EP0112496A2 - Emulsion adoucissante, procédé pour sa préparation et son utilisation - Google Patents

Emulsion adoucissante, procédé pour sa préparation et son utilisation Download PDF

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Publication number
EP0112496A2
EP0112496A2 EP83111631A EP83111631A EP0112496A2 EP 0112496 A2 EP0112496 A2 EP 0112496A2 EP 83111631 A EP83111631 A EP 83111631A EP 83111631 A EP83111631 A EP 83111631A EP 0112496 A2 EP0112496 A2 EP 0112496A2
Authority
EP
European Patent Office
Prior art keywords
weight
alkyl radical
atoms
plasticizer
alkaline earth
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.)
Withdrawn
Application number
EP83111631A
Other languages
German (de)
English (en)
Other versions
EP0112496A3 (fr
Inventor
Karl-Heinz Dr. Keil
Ulrich Dr. Greiner
Georg-Wolfgang Dr. Eckardt
Volker Köhler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis Deutschland GmbH
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella AG
Cassella Farbwerke Mainkur AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cassella AG, Cassella Farbwerke Mainkur AG filed Critical Cassella AG
Publication of EP0112496A2 publication Critical patent/EP0112496A2/fr
Publication of EP0112496A3 publication Critical patent/EP0112496A3/fr
Withdrawn legal-status Critical Current

Links

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
    • D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
    • D06M13/03—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons with unsaturated hydrocarbons, e.g. alkenes, or alkynes
    • 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
    • C11D3/323—Amides; Substituted amides urea or derivatives thereof
    • 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
    • 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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • D06M15/427—Amino-aldehyde resins modified by alkoxylated compounds or alkylene oxides

