Patent GB-846098-A (GB)
Title: Improvements in dimensional stabilization of cellulose
IPC: D06M13/184
Filed: 1956-10-18
Abstract: Cellulose material is impregnated with an aqueous solution of the salt of an organic acid which contains in addition to the carboxyl group at least one more carboxyl group and/or at least one hydroxyl group, with a basic organic nitrogen compound which has at least one hydroxyl group attached to a carbon atom in the molecule, the treated material retaining, when dried, from 5 to 50 %, by weight, of the salt.  The material treated may be regenerated cellulose sheets.  The acid compound may be a polycarboxylic acid, a hydroxy acid, an acid ester or mixed ester of a polyhydric alcohol, a reaction product or adduct of an unsaturated polycarboxylic acid and a conjugated diene which may itself be a carboxylic acid.  Among the acid compounds specified are the reaction product of eleostearic acid and maleic anhydride; the adduct formed by reacting abietic acid with maleic anhydride; gallic acid; succinic acid; adipic acid; azelaic acid; malic acid; sebacic acid; citric acid; salicylic acid; propylene glycol dicitrate; acid esters formed from ethylene glycol and polyethylene glycol with adipic acid or sebacic acid or of propylene glycol and the adduct formed from abietic acid and maleic anhydride; a mixed acid ester formed from polyethylene glycol and maleic anhydride and adipic acid; an ester from dipropylene glycol and an adduct of abietic acid and maleic anhydride; phthalic anhydride and succinic anhydride.  The base may be a compound of the formula RR2(N)R1OH in which R and R2 are hydrogen, alkyl, acyl, aryl, alkaryl, hydroxyalkyl or hydroxyalkaryl and R1 is alkyl, or may be a heterocyclic compound, alkanol substituted ammonium hydroxide, an amino glycol or an amino phenol.  Amongst the bases specified are mono, di- and tri-ethanolamine; dimethyl ethanolamine; phenyl methyl ethanolamine; phenyl ethyl ethanolamine, dimethyl isopropanolamine; N-acetyl ethanolamine; diethyl ethanolamine; phenylethanolamine; N, N,dibutyl isopropanolamine; methyl benzyl monoethanolamine; N,hydroxyethyl morpholine; the compound of the formula <FORM:0846098/IV(a)/1> 8-quinolinol; N,N,N1N1-tetrakis-(2-hydroxypropyl) ethylene diamine; tetraethanol ammonium hydroxide; 2-amino -2(hydroxymethyl)-1, 3-propanediol; p-amino-phenyl ethyl alcohol and p-amino-phenol.  The compounds may be applied, at temperatures up to 100 DEG C, and pH3-9, in aqueous or aqueous-organic solution. Methyl, ethyl and propyl alcohols; dimethyl, diethyl, methyl ethyl, methyl propyl and ethyl propyl ketones are specified organic solvents.  The treating compositions may also include animal glue or gelatine and a paraffin wax or a synthetic wax; natural rubber emulsions or latexes; styrene-butadiene latexes or phenolformaldehyde, urea-formaldehyde or melamineformaldehyde precondensates.  The treated material may be dried and heated at temperatures up to 150 DEG C.  It is stated that amides or imides may be formed upon heating.  Example 32 relates to treating regenerated cellulose film.  Specifications 388,769, 430,221, 433,110, 602,048, 652,845, 662,542, 698,135 and U.S.A. Specifications 2,629,648, 2,629,701 and 2,692,183 are referred to.ALSO:Salts are formed of organic nitrogen bases which have at least two carbon atoms in the molecules and at least one hydroxyl group attached to a carbon atom, and partial esters of polycarboxylic acids and aliphatic polyhydric alcohols or the reaction product of an excess of a polycarboxylic acid with a polyhydric alcohol in which all the hydroxy groups are esterified but free carboxyl groups remain, or of adducts of polycarboxylic acids and unsaturated conjugated dienes which may themselves be carboxylic acids, e.g. the adducts of eleostearic acid or abietic acid and maleic anhydride. Bases specified are compounds of the formula RR2(N)R1OH in which R and R2 are hydrogen, alkyl, acyl, aryl, alkaryl, hydroxyalkyl, or hydroxyalkaryl and R1 is alkyl ; alkanol substituted ammonium hydroxide, amino glycols or aminophenols, mono-di- and triethanolamine, phenyl ethyl ethanolamine, dimethyl isopropanolamine, N-acetyl ethanolamine, diethyl ethanolamine, phenylethanolamine, N,N-dibutyl isopropanolamine, methyl benzyl monoethanolamine, N-hydroxyethyl morpholine, the compound: <FORM:0846098/IV(b)/1> 8-quinolol, N,N,N1,N1-tetrakis-(2-hydroxypropyl) ethylene diamine, tetraethanol ammonium hydroxide, 2-amino-2(hydroxymethyl)-1,3-propane diol, p-amino phenyl ethyl alcohol and p-amino-phenol.  