DE745032C - Method for producing a synthetic rubber - Google Patents

Method for producing a synthetic rubber

Info

Publication number
DE745032C
DE745032C DEI61551D DEI0061551D DE745032C DE 745032 C DE745032 C DE 745032C DE I61551 D DEI61551 D DE I61551D DE I0061551 D DEI0061551 D DE I0061551D DE 745032 C DE745032 C DE 745032C
Authority
DE
Germany
Prior art keywords
oxygen
butadiene
ketone
secondary amine
radical
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
DEI61551D
Other languages
German (de)
Inventor
Dr Wilhelm Becker
Dr Heinz Wollthan
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 DEI61551D priority Critical patent/DE745032C/en
Application granted granted Critical
Publication of DE745032C publication Critical patent/DE745032C/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Description

Verfahren zur Herstellung eines synthetischen Kautschuks Es wurde gefunden, daß wertvolle Polymerisationsprodukte erhalten werden, wenn man Butadien-i # 3. im Gemisch mit Methylvinylketon in saurem Medium in Gegenwart von Sauerstoff bzw. sauerstoffabgebenden Katalysatoren der Emulsionspolymerisation unterwirft, wobei das Methylvinylketon`mindestens in Mengen von 25 °/o der Gesamtmengen an polymerisierbaren Stoffen (Methylvinylketon + Butadien) zugegen. sein soll. Vorzugsweise arbeitet man bei gewöhnlicher Temperatur oder bei mäßig erhöhter Temperatur. Die Reaktionskomponenten werden vorzugsweise im Verhältnis i : i angewandt. Es empfiehlt sich, in Gegenwart von Polymerisationsreglern zu arbeiten. Ausgenommen ist das zum Gegenstand des Patents 702 749 gehörende Arbeiten unter Verwendung solcher Emulgiermittel, welche wasserlösliche Salze von Verbindungen der allgemeinen Formel 'X-CH2-CH2=F-CH2-CH2-NZ darstellen, worin Y Sauerstoff oder Schwefel, NZ den Rest eines sekundären Amins oder einer quaternären Ammoniumverbindung, X den Rest eines sekundären Amins, eines Säureamids, eines Esters, eines Äthers oder eine Hydroxylgruppe bedeutet, wobei in wenigstens einem der Reste X und Z mindestem 8 Kohlenstoffatome in nichtcyclischer Bindung direkt miteinander verbunden sind.Process for the production of a synthetic rubber It has been found that valuable polymerization products are obtained if butadiene-i # 3. In a mixture with methyl vinyl ketone in an acidic medium in the presence of oxygen or oxygen-releasing catalysts is subjected to emulsion polymerization, the methyl vinyl ketone being at least in quantities of 25% of the total amount of polymerizable substances (methyl vinyl ketone + butadiene) is present. should be. It is preferred to work at an ordinary temperature or at a moderately elevated temperature. The reaction components are preferably used in the ratio i: i. It is advisable to work in the presence of polymerization regulators. This does not apply to the work belonging to the subject of patent 702 749 using emulsifiers which represent water-soluble salts of compounds of the general formula X-CH2-CH2 = F-CH2-CH2-NZ, in which Y is oxygen or sulfur, NZ is the remainder of one secondary amine or a quaternary ammonium compound, X denotes the radical of a secondary amine, an acid amide, an ester, an ether or a hydroxyl group, where in at least one of the radicals X and Z at least 8 carbon atoms are directly connected to one another in a noncyclic bond.