Definitions

  • the invention relates to an aqueous reactive, viscosity-stable and storage-stable plasticizer emulsion with a hydrophobizing effect, processes for its preparation and its use.
  • the DE-C 1,231,663 relates to a process for the production of hydrophobic agents on textiles, in which these are treated with liquors which thermosetting polysiloxanes condensing agent for the polysiloxanes, and condensation products of aminoplast-N- V erbin- compounds, formaldehyde, aliphatic monocarboxylic acids with contain more than 10 carbon atoms and / or resin acids and alkanolamines. It is then dried and condensed. By using conventional synthetic resin pre-condensates, you can also improve the grip in addition to the hydrophobization.
  • the simultaneous hydrophobization and improvement in grip can only be achieved by using products from different substance classes, which leads to storage stability problems or makes it necessary to add the different substances to the finishing bath only shortly before the treatment.
  • the condensation is carried out at temperatures from 130 to 150 ° C. in the presence of soaps or salts of polyvalent metals, such as zirconium, these condensation temperatures being maintained very precisely must be done, because otherwise a drastic deterioration in grip can be observed.
  • hydrophobizing agents which contain a hydrophobic aminoplast, a Pao raffin of melting point 40 to 80 C and certain thermally cleavable emulsifiers.
  • the disadvantage here is that synthetic resin precondensates have to be used.
  • a significant deterioration in the rub fastness of the cured textile material must be expected through the use of cleavable emulsifiers.
  • DE-B 19 34 177 discloses textile softening agents in the form of aqueous solutions or dispersions which, as plasticizer components, contain reaction products of at least 3 mol of formaldehyde and 1 mol of N-alkylurea or N-alkylbiuret compounds with about 14 to 22 carbon atoms in the alkyl radical contain.
  • the grip achieved by these agents is in some cases not yet smooth and soft enough, and the water repellency is not sufficient.
  • DE-B 23 20 302 describes mixtures of at least one mono- and / or dimethylol-alkylurea with 12 to 22 carbon atoms in the alkyl radical and at least one butyl ether of a mono- and / or dimethylol-alkylurea with 12 to 22 carbon atoms known in the alkyl radical, which are used as plasticizers for cellulose fibers.
  • the water repellency of these mixtures is not sufficient, and the handle obtained does not yet have the desired fullness.
  • the butyl ethers cause odor problems during processing and waste water problems arise during the removal of the liquors.
  • the emulsions of this mixture have very little storage stability.
  • N-methylol-behenic acid amide and N-methylol-docosyl-carbamate are known as water repellents. Because of their high melting points, however, these compounds can only be converted with difficulty into aqueous emulsions which then have only a short shelf life and storage stability. In addition, these compounds cannot be used in a bath together with synthetic resin precursors, otherwise the finishing bath will become unstable.
  • plasticizer emulsion according to the invention fulfills these requirements.
  • the plasticizer emulsion according to the invention contains 15 to 35% by weight of a mixture containing 0.5 to 6% by weight of at least one anionic emulsifier 0.25 to 3% by weight of at least one alkaline earth metal ion in the form of at least one soluble alkaline earth metal compound 0 to 10% by weight of at least one water-immiscible solvent 46 to 84.25% by weight water, where for the numbers a, b, c and d applies and also the conditions must be satisfied and R is an alkyl radical with 12 to 22 C atoms, R 1 is an alkyl radical with 1 to 4 C atoms, R 2 is an alkyl radical with 12 to 30 C atoms, n is a number from 1 to 3.
  • R, R 1 and R 2 can be straight-chain or branched.
  • R 2 is preferably a straight-chain alkyl radical having 18 to 22 carbon atoms
  • R 1 is methyl or ethyl
  • R is an alkyl radical having 18 to 22 carbon atoms.
  • the ratio (a + b): (a + b + c + d) is preferably 1: (1.43 to 3.3).
  • a representative of the following substance classes V to V II is particularly suitable as the anionic emulsifier.
  • R 3 is a straight-chain or branched alkyl or alkenyl radical having 12 to 18 carbon atoms
  • R 4 is hydrogen or a straight-chain or branched alkyl radical having 1 to 4 carbon atoms
  • X + is a monovalent cation or a half divalent cation
  • m is a number from 10 to 30, preferably from 20 to 30.
  • X + preferably denotes an alkaline application, in particular the N a- trium or potassium cation, or half an alkaline earth metal cation, in particular the calcium, magnesium or strontium cation, the ammonium cation or a substituted ammonium cation, such as, for example, the tris-hydroxyethylammonium.
  • a single anionic emulsifier or a mixture of different anionic emulsifiers can be present in the plasticizer emulsion.
  • alkaline earth ions e.g. the magnesium, calcium or strontium ion or mixtures thereof are used.
  • the alkaline earth ions are in the form of soluble alkaline earth compounds, e.g. in the form of chlorides or nitrates, introduced into the emulsion.
  • the alkaline earth metal ions can expediently also be introduced as the alkaline earth metal salt of the anionic emulsifier, as a result of which the addition of a further alkaline earth metal salt can be unnecessary.
  • water-immiscible solvents e.g. to name: lower alcohols, e.g. Ethanol, ether, e.g. Dioxane, etherified glycols, e.g. Methyl glycol, ethyl glycol, ethyl diglycol, methyl diglycol, n-propyl glycol, i-propyl glycol, n-butyl glycol, n-butyl diglycol, i-butyl diglycol.
  • lower alcohols e.g. Ethanol
  • ether e.g. Dioxane
  • etherified glycols e.g. Methyl glycol, ethyl glycol, ethyl diglycol, methyl diglycol, n-propyl glycol, i-propyl glycol, n-butyl glycol, n-butyl diglycol, i-butyl diglycol.
  • the plasticizer emulsion according to the invention is prepared in that a mixture containing the compounds I to IV with at least one anionic Emulsifier, eg at temperatures of 70 to 100 ° C, preferably 75 to 95 ° C, melted and the melt with warm water using a high-speed mixing - or homogenizer in an aqueous emulsion is transferred, and in that before, during or after the emulsification or Alkaline earth metal ions in the form of soluble alkaline earth metal compounds are added, unless the required content of alkaline earth metal ions has already been introduced by an anionic emulsifier containing alkaline earth metal ions and that at least one water-miscible solvent is optionally added before, during or after the emulsification.
  • anionic Emulsifier eg at temperatures of 70 to 100 ° C, preferably 75 to 95 ° C
  • plasticizer emulsion In the preparation of the plasticizer emulsion, the amounts of the individual components are chosen so that a plasticizer emulsion of the composition mentioned is formed. Particularly favorable plasticizer emulsions are obtained if, before the emulsification, the melt containing the compounds of the formulas I to IV and the anionic emulsifier or the mixture of various anionic emulsifiers are in the molten state at temperatures from 70 to 70 to 10 minutes, preferably 10 to 30 minutes 100 ° C, preferably from 75 to 95 0 C, are kept. As a result of the condensation taking place, the application properties, in particular the storage stability, of the plasticizer emulsions according to the invention are further improved considerably.
  • the melt is erbin- from the V compounds of the formulas VIII and IX to temperatures of 90 to 120 ° C, preferably 90 to 95 0 C, cooled, and to the 2 to 4-fold molar amount of formaldehyde or form 'aldehyde-releasing substances transferred.
