DE2539310A1 - Textile softener solns. or dispersions - contg. condensate of fatty acid or ester and alkyl propylene diamine oxyalkylate - Google Patents
Textile softener solns. or dispersions - contg. condensate of fatty acid or ester and alkyl propylene diamine oxyalkylateInfo
- Publication number
- DE2539310A1 DE2539310A1 DE19752539310 DE2539310A DE2539310A1 DE 2539310 A1 DE2539310 A1 DE 2539310A1 DE 19752539310 DE19752539310 DE 19752539310 DE 2539310 A DE2539310 A DE 2539310A DE 2539310 A1 DE2539310 A1 DE 2539310A1
- Authority
- DE
- Germany
- Prior art keywords
- mol
- fatty acid
- formula
- oxyalkylate
- contg
- 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.)
- Granted
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 22
- 239000000194 fatty acid Substances 0.000 title claims abstract description 22
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 22
- 239000004753 textile Substances 0.000 title claims abstract description 18
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 17
- 239000006185 dispersion Substances 0.000 title claims abstract description 11
- 125000005667 alkyl propylene group Chemical group 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title description 3
- -1 fatty acid ester Chemical class 0.000 claims abstract description 8
- 239000012141 concentrate Substances 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 239000007859 condensation product Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000002979 fabric softener Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000004744 fabric Substances 0.000 claims description 4
- 239000004902 Softening Agent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 235000021355 Stearic acid Nutrition 0.000 abstract description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract description 5
- 239000008117 stearic acid Substances 0.000 abstract description 5
- 238000005406 washing Methods 0.000 abstract description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- 229920002284 Cellulose triacetate Polymers 0.000 abstract description 2
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 239000004743 Polypropylene Substances 0.000 abstract description 2
- 229920002301 cellulose acetate Polymers 0.000 abstract description 2
- 229920002239 polyacrylonitrile Polymers 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 229920001155 polypropylene Polymers 0.000 abstract description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract description 2
- 210000002268 wool Anatomy 0.000 abstract description 2
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 235000008504 concentrate Nutrition 0.000 abstract 1
- SEPFQHJECFKHGD-UHFFFAOYSA-N henicos-2-ene Chemical group CCCCCCCCCCCCCCCCCCC=CC SEPFQHJECFKHGD-UHFFFAOYSA-N 0.000 abstract 1
- 235000020354 squash Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- KFXTTZQGCNRYEN-UHFFFAOYSA-N 2-n-octadecylpropane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNC(C)CN KFXTTZQGCNRYEN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VGYLMOJQAHXYCK-UHFFFAOYSA-N 1-methylimidazolidine Chemical compound CN1CCNC1 VGYLMOJQAHXYCK-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 229940095602 acidifiers Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000029219 regulation of pH Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- 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
- 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
- D06M13/35—Heterocyclic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/368—Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
Textilweichmacher Es ist bekannt, dass gewaschene Textilien, besonders solche aus Cellulosefasern nach dem Trocknen eine unangenehme Verhärtung des Griffes aufweisen. Dieses tritt besonders dann ein, lçenn die Wäsche im Waschautomaten erfolgt.Fabric softener It is known that washed textiles, especially those made of cellulose fibers cause an unpleasant hardening of the handle after drying exhibit. This occurs especially when the laundry is done in the washing machine.
Es ist ferner bekannt, dass man diese unerwünschte Griffverhärtung dadurch beseitigen kann, dass man die Textilien nach der Wäsche in einem Spülbad mit kationischen Substanzen behandelt, die mindestens 2 langkettige aliphatische Reste im Molekül enthalten. In der Praxis haben sich für diesen Zweck besonders die in Wasser suspendierbaren Dialkyl-dimethylammoniumsalze eingefiihrt. Diese Produkte haben jedoch den Nachteil, dass sie in ihrer bevorzugten Handelsform, als konzentrierte Lösungen, einen brennbaren Alkohol enthalten und nicht fliessfähig sind, sondern eine pastenförmige Konsistenz aufweisen und ausserdem nur bei erhöhter Temperatur verarbeitbar sind.It is also known that this undesirable hardening of the handle can be avoided can be eliminated by putting the textiles in a rinsing bath after washing treated with cationic substances that are at least 2 long-chain aliphatic Contains residues in the molecule. In practice they have been specially chosen for this purpose the water-suspendable dialkyl-dimethylammonium salts were introduced. These products however, they have the disadvantage that they are in their preferred commercial form, as concentrated Solutions that contain a flammable alcohol and are not flowable, but rather have a paste-like consistency and, moreover, only at elevated temperature are processable.
