GB747093A - Water-soluble phenol-aldehyde condensation products - Google Patents

Water-soluble phenol-aldehyde condensation products

Info

Publication number
GB747093A
GB747093A GB13844/52A GB1384452A GB747093A GB 747093 A GB747093 A GB 747093A GB 13844/52 A GB13844/52 A GB 13844/52A GB 1384452 A GB1384452 A GB 1384452A GB 747093 A GB747093 A GB 747093A
Authority
GB
United Kingdom
Prior art keywords
resorcinol
water
catechol
soluble
hcl
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
GB13844/52A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB747093A publication Critical patent/GB747093A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C14SKINS; HIDES; PELTS; LEATHER
    • C14CCHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C3/00Tanning; Compositions for tanning
    • C14C3/02Chemical tanning
    • C14C3/08Chemical tanning by organic agents
    • C14C3/18Chemical tanning by organic agents using polycondensation products or precursors thereof

Abstract

A water-soluble condensation product, suitable for use as a tanning agent, is made by condensing (a) 1 mol. of an alpha-beta unsaturated aldehyde, (b) about 2 mols. of resorcinol and (c) at most 1 mol. of a salt of sulphurous acid, or a polyhydric phenol, or a mixture of such a salt and such a phenol, or a salt of an aromatic amine. Up to 1/3 molar proportion of the resorcinol may be replaced by an equimolecular amount of a monohydric phenol and up to 2/3 molar proportion of the resorcinol may be replaced by another polyhydric phenol. The resorcinol, or mixture of resorcinol and another phenol may first be condensed in presence of water or an organic solvent (e.g. alcohols, ethers or esters) to give a water-insoluble product which is then condensed in presence of water with the salt of sulphurous acid, the polyhydric phenol or the salt of an aromatic amine. Alternatively, all of the reactants may be condensed together in presence of water. In examples: (1) A product obtained by condensing resorcinol and acrolein in presence of HCl is made water-soluble by reaction with (a) sodium bisulphite, (b) resorcinol, catechol or pyrogallol and (c) the hydrochlorides of aniline, alpha-naphthylamine, pchloroaniline, as-m-xylidene or cumidene. (2) A product obtained by condensing resorcinol, pyrogallol and acrolein in presence of HCl is made water-soluble by reaction with (a) sodium bisulphite, (b) resorcinol and (c) o-toluidine hydrochloride. (3) A product made by condensing resorcinol with crotonaldehyde in presence of HCl is made water-soluble by reaction with (a) sodium bisulphite, (b) resorcinol, catechol or pyrogallol and (c) the hydrochlorides of aniline, alpha-naphthylamine, dimethyl-aniline or 2-chloro-4-toluidine. (4) A product obtained by condensing resorcinol, acrolein and crotonaldehyde in presence of HCl is made water-soluble by reaction with (a) sodium bisulphite, (b) catechol or (c) o- or p-chloroaniline. (5) A product obtained by condensing resorcinol, "brenzoel" and crotonaldehyde in presence of HCl is made water-soluble by reaction with (a) sodium bisulphite, (b) sodium bisulphite and catechol and (c) aniline hydrochloride. "Brenzoel" is a phenolic oil which is recovered from waste liquors-formed in the low temperature carbonization process of lignites and pit-coals-by extraction with organic solvents. It contains catechol and its homologues (e.g. homo-, isohomo- and ethyl-catechol), resorcinol and its homologues and substituted monohydric phenols. (6) A product obtained by condensing resorcinol, catechol, acrolein and crotonaldehyde in presence of HCl is made water-soluble by reaction with (a) sodium bisulphite, (b) pyrogallol and (c) o- or p-chloroaniline and concentrated HCl. (7) A product obtained by condensing resorcinol, cresol and crotonaldehyde in presence of HCl is made water-soluble by reaction with (a) sodium bisulphite, (b) resorcinol and catechol and (c) aniline-hydrochloride. (8) A product obtained by condensing resorcinol and methyl- or ethyl-acrolein in presence of HCl is made water-soluble by reaction with (a) sodium bisulphite, (b) catechol or (c) aniline hydrochloride. (9) A product obtained by condensing resorcinol and crotonaldehyde in presence of ethyl acetate and HCl is made water-soluble by reaction in presence of water with (a) sodium bisulphite, (b) a polyhydric phenol and (c) a salt of an aromatic amine. (10) A product obtained by condensing resorcinol and cinnamaldehyde in presence of methanol and hydrochloric acid is made water-soluble by reaction in presence of water with (a) sodium bisulphite, (b) resorcinol or catechol and (c) aniline hydrochloride. (11)-(13) Water-soluble products are made by condensing in presence of HCl, (a) resorcinol and acrolein, (b) and (c) resorcinol, catechol and acrolein, (d) resorcinol and crotonaldehyde, (e) and (f) resorcinol, catechol or pyrogallol and crotonaldehyde, (g) resorcinol and crotonaldehyde, (h) and (i) resorcinol, catechol and crotonaldehyde. (14) A product obtained by condensing resorcinol and crotonaldehyde in presence of HCl is made water-soluble by reaction with aniline hydrochloride. (15) A product obtained by condensing resorcinol or resorcinol and catechol with crotonaldehyde in presence of HCl is made water-soluble by reaction with a mixture of sodium bisulphite and sodium sulphite. Specification 747,092 is referred to.
GB13844/52A 1951-05-30 1952-05-30 Water-soluble phenol-aldehyde condensation products Expired GB747093A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE747093X 1951-05-30

Publications (1)

Publication Number Publication Date
GB747093A true GB747093A (en) 1956-03-28

Family

ID=6648552

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13844/52A Expired GB747093A (en) 1951-05-30 1952-05-30 Water-soluble phenol-aldehyde condensation products

Country Status (1)

Country Link
GB (1) GB747093A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7196156B2 (en) 2002-12-13 2007-03-27 Indspec Chemical Corporation Flexibilized resorcinolic novolak resins and method of making same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7196156B2 (en) 2002-12-13 2007-03-27 Indspec Chemical Corporation Flexibilized resorcinolic novolak resins and method of making same
US7589164B2 (en) 2002-12-13 2009-09-15 Durairaj Raj B Flexibilized resorcinolic novolak resins and method of making same

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