DE1286041B - Stabilisieren von Polyolefinen und Mineraloelen - Google Patents
Stabilisieren von Polyolefinen und MineraloelenInfo
- Publication number
- DE1286041B DE1286041B DEG40475A DEG0040475A DE1286041B DE 1286041 B DE1286041 B DE 1286041B DE G40475 A DEG40475 A DE G40475A DE G0040475 A DEG0040475 A DE G0040475A DE 1286041 B DE1286041 B DE 1286041B
- Authority
- DE
- Germany
- Prior art keywords
- pressure
- mineral oil
- carbon atoms
- coor
- weight
- 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
- 239000002480 mineral oil Substances 0.000 title claims description 11
- 230000000087 stabilizing effect Effects 0.000 title claims description 5
- 229920000098 polyolefin Polymers 0.000 title claims description 4
- -1 (methylene-3 ', 5' - di - tert - butyl - 4 '- hydroxybenzoate) ethanol Chemical compound 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 235000010446 mineral oil Nutrition 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000004743 Polypropylene Substances 0.000 description 10
- 229920001155 polypropylene Polymers 0.000 description 10
- 230000006641 stabilisation Effects 0.000 description 10
- 238000011105 stabilization Methods 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000006864 oxidative decomposition reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000008139 complexing agent Substances 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 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 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000755 henicosyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])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])[H] 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([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])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])[H] 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
- C09K15/14—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen containing a phenol or quinone moiety
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/24—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing a phenol or quinone moiety
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/284—Esters of aromatic monocarboxylic acids
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/285—Esters of aromatic polycarboxylic acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
-
- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/30—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Description
Gegenstand der vorliegenden Erfindung ist die Verwendung von Estern der allgemeinen Formel I
bis V:
COOCH7 —
CH2CH2COOCH2Ch2 —
oder eine Alkanamidogruppe der Formel
>N —CO—R
worin R eine Alkylgruppe, insbesondere mit 1 bis 23 Kohlenstoffatomen bedeutet; B den zweiwertigen
Rest des Glykols oder Glyzerins wie
— CH, — CH — R
CHoCOO-
^C-CH2OH
(H)
(III)
(IV)
C = CH-COOR4
R CH-CH-COOR4
worin A einen N-niederen Alkylrest, einen 1,4-Piperazinylrest
oder eine Alkanamidogruppe mit 2 bis 24 Kohlenstoffatomen, B den zweiwertigen Rest eines
Alkohols mit zwei oder drei Hydroxygruppen, R1 und R2 unabhängig voneinander je eine Alkylgruppe
mit 4 bis 8 Kohlenstoffatomen und R3, R4 und R5
unabhängig voneinander je einen Alkylrest mit 1 bis 24 Kohlenstoffatomen bedeuten, in Mengen
von vorzugsweise 0,05 bis 10 Gewichtsprozent zum Stabilisieren von Polyolefinen und Mineralölen gegen
Zersetzung durch Sauerstoff und/oder Hitze. In den Formeln I bis V bedeuten beispielsweise A
N-CH3
N-C4H9
N-C4H9
^N-C2H5
^N-C5H11
N-CH2CH2OOCCH2Ch2
oder eine 1,4-Piperazinylgruppe der Formel
^C^iT^C^r^
-N
N —
wobei R entweder Wasserstoff oder — CH3 oder
— CH2OR' bedeutet und R' wiederum Wasserstoff oder eine Acylgruppe, wie Acetyl, Lauroyl oder
Stearoyl, ist, und R1 und R2 unabhängig voneinander
vorzugsweise eine tertiäre Alkylgruppe mit 4 bis 8 Kohlenstoffatomen, sowie R3, R4 und R5 unabhängig
voneinander Methyl, Äthyl, Propyl, Butyl, Pentyl, Hexyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl,
Dodecyl, Tridecyl, Tetradecyl, Pentadecyl, Hexadecyl, Heptadecyl, Octadecyl, Nonadecyl, Eikosyl, Heneikosyl,
Trikosyl, Tetrakosyl.