Es ist zwar bekannt, dass man als Textilweichmacher gewisse Imidazoliniumverbindungen verwenden kann, die als konzentrierte alkoholische Lösungen fliessfähig und mit kaltem Wasser verdünnbar sind. Bei diesen Imidazolinverbindungen handelt es sich z.B. um das Methosulfat des 1-Alkylamidoäthyl-2-alkyl-3-methyl-imidazolins, dessen weichmachende Wirkung jedoch wesentlich geringer ist als die der Dialkyldimethyl-ammoniumsalze.It is known that certain imidazolinium compounds are used as textile softeners can use that as concentrated alcoholic solutions flowable and with can be diluted in cold water. These imidazoline compounds are e.g. to the methosulfate of 1-alkylamidoethyl-2-alkyl-3-methyl-imidazoline, its The softening effect, however, is much less than that of the dialkyldimethylammonium salts.
Es wurde nun gefunden, dass Textilweichmacher auf Basis von Kondensationsprodukten aus etwa 1 bis 1,5 Mol, vorzugsweise 1 bis 1,2 Mol, einer Fettsäure oder eines Fettsäureesters der Formel I R-CO2X (I) worin R einen vorzugsweise gesättigten aliphatischen Rest mit etwa 11 bis 21 Kohlenstoffatomen, vorzugsweise einen Alkylrest mit 15 bis 17 Kohlenstoffatomen, und X Wasserstoff, Methyl oder Äthyl bedeuten, -mit 1 Mol eines Alkylpropylendiamin-oxalkylates der allgemeinen Formel II in der R1 einen vorzugsweise gesättigten aliphatischen Rest mit etwa 12 bis 22 Kohlenstoffatomen, vorzugsweise einen Alkylrest mit 16 bis 18 Kohlenstoffatomen, R2 Wasserstoff oder Methyl, insbesondere Wasserstoff, bedeuten, und x, y und z für 0 oder 1 stehen, wobei die Summe von x, y und t 1 oder 2 ist, die vorstehend geschilderten Nachteile der bekannten Weichmacher nicht aufweisen.It has now been found that textile softeners based on condensation products of about 1 to 1.5 mol, preferably 1 to 1.2 mol, of a fatty acid or a fatty acid ester of the formula I R-CO2X (I) wherein R is a preferably saturated aliphatic radical about 11 to 21 carbon atoms, preferably an alkyl radical with 15 to 17 carbon atoms, and X denotes hydrogen, methyl or ethyl, with 1 mol of an alkylpropylenediamine oxyalkylate of the general formula II in which R1 is a preferably saturated aliphatic radical with about 12 to 22 carbon atoms, preferably an alkyl radical with 16 to 18 carbon atoms, R2 is hydrogen or methyl, in particular hydrogen, and x, y and z are 0 or 1, the sum of x, y and t is 1 or 2, do not have the disadvantages of the known plasticizers described above.
Bei den Kondensationsprodukten aus Verbindungen der Formeln 1 und II handelt es sich vor allem um solche, in denen die Reste R und R1 Alkylgruppen darstellen. Wegen ihrer Herstellung aus natürlichen Fettsäuregemischen können jedoch auch solche Mischungen von Kondensationsprodukten als Weichmacher zur Anwendung kommen, die einen untergeordneten Anteil an Verbindungen enthalten, in denen R und/oder R 1 Alkenylreste bedeuten.In the case of the condensation products from compounds of the formulas 1 and II are above all those in which the radicals R and R1 are alkyl groups represent. However, because they are made from natural fatty acid mixtures, Such mixtures of condensation products are also used as plasticizers come, which contain a minor proportion of compounds in which R and / or R 1 mean alkenyl radicals.
Gegenstand der Erfindung sind ferner fliessfähige Konzentrate von Textilweichmachern, im wesentlichen bestehend aus etwa 20 bis 35 Gewichtsprozent eines vorstehend genannten Fettsäurekondensationsproduktes.The invention also relates to flowable concentrates of Fabric softeners consisting essentially of about 20 to 35 percent by weight an above-mentioned fatty acid condensation product.
