GB650940A - Improvements in or relating to the production of water-soluble derivatives of dialkylolamides of dimerized polyunsaturated fatty acids - Google Patents

Improvements in or relating to the production of water-soluble derivatives of dialkylolamides of dimerized polyunsaturated fatty acids

Info

Publication number
GB650940A
GB650940A GB14653/47A GB1465347A GB650940A GB 650940 A GB650940 A GB 650940A GB 14653/47 A GB14653/47 A GB 14653/47A GB 1465347 A GB1465347 A GB 1465347A GB 650940 A GB650940 A GB 650940A
Authority
GB
United Kingdom
Prior art keywords
dimerized
acid
mols
ethylene oxide
fatty acids
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB14653/47A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB650940A publication Critical patent/GB650940A/en
Expired legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642Compounds containing nitrogen
    • D06P1/649Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • D06P1/6496Condensation products from carboxylic acids and hydroxyalkyl amine (Kritchewski bases)

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

Water-soluble condensates are prepared by condensing dialkylolamides of dimerized polyolefinic fatty acids of the general formula <FORM:0650940/IV (a)/1> wherein R is the residue of a dimerized polyolefinic fatty acid whose monomer contains 18-20 carbon atoms, n is a whole number from 2 to 4, R1 is hydrogen or the radical -CnH2n OH, with a sufficient quantity of an alkylene oxide having 2 to 4 carbon atoms to render the product soluble, said quantity of alkylene oxide being at least 8 mols. per mol. of the dimer acid diamide. Condensation may be effected in the presence of polar solvents such as isopropanol or t-butanol. Starting materials include the di-alkylolamides derived from mono- and di-ethanolamines, ethanol-propanolamine, ethanol-butanolamine, propanolamine and butanolamine and dimerized cottonseed fatty acids, linseed fatty acids, soya bean fatty acids, tung oil fatty acids, hydrated castor oil fatty acids and fish oil fatty acids. The examples illustrate the process using ethylene oxide and products containing up to 175 ethenoxy units are prepared; reference is made to the use of propylene and butylene oxides. The products may be used as dispersing and emulsifying agents and in dyeing textile materials with a preformed metallized dye soluble in an acid bath, examples being given (see Group IV (c)). Specification 650,939, [Group IV (b)], is referred to.ALSO:Water-soluble derivatives of dialkylolamides of dimerized polyolefinic fatty acids of the general formula <FORM:0650940/IV (b)/1> wherein R is the residue of a dimerized polyolefinic fatty acid, the monomer of which contains 18-20 carbon atoms, n is a whole number from 2 to 4, R1 is hydrogen or the radical -CnH2nOH, are prepared by condensing the dialkylolamide with a sufficient quantity of an alkylene oxide having 2 to 4 carbon atoms to render the product water-soluble, said quantity of alkylene oxide being at least 8 mols. per mol. of the dimer acid diamide. The condensation may be effected in the absence of solvents by heating the dimer acid diamide with ethylene, propylene or butylene oxide in an autoclave under pressure, preferably in the presence of an alkaline condensation catalyst such as sodium alcoholate at 100-160 DEG C.; alternatively, condensation may be effected at lower temperatures and generally at atmospheric pressure by use of polar solvents such as isopropanol or t-butanol, preferably with the addition, as catalyst, of a lower alkylamine such as di- or tri-ethylamine, and then the alkylene oxide may be passed into the solution of amide under reflux conditions. The amount of alkylene oxide required for optimum results may vary widely; with the lower molecular weight diamides, such as the bis-ethanolethanolamides, as little as 8 mols. of ethylene oxide, 10-15 mols. of propylene oxide and 15-25 mols. of butylene oxide for each mol. of dimer acid diamide will produce adequate water-solubility. The products are stated to have good dispersing and emulsifying properties and to be valuable as assistants in dyeing processes employing preformed metallized dyes in an acid dye bath (see Group IV (c)). The alkylol amides employed as starting materials may be prepared by the method described in Specification 650,939, and from the various reactants therein specified. According to typical examples: (1) N,N1-di-2-hydroxyethylamide of dimerized cottonseed fatty acid (190 gms.) in t-butanol is heated under reflux in presence of triethylamine and ethylene oxide (244 gms.) bubbled through the solution over 12 hours, after which solvent and unreacted material is distilled off, leaving a dark viscous liquid product; (2) as in (1) using 21 gms. ethanol amide and 266 gms. ethylene oxide, the product obtained containing 175 ethenoxy units per molecule, the bis-diethanolamide of dimerized cottonseed fatty acid is similarly reacted with 16 mols. of ethylene oxide; (3) bis-monoethanolamide of dimerized linseed fatty acid (0.151 mol.) is similarly reacted with ethylene oxide until 2.84 mols. have been absorped, the product being a dark red oil; (4) bis-monoethanolamide of dimerized tung fatty acid (0.156 mol.) is reacted as in (1) with in one case 2.93 mols. ethylene oxide and in another case with 4.95 mols. ethylene oxide both products being dark oils; (5) the reaction of (1) is repeated using 0.149 mol. of bis-monopropanolamide of dimerized cottonseed fatty acid and 3.86 mols. of ethylene oxide. In these examples, the alkylolamides are prepared by refluxing a xylene solution containing 1 mol. of the dimerized acid or its dimethyl ester and 2 mols. of monoethanolamine while distilling off the water produced and sometimes an additional 10 per cent molecular excess of the amine is added near the end of the reaction since some of the amine may tend to distil off with the water.ALSO:Textile materials are dyed with a preformed metallized dye soluble in an acid bath containing the dye and a water-soluble derivative of a dialkylol amide prepared by condensing a dialkylolamide having the general formula <FORM:0650940/IV (c)/1> wherein R is the residue of a dimerized polyolefinic fatty acid the monomer of which contains 18-20 carbon atoms, n is a whole number from 2 to 4 inclusive, and R1 is hydrogen or -CnH2nOH, with a sufficient quantity of an alkylene oxide having 2-4 carbon atoms to render the product soluble, said quantity being at least 8 mols. per mol. of dimer acid diamide (see Group IV (b)). According to examples (9)-(11), wool yarn is dyed in an aqueous acid dye bath containing as dyeing assistant the product obtained by reacting N,N1 - di - 2 - hydroxyethylamide of dimerized cotton seed fatty acid (190 gms.) and ethylene oxide (244 gms.) and as dye stuff (a) the chromium complex of the azo dyestuff from diazotized anthranilic acid and 1-(41-sulphophenyl)-3-methyl-5-pyrazolone, (b) said chromium complex, diazotized 1 - amino - 2 - hydroxynaphthalene - 4 - sulphonic acid coupled to 1 - phenyl - 3 - methyl - 5 - pyrazolone and diazotized 1 - amino - 2 - hydroxy - naphthalene - 4 - sulphonic acid coupled to 1-hydroxy - naphthalene - 8 - sulphonic acid, and (c) the chromium complex of the azo dyestuff obtained from diazotized 1-amino-2-hydroxy - 6 - nitro - naphthalene - 4 - sulphonic acid coupled to 2-naphthol, respectively, and to example 12; wool yarn is dyed in an acid bath containing the chromium complex of the azo dyestuff obtained from diazotized 4-nitro-2-amino-phenol coupled to 1-(41-sulphophenyl)-3 - methyl - 5 - pyrazolone and as assistant the product obtained by reacting the bis-monoethanolamide of dimerized linseed oil fatty acid (0.151 mol.) and ethylene oxide (2.84 mols.). The resulting dyeing shows improved brightness, levelness and strength of shade as compared with the same dyeing carried out in the absence of the alkylolamide products. Other alkylolamide products mentioned are the ethylene oxide, propylene oxide and butylene oxide condensation products derived from bis - ethanolamides, propanolamides, butanolamides, ethanol-propanol amides and ethanol-butanol amides of dimerized fatty acids from cottonseed oil, soya bean oil, dehydrated castor oil, linseed oil, tung oil and fish oils. The products also have dispersing and emulsifying properties.
GB14653/47A 1946-06-18 1947-06-03 Improvements in or relating to the production of water-soluble derivatives of dialkylolamides of dimerized polyunsaturated fatty acids Expired GB650940A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US650940XA 1946-06-18 1946-06-18

