EP4301810A1 - Verwendung einer stabilisatorzusammensetzung zur stabilisierung von organischen materialien, stabilisatorzusammensetzung, masterbatch, zusammensetzung, formmasse der formteile, verfahren zur oxidativen, thermischen aktinischen stabilisierung eines thermoplastischen kunststoffs sowie verwendung einer zusammensetzung - Google Patents

Verwendung einer stabilisatorzusammensetzung zur stabilisierung von organischen materialien, stabilisatorzusammensetzung, masterbatch, zusammensetzung, formmasse der formteile, verfahren zur oxidativen, thermischen aktinischen stabilisierung eines thermoplastischen kunststoffs sowie verwendung einer zusammensetzung

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Publication number
EP4301810A1
EP4301810A1 EP22710988.1A EP22710988A EP4301810A1 EP 4301810 A1 EP4301810 A1 EP 4301810A1 EP 22710988 A EP22710988 A EP 22710988A EP 4301810 A1 EP4301810 A1 EP 4301810A1
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EP
European Patent Office
Prior art keywords
agents
styrene
sulfite
weight
tert
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP22710988.1A
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German (de)
English (en)
French (fr)
Inventor
Rudolf Pfaendner
Matthias POLIDAR
Elke METSCH-ZILLIGEN
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Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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Publication of EP4301810A1 publication Critical patent/EP4301810A1/de
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
    • C08K13/02—Organic and inorganic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2207/00—Properties characterising the ingredient of the composition
    • C08L2207/20—Recycled plastic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2310/00—Masterbatches

Definitions

  • stabilizer composition for stabilizing organic materials.
  • stabilizer composition masterbatch.
  • Composition molding mass of the molded parts.
  • Antioxidants in Ullmann 's encyclopedia of industrial chemistry Wiley-VCH Verlag, Weinheim 2015.
  • Typical representatives of primary antioxidants are, for example, phenolic antioxidants, amines, but also lactones.
  • Classes of secondary antioxidants are phosphorus compounds such as phosphites or phosphonites, but also organo-sulphur compounds such as sulfides or disulfides.
  • primary and secondary antioxidants are often combined, which leads to an advantageous synergistic effect.
  • HAS hindered amine stabilizers
  • processing stabilizers such as lactones, phosphites or hydroxylamines.
  • the present invention thus relates to the use fertil at least one stabilizer composition containing or consisting of at least one sulfite and / or at least one thiosulfate in combination with at least one polymeric or oligomeric hindered amine for stabilizing organic materials, in particular against oxidative, thermal and / or actinic degradation.
  • New stabilizer compositions and a new process for stabilizing plastics in particular are therefore proposed, which are highly effective, environmentally friendly and have a favorable cost structure.
  • a good stabilizing effect can be achieved with combinations of hindered amines and inorganic sulfites, and the hindered amine can be partially replaced by inexpensive sulfites.
  • the stabilizer composition is suitable for stabilizing plastics, coatings, lubricants, hydraulic oils, engine oils, turbine oils, gear oils, metalworking fluids, chemicals or monomers.
  • plastics are selected from the group consisting of virgin plastics, plastic recyclates and mixtures or combinations thereof.
  • the at least one sulfite is preferably an inorganic sulfite, an inorganic disulfite or an inorganic hydrogen sulfite, preferably a mono-, di-, tri- or tetravalent metal, the metal preferably being an alkali metal, an alkaline earth metal ,
  • Aluminum and/or zinc is particularly preferably a sulfite selected from the group consisting of sodium sulfite, potassium sulfite, lithium sulfite, calcium sulfite, magnesium sulfite, aluminum sulfite, zinc sulfite and mixtures and combinations thereof, the sulfite being in particular in its anhydrous form shape is used
  • the thiosulfate is in particular a thiosulfate of a mono-, di-, tri- or tetravalent metal, the metal preferably being an alkali metal, an alkaline earth metal, aluminum and/or zinc, particularly preferably sodium thiosulfate. the thiosulphate being used in particular in its anhydrous form.
