DE1289317B - Improving the oxidation resistance of polymers - Google Patents

Improving the oxidation resistance of polymers

Info

Publication number
DE1289317B
DE1289317B DEE27992A DEE0027992A DE1289317B DE 1289317 B DE1289317 B DE 1289317B DE E27992 A DEE27992 A DE E27992A DE E0027992 A DEE0027992 A DE E0027992A DE 1289317 B DE1289317 B DE 1289317B
Authority
DE
Germany
Prior art keywords
parts
polymers
improving
bis
oxidation resistance
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.)
Pending
Application number
DEE27992A
Other languages
German (de)
Inventor
Filbey Allen Howard
Coffield Thomas Hunter
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.)
Ethyl Corp
Original Assignee
Ethyl Corp
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
Priority claimed from US536316A external-priority patent/US2962531A/en
Priority claimed from US536315A external-priority patent/US2944086A/en
Application filed by Ethyl Corp filed Critical Ethyl Corp
Publication of DE1289317B publication Critical patent/DE1289317B/en
Pending legal-status Critical Current

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    • C10N2040/12—Gas-turbines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C—CHEMISTRY; METALLURGY
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Description

Als Mittel zur Verbesserung der Oxydationsbeständigkeit von Polymeren sind zahlreiche Produkte bekannt. Zum Stand der Technik werden genannt: Phenyl-p-naphthylamin, das Umsetzungsprodukt von Phenol und Styrol, das Umsetzungsprodukt von Diphenylamin und Aceton, das Umsetzungsprodukt von Phenol und Diisobutylen, das Umsetzungsprodukt eines Alkylphenols und Phosphortrichlorids, alkyliertes Diphenylamin, ferner 2,2'-Methylen-bis-(4-methyl-6-tert.-butylphenol), ein vielfach benutztes Antioxydationsmittel für Polybutadiene. As a means of improving the oxidation resistance of polymers numerous products are known. The prior art includes: phenyl-p-naphthylamine, the reaction product of phenol and styrene, the reaction product of diphenylamine and acetone, the reaction product of phenol and diisobutylene, the reaction product an alkylphenol and phosphorus trichloride, alkylated diphenylamine, also 2,2'-methylene-bis- (4-methyl-6-tert-butylphenol), a widely used antioxidant for polybutadienes.

Erfindungsgegenstand ist die Verwendung von 1,1 - Bis - (3,5- dialkyl-4 - hydroxyphenyl)- methanen, deren Alkylgruppen 3 bis 8 C-Atome enthalten und jeweils am a-C-Atom verzweigt sind, als Mittel zur Verbesserung der Oxydationsbeständigkeit von natürlichen und künstlichen Kautschuken und anderen Polymeren. The subject of the invention is the use of 1,1 - bis (3,5-dialkyl-4 - hydroxyphenyl) - methanes, the alkyl groups of which contain 3 to 8 carbon atoms and each are branched on the a-C atom, as a means of improving the oxidation resistance of natural and artificial rubbers and other polymers.

In vielfachen Untersuchungen haben diese Verbindungen, insbesondere 1,1-Bis-(3,5-di-tert.-butyl-4-hydroxyphenyl)-methan, wertvolle, den bisher im Handel bekanntgewordenen Produkten überlegene Eigenschaften, als Antioxydationsmittel für natürliche und synthetische Kautschukarten, gezeigt. Dem bekannten 2,2'-Methylen-bis- (4-methyl-6-tert.-butylphenol) gegenüber zeigt es keine Verfärbung nach 168stündigem Test bei 100°c. auch UV-Licht gegenüber ist es weniger zu Verfärbungen neigend. Die Überlegenheit bei Ofentests bei 150°C ist besonders zu erwähnen. Die wesentlich verlängerte Induktionszeit bei Polyäthylen und Polypropylen zeigt die Tabelle III. In multiple studies, these compounds have, in particular 1,1-bis- (3,5-di-tert-butyl-4-hydroxyphenyl) methane, valuable ones that have been commercially available up to now products that have become known have superior properties as antioxidants for natural and synthetic rubbers. The well-known 2,2'-methylene-bis- (4-methyl-6-tert-butylphenol) on the other hand, it shows no discoloration after 168 hours Test at 100 ° C. it is also less prone to discoloration compared to UV light. The superiority in oven tests at 150 ° C deserves special mention. The essential Table III shows extended induction times for polyethylene and polypropylene.

