EP3870641A1 - Verfahren zur stabilisierung von thermoplastischer kunststoffneuware sowie stabilisierte kunststoffzusammensetzungen, hieraus hergestellte formmassen und formteile, stabilisator-zusammensetzungen sowie verwendungen hiervon - Google Patents
Verfahren zur stabilisierung von thermoplastischer kunststoffneuware sowie stabilisierte kunststoffzusammensetzungen, hieraus hergestellte formmassen und formteile, stabilisator-zusammensetzungen sowie verwendungen hiervonInfo
- Publication number
- EP3870641A1 EP3870641A1 EP19802078.6A EP19802078A EP3870641A1 EP 3870641 A1 EP3870641 A1 EP 3870641A1 EP 19802078 A EP19802078 A EP 19802078A EP 3870641 A1 EP3870641 A1 EP 3870641A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- agents
- styrene
- acid
- butyl
- thermoplastic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 229950000688 phenothiazine Drugs 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 1
- QVJYHZQHDMNONA-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1 QVJYHZQHDMNONA-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- LRGQZEKJTHEMOJ-UHFFFAOYSA-N propane-1,2,3-triol;zinc Chemical compound [Zn].OCC(O)CO LRGQZEKJTHEMOJ-UHFFFAOYSA-N 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940043175 silybin Drugs 0.000 description 1
- 235000014899 silybin Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- FQZYTYWMLGAPFJ-OQKDUQJOSA-N tamoxifen citrate Chemical compound [H+].[H+].[H+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 FQZYTYWMLGAPFJ-OQKDUQJOSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- GTYPQEYBVXUWBY-UHFFFAOYSA-N tert-butyl 2-[(4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound C(C)(C)(C)OC(CSCC1=CC=C(C=C1)O)=O GTYPQEYBVXUWBY-UHFFFAOYSA-N 0.000 description 1
- IKOVHYUZRSZDRL-UHFFFAOYSA-N tert-butyl 2-benzylsulfanylacetate Chemical compound CC(C)(C)OC(=O)CSCC1=CC=CC=C1 IKOVHYUZRSZDRL-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- VLCLHFYFMCKBRP-UHFFFAOYSA-N tricalcium;diborate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]B([O-])[O-].[O-]B([O-])[O-] VLCLHFYFMCKBRP-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- WMXBGWKUWMQWAL-UHFFFAOYSA-H trizinc 1,3,5-triazine-2,4,6-triamine diphosphate Chemical compound N1=C(N)N=C(N)N=C1N.P(=O)([O-])([O-])[O-].[Zn+2].P(=O)([O-])([O-])[O-].[Zn+2].[Zn+2] WMXBGWKUWMQWAL-UHFFFAOYSA-H 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- OXQKEKGBFMQTML-KVTDHHQDSA-N volemitol Chemical compound OC[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H](O)CO OXQKEKGBFMQTML-KVTDHHQDSA-N 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- 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
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
-
- 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
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- 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
- C08K5/13—Phenols; Phenolates
-
- 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
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered rings
-
- 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
- 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
- C08K3/014—Stabilisers against oxidation, heat, light or ozone
Definitions
- the present invention relates to a method for stabilizing new thermoplastic synthetic material against oxidative, thermal and / or actinic degradation.
- the method according to the invention at least one polyphenol and at least one alditol and / or cyclitol are introduced into a new thermoplastic material.
- the process according to the invention can be used to stabilize new thermoplastic material with high effectiveness and in a very environmentally friendly and cost-effective manner against oxidative, thermal and / or actinic degradation.
- the present invention also relates to appropriately stabilized new thermoplastic synthetic material and to molding compositions and molded parts produced therefrom.
- the present invention also relates to stabilizer compositions and their use for stabilizing new thermoplastic plastic against oxidative, thermal and / or actinic degradation.
- Organic materials such as plastics are subject to aging processes, which ultimately lead to a loss of the desired properties, e.g. of the mechanical parameters.
- This process leads to changes in the polymer chain starting from radical chain splitting by mechanochemical processes or by UV radiation in the presence of oxygen, e.g. in molecular weight or the formation of new chemical groups.
- Stabilizers are therefore used to prevent or at least delay this aging.
- Important representatives of stabilizers are antioxidants, which interfere with the radicals formed in the autoxidation and thus interrupt the degradation process.
- primary antioxidants that can react directly with oxygen-containing free radicals or C radicals and secondary antioxidants that react with intermediate hydroperoxides (see C. Kröhnke et al.
