EP4126810A1 - Utilisation d'esters d'acide cinnamique substitués en tant que stabilisants pour des matériaux organiques, matériau organique stabilisé, procédé de stabilisation de matériaux organiques et esters d'acide cinnamique spécifiques - Google Patents

Utilisation d'esters d'acide cinnamique substitués en tant que stabilisants pour des matériaux organiques, matériau organique stabilisé, procédé de stabilisation de matériaux organiques et esters d'acide cinnamique spécifiques

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Publication number
EP4126810A1
EP4126810A1 EP21713654.8A EP21713654A EP4126810A1 EP 4126810 A1 EP4126810 A1 EP 4126810A1 EP 21713654 A EP21713654 A EP 21713654A EP 4126810 A1 EP4126810 A1 EP 4126810A1
Authority
EP
European Patent Office
Prior art keywords
styrene
alcohol
group
tert
butyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21713654.8A
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German (de)
English (en)
Inventor
Rudolf Pfaendner
Jannik MAYER
Elke Metzsch-Zilligen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
Original Assignee
Fraunhofer Gesellschaft zur Forderung der Angewandten Forschung eV
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Publication of EP4126810A1 publication Critical patent/EP4126810A1/fr
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
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
    • C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/372—Sulfides, e.g. R-(S)x-R'
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C08L23/12—Polypropene

Definitions

  • the present invention relates to the use of specific cinnamic acid esters as stabilizers of organic materials, in particular against oxidative, thermal and / or actinic degradation.
  • the present invention also relates to a correspondingly stabilized organic material.
  • Another aspect of the present invention relates to a method for stabilizing organic materials, in which specific cinnamic acid esters are incorporated into the organic material.
  • Specific new cinnamic acid esters are also disclosed in accordance with the invention.
  • Organic materials such as plastics are subject to aging processes, which ultimately lead to a loss of the desired properties such as the mechanical parameters.
  • This process known as autoxidation, leads to changes in the polymer chain, such as in the molecular weight or the formation of new chemical groups, based on radical chain cleavages through mechanochemical processes or through UV radiation in the presence of oxygen.
  • Stabilizers are therefore used to at least delay the process.
  • Important representatives of stabilizers are antioxidants, which interfere with the radicals formed during autoxidation and thus interrupt the breakdown process.
  • primary antioxidants which can react directly with oxygen-containing free radicals or C-radicals
  • secondary antioxidants which react with intermediate hydroperoxides (see C.
  • phenols with an anti-oxidative effect in plastics are, for example, quercetin (B. Kirschweng et al., Eur. Pol. J. 2018, 103, 228-237), Dihydromyrecetin (B. Kirschweng et al., Pol. Degr. Stab. 2016, 133, 192-200), derivatives of rosmarinic acid. (K. Doudin et al., Pol. Degr. Stab. 2016, 130, 126-134) or also tannin (WJ Grigsby et al., Polymers 5 (2013) 344-360). Furthermore, derivatives of ferulic acid (AF Reano et al.
  • Ferulic acid and its salts are used, for example, in the cosmetics industry or as active pharmaceutical ingredients (e.g. FR 2907338, CN 101181256, DE 1957433), the production of the salts is known in principle (e.g. AT 317184).
  • the state of the art is also the stabilization of plastics with selected ester derivatives of ferulic acid (AF Reano et al. ACS Sustainable Chemistry and Engineering 4 (2015), 6562 ⁇ 6571, AF Reano et al. ACS Sustainable Chemistry and Engineering 3 (2015) , 3486-3496) and caffeic acid (V. Ambrogi et al. Biomacromolecules 15 (2014), 302-310).
  • these derivatives are relatively laboriously produced by enzymatic syntheses.
  • ferulic acid derivatives in the form of ester compounds are isosorbide esters (US 2007 189990), cholestanyl esters (WO 2018/153917) and oligomers and polymers of ferulic acid (US 2016 257846).
  • the object of the present invention was to provide sustainable antioxidants for plastics based on renewable raw materials with high effectiveness, high thermal stability and low volatility.