  • Sterically hindered amines are heterocyclic amines which have at least one alkyl, cycloalkyl or aryl group adjacent to the particular amine group.
  • Preferred heterocyclic amines are derivatives based on piperidine, piperazine, piperazinone or piperazinedione, in particular the hindered amines have 2,2 ′ ,6,6′-tetramethylpiperidine units.
  • the at least one polymeric or oligomeric hindered amine preferably has a number average molecular weight of >1000 g/mol, in particular the at least one polymeric or oligomeric hindered amine is selected from the group consisting of the following compounds
  • n is an integer from 2-100, preferably 3-20, particularly preferably 3-10 and
  • R -OC(O)-alkyl and in particular R -OC(O)-C 15 H 31 or -OC(O)-C 17 H 35 where in the case of an NH group this is independently replaced on each occurrence by a N-alkyl group such as N-methyl or N-octyl, an N-alkoxy group such as N-methoxy or N-octyloxy, a cycloalkyl group such as N-cyclohexyloxy and the N-(2- hydroxy-2-methylpropoxy) group can be replaced, as well as mixtures and combinations thereof.
  • all of the at least one sulfite and/or thiosulfate and all of the at least one polymeric or oligomeric hindered amine are in a weight ratio of 1:99 to 99:1, preferably 20:80 to 80:20 , more preferably from 30:70 to 70:30, most preferably from 40:60 to 60:40.
  • the stabilizer composition is preferably suitable for stabilizing plastics, the plastic being selected in particular 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, such as natural rubber (NR), polycyclooctene, polyalkylene-carbon monoxide copolymers, and copolymers in the form of random or block structures such as e.g.
  • 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
  • EP polypropylene-polyethylene
  • EPM ethylene vinyl acetate
  • ethylene acrylic esters such as ethylene butyl acrylate, ethylene acrylic acid and its salts (ionomers)
  • 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 acid anhy d-rid as well as blends such as LDPE/LLDPE or long-chain branched polypropylene copolymers which are produced with alpha-olefins as comonomers such as with 1-butene, 1-hexene, 1-0cten or 1-0ctade
  • 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, polyamideimides, polyetherimides, polyesterimides, poly(ether)ketones, polysulfones, polyethersulfones, polyarylsulfones, polyphenylene sulfides, polybenzimidazoles, polyhydantoins,
  • Polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids such as, for example, polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTI), 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
  • hardeners based on amines, anhydrides , dicyandiamide, mercaptans, isocyanates or catalytic hardeners p) phenolic resins such as phenol-formaldehyde resins, urea-formaldehyde resins, melamine-formaldehyde yd resins, q) unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds, e.g. styrene, alkyd resins, allyl resins r) silicones, e.g. based on dimethylsiloxanes, methyl-phenylsiloxanes or diphenylsiloxanes, e.g. terminated with vinyl groups, s) and mixtures, combinations or blends of two or more of the aforementioned polymers.
  • phenolic resins such as phenol-formaldehyde resins, urea-formaldehyde resins,
  • polymers specified under a) to r) are copolymers, they can be present in the form of random, block or tapered structures.
  • polymers mentioned can be present in the form of linear, branched, star-shaped or hyper-branched structures. If the polymers specified under a) to r) are stereoregular polymers, they can be present in the form of isotactic, stereotactic, but also atactic forms or as stereoblock copolymers.
  • the polymers specified under a) to r) can have both amorphous and (partially) crystalline morphologies.
  • polyolefins mentioned under a) can also be crosslinked, e.g. B. cross-linked polyethylene, which is then referred to as X-PE.
  • the present compounds can be used to stabilize rubbers and elastomers.
  • This can be natural rubber (NR) or synthetic rubber materials.
  • Plastic recyclates in particular thermoplastic plastic recyclates, are also preferred as plastic.
