / or copolymers with Maleic anhydride (Melliand Textile Reports 1977 , 197) and / or polyurethanes according to DE-A-38 30 468, pH regulators, for example C1 ⁇ 4-carboxylic acids and / or C1 ⁇ 4-hydroxycarboxylic acids, such as acetic acid and / or glycolic acid, alkali metal hydroxides , such as potassium hydroxide and / or amines such as triethanolamine, bactericides and / or anti-corrosion agents.
- thread closure agents e.g. B. polyacrylates, fatty acid sarcosides and / or copolymers with Maleic anhydride (Melliand Textile Reports 1977 , 197) and / or polyurethanes according to DE-A-38 30 468
- pH regulators for example C1 ⁇
- Triacetin-containing melts are usually sprayed onto synthetic staple fibers, natural fibers or mixtures of natural and synthetic fiber materials.
- the quantity of melt applied in undiluted form or in a mixture with water is between 0.1 and 3% by weight, based on the weight of the fiber materials.
- Triacetin-containing fiber preparations are applied in a known manner immediately after the capillaries have emerged from the spinneret.
- the fiber preparations which have a temperature between 18 and 60 ° C, are applied with the help of application rollers or with metering pumps using suitable applicators.
- the quantity of fiber preparations applied in undiluted form or in the form of aqueous emulsions is between 0.3 and 2% by weight, based on the weight of the thread bundle. After treatment with the preparations, the bundles of threads are wound on spinning bobbins.
- the aqueous emulsions of triacetin-containing fiber preparations usually contain 5 to 30% by weight of the undiluted fiber preparation.
- the fiber preparations according to the invention are preferably applied undiluted to polymeric filament materials, for example polypropylene, polyester and / or polyamide filaments.
- Triacetin which is toxicologically and ecologically harmless, also significantly reduces the tendency of textile lubricants to gel.
- the viscosities were determined using a Ubelhode viscometer.
- Fiber preparations of the following composition were used:
- the viscosity of the preparation was 146 mm2 / s at 20 ° C., and the viscosity of a 20% by weight aqueous emulsion was 31 mm2 / s at 20 ° C.
- the viscosity of the preparation was 115 mm2 / s at 20 ° C, the viscosity of a 20% by weight aqueous emulsion at 20 ° C was 23 mm2 / s.
- the viscosity of the preparation was 90 mm2 / s at 20 ° C, the viscosity of a 20 wt .-% aqueous emulsion at 20 ° C 7.5 mm2 / s.
- the viscosity at 20 ° C was 187 mm2 / s, the viscosity of a 20 wt .-% aqueous emulsion at 20 ° C 73 mm2 / s.
- the undiluted spin finishes A to D which had a temperature of 20 ° C., were applied to a preparation-free polypropylene multifilament (142 dtex) using a metering pump (oil coating: 0.5% by weight).
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
Die Erfindung betrifft die Verwendung von Triacetin in textilen Gleitmitteln und ein Verfahren zur Reduzierung der Viskosität textiler Gleitmittel.The invention relates to the use of triacetin in textile lubricants and a method for reducing the viscosity of textile lubricants.
