EP0415279B1 - Use of ethoxylated fatty acid amides as textil softeners - Google Patents
Use of ethoxylated fatty acid amides as textil softeners Download PDFInfo
- Publication number
- EP0415279B1 EP0415279B1 EP90116223A EP90116223A EP0415279B1 EP 0415279 B1 EP0415279 B1 EP 0415279B1 EP 90116223 A EP90116223 A EP 90116223A EP 90116223 A EP90116223 A EP 90116223A EP 0415279 B1 EP0415279 B1 EP 0415279B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- reaction product
- ethylene oxide
- preparing
- textil
- softeners
- 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.)
- Revoked
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title description 3
- 239000000194 fatty acid Substances 0.000 title description 3
- 229930195729 fatty acid Natural products 0.000 title description 3
- 150000004665 fatty acids Chemical class 0.000 title description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229920001296 polysiloxane Polymers 0.000 claims description 10
- 239000004753 textile Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- 239000004744 fabric Substances 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- -1 optical brighteners Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229920001407 Modal (textile) Polymers 0.000 description 1
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- BOWVQLFMWHZBEF-KTKRTIGZSA-N oleoyl ethanolamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCO BOWVQLFMWHZBEF-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- D06M13/419—Amides having nitrogen atoms of amide groups substituted by hydroxyalkyl or by etherified or esterified hydroxyalkyl groups
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
Definitions
- the invention further relates to certain of the above reaction products, mixtures containing such reaction products and production processes therefor.
- RCO derives e.g. B. from lauric, linolenic, stearic, palmitic, tallow or coconut fatty acid and preferably from oleic acid.
- 16 moles of ethylene oxide per mole of I are used for the reaction of the compounds of the formula I.
- the compounds of the formula I are known; B. by reacting the acids of the formula RCOOH be prepared with monoethanolamine in a manner known per se.
- reaction products from the compounds and ethylene oxide are also known, for example from US Pat. No. 2,520,381.
- the reaction of the compounds of the formula I with ethylene oxide is advantageously carried out in such a way that the compounds I are added in portions with the ethylene oxide under elevated pressure (2 to 10, preferably 4 to 8 bar) at 100 to 140 ° C., preferably 110 to 120 ° C. implements. Potassium t-butoxide is preferably used as the catalyst. The reaction products are then worked up as usual.
- the reaction products from the compounds I and ethylene oxide are used as plasticizers for textiles, preferably fabrics made of cotton, rayon, Polynosic or other regenerated cellulose fibers, and mixtures thereof with fully synthetic fibers, such as polyamide, polyacrylonitrile, polyester or cellulose triacetate fibers, are used.
- reaction products used according to the invention are water-soluble and have a nonionic character. These two properties are advantageous for the compatibility with colorants and finishing agents used in the impregnation liquor, for example aminoplast precondensates for the crease and shrink-proof finish, dyes, pigments and binders, optical brighteners, water repellents, leveling agents and wetting agents.
- colorants and finishing agents for example aminoplast precondensates for the crease and shrink-proof finish, dyes, pigments and binders, optical brighteners, water repellents, leveling agents and wetting agents.
- no yellowing occurs during the high refinement.
- the softening agents can be used in any manner, e.g. by spraying or dipping and squeezing (padding) onto the textile material.
- the amounts used of the products used according to the invention can be varied within wide limits depending on the textile material to be treated, on the amount of finishing agents added and on the desired softening effect. In general, they are applied to the textile goods in amounts of 0.2-3% by weight, preferably 0.6-1.5% by weight, based on the weight of the goods, for the finishing of cotton and cellulose textiles.
- the products used according to the invention have better plasticizer properties and, moreover, have a stabilizing effect on silicone-based products.
- Polydimethyl siloxane emulsions are known to be used in textile finishing as excellent plasticizers and smoothing agents; they are mainly applied to the textile material using the padding process (dipping, squeezing).