  • the thermoplastic recyclate is particularly preferably selected from the group consisting of polymers made from olefins or diolefins, such as e.g. Polyethylene, in particular LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE and UHMWPE, metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-pentene-1, polybutadiene, polyisoprene, polycyclooctene, polyalkylene-carbon lenmonoxide copolymers, as well as corresponding copolymers in the form of random or block structures such as polypropylene-polyethylene (EP), EPM or EPDM, ethylene-vinyl acetate (EVA), ethylene-acrylic esters such as ethylene-butyl acrylate, ethylene-acrylic acid-glycidyl acrylate, and corresponding graftpo - lymers such as polypropylene-g-maleic an
  • the one thermoplastic is very particularly preferably a polyolefin recyclate.
  • the thermoplastic recyclate can be polypropylene, in particular a polypropylene recyclate homopolymer or copolymer, or polyethylene, in particular a polyethylene recyclate, eg HDPE, LDPE, LLDPE or mixtures thereof.
  • additives selected from the group consisting of primary and/or secondary antioxidants, UV absorbers, light stabilizers, metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, impact modifiers, plasticizers, lubricants, rheology modifiers, thixotropic agents, Chain extenders, processing aids, mold release agents, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anticrosslinking agents, hydrophilicizing agents, hydrophobing agents, adhesion promoters, dispersing agents, compatibilizers, oxygen scavengers, acid scavengers, Blowing agents, degradation additives, defoaming aids, odor traps, marking agents, antifogging agents, fillers and reinforcing materials are used
  • compositions contain, in particular, phosphites or phosphonites, fillers or acid scavengers.
  • Suitable phenolic antioxidants are:
  • Alkylated monophenols such as 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-methyl-phenol, 2-(a-methylcyclohexyl)-4,6-dimethylphenol , 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethyl- phenol, linear or branched nonylphenols such as 2,6-dinonyl- 4-methyl-phenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-dimethyl-6-(
  • alkylthiomethyl phenols such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol;
  • Hydroxylated thiodiphenyl ethers such as 2,2'-thiobis(6-tert-butyl-4-methyl-phenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl- 3-methyl- phenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-secamylphenol), 4,4'-bis( 2,6-dimethyl-4-hydroxyphenyl) disulfide;
  • O-, N- and S-benzyl compounds such as 3,5,3',5'-tetra-tert-butyl-4,4'-di-hydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercaptoace - tat, tridecyl 4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, , bis(4-tert-butyl-3-hydroxy- 2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate; Hydroxybenzylated malonates such as dioctadecyl 2,2-bis(3,
  • Aromatic hydroxybenzyl compounds such as 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert- butyl-4-hydroxy-benzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxy-benzyl)phenol;
  • Triazine compounds such as 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3 ,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxy-phenoxy) -1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3, 5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(
  • Benzyl phosphonates such as dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl
  • acylaminophenols such as 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate;
  • Esters of ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with monohydric or polyhydric alcohols e.g. methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol tol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.
  • Esters of ⁇ -(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with monohydric or polyhydric alcohols e.g. methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol , 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]
  • Esters of ⁇ -(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with monohydric or polyhydric alcohols e.g. methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2- Propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris-(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha- 2,6,7-trioxabicyclo[2.2.2]octane;
  • Esters of (3,5-di-tert-butyl-4-hydroxyphenyl)acetic acid with monohydric or polyhydric alcohols e.g. methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, 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 ⁇ -(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 ( Naugard® XL-1 sold by Uniroyal);
  • vitamin C Ascorbic acid (vitamin C).
  • Particularly preferred phenolic antioxidants are the following structures: ⁇
  • n is an integer and is between 2 and 10.
  • phenolic antioxidants are based on renewable raw materials phenolic antioxidants such.
  • Preferred fillers are calcium carbonate, silicates, talc, mica, kaolin, metal oxides and metal hydroxides, carbon black, graphite, wood flour or fibers from natural products such as cellulose.
  • Other suitable fillers are hydrotalcites or zeolites or phyllosilicates such as montmorillonite, bentonite, beidelite, mica, hectorite, saponite, vermiculite, ledikite, magadite, illite, kaolinite, wollastonite, attapulgite.