Bei der Herstellung von synthetischen Fasermaterialien wird unmittelbar nach der Bildung der Filamente die Oberfläche der Fäden mit sogenannten Faserpräparationen behandelt ("Chemiefasern/Textil-Industrie" 1977, 328 - 335). Es ist allgemein bekannt, daß ohne eine solche Präparierung Synthesefasern weder hergestellt noch in der textilen Weiterverarbeitung verwendet werden können. Das Aufbringen eines Glättemittels ist notwendig, weil die ursprüngliche Oberfläche der meisten polymeren Fasermaterialien hohe Reibungskräfte verursacht, so daß durch die ständigen Kontakte mit beispielsweise Leitorganen während der Herstellungs- und Verarbeitungsprozesse ein Abscheuern der Fasern erfolgt, was letztlich zu Filament- oder Garnbrüchen führen kann. Des weiteren nehmen polymere Filamentmaterialien im allgemeinen nur wenig Wasser auf. Sie neigen daher dazu, zu isolieren und elektrische Aufladungen hervorzurufen. Selbst wenn die Fasern mit einem Glättemittel versehen sind, können trotzdem noch durch Reibung elektrostatische Aufladungen entstehen und das Abstoßen eines Filaments vom anderen kann den Verarbeitungsprozeß erschweren, wenn nicht sogar unmöglich machen.In the production of synthetic fiber materials, the surface of the threads is treated with so-called fiber preparations immediately after the formation of the filaments ("Chemical fibers / textile industry" 1977, 328-335). It is generally known that synthetic fibers can neither be produced nor used in further textile processing without such a preparation. The application of a smoothing agent is necessary because the original surface of most polymeric fiber materials causes high frictional forces, so that the fibers are rubbed off due to the constant contact with, for example, guide elements during the manufacturing and processing processes, which can ultimately lead to filament or yarn breaks. Furthermore, polymeric filament materials generally absorb little water. They therefore tend to isolate and electrical charges to evoke. Even if the fibers are provided with a smoothing agent, electrostatic charges can still arise due to friction and the repulsion of one filament from the other can make the processing process difficult, if not impossible.
Schmälzen sollen eine optimale Garnherstellung aus losen oder vorgeordneten Fasermaterialien gewährleisten und müssen daher insbesondere die Haft- und Gleiteigenschaften von Synthesestapelfasern, Naturfasern und/oder Mischungen von natürlichen und synthetischen Fasermaterialien verbessern (Chwala/Anger: "Handbuch der Textilhilfsmittel", Kap. 3.7, Verlag Chemie, Weinheim 1977).Melting should ensure optimal yarn production from loose or upstream fiber materials and must therefore in particular improve the adhesive and sliding properties of synthetic staple fibers, natural fibers and / or mixtures of natural and synthetic fiber materials (Chwala / Anger: "Handbuch der Textilhilhilmittel", chapter 3.7, publisher Chemistry, Weinheim 1977).
Viele Faserpräparationen und Schmälzen, die als Hauptwirksubstanzen Glättemittel, Antistatika und/oder Emulgatoren enthalten, sind fest, pastös oder zähflüssig. Da aus verarbeitungstechnischen Gründen flüssigen Faserpräparationen und Schmälzen der Vorzug gegeben wird, werden Faserpräparationen und Schmälzen mit Stellmitteln (Verdünnungsmitteln) in eine flüssige Form überführt. Je höher der für die gewünschte Viskosität benötigte Gehalt an Stellmitteln ist, um so mehr nimmt jedoch die Wirksamkeit, insbesondere die Gleitmittelwirksamkeit, der Präparationen und Schmälzen ab. Üblicherweise werden als Stellmittel Glykole und/oder Alkylglykole eingesetzt eingesetzt, die jedoch hinsichtlich ihrer Toxikologie nicht unbedenklich sind.Many fiber preparations and lubricants, which contain smoothing agents, antistatic agents and / or emulsifiers as their main active substances, are solid, pasty or viscous. Since preference is given to liquid fiber preparations and slicing for processing reasons, fiber preparations and slicing are converted into a liquid form using adjusting agents (diluents). However, the higher the leveling agent content required for the desired viscosity, the more the effectiveness, in particular the effectiveness of the lubricant, of the preparations and lubricants decreases. Glycols and / or alkyl glycols are usually used as adjusting agents, but their toxicology is not harmless.
Aus der französischen Offenlegungsschrift FR-A-784966 ist es bekannt, cellulosehaltige Produkte mit Glycerinestern wie Triacetin zu behandeln, um den Produkten eine Appretur zu verleihen bzw. um einen Weichmacher-Effekt zu erzielen.From French published patent application FR-A-784966 it is known to treat cellulose-containing products with glycerol esters such as triacetin in order to impart a finish to the products or to achieve a plasticizer effect.
