Efficient phosphorus-containing stabilizers based on diphenylamine and heterocyclic diphenylamine derivatives

Abstract

The present invention relates to the use of effective phosphoric substances, particularly those based on diphenylamine and heterocyclic diphenylamine derivatives, as stabilizers of organic materials, especially plastics, against oxidative, thermal, and / or actinic degradation. The present invention also relates to an organic material stabilized in the manner described above. Furthermore, the invention relates to a method for stabilizing organic materials and specific stabilizers.

Description

[0001] The present invention relates to the use of efficient phosphorus-containing substances, particularly those based on diphenylamine and heterocyclic diphenylamine derivatives, as stabilizers for organic materials, especially plastic materials, against oxidative, thermal, and / or actinic degradation. The present invention also relates to an organic material stabilized as described above. Furthermore, the invention relates to a method for stabilizing organic materials and to specific stabilizers.

[0002] Plastics and plastic-based compositions such as coatings are subject to autoxidation during processing and use.

[0003] Starting from radical chain splitting through mechanochemical processes or through UV radiation in the presence of oxygen, this leads to changes in the polymer chain, such as in molecular weight or the formation of new chemical groups.

[0004] The breakdown or chemical alteration of polymer molecules degrades the mechanical properties of plastics and leads to discoloration (yellowing) or other undesirable effects. Thermal degradation limits the maximum operating temperature of plastics, and aging processes restrict the potential service life of plastic objects, which is shortened with increasing temperature.

[0005] Therefore, the addition of special stabilizers such as antioxidants and light stabilizers is necessary, which delay the degradation processes and thus have a significant influence on the processability and the range of applications of plastics.

[0006] There is currently a great deal of interest in more efficient stabilizers and stabilizer systems, partly because plastics are increasingly used in applications where they are exposed to increased thermal and mechanical stresses (e-mobility, lightweight construction, high-performance batteries, etc.). Another reason for the search for new stabilizers is that many currently used substances do not meet all requirements, for example, regarding their compatibility with the polymers to be protected, low migration, or the formation of undesirable degradation products.

[0007] There are various types of stabilizers, of which the following are important: Processing stabilizers slow down degradation processes that occur at high processing temperatures. Long-term thermal stabilizers are used to delay aging, especially at elevated temperatures. High-temperature stabilizers counteract degradation when plastics are exposed to high temperatures (180°C and above). UV stabilizers delay or prevent degradation processes initiated by UV light.

[0008] The various stabilizers are often used in (synergistic) combinations. The function of stabilizers includes, among other things, neutralizing free radicals and deactivating peroxides and hydroperoxides formed upon exposure to oxygen, as these can damage the polymer chain. The effectiveness of stabilizers and antioxidants is crucial for both the processability of the plastics and the lifespan of the objects made from them. They also influence the maximum operating temperature of the plastics and their potential service life at elevated temperatures.

[0009] Numerous chemical compounds are available on the market as stabilizers / antioxidants. The most important classes of antioxidants are sterically hindered phenols, phosphites or phosphonites, amines, thio compounds, hydroxylamines, and lactones. Sterically hindered amines, so-called HALS compounds, are particularly noteworthy as light stabilizers that also function as long-term heat stabilizers. Benzotriazoles, benzophenones, hydroxyphenyltriazines, and others are also frequently used as UV absorbers.

[0010] The particular importance of phosphite stabilizers stems from their ability to deactivate peroxides and hydroperoxides. However, the substances used so far have disadvantages, including limitations in thermostability, long-term effectiveness, hydrolysis resistance, and compatibility. Therefore, intensive research is underway to find new, improved stabilizers that offer advantages such as: Increased hydrolysis resistance and improved thermal properties; suitable for use at particularly high temperatures; particularly high and long-lasting efficiency; no undesirable side effects (discoloration, etc.).

[0011] For elastomers, diphenylamine derivatives are used as environmentally friendly, low-toxicity stabilizers. The structurally similar heterocyclic compound phenothiazine also possesses a high capacity to deactivate radicals and is only slightly toxic. It is used for the storage stabilization of acrylates, methacrylates, and other monomers, where it prevents the spontaneous polymerization of radicals by scavenging them, thus acting similarly to plastic stabilizers. Furthermore, phenothiazine is an effective antioxidant for lubricants. A patent from 1961 (GB 4331, "Phenothiazine stabilizers for polyethylene") describes the use of phenothiazine as a stabilizer for polyethylene.Despite its proven stabilizing effect on thermoplastic polymers and elastomers, phenothiazine has the disadvantage of high volatility under normal processing conditions and therefore has no commercial significance as a plastic stabilizer.

[0012] To date, very few phosphorus-containing phenothiazine derivatives have been described or listed in patents. Phenothiazine derivatives bearing phosphorus substituents on the nitrogen atom are mentioned in the following patents: WO2015158692A1 (2016), WO2015158689A1 (2016), CN 101531578A (2009).

[0013] The patent JP2006328100A (Songwon Industrial Co. LTD, 2006) mentions the following compound as a flame retardant for plastics:

[0014] However, until now nothing was known regarding the antioxidant stabilization effect of this compound and other phosphorus-containing derivatives of phenothiazine.

[0015] Numerous phosphorus-containing derivatives of the structurally related carbazole have been described, and various applications of such substances are listed in patent literature, but not as a stabilizer for plastics.

[0016] There is no information available regarding the use or testing of phosphorus-containing diphenylamine derivatives, which have at least one carbon atom attached to the phosphorus atom, as stabilizers for plastics.

[0017] MM Cous et al. describe in Journal of Economic Entomology, 1956, 49, 6, 747-750 the use of various phosphorus-containing compounds as ovicides.

[0018] AA Yehia et al. describe the synthesis of aminophosphine derivatives such as tri(diphenylamino)phosphine and tri(di-cymyl-diphenylamino)phosphine in Polymer-Plastics Technology and Engineering, 2002, 41, 2, 199-213. These compounds were incorporated into natural rubber (NR) and styrene-butadiene rubber (SBR) mixtures. The rheometric properties of the green rubber mixtures were determined using an oscillating disk rheometer. The synthesized compounds were evaluated as fatigue-inhibiting and antioxidant agents in NR and SBR vulcanizates. The results showed that the investigated compounds are good antioxidants and fatigue-inhibiting agents, and their efficacy is superior to that of phenyl β-naphthylamine, which is widely used in the rubber industry.

[0019] CN 102 237 551 A provides a non-aqueous electrolyte, a manufacturing process for it, and a battery that uses the non-aqueous electrolyte. The electrolyte contains a lithium salt, an organic solvent, and an additive.

[0020] US 4,664,594 A describes effective processing stabilizers for polymers, especially for polyolefins, which also have a stabilizing effect against light damage.

[0021] US 5,230,816 A refers to new 3,9-bis(dialkylamino-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane compounds and stabilized compositions containing these compounds.

[0022] CN 104 212 439 A relates to a photoelectric functional material with an NP=S resonant structure, a manufacturing process, and an application. This photoelectric functional material, which possesses the NP=S resonant structure, dynamically adjustable electrical power, a high triplet state energy level, and bipolar transfer properties, offers the advantages of inexpensive raw materials, a simple and convenient synthesis process, and good solubility, film formability, and stability. The introduction of the NP=S resonant structure significantly improves the material's carrier transfer capability and provides excellent cavity and electron transfer capabilities. Electroluminescent devices manufactured from this material exhibit high efficiency, a relatively low turn-on voltage, and stable electroluminescence performance.The technical scheme is of important importance for the development of efficient, stable organic light-emitting diodes.

[0023] CN 105 859 778 A discloses a pure organic phosphorescent material with afterglow and an ultra-long lifetime, a process for producing the pure organic phosphorescent material, and its application. The pure organic phosphorescent material comprises phenylphosphorus and carbazole structures and is DNCzPS or DNCzPSe. The process includes carrying out a reaction on carbazole and dichlorophenylphosphine at low temperatures to obtain dicarbazolylphenylphosphorus, which is an intermediate; carrying out a vulcanization or selenylation reaction on the intermediate to obtain the corresponding products DNCzPS and DNCzPSe.

[0024] DE 24 17 991 A describes thiophosphoric acid amides, processes for their production and their application.

[0025] From DD 146 646, a process for stabilizing organic polymers against thermo-oxidative degradation using phosphoric acid esteramides is known. The sterically hindered phosphoric acid esteramides according to the invention exhibit good color and hydrolysis stability and are effective at both lower (< 100 °C) and higher (> 150 °C) temperatures.

[0026] The object of the present invention was to develop new effective stabilizers for plastics and plastic-based applications.

[0027] This problem is solved with regard to the use of specific materials as stabilizers with the features of claim 1, with regard to a specifically stabilized plastic composition with the features of claim 12, and with regard to a method for stabilizing organic materials with the features of claim 13. The respective dependent claims represent advantageous further developments.

[0028] The present invention thus relates to the use of a compound or mixtures of several compounds according to general formula I AB y formula I wherein fragment A has the following meaning wherein X is a sulfur atom, n0 or 1, x0 or 1, Z1< and Z2< are selected independently from the group consisting of hydrogen, alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, heterocyclic groups, wherein one or more further fragments A and / or B may be bonded to the aforementioned groups, and a grouping -OZ3<, wherein Z3< is selected from alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, and heterocyclic groups, and a grouping -SZ4<, wherein Z4< is selected from alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, and heterocyclic groups, wherein in the case of x = 1 the groups Z1< and Z2< together with the phosphorus atom may form a ring system to which one or more further fragments A and / or B may be bonded. fragment B has the following meaning wherein R 1< to R 10< are each independently selected from the group consisting of hydrogen, alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups and heterocyclic groups, wherein (in the case y = 1 or 2), preferably in the case y = 1, the groups R 1< and R 6< may also be connected via a grouping -Y- connecting the phenyl groups, wherein Y is selected from the group consisting of S, O, NH, PH and a covalent bond, wherein the fragments A and B are connected to each other by covalent bonding of the phosphorus and nitrogen atoms, and wherein y is 1 or 2, where x + y = 2, for stabilizing organic materials, in particular against oxidative, thermal and / or actinic degradation.

[0029] The compound according to general formula I can exist as a separate molecule, but also on a polymeric framework, be it within the

[0030] The main chain, whether it is bound in a secondary chain.

[0031] Preferably, Z 1< and Z 2< are selected from the group consisting of hydrogen, alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, heterocyclic groups, wherein one or more further fragments A and / or B may be bonded to the aforementioned groups. as well as a grouping -OZ 3< , wherein Z 3< is selected from alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, and heterocyclic groups, wherein in the case x = 1 the groups Z 1< and Z 2< together with the phosphorus atom can form a ring system to which one or more further fragments A and / or B can be bonded.

[0032] Surprisingly, it was found that the compounds according to the general formula I as defined above have a particularly good efficiency as stabilizers of organic materials, so that their use leads to high stabilization rates even at relatively low concentrations.

