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GB359773A - A method of treating rubber - Google Patents

A method of treating rubber

Info

Publication number
GB359773A
GB359773A GB36032/30A GB3603230A GB359773A GB 359773 A GB359773 A GB 359773A GB 36032/30 A GB36032/30 A GB 36032/30A GB 3603230 A GB3603230 A GB 3603230A GB 359773 A GB359773 A GB 359773A
Authority
GB
United Kingdom
Prior art keywords
acetone
aniline
derivatives
diphenylamine
ketone
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
GB36032/30A
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.)
Uniroyal Chemical Co Inc
Original Assignee
Naugatuck Chemical 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 Naugatuck Chemical Co filed Critical Naugatuck Chemical Co
Publication of GB359773A publication Critical patent/GB359773A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/17Amines; Quaternary ammonium compounds
    • C08K5/18Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/29Compounds containing one or more carbon-to-nitrogen double bonds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Ketone-amine condensation products and derivatives thereof.-The reaction product of a ketone and an aromatic amino compound, or derivatives of such reaction products, are used to retard the deterioration of rubber. The reaction product may be made with or without the aid of a dehydrating agent of which the following are specified: calcium chloride, iodine, sulphanilic acid, phosphorus pentoxide, sodium hydroxide, magnesium perchlorate, acetic acid, barium oxide, zinc chloride, sulphuric acid, or the zinc chloride double salt of the amine. It is stated that different compounds may be obtained by the reaction in relative amounts which may vary with the duration of heating and the dehydrating agent employed. Thus sulphanilic acid tends to give more highly condensed products than iodine or calcium chloride. The derivatives include aldehyde derivatives, sulphur derivatives such as are formed by the action of sulphur, carbon disulphide, sodium polysulphides or sulphur chlorides on the reaction product, nitroso derivatives, formic acid derivatives, and naphthol addition products. The preparation of the following products is either described in examples or otherwise referred to: (1) Ketone-amines: acetone-aniline, acetone-phenylhydrazine, acetone-p,p1-diaminodiphenylmethane, acetone-diphenylamine, acetone-diphenyl formamidine, mesityl oxide-aniline, diacetone alcohol-aniline, acetone-phenyla -, or b - naphthylamine, acetone - a - naphthylamine, acetophenone-aniline, cyclohexanone-aniline, formaldehyde acetone condensation product-aniline, mesityl oxide-phenyl-, a - or b -naphthylamine, acetone-triphenylmelamine, acetone - di - o - tolylguanidine, acetone-diphenylguanidine, acetone-p,p1-dinaphthylaminodiphenylmethane, acetone-monoethylaniline, tetramethyldiamidobenzophenone-aniline, acetone-o-tolylbiguanide, acetone-diphenyldiaminoethane, methylethyl-ketone-p,p1-diaminodiphenylmethane, ethylideneacetone-p,p1-diaminodiphenylmethane, acetone-mixture of b -naphthol and aniline, acetone-mixture of phenol and aniline, monochloroacetone-aniline, acetonetoluidines, acetaldolacetone-diphenylamine, acetonediphenylethylenediamine, methylethylketone-diphenylamine, methylethylketone-phenyl - a - naphthylamine, acetone-o-tolylguanidine. Instead of these ketones there may be used-phorone, diethylketone, benzophenone, dichloracetone, aldol acetone, allylacetone, benzalacetone, diacetyl, acetylacetone, acetonylacetone, salicaldehyde acetone, furfuralacetone. The term ketone also includes thioketones and ketone dihalides and is further defined as meaning compounds containing one or more keto groups but containing no carboxylic acid or ester groups. Instead of the amines mentioned there may be used monochloranilines, o-, m-, or p-toluidine, xylidines, b -naphthylamine, aminodiphenyls, dinaphthylamines, asymm - diphenylhydrazine, diaminodiphenyl sulphide, diaminodiphenyl polysulphides, diaminodinaphthyl sulphides, p-aminobenzylaniline, dinaphthyldiaminoethane, ditolyldiaminoethane, p-amino-p1-naphthylaminodiphenylmethane, p.p1-diaminodiphenyldimethylmethane, p.p1-dinaphthylaminodiphenyldimethylmethane, phenyl-b -naphthylguanidine, phenyl-o-tolylguanidine, di-o-tolylbiguanide, monophenylbiguanide, diphenylbiguanide, and diphenylacetamidine. (2) Aldehyde derivatives: formaldehyde, acetaldehyde aldol, butyraldehyde, crotonaldehyde, or heptaldehyde-acetone-aniline, formaldehyde-chloracetone-aniline, formaldehyde-acetone-diphenylamine, butyraldehyde-acetone-diphenylamine. (3) Sulphur derivatives: sulphur derivative of acetone-diphenylamine. (4) Nitroso derivatives: nitroso derivative of acetone-diphenylamine. (5) Formic acid derivatives: formic acid derivative of acetone-diphenylamine. (6) Naphthol addition products: the b -naphthol addition product of acetone-aniline, acetone p.p1-diaminodiphenylmethane, chloracetone-aniline, and acetone-diphenylamine. Instead of b -naphthol there may be used a -naphthol, methylene-di-b -naphthol, dihydroxynaphthalenes such as 1.5 dihydroxynaphthalene. p.p1-Di-(naphthylamino)-diphenylmethane is prepared by heating a mixture of p.p-diaminodiphenylmethane (1 mol.) and b -naphthol (2 mols.) in presence of calcium chloride or iodine. p.p1-Di-(naphthylamino)-diphenyldimethylmethane is prepared similarly to the foregoing compound.ALSO:Rubber is treated to retard deterioration, with the reaction product of a ketone and an aromatic amino compound, or with a derivative of such a reaction product. Thus aldehyde derivatives, sulphur derivatives such as of acetone diphenylamine, formed by the action of sulphur, carbon disulphide, sodium polysulphides or sulphur chlorides on the reaction product, nitroso derivatives as of acetonediphenylamine, formic acid derivatives as of acetonediphenylamine, or naphthol addition products may be used. Thioketones or the corresponding ketone dihalide may be used instead of the ketone to form the initial reaction product. The reaction product may be formed with or without the aid of a dehydrating agent such as calcium chloride, iodine, sulphanilic acid, phosphorus pentoxide, sodium hydroxide, magnesium perchlorate, acetic acid, barium oxide, zinc chloride, sulphuric acid, &c. Alternatively the zinc chloride double salt of the amine may be used. Numerous examples of the preparation of these reaction products are given.
GB36032/30A 1929-12-04 1930-11-29 A method of treating rubber Expired GB359773A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US359773XA 1929-12-04 1929-12-04

Publications (1)

Publication Number Publication Date
GB359773A true GB359773A (en) 1931-10-29

Family

ID=21885882

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36032/30A Expired GB359773A (en) 1929-12-04 1930-11-29 A method of treating rubber

Country Status (1)

Country Link
GB (1) GB359773A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2511064A (en) * 1946-06-12 1950-06-13 Monsanto Chemicals Preservation of rubbery polymers by derivatives of ketone amines
US2511063A (en) * 1946-06-12 1950-06-13 Monsanto Chemicals Condensation product of formaldehyde, a phenol, and a ketone-amine condensate
US2562802A (en) * 1947-06-18 1951-07-31 Us Rubber Co Manufacture of ketone diarylamine condensation products

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2511064A (en) * 1946-06-12 1950-06-13 Monsanto Chemicals Preservation of rubbery polymers by derivatives of ketone amines
US2511063A (en) * 1946-06-12 1950-06-13 Monsanto Chemicals Condensation product of formaldehyde, a phenol, and a ketone-amine condensate
US2562802A (en) * 1947-06-18 1951-07-31 Us Rubber Co Manufacture of ketone diarylamine condensation products

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