Die der Erfindung zugrundeliegende Aufgabe bestand daher in der Entwicklung von Faserpräparationen und Schmälzen, die eine für die Applikation geeignete Viskosität besitzen, die die Gelneigung von Faserpräparationen und Schmälzen verhindern, zumindest jedoch erheblich reduzieren und die Fasermaterialien ausgezeichnete Glätteeigenschaften und eine sehr gute Antistatik verleihen. Des weiteren wird an die zu entwickelnden Faserpräparationen und Schmälzen die Bedingung gestellt, physiologisch unbedenklich zu sein.The object on which the invention is based was therefore the development of fiber preparations and lubricants which have a viscosity suitable for the application, which prevent the tendency of fiber preparations and lubricants to curl, but at least considerably reduce them, and give the fiber materials excellent smoothness properties and very good antistatic properties. Furthermore the fiber preparations and lubricants to be developed are subject to the condition of being physiologically harmless.
Überraschenderweise wurde gefunden, daß die an die Faserpräparationen und Schmälzen gestellten hohen Anforderungen von triacetinhaltigen Faserpräparationen und Schmälzen erfüllt werden.Surprisingly, it was found that the high demands placed on the fiber preparations and slicing are met by fiber preparations and sizing containing triacetin.
Gegenstand der Erfindung ist dementsprechend die Verwendung von Triacetin in textilen Gleitmitteln auf Basis von Glättemitteln, Antistatika und/oder Emulgatoren.The invention accordingly relates to the use of triacetin in textile lubricants based on smoothing agents, antistatic agents and / or emulsifiers.
Weiterer Erfindungsgegenstand ist ein Verfahren zur Reduzierung der Viskosität textiler Gleitmittel, welches dadurch gekennzeichnet ist, daß textile Gleitmittel auf Basis von Glättemitteln, Antistatika und/oder Emulgatoren mit Triacetin vermischt werden.Another object of the invention is a method for reducing the viscosity of textile lubricants, which is characterized in that textile lubricants based on smoothing agents, antistatic agents and / or emulsifiers are mixed with triacetin.
Der Begriff "textile Gleitmittel" umfaßt insbesondere Faserpräparationen und Avivagemittel, beispielsweise Schmälzen ("Ullmanns Encyclopädie der technischen Chemie", Band 23, Seiten 5 - 6, Verlag Chemie Weinheim 1983).The term "textile lubricant" includes in particular fiber preparations and finishing agents, for example smelting ("Ullmanns Encyclopedia of Industrial Chemistry", volume 23, pages 5-6, Verlag Chemie Weinheim 1983).
Das erfindungsgemäß einzusetzende Triacetin kann in an sich bekannter Weise, beispielsweise gemäß EP-A-33 929 durch Umsetzung von Glycerin mit Essigsäure und Essigsäureanhydrid, gegebenenfalls in Anwesenheit von Katalysatoren, hergestellt werden.The triacetin to be used according to the invention can be prepared in a manner known per se, for example according to EP-A-33 929, by reacting glycerol with acetic acid and acetic anhydride, if appropriate in the presence of catalysts.
Zur Herstellung der textilen Gleitmittel, insbesondere Faserpräparationen und Schmalzen werden Glättemittel und/oder Antistatika und/oder Emulgatoren und/oder gegebenenfalls weitere Additive und/oder gegebenenfalls Wasser bei 18 bis 25 °C mit Triacetin vermischt. Bevorzugt werden textile Gleitmittel, die
- 35 bis 95 Gew.-%
- Glättemittel, Emulgatoren, Antistatika und/oder Netzmittel
- 1 bis 40 Gew.-%
- Triacetin
- 0 bis 10 Gew.-%
- Additive, z. B.