- the disadvantage of all commercially available polysiloxane emulsions is their insufficient shear stability on the squeeze (foulard) rollers. At high production speeds, the emulsion breaks down due to the strong shear forces of the paddle rollers, which leads to the separation of the pure silicone oil from the emulsion. A roller covering forms, which causes irreparable stains on the goods.
- Favorable mixtures contain e.g. 1 to 6 parts by weight of silicone emulsion (silicon content 10 to 12%) and 9 to 4 parts by weight of the reaction products used according to the invention.
- a fabric made of 100% cotton with a weight of about 100 g / m2 is immersed in a bath, which in experiments a, b, c contains, then squeezed on the pad to a liquor absorption of about 80%, dried at 110 ° C and then condensed at 150 ° C for 5 min.
- the fabric finished according to experiment a) has a full, rough handle, whereas the fabrics finished under b) and c) feel pleasantly soft, smooth and flowing.
- a PES / Bw 50/50 blended fabric with a weight of approx. 90 g / m2 is soaked in the experiments a - d with an aqueous liquor which contains, then squeezed to a liquor absorption of about 70% on the foulard, dried at 110 ° C and condensed at 150 ° C for 5 min.
- test liquors a - d were first stirred with a stirrer at 3000 rpm for 10 minutes. The formation of the roller cover was then checked as follows:
- the foulard has two horizontally mounted rollers, 9 cm in diameter and 15 cm in length.
- the drive takes place electrically via a continuously variable transmission.
- the roller pressure is set using a lever arm 35 cm long; at the end of the lever arm there are about 12 kg of lead weight.
- the hardness of the paddle rollers is 72 ° shore (drive roller) and 84 ° shore hardness (pressure roller).
- An endless web fabric 12 cm wide and 56 cm long is allowed to run through the liquor from below into the crushing unit at about 12 m / min for 30 minutes.
- the roller covering is visually rated from 1 (no roller covering) to 5 (strong roller covering).
- the surface of the rollers is smooth and clean.
- the fleet a) also received the grade 1.
- Example 3 The procedure is as in Example 3, but starting from 243.3 g (1 mol) of lauric acid monoethanolamide. In contrast to Example 3, the final adjustment to pH 6 is carried out with phosphoric acid. Approx. 2460 g of 40% solution are obtained.
Description
Die Erfindung betrifft die Verwendung der Umsetzungsprodukte von Verbindungen der Formel I
RCONHC₂H₄OH I
in der
- R
- einen C₁₂- bis C₂₀-, vorzugsweise C₁₆- bis C₂₀-, Alkyl- oder Alkenylrest bedeutet,
mit 14 bis 18 mol Ethylenoxid pro Mol I als Textilweichmacher.The invention relates to the use of the reaction products of compounds of the formula I.
RCONHC₂H₄OH I
in the
- R
- is a C₁₂- to C₂₀-, preferably C₁₆- to C₂₀-, alkyl or alkenyl radical,
with 14 to 18 moles of ethylene oxide per mole of I as a fabric softener.
Ferner betrifft die Erfindung gewisse der obigen Umsetzungsprodukte, Mischungen enthaltend solche Umsetzungsprodukte und Herstellungs-verfahren dafür.The invention further relates to certain of the above reaction products, mixtures containing such reaction products and production processes therefor.
Der Rest RCO leitet sich z. B. von der Laurin-, Linolen-, Stearin-, Palmitin-, Talgfett- oder Kokosfettsäure und vorzugsweise von der Ölsäure ab.The rest of RCO derives e.g. B. from lauric, linolenic, stearic, palmitic, tallow or coconut fatty acid and preferably from oleic acid.