[0033] In particular, the compounds described above are suitable for stabilizing plastics, coatings, lubricants, hydraulic oils, chemicals, and monomers.

[0034] According to the invention, in the compounds described above according to formula I, it is provided that fragment A is selected from the following residues. where x = y = 1 where x = 0 and y = 2, or where x = y = 1 where x = y = 1, each independent of the other R 11< is selected from the group consisting of hydrogen, alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups and heterocyclic groups, R 12< is selected from the group consisting of hydrogen, alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups, heterocyclic groups, wherein the aforementioned groups may also have heteroatoms and / or one or more further fragments A and / or B may be bonded to the aforementioned groups, and X and n are as defined above.

[0035] Fragment A, selected from the following remains, is particularly preferred. where x = y = 1 in each case, where x = 0 and y = 2 in each case, and where x = y = 1 in each case.

[0036] With regard to fragment B, it is advantageous if it is selected from the group consisting of the following residues. where y = 1 or 2, where y = 1 or 2, as well as where y = 1 or 2, where R 2< to R 5< and R 7< to R 10< and Y are defined independently of each other as in claim 1.

[0037] It is particularly advantageous if fragment B is selected from the group consisting of the following residues.

[0038] Particularly preferred compounds that can be used as stabilizers for the purposes of the present invention are listed below: wherein R 11< is selected independently of each other from the group consisting of hydrogen, alkyl groups, aryl groups, alkylaryl groups, arylalkyl groups and heterocyclic groups.

[0039] The compound according to general formula I, or in the case of a mixture of several compounds according to general formula I, the entirety of all compounds according to general formula I, are preferably added (incorporated) and / or incorporated by mixing into the organic material, i.e., the material that is subject to oxidative, thermal, and / or actinic degradation, at a weight fraction of 0.01 to 10 wt.%, more preferably 0.05 to 5 wt.%, and particularly preferably 0.1 to 1.5 wt.%. Particularly in the case of plastic compositions, this can be achieved, for example, during thermal processing by melting, such as by kneading or extrusion of these materials. In the case of liquid materials, such as oils, the compounds according to general formula I are incorporated by dissolving or dispersing the materials in the liquid.

[0040] In the event that the compound according to general formula I is used for stabilizing plastic materials, it is preferred if the plastic is selected from the group consisting of a) Polymers made from olefins or diolefins such as polyethylene (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methylpentene-1, polybutadiene, polyisoprene, such as natural rubber (NR), polycyclooctene, polyalkylene-carbon monoxide copolymers, as well as copolymers in the form of statistical or block structures such as polypropylene-polyethylene (EP), EPM or EPDM with, for example, 5-ethylidene-2-norbornene as a comonomer, ethylene vinyl acetate (EVA), ethylene acrylates such as ethylene butyl acrylate, ethylene acrylic acid and their salts (ionomers), as well as terpolymers such as ethylene acrylic acid glycidyl (meth)acrylate, graft polymers such as polypropylene graft maleic anhydride, Polypropylene graft-acrylic acid, polyethylene graft-acrylic acid, polyethylene-polybutylacrylate graft-maleic anhydride, and blends such as LDPE / LLDPE or long-chain branched polypropylene copolymers produced with alpha-olefins as comonomers, such as...with 1-butene, 1-hexene, 1-octene or 1-octadecene b) Polystyrene, polymethylstyrene, poly-alpha-methylstyrene, polyvinylnaphthalene, polyvinylbiphenyl, polyvinyltoluene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene-propylene-styrene, styrene-isoprene, styrene-isoprene-styrene (SIS), styrene-butadiene-acrylonitrile (ABS), styrene-acrylonitrile (SAN), styrene-acrylonitrile acrylate (ASA), styrene-ethylene, styrene-maleic anhydride polymers including corresponding graft copolymers such as styrene on butadiene, maleic anhydride on SBS or SEBS, as well as Graft copolymers of methyl methacrylate, styrene-butadiene and ABS (MABS), as well as hydrogenated polystyrene derivatives such as polyvinylcyclohexane c) halogen-containing polymers such asPolyvinyl chloride (PVC), polychloroprene and polyvinylidene chloride (PVDC), copolymers of vinyl chloride and vinylidene chloride or of vinyl chloride and vinyl acetate, chlorinated polyethylene, polyvinylidene fluoride, epichlorohydrin homo and copolymers, especially with ethylene oxide (ECO); d) polymers of unsaturated esters such as polyacrylates and polymethacrylates such as polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyglycidyl acrylate, polyglycidyl methacrylate, polyacrylonitrile, polyacrylamides, copolymers such as polyacrylonitrile-polyalkyl acrylate; e) polymers of unsaturated alcohols and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine; f) polyacetals, such as polyoxymethylene (POM) or copolymers with, for example, butanal; g) polyphenylene oxides and blends with polystyrene or polyamides, h) polymers of cyclic ethers such as e.g.Polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran, i) polyurethanes, made from hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates such as 2,4- or 2,6-toluene diisocyanate or methylenediphenyl diisocyanate, in particular also linear polyurethanes (TPU), polyureas, j) polyamides such as polyamide-6, 6.6, 6.10, 4.6, 4.10, 6.12, 10.10, 10.12, 12.12, polyamide 11, polyamide 12 and (partially) aromatic polyamides such as polyphthalamides, e.g. made from terephthalic acid and / or isophthalic acid and aliphatic diamines such as hexamethylenediamine or m-xylylenediamine or from aliphatic dicarboxylic acids such as adipic acid or sebacic acid and aromatic diamines such as 1,4- or 1,3-Diaminobenzene, blends of different polyamides such as PA-6 and PA 6.6, or blends of polyamides and polyolefins such as...PA / PP k) Polyimides, polyamide-imides, polyetherimides, polyesterimides, poly(ether)ketones, polysulfones, polyethersulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins, l) Polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTT), polyethylene naphthylate (PEN), poly-1,4-dimethylolcyclohexane terephthalate, polyhydroxybenzoate, polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polyethylene succinate, polytetramethylene succinate, polycaprolactone m) Polycarbonates, polyester carbonates, and blends such as PC / ABS, PC / PBT, PC / PET / PBT, PC / PA n) Cellulose derivatives such as cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate, o) Epoxy resins consisting of di- or polyfunctional epoxy compounds in combination with e.g.Hardeners based on amines, anhydrides, dicyandiamide, mercaptans, isocyanates or catalytically acting hardeners, p) phenolic resins such as phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins, q) unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds, e.g., styrene, alkyd resins, r) silicones, e.g., based on dimethylsiloxanes, methylphenylsiloxanes or diphenylsiloxanes, e.g., vinyl-terminated groups, s) as well as mixtures, combinations or blends of two or more of the aforementioned polymers.

[0041] If the polymers listed under a) to r) are copolymers, they can exist in the form of random, block, or tapered structures. Furthermore, the polymers mentioned can exist in the form of linear, branched, star-shaped, or hyperbranched structures.

[0042] If the polymers listed under a) to r) are stereoregular polymers, they can be in the form of isotactic, stereotactic, but also atactic forms or as stereoblock copolymers.

[0043] Furthermore, the polymers listed under a) to r) can exhibit both amorphous and (partially) crystalline morphologies.

[0044] The polyolefins mentioned under a) may also be cross-linked, e.g. cross-linked polyethylene, which is then referred to as X-PE.

[0045] The polymers mentioned a) to r) can be present not only as new products but also in the form of recyclates, e.g. as production waste or from recycling ("post-consumer" recyclates).

[0046] For the conceptual definition of Plastic recyclatesIn a further preferred embodiment, these are recycled plastics or recycled plastics. For the conceptual definition, reference is made to the standard DIN EN 15347:2007, which defines the term "recycled plastic". This definition is also used as the basis for the present invention.

[0047] Particularly preferred is the recycled plastic selected from the group consisting of recycled polyesters, in particular recycled polyethylene terephthalate (rPET), recycled polybutylene terephthalate (rPBT), recycled polylactic acid (rPLA), recycled polyglycolide and / or recycled polycaprolactone; recycled polyolefins, in particular recycled polypropylene (rPP), recycled polyethylene and / or recycled polystyrene (rPS); recycled polyvinyl chloride (rPVC), recycled polyamides and mixtures and combinations thereof.

[0048] Relevant international standards exist for many recycled plastics. For example, DIN EN 15353:2007 applies to recycled PET plastics. Recycled PS is described in more detail in DIN EN 15342:2008. Recycled PE is addressed in DIN EN 15344:2008. Recycled PP is characterized in DIN EN 15345:2008. Recycled PVC is further specified in DIN EN 15346:2015. For the purposes of the respective specific recycled plastics, the present patent application adopts the definitions of these international standards.

[0049] Furthermore, the compounds described above can be used to stabilize rubbers and elastomers. These can be natural rubber (NR) or synthetic rubber materials.

[0050] If the organic materials are oils and fats, these can be based on mineral oils, vegetable fats, or animal fats, or they can be oils, fats, or waxes based on, for example, synthetic esters. Examples of vegetable oils and fats include palm oil, olive oil, rapeseed oil, linseed oil, soybean oil, sunflower oil, and castor oil. Animal fats include, for example, fish oils or beef tallow.

[0051] Furthermore, the compounds according to the invention can be used to stabilize low-molecular-weight or oligomeric polyols, such as those used in polyurethane production. Suitable hydroxy compounds include, for example, butane-1,4-diol, oligomeric ethylene glycols, or tetrahydrofuran oligomers.

[0052] The compounds according to the invention can also be used as stabilizers for lubricants, hydraulic oils, engine oils, turbine oils, gear oils, metalworking fluids, or as lubricating greases. These mineral or synthetic lubricants are predominantly based on hydrocarbons.

[0053] It is possible and advantageous for the plastic, for example the plastic molding compound, to contain at least one further additive selected from the group consisting of UV absorbers, light stabilizers, hydroxylamine-based stabilizers, benzofuranone-based stabilizers, nucleating agents, impact improvers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersing agents, compatibilizers, oxygen scavengers, acid scavengers, marking agents and antifogging agents.

[0054] Possible additional additives are selected from the groups of UV absorbers, light stabilizers, stabilizers, hydroxylamines, benzofurans, nucleating agents, impact enhancers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, marking agents, or antifogging agents. In a preferred embodiment, the compositions contain, in particular, acid scavengers, e.g., based on salts of long-chain acids such as calcium stearate, magnesium stearate, zinc stearate, calcium lactate, or hydrotalcites.In a further preferred embodiment, the compositions contain stabilizers from the group of phenolic antioxidants and phosphites / phosphonites, hydroxylamines, amines, lactones, thio compounds and / or light stabilizers from the group of hindered amines (HALS) and / or UV absorbers.