pH-Wert-Regulantien, Fadenschlußmittel,
Bakterizide und/oder
Korrosionsschutzmittel und - 0 bis 50 Gew.-%
- Wasser
enthalten. Textile Gleitmittel mit
- 35 bis 95 Gew.-%
- Glättemitteln, Emulgatoren, Antistatika und/oder Netzmitteln
- 5 bis 30 Gew.-%
- Triacetin
- 0 bis 10 Gew.-%
- Additiven und
- 0 bis 30 Gew.-%
- Wasser
werden besonders bevorzugt.Smoothing agents are used to manufacture textile lubricants, especially fiber preparations and lard and / or antistatic agents and / or emulsifiers and / or optionally further additives and / or optionally water mixed at 18 to 25 ° C. with triacetin. Textile lubricants are preferred
- 35 to 95% by weight
- Smoothing agents, emulsifiers, antistatic agents and / or wetting agents
- 1 to 40% by weight
- Triacetin
- 0 to 10% by weight
- Additives, e.g. B.
pH regulators, thread closing agents,
Bactericides and / or
Anticorrosive and - 0 to 50% by weight
- water
contain. Textile lubricant with
- 35 to 95% by weight
- Smoothing agents, emulsifiers, antistatic agents and / or wetting agents
- 5 to 30% by weight
- Triacetin
- 0 to 10% by weight
- Additives and
- 0 to 30% by weight
- water
are particularly preferred.
Die textilen Gleitmittel können als Glättemittel, beispielsweise Mineralöle, Fettsäureester mit 8 bis 22 C-Atomen im Fettrest und 1 bis 22 C-Atomen im Alkoholrest, beispielsweise Palmitinsäuremethylester, Isobutylstearat und/oder Talgfettsäure-2-ethylhexylester, Polyolcarbonsäureester, beispielsweise Kokosfettsäureester von Glycerin und/oder alkoxylierten Glycerinen, Silikone, beispielsweise Dimethylpolysiloxan und/oder Polyalkylenglykole, beispielsweise Ethylenoxid/Propylenoxid-Mischpolymere mit mittleren Molekulargewichten zwischen 600 und 6.000 (Chemiefasern/Textil-Industrie 1977 335) enthalten. Als Emulgatoren, Netzmittel und/oder Antistatika kommen anionische, kationische und/oder nichtionische Tenside in Betracht, wie Mono- und/oder Diglyceride, beispielsweise Glycerinmono-und/oder Glycerindioleat, alkoxylierte, vorzugsweise ethoxylierte und/oder propoxylierte Fette, Öle, Fettalkohole mit 8 bis 24 C-Atomen und/oder C₈₋₁₈-Alkylphenole, beispielsweise Rizinusöl mit 25 Mol Ethylenoxid (EO) und/oder C₁₆₋₁₈-Fettalkohol mit 8 Mol Propylenoxid und 6 Mol EO, gewünschtenfalls alkoxylierte C₈₋₂₄-Fettsäuremono- und/oder -diethanolamide, beispielsweise gegebenenfalls ethoxyliertes Ölsäuremono- und/oder -diethanolamid, Talgfettsäuremono- und/oder -diethanolamid und/oder Kokosfettsäuremono- und/oder diethanolamid, Alkali- und/oder Ammoniumsalze alkoxylierter, vorzugsweise ethoxylierter und/oder propoxylierter, gegebenenfalls endgruppenverschlossener C₈₋₂₂-Alkyl- und/oder C₈₋₂₂-Alkenylalkoholsulfonate, Umsetzungsprodukte aus gegebenenfalls alkoxylierten C₈₋₂₂-Alkylalkoholen mit Phosphorpentoxid oder Phosphoroxychlorid in Form ihrer Alkali-, Ammonium- und/oder Aminsalze, beispielsweise Phosphorsäureester von ethoxyliertem C12/14-Fettalkohol, neutralisiert mit Alkanolaminen, Alkali- und/oder Ammoniumsalze von C₈₋₂₂-Alkylsulfosuccinaten, beispielsweise Natriumdioctylsulfosuccinat und/oder Aminoxiden, beispielsweise Dimethyldodecylaminoxid. Bei dieser beispielhaften Aufzählung von Glättemitteln, Emulgatoren, Antistatika und/oder Netzmitteln muß berücksichtigt werden, daß eine Vielzahl der genannten Substanzen nicht nur eine Funktion, sondern mehrere Funktionen besitzen: Beispielsweise kann ein Glättemittel gleichzeitig auch als