US2149709A - Textile assistants - Google Patents

Textile assistants Download PDF

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Publication number
US2149709A
US2149709A US7819536A US2149709A US 2149709 A US2149709 A US 2149709A US 7819536 A US7819536 A US 7819536A US 2149709 A US2149709 A US 2149709A
Authority
US
United States
Prior art keywords
textile
dicyandiamide
assistants
grams
hydrochloride
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 - Lifetime
Application number
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English (en)
Inventor
Rein Herbert
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Application granted granted Critical
Publication of US2149709A publication Critical patent/US2149709A/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07—Organic amine, amide, or n-base containing
    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2352—Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric

Definitions

  • This invention relates to a new kind of assistants for the textile industry.
  • a further object is a new process of softening textile fibers of animal and vegetable origin.
  • R1 and B may be, for instance, decylamine, octadecylamine, benzylamine, oleylamine, isopropyldodecylamine, dodecylamine stearylor cyclohexylamine.
  • the compounds are made, for instance, by the action of dicyandiamide on the salt of a primary or secondary aliphatic, aromatic or hydroaromatic amine at a raised temperature.
  • the start--v ing materials may be boiled in an aqueous alcoholic solution or they may be melted together at a temperature say between 120 and 160 C. In many cases it is not necessary to isolate the compounds, since the products of reaction may be used directly in a crude condition.
  • Example 1 Artiflcial silk in 'skeins is brightened by means of a warm solution containing 5 grams of octodecylbiguanlde per liter. The grip of the silk is softened and becomes more fluid and the working up of the silk is improved.
  • Example 2 -2 parts ofcastor oil and 1 part of laurylbiguanide are stirred in a stirring or heating apparatus to produce a homogeneous mixture. 0n diluting with water there is obtained a stable highly dispersed emulsion which may be used for lubricating, softening and the like purposes.
  • Example 3.-Raw still sized cotton shirtings which cannot be wetted with hot water are immediately thoroughly wetted in a bath to which 2 55 grams of isopropyldodecylbiguanide have been added, whereby the successive operations, such as de-sizing and the like, can be carried out with an essentially better result and with enhanced certainty.
  • Example 4.-1.1 molecular proportions of dicyandiamide are melted with one molecular proportion of stearylarnine hydrochloride in an oil bath at to C. for 6 to 8 hours while stirring. There is produced a brownish thickly liquid mass which, when introduced into water, yields a strongly foaming solution and can be used as such in hot condition.
  • Example 5 1-1.1 molecular proportions of dicyandiamide are melted with 1 molecular proportion of dodecylmethylamine hydrochloride as described in the preceding example, whereby dodecylmethyl-biguanide is produced.
  • Example 6 grams of dicyandiamide are boiled with 290 grams of dodecylamine hydrochloride in methanolic solution for 12 hours under reflux. After distillation of the alcohol there is obtained a mass which has the appearance of soft soap, consists mainly of dodecyl-biguanide and shows a strong biuret reaction.
  • Example 7 grams of diethylenediamine hydrochloride are boiled with grams of dicyandiamide in methanolic solution for 12 hours under reflux and worked up as described in the preceding example. This compound is particularly useful as a wetting agent.
  • Example 8.1 molecular proportion of benzylamine hydrochloride is boiled with 1 molecular proportion of dicyandiamide in methanolic solution for 12 hours, whereby benzyl-biguanide is produced.
  • Example 9.-1 molecular proportion of hexahydroaniline hydrochloride and 1 molecular proportion of dicyandiamide are boiled in methanolic solution as described above, whereby cyclohexylbiguanide is produced.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US7819536 1935-05-09 1936-05-06 Textile assistants Expired - Lifetime US2149709A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1935I0052281 DE694130C (de) 1935-05-09 1935-05-09 Netz-, Emulgier- und Weichmachungsmittel

Publications (1)

Publication Number Publication Date
US2149709A true US2149709A (en) 1939-03-07

Family

ID=89834536

Family Applications (1)

Application Number Title Priority Date Filing Date
US7819536 Expired - Lifetime US2149709A (en) 1935-05-09 1936-05-06 Textile assistants

Country Status (4)

Country Link
US (1) US2149709A (de)
DE (1) DE694130C (de)
FR (1) FR805768A (de)
GB (1) GB475039A (de)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2455897A (en) * 1945-10-12 1948-12-07 American Cyanamid Co 1, 5-diarylbiguanides from aromatic amines and dicyanimide
US2455896A (en) * 1945-10-12 1948-12-07 American Cyanamid Co 1-aryl, 5-alkyl, biguanides
US2467371A (en) * 1944-05-10 1949-04-19 Ici Ltd Biguanide derivatives
US2482710A (en) * 1945-03-24 1949-09-20 American Cyanamid Co Process of reacting dicyandiamide and aniline
US2577593A (en) * 1946-12-21 1951-12-04 Du Pont Stabilizing cellulose yarns
US2622075A (en) * 1946-12-03 1952-12-16 Sandoz Ltd Polyamine-cyanamide resins
US2961377A (en) * 1957-08-05 1960-11-22 Us Vitamin Pharm Corp Oral anti-diabetic compositions and methods
US3059029A (en) * 1959-10-29 1962-10-16 U S Vitamin And Pharmaceutical Process for alkyl and aralkyl biguanides
US3080423A (en) * 1958-08-20 1963-03-05 Proske Gerhard Process for the manufacture of the acid-addition salts of n-butylbiguanide

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE740539C (de) * 1938-05-13 1943-10-29 Ig Farbenindustrie Ag Behandlung von Faserstoffen
DE741891C (de) * 1938-09-10 1943-11-18 Zschimmer & Schwarz Chem Fab D Verfahren zur Herstellung wasserloeslicher stickstoffhaltiger Kondensationsprodukte
DE872788C (de) * 1939-12-21 1953-04-09 Geigy Ag J R Verfahren zur Darstellung von wasserloeslichen, hoehermolekularen Acylbiguaniden
DE914490C (de) * 1950-01-13 1954-07-05 Bayer Ag Verfahren zur Erhoehung des Gebrauchswertes von Textilien

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2467371A (en) * 1944-05-10 1949-04-19 Ici Ltd Biguanide derivatives
US2482710A (en) * 1945-03-24 1949-09-20 American Cyanamid Co Process of reacting dicyandiamide and aniline
US2455897A (en) * 1945-10-12 1948-12-07 American Cyanamid Co 1, 5-diarylbiguanides from aromatic amines and dicyanimide
US2455896A (en) * 1945-10-12 1948-12-07 American Cyanamid Co 1-aryl, 5-alkyl, biguanides
US2622075A (en) * 1946-12-03 1952-12-16 Sandoz Ltd Polyamine-cyanamide resins
US2577593A (en) * 1946-12-21 1951-12-04 Du Pont Stabilizing cellulose yarns
US2961377A (en) * 1957-08-05 1960-11-22 Us Vitamin Pharm Corp Oral anti-diabetic compositions and methods
US3080423A (en) * 1958-08-20 1963-03-05 Proske Gerhard Process for the manufacture of the acid-addition salts of n-butylbiguanide
US3059029A (en) * 1959-10-29 1962-10-16 U S Vitamin And Pharmaceutical Process for alkyl and aralkyl biguanides

Also Published As

Publication number Publication date
GB475039A (en) 1937-11-08
DE694130C (de) 1940-07-26
FR805768A (fr) 1936-11-28

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