Der Erfinder hat bei Versuchen mit einer anderen unter die Erfindung fallenden Verbindung - 1,1-Bis-(3,5-diisopropyl-4-hdyrophenyl)-methan - ähnlich lange Induktionszeiten von 32 Stunden gemessen. The inventor has in experiments with another under the invention falling compound - 1,1-bis- (3,5-diisopropyl-4-hdyrophenyl) -methane - similar long induction times of 32 hours were measured.

Zur Frage der Erfindungshöhe wird darauf hingewiesen, daß die bisher in der Technik verwendeten Produkte zur Verhinderung einer Oxydation bei Polymeren eine Vielzahl von chemischen Verbindungen darstellen, aus denen eine Forschungsrichtung sich nicht ergibt. Voraussagen hinsichtlich einer Verbesserung der vielfältigen auf diesem Gebiete verlangten Eigenschaften von Antioxydationsmitteln ließen sich nicht machen. Die neuen Produkte stellen wertvolle, aber in ihren Gesamteigenschaften nicht voraussehbare Lösungen eines stark bearbeiteten Problems dar. Regarding the question of the level of invention, it is pointed out that the so far Products used in technology to prevent oxidation in polymers represent a multitude of chemical compounds that make up a research direction does not surrender. Predictions of an improvement in the diverse The properties of antioxidants required in this area can be found not do. The new products represent valuable, but in their overall properties unpredictable solutions to a heavily processed problem.

Die erfindungsgemäß zu verwendenden Verbindungen werden im allgemeinen in Mengen von 0,001 bis 3,0 Gewichtsprozent in dem zu stabilisierenden Material verwendet. The compounds to be used according to the invention are in general in amounts of 0.001 to 3.0 percent by weight in the material to be stabilized used.

Die nachfolgenden Beispiele erläutern die Erfindung. The following examples illustrate the invention.

Sie erläutern aber weder bevorzugte Verbindungen noch bevorzugte Zusatzmengen.However, they explain neither preferred compounds nor preferred additional amounts.

Beispiele A. Naturkautschuk (weiß und schwarz) Styrol-Butadien-Kautschuk Naturkautschuk und synthetischer Kautschuk wurden mit den in TabelleI wiedergegebenen Mengen formuliert. Dem Latex wurde 1,1-Bis-(3 ,5-di-tert.-butyl-hydroxyphenyl)-methan zugegeben und die Kautschuke 30, 45, 60 oder 90 Minuten lang bei 135°C vulkanisiert (s. Tabelle II). Examples A. Natural rubber (white and black) styrene-butadiene rubber Natural rubber and synthetic rubber were made with those shown in Table I. Quantities formulated. 1,1-bis- (3,5-di-tert-butyl-hydroxyphenyl) methane was added to the latex added and the rubbers vulcanized for 30, 45, 60 or 90 minutes at 135 ° C (see Table II).

Die Zugfestigkeit und Dehnung wurde nach ASTM-D 412 gemessen. Künstliche Alterung wurde in folgender Weise vorgenommen. The tensile strength and elongation were measured according to ASTM-D 412. Artificial Aging was done in the following manner.

A. 48 Stunden bei 100°C (ASTM-D 573). A. 48 hours at 100 ° C (ASTM-D 573).

B. 168 Stunden bei 70°C unter 135 kg Sauerstoffdruck. B. 168 hours at 70 ° C under 135 kg oxygen pressure.

C. 96 Stunden bei 700 C unter 135 kg Sauerstoffdruck. C. 96 hours at 700 C under 135 kg oxygen pressure.

Tabelle 1 gibt die Zusammensetzung der formulierten Kautschuke wieder. In Tabelle II sind die Ergebnisse in Prozenten der Erhaltung der physikalischen Eigenschaften nach der Alterung wiedergegeben. Je höher die Prozentzahl, um so wirksamer hat sich der Zusatz erwiesen. Table 1 shows the composition of the formulated rubbers. In Table II the results are as percentages of physical retention Properties reproduced after aging. The higher the percentage, the more effective has proved the addition.