Antistatikum und/oder als Emulgator wirken.The textile lubricants can be used as smoothing agents, for example mineral oils, fatty acid esters with 8 to 22 carbon atoms in the fat residue and 1 to 22 carbon atoms in the alcohol residue, for example methyl palmitate, isobutyl stearate and / or 2-ethylhexyl tallow fatty acid, polyol carboxylic acid esters, for example coconut fatty acid esters of glycerol and / or alkoxylated glycerols, silicones, for example dimethylpolysiloxane and / or polyalkylene glycols, for example ethylene oxide / propylene oxide mixed polymers with average molecular weights between 600 and 6,000 (chemical fibers / textile industry 1977 335) included. Suitable emulsifiers, wetting agents and / or antistatic agents are anionic, cationic and / or nonionic surfactants, such as mono- and / or diglycerides, for example glycerol mono- and / or glycerol dioleate, alkoxylated, preferably ethoxylated and / or propoxylated fats, oils, fatty alcohols 8 to 24 carbon atoms and / or C₈₋₁₈ alkylphenols, for example castor oil with 25 moles of ethylene oxide (EO) and / or C₁₆₋₁₈ fatty alcohol with 8 moles of propylene oxide and 6 moles of EO, if desired alkoxylated C₈₋₂₄ fatty acid mono- and / or -diethanolamides, for example optionally ethoxylated oleic acid mono- and / or -diethanolamide, tallow fatty acid mono- and / or -diethanolamide and / or coconut fatty acid mono- and / or diethanolamide, alkali and / or ammonium salts of alkoxylated, preferably ethoxylated and / or propoxylated, optionally end-capped C₈₋₂₂-alkyl and / or C₈₋₂₂-alkenyl alcohol sulfonates, reaction products from optionally alkoxylated C₈₋₂₂ alkyl alcohols with phosphorus pentoxide or phosphorus oxychloride in the form of their alkali, ammonium and / or amine salts, for example phosphoric acid esters of ethoxylated C 12/14 fatty alcohol, neutralized with alkanolamines, alkali and / or ammonium salts of C₈₋₂₂ alkyl sulfosuccinates , for example sodium dioctyl sulfosuccinate and / or amine oxides, for example dimethyldodecylamine oxide. In this exemplary list of smoothing agents, emulsifiers, antistatic agents and / or wetting agents, it must be taken into account that a large number of the substances mentioned have not only one function, but several functions: for example, a smoothing agent can simultaneously act as an antistatic agent and / or as an emulsifier.
Als fakultative Bestandteile enthalten die triacetinhaltigen textilen Gleitmittel Fadenschlußmittel, z. B. Polyacrylate, Fettsäuresarcoside und/oder Mischpolymerisate mit Maleinsäureanhydrid (Melliand Textilberichte 1977, 197) und/oder Polyurethane gemäß DE-A-38 30 468, pH-Wert-Regulantien, beispielsweise C₁₋₄-Carbonsäuren und/oder C₁₋₄-Hydroxycarbonsäuren, wie Essigsäure und/oder Glykolsäure, Alkalihydroxide, wie Kaliumhydroxid und/oder Amine wie Triethanolamin, Bakterizide und/oder Korrosionsschutzmittel.The optional triacetin-containing textile lubricants contain thread closure agents, e.g. B. polyacrylates, fatty acid sarcosides and / or copolymers with Maleic anhydride (Melliand Textile Reports 1977 , 197) and / or polyurethanes according to DE-A-38 30 468, pH regulators, for example C₁₋₄-carboxylic acids and / or C₁₋₄-hydroxycarboxylic acids, such as acetic acid and / or glycolic acid, alkali metal hydroxides , such as potassium hydroxide and / or amines such as triethanolamine, bactericides and / or anti-corrosion agents.