Die erhältlichen Polymerisate vereinigen gute kautschukähnliche Eigenschaften mit einer hervorragenden Beständigkeit (im vulkanisierten Zustand) gegen aliphatische oder aromatische Kohlenwasserstoffe. Sie heben sich in dieser Beziehung aus der allgemeinen Klasse der Mischpolymerisate von Butadienen mit ungesättigten K etonen heraus (s. Patentschrift 543 343). Beispiel i 25 Gewichtsteile Vinylmethylketon und 75 Gewichtsteile Butadien werden in einer wäßrigen Emulsion, die aus 3 Gewichtsteilen salzsaurem Dodecylamin oder Octadecyldimethylamin, Zoo Gewichtsteilen Wasser und o,i5 Gewichtsteilen Ammoniumpersulfat besteht, bei 3o° polymerisiert. Nach i bis z Tagen wird eine Polymerisationsausbeute von 8o'/, erhalten. - Beispiel 2 5o Gewichtsteile Butadien werden in einer Lösung von 5o Gewichtsteilen Vinylmethylketon in i5o Gewichtsteilen einer 30/0i,-en Dodecylaminchlorhydratlösung, die mit 3 Gewichtsteilen io°/oiger Ammonpersulfatlösung versetzt ist, emulgiert und 3 Tage bei 3o° geschüttelt. Man erhält in nahezu quantitativer Ausbeute ein Polymerisat, welches bei guten mechanischen Eigenschaften eine ausgezeichnete Benzin- und Benzolbeständigkeit besitzt. EeiZusatz von o,2 Gewichtsteilen Diisopropylxanthogendisulfid erhält man unter sonst gleichen Polymerisationsbedingungen ein Polymerisat von hervorragenden plastischen Eigenschaften.The polymers available combine good rubber-like properties with excellent resistance (in the vulcanized state) to aliphatic or aromatic hydrocarbons. You stand out in this relationship general class of copolymers of butadienes with unsaturated ketones out (see patent specification 543 343). Example i 25 parts by weight of vinyl methyl ketone and 75 parts by weight of butadiene are in an aqueous emulsion consisting of 3 parts by weight hydrochloric acid dodecylamine or octadecyldimethylamine, zoo parts by weight of water and o, 15 parts by weight of ammonium persulfate, polymerized at 3o °. After i to A polymerization yield of 80% is obtained for two days. - Example 2 50 parts by weight of butadiene are added to a solution of 50 parts by weight Vinyl methyl ketone in 150 parts by weight of a 30 / 0i, -en dodecylamine chlorohydrate solution, which is mixed with 3 parts by weight of 10% ammonium persulfate solution, emulsified and shaken for 3 days at 30 °. A virtually quantitative yield is obtained Polymer, which has good mechanical properties and excellent gasoline and has benzene resistance. Addition of 0.2 parts by weight of diisopropylxanthogen disulfide a polymer of excellent quality is obtained under otherwise identical polymerization conditions plastic properties.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines synthetischen Kautschuks aus Butadienkohlenwasserstoffen und ungesättigten Ketonen, dadurch gekennzeichnet, dafi Butadien im Gemisch mit Methylvinylketon in saurem Medium der Emulsionspolymerisation in Gegenwart von Sauerstoff oder sauerstoffabgebenden Katalysatoren unterworfen wird, wobei das Vinylmethylketon mindestens in "Mengen Von 25 °,!" der Gesamtmengen an polymerisierbaren Stoffen (Vinylmethylketon -!- ßudadien) zugegen sein soll und das Arbeiten in Gegenwart solcher Emulgatoren ausgeschlossen ist, welche wasserlösliche Salze von Verbindungen der allgemeinen Formel X- CH,-CH.-F- CH.- CH>-NZ darstellen, worin 1.` Sauerstoff oder Schwefel, NZ den Rest eines sekundären Amins oder einer quaternären Ammoniumverbindung, X den Rest eine: sekundären Amins, eines Säureamids, eines Esters, eines Äthers oder einer quaternären Amtnoniumverbindung oder eine Hydroxylgruppe bedeutet, wobei in wenigstens einem der Reste X und Z mindestens 8 Kohlenstoffatome in nichtcvclischer Findung direkt miteinander verbunden sind. Zur Abgrenzung des Anmeldungsgegenstandes vom Stand der Technik sind im Erteilungsverfahren folgende Druckschriften in Betracht gezogen worden: deutsche Patentschrift .. .. . Nr. 5-3 343-französische - ..... - 803563. PATENT CLAIM: Process for the preparation of a synthetic rubber from butadiene hydrocarbons and unsaturated ketones, characterized in that butadiene in a mixture with methyl vinyl ketone in an acidic medium is subjected to emulsion polymerization in the presence of oxygen or oxygen-releasing catalysts, the vinyl methyl ketone being subjected to at least "amounts of 25 °!"" the total amounts of polymerizable substances (vinyl methyl ketone -! - ßudadiene) should be present and working in the presence of emulsifiers which contain water-soluble salts of compounds of the general formula X- CH, -CH.-F- CH.- CH> -NZ represent, wherein 1.` oxygen or sulfur, NZ the radical of a secondary amine or a quaternary ammonium compound, X the radical of a: secondary amine, an acid amide, an ester, an ether or a quaternary ammonium compound or a hydroxyl group, where in at least one the radicals X and Z are at least 8 carbon atoms directly linked to one another in a noncvclic finding. To distinguish the subject of the application from the state of the art, the following publications were considered in the granting procedure: German patent specification .. ... No. 5-3 343 - French - ..... - 803563.
DEI61551D 1938-06-05 1938-06-05 Method for producing a synthetic rubber Expired DE745032C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI61551D DE745032C (en) 1938-06-05 1938-06-05 Method for producing a synthetic rubber

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI61551D DE745032C (en) 1938-06-05 1938-06-05 Method for producing a synthetic rubber

Publications (1)

Publication Number Publication Date
DE745032C true DE745032C (en) 1944-02-24

Family

ID=7195487

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI61551D Expired DE745032C (en) 1938-06-05 1938-06-05 Method for producing a synthetic rubber

Country Status (1)

Country Link
DE (1) DE745032C (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE543343C (en) * 1930-01-21 1932-02-04 Ig Farbenindustrie Ag Process for the preparation of rubber-like compositions from butadiene hydrocarbons
FR803563A (en) * 1935-03-23 1936-10-03 Ig Farbenindustrie Ag Polymerization products and their production process

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE543343C (en) * 1930-01-21 1932-02-04 Ig Farbenindustrie Ag Process for the preparation of rubber-like compositions from butadiene hydrocarbons
FR803563A (en) * 1935-03-23 1936-10-03 Ig Farbenindustrie Ag Polymerization products and their production process

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