[0055] Suitable light stabilizers include compounds based on 2-(2'-Hydroxyphenyl)-benzotriazoles, 2-hydroxybenzophenones, esters of benzoic acids, acrylates, oxamides and 2-(2-Hydroxyphenyl)-1,3,5-triazines.

[0056] Geeignete 2-(2'-Hydroxyphenyl)benzotriazole sind beispielsweise 2-(2'-Hydroxy-5'methylphenyl)benzotriazol, 2-(3',5'-Di-tert-butyl-2'-hydroxyphenyl)-benzotriazol, 2-(5'-tert-Butyl-2'-hydroxy-phenyl)benzotriazol, 2-(2'-Hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazol, 2-(3',5'-Di-tert-butyl-2'-hydroxyphenyl)-5-chlorobenzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'-methylphenyl-5-chlorobenzotriazol, 2-(3'-sec-Butyl-5'-tert-butyl-2'-hydroxy-phenyl)benzotriazol, 2-(2'-Hydroxy-4'-octyloxyphenyl)benzotriazol, 2-(3',5'-Di-tert-amyl-2'-hydroxyphenyl)benzotriazol, 2-(3',5'-Bis(α,α-dimethylbenzyl)-2'-hydroxyphenyl)benzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl)-5-chlorobenzotriazol, 2-(3'-tert-Butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)-5-chlorobenzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl) phenyl)-5-chlorobenzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazol,2-(3'-tert-Butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl) phenyl)benzotriazol, 2-(3'-tert-Butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)benzotriazol, 2-(3'-Dodecyl-2'-hydroxy-5'-methylphenyl) benzotriazol, 2-(3'-tert-Butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl)phenylbenzotriazol, 2,2'-Methylenbis [4-(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenol]; das Produkt der Umesterung von 2-[3'-tert-Butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazol mit Polyethylenglycol 300; [R-CH2CH2-COO-CH2CH2-]-2, wobei R = 3'-tert-Butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl, 2-[2'-Hydroxy-3'-(α,α-dimethylbenzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl]benzotriazol, 2-[2'-hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5'-(a,a-dimethylbenzyl)phenyl]benzotriazol.,

[0057] Suitable 2-hydroxybenzophenones are, for example, 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy-4,4'-dimethyoxy derivatives of 2-hydroxybenzophenones.

[0058] Suitable acrylates include, for example, ethyl α-cyano-β,β-diphenyl acrylate, isooctyl α-cyano-β,β-diphenyl acrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, butyl α-cyano-β-methyl-p-methoxycinnamate, methyl α-carbomethoxy-p-methoxycinnamate and N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline.

[0059] Suitable esters of benzoic acids include, for example, 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, and 2-methyl-4,6-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate.

[0060] Suitable oxamides include, for example, 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and its mixtures with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.

[0061] Geeignete 2-(2-Hydroxyphenyl)-1,3,5-Triazine sind beispielsweise 2,4,6-Tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazin, 2-(2-Hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin, 2-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin, 2,4-Bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazin, 2-(2-Hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl-1,3,5-triazin, 2-(2-Hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin, 2-(2-Hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin, 2-[2-Hydroxy-4-(2-hydroxy-3-butyloxypropoxy)-phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazin, 2-[2-Hydroxy-4-(2-hydroxy-3-octyloxypro-pyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazin, 2-[4-(Dodecyloxy / Tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin, 2-[2-Hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl-1,3,5-triazin, 2-(2-Hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1,3,5-triazin,2-(2-Hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazin, 2,4,6-Tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazin, 2-(2-Hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazin, 2-{2-Hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl-1,3,5-triazin.,

[0062] Geeignete phenolische Antioxidantien sind beispielsweise: Alkylierte Monophenole, wie z.B. 2,6-Di-tert-butyl-4-methylphenol, 2-tert-Butyl-4,6-dimethylphenol, 2,6-Di-tert-butyl-4-ethylphenol, 2,6-Di-tert-butyl-4-n-butylphenol, 2,6-Di-tert-butyl-4-isobutylphenol, 2,6-Dicyclopentyl-4-methylphenol, 2-(α-Methylcyclohexyl)-4,6-dimethylphenol, 2,6-Dioctadecyl-4-methylphenol, 2,4,6-Tricyclohexylphenol, 2,6-Di-tert-butyl-4-methoxymethylphenol, lineare oder verzweigte Nonylphenole, wie z.B. 2,6-Dinonyl-4-methylphenol, 2,4-Dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-Dimethyl-6-(1'-methylheptadec-1'-yl)phenol, 2,4-Dimethyl-6-(1'-methyltridec-1'-yl)phenol und Mischungen hiervon; Alkylthiomethylphenole, wie z.B. 2,4-Dioctylthiomethyl-6-tert-butylphenol, 2,4-Dioctylthiomethyl-6-methylphenol, 2,4-Dioctylthiomethyl-6-ethylphenol, 2,6-Didodecylthiomethyl-4-nonylphenol; Hydrochinone und alkylierte Hydrochinone, wie z.B. 2,6-Di-tert-butyl-4-methyoxyphenol, 2,5-Di-tert-butylhydrochinon, 2,5-Di-tert-amylhydrochinon, 2,6-Diphenyl-4-octadecyloxyphenol, 2,6-Di-tert-butylhydroquinone, 2,5-Di-tert-butyl-4-hydroxyanisole, 3,5-Di-tert-butyl-4-hydroxyanisole, 3,5-Di-tert-butyl-4-hydroxyphenylstearate, Bis(3,5-di-tert-butyl-4-hydroxylphenyl)adipate; Tocopherols, such as α-, β-, γ-, δ-tocopherol and mixtures of these (Vitamin E); hydroxylated thiodiphenyl ethers, such as 2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-secamylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl) disulfide; Alkylidene bisphenols, such as 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-Methylenbis[6-(α-methylbenzyl)-4-nonylphenol], 2,2'-Methylenbis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4'-Methylenbis(2,6-di-tert-butylphenol, 4,4'-Methylenbis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan, 2,6-Bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-Tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butan, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecyl-mercaptobutan, Ethylenglycol-bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrat], Bis(3-tert-butyl-4-hydroxy-5-methylphenyl)dicyclopentadien, Bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalat, 1,1-Bis-(3,5-dimethyl-2-hydroxyphenyl)butan, 2,2-Bis(3,5-di-tert-butyl-4-hydroxyphenyl)propan, 2,2-Bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutan, 1,1,5,5-Tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentan; O-, N- und S-Benzyl-Verbindungen, wie z.B. 3,5,3',5'-Tetra-tert-butyl-4,4'-dihydroxydibenzylether,Octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetat, Tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetat, Tris(3,5-di-tert-butyl-4-hydroxybenzyl)amin, , Bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalat, Bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfid, Isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetat; hydroxybenzylierte Malonate, wie z.B. Dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonat, Dioctadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonat, Didodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonat, Bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonat; aromatische Hydroxybenzylverbindungen, wie z.B. 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzol, 1,4-Bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzol, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol; Triazinverbindungen, wie z.B. 2,4-Bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazin, 2-Octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazin, 2-Octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazin, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazin, 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurat, 1,3,5-Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurat, 2,4,6-Tris(3,5-di-tert-butyl-4-hydroxphenylethyl)-1,3,5-triazin, 1,3,5-Tris(3,5-di-tert-butyl-4-hydroyphenylpropionyl)hexahydro-1,3,5-triazin, 1,3,5-Tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurat; Benzylphosphonate, wie z.B. Dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonat, Dietyhl-3,5-di-tert-butyl-4-hydroxybenzylphosphonat, Dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonat, Dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonat, das Calciumsalz des Monoethylesters der 3,5-Di-tert-butyl-4-hydroxybenzylphosphonsäure; Acylaminophenole, wie z.B. 4-Hydroxylauranilid, 4-Hydroxystearanilid, Octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamat; Ester der β-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionsäure mit ein- oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, n-Octanol, i-Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris(hydroxyethyl)isocyanurat, N,N'-Bis(hydroxyethyl)oxamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octan; Ester der β-(5-tert-Butyl-4-hydroxy-3-methylphenyl)propionsäure mit ein- oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, n-Octanol, i-Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris(hydroxyethyl)isocyanurat, N,N'-bis(hydroxyethyl)oxamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan,4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octan, 3,9-Bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecan; Ester der β-(3,5-Dicyclohexyl-4-hydroxyphenyl)propionsäure mit ein- oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris-(hydroxyethyl)isocyanurat, N,N'-bis(hydroxyethyl)oxamid, 3-Thiaundecanol, 3-Thiapentadecanol, Trimethylhexandiol, Trimethylolpropan, 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octan; Ester der 3,5-Di-tert-butyl-4-hydroxyphenyl)essigsäure mit ein- oder mehrwertigen Alkoholen, z.B. Methanol, Ethanol, Octanol, Octadecanol, 1,6-Hexandiol, 1,9-Nonandiol, Ethylenglycol, 1,2-Propandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol, Triethylenglycol, Pentaerythritol, Tris(hydroxyethyl)isocyanurat, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane; Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide, N,N'-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyloxy)ethyl]oxamide; ascorbic acid (vitamin C). Particularly favored phenolic antioxidants are the following structures:

[0063] Geeignete Phosphite / Phosphonite sind beispielsweise: Triphenylphosphit, Diphenylalkylphosphite, Phenyldialkylphosphite, Tri(nonylphenyl)phosphit, Trilaurylphosphite, Trioctadecylphosphit, Distearylpentaerythritoldiphosphit, Tris-(2,4-di-tert-butylphenyl) phosphit, Diisodecylpentaerythritoldiphosphit, Bis(2,4-di-tert-butylphenyl)pentaerythritoldiphosphit, Bis(2,4-di-cumylphenyl)pentaerythritoldiphosphit, Bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritoldiphosphit, Diisodecyloxypentaerythritoldiphosphit, Bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritoldiphosphit, Bis(2,4,6-tris(tert-butylphenyl)pentaerythritoldiphosphit, Tristearylsorbitoltriphosphit, Tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylendiphosphonit, 6-Isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocin, Bis(2,4-di-tert-butyl-6-methylphenyl)methylphosphit, Bis(2,4-di-tert-butyl-6-methylphenyl) ethylphosphit, 6-Fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-dioxaphosphocin, 2,2'2''-Nitrilo[triethyltris(3,3'',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite], 2-ethylhexyl(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl))phosphite, 5-Butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,3,2-dioxaphosphiran.,

[0064] Other suitable phosphites are the commercial products Weston 705 (manufacturer: Addivant) and Doverphos LGP 11 (manufacturer: Dover Chemical Corporation), which are liquid phosphites.

