DE560395C - Preservative for natural and synthetic rubber - Google Patents

Preservative for natural and synthetic rubber

Info

Publication number
DE560395C
DE560395C DE1930I0013030 DEI0013030D DE560395C DE 560395 C DE560395 C DE 560395C DE 1930I0013030 DE1930I0013030 DE 1930I0013030 DE I0013030 D DEI0013030 D DE I0013030D DE 560395 C DE560395 C DE 560395C
Authority
DE
Germany
Prior art keywords
natural
aging
synthetic rubber
preservative
action
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
DE1930I0013030
Other languages
German (de)
Inventor
Dr Theodor Weigel
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DE1930I0013030 priority Critical patent/DE560395C/en
Priority to GB21803/30A priority patent/GB359045A/en
Priority to FR719076D priority patent/FR719076A/en
Application granted granted Critical
Publication of DE560395C publication Critical patent/DE560395C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/375—Thiols containing six-membered aromatic rings

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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Description

DEUTSCHES REICHGERMAN EMPIRE

AUSGEGEBEN AM 1. OKTOBER 1932ISSUED ON OCTOBER 1, 1932

REICHSPATENTAMTREICH PATENT OFFICE

PATENTSCHRIFTPATENT LETTERING

KLASSE 39 b GRUPPECLASS 39 b GROUP

I. G. Farbenindustrie Akt.-Ges. in Frankfurt a. M.*) Konservierungsmittel für Natur- und synthetischen Kautschuk IG Farbenindustrie Akt.-Ges. in Frankfurt a. M. *) Preservative for natural and synthetic rubber

Patentiert im Deutschen Reiche vom 26. Juni 1930 abPatented in the German Empire on June 26, 1930

In den Einwirkungsprodukten vonSchwefel-In the products of action of sulfur

chlorür S2Cl2 und Schwefelchlorid SCl2 auf aromatische Oxyverbindungen oder deren Kernsubstitutionsprodukte wurde eine neue Klasse von Kautschukkonservierungsmitteln gefunden, die sich außer durch sehr gute Alterungsschutzwirkung besonders dadurch auszeichnen, daß die Kautschukmischungen nach der Vulkanisation nicht verfärbt sindchlorine S 2 Cl 2 and sulfur chloride SCl 2 on aromatic oxy compounds or their core substitution products, a new class of rubber preservatives has been found which, in addition to very good anti-aging properties, is particularly notable for the fact that the rubber compounds are not discolored after vulcanization

ίο und daß die Vulkanisate auch unter dem Einfluß des Lichtes nahezu farblos bleiben.ίο and that the vulcanizates remain almost colorless even under the influence of light.

Diese Einwirkungsprodukte sind in derThese exposure products are in the

Hauptsache Oxydiarylsulfide, z. B. p-Dioxydiphenylsulfid Mainly oxydiaryl sulfides, e.g. B. p-Dioxydiphenyl sulfide

HOHO

-S--S-

-OH-OH

(vgl. Haitinger, Monatshefte für Chemie 4, 166), Dioxydi-ß-naphthylsulfld (vgl. Henriques, Berichte der Deutschen Chemischen Gesellschaft 27, 2993), Dioxyditolylsulfid, also wohldefinierte, kristallisierte Substanzen. Nebenher entstehen jedoch auch nichtkristallisierte Produkte unbekannter Zusammensetzung, bei denen es sich wahrscheinlich um Gemische von Stellungsisomeren bzw. Monosulfiden und bzw. oder Disulfiden und bzw. oder Polvsulfiden handelt. Da diese Substanzen in der Schutzwirkung einander sehr ähnlich sind, ist eine Trennung des anfallenden Gemisches nicht notwendig. (cf. Haitinger, monthly magazine for chemistry 4, 166), Dioxydi-ß-naphthylsulfld (cf. Henriques, reports of the German Chemical Society 27, 2993), Dioxyditolylsulfid, so well-defined, crystallized substances. At the same time, however, non-crystallized products of unknown composition also arise, which are probably mixtures of positional isomers or monosulfides and / or disulfides and / or poly sulfides. Since these substances are very similar in terms of their protective effect, it is not necessary to separate the resulting mixture.

Die neuen Alterungsschutzmittel besitzen gegenüber den Oxygruppen enthaltenden Verbindungen der deutschen Patentschrift 366 114 und der britischen Patentschriften 286 171 und 305 647 den Vorteil einer erheblich stärkeren Alterungsschutzwirkung.The new anti-aging agents have compounds containing oxy groups German patent specification 366 114 and British patent specification 286 171 and 305 647 have the advantage of a considerably stronger anti-aging effect.

Beispielexample

Eine Mischung der Zusammensetzung: 100 Gewichtsteile heller Krepp, 50 Gewichtsteile Lithopone, 5 Gewichtsteile Zinkoxyd, 3,6 Gewichtsteile Schwefel, 1,1 Gewichtsteile Hexamethylentetramin, 0,5 Gewichtsteile Stearinsäure, 1,5 Gewichtsteile Alterungsschutzmittel wurde 45. Minuten auf 31Z2 Atm. geheizt. Mit den erhaltenen Vulkanisaten wurden im Geerofea Alterungsversuche bei 700 angestellt. Nach dieser Methode entsprechen 2 Tage künstlicher Alterung einer natürlichen Alterung von ungefähr 1 Jahr.A mixture of the composition: 100 parts by weight of light crepe, 50 parts by weight of Lithopone, 5 parts by weight of zinc oxide, 3.6 parts by weight of sulfur, 1.1 parts by weight of hexamethylenetetramine, 0.5 part by weight of stearic acid, 1.5 parts by weight of anti-aging agent was added to 3 1 Z 2 for 45 minutes Atm. heated. The obtained vulcanized in Geerofea aging experiments were carried out at 70 0th According to this method, 2 days of artificial aging correspond to natural aging of approximately 1 year.