Als erfindungsgemäß stabilisierbare Stoffe kommen in Betracht: Polyolefine, besonders Kunstharze, wie
Polystyrol, Polybutylen, Polyäthylen und insbesondere Polypropylen und Mineralöle, wie mineralische
Schmieröle und Benzin.
Verbindungen der Formeln IV und V sind bevorzugt für die Stabilisierung von Polypropylen
geeignet.
Die erfindungsgemäß verwendbaren Stabilisatoren 30 werden üblicherweise in Mengen von etwa 0,005
bis 10%. berechnet auf das Gesamtgewicht der stabilisierten
Stoffzusammenstellung, eingesetzt. Für die (V) Stabilisierung von Polypropylen sind Mengen von
0,05 bis 5 Gewichtsprozent angezeigt, vorzugsweise Mengen von 0,1 bis 1 Gewichtsprozent. Zur Stabilisierung
von Mineralölen erweisen sich Mengen von 0,05 bis 5 Gewichtsprozent als günstig. Die genannten
Gewichtsprozente beziehen sich alle auf die stabilisierte Stoffzusammenstellung.
Die erfindungsgemäß verwendbaren Stabilisatoren können allein oder in Kombination mit anderen
stabilisierenden Stoffen und üblichen Zusätzen verwendet werden. In manchen Fällen ist das Di-lauryl-/S-thio-dipropionat
ein günstiges zusätzliches Stabilisierungsmittel. Ebenso können die erfindungsgemäß
verwendbaren Stabilisatoren zusammen mit Ultraviolettabsorptionsmitteln,
Farbstoffen, Pigmenten, Metallkomplexbildnern usw. verwendet werden.
In dieser Erfindung bedeutet »Stabilisierung« nicht nur Schützen gegen oxydative Zersetzung, sondern
auch gegen thermische Einflüsse.
Die folgenden Beispiele sollen die Erfindung veranschaulichen. Sofern in den Beispielen nichts anderes
vermerkt ist, sind Teile als Gewichtsteile zu verstehen. 55
Stabilisieren von Polypropylen
Nicht stabilisiertes Polypropylenpulver (Hercules PROFAX 6501) wird mit 0,5 Gewichtsprozent
2-n-Octadecylthio-3-(3',5'-di-tert.-butyl-4'-hydroxyphenyl)-bernsteinsäuredimethylester
(Fp. 86 bis 880C) innig vermischt. Das Gemisch wird 5 Minuten bei
182° C auf einem Zweiwalzenstuhl gemahlen und e5 dann zu einer Folie ausgezogen und erkalten gelassen.
Die so erhaltene Polypropylenfolie ist gegen Zersetzung weitgehend stabil, wie aus dem folgenden .
Alterungstest hervorgeht:
OH
Die stabilisierte Polypropylenfolie wird in schmale Stücke geschnitten und 7 Minuten bei 218° C in
einer hydraulischen Presse gepreßt. Die resultierende Folie von 0,6 mm Dicke wird dann in einem Luftumwälzungsofen
bei 149° C auf ihre Beständigkeit gegen beschleunigte Alterung geprüft.
Das mit 0,5 Gewichtsprozent 2-n-Octadecylthio-3-(3',5'-ditert.
- butyl - 4' - hydroxyphenyl) - bernsteinsäuredimethylester stabilisierte Polypropylen zeigt
nach 500 Stunden noch keine oxydative Zersetzung, während das nicht stabilisierte Polypropylen schon
nach 3 Stunden stark verändert ist.
Wenn man in diesem Beispiel ein mit 0,5 Gewichtsprozent einer der nachfolgend genannten Verbindungen
stabilisiertes Polypropylen verwendet, erhält man folgende Ergebnisse:
2 - (3',5' - Di - tert. - butyl - 4' - hydroxyphenyl) - buten
- (2) - disäuredimethylester, Doppelschmelzpunkt 117°C und 142 bis 1430C; Stabilisierungsdauer:
635 Stunden.
2,2,2-Tris-(methylen-3',5'-di-tert.-butyl-4'-hydroxybenzoat)-äthanol,
Fp. 145° C; Stabilisierungsdauer: 723 Stunden.