  • Suitable secondary antioxidants are, in particular, phosphites or phosphonites such as, for example, triphenyl phosphite, diphenylalkyl phosphites, phenyldialkyl phosphites, tri(nonylphenyl) phosphite, trilauryl phosphites, trioctadecyl phosphite, distearylpentaerythritol diphosphite, tris-(2,4-di-tert-butylphenyl) phosphite, diisodecylpentaerythritol diphosphite (2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-di-cumylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl
  • Particularly preferred phosphites/phosphonites are:
  • the phosphite tris-(2,4-di-tert-butylphenyl) phosphite is very particularly preferably used as the secondary antioxidant.
  • a preferred phosphonite is:
  • Suitable secondary antioxidants are also organo-sulphur compounds such as, for example, sulfides and disulfides, for example distearyl thiodipropionate, dilauryl thiodipropionate; Ditridecyldithiopropionate, Ditetradecylthiodipropionate, 3-(dodecylthio)-, 1,T-[2,2-bis[[3-(dodecylthio)-1-oxopropoxy]methyl]-1,3-propanediyl]propanoic acid ester.
  • organo-sulphur compounds such as, for example, sulfides and disulfides, for example distearyl thiodipropionate, dilauryl thiodipropionate; Ditridecyldithiopropionate, Ditetradecylthiodipropionate, 3-(dodecylthio)-, 1,T-[
  • Suitable acid scavengers are salts of mono, di, tri or tetravalent metals, preferably alkali metals, alkaline earth metals, aluminum or zinc, formed in particular with fatty acids such as calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium laurate, Calcium behenate, calcium lactate, calcium stearoyl-2-lactate
  • suitable acid scavengers are hydrotalcites, in particular synthetic hydrotalcites on aluminum, Magnesium and zinc base, hydrocalumite, zeolites, alkaline earth metal oxides, in particular calcium oxide and magnesium oxide and zinc oxide, alkaline earth metal carbonates, in particular calcium carbonate, magnesium carbonate and dolomite and hydroxides, in particular brucite (magnesium hydroxide).
  • Suitable co-stabilizers are also polyols, in particular alditols or cyclitols.
  • polyols are pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or short-chain polyester polyols, and hyper-branched polymers/oligomers or dendrimers with alcohol groups, e.g. e.g.:
  • the at least one alditol is preferably selected from the group consisting of threitol, erythritol, galactitol, mannitol, ribitol, sorbitol, xylitol, arabitol, isomalt, lactitol, maltitol, altritol, iditol, maltotritol and hydrogenated oligo- and polysaccharides with polyol - end groups and mixtures thereof.
  • the at least one preferred alditol is particularly preferably selected from the group consisting of erythritol, mannitol, isomalt, maltitol and mixtures thereof.
  • heptitols and octitols meso-glycero-allo-heptitol, D-glycero-D-altro-heptitol, D-glycero-D-manno-heptitol, meso-glycero-gulo-heptitol, D-glycero- D-galacto-heptitol (perseitol), D-glycero-D-gluco-heptitol, L-glycero-D-gluco-heptitol, D-erythro-L-galacto-octitol, D-threo-L-galacto-octitol
  • the at least one cyclitol may be selected from the group consisting of inositol (myo, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi- and cis-inositol), 1,2 ,3,4-tetrahydroxycyclohexane, 1,2,3,4,5-pentahydroxycyclohexane, quercitol, viscumitol, bornesitol, conduritol, ononitol, pinitol, pinpollitol, quebrachitol, ciceritol, quinic acid, shikimic acid and valienol is preferred myo-lnositol (myo-lnositol).
  • inositol myo, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi- and cis-inosito
  • Suitable light stabilizers are compounds based on 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, esters of benzoic acids, acrylates, oxamides and 2-(2-hydroxyphenyl)-1,3,5-triazines.