Tabelle I Zusammensetzung der Kautschukformulierungen Weißer Naturkautschuk Heller Krepp-K ................ 100,00 Teile Bleifreies, gepulvertes Zinkoxyd 50,00 Teile Titandioxyd ................ 25,000 Teile Stearinsäure ................ ... 2,00 Teile Ultramarinblau ..... ................ 0,12 Teile Schwefel ................ ................ 3,00 Teile 2-Mercaptobenzthiazol (Beschleungier).... ................ 1,00 Teil Gesamt .................... ................ 181,12 Teile Schwarzer Naturkautschuk Naturkautschuk K................ 100,00 Teile Ruß ................ 45,00 Teile Zinkoxyd ................ ...... 5,00 Teile Stearinsäure ................ .... 3,00 Teile Kiefernteer ................ 2,00 Teile Schwefel ................ ..... 3,00 Teile 2-Mercaptobenzthiazol (Beschleuniger) ................ 9,65 Teile Gesamt ................ ........ 167,65 Teile Styrol-Butadien-Kautschuk Kautschuk ................ ...... 100,00 Teile Zinkoxyd ................ ...... 3,00 Teile Stearinsäure ................ .... 1,00 Teil Hochabriebfester Ofenruß 50,00 Teile Naphthenöl ................ .... 8,00 Teile Schwefel ................ ....... 2,00 Teile N-Cyclohexyl-2-benzthiazolsulfonamid ................ ... 1,00 Teil Gesamt ................ ....... 165,00 Teile Tabelle II - Ergebnisse Vulkani- Teile 1,1-Bis- Zug- Deh- Kautschuk sation (3,5-dialkyl- Alterung festig- 4-hydroxyphenyl) nung methan keit ng (1) ohne A 53 68 (1) 2,00 A 68 71 Weißer Naturkautschuk ................ # (1) ohne B 81 92 (1) 1,00 B 93 95 (2) ohne C 17,6 51 Schwarzer naturkautschuk ................ # (2) 1,00 C 22 62 (3) 0,50 A 69 43 Styrol-Butadien-kautschuk ................ (3) 0,70 A 71 47 (1) 30 und 45 Minuten. (2) 45, 60 und 90 Minuten. (3) 45 und 60 Minuten. Table I Composition of the rubber formulations White natural rubber Light crepe K ................ 100.00 parts lead-free, powdered zinc oxide 50.00 parts titanium dioxide .......... ...... 25,000 parts of stearic acid ................ ... 2.00 parts of ultramarine blue ..... ............ .... 0.12 parts sulfur ................ ................ 3.00 parts 2-mercaptobenzothiazole (Beschleungier ) .... ................ 1.00 part total .................... .... ............ 181.12 parts black natural rubber natural rubber K ................ 100.00 parts carbon black ......... ....... 45.00 parts of zinc oxide ................ ...... 5.00 parts of stearic acid ........... ..... .... 3.00 parts pine tar ................ 2.00 parts sulfur ............... . ..... 3.00 parts of 2-mercaptobenzothiazole (accelerator) ................ 9.65 parts total ............. ... ........ 167.65 parts styrene-butadiene rubber ................ ...... 100.00 parts zinc oxide .. .............. ...... 3.00 parts of stearic acid e ................ .... 1.00 part highly abrasion-resistant furnace soot 50.00 parts naphthene oil ................ .. .. 8.00 parts of sulfur ................ ....... 2.00 parts of N-cyclohexyl-2-benzothiazolesulfonamide ......... ....... ... 1.00 part Total ................ ....... 165.00 parts Table II - Results Vulcani- parts 1,1-bis- tensile- Rubber sation (3,5-dialkyl- aging strength- 4-hydroxyphenyl) tion methane ng (1) without A 53 68 (1) 2.00 A 68 71 White natural rubber ................ # (1) without B 81 92 (1) 1.00 B 93 95 (2) excluding C 17.6 51 Black natural rubber ................ # (2) 1.00 C 22 62 (3) 0.50 A 69 43 Styrene butadiene rubber ................ (3) 0.70 A 71 47 (1) 30 and 45 minutes. (2) 45, 60 and 90 minutes. (3) 45 and 60 minutes.

B. Polymere (Polyäthylen und Polypropylen) (Sauerstoffaufnahme) Eine bestimmte Menge 1,1-Bis-(3,5-di-tert.-butylhydroxyphenyl)-methan wurde mit dem Polyolefin gemischt, indem man eine abgewogene Menge Plastikkügelchen in einem Walzwerk behandelt. Das Antioxydationsmittel wurde erst zugegeben, nachdem das Polyolefin kurze Zeit vorgewalzt worden war. Nach dem Walzen wurde das Polyolefin in einer abgewogenen Menge in ein geeichtes Gefäß gefüllt und geschmolzen. Das Gefäß wurde dann verschlossen. B. Polymers (polyethylene and polypropylene) (oxygen uptake) A A certain amount of 1,1-bis- (3,5-di-tert-butylhydroxyphenyl) methane was mixed with the polyolefin mixed by treating a weighed amount of plastic beads in a roller mill. The antioxidant was only added after the polyolefin was a short time had been rolled. After rolling, the polyolefin was weighed in one Amount filled into a calibrated vessel and melted. The jar was then sealed.

