GB755478A - Water-soluble organic nitrogen compounds - Google Patents

Water-soluble organic nitrogen compounds

Info

Publication number
GB755478A
GB755478A GB2242253A GB2242253A GB755478A GB 755478 A GB755478 A GB 755478A GB 2242253 A GB2242253 A GB 2242253A GB 2242253 A GB2242253 A GB 2242253A GB 755478 A GB755478 A GB 755478A
Authority
GB
United Kingdom
Prior art keywords
biguanide
bis
hydrogen atom
formula
water
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
GB2242253A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2242253A priority Critical patent/GB755478A/en
Publication of GB755478A publication Critical patent/GB755478A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20Derivatives 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
    • C07C279/24Y being a hetero atom
    • C07C279/26X and Y being nitrogen atoms, i.e. biguanides
    • C07C279/265X and Y being nitrogen atoms, i.e. biguanides containing two or more biguanide groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Coloring (AREA)

Abstract

Water-soluble organic nitrogen condensation products are obtained by heating, e.g. from 70 DEG C. to 200 DEG C., in the absence of water a salt of a biguanide of the formula A[NXC(NH). NH.C(NH).NH2]p, wherein p is 1 or 2, Z is a hydrogen atom or an alkyl, alkylene, aralkyl, aryl or arylene radical, which may contain one or more neutral or basic substituents, and X is a hydrogen atom or alkyl radical, with a linear polyalkyleneimine of the formula Y[(CH2)n. NH-]m-(CH2)n.NH2, wherein Y is NH2, OH or a halogen, n is 2 to 6 inclusive and m is an integer. Reactants specified are (a) salts, e.g. hydrochlorides, sulphates, acetates or carbonates, of biguanide, phenyl biguanide, m-phenylene - bis - biguanide, p - hydroxyphenylbiguanide, p - chlorophenylbiguanide, 1 : 1 - di-methylbiguanide and p-methoxyphenylbiguanide; (b) diethylene triamine, triethylene tetramine, tetraethylene pentamine, bis-hexamethylene triamine, 1 : 2 - bis - (omega - aminohexyl-amino)-ethane, and polyethyleneimines obtained by polymerizing ethyleneimine in the presence of hydrochloric acid, or derivatives thereof, e.g. the carbonates. The reaction may be effected in a solvent, e.g. butanol, b -ethoxyethanol or b -butoxyethanol. Examples are given. The new compounds which are viscous liquids are useful for treating cellulosic and polyamide textiles or fibres to improve their dyeability.ALSO:Water-soluble organic nitrogen condensation products are obtained by heating, e.g. from 70 DEG to 200 DEG C., in the absence of water a salt of a biguanide of the formula A[NXC(NH).NH.C (NH).NH2]p, wherein p is 1 or 2, A is a hydrogen atom or an alkyl, alkylene, aralkyl, aryl or arylene radical, which may contain one or more neutral or basic constituents, and X is a hydrogen atom or an alkyl radical, with a linear polyalkyleneimine of the formula Y[CH2)n.NH-]m -(CH2)n.NH2, wherein Y is NH2, OH or a halogen, n is 2 to 6 inclusive and m is an integer. Reactants specified are (a) salts, e.g. hydrochlorides, sulphates, acetates or carbonates of biguanide, phenyl biguanide, m-phenylene-bis-biguanide, p-hydroxyphenylbiguanide, p-chlorophenyl - biguanide, 1:1 - dimethyl - biguanide and p-methoxyphenyl-biguanide; (b) diethylene triamine, triethylene tetramine, tetraethylene pentamine, bis-hexamethylene triamine, 1:2-bis(omega-amino-hexyl-amino)-ethane, and polyethyleneimines obtained by polymerizing ethyleneimine in the presence of HCl, or derivatives thereof, e.g. the carbonates. The reaction may be effected in a solvent, e.g. butanol, b -ethoxy ethanol or b -butoxy ethanol. Examples are given. The new compounds which are viscous liquids are useful for treating cellulose and polyamide textiles or fibres to improve their dyeability.ALSO:Water-soluble organic nitrogen compounds obtained by condensation of a salt of a biguanide of the formula A[NXC(NH) NH C(NH)NH2]p, wherein p is 1 or 2, A is a hydrogen atom or an alkyl, alkylene, aralkyl, aryl arylene radical, which may contain one or more neutral or basic substituents, and X is a hydrogen atom or an alkyl radical, with a linear polyalkyleneimine of the formula Y[CH2)n NH-]m -(CH2)n NH2, wherein Y is NH2, OH or a halogen, n is 2 to 6 inclusive and m is a integer (see Group IV(a)), are useful for the treatment of cellulosic and polyamide textile materials or fibres to improve their dyeability. After treatment with the above compounds, applied e.g. from aqueous solution at 50 DEG to 100 DEG C., cellulosic textiles can be dyed with acid and chrome dyestuffs; polyamide materials so treated take up much more dyestuffs that are solubilized by means of anionic groups than the untreated materials. The compounds can also be used for aftertreating direct cotton dyeing, if desired in conjunction with metal salts, e.g. copper salts, to enhance the fastness of the dyeings. Examples are given.
GB2242253A 1953-08-14 1953-08-14 Water-soluble organic nitrogen compounds Expired GB755478A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2242253A GB755478A (en) 1953-08-14 1953-08-14 Water-soluble organic nitrogen compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2242253A GB755478A (en) 1953-08-14 1953-08-14 Water-soluble organic nitrogen compounds

Publications (1)

Publication Number Publication Date
GB755478A true GB755478A (en) 1956-08-22

Family

ID=10179107

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2242253A Expired GB755478A (en) 1953-08-14 1953-08-14 Water-soluble organic nitrogen compounds

Country Status (1)

Country Link
GB (1) GB755478A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3234025A (en) * 1959-08-04 1966-02-08 Gevaert Photo Prod Nv Prevention of dye-diffusion in photographic image bearing colloid layers
EP2468927A1 (en) * 2010-12-21 2012-06-27 Basf Se Composition for metal electroplating comprising leveling agent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3234025A (en) * 1959-08-04 1966-02-08 Gevaert Photo Prod Nv Prevention of dye-diffusion in photographic image bearing colloid layers
EP2468927A1 (en) * 2010-12-21 2012-06-27 Basf Se Composition for metal electroplating comprising leveling agent

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