[0065] Particularly favored phosphites / phosphonites are: where n > 1

[0066] Geeignete aminische Antioxidantien sind beispielsweise: N,N'-Di-isopropyl-p-phenylendiamin, N,N'-Di-sec-butyl-p-phenylendiamin, N,N'-Bis(1,4-dimethylpentyl)-p-phenylendiamin, N,N'-Bis(1-ethyl-3-methylpentyl)-p-phenylendiamin, N,N'-Bis(1-methylheptyl)-p-phenylendiamin, N,N'-Dicyclohexyl-p-phenylendiamin, N,N'-Diphenyl-p-phenylendiamin, N,N'-Bis(2-naphthyl)-p-phenylendiamin, N-Isopropyl-N'-phenyl-p-phenylendiamin, N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylen-diamin, N-(1-Methylheptyl)-N'-phenyl-p-phenylendiamin, N-Cyclohexyl-N'-phenyl-p-phenylendiamin, 4-(p-Toluolsulfamoyl)diphenylamin, N,N'-Dimethyl-N,N'-di-sec-butyl-p-phenylendiamin, Diphenylamin, N-Allyldiphenylamin, 4-Isopropoxydiphenylamin, N-Phenyl-1-naphthylamin, N-(4-tert-Octylphenyl)-1-naphthylamin, N-Phenyl-2-naphthylamin, octyliertes Diphenylamin, z.B.p,p'-Di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylamino-phenol, bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethyl-phenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetra-methyl-4,4'-diaminodiphenylmethane, 1,2-bis[(2-methyl-phenyl)amino]ethane, 1,2-bis(phenylamino)propane, (o-tolyl)biguanide, Bis[4-(1',3'-dimethylbutyl)phenyl]amine, . tert -octylated N-phenyl-1-naphthylamine, a mixture of mono- and dialkylated tert -Butyl / tert -Octyldiphenylamines, a mixture of mono- and dialkylated nonyldiphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of mono- and dialkylated isopropyl / isohexyl diphenylamines, a mixture of mono- and dialkylated tert -Butyldiphenylamines, 2,3-Dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, a mixture of mono- and dialkylated tert -Butyl / tert- Octylphenothiazines, a mixture of mono- and dialkylated tert -Octylphenothiazines, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene and mixtures or combinations thereof.

[0067] Other suitable amine antioxidants are hydroxylamines or N-oxides (nitrons), such as N,N-dialkylhydroxylamine, N,N-dibenzylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-distearylhydroxylamine, N-benzyl-α-phenylnitrone, N-octadecyl-α-hexadecylnitrone, and Genox EP (addivant) according to the formula: R 1 , R 2 = C 14 - C 24 Alkyl Genox EP

[0068] Other suitable stabilizers are thiosynergists. Suitable thiosynergists include, for example, distearylthiodipropionate, dilaurylthiodipropionate, or the compound according to the following formula:

[0069] Other suitable stabilizers, especially for polyamides, are copper salts such as copper(I) iodide, copper(I) bromide, or copper complexes such as triphenylphosphine-copper(I) complexes.

[0070] Suitable hindered amines include, for example, 1,1-bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebazate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebazate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)-n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4- tert-Octylamino-2,6-dichloro-1,3,5-triazine, Tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate, Tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butanetetracarboxylate, 1,1'-(1,2-ethanediyl)-bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, linear or cyclic condensation products of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, the reaction product of 7,7,9,9-Tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro-[4,5]decane and epichlorohydrin.

[0071] Preferred hindered amines continue to exhibit the following structures:

[0072] Preferred oligomeric and polymeric hindered amines exhibit the following structures:

[0073] Suitable lactones include, for example: 5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-3H-benzofuran-2-one, 5,7-di-tert-butyl-3-[-4-(2-stearoyloxyethoxy)phenyl]-benzofuran-2-one, 3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one), as well as phosphorus-containing 3-phenylbenzofuran-2ones.

[0074] Suitable metal deactivators include, for example, N,N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyldihydrazide, oxanilide, isophthaloyldihydrazide, sebacoylbisphenylhydrazide, N,N'-diacetyladipoyldihydrazide, N,N'-bis(salicyloyl)oxylyldihydrazide, and N,N'-bis(salicyloyl)thiopropionyldihydrazide.

[0075] Suitable dispersants include, for example: polyacrylates, e.g., copolymers with long-chain side groups, polyacrylate block copolymers; alkylamides: e.g., N,N'-1,2-ethanediylbisoctadecanamide; sorbitan esters, e.g., monostearyl sorbitan esters; titanates and zirconates; reactive copolymers with functional groups, e.g., polypropylene-co-acrylic acid, polypropylene-co-maleic anhydride, polyethylene-co-glycidyl methacrylate; polystyrene-alt-maleic anhydride polysiloxanes: e.g., dimethylsilanediol-ethylene oxide copolymer, polyphenylsiloxane copolymer; amphiphilic copolymers: e.g., polyethylene block-polyethylene oxide; dendrimers, e.g., dendrimers containing hydroxyl groups.

[0076] Suitable nucleating agents include, for example, talc, alkali or alkaline earth salts of mono- and polyfunctional carboxylic acids such as benzoic acid, succinic acid, adipic acid, sodium benzoate, zinc glycerolate, aluminum hydroxybis(4-tert-butyl)benzoate, benzylidene sorbitols such as 1,3:2,4-bis(benzylidene)sorbitol or 1,3:2,4-bis(4-methylbenzylidene)sorbitol, 2,2'-methylene-bis-(4,6-di- tert -butylphenyl)phosphate, as well as triamides and diamides such as trimesic acid tricyclohexylamide, trimesic acid tri(4-methylcyclohexylamide), trimesic acid tri(tert-butylamide), N,N',N"-1,3,5-benzenetriyltris(2,2-dimethyl-propanamide) or 2,6-naphthalenedicarboic acid dicyclohexylamide.

[0077] Suitable antinuclear agents include, for example, azine dyes such as nigrosine, ionic liquids and / or lithium salts.

[0078] Suitable flame retardants include, for example: a) Inorganic flame retardants such as Al(OH)₃, Mg(OH)₂, AlO(OH), MgCO₃, layered silicates such as montmorillonite or sepiolite, unmodified or organically modified, double salts such as Mg-Al silicates, POSS (polyhedral oligomeric silsesquioxane) compounds, huntite, hydromagnesite or halloysite, as well as Sb₂O₃, Sb₂O₅, MoO₃, zinc stannate, zinc hydroxystannate; b) Nitrogen-containing flame retardants such as melamine, melem, melam, melon, melamine derivatives, melamine condensation products or melamine salts, benzoguanamine, polyisocyanurates, allantoin, phosphacenes, in particular melamine cyanurate, melamine phosphate, dimelamine phosphate, melamine pyrophosphate, melamine polyphosphate, melamine metal phosphates such as Melamine aluminum phosphate, melamine zinc phosphate, melamine magnesium phosphate, and the corresponding pyrophosphates and polyphosphates, poly-[2,4-(piperazine-1,4-yl)-6-(morpholin-4-yl)-1,3,5-triazine], ammonium polyphosphate, melamine borate, melamine hydrobromide, c) radical initiators, such as e.g.alkoxyamines, hydroxylamine esters, azo compounds, sulfenamides, sulfenimides, dicumyl or polycumyl, hydroxyimides and their derivatives such as hydroxyimide esters or hydroxyimide ethers; d) Phosphorus-containing flame retardants such as red phosphorus, phosphates such as resorcinol diphosphate, bisphenol A diphosphate and their oligomers, triphenyl phosphate, ethylenediamine diphosphate, phosphinates such as salts of hypophosphorous acid and their derivatives such as alkyl phosphinate salts, e.g., diethylphosphinate aluminum or diethylphosphinate zinc or aluminum phosphinate, aluminum phosphite, aluminum phosphonate, phosphonate esters, oligomeric and polymeric derivatives of methanephosphonic acid, 9,10-dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide (DOPO) and their substituted compounds; e) Halogen-containing flame retardants based on chlorine and bromine such as polybrominated diphenyl oxides, such asDecabromodiphenyl oxide, Tris(3-bromo-2,2-bis(bromomethyl)propyl phosphate, Tris(tribromneopentyl) phosphate, Tetrabromophthalic acid, 1,2-Bis(tribromphenoxy)ethane, Hexabromcyclododecane, Brominated diphenylethane, Tris-(2,3-dibromopropyl)isocyanurate, Ethylene bis(tetrabromophthalimide), Tetrabromobisphenol A, Brominated polystyrene, Brominated polybutadiene or polystyrene-brominated polybutadiene copolymers, Brominated polyphenylene ether, Brominated epoxy resin, Polypentabrombenzyl acrylate, possibly in combination with Sb₂O₃ and / or Sb₂O₅, f) Borates such as zinc borate or calcium borate, possibly on a support material such as silica, g) Sulfur-containing compounds such as elemental sulfur, disulfides and Polysulfides, thiuram sulfide, dithiocarbamates, mercaptobenzthiazole and sulfenamides, h) anti-drip agents such as polytetrafluoroethylene, i) silicon-containing compounds such as polyphenylsiloxanes, j) carbon modifications such asCarbon nanotubes (CNTs), expandable graphite or graphene k), and combinations or mixtures thereof.

[0079] Suitable fillers and reinforcing materials include synthetic or natural materials such as calcium carbonate, silicates, glass fibers, glass beads (solid or hollow), talc, mica, kaolin, barium sulfate, metal oxides and hydroxides, carbon black, graphite, carbon nanotubes, graphene, wood flour, or fibers from natural products such as cellulose or synthetic fibers. Other suitable fillers include hydrotalcites or zeolites or layered silicates such as montmorillonite, bentonite, beidelite, mica, hectorite, saponite, vermiculite, ledikite, magadite, illite, kaolinite, wollastonite, attapulgite, and halloysite.

[0080] Suitable pigments can be inorganic or organic. Examples of inorganic pigments include titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, and carbon black. Examples of organic pigments include anthraquinones, anthanthrones, benzimidazolones, quinacridones, diketopyrrolopyrroles, dioxazines, indanthrones, isoindolinones, azo compounds, perylenes, phthalocyanines, and pyranthrones. Other suitable pigments include metal-based effect pigments and metal oxide-based pearlescent pigments.

[0081] Suitable chain extenders for the linear molecular weight increase of polycondensation polymers such as polyesters or polyamides include, for example, diepoxides, bis-oxazolines, bis-oxazolones, bis-oxazines, diisocyanates, dianhydrides, bis-acyl lactams, bis-maleimides, dicyanates, and (poly)carbodiimides. Other suitable chain extenders are polymeric compounds such as polystyrene-polyacrylate-polyglycidyl(meth)acrylate copolymers, polystyrene-maleic anhydride copolymers, and polyethylene-maleic anhydride copolymers.

[0082] Suitable optical brighteners include, for example, bisbenzoxazoles, phenylcoumarins or bis(styryl)biphenyls, and in particular optical brighteners of the following formulas:

[0083] Suitable filler deactivators include, for example, polysiloxanes, polyacrylates, especially block copolymers such as polymethacrylic acid-polyalkylene oxide or polyglycidyl(meth)acrylates and their copolymers, e.g., with styrene, as well as epoxides, e.g., of the following structures:

[0084] Suitable antistatic agents include, for example, ethoxylated alkylamines, fatty acid esters, alkyl sulfonates and polymers such as polyetheramides.