Üblicherweise werden triacetinhaltige Schmälzen auf Synthesestapelfasern, Naturfasern oder Mischungen aus natürlichen und synthetischen Fasermaterialien aufgesprüht. Die Auftragsmenge der Schmälzen in unverdünnter Form oder in Mischung mit Wasser liegt zwischen 0,1 und 3 Gew.-%, bezogen auf das Gewicht der Fasermaterialien.Triacetin-containing melts are usually sprayed onto synthetic staple fibers, natural fibers or mixtures of natural and synthetic fiber materials. The quantity of melt applied in undiluted form or in a mixture with water is between 0.1 and 3% by weight, based on the weight of the fiber materials.
Die Applikation triacetinhaltiger Faserpräparationen erfolgt in bekannter Weise unmittelbar nach Austritt der Kapillaren aus der Spinndüse. Die Faserpräparationen, die eine Temperatur zwischen 18 und 60 °C haben, werden mit Hilfe von Auftragswalzen oder mittels Dosierpumpen über geeignete Applikatoren aufgebracht. Die Auftragsmenge der Faserpräparationen in unverdünnter Form oder in Form wäßriger Emulsionen liegt zwischen 0,3 und 2 Gew.-%, bezogen auf das Gewicht der Fadenbündel. Nach der Behandlung mit den Präparationen werden die Fadenbündel auf Spinnspulen aufgewickelt.Triacetin-containing fiber preparations are applied in a known manner immediately after the capillaries have emerged from the spinneret. The fiber preparations, which have a temperature between 18 and 60 ° C, are applied with the help of application rollers or with metering pumps using suitable applicators. The quantity of fiber preparations applied in undiluted form or in the form of aqueous emulsions is between 0.3 and 2% by weight, based on the weight of the thread bundle. After treatment with the preparations, the bundles of threads are wound on spinning bobbins.
Die wäßrigen Emulsionen triacetinhaltiger Faserpräparationen enthalten üblicherweise 5 bis 30 Gew.-% der unverdünnten Faserpräparation.The aqueous emulsions of triacetin-containing fiber preparations usually contain 5 to 30% by weight of the undiluted fiber preparation.
Aufgrund ihrer niedrigen Viskosität werden die erfindungsgemäßen Faserpräparationen vorzugsweise unverdünnt auf polymere Filamentmaterialien, beispielsweise Polypropylen-, Polyester-und/oder Polyamidfilamente appliziert.Because of their low viscosity, the fiber preparations according to the invention are preferably applied undiluted to polymeric filament materials, for example polypropylene, polyester and / or polyamide filaments.
Im Vergleich zu den bekannten, stellmittelhaltigen textilen Gleitmitteln hat die Verwendung von Triacetin als Stellmittel in textilen Gleitmitteln keinen negativen Einfluß auf die glättende und antistatische Wirksamkeit solcher textiler Gleitmittel. Ferner bewirkt Triacetin, das toxikologisch und ökologisch unbedenklich ist, eine deutliche Reduzierung der Gelneigung von textilen Gleitmitteln.In comparison to the known, lubricant-containing textile lubricants, the use of triacetin as a lubricant in textile lubricants has no negative influence on the smoothing and antistatic effectiveness of such textile lubricants. Triacetin, which is toxicologically and ecologically harmless, also significantly reduces the tendency of textile lubricants to gel.
Die Viskositäten wurden mittels eines Ubelhode-Viskosimeters bestimmt.The viscosities were determined using a Ubelhode viscometer.
Es wurden Faserpräparationen folgender Zusammensetzung verwendet:Fiber preparations of the following composition were used:
- 90 Gew.-%90% by weight
- Kokosfettsäuremonoester von mit 10 Mol E0 ethoxyliertem GlycerinCoco fatty acid monoester of glycerol ethoxylated with 10 mol E0
- 10 Gew.-%10% by weight
- TriacetinTriacetin
Die Viskosität der Präparation betrug bei 20 °C 146 mm²/s, die Viskosität einer 20 Gew.-%igen wäßrigen Emulsion bei 20 °C 31 mm²/s.The viscosity of the preparation was 146 mm² / s at 20 ° C., and the viscosity of a 20% by weight aqueous emulsion was 31 mm² / s at 20 ° C.
