US2936251A - Amido carboxylic acids - Google Patents

Amido carboxylic acids Download PDF

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Publication number
US2936251A
US2936251A US700744A US70074457A US2936251A US 2936251 A US2936251 A US 2936251A US 700744 A US700744 A US 700744A US 70074457 A US70074457 A US 70074457A US 2936251 A US2936251 A US 2936251A
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Prior art keywords
acid
mol
water
mols
compounds
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US700744A
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English (en)
Inventor
Bertram J Garceau
Charles A Robinson
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Arnold Hoffman & Co Inc
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Arnold Hoffman & Co Inc
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Priority to BE573541D priority Critical patent/BE573541A/xx
Application filed by Arnold Hoffman & Co Inc filed Critical Arnold Hoffman & Co Inc
Priority to US700744A priority patent/US2936251A/en
Priority to FR780958A priority patent/FR1216561A/fr
Application granted granted Critical
Publication of US2936251A publication Critical patent/US2936251A/en
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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
    • D06M13/405—Acylated polyalkylene polyamines
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31935—Ester, halide or nitrile of addition polymer

Definitions

  • This invention relates to new organic compounds having a free carboxyl group.
  • Another object is to provide new anionic products which are suitable for treating textiles.
  • a further object is to provide agents which will give improved anti-soiling properties to textiles.
  • R and R are aliphatic hydrocarbon radicals having at least carbon atoms, R and R are -CH CH or CH2CH2CH2- OI CH2CH- and n is an integer from 4 to 8 inclusive.
  • R and R are aliphatic hydrocarbon radicals having 5 to 17 carbon atoms.
  • R and R can be saturated aliphatic hydrocarbon radicals or ethylenically unsaturated aliphatic hydrocarbon radicals.
  • Typical examples of compounds coming withinthe instant invention are N,N-di-(stearamidoethyl)-adipamic acid, N,N-di-(stearamidoethyl)-azelaarnic acid, N,N-di- (stearamidoethyl)-sebacamic acid, N,N-di-(caprylamidoethyl) sebacarnic acid, N,N di (olearnidoethyD-azelamic acid, N,N-di-(stearamidopropyl)-adipamic acid, N- stearamidoethyl-N-caproamidoethyl-adipamic acid, N,N- di-(stearamidoisopropyl)-sebacamic acid, N,N-di-(stearamidoethyD-pimelamic acid, N,N-di-(stearamidoethyl)- suberamic acid
  • the compounds of the present invention are anionic in nature and are useful in the treatment of textiles. They provide inexpensive, highly effective textile lubricants and softeners and impart anti-soiling properties to textile carpet yarns and fibers.
  • the compounds of the present invention being half amides of dicarboxylic acids, differ from the full amides in having a free carboxyl group present in the molecule. It is this free carboxyl group which forms alkali metal 2,936,251 Patented May to, 1960 salts, thus rendering the molecule truly anionic.
  • the full amides on the other hand cannot form salts and cannot be used directly to form anionic textile treating agents, but instead must be modified by the incorporation of alkali soaps and the like. It has been found that the anionic half amides of the present invention are preferred over the corresponding non-anionic full amides as softeners for wool, antisoiling finishes for carpets, and for use in conjunction with other anionic textile finishing agents.
  • the compounds of the present invention are frequently prepared and used in the form of the free acids, they are also frequently used in the form of their alkali metal salts, e.g., potassium and sodium salts such as sodium N,N-di-(stearamidoethyl)-adipamate, potassium N,N-di-(stearamidoethyl)-azelaarnate, sodium N,N-di- (oleamidopropyl)-sebacamate, etc.
  • the alkali metal salts are considered the full equivalents of the free acids, therefore.
  • the compounds of the present invention are readily formed by condensing an amido amine containing two amide groups and one secondary amino group With an equimolar quantity of a dicarboxylic acid according to the equation:
  • the anhydride, ester or acyl halide thereof in place of the free dicarboxylic acid, there can be employed the anhydride, ester or acyl halide thereof.
  • a hydrolyzing agent normally must be added to form the free acid group on the finished product.
  • the condensation of the amido amine with the dicarboxylic acid is normally carried out at an elevated temperature, sufi'iciently high to cause the evolution of one mol of Water, e.g., to 225 0., preferably C. to 205 C.
  • the water formed in the reaction can be removed with the aid of an inert azeotroping agent, e.g., aliphatic and aromatic hydrocarbons such as xylene, benzene, toluene, hexane, etc.
  • amido amines employed as starting materials for the most part are old compounds and can be prepared by the condensation of one mol of the ap; ropriate di alkylenetriamine with two mols of a fatty acid.
  • Unsymmetrically substituted amido amines (R and. R are different) can be prepared by the condensation of the dialkylenetriamine first with an equimolar quantity of one fatty acid and then with an equimolar quantity of a different fatty acid.
  • dialkylenetriarnine there can be used diethylenetriamine, dipropylenetriamine (3,3'-iminobispropylamine) and diisopropylenetriamine.
  • saturated fatty acids such as caproic, capyrlic, capric, pelargonic, myristic, lauric, palmitic, stearic, or hydrogenated animal and vegetable fatty acids or unsaturated fatty acids such as oleic, linoleic, eleostearic acid, etc.