Die Herstellung der erfindungsgemäss verwendeten Kondensationsprodukte geschieht in einfacher Weise durch Umsetzen des Alkylpropylendiamin-oxalkylats der Formel II mit der Fettsäure bzw. deren Ester in dem angegebenen Mol-Verhältnis bei Temperaturen von etwa 1300 bis 2500 C, vorzugsweise 1600 bis 2000 C. Je nach der angewandten Temperatur und der eingesetzten Fettsäurekomponente sind bis zu 10 Stunden meist etwa 2 bis 8 Stunden notwendig, um das Reaktionsgleichgewícht zu erreichen. Bei Kondensation im Vakuum kann die Umsetzung schon bei niedrigerer Temperatur, beispielsweise 1200 bis 1600 C erfolgen.The preparation of the condensation products used according to the invention happens in a simple manner by reacting the alkylpropylenediamine oxyalkylate Formula II with the fatty acid or its ester in the specified molar ratio Temperatures of about 1300 to 2500 C, preferably 1600 to 2000 C. Depending on the applied temperature and the fatty acid component used are up to 10 hours usually about 2 to 8 hours are necessary to achieve the reaction equilibrium. In the case of condensation in a vacuum, the reaction can take place at a lower temperature, for example 1200 to 1600 C take place.
Nach Beendigung der Kondensationsreaktion kann die Schmelze des im Wesentliehen aus einem Fettsäureamid bestehenden Reaktionsproduktes in Wasser dispergiert werden, wobei entweder die Schmelze nach Schwachalkalisch- bis Schwachsauereinstellung mit einer wasserlöslichen starken organischen oder anorganischen Säure in Wasser eingerührt wird oder wobei die Schmelze in Wasser eingerührt und gleichzeitig oder anschliessend die organische oder anorganische Säure zugesetzt wird. Als organische bzw. anorganische Säuren kommen vor allem Mineralsäuren, wie Salzsäure, Phosphorsäure, Schwefelsäure, Essigsäure oder Oxalsäure zum Einsatz. Man erhält so eine flüssige, in kaltem Wasser verdünnbare Dispersion mit einem Gehalt bis zu etwa 35 % Wirkstoff.After the condensation reaction has ended, the melt of the im Substantially composed of a fatty acid amide reaction product dispersed in water be where either the melt according to weakly alkaline to weakly acidic setting with a water-soluble strong organic or inorganic acid in water is stirred in or the melt is stirred into water and at the same time or then the organic or inorganic acid is added. As organic or inorganic acids are mainly mineral acids such as hydrochloric acid, phosphoric acid, Sulfuric acid, acetic acid or oxalic acid are used. So you get a liquid, Dispersion which can be diluted in cold water and contains up to about 35% active ingredient.
Als Fettsäuren kommen vor allem gesättigte Fettsäuren oder Fettsäuregemische in Betracht, die höchstens untergeordnete Anteile an olefinisch ungesättigten Säuren enthalten. Vor allem finden Fettsäuren aus ganz oder teilweise gehärteten Fetten Verwendung. Geeignete Fettsäuren sind z.B. Palmitinsäure, Stearinsäure sowie Talgfettsäure. Als Ester dieser Fettsäuren kommen in erster Linie die mit niederen Alkoholen, besonders die Äthyl- und Methylester in Betracht.The main fatty acids are saturated fatty acids or fatty acid mixtures into consideration, the maximum minor proportions of olefinically unsaturated acids contain. Above all, fatty acids can be found from fully or partially hydrogenated fats Use. Suitable fatty acids are, for example, palmitic acid, stearic acid and tallow fatty acid. The esters of these fatty acids are primarily those with lower alcohols, especially the ethyl and methyl esters into consideration.