Vorzugsweise nimmt man für die Umsetzung der Verbindungen der Formel I 16 mol Ethylenoxid pro Mol I. Die Verbindungen der Formel I sind bekannt, sie können z. B. durch Umsetzung der Säuren der Formel
RCOOH
mit Monoethanolamin in an sich bekannter Weise hergestellt werden.Preferably, 16 moles of ethylene oxide per mole of I are used for the reaction of the compounds of the formula I. The compounds of the formula I are known; B. by reacting the acids of the formula
RCOOH
be prepared with monoethanolamine in a manner known per se.
Die Umsetzungsprodukte aus den Verbindungen und Ethylenoxid sind zum Teil ebenfalls bekannt, beispielsweise aus der US-A 2 520 381.Some of the reaction products from the compounds and ethylene oxide are also known, for example from US Pat. No. 2,520,381.
Die Umsetzung der Verbindungen der Formel I mit Ethylenoxid erfolgt zweckmäßigerweise so, daß man die Verbindungen I unter erhöhtem Druck (2 bis 10, vorzugsweise 4 bis 8 bar) bei 100 bis 140°C, vorzugsweise 110 bis 120°C, portionsweise mit dem Ethylenoxid umsetzt. Als Katalysator wird vorzugsweise Kalium-t-butylat verwendet. Die Umsetzungsprodukte werden dann wie üblich aufgearbeitet.The reaction of the compounds of the formula I with ethylene oxide is advantageously carried out in such a way that the compounds I are added in portions with the ethylene oxide under elevated pressure (2 to 10, preferably 4 to 8 bar) at 100 to 140 ° C., preferably 110 to 120 ° C. implements. Potassium t-butoxide is preferably used as the catalyst. The reaction products are then worked up as usual.
Einzelheiten der Herstellung können den Beispielen entnommen werden, in denen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht beziehen.Details of the production can be found in the examples, in which information on parts and percentages, unless stated otherwise, relate to the weight.
Die Umsetzungsprodukte aus den Verbindungen I und Ethylenoxid werden als Weichmacher für Textilien, vorzugsweise Gewebe aus Baumwolle, Zellwolle, Polynosic oder sonstigen Celluloseregeneratfasern, sowie deren Mischungen mit vollsynthetischen Fasern, wie Polyamid-, Polyacrylnitril-, Polyester- oder Cellulosetriacetat-Fasern, verwendet.The reaction products from the compounds I and ethylene oxide are used as plasticizers for textiles, preferably fabrics made of cotton, rayon, Polynosic or other regenerated cellulose fibers, and mixtures thereof with fully synthetic fibers, such as polyamide, polyacrylonitrile, polyester or cellulose triacetate fibers, are used.
Sie ergeben auf den Textilien einen angenehmen, weichen, fließenden und glatten Warengriff.They result in a pleasant, soft, flowing and smooth handle on the textiles.
Die erfindungsgemäß verwendeten Umsetzungsprodukte sind wasserlöslich und haben einen nichtionogenen Charakter. Diese beiden Eigenschaften sind vorteilhaft für die Verträglichkeit mit Farb- und Ausrüstungsmitteln, die in der Imprägnierflotte verwendet werden, beispielsweise Aminoplast-Vorkondensaten für die Knitterfrei- und Schrumpffestausrüstung, Farbstoffen, Pigmenten und Bindemitteln, optischen Aufhellern, Hydrophobier-, Egalisier- und Netzmitteln. Insbesondere bei zur Farbaufhellung nach üblichen Methoden nachbehandelten erfindungsgemäßen Produkten tritt bei der Hochveredlung keine Vergilbung auf.The reaction products used according to the invention are water-soluble and have a nonionic character. These two properties are advantageous for the compatibility with colorants and finishing agents used in the impregnation liquor, for example aminoplast precondensates for the crease and shrink-proof finish, dyes, pigments and binders, optical brighteners, water repellents, leveling agents and wetting agents. In particular in the case of products according to the invention aftertreated for color brightening by customary methods, no yellowing occurs during the high refinement.