Publications (1)

Publication Number Publication Date
GB650940A true GB650940A (en) 1951-03-07

Family

ID=22060292

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14653/47A Expired GB650940A (en) 1946-06-18 1947-06-03 Improvements in or relating to the production of water-soluble derivatives of dialkylolamides of dimerized polyunsaturated fatty acids

Country Status (1)

Country Link
GB (1) GB650940A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114426815A (en) * 2022-01-18 2022-05-03 中国石油化工股份有限公司 Oil-based drilling fluid suitable for strong water-sensitive and easily-collapsed stratum and preparation method and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114426815A (en) * 2022-01-18 2022-05-03 中国石油化工股份有限公司 Oil-based drilling fluid suitable for strong water-sensitive and easily-collapsed stratum and preparation method and application thereof

Similar Documents

Publication Publication Date Title
US1985424A (en) Alkylene-oxide derivatives of polyhydroxyalkyl-alkylamides
US2272489A (en) Nitrogenous condensation products and a process of producing same
US2274831A (en) Polyamides and process for their preparation
US3138610A (en) Substituted imidazolines
US3686151A (en) Terpolymers of diallylamine
US2235480A (en) Amidelike derivatives and process of making the same
US3226395A (en) Water-insoluble phthalocyanine dyestuffs and process for their manufacture
US1923178A (en) Hydroxy alkyl ethers of tertiary amines and process of preparing same
US2047069A (en) Amides
US2370031A (en) Process for improving fibrous material and the material treated by such process
US3933871A (en) Fabric softener compound and processes for preparing and using the same
US1952008A (en) Emulsifying detergent and wetting agent
US2967755A (en) Leveling and stripping agents
GB650940A (en) Improvements in or relating to the production of water-soluble derivatives of dialkylolamides of dimerized polyunsaturated fatty acids
US2470081A (en) Alkylene oxide condensation products of dimerized fatty acid alylol amides
US3028402A (en) High molecular nitrogen condensation products
US2483969A (en) Acyl polyalkylene-polyamine biguanides
US2525770A (en) Baths for stripping vat-dyed textile materials and agents useful therein
EP0225282B1 (en) Process for the post-treatment of dyed cellulosic fibrous material
US3912780A (en) Substituted methylene diamines
US2382185A (en) Nitrogenous condensation products
US2385940A (en) Amino-methylene derivatives of salicylamide and process therefor
US2984539A (en) Process for dyeing polyacrylonitrile material
US2847461A (en) Condensation products of p-aminosalicylic acid
US2009396A (en) Methods for their preparation