DE2017963A1 - Polyolefin blend stabilised with bisphenol-t - Google Patents
Polyolefin blend stabilised with bisphenol-tInfo
- Publication number
- DE2017963A1 DE2017963A1 DE19702017963 DE2017963A DE2017963A1 DE 2017963 A1 DE2017963 A1 DE 2017963A1 DE 19702017963 DE19702017963 DE 19702017963 DE 2017963 A DE2017963 A DE 2017963A DE 2017963 A1 DE2017963 A1 DE 2017963A1
- Authority
- DE
- Germany
- Prior art keywords
- ester
- bisphenol
- acid
- polyolefin
- stabilised
- 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
Links
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 11
- 239000000203 mixture Substances 0.000 title claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 12
- 238000000465 moulding Methods 0.000 claims abstract description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- -1 polypropylene Polymers 0.000 abstract description 20
- 239000003381 stabilizer Substances 0.000 abstract description 19
- 239000004743 Polypropylene Substances 0.000 abstract description 7
- 238000000605 extraction Methods 0.000 abstract description 7
- 229920001155 polypropylene Polymers 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002195 synergetic effect Effects 0.000 abstract description 3
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003508 Dilauryl thiodipropionate Substances 0.000 abstract description 2
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 abstract description 2
- 239000002530 phenolic antioxidant Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- KYGRYOUHOAXZCT-UHFFFAOYSA-N 4-dodecylbenzenethiol Chemical compound CCCCCCCCCCCCC1=CC=C(S)C=C1 KYGRYOUHOAXZCT-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PDZKGCCWJWFWJX-UHFFFAOYSA-N 5-butan-2-yl-2-methylphenol Chemical compound CCC(C)C1=CC=C(C)C(O)=C1 PDZKGCCWJWFWJX-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
- C08K5/38—Thiocarbonic acids; Derivatives thereof, e.g. xanthates ; i.e. compounds containing -X-C(=X)- groups, X being oxygen or sulfur, at least one X being sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Stabilisierte Formmassen aus Polyolefinen Es ist bekannt, daß zum Stabilisieren von Kunststoffen haufig Phenolderivate und organische Sulfide verwendet werden. Die Wirksamkeit mancher Stabilisatören laßt sich durch gleichzeitigen Zusatz von Vertretern andersartiger Stabilisatorklassen sehr wensentlich steigern. Solche syhergistischen Systeme zeichnen sich dadurch aus, daß ihre Wirksamkeit die Summe der Wirksankeiten der einzelnen Stabilisatorkomponeneten übertrifft.Stabilized molding compositions made from polyolefins It is known that for Phenol derivatives and organic sulfides are often used to stabilize plastics will. The effectiveness of some stabilizers can be increased by adding them at the same time by representatives of different types of stabilizer classes increase very significantly. Such Syhergistic systems are characterized by the fact that their effectiveness is the sum the effectiveness of the individual stabilizer components exceeds.
Aus der deutschen Patentschrift 1.163.017 ist es bekannt, daß Bis-phenol-alkansäureester sehr wirksame Antioxydantien für Polyolefine sind, die entsprechend den deutschen Patentschriften 1.188.799 und 1.188.800 mit Sulfiden einen guten Synergismus zeigen.From German patent 1,163,017 it is known that bis-phenol-alkanoic acid esters very effective antioxidants for polyolefins are according to the German Patents 1,188,799 and 1,188,800 show good synergism with sulfides.
Es wurde nun gefunden, daß stabilisierte Formmassen aus Polyolefineni die o,'oi bis 3 Gew.-%, bezogen auf das Polyolefin, eines Bis-phenolthioalkansäure-S-esters der allgemeinen Formel enthalten, wobei R1 und R2 unabhängig voneinander Wasserstoffatome oder Alkylreste mit 1 - 6 Kohlenstoffatomen, und R3 einen geradkettigen oder verzweigten Kohlenwasserstoffrest mit 1 - 20 Kohlenstoffatomen, eine Arylgruppe, eine Aralkyl- oder Alkylarylgruppe mit 7 - 18 Kohlenstoffatomen und n t - 5 bedeuten, hervorragende Eigenschaften haben.It has now been found that stabilized molding compositions made from polyolefins contain 0.1 to 3% by weight, based on the polyolefin, of a bis-phenolthioalkanoic acid S-ester of the general formula contain, where R1 and R2 are independently hydrogen atoms or alkyl radicals with 1 - 6 carbon atoms, and R3 is a straight-chain or branched hydrocarbon radical with 1 - 20 carbon atoms, an aryl group, an aralkyl or alkylaryl group with 7-18 carbon atoms and nt - 5, excellent Have properties.