- 80 Gew.-%80% by weight
- Kokosfettsäuremonoester von mit 10 Mol E0 ethoxyliertem GlycerinCoco fatty acid monoester of glycerol ethoxylated with 10 mol E0
- 20 Gew.-%20% by weight
- TriacetinTriacetin
Die Viskosität der Präparation betrug bei 20 °C 115 mm²/s, die Viskosität einer 20 gew.-%igen wäßrigen Emulsion bei 20 °C 23 mm²/s.The viscosity of the preparation was 115 mm² / s at 20 ° C, the viscosity of a 20% by weight aqueous emulsion at 20 ° C was 23 mm² / s.
- 70 Gew.-%70% by weight
- Kokosfettsäuremonoester von mit 10 Mol EO ethoxyliertem GlycerinCoco fatty acid monoester of glycerol ethoxylated with 10 mol EO
- 30 Gew. -%30% by weight
- TriacetinTriacetin
Die Viskosität der Präparation betrug bei 20 °C 90 mm²/s, die Viskosität einer 20 gew.-%igen wäßrigen Emulsion bei 20 °C 7,5 mm²/s.The viscosity of the preparation was 90 mm² / s at 20 ° C, the viscosity of a 20 wt .-% aqueous emulsion at 20 ° C 7.5 mm² / s.
- 100 Gew.-%100% by weight
- Kokosfettsäuremonoester von mit 10 Mol EO ethoxyliertem GlycerinCoco fatty acid monoester of glycerol ethoxylated with 10 mol EO
Die Viskosität betrug bei 20 °C 187 mm²/s, die Viskosität einer 20 gew.-%igen wäßrigen Emulsion bei 20 °C 73 mm²/s.The viscosity at 20 ° C was 187 mm² / s, the viscosity of a 20 wt .-% aqueous emulsion at 20 ° C 73 mm² / s.
Auf präparationsfreiem Polypropylenmultifilament (142 dtex) wurden die unverdünnten Spinnpräparationen A bis D, die eine Temperatur von 20 °C hatten, über eine Dosierpumpe aufgetragen (Ölauflage: 0,5 Gew.-%).The undiluted spin finishes A to D, which had a temperature of 20 ° C., were applied to a preparation-free polypropylene multifilament (142 dtex) using a metering pump (oil coating: 0.5% by weight).
Bei der Auswertung der Versuche wurden folgende Parameter bestimmt:The following parameters were determined when evaluating the tests:
Dynamische Reibungskoeffizienten gegen Stahl bei einer Geschwindigkeit von 100 m/min, gemessen am Rothschild F-Meter (Klima: 20°C, 65 % relative Feuchte)
elektrostatische Aufladung an Stahl bei einer Geschwindigkeit von 100 m/min, gemessen an Eltex Induktivvoltmeter (Klima: 20 °C, 65 % relative Feuchte)Dynamic coefficients of friction against steel at a speed of 100 m / min, measured on the Rothschild F-Meter (climate: 20 ° C, 65% relative humidity)
Electrostatic charging on steel at a speed of 100 m / min, measured on Eltex inductive voltmeters (climate: 20 ° C, 65% relative humidity)
Die Ergebnisse sind in Tabelle 1 zusammengefaßt.
Claims (4)
- The use of triacetin as a diluent in textile lubricants based on smoothing agents, antistatic agents and/or emulsifiers.
- The use claimed in claim 1, characterized in that they contain 1 to 40% by weight and preferably 5 to 30% by weight triacetin, based on the finish as a whole.
- A process for reducing the viscosity of textile lubricants, characterized in that textile lubricants based on smoothing agents, antistatic agents and/or emulsifiers are mixed with triacetin.