Starting materials for the acid esters include citric, adipic, azelaic, maleic, sebacic, and phthalic acids and ethylene glycol, diethylene glycol, higher poly-ethylene glycols, dipropylene glycol, 1,4-butane diol, 1,2,4-butane triol, 2-ethyl-hexanediol and glycerol.  In example 18, abietic acid and maleic anhydride are heated at 150 DEG C. to form an adduct and the adduct is reacted in water with monoethanolamine.  In example 46 a mixed partial ester, formed by heating together polyethylene glycol, adipic acid and maleic anhydride, is reacted in water with monoethanolamine.  U.S.A. Specifications 2,629,648, 2,629,701 and 2,692,183 are referred to.ALSO:Cellulose material is impregnated with an aqueous solution of the salt of an organic acid which contains in addition to the carboxyl group at least one more carboxyl group and/or at least one hydroxyl group, with a basic organic nitrogen compound which has at least one hydroxyl group attached to a carbon atom in the molecule, the treated material retaining, when dried, from 5% to 50%, by weight, of the salt.  The material treated may be woven cloth of natural or regenerated cellulose fibres.  The acid compound may be a polycarboxylic acid, a hydroxy acid, an acid ester or mixed ester of a polyhydric alcohol, a reaction product or adduct of an unsaturated polycarboxylic acid and a conjugated diene which may itself be a carboxylic acid.  Among the acid compounds specified are the reaction product of eleostearic acid and maleic anhydride; the adduct formed by reacting abietic acid with maleic anhydride; gallic acid; succinic acid; adipic acid; azelaic acid; malic acid; sebacic acid; citric acid; salicylic acid; propylene glycol dicitrate; acid esters formed from ethylene glycol and polyethylene glycol with adipic acid or sebacic acid or of propylene glycol and the adduct formed from abietic acid and maleic anhydride; a mixed acid ester formed from polyethylene glycol and maleic anhydride and adipic acid; an ester from di-propylene glycol and an adduct of abietic acid and maleic anhydride; phthalic anhydride and succinic anhydride.  The base may be a compound of the formula RR2(N)R1OH in which R and R2 are hydrogen, alkyl, acyl, aryl, alkaryl, hydroxyalkyl or hydroxyalkaryl and R1 is alkyl, or may be a heterocyclic compound, alkanol substituted ammonium hydroxide, an amino glycol or an amino phenol.  Amongst the bases specified are mono, di- and tri-ethanolamine; dimethyl ethanolamine; phenyl methyl ethanolamine; phenyl ethyl ethanolamine, dimethyl isopropanolamine; N-acetyl ethanolamine; diethyl ethanolamine; phenylethanolamine; N, N, dibutylisopropanolamine; methyl benzyl monoethanolamine; N, hydroxyethylmorpholine; the compound of the formula: <FORM:0846098/IV (c)/1> 8-quinolinol; N, N, N1 N1-tetrakis-(2-hydroxypropyl) ethylene diamine; tetraethanol ammonium hydroxide; 2-amino-2(hydroxymethyl)-1, 3-propanediol; p-amino-phenyl ethyl alcohol and p-amino-phenol.  The compounds may be applied, at temperatures up to 100 DEG C., and pH3-9, in aqueous or aqueous-organic solution.  Methyl, ethyl and propyl alcohols; dimethyl, diethyl, methyl ethyl, methyl propyl and ethyl propyl ketones are specified organic solvents.  The treating compositions may also include animal glue or gelatin and a paraffin wax or a synthetic wax; natural rubber emulsions or latices; styrene-butadiene latices or phenol-formaldehyde, urea-formaldehyde or melamine-formaldehyde precondensates.  The treated material may be dried and heated at temperatures up to 150 DEG C.  It is stated that amides or imides may be formed upon heating.  Examples 30 and 79 relate to treating textiles. Specifications 388,769, 430,221, 433,110, 602,048, 652,845, 662,542, 698,135 and U.S.A. Specifications 2,629,648, 2,629,701 and 2,692,183 are referred to.