Die erfindungsgemäßen Stabilisatoren haben den Vorteil, daß Schwefel und phenolische Komponente in einem Molekül vereinigt sind. Bei Mischungen aus phenolischen Stabilisatoren und schwefelhaltigen Co-Stabilisatoren wird meist die eine Komponente schneller verbraucht als die andere.The stabilizers according to the invention have the advantage that sulfur and phenolic component are combined in one molecule. In the case of mixtures of phenolic Stabilizers and sulfur-containing co-stabilizers will mostly be one component consumed faster than the other.
Dies kann durch unterschiedliche Auswanderung aus dem Polymeren, durch unterschiedliche Flüchtigkeit oder Extraktionsgeschwindigkeit der beiden Komponenten bedingt sein und führt natürlich zum Nachlassen der synergistischen Wirkung.This can be due to different levels of migration from the polymer different volatility or extraction rate of the two components be conditional and of course leads to a decrease in the synergistic effect.
Die erfindungsgemäßen Mischungen sind deshalb vor allem für Anwendungen vorteilhaft, bei denen das Material mit Lösungsmitteln, z.B. heißem Wasser, in Berührung kommt, z.B. Heißwasserrohre, Vasch- und Spülmaschinenteile und Fasern.The mixtures according to the invention are therefore primarily for applications where the material comes into contact with solvents, e.g. hot water comes, e.g. hot water pipes, washing machine and dishwasher parts and fibers.
Die erstellung der erfindungsgemäßen Stabilisatoren erfolgt durch Kondensation von schwefelhaltigen Ketocarbonsäureestern, vor allem Acetessigsäusreestern mit Phenolen in Gegenwart von sauren Kondensationskatalysatoren.The stabilizers according to the invention are prepared by Condensation of sulfur-containing ketocarboxylic acid esters, especially acetoacetic acid esters with phenols in the presence of acidic condensation catalysts.
FÜr die KonCensation werden z.B. folgende Phenole eingesetzt: Phenol, o-Kresol , 2-Isopropylpllenol, 2-sek.Butylphenol, 2-tert Butylphenol, 2-Methyl-5-sek -butylphenol, 2-Methyl-5-tert.-butylphenol, 2,6-Dimethylphenol und 2,6- Diisopropylphenol.For example, the following phenols are used for the condensation: phenol, o-cresol, 2-isopropylpllenol, 2-sec-butylphenol, 2-tert-butylphenol, 2-methyl-5-sec -butylphenol, 2-methyl-5-tert.-butylphenol, 2,6-dimethylphenol and 2,6- Diisopropylphenol.
Die Herstellung der schwefelhaltigen Ketocarbonsäureester geschieht durch Anlagerung von Diketen an lineare oder verzweigte aliphatische Merkaptane wie z.B.: Methyl-, thyl-, Butyl-, sek.Butyl-, n-Octyl-, tert.Octyl-, Lauryl-, tert.The sulfur-containing ketocarboxylic acid esters are produced by adding diketene to linear or branched aliphatic mercaptans such as: methyl, ethyl, butyl, sec-butyl, n-octyl, tert-octyl, lauryl, tert.
Dodecyl- und Stearyl-mercaptan; an aromatische Mercaptane wie z.B.: Thiophenol, Thiokresole, 4-Dodecyl-thiophenol; Thio-α-naphthol, Thio-ß-naphthol, oder durch Herstellung des Säurechlorids der Ketocarbonsäure und anschließende Umsetzung mit dem gewünschten Mercaptid.Dodecyl and stearyl mercaptan; to aromatic mercaptans such as: Thiophenol, thiocresols, 4-dodecyl-thiophenol; Thio-α-naphthol, thio-ß-naphthol, or by preparing the acid chloride of the ketocarboxylic acid and subsequent reaction with the desired mercaptide.