  • 2-(2'-hydroxyphenyl)benzotriazoles examples include 2-(2'-hydroxy-5'methylphenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole , 2-(5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3 ',5'-Di-tert-butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl-5-chlorobenzotriazole, 2-( 3'-sec-butyl-5'-tert-butyl-2'-hydroxy-phenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazo
  • 2-hydroxybenzophenones 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy -4,4'-dimethyloxy derivatives of 2-hydroxybenzophenones.
  • Suitable acrylates are ethyl ⁇ -cyano- ⁇ , ⁇ -diphenyl acrylate, isooctyl- ⁇ -cyano- ⁇ , ⁇ -diphenyl acrylate, methyl ⁇ -carbomethoxycinnamate, methyl ⁇ -cyano- ⁇ -methyl-p-methoxycinnamate, butyl ⁇ -cyano- ⁇ -methyl-p-methoxycinnamate, methyl ⁇ -carbomethoxy-p-methoxycinnamate and N-( ⁇ -carbo-methoxy- ⁇ -cyanovinyl)-2-methylindoline.
  • esters of benzoic acids are 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, 2-methyl-4,6-di- tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.
  • Suitable oxamides are 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.
  • 2-(2-hydroxyphenyl)-1,3,5-triazines examples include 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy -4-octyloxyphenyl)-4,6- bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6 -bis(4-methyl- phenyl-1,3,5-triazine, 2-(2-Hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethyl- phenyl)-1,
  • suitable metal deactivators are 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 , N,N'-bis(salicyloyl)thiopropionyldihydrazide.
  • metal deactivators are:
  • Suitable low molecular weight hindered amines are 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-hydroxy-benzyl malonate, 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(
  • the structures given above also include the sterically hindered N—H, N-alkyl such as N-methyl or N-octyl, the N-alkoxy derivatives such as N-methoxy or N-octyloxy, and the cycloalkyl derivatives such as N-cyclohexyloxy and the N-(2-hydroxy-2-methylpropoxy) analogs.
  • Preferred hindered amines also have the following structures: ⁇ ⁇
  • Suitable dispersing agents are:
  • 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 e.g. polyethylene block polyethylene oxide
  • dendrimers e.g. dendrimers containing hydroxyl groups .
  • Suitable antinucleating agents are azine dyes such as nigrosine.
  • Suitable flame retardants are, in particular, inorganic flame retardants such as Al(OH)3, Mg(OH)2, AlO(OH), MgCO3, phyllosilicates 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 Sb203, Sb205, Mo03, zinc stannate, zinc hydroxystannate, nitrogen-containing flame retardants such as melamine, Meiern, melam, melon, melamine derivatives, melamine condensation products or melamine salts, benzoguanamine, Polyisocyanurates, allantoin, phosphacene, in particular melamine amine cyanurate, melamine phosphat
  • Radical formers such as e.g. alkoxyamines, hydroxylamine esters, azo compounds, triazene compounds, disulfides, polysulfides, thiols, thiuram sulfides, dithiocarbamates, mercaptobenzothiazoles, sulfenamides, sulfenimides
  • Borates such as zinc borate or calcium borate, optionally on a carrier material such as silica, sulfur-containing compounds such as elemental sulfur, disulfides and polysulfides, thiuram sulfide, dithiocarbamates, mercaptobenzothiazole and sulfenamides,
  • anti-drip agents such as polytetrafluoroethylene, silicon-containing compounds such as polyphenylsiloxanes,
  • Carbon modifications such as carbon nanotubes (CNT), expandable graphite or graphene and combinations or mixtures thereof.
  • plasticizers examples include phthalic acid esters, adipic acid esters, citric acid esters, 1,2-cyclohexanedicarboxylic acid esters, trimellitic acid esters, isosorbide esters, phosphate esters, epoxides such as epoxidized soybean oil or aliphatic polyesters.
  • Suitable lubricants and processing aids are, for example, polyethylene waxes, polypropylene waxes, salts of fatty acids such as calcium stearate, zinc stearate or salts of montan waxes, amide waxes such as erucic acid amide or oleic acid amides, fluoropolymers, silicones or neoalkoxy titanate and zirconates.