  • the formaldehyde is preferably introduced into the melt in solid form, for example in the form of paraformaldehyde or metaldehyde. If the methylolation is carried out at temperatures below 100 ° C., the formaldehyde can also be introduced into the melt in the form of an aqueous solution, for example the commercially available 39% strength aqueous solution.
  • the etherification with the compound of the formula X is expediently carried out together with the methylolation in one step in the presence of a basic catalyst, such as, for example, a tertiary amine or alkanolamine, for example triethanolamine, N-methylcyclohexyl amine, N-methylmorpholine, in an amount of, for example, 0.5 to 2% by weight.
  • a basic catalyst such as, for example, a tertiary amine or alkanolamine, for example triethanolamine, N-methylcyclohexyl amine, N-methylmorpholine
  • the formaldehyde is expediently introduced into the melt in the form of a solution of paraformaldehyde in the glycol ether of the formula X. About 2 to 3 mol of the glycol ether are used.
  • the methylolation and etherification are complete after about 1 to 4 hours.
  • excess glycol ether of the formula X still present can then be distilled off under reduced pressure. However, complete removal of the excess glycol ether of the formula X is not necessary because it can remain in the plasticizer emulsion according to the invention as a water-immiscible solvent.
  • the methylolation can also be carried out first and then the etherification with the glycol ether of the formula X can be carried out in a second stage.
  • the etherification is in Anatorihei-t of catalytic amounts of acids, such as of hydrochloric acid, nitric acid, sulfuric acid, formic acid or p-toluenesulfonic acid at temperatures ranging from - 60 to 150 ° C, preferably from 80 to 120 o C, performed.
  • End product mixtures with degrees of etherification of 30 to 70% are prepared in particular in that a melt of a compound VIII and a compound IX in a glycol ether of the formula X, preferably methyl glycol, at temperatures from 90 to 130 ° C. preferably 95 to 110 ° C, and after adjusting the pH to 7.5 to 9.5, preferably 8 to 8.5, is methylolated at the temperatures mentioned by adding solid formaldehyde (paraformaldehyde or metaldehyde), where etherification is immediately excluded from the methylolation.
  • solid formaldehyde paraformaldehyde or metaldehyde
  • the tertiary amines or alkanolamines already mentioned are used, for example.
  • the required starting compounds of the formula VIII can be prepared by reacting an alkyl isocyanate of the formula RNCO with ammonia or preferably by reacting an alkylamine of the formula RNH 2 with urea.
  • the reaction of the alkyl isocyanate of the formula RNCO with ammonia is generally carried out in an inert organic solvent, such as, for example, a hydrocarbon, ether or halogenated hydrocarbon, such as, for example, benzene, toluene, xylene, dioxane, tetrahydrofuran, cyclohexane, chloroform, carbon tetrachloride and / or ethylene chloride at temperatures between 15 to 110 ° C, especially at 20 to 70 ° C.
  • the reaction can also be carried out in a mixture of inert solvents.
  • the preparation of the compounds of the formula VIII by fusing an amine of the formula RNH 2 with urea is preferred because the compounds of the formula VIII are obtained free of by-products containing biurethane and free of starting amine RNH 2 . This is important because biure-containing by-products in the finished plasticizer emulsion negatively affect the handle and residues of starting amine cause yellowing.
  • the reaction of the alkylamine RNH 2 with urea is normally carried out in such a way that a higher-chain alkylamine RNH 2 , such as, for example, hexadecylamine, Octadecylamine, docosylamine, eicosylamine or especially the technical fatty alkylamines with a natural chain length distribution, such as stearylamine, tallow fatty amine, behenylamine under a protective gas atmosphere, such as nitrogen at a temperature of 120 to 135 ° C, preferably 130 ° C, by continuous, metered addition of Urea is reacted with ammonia evolution.
  • a higher-chain alkylamine RNH 2 such as, for example, hexadecylamine, Octadecylamine, docosylamine, eicosylamine or especially the technical fatty alkylamines with a natural chain length distribution, such as stearylamine, tallow fatty amine, behenylamine under
  • a content of free fatty alkylamine of more than 1% would lead to yellowing on the finished textile, and a content of more than 0.5% biuret would significantly deteriorate the feel of the textile material.
  • the plasticizer emulsions according to the invention show excellent stability and heat storage stability over a period of 6 months at room temperature and over 3 months at a temperature of 50 ° C., without causing thixotropic effects. They also create a handle with extremely high fullness on the treated textile materials made of cotton and rayon wool, which leads to a wool-like handle behavior, especially with blends of synthetic and cellulose fibers. They are compatible with other post-treatment agents and optical brighteners in a bath.
  • the plasticizer emulsions according to the invention in combination with known glyoxal / urea resin systems significantly increase the crease angles wet and dry of the textile materials finished with them, which is of considerable importance for the wearing behavior of the finished textiles.
  • the plasticizer emulsions according to the invention are used as usual, i.e. the textiles to be finished are treated at from 80 to 130 ° C., preferably from 100 to 120 ° C., with liquors which contain 5 to 30 g / l, preferably 10 to 25 g / 1, of a plasticizer emulsion according to the invention.
  • the treatment with the liquor can be carried out in any desired manner, e.g. by spraying, splashing, diving, padding, etc.
  • the treatment if appropriate with subsequent squeezing, is carried out in such a way that a liquor absorption of 80 to 60% by weight takes place. It is then dried, preferably at 100 to 125 ° C.
  • other equipment, optical brighteners etc. can also be applied together with the plasticizer emulsion according to the invention.
  • 60 g of the product produced are fused with 15 g of the ammonium salt of the sulfuric acid half ester of the reaction product from oleyl alcohol with 23 mol of ethylene oxide at a temperature of 80 to 90 ° C. to form a homogeneous melt and condensed at 80 to 90 ° C. for 30 minutes.
  • the pH is then adjusted to between 6 and 7 using triethanolamine and using an Ultra-Turrax T 45 homogenizer from the company
  • the emulsion produced can be stored at 50 ° C for at least 6 weeks without changing the viscosity.
  • a cotton / polyester blend of 65 parts of cotton and 35 parts of polyester with a weight of 100 g / m 2 is impregnated with a finishing liquor which contains 25 g / 1 of the plasticizer emulsion prepared according to Example 1.
  • the soaked tissue is squeezed to a liquor pick-up of 60% and dried at 100 ° C. for 8 minutes.
  • a fabric with an equipped wool-like, full and voluminous handle is obtained.
  • the crease angle is determined dry (according to DIN 53 830) after 30 seconds of relief and the crease angle wet after 3 minutes of relief on a cell wool fabric with different equipment.
  • N-octadecylurea 136 g (0.5 mol) of N-octadecylurea are melted with 17.3 g (0.051 mol) of beenamide at a temperature of 120 to 130 ° C. to form a clear, homogeneous melt and admixed with 1.1 g of triethanolamine.
  • the storage stability of the emulsion is 18 days at 50 ° C.
  • Products can be produced in an analogous manner in which n-butyl glycol, ethyl glycol or n-propyl glycol are used.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP83111631A 1982-11-30 1983-11-22 Emulsion adoucissante, procédé pour sa préparation et son utilisation Withdrawn EP0112496A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19823244265 DE3244265A1 (de) 1982-11-30 1982-11-30 Weichmacheremulsion, verfahren zu ihrer herstellung und ihre anwendung
DE3244265 1982-11-30