Es war durch ein Kapillarrohr mit einer Gasbürette und einer Niveaullasche verbunden. Die ganze Vorrichtung wurde mit Sauerstoff ausgespült, verschlossen und auf 600 C erhitzt. Mittels der Niveauflasche wurde der Sauerstoffdruck auf 1 atm gehalten. Während des Versuchs wurde die Sauerstoffaufnahme bei der erhöhten Temperatur gemessen. Diese Versuchsanordnung wurde gewählt, weil gefunden worden ist, daß viele Stoffe die Oxydation während einer Induktionszeit verhindern und daß dann eine sehr scharfe Aufwärtsbewegung in der Sauerstoffaufnahme eintritt, also das Antioxydationsmittel verbraucht ist.It was through a capillary tube with a gas burette and a level tab tied together. The entire device was purged with oxygen, sealed and heated to 600 C. Using the level bottle, the oxygen pressure was set to 1 atm held. During the experiment, the oxygen uptake was reduced at the elevated temperature measured. This design was chosen because it has been found that many Substances which prevent oxidation during an induction period and then a very sharp upward movement occurs in the oxygen uptake, i.e. the antioxidant is used up.

Die Menge des Zusatzes des Antioxydationsmittels betrug 0,05 Gewichtsprozent der Polyolefinmenge. The amount of the antioxidant addition was 0.05% by weight the amount of polyolefin.

Tabelle III Induktions- Polyolefin Zusatz zeit in Stunden Polyäthylen ohne 2 1 ,1-Bis-(3,5-di-tert.- butyl-hydroxy- phenyl)-methan 40 Polypropylen ohne 0 1,1-Bis-(3,5-di-tert.- butyl-hydroxy- phenyl)-methan 20 Table III Induction Polyolefin addition time in hours Polyethylene without 2 1, 1-bis- (3,5-di-tert.- butyl-hydroxy phenyl) methane 40 Polypropylene without 0 1,1-bis- (3,5-di-tert.- butyl-hydroxy phenyl) methane 20

Claims (1)

Patentanspruch : Verwendung von 1,1-Bis-(3,5-dialkyl-4-hdyroxyphenyl)-methanen, deren Alkylgruppen 3 bis 8 C-Atome enthalten und jeweils am oc-C-Atom verzweigt sind, als Mittel zur Verbesserung der Oxydationsbeständigkeit von natürlichen und künstlichen Kautschuken und anderen Polymeren.Claim: Use of 1,1-bis (3,5-dialkyl-4-hdyroxyphenyl) methanes, the alkyl groups of which contain 3 to 8 carbon atoms and are each branched on the oc-carbon atom are, as a means of improving the oxidation resistance of natural and artificial rubbers and other polymers.
DEE27992A 1955-09-23 1956-09-18 Improving the oxidation resistance of polymers Pending DE1289317B (en)

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US536316A US2962531A (en) 1955-09-23 1955-09-23 3, 5-dialkyl-4-hydroxy benzylamines
US536315A US2944086A (en) 1955-09-23 1955-09-23 1, 1-bis(3, 5-dialkyl-4-hydroxyphenyl) methanes

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DE4013113A1 (en) * 1990-04-25 1991-10-31 Bayer Ag Stabilised ABS-aromatic polycarbonate moulding compsns. - contg. specified bisphenol additives to prevent high temp. surface defects and to improve impact strength

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US2414729A (en) * 1943-08-28 1947-01-21 Standard Oil Dev Co Process of preparing a metallic phenolate salt of a hydroxyarylalkylamine product
US2538355A (en) * 1949-07-25 1951-01-16 American Cyanamid Co 2, 2'-alkylene bis-4, 6-dialkyl phenols as rubber stabilizers
US2591651A (en) * 1949-11-21 1952-04-01 Standard Oil Dev Co Stabilized organic compositions containing bis (hydroxy alkoxy phenyl) alkanes
US2734088A (en) * 1955-11-23 1956-02-07 Monomeric condensation products of

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DE4013113A1 (en) * 1990-04-25 1991-10-31 Bayer Ag Stabilised ABS-aromatic polycarbonate moulding compsns. - contg. specified bisphenol additives to prevent high temp. surface defects and to improve impact strength

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