[0085] Suitable antiozonants are the above-mentioned amines such as N,N'-Diisopropyl-p-phenylenediamine, N,N'-Di-sec-butyl-p-phenylenediamine, N,N'-Bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N'-Dicyclohexyl-p-phenylenediamine, N-Isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-Dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-(1-Methylheptyl)-N'-phenyl-p-phenylenediamine, N-Cyclohexyl-N'-phenyl-p-phenylenediamine.

[0086] Suitable demolding aids include, for example, montan waxes.

[0087] The incorporation of the stabilizers and / or the additive composition, and optionally the additional additives, into the plastic is carried out using conventional processing methods. The polymer is melted and mixed with the additive composition according to the invention and any further additives, preferably using mixers, kneaders, and extruders. Preferred processing machines include extruders such as single-screw extruders, twin-screw extruders, planetary roller extruders, ring extruders, and co-kneaders, preferably equipped with vacuum degassing. Processing can be carried out under air or, optionally, under inert gas conditions, such as nitrogen as a protective gas.

[0088] Furthermore, the additive compositions can be produced and incorporated in the form of masterbatches or concentrates containing, for example, 20-90% of the additives or additive compositions according to the invention in a polymer. Concentrates consisting of the additive and / or the additive composition and a lubricant are also preferred. The lubricant is preferably a salt of a long-chain fatty acid such as calcium stearate, magnesium stearate, or zinc stearate, a polyethylene wax, or a polypropylene wax. These concentrates can then be in the form of compacted, granulated, or extruded product forms.

[0089] Furthermore, it is advantageous if, in addition to the compound according to general formula I, at least one further primary and / or secondary antioxidant, in particular at least one further primary and / or secondary antioxidant selected from the group consisting of phenolic antioxidants, phosphites, phosphonites, amines, hydroxylamines and mixtures or combinations thereof, is used to stabilize the organic materials.

[0090] In the event that the organic materials are plastic or polymer compositions containing the stabilizers according to the invention, they are particularly suitable for further processing into special molded parts, such as injection-molded parts, foils or films, foams, fibers, cables and pipes, profiles, hollow bodies, tapes, membranes, such as geomembranes, which are produced by extrusion, injection molding, blow molding, calendering, pressing, spinning processes, rotomoulding, or coating processes, e.g., for the electrical and electronics industry, the construction industry, the transport industry (automotive, aircraft, ship, rail), for medical applications, for household and electrical appliances, vehicle parts, consumer goods, packaging, furniture, and textiles. These molded parts are also part of the present invention.

[0091] Preferably, the compositions according to the invention consist of 0.01-5.0 wt% of the stabilizers according to the invention according to general formula I, 0-5.0% of a further additive and 95-99.99 wt% of a polymer, particularly preferably 0.02-3 wt% of the stabilizers according to the invention, 0-3.0% of a further additive and 97-99.98% of a polymer, most particularly preferred are 0.05-2 wt% of the stabilizers according to the invention, 0-2 wt% of a further additive and 98-99.95 wt% of a polymer.

[0092] The present invention further relates to an organic material which, for stabilization purposes, comprises at least one stabilizer or a mixture of several stabilizers according to general formula I, as defined above. For the purposes of the correspondingly stabilized organic material, all the aforementioned descriptions of general formula I apply equally. In a particularly preferred embodiment, the organic material is a polymer composition, especially comprising the polymers as described above.

[0093] Furthermore, the invention relates to a method for stabilizing organic materials, in particular plastic compositions, especially against oxidative, thermal and / or actinic degradation, in which one or more compounds according to general formula I are incorporated into the organic material. The incorporation can be carried out in any manner known from the prior art.

[0094] The present invention will be explained in more detail with reference to the following examples. Synthesis of the new stabilizers:

[0095] The absolute toluene (99.8%), lithium diisopropylamide (LDA), and elemental sulfur (pa, ≥ 99.5%) used in the syntheses were obtained from Sigma Aldrich, phenothiazine (98+%) from Alfa Aesar, acetonitrile, anhydrous diethyl ether, and the 1.6 molar (15%) n-butyllithium solution in n-hexane from Merck KGaA, and chlorodiphenylphosphine was provided by BASF. The compound 4,4'-bis(α,α-dimethylbenzyl)diphenylamine (BDBDA) was obtained from TCI Tokyo Kasei, and absolute tetrahydrofuran from Acros Organics. 2-Chloro-5,5-dimethyl-1,3,2-dioxa-phosphorinane (DDP-Cl) was synthesized from phosphorus trichloride and 1,3-dimethylpropane-1,3-diol in a manner known from the literature. Example 1 Synthesis of phenothiazine-DOP:

[0096]

[0097] Into a carefully dried, nitrogen-filled 500 mL three-necked flask equipped with a magnetic stirrer, nitrogen supply, and pressure-equalizing dropping funnel, absolute toluene (150 mL) and 47.3 g of a 2 M lithium diisopropylamide solution in THF (LDA; 0.095 mol) were added via syringe through a septum. Phenothiazine (17.93 g, 0.090 mol) was then added countercurrently under nitrogen. In the slightly warmed dropping funnel, absolute toluene (120 mL) was added via syringe through a septum, followed by molten DOP-Cl (21.23 g, 0.090 mol) in countercurrent nitrogen. (The bottle containing the DOP-Cl had been previously warmed to approximately 100°C to melt the reagent.) The DOP-Cl solution was added dropwise over 30 minutes at room temperature with stirring. The reaction mixture was then stirred for 1 hour at room temperature. After the solids (mainly lithium chloride) had settled at the bottom of the flask, the mixture was removed.After the residue had separated from the flask wall, the supernatant solution was decanted under inert conditions. 80 mL of absolute toluene were added to the residue via a syringe through a septum. The mixture was stirred for 30 min at 45 °C and, after settling of the solid, decanted. Both solutions were combined, and the toluene was removed under vacuum. The resulting residue was dissolved in 80 mL of dry acetonitrile with heating. Upon cooling, the phenothiazine-DOP precipitated. After storing the tightly sealed flask in a refrigerator (approx. 15 h), the supernatant solution was separated by decantation. Finally, the adhering solvent was removed under vacuum. In this way, phenothiazine-DOP was obtained as a white solid in a yield of 78%.

[0098] 31< P-NMR (300 MHz, CDCl 3 , 8) δ = 94.2 ppm. 1< H-NMR (300 MHz, CDCl 3 , 8) δ = 7.86 - 6.77 (m, 16.3H) ppm. Example 2 Synthesis of phenothiazine DOPS:

[0099]

[0100] Into a carefully dried, nitrogen-filled 250 mL three-necked flask equipped with a magnetic stirrer and nitrogen supply, 60 mL of absolute toluene were added via syringe through a septum, along with phenothiazine-DOP (4.97 g, 0.013 mol) and elemental sulfur (0.43 g, 0.013 mol) in countercurrent nitrogen. The reaction mixture was stirred first for 3 h at 80 °C, then for 30 min at 90 °C. After removal of the toluene by vacuum distillation, a crystalline solid was obtained. NMR spectroscopy showed that the sulfurization reaction to form phenothiazine-DOPS had proceeded completely.

[0101] 31< P-NMR (300 MHz, CDCl 3 , 14) δ = 67.4 ppm. 1< H-NMR (300 MHz, CDCl 3 , 14) δ = 8.11 - 6.95 (m, 17.5H) ppm. Example 3 Synthesis of phenothiazine PPh2:

[0102]

[0103] Into a carefully dried, nitrogen-filled 250 mL three-necked flask equipped with a magnetic stirrer, dropping funnel, and nitrogen supply line, absolute toluene (40 mL) and LDA (7 mL, 0.014 mol) were added via syringe through a septum, and phenothiazine (2.39 g, 0.012 mol) were added countercurrently with nitrogen. The mixture was heated to approximately 40 °C to dissolve and then cooled in an ice bath. Subsequently, absolute toluene and chlorodiphenylphosphine (2.65 g, 0.012 mol) were added dropwise over 10 minutes via syringe through a septum with nitrogen into a dropping funnel. The reaction mixture was stirred in the ice bath for 1 h. NMR spectroscopy of the reaction solution showed that the desired product had been formed.

[0104] 31P-NMR (300 MHz, CDCl3) δ = 70.3 ppm. 1H-NMR (300 MHz, CDCl3) δ = 7.66 - 6.56 ppm. Example 4 Synthesis of phenothiazine PPh2S:

[0105]

[0106] In a carefully dried, nitrogen-filled 250 mL three-necked flask equipped with a magnetic stirrer, reflux condenser, and nitrogen supply line, absolute toluene (60 mL) and elemental sulfur (0.42 g, 0.013 mol) were added countercurrently to the reaction solution obtained in Exemplar 3 via a syringe through a septum. The reaction mixture was stirred for 3 h at 80 °C and stored overnight in a refrigerator (2 °C). The precipitate was filtered off, the filtrate was concentrated by vacuum distillation to remove the toluene, cooled again, and the precipitate was filtered off once more. The product was then recrystallized from acetonitrile. The yield was 2.74 g (54%). NMR spectroscopy showed that the sulfurization reaction had proceeded to completion, forming phenothiazine PPh₂S.

[0107] 31< P-NMR (300 MHz, CDCl 3 ) δ = 62.6 ppm. 1< H-NMR (300 MHz, CDCl3) δ = 8.17 - 6.89 ppm. Example 5 Synthesis of phenothiazine-DDP:

[0108]

[0109] In a carefully dried and argon-filled 100 mL three-necked flask equipped with a magnetic stirrer, septum, and argon supply line, absolute THF (40 mL) and phenothiazine (2.99 g, 0.015 mol) were added. Then, 9.4 mL of a 15% solution of n-butyllithium in n-hexane (0.015 mol) was added through the septum via a syringe while stirring. After stirring the flask contents for 20 min, 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane (DDP-Cl, 2.52 g, 0.015 mol) was added dropwise through the septum via a syringe over 10 minutes. The reaction mixture was stirred for 2 h at room temperature. NMR spectroscopy of the reaction solution showed the formation of phenothiazine-DDP.