Als besonders bevorzugte Bisphenol-thioalkansäureS-e ster seien beispielsweise folgende Verbindungen aufgeführt: 3,3-Bis(4-hydroxy-3-t,butyl-phenyl)-thiobutansSure~S~butylester 3,3-Bis(4-hydroxy-3-methyl-phenyl)-thiobutansäure-S-octylester 3,3-Bis(4-hydroxy-3-isopropyl-phenyl)-thiobutansäure-S-nonylester 3,3~Bis(4-hydroxy~3-t,butyl-phenyl)-thiobutansSure-S-dodecylester 3,3-Bis(4-hydroxy-3-t.butyl-phenyl)-thiobutansäure-S-phenylester 3,3-Bis (4-hydroxy-phe'nyl )-thiobutansäure-S-benzylester 3,3-Bis(4-hydroxy-3,5-dimethyl-phenyl)-thiobutanssure-S-dodecylphenylester 3,3-Bis(4-hydroxy-3-t.butyl-6-methyl-phenyl)-thiobutansäure S-ß-naphthylester 4,4-Bis(4-hydroxy-3-t.-butyl-phenyl)-thiopentansäure-S-dodecylester 6,6-Bis(4-hydroxy-3-methyl-phenyl)-thioheptansäure-S-isopropyl ester 7,7-Bis(4-hydroxy-phenyl)-thiooctansXure-S-naphthylester Die erfindungsgemäßen Stabilisierungen eignen sich sowohl für Hochdruck- als uch für Niederdruckpolyäthylen, vor allem aber für Polyolefine, die in größerem Maße tertiäre C-Atome enthalten, wie z.B. Polypropylen, Polybuten-(1) und Poly-4-methylpenten-(1). Auch Mischpolymerisate verschiedener DC.-Olefine .untereinander oder mit Äthylen oder geringen Mengen anderer Monomerer lassen sich erfindungs gemäß stabilisieren. Besonders geeignet sind die erfindungsgemäßen Stabilisatoren für Polypropylen.Particularly preferred bisphenol-thioalkanoic acid esters are, for example the following compounds are listed: 3,3-bis (4-hydroxy-3-t, butyl-phenyl) -thiobutane acid ~ S ~ butyl ester 3,3-bis (4-hydroxy-3-methyl-phenyl) -thiobutanoic acid-S-octyl ester 3,3-bis (4-hydroxy-3-isopropyl-phenyl) -thiobutanoic acid-S-nonyl ester 3,3-bis (4-hydroxy-3-t, butyl-phenyl) -thiobutanoic acid-S-dodecyl ester 3,3-bis (4-hydroxy-3-t-butyl-phenyl) -thiobutanoic acid-S-phenyl ester 3,3-bis (4-hydroxy-phe'nyl) -thiobutanoic acid-S-benzyl ester 3,3-bis (4-hydroxy-3,5-dimethyl-phenyl) -thiobutanoic acid-S-dodecylphenyl ester 3,3-bis (4-hydroxy-3-t-butyl-6-methyl-phenyl) -thiobutanoic acid S-ß-naphthyl ester 4,4-bis (4-hydroxy-3-t-butyl-phenyl) -thiopentanoic acid -S-dodecyl ester 6,6-bis (4-hydroxy-3-methyl-phenyl) -thioheptanoic acid-S-isopropyl ester 7,7-bis (4-hydroxyphenyl) -thiooctane-Xure-S-naphthyl ester the Stabilizers according to the invention are suitable for both high pressure and uch Low-pressure polyethylene, but especially for polyolefins, which are to a greater extent tertiary Contain carbon atoms, such as polypropylene, polybutene- (1) and poly-4-methylpentene- (1). Also copolymers of different DC olefins with one another or with ethylene or small amounts of other monomers can be stabilized according to the invention. The stabilizers according to the invention are particularly suitable for polypropylene.
Eine Einmischung der Stabilisatoren in die Polyolefine kann nach üblichen Verfahren erfolgen und läßt sich am besten über ein Konzentrat vornehmen. Die Stabilisatoren können auch während der Herstellung oder Aufarbeitung der Polymerisate eingebracht werden, um das Polymerisat schon während dieser Verfahrensschritte zu schützen.Mixing of the stabilizers into the polyolefins can be carried out according to customary methods Procedure is done and is best done using a concentrate. The stabilizers can also be introduced during the preparation or work-up of the polymers in order to protect the polymer during these process steps.
Die erfindungsgemäßen Formmassen können nach allen bekannten Verformungsverfahren, z B. durch Pressen, Spritzgießen oder Extrusion verarbeitet werden. Ubliche Zusatzstoffe, wie z,B Gleitmittel, Pigmente9 Antistatika, Korrosionsschutzmittel oder weitere Stabilisatoren, wie z.B. Thiodiproyionsäureester, Dialkyldisulfide oder organische Phosphite, vor allem Lichtstabilisatoren, können zugegeben werden. Eine besonders gute Wirksamkeit zeigen die erfindungsgemäßen Stabilisatoren auch zusammen mit Ruß.The molding compositions according to the invention can by all known molding processes, processed e.g. by pressing, injection molding or extrusion. Usual additives, such as lubricants, pigments9, antistatic agents, anti-corrosion agents or others Stabilizers such as thiodiproionic acid esters, dialkyl disulfides or organic Phosphites, especially light stabilizers, can be added. One special The stabilizers according to the invention also show good effectiveness together with carbon black.