  • the present invention thus relates in a first aspect to the use of a compound or mixtures of several compounds according to general formula I formula I.
  • R 1 , R 2 and R 3 are each independently selected from the group consisting of hydroxy, linear or branched alkoxy groups with 1 to 6 carbon atoms and hydrogen, with the proviso that at least one of the radicals R 1 , R 2 and R 3 is a hydroxy radical and / or a linear or branched alkoxy group with 1 to 6 carbon atoms, and R 4 is selected from the group consisting of a linear or branched alkyl radical with at least 8 carbon atoms and the following radicals according to formulas IIa, IIb and IIc, Formula IIa Formula IIb Formula IIc where R 5 is identical or different on each occurrence and is selected from the group consisting of hydroxy and the following radical according to formula III, where R 1 , R 2 and R 3 are as defined above, for the stabilization of organic materials, in particular against oxidative, thermal and / or actinic degradation.
  • the cinnamic acid derivatives used according to the invention can be used as new stabilizers based on renewable raw materials.
  • a high level of effectiveness, environmental friendliness and a favorable cost structure compared to the stabilizers known from the prior art were found.
  • Particularly suitable organic materials for the purposes of the present invention are plastics, coatings, lubricants, hydraulic oils, engine oils, turbine oils, gear oils, metal working fluids, chemicals or monomers. According to the invention, cosmetics are not counted among the organic materials.
  • the compound according to general formula I is selected from the group consisting of the following compounds: wherein R 4 is as defined in claim 1.
  • the linear or branched alkyl radical with at least 8 Carbon atoms of the radical R 4 of alcohols selected from the group consisting of octan-1-ol, nonan-1-ol, decan-1-ol, undecan-1-ol, lauryl alcohol, tridecan-1-ol, myristyl alcohol, cetyl alcohol, Stearyl alcohol, ceryl alcohol, myricyl alcohol, palmitoleyl alcohol, oleyl alcohol, arachidyl alcohol, behenyl alcohol, erucyl alcohol, lignoceryl alcohol, montanyl alcohol, linoleyl alcohol, isotridecyl alcohol, geraniol, rhodinool, citronellearol and lauryl alcohol are particularly preferred.
  • Preferred radicals R 5 are selected from the group consisting of the following radicals. It is particularly preferred here that the substitution pattern of the remainder according to of the compound according to formula I and the substitution pattern of the radical R 5 is identical. This means that, for example, the substitution pattern of the radicals according to formula IIa, IIb, IIc with respect to R 5 and the cinnamic acid radical according to formula I is identical. Such connections are thus symmetrical.
  • the compound according to general formula I or, in the case of a mixture of several compounds according to general formula I, is preferably the All of the compounds according to general formula I in a proportion by weight of 0.01 to 10.00% by weight, preferably 0.02 to 5.00% by weight, particularly preferably 0.05 or 0.10 to 2, 00% by weight contained in the organic material.
  • the compound according to formula I or the mixtures thereof is used to stabilize thermoplastic, elastomeric or thermoset plastics.
  • 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 esters 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 an
  • graft copolymers such as styrene on butadiene, maleic anhydride on SBS or SEBS, as well as graft copolymers made of methyl methacrylate, styrene-butadiene and ABS (MABS), as well as hydrogenated polystyrene derivatives
  • halogen-containing polymers such as polyvinyl 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 thereof
  • PMMA polymethyl methacrylate
  • PMMA polybutyl acrylate
  • polylauryl acrylate polystearyl acrylate
  • polystyrene resin made 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 j) polyimides, polyamide ⁇ imides, polyetherimides, polyesterimides, poly ⁇ (ether) ketones, polysulfones, polyether sulfones, polyarylsulfones, poly ⁇ phenylene sulfides, polybenzimidazoles, polyhydantoins, k) polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxy ⁇ carboxylic acids such as polyethylene terephthalate (PET), polybutylene terephthal
  • polymers specified under a) to r) are copolymers, they can be in the form of statistical (“random”), block or “tapered” structures. Furthermore, the polymers mentioned can be in the form of linear, branched, star-shaped or hyperbranched structures. If the polymers specified under a) to r) are stereoregular polymers, they can be 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.