  • Mixtures of fatty acids can be used, such as the mixtures obtained by saponifying animal and vebetable fats and oils, e.g., cottonseed oil, soybean oil,-' peanut oil, fish oil, hydrogenated' peanut oil, hydrogenated soybean oil, linseed oil, etc.
  • alkylene dicarboxylic acids there can be used adipic, pimelic, azelaic, suberic and sebacic acids.
  • an amide amine of the type set forth above is heated with an equimolar quantity of the alkylene dicarboxylic acid at a temperature sufliciently high to cause the evolution of one molecular equivalent of water.
  • one mol of the dialkylenetriamine is heated With two molecular equivalents of a monocarboxylic acid of the type set forth until two mols of water have been evolved.
  • one mol of the alkylene dicarboxylic acid is added at such a temperature that no reaction occurs until all of the dicarboxylic acid has been added, after which the mixture is heated until the evolution of water is complete.
  • the yields of the desired semi-amides are essentially quantitative.
  • N,N-(iminodiethylene) bisstearamide prepared by the condensation of two mols of stearic acid with one mol of diethylenetriamine, was mixed with one molecular equivalent of adipic acid and heated with stirring at 200 to 205 C.
  • the amount of water evolved increased to one mol per mol of adipic acid employed and the neutral equivalent of the product increased to the theoretical value.
  • the products of the invention are light in color and range from viscous liquids to hard, brittle, wax-like solids.
  • the alkali metal salts, e.g., the sodium, potassium, rubidium and caesium salts, of the products are either soluble or dispersible in water.
  • alkali metal salts of the products are converted by conventional procedures to homogeneous aqueous pastes, which can be readily dissolved or dispersed in water. These products are outstanding in their softening effect on textile fabrics. They are also useful as lubricating agents for yarns and textile constructions and are particularly valuable as soilresistant lubricants for carpeting.
  • a paste of the potassium salt of the product was prepared by adding 73.6 g. of the molten amide-acid in 12 g. of diethylene glycol to a solution of 8.0 g. of potassium hydroxide in 200 g. of water at 65 C. with constant agitation.
  • the resulting homogeneous gel formed a soft paste on cooling which was easily dispersible in warm water.
  • a paste of the potassium salt of this product was prepared by adding a mixture of 79 g. of the amido acid in 39 g. of diethylene glycol at about 105 C. to 196 g. of 3.7% aqueous potassium hydroxide solution at about 50 C. with agitation. On cooling, a nearly colorles s, homogeneous paste was obtained.
  • One percent of this anionic paste applied to swatches of wool, cotton, Dacron (polyethylene terephthalate) and Orlon (an acrylonitrile polymer) by padding from an aqueous soluprovement inthe softness of the fabrics. Fabrics treated in this manner exhibited excellent resistance to scorching and yellowing andshowed essentially no chlorine retention.
  • Example 10 N,N-di-(slearamidoethyl)-adipamic acid The procedure of Example 1 was followed except that 70 g. of xylene was added to the reaction mixture as an azeotroping agent. The mixture was allowed to reflux gently until 10 g. of water had collected in the Dean- Stark tube. After removing the xylene by distillation under vacuum, the hard, wax-like solid had a neutral equivalent of 685.
  • R and R are aliphatic hydrocarbon radicals having at least 5 carbon atoms, R and R are selected from the group consisting of -CH CH -CH CH CH and and n is an integer from 4 to 8 inclusive.
  • R and R are 5.
  • R and R are aliphatic hydrocarbon radicals having 5 to 17 carbon atoms.
  • R and R are saturated aliphatic hydrocarbon radicals having 5 to 17 carbon atoms.
  • R and R are ethylenically unsaturated aliphatic hydrocarbon radicals.
  • a process of making the compounds of claim 1 comprising reacting one mol of a dialkylene triamine having 2 to 3 carbon atoms in the alkylene group with two mols of a fatty acid having at least 6 carbon atoms to form a diamide and reacting the diamide thus formed with one mol of an alkylene dicarboxylic acid having 4 to 8 carbon atoms in the alkylene group to form a half amide of the dicarboxylic acid.
  • a method of imparting anti-soiling properties to textile fibers comprising applying to the textile fibers the compound of claim 1.
  • a method according to claim 10 wherein the fibers are cellulosic fibers.
  • a method according to claim 10 wherein the fibers are polyester fibers.
  • a method according to claim 10 wherein the fibers are polyamide fibers.
  • a process of making a half amide of a dicarboxylic acid comprising reacting one mol of an amide having the formula:
  • R and R are aliphatic hydrocarbon radicals .from the group consisting of -CH CH 4 8 having 5 to 17 carbon atoms and R and R are selected References Cited in the file of this patent UNITED STATES 15ATENTS -CH2CH2CH2 I 5 2,609,381 Goldstem et a1. Sept. 2, 1952 cm FOREIGN PATENTS with an alkylene dicarboxylic acid having 4 to 8 carbon 738,379 Great Britain Oct. 12, 1955 atoms in the alkylene group.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US700744A 1957-12-05 1957-12-05 Amido carboxylic acids Expired - Lifetime US2936251A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BE573541D BE573541A (en:Method) 1957-12-05
US700744A US2936251A (en) 1957-12-05 1957-12-05 Amido carboxylic acids
FR780958A FR1216561A (fr) 1957-12-05 1958-12-05 Semi-amides d'acides dicarboxyliques convenant au traitement des textiles

