GB468399A - Improvements in water-soluble phenolic derivatives - Google Patents

Improvements in water-soluble phenolic derivatives

Info

Publication number
GB468399A
GB468399A GB3451/36A GB345136A GB468399A GB 468399 A GB468399 A GB 468399A GB 3451/36 A GB3451/36 A GB 3451/36A GB 345136 A GB345136 A GB 345136A GB 468399 A GB468399 A GB 468399A
Authority
GB
United Kingdom
Prior art keywords
formaldehyde
alcohols
phenol
phenolic
dimethylamine
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
GB3451/36A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB468399A publication Critical patent/GB468399A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G14/00Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
    • C08G14/02Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
    • C08G14/04Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
    • C08G14/06Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Lubricants (AREA)
  • Cosmetics (AREA)

Abstract

Phenolic products primarily adapted for use as soaps, wetting, emulsifying, tanning and germicidal agents are obtained by heating an alcohol containing a primary alcoholic group and a hydrohalide or sulphuric acid salt of a phenolic amine obtained by condensing a phenol, formaldehyde and a secondary amine of the formula XNHX1, in which X and X1 are alkyl groups which may link up to form a polymethylene ring. Not more than one molecule each of the phenol and formaldehyde is used for each molecule of secondary amine and the term phenol covers mono and polycyclic phenols and Novolak resins which are soluble in dilute caustic soda. The manufacture of the said salts is described in Specifications 444,351 and 457,391. In examples: (1) a condensate obtained from phenol, dimethylamine and formaldehyde is converted into its sulphuric acid salt in the presence of toluene and reacted with lauryl, cetyl and oleyl alcohols, a - ethylhexanol, 1 : 10 - decamethyleneglycol, octadecanediol, and a : a : g : g -tetramethylbutylphenoxyethanol; (2) a condensate obtained from o-cresol, dimethylamine and formaldehyde is converted into its sulphuric acid salt and reacted with lauryl and cetyl alcohols; (3) a condensate obtained from a : a : g : g -tetramethylbutylphenol, dimethylaniline and formaldehyde is converted into its hydrochloride or sulphate and reacted with ethyl and lauryl alcohols, glycerol, and diethyleneglycol; (4) laurylalcohol is reacted with the sulphates of the phenolic amines obtained by condensing formaldehyde and dimethylamine with 1 : 3 : 5-xylenol, p-chlorphenol, o-phenylphenol, or b -naphthol or by condensing formaldehyde and piperidine with a : a : g : g -tetramethylbutylphenol or by condensing formaldehyde and diethylamine with bis-(p-hydroxydiphenyl)-dimethylmethane. The products may be used in washing, bleaching, bucking, tanning, mordanting and dyeing processes, in hydrolyzing fats, emulsifying oils and fats in water, breaking petroleum emulsions and dispersing pigments and dyestuffs. They may also be added to pine oil and soapy germicides. The products may be coupled with diazotized aromatic amines to give azo dyestuffs, and the product obtained by reacting laurylalcohol with the condensate from p-chlorphenol, formaldehyde and dimethylamine is stated to be a soft resin. Trimethyleneglycol, triethyleneglycol, glycolmonoethyl or butyl ether, pentaerithrite, mannitol, phenoxyethanol, tetrahydrofurfurylalcohol, the alcohols obtained by reducing coconut oil, palm oil, tallow and castor oil, alcohols obtained from spermaceti, beeswax and wool grease and alcohols containing sulphur, oxygen, and the group CO-- in the molecule are mentioned as suitable alcohols, while the following phenolic compounds are specified: propylto octyl-phenols, decylphenol, laurylphenol, cetylphenol and the corresponding cresols and resorcinols, benzylphenol, cyclohexylphenol, thymol, guaiacol, pyrocatechol, hydroquinone and their halogen, alkoxy and acyl derivatives.ALSO:Phenolic