Die erfindungsgemäss zu verwendenden Kondensationsprodukte sind in Wasser löslich oder dispergierbar. Als Weichmacher für Textilien kann man sie in der Weise anwenden, dass man das Behandlungsgut durch Tauchen oder Besprühen mit wässrigen Lösungen dieser Kondensationsprodukte tränkt. Im allgemeinen bringt man hierbei etwa 0,01 bis 0,7 ,bezogen auf das Gewicht des Textilmaterials, an Kondensationsprodukten auf das Textilmaterial auf.The condensation products to be used according to the invention are in Water soluble or dispersible. They can be used as softeners for textiles apply in such a way that you can dip or spray the material to be treated with soaks aqueous solutions of these condensation products. Generally one brings here about 0.01 to 0.7, based on the weight of the textile material, of condensation products on the textile material.
Die wässrigen Lösungen oder Dispersionen des Textilweichmachers gemäss der Erfindung, die im allgemeinen einen Gehalt von etwa 1 bis 15 Gewichtsprozent, meist 4 bis 10 Gewichtsprozent, der beanspruchten Kondensationsprod-ikte aufweisen, können ausserdem weitere Komponenten oder Hilfsmittel enthalten, die entweder schon den Konzentraten der Kondensationsprodukte zugemischt waren oder den wässrigen Lösungen oder Dispersionen oder den zum Gebrauch bestimmten Behandlungsbädern gesondert zugesetzt worden sind. Hierbei handelt es sich um Substanzen oder Hilfsmittel, die man bereits in Wäscheweichspülmitteln eingesetzt hat; zu diesen gehören z.B.The aqueous solutions or dispersions of the textile softener according to of the invention, which generally have a content of about 1 to 15 percent by weight, usually 4 to 10 percent by weight of the claimed condensation products, can also contain other components or auxiliaries, the either the concentrates of the condensation products were already mixed in or the aqueous solutions or dispersions or the treatment baths intended for use have been added separately. These are substances or aids which have already been used in fabric softeners; these include e.g.
kationische oder nichtionogene oberflächenaktive Substanzen, Elektrolyte, Absäuerungsmittel oder Lösungsvermittler sowie Farb- und Duftstoffe. Sie dienen beispielsweise einer zusätzlichen Beeinflussung des Warengriffs oder sonstigen Eigenschaften der zu behandelnden Textilien oder der Viskositätseinstellung, der pH-Regulierung oder der Erhöhung der Kältestabilität der Lösungen.cationic or non-ionic surface-active substances, electrolytes, Acidifiers or solubilizers as well as dyes and fragrances. You serve for example, an additional influence on the handle of the goods or other properties the textiles to be treated or the viscosity setting, the pH regulation or increasing the cold stability of the solutions.
Nach dem Imprägnieren mit den die erfindungsgemässen Textilweichmacher enthaltenden Bädern wird das Textilgut auf übliche Weise getrocknet.After impregnation with the textile softeners according to the invention containing baths, the textile material is dried in the usual way.
Die Kondensationsprodukte gemäss der Erfindung haben sich als Wäschenachbehandlungsmittel als besonders geeignet erwiesen. Bei dieser Anwendung gibt man sie im Anschluss an die Textilwäsche in das letzte Spülbad.The condensation products according to the invention have proven to be used as laundry aftertreatment agents proved to be particularly suitable. In this application, they are given afterwards to the textile laundry in the last rinse.
Die Kondensationsprodukte gemäss der Erfindung verleihen beliebigen Textilmaterialien, besonders solchen aus natürlicher oder regenerierter Cellulose, Wolle, Celluloseacetat und Triacetat, Polyamid, Polyacrylnitril, Polyester und Polypropylen einen angenehmen weichen Griff. Besonders vorteilhaft ist der Einsatz als Wäschenachbehandlungsmittel für Frottee- und Leibwäsche.The condensation products according to the invention impart any Textile materials, especially those made from natural or regenerated cellulose, Wool, cellulose acetate and triacetate, polyamide, polyacrylonitrile, polyester and polypropylene a pleasant soft grip. Use as a laundry aftertreatment agent is particularly advantageous for terry and underwear.
Beispiel 1: 345 g (1 Mol) einer Anlagerungsverbindung von 1 Mol ÄthylenZ oxid an 1 Mol Stearylpropylendiamin und 264 g (1 Mol) Stearinsäure werden 5 Stunden unter Stickstoff-Durchleiten bei 1800 C und 2 Stunden bei 165° C und 25 Torr kondensiert.Example 1: 345 g (1 mol) of an addition compound of 1 mol ÄthylenZ oxide to 1 mole of stearylpropylenediamine and 264 g (1 mole) of stearic acid are 5 hours condensed while passing nitrogen through at 1800 C and 2 hours at 165 ° C and 25 Torr.