N,N'-Bis-[äthylen-3-(3',5'-di-tert.-butyl-4'-hydroxyphenyl)
- propionat] - piperazin, Fp. 135 bis 136°C; Stabilisierungsdauer: 975 Stunden.
Ν,Ν,Ν - Tris - [äthylen - 3 - (3',5' - di - tert. - butyl-4'
- hydroxyphenyl) - propionat] - amin, Fp. 110 bis 111°C; Stabilisierungsdauer: 1265 Stunden.
N,N-Bis-[äthylen-3-(3',5'-di-tert.-butyl-4'-hydrozyphenyl)-propionat]-N-n-butylamin,
Sirup, Hydrochlorid, Fp. 255 bis 257° C; Stabilisierungsdauer: 1150 Stunden.
Glyzerin -1 - η - octadecanoat - 2,3 - bis - (3',5' - ditert.
- butyl - 4' - hydroxyphenylacetat), Fp. 84,4 bis 85,5°C; Stabilisierungsdauer: 700 Stunden.
N,N-bis-[äthylen-3-(3',5'-di-tert.-butyl-4'-hydroxyphenyl) - propionat] - stearoylamin, Sirup,
Stickstoff: berechnet 1,57, gefunden 1,58, Kernresonanz: Verhältnis CH2/CH3, berechnet 1,23,
gefunden 1,25; Stabilisierungsdauer: 575 Stunden.
während nicht stabilisiertes Mineralöl schon nach 1,7 Stunden den gleichen Druckabfall zeigt.
In gleicher Weise wird eine stabilisierte Stoffzusammenstellung aus Mineralöl und 0,1 Gewichtsprozent
Glyzerin-l-n-octadecanoat-2,3-bis-(3',5'-ditert. - butyl - 4' - hydroxyphenylacetat) getestet. Der
Druckabfall von 300 mm Hg wird nach 33 Stunden erreicht.
Claims (1)
- Patentanspruch:Verwendung von Estern der allgemeinen Formeln I bis V:Beispiel 2
Stabilisieren von Mineralöl45Wasserklares, raffiniertes Mineralöl (Esso PRI-MOL D) wird unter folgender Bedingung stabilisiert: 10 g Mineralöl werden in einen bei Raumtemperatur (25° C) und bei Normaldruck mit Sauerstoff gefüllten Oxydationskolben gegeben. Der Kolben wird verschlossen und mit einem Quecksilber-Manometer verbunden, welches die durch Absorption im Kolben entstandenen Druckveränderungen anzeigt. Der Apparat wird dann auf 1500C erhitzt und so lange bei dieser Temperatur gehalten, bis das Manometer einen Druckverlust von 300 mm Hg, verglichen mit dem Druck bei 150° C, anzeigt. Bei stabilisiertem Mineralöl, das. 0,1 Gewichtsprozent 2,2,2 - Tris - (methylen-3',5' - di - tert. - butyl - 4' - hydroxybenzoat) - äthanol enthält, tritt der Druckverlust nach 38 Stunden ein, HO£ CH2CH2COOCH2Ch2-£ COOCH2HO —' CH2COO-κ.^C-CH5OHHOHOCOOR,R C = CH — COOR4COOR,C-OR5worin A einen N-niederen Alkylrest, einen 1,4-Piperazinylrest oder eine Alkanamidogruppe mit 2 bis 24 Kohlenstoffatomen, B den zweiwertigen Rest eines Alkohols mit zwei oder drei Hydroxygruppen, R1 und R2 unabhängig voneinander je eine Alkylgruppe mit 4 bis 8 Kohlenstoffatomen und R3, R4 und R5 unabhängig voneinander je einen Alkylrest mit 1 bis 24 Kohlenstoffatomen bedeuten, in Mengen von vorzugsweise 0,05 bis 10 Gewichtsprozent zum Stabilisieren von Polyolefinen und Mineralölen gegen Zersetzung durch Sauerstoff und/oder Hitze.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27619263A | 1963-04-29 | 1963-04-29 | |