products useful for splitting fats and for emulsifying oils and fats in water are obtained by heating an alcohol containing a primary alcoholic group and a hydrohalide or sulphuric acid salt of a phenolic amine obtained by condensing a phenol, formaldehyde and a secondary amine of the formula XNHX, in which X and X1 are alkyl groups which may link up to form a polymethylene ring. The term phenol covers mono- and poly-cyclic phenols and Novolak resins which are soluble in dilute caustic soda. In examples: (1) a condensate obtained from phenol, dimethylamine and formaldehyde is converted into its sulphuric acid salt and reacted with lauryl, cetyl and oleyl alcohols, a -ethylhexanol, 1 : 10-decamethyleneglycol, 1 : 12-octadecanediol, and a .a : g : g - tetramethylbutylphenoxyethanol; (2) a condensate obtained from o-cresol, dimethylamine and formaldehyde is converted into its sulphuric acid salt and reacted with lauryl and cetyl alcohols; (3) a condensate obtained from a : a : g : g -tetramethyl butylphenol, dimethylaniline and formaldehyde is converted into its hydrochloride or sulphate and reacted with ethyl and lauryl alcohols, glycerol and diethyleneglycol; (4) lauryl alcohol is reacted with the sulphates of the phenolic amines obtained by condensing formaldehyde and dimethylamine with 1 : 3 : 5-xylenol, p-chlorphenol, o-phenyl-phenol or b -naphthol, or by condensing formaldehyde and piperidine with a : a : g - g -tetramethylbutylphenol, or by condensing formaldehyde and diethylamine with bis-(p-hydroxydiphenyl)-dimethylmethane. Trimethyleneglycol, triethyleneglycol, glycolmonoethyl or butyl ether, pentaerythrite, mannitol, phenoxyethanol, tetrahydrofurfurylalcohol, the alcohols obtained by reducing coconut oil, palm oil, tallow and castor oil, alcohols obtained from spermaceti, beeswax and wool grease and alcohols containing sulphur, oxygen and the group CO-in the molecule are mentioned as suitable alcohols, while the following phenolic compounds are specified: propylto octyl-phenols, decylphenol, laurylphenol, cetylphenol and the corresponding cresols and resorcinols, benzylphenol, cyclohexylphenol, thymol, guaiacol, pyrocatechol, hydroquinone and their halogen, alkoxy and acyl derivatives.ALSO:Phenolic products obtained by heating an alcohol containing a primary alcoholic group and a hydrohalide or sulphuric acid salt of a phenolic amine derived from a phenol, formaldehyde and a secondary amine of the formula XNHX1, in which X and X1 are alkyl groups which may link up to form a polymethylene ring, are added to pine oil or soap to increase their germicidal power. Alcohols specified are lauryl, oleyl and cetyl alcohol, 1 : 10-decamethyleneglycol, 1 : 12-octadecanediol, a : a : g : g -tetramethylbutylphenoxyethanol, glycerol, diethyleneglycol, p trimethyleneglycol, pentaerithrite, mannitol, phenoxyethanol, and tetrahydrofurfurylalcohol. The phenolic amines may be derived from phenol, cresol, xylenol, a : a : g : g -tetramethylbutylphenol, p-chlorphenol, b -naphthol, bis-(p-hydroxydiphenyl) - dimethylmethane, propylphenol, laurylphenol, resorcinol, cyclohexylphenol, thymol, guaiacol, pyrocatechol, hydroquinone and their halogen, alkoxy and acylderivatives. Dimethylamine, dimethylaniline and piperidine are mentioned as suitable secondary amines.
GB3451/36A 1935-02-13 1936-02-05 Improvements in water-soluble phenolic derivatives Expired GB468399A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US468399XA 1935-02-13 1935-02-13

Publications (1)

Publication Number Publication Date
GB468399A true GB468399A (en) 1937-07-05

Family

ID=21945674

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3451/36A Expired GB468399A (en) 1935-02-13 1936-02-05 Improvements in water-soluble phenolic derivatives

Country Status (2)

Country Link
DE (1) DE663998C (en)
GB (1) GB468399A (en)

Also Published As

Publication number Publication date
DE663998C (en) 1938-08-20

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