Man erhält 576 g eines gelblich gefärbten Produkts (Basen-Stickstoff 2,6 , Säurezahl = 0), das bei 1000 C mit 1540 g H20 verrührt und mit 83 g Eisessig auf pH = 4,7 (gemessen in zeiger wässriger Lösung) gestellt wird. Man erhält eine farblose, in kaltem Wasser verdünnbare Dispersion, die 30 Gewichtsprozent Feststoff enthält.576 g of a yellowish colored product are obtained (base nitrogen 2.6, acid number = 0), which is stirred at 1000 C with 1540 g of H20 and with 83 g of glacial acetic acid is set to pH = 4.7 (measured in pointer aqueous solution). You get one colorless dispersion that can be diluted in cold water, which is 30 percent by weight solids contains.
Beispiel 2: 390 g (11 Mol) einer Anlagerungsverbindung von 1 Mol Äthylenoxid an 1 Mol Talgfettpropylendiamin und 264 g (1 Mol) Stearinsäure werden 8 Stunden unter Stickstoff-Durchleiten bei 1800 C kondensiert. Man erhält 630 g eines gelblich gefärbten Produkts (Basen-Stickstoff 3,3 %s Säurezahl 1,5), das bei 1000 C mit 1700 g H20 verrührt und mit 105 g Eisessig auf pH 4,6 (gemessen in 1%iger wässriger Lösung) gestellt wird. Man erhält eine farblose, in kaltem Wasser dispergierbare Dispersion, die 30 % Feststoff enthält.Example 2: 390 g (11 mol) of an addition compound of 1 mol of ethylene oxide of 1 mol of tallow fat propylenediamine and 264 g (1 mol) of stearic acid are 8 hours condensed at 1800 C while passing nitrogen through. 630 g of a yellowish one are obtained colored product (base nitrogen 3.3% s acid number 1.5), which at 1000 C with 1700 g H20 stirred and with 105 g glacial acetic acid to pH 4.6 (measured in 1% aqueous solution) is provided. A colorless dispersion which can be dispersed in cold water is obtained, which contains 30% solids.
Beispiel 3: 389 g (1 Mol) einer Anlagerungsverbindung von 2 Mol Äthyienoxid an 1 Mol Stearylpropylendiamin und 264 (1 Mol) Stearinsäure werden analog der in Beispiel 1 angegebenen Arbeitsweise kondensiert.Example 3: 389 g (1 mole) of an addition compound of 2 moles of ethylene oxide of 1 mol of stearylpropylenediamine and 264 (1 mol) of stearic acid are analogous to that in Example 1 specified procedure condensed.
Prüfung des Weichmachungseffektes von Wäscheweichspülmitteln Die Bestimmung der weichmachenden Wirkung der in den Beispielen 1 bis 3 aufgeführten Verbindungen erfolgte in Ermangelung anderer Testmethoden durch Beurteilung des Griffs von entsprechend nachbehandelten Frotteelappen.Testing the softening effect of fabric softeners The determination the softening effect of the compounds listed in Examples 1 to 3 was carried out in the absence of other test methods by assessing the handle of accordingly post-treated terry cloths.
Um die weichmachende Wirkung eines Weichspülmittelrohstoffs im Vergleich zu einem Standardprodukt genau angeben zu können, werden die mit dem zu prüfenden Produkt nachbehandelten Baumwoll-Frotteelappen nach ihrem Weichheitsgrad in eine Reihe von mit unterschiedlichen Konzentrationen eines Standardproduktes nachbehandelten Lappen eingeordnet und daraus die Wirksamkeit des jeweiligen Weichspülmittels mit einer Genauigkeit von ca. + 10 ffi bestimmt.A comparison of the softening effect of a fabric softener raw material To be able to specify exactly a standard product, those with the to be tested become After-treated cotton terry cloths into a product according to their degree of softness Series of post-treated with different concentrations of a standard product Cloth and from this the effectiveness of the respective fabric softener with with an accuracy of approx. + 10 ffi.