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US700744A US2936251A (en) 1957-12-05 1957-12-05 Amido carboxylic acids

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3329608A (en) * 1963-04-23 1967-07-04 Ciba Ltd Aqueous preparations of salts of n, n-disubstituted acid amides of di- or tricarboxylc acids
US3465036A (en) * 1964-07-07 1969-09-02 American Cyanamid Co 2-carboxyethoxymethyl-tris (2-(n-methylolcarbamoyl)-ethoxymethyl) methane
US4057673A (en) * 1974-10-09 1977-11-08 Colgate Palmolive Company Fabric conditioning with improved composition containing a plasticizer
US6004914A (en) * 1998-08-20 1999-12-21 Mona Industries, Inc. Amphoteric derivatives of aliphatic polyamines with fatty acids, esters or triglycerides, which are useful for various consumer products and industrial applications

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2609381A (en) * 1949-10-05 1952-09-02 Sun Chemical Corp Amido-amide derivatives of dibasic acids and processes of preparing the same
GB738379A (en) * 1951-03-02 1955-10-12 Boehme Fettchemie Gmbh Improvements in and relating to the treatment of textile materials

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2609381A (en) * 1949-10-05 1952-09-02 Sun Chemical Corp Amido-amide derivatives of dibasic acids and processes of preparing the same
GB738379A (en) * 1951-03-02 1955-10-12 Boehme Fettchemie Gmbh Improvements in and relating to the treatment of textile materials

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3329608A (en) * 1963-04-23 1967-07-04 Ciba Ltd Aqueous preparations of salts of n, n-disubstituted acid amides of di- or tricarboxylc acids
US3465036A (en) * 1964-07-07 1969-09-02 American Cyanamid Co 2-carboxyethoxymethyl-tris (2-(n-methylolcarbamoyl)-ethoxymethyl) methane
US4057673A (en) * 1974-10-09 1977-11-08 Colgate Palmolive Company Fabric conditioning with improved composition containing a plasticizer
US6004914A (en) * 1998-08-20 1999-12-21 Mona Industries, Inc. Amphoteric derivatives of aliphatic polyamines with fatty acids, esters or triglycerides, which are useful for various consumer products and industrial applications

Also Published As

Publication number Publication date
BE573541A (en:Method) 1900-01-01
FR1216561A (fr) 1960-04-26

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