[0110] 31<P-NMR (300 MHz, CDCl 3 ) δ = 127.0 ppm. Example 6 Synthesis of phenothiazine-DDPS:

[0111]

[0112] Elemental sulfur (0.48 g, 0.015 mol) was added countercurrently to the solution of phenothiazine DDP in THF obtained in embodiment 5 using argon. The mixture was then stirred for 3 h at 50 °C. The solvent was then removed under vacuum, and the residue was recrystallized from acetonitrile. The yield of spectroscopically pure phenothiazine DDP was 85%. 31< P-NMR (300 MHz, CDCl 3 ) δ = 56.1 ppm. 1< H-NMR (300 MHz, CDCl 3 ) δ = 7.94 - 7.14 (m, 8.5 H, Ar), 3.83 - 3.57 (m, 4 H, CH 2 ), 1.23 (s, 3 H, CH 3 ), 0.76 (s, 3 H, CH 3 ) ppm. 13< C-NMR (300 MHz, CDCl 3 ) δ = (140.0, 130.1, 127.7, 127.5, 125.9, 123.7, 77.0, 32.1, 22.1, 21.1) ppm melting point (°C): 205 Example 7 Synthesis of BDBDA-DOP:

[0113]

[0114] The apparatus used was carefully dried. The synthesis was carried out under a nitrogen atmosphere.

[0115] 4.5 g (0.011 mol) of 4,4'-bis(α,α-dimethylbenzyl)diphenylamine (BDBDA) were placed in a 250 ml three-necked flask equipped with a magnetic stirrer, dropping funnel, and argon supply line. The mixture was then heated in an oil bath (85°C) for approximately 30 min at approximately 0.02 mbar. After cooling to room temperature and filling the flask with nitrogen, 50 ml of dry toluene were added via syringe. Subsequently, 6.9 ml of a 15% solution of n-butyllithium in n-hexane (0.011 mol) were added via syringe over a period of 10 min. The reaction mixture was heated to approximately 40°C and then cooled in an ice bath. Finally, a solution of 2.6 g (0.011 mol) of DOP-Cl in abs. Toluene (30 ml) was added dropwise over 10 minutes. The reaction mixture was then stirred at room temperature for 1 hour. Subsequently, the lithium chloride was filtered off under inert conditions. The resulting BDBDA-DOP solution was used for embodiment 9.

[0116] 31<P-NMR (300 MHz, CDCl 3 ) δ = 79.9 ppm. Example 8 Synthesis of BDBDA-DOPS:

[0117]

[0118] Elemental sulfur (0.45 g, 0.014 mol) was added to the BDBDA-DOP solution in toluene obtained in embodiment 7. The mixture was then stirred for 3 h at 80 °C. The solvent was then removed under vacuum. The resulting residue was recrystallized twice from acetonitrile.

[0119] The yield of spectroscopically pure BDBDA-DOPS was 73%.

[0120] 31<P-NMR (300 MHz, CDCl 3 ) δ = 66.0 ppm. Example 9 Synthesis of BDBDA-DPhP:

[0121]

[0122] The apparatus used was carefully dried. The synthesis was carried out under a nitrogen atmosphere.

[0123] In a 250 mL three-necked flask equipped with a magnetic stirrer, dropping funnel, and argon supply line, 6.1 g (0.015 mol) of 4,4'-bis(α,α-dimethylbenzyl)diphenylamine (BDBDA) were added. The mixture was then heated in an oil bath (85°C) for approximately 30 min at approximately 0.02 mbar. After cooling to room temperature and filling the flask with nitrogen, 50 mL of dry toluene were added via syringe. Subsequently, 9.4 mL of a 15% solution of n-butyllithium in n-hexane (0.015 mol) were added via syringe over a period of 10 min. The reaction mixture was stirred for 30 min. Then, a solution of 3.3 g (0.015 mol) of DPhP-Cl in abs. Toluene (30 ml) was added dropwise over 10 minutes. The reaction mixture was then stirred at room temperature for 3 hours. Subsequently, the lithium chloride was filtered off under inert conditions. The resulting BDBDA-DPhP solution was used for embodiment 10.

[0124] 31<P-NMR (300 MHz, CDCl 3 ) δ = 54.9 ppm. Example 10 Synthesis of BDBDA-DPhPS:

[0125]

[0126] Elemental sulfur (0.58 g, 0.018 mol) was added to the BDBDA-DPhP solution in toluene obtained in embodiment 9. The mixture was then stirred for 3 h at 60 °C. The solvent was then removed under vacuum. The resulting residue was recrystallized twice from acetonitrile. The yield of spectroscopically pure BDBDA-DPhPS was 78% (based on DPhP-Cl).

[0127] 31<P-NMR (300 MHz, CDCl 3 ) δ = 62.3 ppm. Example 11 Synthesis of BDBDA-DDP:

[0128]

[0129] 206.8 g of 4,4'-bis(α,α-dimethylbenzyl)diphenylamine (BDBDA) were placed in a carefully dried, argon-filled, two-liter, three-necked flask equipped with a magnetic stirrer, dropping funnel, and argon supply line. The mixture was then heated in an oil bath (85°C) for approximately 30 minutes at approximately 0.02 mbar. After cooling to room temperature and filling the flask with nitrogen, 500 ml of dry THF were added via syringe. A colorless solution was obtained. Over the course of approximately 60 minutes, approximately 323 ml of a 1.6 molar solution of n-butyllithium in n-hexane were added dropwise (via syringe) while stirring. The flask was cooled in a water bath during this process. A yellow solution was obtained, which was stirred for 30 minutes.

[0130] Then, approximately 84.3 g of DDP-Cl were added dropwise via syringe over about 90 minutes while stirring (the flask remained in the water bath). As the reagent was added, the yellow color faded, and after about two-thirds of the DDP-Cl had been added, the reaction mixture became cloudy. Then, 100 ml of dry n-hexane were added while stirring to precipitate any remaining dissolved LiCl. Stirring continued for several minutes. The flask containing the product solution was stored overnight at room temperature under nitrogen. The precipitated LiCl was removed by decantation under inert conditions. Most of the volatile components of the solution were then distilled into a cold trap, with the pressure slowly reduced to approximately 50 mbar and the temperature of the oil bath increased to 60°C. A viscous, oily residue was obtained, which was further heated to approximately 70°C. Approximately 800 ml of acetonitrile was added to this through a funnel.

[0131] The contents of the flask were then heated under a nitrogen atmosphere to just below the boiling point. A turbidity remained, which settled after the stirring was stopped. After cooling, the contents of the flask were decanted under inert conditions into a 2 L flask filled with nitrogen. The remaining residue was mixed with approximately 100 mL of acetonitrile, heated, and filtered through a paper filter (into the 2 L flask containing the decanted solution). Upon cooling, crystalline product precipitated from the combined product solution onto the flask wall. After approximately 2 hours, when a significant amount of the product had already crystallized, the flask was transferred to a refrigerator and stored there overnight. The supernatant solution was then separated by decantation. The crude product thus obtained was recrystallized from 750 mL of acetonitrile under a nitrogen atmosphere.The product was collected using a porcelain funnel / filter paper (in the presence of air) and then dried in a 1-liter flask under vacuum using a diaphragm pump, with gentle heating using a hairdryer and frequent agitation. A white powder (201 g) was obtained. An additional 10 g of the product was isolated from the residual solution of the recrystallization. NMR spectroscopy of the product showed a purity of ≥ 99.5%.

[0132] 31<P-NMR (300 MHz, CDCl 3 ) δ = 121.0 ppm; 1< H-NMR (300 MHz, CDCl 3 ) δ = 7.10-7.33 (m, 18 H, Ar), 3.53 - 3.56 (d, 4 H, CH 2 ), 1.72 (s, 12 H, H 3 CC-CH 3 ), 1.04 (s, 3 H, CH 3 ), 0.61 (s, 3 H, CH 3) ppm. 13< C-NMR (300 MHz, CDCl3, chromium acetylacetonate) δ = 140.0 (s, 2C), 146.2 (s, 2C), 142.7 (d, 2C), 128.0 (s, 4C), 127.4 (s, 4C), 126.8 (s, 4C), 125.6 (s, 2C), 124.8 (d, 4C), 72.0 (s, 2C), 42.6 (s, 2C), 32.3 (d, 1C), 30.8 (s, 4C), 22.4 (d, 2C) ppm. Melting point (°C): 98-99°C Example 12 Synthesis of BDBDA-DDPS:

[0133]

[0134] The apparatus used was carefully dried.

[0135] BDBDA (239.7 g) was added, then the apparatus was evacuated three times and refilled with nitrogen to remove any remaining moisture. Subsequently, 440 ml of dry THF were added via syringe, resulting in a colorless solution. Over approximately 70 minutes, 375 ml of a 1.6 M butyllithium solution in n-hexane were added dropwise (via syringe) while stirring. The flask was cooled in a water bath during this time. A yellow solution was obtained, which was stirred for another 30 minutes. Then, over approximately 80 minutes, 97.8 g of DDP-Cl were added dropwise via syringe while stirring (flask still in the water bath), resulting in a pale yellow suspension. A 3131P NMR spectrum of this suspension was recorded (CDCl3), which showed complete conversion of the DDP-Cl.

[0136] The reaction mixture was stored overnight at room temperature under nitrogen.

[0137] The precipitated LiCl was separated by decantation under inert conditions. The solution was transferred to a 2 L flask. 20 mL of THF and 50 mL of cyclohexane were added to the salt residue (to largely dissolve any remaining product). The mixture was then stirred and filtered through a paper filter (into the 2 L flask containing the BDBDA-DDP solution). The combined solution was light brown and was subsequently subjected to the sulfurization reaction.

[0138] The 2-liter flask was equipped with an internal thermometer. Approximately 20 g of sulfur were then added in four portions over about 15 minutes while stirring, with the flask immersed in an oil bath. A significant temperature increase to approximately 45°C was observed. Once the temperature had passed its maximum, the oil bath was heated to 57°C over 30 minutes. Stirring continued for another 30 minutes at an internal temperature of approximately 50–52°C, after which an NMR sample was taken. The 3131P NMR spectrum of the product solution showed that the sulfurization had occurred with very high selectivity.

[0139] The resulting solution was transferred to a 2-liter single-necked flask. It was rinsed with 40 mL of warm THF, as a small amount of product had already crystallized at the bottom of the three-necked flask. Further product precipitated at the bottom of the single-necked flask. To achieve sufficiently complete crystallization of the product, approximately half of the solvents THF and n-hexane were distilled using a rotary evaporator (water bath: 40°C). The pressure was reduced in small increments. During distillation, a significant portion of the product crystallized. The sealed flask was stored overnight in a refrigerator (approximately 5°C).

[0140] The crystallized product was collected by filtration. A beige-colored crystalline solid was obtained, whose 31P NMR and proton spectra already showed good purity (approximately 99 mol% purity in the phosphorus spectrum; the proton spectrum also showed hardly any impurities). Approximately 230 g of the substance were obtained. The remaining solution was washed with water to remove the remaining LiCl (the aqueous phase was brown and was discarded). It was then strongly concentrated on a rotary evaporator under partial vacuum, yielding another product fraction. Further purification was carried out by recrystallization from acetonitrile and drying under vacuum with gentle heating. A total of 256 g of pure BDBDA-DDPS was obtained as a white solid (77% of the theoretical amount).