Durchführung der Prüfung Die gekennzeichneten Frotteelappen (Gewicht ca. 20 g) werden bei 800 C und einem Flottenverhältnis von 1 : 10 mit 6 g/l eines handelsüblichen Vollwaschmittels gewaschen und fünfmal mit kaltem Trinkwasser gespült. Nach kurzem Schleudern (ca.Carrying out the test The marked terry cloth cloths (weight approx. 20 g) are at 800 C and a liquor ratio of 1:10 with 6 g / l of one commercially available heavy-duty detergent and rinsed five times with cold drinking water. After a short spin (approx.
3 Sekunden) sind die Lappen, die jetzt einen vorgegebenen harten Griff aufweisen, zur Nachbehandlung vorbereitet.3 seconds) are the lobes that now have a predetermined hard grip have prepared for post-treatment.
Aus dem zu prüfenden Weichmacher bzw. dem fertig konfektionierten Weicbspülmittel wird eine 1%ige (bezogen auf Wirkstoff) wässrige Dispersion hergestellt. Jewells 2 ml und 4 ml dieser Dispersion werden mit Trinkwasser auf 200 ml (entsprechend 0,1 bzw. 0,2 g/l Weichmacherwirkstoff) verdünnt. In diese verdünnten Lösungen werden die vorbereiteten, noch feuchten Frotteelappen hineingegeben und 5 Minuten lang bei 200 C im Launderometer nachbehandelt. Das Flottenverhältnis beträgt 1 : 10. Danach werden die Testlappen den Behältern entnommen, 5 Sekunden lang geschleudert, bei 70 bis 80° C im Trockenschrank getrocknet und anschliessend 24 Stunden im Klimaraum bei 200 C und 60 0% relativer Luftfeuchtigkeit gelaçgert. Dann erfolgte die Griffbeurteilung unabhängig durch jeweils 7 geübte Personen.From the plasticizer to be tested or the finished product Weicbspülmittel a 1% (based on active ingredient) aqueous dispersion is produced. 2 ml and 4 ml of this dispersion are added to 200 ml with drinking water (corresponding to 0.1 or 0.2 g / l plasticizer active ingredient) diluted. Be in these dilute solutions Put in the prepared, still damp terry cloth and hold for 5 minutes Post-treated at 200 C in a launderometer. The liquor ratio amounts to 1: 10. Then the test cloths are removed from the containers, spun for 5 seconds, Dried in a drying cabinet at 70 to 80 ° C and then in a climatic room for 24 hours stored at 200 C and 60 0% relative humidity. Then the grip assessment took place independently by 7 experienced people.
Auswertung Wie bereits oben erwähnt, werden die mit unterschiedlichen Mengen des Prüfprodukts nachbehandelten Frotteestücke nach dem Grad ihrer Weichheit in eine Reihe von mit unterschiedlichen Konzentrationen an Standardprodukt (1 -Talgfettalkylamidoäthyl-2-talgfettalkyl-3-methyl-imidazolinium-methosulfat) nachbehandelten Lappen eingeordnet. Die Konzentrationsreihe muss selbstverständlich der jeweiligen Wirksamkeit des Prüfprodukts angepasst und gegebenenfalls entsprechend abgeändert werden. Um die Sicherheit der Prüfergebnisse zu erhöhen, wird die Prüfung mindestens einmal wiederholt. Auf diese Weise wird als Mittelwert aller Beurteilungen eine relativ genaue Angabe des Weichmachungseffektes einer Testsubstanz im Vergleich zu einem Standardprodukt erhalten.Evaluation As already mentioned above, the with different Quantities of the test product of post-treated terry pieces according to the degree of their softness in a number of with different concentrations of standard product (1-tallow fatty alkylamidoethyl-2-tallow fatty alkyl-3-methyl-imidazolinium-methosulfate) after-treated flaps. The concentration series must of course adapted to the respective effectiveness of the test product and, if necessary, accordingly be modified. In order to increase the security of the test results, the test repeated at least once. In this way, all the assessments are taken as the mean a relatively precise indication of the plasticizing effect of a test substance in comparison to get a standard product.
