Patent GB-1071298-A (GB)
Title: Improvements in or relating to polyfunctional compounds and polymers modified with said compounds
IPC: C07D241/04
Filed: 1964-08-13
Abstract: The invention comprises compounds of the formulae <FORM:1071298/C2/1> where X is CO or SO2; A is divalent acyclic aliphatic of at least 3 carbon atoms; D is alkylene or substituted alkylene of 3 or 4 carbon atoms; R2 is hydrogen, C1- 5 alkyl or hydroxymethyl; R3 is C1- 5 alkyl; Z and Z1 are CH2 = CR-, QCH2CHR- or R1OCH2CHR-, where R and R1 are hydrogen or C1- 5 alkyl and Q is (a) the radical corresponding to a conjugate base of a Lowry-Bronsted acid of dissociation constant in water between 5 x 10-2 and 5 x 10-5, or (b) the residue of a tertiary ammonium cation; and NYN in the last formula above is the residue of a cyclic bis-secondary amine; and in the last formula above, when Z is R1OCH2CHR-, then Z1 is CH2=CHR- or QCH2CHR-.  The radical A includes alkylene, alkenylene, polyoxyethylene, polyoxypropylene and hydroxyalkylene; NYN includes piperazines, pyrazolidines, and 1,4-bis-alkylaminocycloalkanes; Q includes -OSO3M, -SSO3M, -OCOCH3, -OCOH, -OCOC2H5, pyridinium and benzyldimethylammonium (M is NH4 or an alkali metal).  These compounds may be prepared by various acylation processes; or by adding R1OH or a suitable Q-containing compound to a compound having Z or Z1 as CH2 = CR-; R2 as alkyl may be introduced by alkylation, or as -CH2OH by reaction with formaldehyde; D may be introduced by reacting a compound having R2 as hydrogen with an organic dehalide of 3 or 4 carbon atoms; compounds with X as SO2 and Q as -OSO2NH4 are obtained from carbyl sulphate and an amine in the presence of ammonia or a derivative thereof.  The compounds of the invention are cross-linking agents for active-hydrogen-containing polymers such as cellulosic materials (see Division C3), and are said to be therapeutic agents.ALSO:Active hydrogen-containing polymers, such as cellulosic textile materials, polyvinyl alcohol and starch, are cross-linked by contacting them under alkaline conditions, with a compound of formula <FORM:1071298/C3/1> or <FORM:1071298/C3/2> where X is CO or SO2; A is divalent acyclic aliphatic of at least 3 carbon atoms; D is alkylene or substituted alkylene of 3 or 4 carbon atoms; R2 is hydrogen, C1- 5 alkyl or hydroxymethyl; R3 is C1- 5 alkyl; Z and Z1 are CH2=CR-, QCH2CHR- or R1OCH2CHR-, where R and R1 are hydrogen or C1- 5 alkyl and Q is (a) the radical corresponding to a conjugate base of a Lowry-Boronsted acid of dissociation constant in water between 5 x 10-2 and 5 x 10-5 (e.g. -OSO3M, -SSO3M, -OCOCH3, -OCOH and -OCOC2H5, M being NH4 or an alkali metal), or (b) the residue of a tertiary ammonium cation; and NYN is the residue of a cyclic bis-secondary amine (with the N atoms part of a heterocyclic ring, or attached to a cycloalkane ring); and in the last formula above, when Z is R1OCH2CHR-, then Z1 is CH2= CHR- or QCH2CHR- (see Division C2).  The cellulosic material may be in the form of fibres, mats, non-woven assemblies, yarns or knitted or woven fabrics.  Blends of cotton with other natural or synthetic fibres may be treated. Softeners, hand builders, pigments, dyestuffs and stain repellers may be present during the  treatment, as well as chemically inert materials such as polyethylene or acrylic resins.  Dyes or sizing materials containing reactive groups may be linked to the cellulosic material by the compounds of the invention.ALSO:Cellulosic textile materials, are cross-linked by contacting them under alkaline conditions, with a compound of formula: <FORM:1071298/D1-D2/1> where X is CO or SO2; A is divalent acyclic aliphatic of at least 3 carbon atoms; D is alkylene or substituted alkylene of 3 or 4 carbon atoms; R2 is hydrogen, C1-5 alkyl or hydroxymethyl; R3 is C1-5 alkyl; Z and Z1 are CH2 =CH-, Q CH2 CHR- or R1 OCH2 where R and R1 are hydrogen or C1-5 alkyl and Q is (a) the radical corresponding to a conjugate base of a Lowry-Bronsted acid of dissociation constant in water between 5x10-2 and 5x10-5 (e.g. -OSO3M, -SSO3M, -OCOCH3, -OCOH and -OCOC2H5, M, be ing NH4 or an alkali metal), or (b) the residue of a tertiary ammonium cation; and NYN is the residue of a cyclic bis-secondary amine (with the N atoms part of a heterocyclic ring, or attached to a cyclo alkane ring); and in the last formula above, when Z is R1OCH2CHR-, then Z1 is CH2 = CHR or Q CH2 CHR- (see Division C2). The cellulosic material may be in the form of fibres, mats, non-woven assemblies, yarns or knitted or woven fabrics.  Blends of cotton with other natural or synthetic fibres may be treated. Softeners, hand builders pigments, dyestuffs and stain repellers may be present during the treatment, as well as chemically inert materials such as polyethylene or acrylic resins.  Dyes or sizing materials containing reactive groups may be linked to the cellulosic material by the compounds of the invention.