Beispiel: Jeweils loo g des zu stabilisierenden Polypropylenpulvers wurden mit einer 5 %igen Methylenchlorid-Lösung der in der Tabelle aufgeführten Stabilisatoren in einem solchen Mengenverhältnis vermischt, daß die auf Polypropylen berechnete Stabilisatorkonzentration die fünffache Menge der in der Tabelle angegebenen Stabilisatorkonzentration betrug. Nach dem Trocknen bei 80°C im Vakuum wurde das stabilisierte Polypropylenpulver (Konzentrat) mit 400 g unstabilisiertem Polypropylen intensiv vermischt und die Mischung anschließend in einem Laborextruder bei 200t granuliert.Example: In each case 100 g of the polypropylene powder to be stabilized were with a 5% methylene chloride solution of those listed in the table Stabilizers mixed in such a proportion that those based on polypropylene The calculated stabilizer concentration is five times the amount given in the table Stabilizer concentration was. To drying at 80 ° C in The stabilized polypropylene powder (concentrate) with 400 g of unstabilized powder was vacuumed Polypropylene mixed intensively and then the mixture in a laboratory extruder granulated at 200t.
Diese Granulatproben wurden. bei 22o0C zu o,2 mm dicken Folien verpreßt.These granulate samples were. pressed at 22o0C to form 0.2 mm thick foils.
Außer den angegebenen Stabilisatoren enthielten alle Proben o,2 Gew.-% Calciumstearat als Korrosionsschutzmittel.Except for the specified stabilizers, all samples contained 0.2% by weight Calcium stearate as a corrosion protection agent.
Aus den Folien wurden mehrere Prüfstreifen von jeweils lo mm Breite und loo mm Länge ausgestanzt, zur Bestimmung der Wärmealterungsbeständigkeit in einem Umlufttrockenschrank bei 140°C frei aufgehängt und die Zeit in Tagen bestimmt, nach welcher die Prüfstreifen beim Biegen um 1800' brachen bzw. den Beginn eines pulverförmigen Zerfalls zeigten.Several test strips, each lo mm wide, were made from the films and loo mm length punched out to determine the heat aging resistance in freely hung in a circulating air drying cabinet at 140 ° C and the time is determined in days, after which the test strips broke when bent by 1800 'or the beginning of a showed powdery disintegration.
Zur Bestimmung der Extraktionsbeständigkeit wurden die gleichen Prüfstreifen verschiedene Zeiten in einem bei 980C gehaltenen Wasserdurchlauferhitzer gelagert.The same test strips were used to determine the resistance to extraction stored for various times in a water heater kept at 980C.
Nach den in der Tabelle angegebenen Lager- bzw. Extraktionszeiten wurden die auf diese Weise vorbehandelten Prüfstreifen bei 140°C im Umlufttrockenschrank -einer beschleunigten Alterung unterworfen In den Beispielen ist die Wärmealterungsbeständigkeit der Folien bei 1400C nach verschiedenen Extraktionszeiten angegeben.After the storage or extraction times specified in the table the test strips pretreated in this way were made at 140 ° C. in a circulating air drying cabinet - subjected to accelerated aging In the examples, the heat aging resistance is of the foils indicated at 1400C after various extraction times.
Aus den Werten geht hervor, daß die erfindungsgemäßen Bisphenolthioalkansäureester bei gleicher Stabilisatorgesamtkonzentration eine wesentlich bessere Extraktionsresistenz besitzen, als vergleichbare synergistische Mischungen zwischen entsprechenden schwefelfreien phenolischen Antioxydantien und Dilaurylthiodipropionat.The values show that the bisphenolthioalkanoic acid esters according to the invention with the same total stabilizer concentration, a significantly better extraction resistance possess than comparable synergistic mixtures between corresponding sulfur-free phenolic antioxidants and dilauryl thiodipropionate.
Die Verwendung der erfindungsgemäßen Bisphenolthioalkansäu reester bietet somit besondere Vorteile, wenn mit Extraktion gerechnet werden muß,The use of the bisphenolthioalkanic acid esters according to the invention thus offers particular advantages if extraction is to be expected,
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702017963 DE2017963A1 (en) | 1970-04-15 | 1970-04-15 | Polyolefin blend stabilised with bisphenol-t |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702017963 DE2017963A1 (en) | 1970-04-15 | 1970-04-15 | Polyolefin blend stabilised with bisphenol-t |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2017963A1 true DE2017963A1 (en) | 1971-10-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702017963 Pending DE2017963A1 (en) | 1970-04-15 | 1970-04-15 | Polyolefin blend stabilised with bisphenol-t |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2017963A1 (en) |
-
1970
- 1970-04-15 DE DE19702017963 patent/DE2017963A1/en active Pending
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