| US413996A US3277152A (en) | 1963-04-29 | 1964-11-25 | Dialkyl 2-(dialkylhydroxyphenyl)-2-butendioates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1286041B true DE1286041B (de) | 1969-01-02 |
Family
ID=26957838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG40475A Pending DE1286041B (de) | 1963-04-29 | 1964-04-28 | Stabilisieren von Polyolefinen und Mineraloelen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3277152A (de) |
| BE (1) | BE647219A (de) |
| CH (1) | CH482773A (de) |
| DE (1) | DE1286041B (de) |
| GB (1) | GB1001098A (de) |
| NL (1) | NL141563B (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3988363A (en) * | 1973-09-25 | 1976-10-26 | Ciba-Geigy Corporation | 2,4,6-Trialkyl L-3-hydroxyphenylalkanoates |
| US4075161A (en) | 1973-09-25 | 1978-02-21 | Ciba-Geigy Corporation | Esters and amides of 2,4,6-trialkyl-3-hydroxy-phenylalkanoic acids |
| US4113442A (en) * | 1974-10-03 | 1978-09-12 | Shell Oil Company | Middle distillate fuel compositions |
| US4085132A (en) * | 1975-06-24 | 1978-04-18 | Ciba-Geigy Corporation | Process for the production of hydroxyalkylphenyl derivatives |
| EP0273011B1 (de) * | 1986-12-24 | 1993-03-17 | Ciba-Geigy Ag | N,N-bis(hydroxyäthyl)hydroxylaminester-Stabilisatoren |
| US5023283A (en) * | 1986-12-24 | 1991-06-11 | Ciba-Geigy Corporation | N,N-bis(acyloxyethyl)hydroxylamine derivatives |
| BE1014162A3 (fr) * | 1997-05-26 | 2003-06-03 | Ciba Sc Holding Ag | Produits stabilisants, compositions et concentres les contenant, et leur procede d'utilisation. |
| WO2019152777A2 (en) | 2018-02-02 | 2019-08-08 | The Regents Of The University Of California | Non-migratory internal plasticizers attached to a pendant covalent linkage |
| CN108752203A (zh) * | 2018-05-16 | 2018-11-06 | 西南交通大学 | 一种受阻酚抗氧化剂的制备方法 |
| CN108929237A (zh) * | 2018-06-25 | 2018-12-04 | 山东省临沂市三丰化工有限公司 | 一种新型液体抗氧剂及其制备方法 |
| CN119118853A (zh) * | 2024-09-09 | 2024-12-13 | 东莞市优骏橡塑制品有限公司 | 一种聚氨酯固化剂及其在制备弹性体中的应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE624206A (de) * | 1961-10-30 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2293309A (en) * | 1941-03-06 | 1942-08-18 | American Cyanamid Co | Malonic esters as insecticides |
-
1964
- 1964-04-27 CH CH547064A patent/CH482773A/de not_active IP Right Cessation
- 1964-04-28 BE BE647219A patent/BE647219A/xx unknown
- 1964-04-28 NL NL646404697A patent/NL141563B/xx not_active IP Right Cessation
- 1964-04-28 DE DEG40475A patent/DE1286041B/de active Pending
- 1964-04-28 GB GB17547/64A patent/GB1001098A/en not_active Expired
- 1964-11-25 US US413996A patent/US3277152A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE624206A (de) * | 1961-10-30 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL141563B (nl) | 1974-03-15 |
| GB1001098A (en) | 1965-08-11 |
| CH482773A (de) | 1969-12-15 |
| NL6404697A (de) | 1964-10-30 |
| BE647219A (de) | 1964-10-28 |
| US3277152A (en) | 1966-10-04 |
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