Publications (2)

Publication Number Publication Date
EP0112496A2 true EP0112496A2 (fr) 1984-07-04
EP0112496A3 EP0112496A3 (fr) 1986-10-22

Family

ID=6179435

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83111631A Withdrawn EP0112496A3 (fr) 1982-11-30 1983-11-22 Emulsion adoucissante, procédé pour sa préparation et son utilisation

Country Status (8)

Country Link
US (1) US4488974A (fr)
EP (1) EP0112496A3 (fr)
JP (1) JPS59112074A (fr)
KR (1) KR840006838A (fr)
DE (1) DE3244265A1 (fr)
ES (1) ES527642A0 (fr)
PT (1) PT77555B (fr)
ZA (1) ZA838878B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000041500A3 (fr) * 1999-01-11 2001-02-15 3M Innovative Properties Co Compositions d'appret de filature anti-salissure
EP2594284A1 (fr) 2006-04-21 2013-05-22 Amgen Inc. Formulations peptide-anticorps thérapeutiques lyophilisées

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5085892A (en) * 1990-02-07 1992-02-04 Ethyl Corporation Laundry dryer sheet
FR2693206B1 (fr) * 1992-07-02 1994-09-16 Oreal Utilisation dans des solutions d'agents tensioactifs de carbamates d'aminopolyols en tant qu'épaississants et compositions les contenant.