  • the polyolefins mentioned under a) can also be crosslinked, e.g. crosslinked polyethylene, which is then referred to as X ⁇ PE.
  • the present compounds can also be used to stabilize rubbers and elastomers.
  • NR natural rubber
  • synthetic rubber materials such as NR (Natural Rubber), chloroprene (CR), polybutadiene (BR), styrene-butadiene (SBR), Polyisoprene (IR), butyl rubber (IIR), nitrile rubber (NBR), hydrogenated nitrile rubber (HNBR), polyester or polyether urethane rubber, silicone rubber.
  • NR Natural Rubber
  • CR chloroprene
  • BR polybutadiene
  • SBR styrene-butadiene
  • IR butyl rubber
  • NBR nitrile rubber
  • HNBR hydrogenated nitrile rubber
  • polyester or polyether urethane rubber silicone rubber.
  • the plastics can be recycled plastics e.g. B. from industrial collections such as production waste or plastics from household or recyclable materials collections.
  • Preferred plastics are thermoplastic plastics and, in particular, plastics which are used in packaging such as, for example, food packaging, in particular polyolefins, polystyrene, polyesters and polyamides.
  • Polypropylene homo ⁇ and copolymers, as well as polyethylene in the form of LDPE, LLDPE, HDPE, MDPE, VLDPE and polyethylene terephthalate (PET), homo ⁇ and copolymers are very particularly preferred.
  • aliphatic polyesters from renewable raw materials which are essentially produced from aliphatic dicarboxylic acids and aliphatic diols, from hydroxycarboxylic acids or lactones.
  • the plastic can contain at least one further additive selected from the group consisting of primary and / or secondary antioxidants, in particular primary and / or secondary antioxidants selected from the group consisting of phosphites, phosphonites, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines and Mixtures or combinations thereof, 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,
  • an additive or several additives are contained in the plastic, these are preferably in total in an amount of 0.01 to 9.99% by weight, preferably 0.01 to 4.98% by weight, particularly preferably 0.02 to 2.00% by weight, based on the totality of the at least one compound according to formula I, of the organic material and of the at least one additive, contain or are added when used.
  • the present invention also relates to an organic material, in particular a plastic composition, containing at least one compound according to general formula I or a mixture of several compounds according to general formula I as a stabilizer
  • the organic material preferably has the following composition:
  • the at least one additive is selected from the group consisting of primary and / or secondary antioxidants, in particular primary and / or secondary antioxidants selected from the group consisting of phosphites, phosphonites, thiols, phenolic antioxidants, sterically hindered amines, hydroxylamines as well as mixtures or combinations thereof, UV absorbers, light stabilizers, hydroxylamine-based stabilizers, benzofuran-based stabilizers, nucleating agents, impact strength improvers, plasticizers, lubricants, rheology modifiers, chain extenders, processing aids, pigments, dyes, optical brighteners, antimicrobials, Antistatic agents, slip agents, antiblocking agents, coupling agents, dispersants, compatibilizers, oxygen scavengers, acid scavengers, costabilizers, marking agents and anti-fogging agents; is selected in particular from the group consisting of a secondary antioxidant selected from the group consisting of phosphites, phosphonites,
  • Suitable primary antioxidants (A) are phenolic antioxidants, amines and lactones.
  • Suitable synthetic phenolic antioxidants are, for example: 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- ( ⁇ -methylcyclohexyl ) -4,6-dimethylphenol, 2,6-dioctadecyl-4- methylphenol, 2,4,6 ⁇ tricyclohexylphenol, 2,6 ⁇ di ⁇ tert ⁇ butyl ⁇ 4 ⁇ me
  • octane 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-hydroxyphenyl) propionic acid, such as N
  • Other particularly preferred phenolic antioxidants are based on renewable raw materials such as. B.