Die Weichmachungsmittel können auf beliebige Weise, z.B. durch Aufsprühen oder Tauchen und Abquetschen (Foulardieren) auf das Textilmaterial aufgebracht werden.The softening agents can be used in any manner, e.g. by spraying or dipping and squeezing (padding) onto the textile material.
Die Einsatzmengen der erfindungsgemäß verwendeten Produkte können in Abhängigkeit von dem zu behandelnden Textilgut, von der Menge der zugesetzten Ausrüstungsmittel und von dem gewünschten Weichmachungseffekt in weiten Grenzen variiert werden. Im allgemeinen werden sie bei der Hochveredlung von Baum- und Zellwolltextilien in Mengen von 0,2 - 3 Gew.-%, vorzugsweise 0,6 - 1,5 Gew.-%, bezogen auf das Warengewicht, auf das Textilgut aufgebracht.The amounts used of the products used according to the invention can be varied within wide limits depending on the textile material to be treated, on the amount of finishing agents added and on the desired softening effect. In general, they are applied to the textile goods in amounts of 0.2-3% by weight, preferably 0.6-1.5% by weight, based on the weight of the goods, for the finishing of cotton and cellulose textiles.
Gegenüber bisher üblichen Weichmachern auf Basis von alkoxylierten Fettsäuren haben die erfindungsgemäß verwendeten Produkte bessere Weichmachereigenschaften und zudem noch stabilisierende Wirkung auf Produkte auf Silikonbasis.Compared to plasticizers based on alkoxylated fatty acids that have been customary to date, the products used according to the invention have better plasticizer properties and, moreover, have a stabilizing effect on silicone-based products.
Polydimethyl-Siloxanemulsionen werden bekannterweise in der Textilveredlung als ausgezeichnete Weichmacher und Glättungsmittel verwendet; sie werden überwiegend im Foulardverfahren (Tauchen, Abquetschen) auf das Textilgut aufgetragen. Der Nachteil aller handelsüblichen Polysiloxan-Emulsionen ist jedoch ihre nicht ausreichende Scherstabilität auf den Abquetsch-(Foulard)Walzen. Bei hoher Produktionsgeschwindigkeit bricht die Emulsion durch die starken Scherkräfte der Foulardwalzen zusammen, was zur Ausscheidung des reinen Silikonöls aus der Emulsion führt. Es bildet sich ein Walzenbelag, der irreparable Flecken auf der Ware verursacht.Polydimethyl siloxane emulsions are known to be used in textile finishing as excellent plasticizers and smoothing agents; they are mainly applied to the textile material using the padding process (dipping, squeezing). The disadvantage of all commercially available polysiloxane emulsions, however, is their insufficient shear stability on the squeeze (foulard) rollers. At high production speeds, the emulsion breaks down due to the strong shear forces of the paddle rollers, which leads to the separation of the pure silicone oil from the emulsion. A roller covering forms, which causes irreparable stains on the goods.
Durch Abmischen der Polysiloxanemulsionen mit den erfindungsgemäß verwendeten Produkten verbessert sich wesentlich deren Scherstabilität, so daß es dadurch möglich wird, hohe Produktionsgeschwindigkeiten einzustellen. Bezüglich der anwendungstechnischen Eigenschaften erhält man mit den Mischprodukten gleich gute Ergebnisse wie mit den reinen Silikonweichmachern allein, die vergleichsweise hohe Kosten verursachen.Mixing the polysiloxane emulsions with the products used according to the invention significantly improves their shear stability, so that it becomes possible to set high production speeds. Regarding the application properties, the mixed products give the same good results as the pure silicone plasticizers alone, which cause comparatively high costs.
Günstige Mischungen enthalten z.B. 1 - 6 Gew.-Teile Silikonemulsion (Siliziumgehalt 10 - 12 %) und 9 - 4 Gew.-Teile der erfindungsgemäß verwendeten Umsetzungsprodukte.Favorable mixtures contain e.g. 1 to 6 parts by weight of silicone emulsion (silicon content 10 to 12%) and 9 to 4 parts by weight of the reaction products used according to the invention.