  • Suitable pigments can be inorganic or organic in nature.
  • Inorganic pigments are, for example, titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, carbon black, organic pigments are, for example, anthraquinones, anthanthrones, benzimidazolones, quinacridones, diketopyrrolopyrroles, dioxazines, indanthrones, isoindolinones, azo compounds, perylenes, phthalocyanines nine or pyranthrones.
  • Other suitable pigments are metal-based effect pigments or metal-oxide-based pearlescent pigments.
  • Suitable optical brighteners are, for example, bisbenzoxazoles, phenylcoumarins or bis(styryl)biphenyls and in particular optical brighteners of the formulas:
  • Suitable filler deactivators are, for example, polysiloxanes, polyacrylates, in particular block copolymers such as polymethacrylic acid-polyalkylene oxide or polyglycidyl (meth)acrylates and their copolymers, for example with styrene, and epoxides, for example of the following structures:
  • the present invention also relates to use of the stabilizer composition in combination with at least one additive, in particular at least one additive selected from the group consisting of primary antioxidants, secondary antioxidants with the exception of phosphites and phosphonites, UV absorbers , light stabilizers, metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, impact modifiers, lubricants, rheology modifiers, thixotropic agents, chain extenders, processing aids, mold release agents, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents , coupling agents, crosslinking agents, Anticrosslinking agents, hydrophilizing agents, hydrophobicizing agents, adhesion promoters, dispersants, compatibilizers, oxygen scavengers, acid scavengers, blowing agents, degradation additives, defoaming agents, odor scavengers, marking agents, antifo
  • all of the at least one sulfite and/or thiosulfate and all of the at least one polymeric or oligomeric hindered amine in a weight ratio of 1:99 to 99:1, preferably 20:80 to 80:20, more preferably from 30:70 to 70:30, most preferably from 40:60 to 60:40.
  • the present invention also relates to a masterbatch containing 10 to 90% by weight of a stabilizer composition according to one of the two preceding claims, and 90 to 10% by weight of a thermoplastic material, in particular a plastic recyclate, a virgin plastic or a mixture thereof.
  • the present invention relates to a composition, in particular a plastic composition, containing or consisting of
  • a further advantageous embodiment provides that, based on 100 parts by weight of components (A) to (C), up to 80 parts by weight, preferably 0.1 to 60 parts by weight, particularly preferably 1 to 50 parts by weight - Parts of at least one plasticizer, filler and / or reinforcing material is included.
  • the present invention relates to a molding material or a molding that can be produced from a composition according to the invention, in particular in the form of sheets or films, packaging, for example for food or cosmetic products, detergents, cosmetics or adhesives; Hollow bodies, in particular bottles, bags, screw-top cans; Storage and transport containers such. e.g. boxes, crates, barrels, buckets, automotive, railway, aircraft, ship and machine parts such as e.g.
  • Construction applications such as profiles, construction films, roofing membranes, cable ducts, house cladding, noise protection walls, drainage channels, profiled boards, floor coverings, pallets; road and landscaping applications such as beacon bases, posts, barriers, geotextiles; Electrical and electronic applications such as housing parts and accessories for televisions, computers, mobile phones, washing machines, dishwashers, coffee machines, drills, plug connections, storage media; cable insulation;
  • Parts from additive or generative manufacturing processes such as fused layer modeling (FLM), layer laminate modeling (LLM), selective laser sintering (SLS) and other BD printing processes; Pipes for e.g. water, gas, sewage, irrigation, drainage pipes; Hygiene articles such as nappies or as part of disposable nappies, sanitary napkins and tampons; Furniture and textile applications, such as curtains and upholstery, countertops; foams, ribbons, injection molded parts, fibers, and other extrudates; Household, leisure and sporting goods such as balls, tennis rackets, skis, flower pots, water butts, clothes hangers; agricultural applications such as greenhouse, mulch, tunnel or perforated films, plant pots, membranes such as geomembranes;
  • FLM fused layer modeling
  • LLM layer laminate modeling
  • SLS selective laser sintering
  • Pipes for e.g. water, gas, sewage, irrigation, drainage pipes
  • Hygiene articles such as nappies or as part of disposable nappies, sanitary napkins
  • the present invention relates to a method for the oxidative, thermal and/or actinic stabilization of a thermoplastic material, in particular against oxidative, thermal and/or actinic degradation, by adding, adding additives or incorporating at least one stabilizer composition according to the invention to or .into the plastic.