  • tocopherols vitamin E
  • tocotrienols tocomonoenols
  • carotenoids hydroxytyrosol
  • flavonols such as chrysin, quercitin, hesperidin, neohesperidin, naringin, morin, kaempferol, fisetin, Anthocyanins such as delphinidin and malvidin, curcumin, carnosic acid, carnosol, rosmarinic acid and resveratrol.
  • Suitable aminic antioxidants are, for example: N, N'-di-isopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylenediamine, N, N'-bis (1,4-dimethylpentyl) -p- phenylenediamine, N, N'-bis (1-ethyl-3-methyl-pentyl) -p-phenylenediamine, N, N'-bis (1-methylheptyl) -p-phenylenediamine, N, N'-dicyclohexyl-p-phenylenediamine , N, N'-diphenyl-p-phenylenediamine, N, N'-bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N- (1,3-dimethylbutyl) -N
  • Preferred aminic antioxidants are: N, N'-di-isopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylenediamine, N, N'-bis (1,4-dimethylpentyl) -p-phenylenediamine , N, N'-bis (1-ethyl-3-methylpentyl) -p-phenylenediamine, N, N'-bis (1-methylheptyl) -p-phenylenediamine, N, N'- Dicyclohexyl-p-phenylenediamine, N, N'-diphenyl-p-phenylenediamine, N, N'-bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N- (1 , 3-dimethylbutyl) -N'-phenyl
  • Suitable secondary antioxidants are also organosulfur compounds such as sulfides and disulfides, for example distearyl thiodipropionate, dilauryl thiodipropionate; Ditridecyldithiopropionate, ditetradecylthiodipropionate, 3 ⁇ (dodecylthio) -, 1,1 '- [2,2 ⁇ bis [[3 ⁇ (dodecylthio) -1 ⁇ oxopropoxy] methyl] -1,3-propanediyl] propanoic acid ester.
  • organosulfur compounds such as sulfides and disulfides, for example distearyl thiodipropionate, dilauryl thiodipropionate; Ditridecyldithiopropionate, ditetradecylthiodipropionate, 3 ⁇ (dodecylthio) -, 1,1 '
  • Suitable acid scavengers are salts of one, two, three or four-valent metals, preferably alkali metals, alkaline earth metals, aluminum or zinc, in particular formed 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, especially synthetic hydrotalcites based on aluminum, magnesium and zinc, hydrocalumites, zeolites, alkaline earth oxides, especially calcium oxide and magnesium oxide and zinc oxide, alkaline earth carbonates, especially calcium carbonate, magnesium carbonate and dolomite, and hydroxides, especially brucite (magnesium hydroxide),
  • Suitable costabilizers are also polyols, in particular alditols or cyclitols.
  • Polyols are, for example, pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or polyester polyols, and hyperbranched polymers / oligomers or dendrimers with alcohol groups, for example
  • 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 can 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, myo ⁇ inositol is preferred ( myo-inositol).
  • Suitable light stabilizers are, for example, compounds based on 2 ⁇ (2'-hydroxyphenyl) benzotriazoles, 2-hydroxybenzophenones, esters of benzoic acids, acrylates, oxamides and 2- (2-hydroxyphenyl) -1,3,5-triazines.
  • Suitable 2- (2'-hydroxyphenyl) benzotriazoles are, for example, 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'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-4'-octyloxyphenyl) benzotriazo
  • 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'-dimethoxy derivatives of 2-hydroxybenzo ⁇ phenones.
  • Suitable acrylates are, for example, 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- ( ⁇ -carbomethoxy- ⁇ -cyanovinyl) -2-methylindoline.
  • Suitable esters of benzoic acids are, for example, 4 ⁇ tert ⁇ butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4 ⁇ tert ⁇ butylbenzoyl) resorcinol, benzoyl resorcinol, 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, for example, 4,4'-dioctyloxyoxanilide, 2,2'-diethoxy-oxanilide, 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.