Bei Verwendung von p-Dioxydiphenylsulfid (A), ρ-Dioxyditolylsulfid (B), Einwirkungsprodukt von Schwefel dichlorid (SCl2) auf ct-Naphthol (C), Einwirkungsprodukt von Schwefelchlorür (S2Cl2) auf a-Naphthol (D),When using p-dioxydiphenyl sulfide (A), ρ-dioxyditolyl sulfide (B), product of the action of sulfur dichloride (SCl 2 ) on ct-naphthol (C), product of the action of sulfur chloride (S 2 Cl 2 ) on a-naphthol (D),

*) Von dem Patentsucher ist als der Erfinder angegeben worden:*) The patent seeker stated as the inventor:

Dr. Theodor Weigel in Köln-Mülheim.Dr. Theodor Weigel in Cologne-Mülheim.

Einwirkungsprodukt von Schwefelchlorür (S2Cl2) auf p-Oxydiphenyl (E), Einwirkungsprodukt von Schwefeldichlorid (S Cl2) auf p-Oxydiphenyl (-F),- Einwirkungsprodukt von Schwefelchlorür (S2Cl2) auf Rohxylenol (G), Einwirkungsprodukt von Schwefeldichlorid (S Cl2) auf Rohxylenol (H) wurden folgende Werte erhalten:Product of the action of sulfur chloride (S 2 Cl 2 ) on p-oxydiphenyl (E), product of the action of sulfur dichloride (S Cl 2 ) on p-oxydiphenyl (-F), - Product of the action of sulfur chloride (S 2 Cl 2 ) on crude xylenol (G), The product of the action of sulfur dichloride (S Cl 2 ) on crude xylenol (H) gave the following values:

ohne
Zusatzwithout
additive AA. BB. ZerreißfestigkeitTensile strength DD. η kg/cm η kg / cm 22 FF. GG HH l0 vor der Alterung
nach 3jähriger Alterung
nach 6 j ähriger Alterung
nach 9Jähriger Alterung l0 before aging
after 3 years of aging
after 6 years of aging
after 9 years of aging 204
126
93
45204
126
93
45 219
150
129219
150
129 217
183
158
140217
183
158
140 CC. 232
195
189
149232
195
189
149 EE. 215
143
107
82215
143
107
82 212
168
128
106212
168
128
106 185
148
134
105185
148
134
105 226
195
185
177226
195
185
177 230
169
114
87230
169
114
87

Claims (1)

Patentanspruch:Claim: Alterungsschutzmittel für Natur- oder synthetischen Kautschuk, bestehend aus Einwirkungsprodukten von Schwefelchlorür (S2Cl2) oder Schwefelchlorid (S Cl2) auf aromatische Oxyverbindungen oder deren Kernsubstitutionsprodukte.Anti-aging agent for natural or synthetic rubber, consisting of the action products of sulfur chloride (S 2 Cl 2 ) or sulfur chloride (S Cl 2 ) on aromatic oxy compounds or their core substitution products.
DE1930I0013030 1930-06-26 1930-06-26 Preservative for natural and synthetic rubber Expired DE560395C (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE1930I0013030 DE560395C (en) 1930-06-26 1930-06-26 Preservative for natural and synthetic rubber
GB21803/30A GB359045A (en) 1930-06-26 1930-07-18 Process for preserving rubber and artificial rubber-like masses
FR719076D FR719076A (en) 1930-06-26 1931-06-24 Agents and methods for preserving natural rubber species and rubber-like masses

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1930I0013030 DE560395C (en) 1930-06-26 1930-06-26 Preservative for natural and synthetic rubber
GB21803/30A GB359045A (en) 1930-06-26 1930-07-18 Process for preserving rubber and artificial rubber-like masses

Publications (1)

Publication Number Publication Date
DE560395C true DE560395C (en) 1932-10-01

Family

ID=10169070

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1930I0013030 Expired DE560395C (en) 1930-06-26 1930-06-26 Preservative for natural and synthetic rubber

Country Status (3)

Country Link
DE (1) DE560395C (en)
FR (1) FR719076A (en)
GB (1) GB359045A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE900388C (en) * 1941-05-27 1953-12-28 Monsanto Chemicals Process for the preservation of rubber

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2470545A (en) * 1944-06-22 1949-05-17 Monsanto Chemicals Vulcanizing rubber
US2726277A (en) * 1950-06-10 1955-12-06 Monsanto Chemicals Antioxidant
US2731443A (en) * 1952-09-20 1956-01-17 Firestone Tire & Rubber Co Vulcanized rubber stabilized with a mixture of a di(hydroxyphenyl) sulfide and a di(alkylhydroxyphenyl) methane

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE900388C (en) * 1941-05-27 1953-12-28 Monsanto Chemicals Process for the preservation of rubber

Also Published As

Publication number Publication date
GB359045A (en) 1931-10-19
FR719076A (en) 1932-02-02

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