[0141] 31<P-NMR (300 MHz, CDCl 3 ) δ = 64.1 ppm; 1< H-NMR (300 MHz, CDCl 3 ) δ = 7.15-7.35 (m, 18 H, Ar), 4.28-4.36 (q, 2H, CH 2 ), 3.69-3.82 (q, 2H, CH 2 ), 1.68 (s, 12 H, H 3 CC-CH 3 ), 0.87 (s, 3 H, CH 3 ), 0.67 (s, 3 H, CH 3 ) ppm. Melting point (°C): 133-135 Example 13 Synthesis of BDBDA-DDP from PCl 3 , BDBDA and 1,3-dimethylpropane-1,3-diol:

[0142]

[0143] The apparatus used was carefully dried. The synthesis was carried out under a nitrogen atmosphere.

[0144] BDBDA (11.4 g) was added, then the apparatus was evacuated three times and refilled with nitrogen to remove any moisture adhering to the BDBDA powder. Subsequently, 100 ml of absolute diethyl ether was added via syringe. The resulting solution was cooled to approximately 10°C. Then, 2.8 g of triethylamine and 3.84 g of phosphorus trichloride were added successively with stirring, resulting in the precipitation of a colorless solid (triethylammonium chloride). Stirring continued for three hours at room temperature. The triethylammonium chloride was then filtered off under inert conditions. The solution was then concentrated under partial vacuum. A 31<³¹P NMR spectrum was recorded, which included only the phosphorus signal of BDBDA-PCl₂ (300 MHz, CDCl₃; 6 = 148.8 ppm).

[0145] Then, 6 g of triethylamine and 6 g of 1,3-dimethylpropane-1,3-diol were added. After stirring the reaction mixture at room temperature for two hours, 50 ml of diethyl ether were added. The precipitated triethylammonium chloride was then filtered off and the solvent distilled off. The remaining residue was recrystallized from acetonitrile. The yield of spectroscopically pure BDBDA-DDP was 10.9 g (72% of the theoretical amount, based on BDBDA).

[0146] 31<P-NMR (300 MHz, CDCl 3 ) δ = 121.0 ppm; 1< H-NMR (300 MHz, CDCl 3 ) δ = 7.10-7.33 (m, 18 H, Ar), 3.53 - 3.56 (d, 4 H, CH 2 ), 1.72 (s, 12 H, H 3 CC-CH 3 ), 1.04 (s, 3 H, CH 3 ), 0.61 (s, 3 H, CH 3 ) ppm. Example 14 Synthesis of PhP(BDBDA)2

[0147]

[0148] The apparatus used was carefully dried. The synthesis was carried out under a nitrogen atmosphere.

[0149] BDBDA (116.4 g) was added, then the apparatus was evacuated three times and refilled with nitrogen to remove any remaining moisture. Subsequently, 750 ml of dry diethyl ether was added via syringe. A colorless solution was obtained. Over the course of one hour, 171.3 ml of a 1.6 molar butyllithium solution in n-hexane was added dropwise via syringe while stirring and cooling in an ice-water bath. A pale yellow solution of the lithium salt of BDBDA was obtained. Stirring continued for 45 minutes, and then 24.52 g of PhP-Cl₂ were added dropwise via syringe over 20 minutes while stirring the still-cooled solution. Initially, turbidity developed due to the precipitation of LiCl. Towards the end of the reagent addition, a large amount of product precipitated out. Stirring was continued for another hour at a moderate speed.A 31< P-NMR spectrum of this suspension (CDCl 3) was recorded, which showed complete conversion of PhP-Cl 2 and highly selective product formation.

[0150] The majority of the volatile components were then distilled under a slight vacuum into a receiving flask cooled with liquid nitrogen (the flask was immersed in a water bath of approximately 20°C). Stirring was no longer possible towards the end of the distillation. A stronger vacuum was then briefly applied. 500 ml of absolute toluene (the tip) was added to the resulting residue. The mixture was then heated to approximately 65°C with gentle stirring, at which point the product dissolved, leaving only the LiCl (LiCl) undissolved. This was filtered off under inert conditions. The toluene was then distilled under partial vacuum into a receiving flask cooled with liquid nitrogen (the flask was immersed in an oil bath, initially at approximately 55°C, which was increased to approximately 75°C towards the end of the distillation). Once the toluene had been almost completely distilled, the residue solidified.The resulting solid was stirred for one hour with 1 liter of acetonitrile under reflux and a nitrogen atmosphere. The product was collected by filtration using a porcelain funnel and filter paper (in the presence of air). A white, crystalline filter cake was obtained, which was dried under vacuum with moderate heating. The yield of PhP(BDBDA)₂ was 112 g (approximately 89% of the theoretically possible amount).

[0151] 31<P-NMR (300 MHz, CDCl 3 ) δ = 86.0 ppm; 1< H-NMR (300 MHz, CDCl 3 ) δ = 7.10-7.33 (m, 25 H, Ar), 6.97-7.05 (d, 8H, Ar), 6.78-6.84 (d, 8H, Ar), 1.66 (s; 24 H, H 3 CC-CH 3 ) ppm. Melting point (°C): 116-118 Studies on the stabilizer effect in polypropylene:

[0152] The stabilizing effects of polypropylene were tested at 230 °C in a twin-screw microextruder. Polypropylene types MOPLEN HP556E and MOPLEN HP500N (products of LyondellBasell Industries) were used, which had previously been milled at 10,000 rpm using a centrifugal mill and dried for approximately 5 hours at 100 °C in a vacuum drying oven (20 mbar). Three extrusion tests were performed for each polymer-additive mixture. The total amount of polymer-additive mixture used in each test was 4 g. Forces were recorded at one-second intervals during each run using software.

[0153] Tables 1 and 2 list the additives used, their concentrations, and the forces acting at different extrusion times (each as average values ​​from three individual tests). For comparison, extrusions were also carried out with the established stabilizer system ADK-STAB A611 / Caesit AV, as well as pure MOPLEN HP556E and MOPLEN HP5. Table 1 (Tests with MOPLEN HP 556E) Additive Force after 30 s Force after 60 s Force after 120 s Force after 180 s Force after 300 s Force after 600s (N) (N) (N) (N) (N) (N) - 1830 1760 1660 1590 1430 1260 ADK-STAB A611 1800 1820 1720 1660 1540 1270 0,2% Caesit AV e)< 0.1 % Phenothiazine-DOP 2040 2030 1940 1960 1990 1930 0,2% Phenothiazine-DOP 1980 1990 2000 1990 2010 1970 0,5% Phenothiazine-DOP 2000 2010 1970 1980 1990 2050 1,0% Phenothiazine DOPS 2000 2040 1990 2060 2020 2010 0,5% Phenothiazine DOPS 2020 2000 1970 1920 1930 2010 1,0% Table 2 (Tests with MOPLEN HP 500N) Additive Force after 30 s Force after 60 s Force after 120 s Force after 180 s Force after 300 s Force after 600s (N) (N) (N) (N) (N) (N) - 550 530 510 480 460 450 Ceasit 0.2% 640 600 580 560 540 520 ADK-STAB A611 0.2% 610 570 560 540 520 530 PhP(BDBDA)2 0.2% 730 730 750 740 740 730 Ceasit AV 0.2% BDBDA-DDP 0.2% 600 600 610 600 590 580 Multiple extrusions

[0154] For the extrusions, polypropylene of type Moplen HP556E LOI 033L30 from the company was used. LyondellBasell The tests were performed on a twin-screw extruder. Thermo Scientific Process 11 carried out with a screw diameter of 11 mm.

[0155] In a twin-screw extruder, a total of 350 g each of pure polypropylene, polypropylene, and polypropylene with an additive of 0.3% phenothiazine DOPS (PTZ DOPS) were extruded three times. After each extrusion, the sample was dried for approximately 1 hour in a vacuum drying oven at 60 °C. 50 g were then reserved, and the remaining granules were extruded again. The temperature profile used is shown in Table 3, and the parameters obtained for each extrusion are listed in Tables 4 to 6. Table 3: Temperature profile used for extrusions on the twin-screw extruder. nozzle Zone 7 Zone 6 Zone 5 Zone 4 Zone 3 Zone 2 210 230 230 230 230 220 210 Table 4: Parameters of the three extrusions of pure polypropylene. 1. Extrusion 2. Extrusion 3. Extrusion Engine speed / rpm 150 150 150 Throughput / g / h 456 516 552 Melting point / °C 216-217 215-217 215-216 Melting pressure / bar 26-28 30-33 31-33 Torque / % 27-29 35-39 36-41 Torque / Nm 3.1-3.3 4.2-4.6 4.4-5.0 Torque / kW 0.04-0.05 0.06-0.07 0.06-0.07 Table 5: Parameters of the three extrusions of polypropylene with an addition of 0.3% phenothiazine_DOPS. Pure PP 1. Extrusion 2. Extrusion 3. Extrusion Engine speed / rpm 150 150 150 Throughput / g / h 468 576 552 Melting point / °C 213-215 214-217 214-217 Melting pressure / bar 27-29 32-33 30-32 Torque / % 28-30 37-40 33-37 Torque / Nm 3.4-3.6 4.4-4.8 3.9-4.4 Torque / kW 0.05 0.06-0.07 0.06-0.07

[0156] Melt-flow measurements were then performed on all samples obtained, which had been dried overnight in a vacuum drying oven at approximately 60 °C. For this purpose, 3.5 g of each sample were measured at 230 °C and a weight of 2.16 kg (DIN EN ISO 19069). Each sample was measured two to three times, and the results were then averaged. According to the manufacturer, the melt flow rate (MVR) of the pure polymer should be 1.10 cm³ / 10 min. Table 5 shows the results of these measurements. Table 6: List of the average MVR values ​​of the three extrusions of pure polypropylene, as well as of polypropylene with an addition of 0.3% phenothiazine_DOPS. sample MVR / ccm / 10min pure PP (granules, not extruded) 1,1294 1. Extrusion of pure PP 1,2120 2. Extrusion of pure PP 1,3073 3. Extrusion of pure PP 1,3714 1.Extrusion of PP with 0.3% PTZ_DOPS 1,1311 2.Extrusion of PP with 0.3% PTZ_DOPS 1,1179 3.Extrusion of PP with 0.3% PTZ_DOPS 1,1524

[0157] The comparison of the results in Table 5 shows the very good stabilizing effect of the stabilizers according to the invention, since, in contrast to pure PP, no or only a slight reduction in molecular weight (= higher MVR) takes place. Stabilizing effect of the substances according to the invention:

[0158] The phosphorus-containing phenothiazine derivatives according to the invention were tested for their effectiveness as processing stabilizers. The influence of the new additives on the melt viscosity of polypropylene during the extrusion process (230°C) was investigated. During the tests, the force in the extruder was measured as a function of time. The measured force is proportional to the applied torque, and the latter is directly dependent on the melt viscosity. A decrease in the measured force thus indicates polymer degradation during the extrusion process. For comparison, the established stabilizer system ADK-STAB A611 (0.2%) / Caesit AV (0.1%) was tested. Comparative tests with pure polypropylene were also carried out.