  • Suitable 2 ⁇ (2 ⁇ hydroxyphenyl) ⁇ 1,3,5 ⁇ triazines are, for example, 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-dodecy
  • Suitable metal deactivators are, 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) oxalyl dihydrazide, Oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenyl hydrazide, N, N'-diacetyladipoyl dihydrazide, N, N'-bis (salicyloyl) oxylyldihydrazide, N, N'-bis (salicyloyl) thiopropionyl dihydrazide.
  • Suitable hindered amines are, for example, 1,1-bis (2,2,6,6-tetramethyl-4-piperidyl) succinate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, 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,
  • N-H sterically hindered N-H, N-alkyl such as N-methyl or N-octyl, the N-alkoxy derivatives such as N-methoxy or N-octyloxy, the cycloalkyl derivatives such as N-cyclohexyloxy and the N- (2-hydroxy-2- methylpropoxy) analogs.
  • Preferred hindered amines also have the following structures:
  • Preferred oligomeric and polymeric hindered amines have the following structures: In the case of the compounds mentioned above, n is in each case 3 to 100.
  • Suitable light stabilizer is Hostanox NOW (manufacturer: Clariant SE) with the following general structure: where R -O-C (O) -C 15 H 31 or -O-C (O) -C 17 H 35 means.
  • Suitable dispersants are, 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.
  • acrylic polypropylene co-polymers Polypropylene-co-maleic anhydride, polyethylene-co-glycidyl methacrylate, polystyrene-old-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.
  • Suitable anti-nucleating agents are azine dyes such as nigrosine.
  • Suitable flame retardants are in particular a) inorganic flame retardants such as Al (OH) 3 , Mg (OH) 2 , AIO (OH), MgCO 3 , sheet 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 Sb 2 O 3 , Sb 2 O 5 , MoO 3 , 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 pyrophosphat
  • Suitable plasticizers are, for example, phthalic acid esters, adipic acid esters, esters of citric acid, esters of 1,2-cyclohexanedicarboxylic acid, 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 titanates 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, phthaloneocyanines or pyranthroneocyanines.
  • Other suitable pigments are effect pigments based on metal or pearlescent pigments based on metal oxide.
  • 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, e.g. with styrene, and epoxides e.g.
  • Suitable antistatic agents are, for example, ethoxylated alkylamines, fatty acid esters, alkyl sulfonates and polymers such as, for example, polyetheramides.
  • Suitable antiozonants are the above-mentioned amines such as N, N'-di ⁇ isopropyl-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,
  • Suitable additives for increasing the molecular weight of polycondensation polymers are diepoxides, bis-oxazolines, bis-oxazolones, bis-oxazines, diisocyanates, dianhydrides, bis-acyl lactams, bis-maleimides, dicyanates, carbodiimides.
  • Further suitable chain extenders are polymeric compounds such as polystyrene-polyacrylate-polyglycidyl (meth) acrylate copolymers, polystyrene-maleic anhydride copolymers and polyethylene-maleic anhydride copolymers.
  • Suitable additives for increasing electrical conductivity are, for example, the aforementioned antistatic agents, soot and carbon compounds such as carbon nanotubes and graphene, metal powder such as copper powder and conductive polymers such as Polypyrroles, polyanilines and polythiophenes.
  • Suitable additives for increasing the thermal conductivity are, for example, aluminum nitrides and boron nitrides.
  • Suitable infrared active additives are, for example, aluminum silicates, hydrotalcites or dyes such as phthalocyanines or anthraquinones.
  • Suitable mold release agents are, for example, silicones, soaps and waxes such as, for example, montan waxes.
  • the additives according to the invention can also be used to stabilize oils, fats and chemical products.
  • the organic materials are oils and fats, these can be based on mineral oils, vegetable fats or animal fats or oils, fats or waxes based on, for example, synthetic esters.
  • Vegetable oils and fats are, for example, palm oil, olive oil, rapeseed oil, linseed oil, soybean oil, sunflower oil, castor oil, animal fats are, for example, fish oils or beef tallow.