Ein Gewebe aus 100 % Baumwolle mit einem Gewicht von etwa 100 g/m² wird in je ein Bad getaucht, das bei den Versuchen a, b, c
enthält, anschließend auf dem Foulard auf eine Flottenaufnahme von etwa 80 % abgequetscht, bei 110°C getrocknet und danach 5 Min. bei 150°C kondensiert.A fabric made of 100% cotton with a weight of about 100 g / m² is immersed in a bath, which in experiments a, b, c
contains, then squeezed on the pad to a liquor absorption of about 80%, dried at 110 ° C and then condensed at 150 ° C for 5 min.
Das gemäß Versuch a) ausgerüstete Gewebe hat einen vollen, rauhen Griff, hingegen fühlen sich die unter b) und c) ausgerüsteten Gewebe angenehm weich, glatt und fließend an.The fabric finished according to experiment a) has a full, rough handle, whereas the fabrics finished under b) and c) feel pleasantly soft, smooth and flowing.
Eine PES/Bw 50/50-Mischgewebe mit einem Gewicht von ca. 90 g/m² wird bei den Versuchen a - d jeweils mit einer wäßrigen Flotte getränkt, die
enthält, anschließend wird auf eine Flottenaufnahme von ca. 70 % auf dem Foulard abgequetscht, bei 110°C getrocknet und 5 Min. bei 150°C kondensiert.A PES / Bw 50/50 blended fabric with a weight of approx. 90 g / m² is soaked in the experiments a - d with an aqueous liquor which
contains, then squeezed to a liquor absorption of about 70% on the foulard, dried at 110 ° C and condensed at 150 ° C for 5 min.
6 Teile 30%ige wäßrige Lösung vom Umsetzungsprodukt, hergestellt nach Beispiel 3, und 4 Teile 30%ige Emulsion vom Silikonweichmacher aus Versuch d).6 parts of 30% aqueous solution of the reaction product, prepared according to Example 3, and 4 parts of 30% emulsion of the silicone plasticizer from experiment d).
5 Teile 30%ige wäßrige Lösung vom Umsetzungsprodukt, hergestellt nach Beispiel 4, und 5 Teile 30%ige Emulsion vom gleichen Silikonweichmacher wie im Versuch d).5 parts of 30% aqueous solution of the reaction product, prepared according to Example 4, and 5 parts of 30% emulsion from the same silicone plasticizer as in experiment d).
Der Unterschied im Warengriff zwischen b, c und d ist nicht erkennbar. Die ausgerüstete Ware fühlt sich in den Versuchen b - d gleich weich an, mit charakteristischer silikonspezifischer Glätte. Dagegen fühlt sich das nach Versuch a) ausgerüstete Gewebe hart und rauh an.The difference in the handle between b, c and d is not recognizable. In the trials b - d, the finished goods feel equally soft, with a characteristic silicone-specific smoothness. In contrast, the fabric finished after trial a) feels hard and rough.
Zur Prüfung der Scherstabilität wurden die Versuchsflotten a - d zuerst mit einem Rührer bei 3000 U/min 10 Min. gerührt. Danach wurde die Walzenbelagsbildung wie folgt geprüft:To test the shear stability, the test liquors a - d were first stirred with a stirrer at 3000 rpm for 10 minutes. The formation of the roller cover was then checked as follows:
Von der Flotte werden 450 ml in das Chassis eines Foulards gegeben. Der Foulard hat zwei horizontal gelagerte Walzen von 9 cm Durchmesser und 15 cm Länge. Der Antrieb erfolgt elektrisch über ein stufenlos regelbares Getriebe. Der Walzendruck wird über einen Hebelarm von 35 cm Länge eingestellt; am Ende des Hebelarms hängen etwa 12 kg Bleigewicht. Die Härte der Foulardwalzen beträgt 72° Shore (Antriebswalze) und 84° Shore Härte (Druckwalze).450 ml of the liquor are added to the chassis of a foulard. The foulard has two horizontally mounted rollers, 9 cm in diameter and 15 cm in length. The drive takes place electrically via a continuously variable transmission. The roller pressure is set using a lever arm 35 cm long; at the end of the lever arm there are about 12 kg of lead weight. The hardness of the paddle rollers is 72 ° shore (drive roller) and 84 ° shore hardness (pressure roller).
