GB249113A - Improvements in the vulcanisation of rubber substances - Google Patents

Improvements in the vulcanisation of rubber substances

Info

Publication number
GB249113A
GB249113A GB6451/22A GB645126A GB249113A GB 249113 A GB249113 A GB 249113A GB 6451/22 A GB6451/22 A GB 6451/22A GB 645126 A GB645126 A GB 645126A GB 249113 A GB249113 A GB 249113A
Authority
GB
United Kingdom
Prior art keywords
butyraldehyde
aldehyde
acid
aniline
heptaldehyde
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
GB6451/22A
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.)
Grasselli Chemical Co
Original Assignee
Grasselli 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 Grasselli Chemical Co filed Critical Grasselli Chemical Co
Publication of GB249113A publication Critical patent/GB249113A/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
    • C08K5/29Compounds containing one or more carbon-to-nitrogen double bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L7/00Compositions of natural rubber
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/22Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds

Landscapes

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

Abstract

249,113. Grasselli Chemical Co., (Assignees of Williams, I., and Burnett, W. B.). March 13, 1925, [Convention date]. Drawings to Specification. Aldehyde-amine condensation products.- Rubber substances are vulcanized with the aid of the products obtained by condensing two or more (up to twenty) molecular proportions of an alpha-#-saturated aldehyde (i.e. an aldehyde in which the a and # atoms are linked by a single bond) with one molecular proportion of a primary amine. Suitable amines are aniline, n-butylamine, ethylamine, and o-tolydiguanide, and propionaldehyde, n-butyraldehyde and heptaldehyde are examples of suitable aldehydes. The properties of the rubber obtained by vulcanizing at 140‹ C. with accelerators prepared from different proportions of aldehyde and amine are tabulated for the following condensation products :-heptaldehyde with n-butylamine; and n-butyraldehyde with aniline, o-tolyldiguanide, and n-butylamine. Curves illustrating some of the data are also given, and it is shown that the accelerating function of the products increases with increasing proportions of aldehyde to maxima which are usually between 3 and 7 molecules of aldehyde to one of amine. The Specification as open to inspection under Sect. 91 (3) (a) describes also the manufacture of condensation products which may be used as accelerators in the vulcanization of india-rubber by causing one molecular proportion of any amino-body to react with two or more (up to twenty) molecular proportions of any aldehyde under conditions wherebv water is eliminated. Suitable amines and aldehydes, in addition to those mentioned above, are ethylamine, ethylene diamine, o-toluidine, methylamine, and diethylamine, and acetaldehyde, crotonaldehyde, citral, acetaldol, and cinnamic aldehyde. Polymerized aldehydes, e.g. para- and meta-aldehydes may also be used. The condensation may be carried out in the presence or absence of acids or acidic substances, e.g. acetic, propionic, n-butyric, stearic, oleic, salicylic, picric, hydrochloric, phosphoric or sulphuric acids, zinc chloride, or acid anhydrides or acid halides. The amount of acid used is preferably between 0.05 and 0.3 molecular proportions for each molecular proportion of amine used, and the acid may be provided by using a portion of the amine in the form of a salt. Inert solvents may also be present. The products obtained by condensing primary amines in the presence of organic acids with alpha-#-saturated aliphatic aldehydes give the best results as vulcanization accelerators. The condensation of heptaldehyde (2 molecules) with n-butylamine in the absence of a condensing agent is described in an example, and the products obtained with varying molecular proportions of aldehyde, up to 15, are tabulated for propionaldehyde and aniline, and crotonaldehyde and ethylaniline in addition to the products mentioned, above. The properties of the following condensation products, obtained without condensing agents, are also described, the numbers in brackets giving the molecular proportions of aldehyde to amine : acetaldehyde-aniline (5 : 1), n-butyraldehyde-guanidine (5: 1), n-butyraldehyde-ethylamine (5: 1), n-butyraldehyde-diethylamine (5 : 1), n-butyraldehyde ethylaniline (5 : 1), n-butyraldehyde-methylamine (10: 1), n-butyraldehyde-ethylene-diamine (10: 1), nbutyraldehyde-ethylamine (15 : 1), heptaldehydeethylamine (5 : 1), heptaldehyde-o-tolyldiguanide (5: 1), acetaldol-ethylamine (5: 1), acetaldol-nbutylamine (5 : 1), acetaldol-o-tolyldiguanide (5 : 1), crotonaldehyde-aniline (5: 1) and citralo-tolyldiguanide (5: 1). As an example of the use of an acidic condensing agent, the preparation of n-butyraldehyde-aniline (5: 1) in the presence of butyric acid is described, and tables, showing the effect of varying quantities of acid on the progress of the reaction and on the tensile strength of the rubber vulcanized by the product are given. The products obtained by replacing butyric by stearic and sulphuric acids, and by condensing heptaldehyde (3 molecules) with nbutylamine in the presence of n-valeric acid, are also described. The aldehyde may also be used in excess of the amount desired in the product, the excess being removed by distillation. In examples of this modification, the condensation of n-butyraldehyde with aniline or o-toulidine in presence of n-butyric or acetic acid is described. The effect of using acid condensing agents is also shown 'by tabulating the properties of rubber vulcanized with the following condensation products :-butyraldehyde-aniline, in presence of n-butyric, acetic or propionic acid; heptaldehyde with o-tolyldiguanide or ethylamine, in presence of oenanthylic acid: propionaldehyde with aniline, in presence of propionic acid; and heptaldehyde with n-butylamine, in presence of valeric acid. This subject-matter does not appear in the Specification as accepted, but is in part claimed in Specification 263,853.
GB6451/22A 1925-03-13 1926-03-08 Improvements in the vulcanisation of rubber substances Expired GB249113A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US120534XA 1925-03-13 1925-03-13

Publications (1)

Publication Number Publication Date
GB249113A true GB249113A (en) 1927-08-08

Family

ID=21753146

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6451/22A Expired GB249113A (en) 1925-03-13 1926-03-08 Improvements in the vulcanisation of rubber substances

Country Status (2)

Country Link
CH (1) CH120534A (en)
GB (1) GB249113A (en)

Also Published As

Publication number Publication date
CH120534A (en) 1927-06-01

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