  • the additive combination according to the invention which can be present as a powder, liquid, oil, compacted, on a carrier material, as granules, solution or flakes, is preferably mixed with the polymer to be stabilized, the polymer matrix is melted and then cooled. Alternatively, it is also possible to introduce one or more additives into a polymer melt in a molten state.
  • polymer composition can be added to the polymers separately, in the form of liquids, powders, granules or compacted products, or together with the additive composition according to the invention as described above.
  • the additive composition described above and any additional additives are incorporated into the plastic using customary processing methods, preferably using mixers, kneaders or extruders.
  • Extruders such as single-screw extruders, twin-screw extruders, planetary roller extruders, ring extruders, co-kneaders, which are preferably equipped with vacuum degassing, are preferred as processing machines.
  • the processing can take place under air or optionally under inert gas conditions.
  • a further aspect of the present invention relates to the use of the composition according to the invention described above for the production of sheets or films, packaging, for example for food or cosmetic products, detergents, cosmetics or adhesives; Hollow bodies, in particular bottles, bags, screw-top cans; Storage and transport containers such. B.
  • Construction applications such as profiles, construction films, roofing membranes, cable ducts, house cladding, noise protection walls, drainage channels, profile boards, floor coverings, pallets; road and landscaping applications such as beacon bases, posts, barriers, geotextiles; Electrical and electronic applications such as housing parts and accessories for televisions, computers, mobile phones, washing machines, dishwashers, coffee machines, drills, plug connections, storage media; cable insulation; Parts from additive or generative manufacturing processes such as fused layer modeling (FLM), layer laminate modeling (LLM), selective laser sintering (SLS) and other SD printing processes; Pipes for eg water, gas, waste water, irrigation, drainage pipes; Hygiene articles such as diapers or as part of disposable diapers, sanitary towels and tampons; Furniture and textile applications such as curtains and upholstery, countertops; foams, ribbons, injection molded parts, fibers, and other extrudates; Household
  • agricultural applications such as greenhouse, mulch, tunnel or perforated films, plant pots, membranes such as geomembranes;
  • Pharmaceutical and crop protection applications such as encapsulation of active ingredients and biologically active substances; as well as sutures, bandages, orthoses and prostheses.
  • a good stabilizing effect can be achieved with combinations of hindered amines and inorganic sulfites, and the hindered amine can be partially replaced by inexpensive sulfites.
  • New stabilizer compositions and a new process for stabilizing plastics in particular, which are highly effective, environmentally friendly and have a favorable cost structure, are being developed.

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EP22710988.1A 2021-03-04 2022-03-01 Verwendung einer stabilisatorzusammensetzung zur stabilisierung von organischen materialien, stabilisatorzusammensetzung, masterbatch, zusammensetzung, formmasse der formteile, verfahren zur oxidativen, thermischen aktinischen stabilisierung eines thermoplastischen kunststoffs sowie verwendung einer zusammensetzung Pending EP4301810A1 (de)

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PCT/EP2022/055094 WO2022184687A1 (de) 2021-03-04 2022-03-01 Verwendung einer stabilisatorzusammensetzung zur stabilisierung von organischen materialien, stabilisatorzusammensetzung, masterbatch, zusammensetzung, formmasse der formteile, verfahren zur oxidativen, thermischen aktinischen stabilisierung eines thermoplastischen kunststoffs sowie verwendung einer zusammensetzung

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