- A process as claimed in claim 3, characterized in that textile lubricants are mixed with - based on the finish as a whole - 1 to 40% by weight and preferably with 5 to 30% by weight triacetin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT90906172T ATE96857T1 (en) | 1989-04-26 | 1990-04-17 | USE OF TRIACETIN IN LUBRICANTS. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3913692 | 1989-04-26 | ||
| DE3913692A DE3913692A1 (en) | 1989-04-26 | 1989-04-26 | TRIACETIC TEXTILE LUBRICANTS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0470102A1 EP0470102A1 (en) | 1992-02-12 |
| EP0470102B1 true EP0470102B1 (en) | 1993-11-03 |
Family
ID=6379468
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90107201A Withdrawn EP0394802A1 (en) | 1989-04-26 | 1990-04-17 | Textile lubricants containing glycerol triacetate |
| EP90906172A Expired - Lifetime EP0470102B1 (en) | 1989-04-26 | 1990-04-17 | Use of Triacetin in Textile Gliding Agents |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90107201A Withdrawn EP0394802A1 (en) | 1989-04-26 | 1990-04-17 | Textile lubricants containing glycerol triacetate |
Country Status (8)
| Country | Link |
|---|---|
| EP (2) | EP0394802A1 (en) |
| JP (1) | JPH04504883A (en) |
| KR (1) | KR920701561A (en) |
| AU (1) | AU5425690A (en) |
| BR (1) | BR9007326A (en) |
| CA (1) | CA2054750A1 (en) |
| DE (2) | DE3913692A1 (en) |
| WO (1) | WO1990012916A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4201978A1 (en) * | 1991-05-29 | 1992-12-03 | Henkel Kgaa | FATTY ACID METHYL ESTERS IN LUBRICANTS FOR MATING YARN SPINNING |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR784966A (en) * | 1934-01-31 | 1935-07-30 | Deutsche Hydrierwerke Ag | Method of finishing and softening cellulosic products or articles |
| US3470095A (en) * | 1966-02-01 | 1969-09-30 | American Cyanamid Co | Aqueous textile treating emulsion |
| DE3004660A1 (en) * | 1980-02-08 | 1981-08-13 | Henkel KGaA, 4000 Düsseldorf | METHOD FOR THE CONTINUOUS PRODUCTION OF TRIACETINE |
| GB8616691D0 (en) * | 1986-07-09 | 1986-08-13 | Bp Chem Int Ltd | Acidulants |
-
1989
- 1989-04-26 DE DE3913692A patent/DE3913692A1/en not_active Withdrawn
-
1990
- 1990-04-17 BR BR909007326A patent/BR9007326A/en not_active Application Discontinuation
- 1990-04-17 DE DE90906172T patent/DE59003369D1/en not_active Expired - Fee Related
- 1990-04-17 WO PCT/EP1990/000594 patent/WO1990012916A1/en not_active Ceased
- 1990-04-17 AU AU54256/90A patent/AU5425690A/en not_active Abandoned
- 1990-04-17 KR KR1019910701456A patent/KR920701561A/en not_active Withdrawn
- 1990-04-17 JP JP2505951A patent/JPH04504883A/en active Pending
- 1990-04-17 EP EP90107201A patent/EP0394802A1/en not_active Withdrawn
- 1990-04-17 EP EP90906172A patent/EP0470102B1/en not_active Expired - Lifetime
- 1990-04-17 CA CA002054750A patent/CA2054750A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0394802A1 (en) | 1990-10-31 |
| DE3913692A1 (en) | 1990-10-31 |
| DE59003369D1 (en) | 1993-12-09 |
| JPH04504883A (en) | 1992-08-27 |
| BR9007326A (en) | 1992-04-28 |
| CA2054750A1 (en) | 1990-10-27 |
| EP0470102A1 (en) | 1992-02-12 |
| KR920701561A (en) | 1992-08-12 |
| WO1990012916A1 (en) | 1990-11-01 |
| AU5425690A (en) | 1990-11-16 |
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