[0159] As expected, a continuous decrease in force was observed during the extrusion process with pure polypropylene. After 10 minutes, the measured force was only about two-thirds of the value measured after 30 seconds. When using the established stabilizer mixture, the force initially remained constant, as expected, but dropped significantly after only 3 minutes of extrusion and, after 10 minutes, fell to about two-thirds of the initial value, just as with pure polypropylene. This means that the comparison system loses its effectiveness after a relatively short extrusion time.

[0160] Surprisingly, no change in force was observed during extrusion of polypropylene to which small amounts of the stabilizers according to the invention had been added. Even after a long residence time in the extruder (e.g., 10 minutes!), no decrease in force occurred, while the comparison system had long since lost its effect (sharp drop in the measured force).

[0161] Thus, the stabilizers according to the invention showed excellent and much higher effectiveness compared to the comparison system.

[0162] The tests showed that when using the stabilizers according to the invention, processing of polypropylene in the melt (extrusion, injection molding, etc.) is possible without degradation processes.

[0163] The primary or secondary antioxidant can be incorporated into the organic material in the same way as the compound according to general formula I.

[0164] Primary antioxidants act via a radical mechanism with chain-breaking properties. Secondary antioxidants have a stabilizing effect based on an ionic mechanism and act as hydroperoxide decomposers. A combination of both groups can be used to achieve synergistic effects.

Claims

1. Use of a compound or of mixtures of a plurality of compounds in accordance with general formula I         A-By     Formula I wherein the fragment A has the following meaning wherein in each case independently of one another X is a sulphur atom, n is 0 or 1, x is 0 or 1, Z1 and Z2 are selected from the group consisting of hydrogen, alkyl residues, aryl residues, alkylaryl residues, arylalkyl residues, heterocyclic residues, wherein one or more further fragments A and / or B may be bonded to the aforementioned residues, and a grouping -O-Z3, where Z3 is selected from alkyl residues, aryl residues, alkylaryl residues, arylalkyl residues and heterocyclic residues, and a grouping -S-Z4, where Z4 is selected from alkyl residues, aryl residues, alkylaryl residues, arylalkyl residues and heterocyclic residues, wherein, in the case of x = 1, the residues Z1 and Z2 together with the phosphorus atom can form a ring system to which one or more further fragments A and / or B can be bonded, the fragment B has the following meaning wherein in each case independently of one another R1 to R10 are selected from the group consisting of hydrogen, alkyl residues, aryl residues, alkylaryl residues, arylalkyl residues and heterocyclic residues, where the residues R1 and R6 can also be linked via a grouping -Y- linking the phenyl groups, where Y is selected from the group consisting of S, O, NH, PH and a covalent bond, where the fragments A and B are connected to each other by covalent bonding of the phosphorus atom and the nitrogen atom, and wherein y is 1 or 2, where x + y = 2, for stabilizing organic materials, in particular against oxidative thermal and / or actinic degradation, characterized in that the fragment A is selected from the following residues where x = y = 1 where x = 0 and y = 2, or where x = y = 1 where x = y = 1 wherein in each case independently of one another R11 is selected from the group consisting of hydrogen, alkyl residues, aryl residues, alkylaryl residues, arylalkyl residues and heterocyclic residues, R12 is selected from the group consisting of hydrogen, alkyl residues, aryl residues, alkylaryl residues, arylalkyl residues, heterocyclic residues, wherein the aforementioned residues may also have heteroatoms and / or one or more further fragments A and / or B may be bonded to the aforementioned residues, and X and n are as defined above.

2. The use according to claim 1, for stabilizing plastics, coatings, lubricants, hydraulic oils, engine oils, turbine oils, transmission oils, metalworking fluids, chemicals or monomers.

3. The use according to one of the preceding claims, characterized in that the fragment A is selected from the following residues where, in each case, x = y = 1, where x = 0 and y = 2, and where, in each case, x = y = 1.

4. The use according to one of the preceding claims, characterized in that the compound according to general formula I is defined as follows wherein X, n and B are as defined in claim 1.

5. The use according to any one of the preceding claims, characterized in that the fragment B is selected from the group consisting of the following residues where y = 1 or 2, where y = 1 or 2, and where y =1 or 2 wherein R2 to R5 and R7 to R10 and Y are each independently defined as in claim 1.

6. The use according to any one of the preceding claims, characterized in that the fragment B is selected from the group consisting of the following residues7. The use according to one of the preceding claims, characterized in that the compound in accordance with general formula I is selected from the group consisting of the following compounds: wherein in each case independently of one another R11 is selected from the group consisting of hydrogen, alkyl residues, aryl residues, alkylaryl residues, arylalkyl residues and heterocyclic residues.

8. The use according to one of the preceding claims, characterized in that the compound in accordance with general formula I or, in the case of a mixture of a plurality of compounds in accordance with general formula I the totality of all the compounds in accordance with general formula I, is included in the organic material at a weight proportion of 0.01 to 10 wt.%, preferably of 0.05 to 5 wt.%, particularly preferably of 0.1 to 1.5 wt.%.

9. The use according to any one of the preceding claims for stabilization of plastics, wherein the plastic is selected from the group consisting of a) polymers made from olefins or diolefins such as polyethylene (LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE, UHMWPE), metallocene PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-pentene-1, polybutadiene, polyisoprene, polycyclooctene, polyalkylene-carbon monoxide copolymers, as well as copolymers in the form of random or block structures such as polypropylene-polyethylene (EP, EPM or EPDM), ethylene-vinyl acetate (EVA), ethylene-acrylic ester, such as, for example, ethylene butyl acrylate, ethylene acrylic acid and its salts (ionomers), as well as terpolymers such as ethylene acrylic acid glycidyl (meth)acrylate, graft polymers such as Polypropylene-graft-maleic anhydride, polypropylene-graft-acrylic acid, polyethylene-graft-acrylic acid, polyethylene-polybutyl acrylate-graft-maleic anhydride and blends thereof, b) polystyrene, polymethylstyrene, poly-alpha-methylstyrene, polyvinyl naphthalene, polyvinylbiphenyl, polyvinyltoluene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS), styrene-ethylene-butylene-styrene (SEBS), Styrene-ethylenepropylene-styrene, styrene-isoprene, styrene-isoprene-styrene (SIS), styrene-butadiene-acrylonitrile (ABS), styrene-acrylonitrile (SAN), styrene-acrylonitrile-acrylate (ASA), styrene-ethylene, styrene-maleic acidurea anhydride polymers incl. corresponding graft copolymers such as styrene on butadiene, maleic anhydride on SBS or SEBS, as well as graft copolymers of methyl methacrylate, styrene-butadiene and ABS (MABS), and hydrogenated polystyrene derivatives, c) halogen-containing polymers such as polyvinyl chloride (PVC), polychloroprene, and polyvinylidene chloride (PVDC), copolymers of vinyl chloride and vinylidene chloride or composed of vinyl chloride and vinyl acetate, chlorinated polyethylene, polyvinylidene fluoride, epichlorohydrin homo and copolymer thereof; d) polymers of unsaturated esters such as polyacrylates and polymethacrylates such as polymethyl methacrylate (PMMA), polybutyl acrylate, polyauryl acrylate, poly stearyl acrylate, polyglycidyl methacrylate, polyacrylonitrile, polyacrylamides, copolymers such as polyacrylonitrile-poly alkyl acrylate; e) polymers of unsaturated alcohols and derivatives, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polyallyl melamine, f) polyacetals, such as e.g. polyoxymethylene (POM) or copolymers with, for example, butanal, g) polyphenylene oxides and blends with polystyrene or polyamides, h) polymers of cyclic ethers such as polyethylene glycol, polypropylene glycol, polyethylene oxide, polypropylene oxide, polytetrahydrofuran; i) polyurethanes of hydroxy terminated polyethers or polyesters and aromatic or aliphatic isocyanates, in particular linear polyurethanes (TPU), polyureas; j) polyamides such as polyamide-6, 6.6, 6.10, 4.6, 4.10, 6.12, 10.10, 10.12, 12.12, polyamide 11, polyamide 12 as well as (partly) aromatic polyamides, such as polyphthalamides, for example produced from terephthalic acid and / or isophthalic acid and aliphatic diamines or from aliphatic dicarboxylic acids such as adipic acid or sebacic acid and aromatic diamines such as 1,4- or 1,3-diaminobenzene, blends of different polyamides such as PA-6 and PA 6.6 or blends of polyamides and polyolefins such as PA / PP, k) polyimides, polyamide-imides, polyether imides, polyester imides, poly(ether)ketones, polysulfones, polyether sulfones, polyaryl sulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins, l) polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxy-carboxylic acids such as Polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTT), polyethylene naphthylate (PEN), poly-1,4-dimethyl-olcyclohexane terephthalate, polyhydroxybenzoate, polyhydroxynaphthalate, polylactic acidure (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polyethylene succinate, polytetranethylene succinate, polycaprolactone, m) polycarbonates, polyester carbonates and blends such as PC / ABS, PC / PBT, PC / PET / PBT, PC / PA n) cellulose derivatives, such as e.g. cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate, o) epoxy resins consisting of di- or polyfunctional epoxy compounds in combination with, for example, hardeners based on amines, anhydrides, dicyandiamide, mercaptans, isocyanates or catalytic hardeners, p) phenolic resins such as, for example phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde resins; q) unsaturated polyester resins of unsaturated dicarboxylic acids and diols with vinyl compounds; r) silicones; s) and mixtures, combinations or blends of two or more of the aforementioned polymers.

10. The use according to any one of the preceding claims, characterized in that the plastic contains at least one further additive selected from the group consisting of UV absorbers, light stabilizers, hydroxylamine-based stabilizers, benzofuranone-based stabilizers, nucleating agents, impact strength improvers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, dispersing agents, compatibilizers, oxygen scavengers, acid scavengers, marking agents and antifogging agents.

11. The use according to one of the preceding claims, wherein, for stabilizing the organic materials, in addition to the compound according to general formula I, at least one further primary and / or secondary antioxidant, in particular at least one further primary and / or secondary antioxidant selected from the group consisting of phenolic antioxidants, phosphites, phosphonites, amines, hydroxylamines and mixtures or combinations thereof, is used to stabilize the organic materials.

12. A plastics composition comprising at least one stabilizer or a mixture of several stabilizers according to general formula I         A-By     Formula I wherein A, B and y are as defined in claim 1.

13. A method of stabilizing organic materials, in particular against oxidative, thermal and / or actinic degradation, in which a compound or a plurality of compounds in accordance with general formula I         A-By     Formula I wherein A, B and y are as defined in claim 1, is incorporated into the organic material.