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2313742A (en) * 1940-09-24 1943-03-16 Du Pont Process of treating textile fiber
US2477346A (en) * 1946-06-28 1949-07-26 Du Pont Methylol-behenamide and related compounds
DE1594949A1 (de) * 1966-02-25 1969-09-18 Cassella Farbwerke Mainkur Ag Verfahren zur Knitterfestausruestung von Textilien aus Cellulosefasern und von cellulosefaserhaltigen Mischtextilien
DE1934177A1 (de) * 1968-07-29 1970-02-05 Hoechst Ag Textilweichmachungsmittel
US3875197A (en) * 1968-07-15 1975-04-01 Hoechst Ag Amido-methyl-polyglycol formals
DE2320302B2 (de) * 1973-04-21 1975-05-22 Basf Ag, 6700 Ludwigshafen Gemische aus Methylol-alkylharrtstoffen und deren Butyläthern, Verfahren zu deren Herstellung und deren Verwendung
US3990847A (en) * 1971-09-07 1976-11-09 United Merchants And Manufacturers, Inc. Creaseproofing composition

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE793339A (fr) * 1970-10-20 1973-06-27 Henkel & Cie Gmbh Agent de traitement complementaire du linge et son procede de preparation
LU73633A1 (fr) * 1975-10-23 1977-05-31
US4272413A (en) * 1979-11-26 1981-06-09 Colgate-Palmolive Company Dialkylurea textile softening and antistatic agents

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2313742A (en) * 1940-09-24 1943-03-16 Du Pont Process of treating textile fiber
US2477346A (en) * 1946-06-28 1949-07-26 Du Pont Methylol-behenamide and related compounds
DE1594949A1 (de) * 1966-02-25 1969-09-18 Cassella Farbwerke Mainkur Ag Verfahren zur Knitterfestausruestung von Textilien aus Cellulosefasern und von cellulosefaserhaltigen Mischtextilien
US3875197A (en) * 1968-07-15 1975-04-01 Hoechst Ag Amido-methyl-polyglycol formals
DE1934177A1 (de) * 1968-07-29 1970-02-05 Hoechst Ag Textilweichmachungsmittel
US3990847A (en) * 1971-09-07 1976-11-09 United Merchants And Manufacturers, Inc. Creaseproofing composition
DE2320302B2 (de) * 1973-04-21 1975-05-22 Basf Ag, 6700 Ludwigshafen Gemische aus Methylol-alkylharrtstoffen und deren Butyläthern, Verfahren zu deren Herstellung und deren Verwendung

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000041500A3 (fr) * 1999-01-11 2001-02-15 3M Innovative Properties Co Compositions d'appret de filature anti-salissure
US6537662B1 (en) 1999-01-11 2003-03-25 3M Innovative Properties Company Soil-resistant spin finish compositions
EP2594284A1 (fr) 2006-04-21 2013-05-22 Amgen Inc. Formulations peptide-anticorps thérapeutiques lyophilisées
EP2594285A1 (fr) 2006-04-21 2013-05-22 Amgen Inc. Formulations peptide-anticorps thérapeutiques lyophilisées
EP2594287A1 (fr) 2006-04-21 2013-05-22 Amgen Inc. Formulations peptide-anticorps thérapeutiques lyophilisées
EP2594286A1 (fr) 2006-04-21 2013-05-22 Amgen Inc. Formulations peptide-anticorps thérapeutiques lyophilisées
EP2594288A1 (fr) 2006-04-21 2013-05-22 Amgen Inc. Formulations peptide-anticorps thérapeutiques lyophilisées

Also Published As

Publication number Publication date
US4488974A (en) 1984-12-18
DE3244265A1 (de) 1984-05-30
ES8502184A1 (es) 1984-12-16
EP0112496A3 (fr) 1986-10-22
JPS59112074A (ja) 1984-06-28
PT77555A (de) 1983-11-01
ZA838878B (en) 1984-07-25
DE3244265C2 (fr) 1991-11-21
PT77555B (de) 1986-02-12
KR840006838A (ko) 1984-12-03
ES527642A0 (es) 1984-12-16

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