  • the compounds according to the invention can also be used as stabilizers for lubricants, hydraulic oils, motor oils, turbine oils, gear oils, metal working fluids or as lubricating greases. These mineral or synthetic lubricants are mainly based on hydrocarbons.
  • Chemical products are used, for example, to stabilize polyols used for the production of polyurethanes or to stabilize monomers such as styrene, acrylic esters, methacrylic esters during transport and storage.
  • the present invention also relates to a method for stabilizing organic materials, in particular against oxidative, thermal and / or actinic degradation, in which one or more compounds according to general formula I Formula I where R 1 , R 2 , R 3 and R 4 are as defined in one of Claims 1 and 5, is incorporated into the organic material. All preferred statements relating to the compound according to general formula I as formulated above also apply without restriction to the process according to the invention.
  • the invention also relates to compounds according to general formula I.
  • R 1 , R 2 and R 3 are each independently selected from the group consisting of hydroxyl, linear or branched alkoxy groups with 1 to 6 carbon atoms and hydrogen, with the proviso that at least one of the radicals R 1 , R 2 and R 3 is a hydroxy radical and / or a linear or branched alkoxy group with 1 to 6 carbon atoms, and the following radicals according to formulas IIa, IIb and IIc Formula IIa Formula IIb Formula IIc where R 5 is identical or different on each occurrence and is selected from the group consisting of hydroxy and the following radical according to Formula III where R 1 , R 2 and R 3 are as defined above.
  • additive compositions according to the invention can be produced and introduced in the form of so-called masterbatches or concentrates, which contain, for example, 10-90% of the additives according to the invention in a polymer.
  • Fields of application according to the invention for the stabilization or organic materials according to the invention are in particular plastics in the form of injection molded parts, foils or films, foams, fibers, cables and pipes, profiles, hollow bodies, tapes, membranes, such as geomembranes, or adhesives that are produced via extrusion, injection molding , Blow molding, calendering, pressing processes, spinning processes, rotomoulding are manufactured e.g.
  • DBTO dibutyltin oxide
  • 0.15 g (0.04 eq., 0.60 mmol) of dibutyltin oxide (DBTO) are added to the clear melt in a countercurrent of nitrogen.
  • the reaction temperature is increased to 140 ° C and a pressure between 200-800 mbar is set.
  • the excess stearyl alcohol is condensed off by increasing the temperature to 155 ° C and reducing the pressure to 1 ⁇ 10 ⁇ 3 bar.
  • the vacuum is broken by the introduction of nitrogen and the slightly yellowish Reaction melt cooled to room temperature. This is then taken up in dichloromethane, 2.80 g of fuller's earth (OPTIMUM 21OFF) are added and the mixture is refluxed for 30 min.
  • the reaction temperature is increased to 170 ° C and a pressure between 600-800 mbar is set.
  • the excess methyl ferulate is condensed off by setting the temperature to 155 ° C and reducing the pressure to 1 ⁇ 10 -3 bar.
  • the vacuum is broken by the introduction of nitrogen and the yellow reaction melt is cooled to room temperature. This is then taken up in dichloromethane, treated with 2.80 g of fuller's earth (OPTIMUM 21OFF) and refluxed for 30 min. After filtration through a short silica pad, the solvent is distilled off in vacuo. There remain 10.02 g (11.92 mmol, 81.12%) of the finely powdered, yellow solid.

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
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Abstract

La présente invention concerne l'utilisation d'esters d'acide cinnamique spécifiques en tant que stabilisants de matériaux organiques, en particulier contre la dégradation oxydative, thermique et/ou actinique. L'invention concerne également un matériau organique stabilisé correspondant. L'invention concerne en outre un procédé de stabilisation de matériaux organiques, selon lequel des esters d'acide cinnamique spécifiques sont incorporés dans le matériau organique. L'invention concerne également de nouveaux esters d'acide cinnamique spécifiques.