Nach dieser Prüfmethode wurden für die Produkte der Beispiele 1 bis 3 die in der nachfolgenden Tabelle aufgeführten Ergebnisse erhalten. Es zeigt sich, dass die Kondensationsprodukte gemäss der Erfindung eine deutlich bessere weichmachende Wirkung aufweisen als das vergleichbare handelsübliche Wäscheweichspülmittel.According to this test method for the products of Examples 1 to 3 obtained the results listed in the table below. It appears, that the condensation products according to the invention have a significantly better plasticizing Have an effect than the comparable commercially available fabric softener.
T A B E L L E
Claims (3)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752539310 DE2539310A1 (en) | 1975-09-04 | 1975-09-04 | Textile softener solns. or dispersions - contg. condensate of fatty acid or ester and alkyl propylene diamine oxyalkylate |
| NL7609628A NL7609628A (en) | 1975-09-04 | 1976-08-30 | TEXTILE TREATMENT AGENT. |
| US05/719,194 US4092253A (en) | 1975-09-04 | 1976-08-31 | Fabric softeners |
| CH1109676A CH606595A5 (en) | 1975-09-04 | 1976-09-01 | |
| IT26799/76A IT1074423B (en) | 1975-09-04 | 1976-09-02 | DETERGENT AND SOFTENER FOR FABRICS CONTAIN THE CONDENSATION PRODUCT AS A SOFTENING AGENT BETWEEN A FATTY ACID OR ITS ESTER AND AN ALCHIPROPILENDIAMMINOOS SIALKYLATE |
| LU75705A LU75705A1 (en) | 1975-09-04 | 1976-09-02 | |
| DK398776A DK398776A (en) | 1975-09-04 | 1976-09-03 | TEXTILE PROCESSING AGENT |
| JP51105098A JPS5234097A (en) | 1975-09-04 | 1976-09-03 | Treating agents for fiber article |
| SE7609754A SE7609754L (en) | 1975-09-04 | 1976-09-03 | TEXTILE TREATMENT |
| FR7626784A FR2322964A1 (en) | 1975-09-04 | 1976-09-06 | SOFTENERS FOR TEXTILE MATERIALS |
| GB36899/76A GB1553976A (en) | 1975-09-04 | 1976-09-06 | Amide-type condensation products and fabric softener and detergent compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752539310 DE2539310A1 (en) | 1975-09-04 | 1975-09-04 | Textile softener solns. or dispersions - contg. condensate of fatty acid or ester and alkyl propylene diamine oxyalkylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2539310A1 true DE2539310A1 (en) | 1977-03-17 |
| DE2539310C2 DE2539310C2 (en) | 1988-06-16 |
Family
ID=5955558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752539310 Granted DE2539310A1 (en) | 1975-09-04 | 1975-09-04 | Textile softener solns. or dispersions - contg. condensate of fatty acid or ester and alkyl propylene diamine oxyalkylate |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2539310A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0038862A1 (en) * | 1979-08-03 | 1981-11-04 | Albright & Wilson Limited | Compositions containing amido amine salts, and their use as fabric softeners |
| EP0069948A1 (en) * | 1981-07-10 | 1983-01-19 | Hoechst Aktiengesellschaft | Quaternary N-alkyl-N,N'-polyoxyalkyl-alpha, omega-diaminoalkylene fatty-acid esters, process for their production and their use |
| CN113089309A (en) * | 2021-03-27 | 2021-07-09 | 安徽省伊贝雅纺织有限公司 | Towel treatment process |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2340881A (en) * | 1939-08-22 | 1944-02-08 | Nat Oil Prod Co | Composition for lubricating and softening textile fibers |
-
1975
- 1975-09-04 DE DE19752539310 patent/DE2539310A1/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2340881A (en) * | 1939-08-22 | 1944-02-08 | Nat Oil Prod Co | Composition for lubricating and softening textile fibers |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0038862A1 (en) * | 1979-08-03 | 1981-11-04 | Albright & Wilson Limited | Compositions containing amido amine salts, and their use as fabric softeners |
| EP0069948A1 (en) * | 1981-07-10 | 1983-01-19 | Hoechst Aktiengesellschaft | Quaternary N-alkyl-N,N'-polyoxyalkyl-alpha, omega-diaminoalkylene fatty-acid esters, process for their production and their use |
| CN113089309A (en) * | 2021-03-27 | 2021-07-09 | 安徽省伊贝雅纺织有限公司 | Towel treatment process |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2539310C2 (en) | 1988-06-16 |
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