GB375843A - Process for manufacturing condensation products - Google Patents

Process for manufacturing condensation products

Info

Publication number
GB375843A
GB375843A GB9414/31A GB941431A GB375843A GB 375843 A GB375843 A GB 375843A GB 9414/31 A GB9414/31 A GB 9414/31A GB 941431 A GB941431 A GB 941431A GB 375843 A GB375843 A GB 375843A
Authority
GB
United Kingdom
Prior art keywords
formaldehyde
disulphamide
benzene
condensed
added
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
GB9414/31A
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.)
KARL RUTTER
Original Assignee
KARL RUTTER
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 KARL RUTTER filed Critical KARL RUTTER
Publication of GB375843A publication Critical patent/GB375843A/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
    • C08G12/00Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/04Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08G12/24Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with sulfonic acid amides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

Aldehydes such as formaldehyde, which may be used as a gas, solution, polymer or as a substance that will yield formaldehyde such as hexamethylenetetramine, or other aldehydes such as furfurol, are condensed or polymerized with aromatic sulphonamides containing, besides the sulphamido group at least one substituted or unsubstituted amino group, other than a carbamido group, or groups or mixtures of such groups. Such compounds may be aniline or phenylenediamine into which a sulphamido group has been introduced, di, tri- or polysulphamides and they may be polynuclear such as naphthalene derivatives and other compounds which contain besides one sulphamido group at least a further amino group such as multisulphamitated sulphones and multisulphamidated benzophenones. The bodies may be condensed in the presence of the catalysts employed in the manufacture of phenolor urea-formaldehyde resinous products, strong acids or strong bases being preferred, and in the absence or presence of solvents such as aqueous or organic liquids. Initial compounds such as methylol or methylene derivatives in crystalline or amorphous form may be first made and the products may be converted into resins by heating in solution or in the absence of solvents such as by fusing. The first stage may be conducted in a neutral or alkaline medium such as in caustic potash or hexamethylenetetramino to first form the methylol compounds and the second stage may be conducted in acid medium using acids, salts or esters or prolonged heating or oxidizing agents may be used. The acid may be removed by neutralization. The intermediate products are soluble in organic solvents to water-clear lacquers giving glass-like final products which may be worked up with or without fillers. Before, during or after the condensation, formaldehyde-binding substances such as phenols, urea, thiourea, amines or sulphamides containing carbamido groups may be added to the reaction mixture and mono-amides, such as p-toluene sulphamide, which, with formaldehyde, do not form resins capable of being hardened, may also be added. Other natural or artificial resins, cellulose esters or ethers or other plastic masses may be added giving products which can be worked up into lacquers with oils or cellulose derivatives. The condensation products can be moulded, if desired in powder form, with or without the addition of fillers, in the usual manner with heat and pressure. In examples: (1) Benzene m-disulphamide is boiled with a solution of formaldehyde to give a condensation product which separates on cooling yielding a clear lacquer when dissolved in alcohol; the resin, before hardening, may be freed from water by heating in vacuo; tougher products are obtained by continuing the condensation. (2) Benzene-m-disulphamide and aqueous formaldehyde are condensed in the presence of hydrochloric acid. (3) Caustic potash is used in the condensation in example 1; caustic potash, if added to the lacquer or compressed mixture, acts as a hardening accelerator; pyridine may also be used. (4) Benzene-m-disulphamide and phenol are mixed with formaldehyde in the presence of caustic soda and after cooling phosphoric acid is added to separate the product into layers the lower of which is worked up to a lacquer or an artificial mass. (5) Benzene-m-disulphamide and paraformaldehyde are added to alcoholic potash and acetone is added to the heated and acidulated solution to give a lacquer. (6) Xylene-disulphamide is condensed with formaldehyde. (7) Formaldehyde and benzene-m-disulphamide are added to alcoholic potash and a water soluble resin gradually separates in the cold. (8) 1-Chlor-2 : 4-disulphamido-benzene or dichlorobenzen-p-disulphamide may replace benzene-m-disulphamide in the previous examples. (9) 1-Methyl-2 : 4-disulphamido-benzene is condensed with formaldehyde. (10) 1-Amino-2 : 4 : 6-trisulphamido-benzene, aniline-p-sulphamide or acetyl compounds are condensed with formaldehyde. (11) Dimethyleneaniline trisulphamide may be formed in the cold from 1-amino-2 : 4 : 6-trisulphamidobenzene and formaldehyde and 1-methyl-4-amino-2 : 5-disulphamidobenzene and formaldehyde give a crystalline body; the intermediate bodies, by further heating with formaldehyde give resins. (12) Benzene-m-disulphamide is condensed with formaldehyde and shortly before completion of the reaction a further quantity of benzene-m-disulphamide is added. (13) Benzene-m-disulphamide is dissolved in formaldehyde and caustic potash and hydrochloric acid added to precipitate the resin as a white amorphous powder which yields a spirit varnish or may be moulded with heat alone or with fillers such as cellulose. (14) 1-Oxy-2 : 4-disulphamidobenzene is condensed with formaldehyde. (15) The lacquer prepared by dissolving an intermediate condensation product of benzene-m-disulphamide and formaldehyde is absorbed by cellulose and after hardening the product is pulverized and compressed; fillers such as paper or colouring materials may be introduced at the beginning of the condensation process. (16) A mixture of benzene-m-disulphamide and toluene-p-monosulphamide is condensed with formaldehyde. (17) Benzene-m-disulphamide is condensed with formaldehyde with the addition of thiourea at intervals. (18) Benzene-m-disulphamide is condensed with furfurol. (19) Benzene-m-disulphamide is condensed with benzaldehyde. Specification 359,522 is referred to. Xylene disulphamide is prepared from technical arylene. Dichlorbenzene-p-disulphamide is prepared by heating p-dichlorbenzene with chlorsulphonic acid to form dichlorbenzene-p-disulphochloride and then treating this with ammonia.ALSO:Condensation products of aldehydes with aromatic sulphamides containing besides the sulphamide group at least one substituted or unsubstituted amino group, other than a carbamido group, may be worked up with fillers such as other natural or synthetic resins, cellulose esters or ethers or other plastic masses. In an example a lacquer prepared by dissolving the intermediate condensation product of benzene-m-disulphamide and formaldehyde in acetone is absorbed by cellulose and the hardened product is pulverized and compressed to give a hard transparent product of horn-like appearance or a white compressed product of porcelain-like nature.
GB9414/31A 1930-03-27 1931-03-27 Process for manufacturing condensation products Expired GB375843A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AT375843X 1930-03-27

Publications (1)

Publication Number Publication Date
GB375843A true GB375843A (en) 1932-06-27

Family

ID=3673043

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9414/31A Expired GB375843A (en) 1930-03-27 1931-03-27 Process for manufacturing condensation products

Country Status (1)

Country Link
GB (1) GB375843A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2609356A (en) * 1949-02-17 1952-09-02 Bofors Ab Manufacture of bright, stable, and lightproof sulfonamide resins
CN110860194A (en) * 2018-08-27 2020-03-06 湖北泰盛化工有限公司 Device and method for treating paraformaldehyde dust in glyphosate production feeding process

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2609356A (en) * 1949-02-17 1952-09-02 Bofors Ab Manufacture of bright, stable, and lightproof sulfonamide resins
CN110860194A (en) * 2018-08-27 2020-03-06 湖北泰盛化工有限公司 Device and method for treating paraformaldehyde dust in glyphosate production feeding process
CN110860194B (en) * 2018-08-27 2021-09-07 湖北泰盛化工有限公司 Device and method for treating paraformaldehyde dust in glyphosate production feeding process

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