EP21713654.8A 2020-03-27 2021-03-19 Utilisation d'esters d'acide cinnamique substitués en tant que stabilisants pour des matériaux organiques, matériau organique stabilisé, procédé de stabilisation de matériaux organiques et esters d'acide cinnamique spécifiques Pending EP4126810A1 (fr)

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DE102020203987.9A DE102020203987A1 (de) 2020-03-27 2020-03-27 Verwendung von substituierten Zimtsäureestern als Stabilisatoren für organische Materialien, tabilisiertes organisches Material, Verfahren zur Stabilisierung von organischen Materialien sowie spezifische Zimtsäureester
PCT/EP2021/057101 WO2021191078A1 (fr) 2020-03-27 2021-03-19 Utilisation d'esters d'acide cinnamique substitués en tant que stabilisants pour des matériaux organiques, matériau organique stabilisé, procédé de stabilisation de matériaux organiques et esters d'acide cinnamique spécifiques

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DE102021212696A1 (de) 2021-11-11 2023-05-11 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Stabilisatoren auf Basis von Syringasäure, Vanillinsäure, lsovanillinsäure oder 5-Hydroxyveratrumsäure, Kunststoffzusammensetzung, Verfahren zur Stabiliserung einer Kunststoffzusammensetzung sowie Stabilisatorzusammensetzung
DE102022201632A1 (de) 2022-02-16 2023-08-17 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein Polymere Stabilisatoren auf Basis von Syringasäure, Vanillinsäure, lsovanillinsäure oder 5-Hydroxyveratrumsäure, Kunststoffzusammensetzung, Verfahren zur Stabiliserung einer Kunststoffzusammensetzung sowie Stabilisatorzusammensetzung

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DE1957433A1 (de) 1969-11-14 1971-05-27 Pluripharm Sarl Neue Zimtsaeurederivate und Verfahren zu ihrer Herstellung
AT317184B (de) 1969-11-19 1974-08-12 Pluripharm Sarl Verfahren zur Herstellung von neuen Zimtsäuresalzen
KR19980048361A (ko) * 1996-12-17 1998-09-15 손욱 광배향성 조성물, 이로부터 형성되는 배향막과 이 배향막을 구비한 액정표시소자
DE10058290A1 (de) * 2000-11-23 2002-05-29 Basf Ag Verfahren zur Stabilisierung von Polyolefinen
US6919473B2 (en) * 2002-09-17 2005-07-19 Cph Innovations Corporation Photostabilizers, UV absorbers, and methods of photostabilizing a sunscreen composition
US20070189990A1 (en) 2006-02-16 2007-08-16 Anthony East Ultraviolet absorber for cosmetics and polymeric materials
FR2907338B1 (fr) 2006-10-20 2020-01-10 Greentech Utilisation de l'acide ferulique dans le domaine cosmetique et/ou pharmaceutique
CN100574752C (zh) 2007-11-29 2009-12-30 中山大学 一种防治缺血性脑血管疾病的药物组合物及其制备方法
FR3011841B1 (fr) 2013-10-14 2016-09-16 Agronomique Inst Nat Rech Polymere phenolique a liaisons biaryles 5-5, procede pour sa preparation et utilisations
DE102014211276A1 (de) * 2014-06-12 2015-12-17 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung von Hydroxybenzotriazol-Derivaten und/oder Hydroxy-Indazol-Derivaten als Flammschutzmittel für Kunststoffe sowie flammgeschützte Kunststoffformmasse
WO2016141314A2 (fr) * 2015-03-04 2016-09-09 Hallstar Innovations Corp. Compositions photostables comprenant des dérivés d'acide propénoïque substitué par para-alcoxylphényle (app)
EP3309215B1 (fr) * 2015-06-12 2019-07-24 Mitsubishi Chemical Corporation Composition de résine, film l'utilisant et structure multicouche
US11091611B2 (en) 2017-02-23 2021-08-17 Sabic Global Technologies B.V. Polyolefin composition

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US20230117792A1 (en) 2023-04-20
WO2021191078A1 (fr) 2021-09-30

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