Ein endloses Bw-Gewebe von 12 cm Breite und 56 cm Länge läßt man 30 Minuten lang durch die Flotte von unten in das Quetschwerk mit etwa 12 m/min einlaufen. Der Walzenbelag wird visuell bewertet von 1 (kein Walzenbelag) - 5 (starker Walzenbelag).An endless web fabric 12 cm wide and 56 cm long is allowed to run through the liquor from below into the crushing unit at about 12 m / min for 30 minutes. The roller covering is visually rated from 1 (no roller covering) to 5 (strong roller covering).
Die Flotten, die die Mischprodukte (b + c) enthalten, ergeben keinen Walzenbelag. Die Oberfläche der Walzen ist glatt und sauber. Die Note 1 bekam auch die Flotte a). Die Flotte d) bekam jedoch die Note 3 - 4; auf den Walzen waren deutlich Silikonablagerungen zu sehen.The liquors, which contain the mixed products (b + c), do not result in a roller coating. The surface of the rollers is smooth and clean. The fleet a) also received the grade 1. The fleet d), however, received a grade of 3-4; Silicon deposits were clearly visible on the rollers.
- 325 g (1 Mol)325 g (1 mole)
- Ölsäuremonoethanolamid werden in einem Autoklaven mitOleic acid monoethanolamide are in an autoclave
- 3,3 g (1 Gew.-%)3.3 g (1% by weight)
- Kalium-tert.-butylat undPotassium tert-butoxide and
- 0,3 g (0,1 Gew.-%)0.3 g (0.1% by weight)
- phosphoriger Säure versetzt und bei 110 - 120°C portionsweise mitphosphorous acid and added at 110 - 120 ° C in portions
- 740 g (16 Mol)740 g (16 moles)
- Ethylenoxid bei einem Druck von 5 - 10 bar umgesetzt. Nach Beendigung der Ethoxylierung wird nichtumgesetztes Ethylenoxid während 1 h bei 80°C/1 mbar abgezogen (Kontrolle: Preußmann-Test). Das Ethoxylat wird mitEthylene oxide reacted at a pressure of 5 - 10 bar. After the ethoxylation has ended, unreacted ethylene oxide is drawn off at 80 ° C./1 mbar for 1 h (control: Preussmann test). The ethoxylate comes with
- 1915 g1915 g
- Wasser verdünnt und die wäßrige Lösung bei RT mitDiluted water and the aqueous solution at RT with
- 6 g (0,07 Mol)6 g (0.07 mol)
- Oxalsäure auf einen pH von 6,0 eingestellt. Man erhält ca. 2960 g 35 %ige Lösung.Oxalic acid adjusted to pH 6.0. About 2960 g of 35% solution are obtained.
Man verfährt wie in Beispiel 3, geht jedoch von 243,3 g (1 Mol) Laurinsäuremonoethanolamid aus. Die abschließende Einstellung auf pH 6 erfolgt im Gegensatz zu Beispiel 3 mit Phosphorsäure. Man erhält ca. 2460 g 40%ige Lösung.The procedure is as in Example 3, but starting from 243.3 g (1 mol) of lauric acid monoethanolamide. In contrast to Example 3, the final adjustment to pH 6 is carried out with phosphoric acid. Approx. 2460 g of 40% solution are obtained.
Claims (6)
- A process for softening textiles, which comprises using a reaction product of a compound of the formula I
RCONHC₂H₄OH I
where R is C₁₂-C₂₀-alkyl or -alkenyl, with 14-18 mol of ethylene oxide per mole of I. - A process for preparing a reaction product as defined in claim 1, which comprises starting from compound I in which R is derived from oleic acid.
- A process for preparing a reaction product as defined in claim 1, wherein the compound I is reacted with 16 mol of ethylene oxide.
- A process for preparing a reaction product as defined in claim 1, wherein oleic ethanolamide is reacted with 16 mol of ethylene oxide.
- A process for preparing a textile softener, which comprises mixing a reaction product as defined in claim 1 with a silicone-based softener.
- A process for preparing a textile softener as claimed in claim 5, wherein the reaction product and the silicone softener are mixed in a weight ratio of 9-4:1-6.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3928978 | 1989-09-01 | ||
| DE3928978A DE3928978A1 (en) | 1989-09-01 | 1989-09-01 | ETHOXYLATED FATTY ACID AMIDES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0415279A1 EP0415279A1 (en) | 1991-03-06 |
| EP0415279B1 true EP0415279B1 (en) | 1994-01-12 |
Family
ID=6388366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP90116223A Revoked EP0415279B1 (en) | 1989-09-01 | 1990-08-24 | Use of ethoxylated fatty acid amides as textil softeners |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US5080811A (en) |
| EP (1) | EP0415279B1 (en) |
| DE (2) | DE3928978A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4415062B4 (en) * | 1994-04-29 | 2004-04-01 | Stockhausen Gmbh & Co. Kg | Means and processes for waterproofing leather and furs |
| DE19626317A1 (en) * | 1996-07-01 | 1998-01-08 | Basf Ag | Condensation products of fatty acids with amino alcohols and polyols and their use as textile auxiliaries |
| BR112021005118A2 (en) * | 2018-09-21 | 2021-06-15 | Nouryon Chemicals International B.V. | process; use of an ethoxylated fatty amino alcohol in the process of manufacturing viscose from cellulose; use of 0.005 to 2.0% by weight of an ethoxylated fatty amino alcohol in a bleach and cellulose reaction process and subsequent reaction of alkaline cellulose with cs2 to reduce the amount of unreacted alkaline cellulose in the xanthed product; viscose obtained through a process; solid cellulose and solid cellulose composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2520381A (en) * | 1946-06-18 | 1950-08-29 | American Cyanamid Co | Condensation of ethylene oxide with carboxylic acid amides |
| DE2136673A1 (en) * | 1971-07-22 | 1973-02-01 | Henkel & Cie Gmbh | Textile softening agent - comprising a carboxylic acid amide and trisacryloyl-hexahydro-1,3,5-triazine for use in washing compsns |
| US4685930A (en) * | 1984-11-13 | 1987-08-11 | Dow Corning Corporation | Method for cleaning textiles with cyclic siloxanes |
| US4818248A (en) * | 1986-10-10 | 1989-04-04 | Ciba-Geigy Corporation | Process for dyeing natural or synthetic polyamide fibre materials with 1:1 metal complex dyes in presence of alkali metal fluordsilicate or amindnlum silicate |
| JPH07109064B2 (en) * | 1987-12-02 | 1995-11-22 | 竹本油脂株式会社 | Method for imparting water permeability to polyolefin fibers |
-
1989
- 1989-09-01 DE DE3928978A patent/DE3928978A1/en not_active Withdrawn
-
1990
- 1990-08-24 EP EP90116223A patent/EP0415279B1/en not_active Revoked
- 1990-08-24 DE DE90116223T patent/DE59004202D1/en not_active Revoked
- 1990-08-31 US US07/575,623 patent/US5080811A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US5080811A (en) | 1992-01-14 |
| DE3928978A1 (en) | 1991-03-07 |
| EP0415279A1 (en) | 1991-03-06 |
| DE59004202D1 (en) | 1994-02-24 |
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