- Typical representatives of primary antioxidants are, for example, phenolic antioxidants, amines but also lactones.
- Classes of secondary antioxidants are phosphorus compounds such as Phosphites and phosphonites, but also organosulfur compounds such as Sulfides and disulfides. In practice, primary and secondary antioxidants are usually combined, which leads to a synergistic effect.
- Plastics made from fossil raw materials such as petroleum or natural gas are increasingly being supplemented or replaced by plastics based on renewable raw materials, accessible through biochemical processes.
- the primary and secondary antioxidants used for this (and for plastics made from fossil raw materials) are still not entirely based on renewable raw materials.
- primary antioxidants from renewable raw materials are known, which are also used occasionally in plastics.
- a typical example is tocopherols (vitamin E).
- Tocopherols have the usual tioxidants have a sterically hindered phenol structure and can be used alone or in combination with secondary antioxidants (eg S. Al-Malaika, Macromol. Symp. 2001, 176, 107).
- Tocopherols can e.g. be isolated from natural substances such as wheat germ oil, sunflower oil or olive oil.
- secondary antioxidants, ie phosphite or phosphonite structures cannot be found in nature, so that synergistic combinations of primary and secondary antioxidants from renewable raw materials have so far hardly been accessible.
- a method for stabilizing new thermoplastic plastic against oxidative, thermal and / or actinic degradation is thus specified, in which at least one polyphenol (hereinafter also referred to as “component (A)”) and at least one alditol and / or cylitol (hereinafter also referred to as “components (B)”) is introduced into a new thermoplastic material.
- component (A) polyphenol
- components (B) alditol and / or cylitol
- the plastics to be stabilized can be based on fossil fuels Raw materials or made from renewable raw materials.
- New thermoplastic materials are not yet used, i. H. plastic material that has not yet been used.
- Corresponding new plastic material is also referred to in English as “virgin resin” or "pristine resin”.
- New plastics can also be called “new plastics” or “brand new plastics”.
- the new plastic material can be present, for example, as fresh plastic granulate or plastic powder, or also as a plastic melt that occurs during the manufacturing process. New plastic goods are therefore different from recycled plastics.
- plastic new goods In contrast to plastic recyclates, plastic new goods mostly show no or no significant pre-damage, ie there are no or only very minor new chemical groups on the polymer chain created by oxidative or (photo) oxidative processes.
- polyolefin recyclates for example, these are predominantly carbonyl groups, which are not present in new goods or are only present to a very minor extent.
- concentration of acid groups which are not or only to a minor extent found in new goods, while recyclates have a significant concentration.
- the concentration of the carbonyl groups is therefore also a measure of the pre-damage to the polymer.
- the concentration of carbonyl groups can be determined by known analytical methods such as infrared spectroscopy, as described, for example, in E. Richaud et al. Pole. Degr. Rod. 2009, 94, 410-420. Here, the absorption of the carbonyl vibration is measured in the range of 1720 cm 1 . In the case of new goods, the concentration of carbonyl groups is generally below 5 mmol / kg, the concentration of acid groups below 2 mmol / kg.
- the at least one polyphenol (component (A)) and the at least one alditol or cyclitol (component nente (B)) introduced into a new thermoplastic material.
- Components (A) and (B) can be introduced into the new plastic material individually or separately from one another, or components (A) and (B) can be put together in the form of a composition or composition containing components (A) and (B) are introduced into the new plastic material in the form of a composition consisting of components (A) and (B).
- components (A) and (B) consist of a renewable raw material.
- components (A) and (B), which may be in the form of powder, compact, granules, liquid, syrup, solution or flakes, are mixed with the new polymer to be stabilized, the polymer matrix is converted into the melt and then cooled.
- an additive which is solid at room temperature in a molten state into a polymer melt.
- components (A) and (B) can be in the form of so-called masterbatches or concentrates, which, for example, 10-90% of a stabilizer composition consisting of components (A) and (B) in a polymer or oligomer such as a polyethylene wax, Contain polypropylene wax or a natural vegetable wax, manufactured and introduced.
- a stabilizer composition consisting of components (A) and (B) in a polymer or oligomer such as a polyethylene wax, Contain polypropylene wax or a natural vegetable wax, manufactured and introduced.
- Components (A) and (B) can be introduced into the new thermoplastic material by mixing components (A) and (B) with the new thermoplastic material as a solid, and the resulting mixture is melted and then cooled.
- component (A) and component (B) used according to the invention act together as a synergistic stabilizer for the new thermoplastic material, the oxidative, thermal and / or actinic degradation of the new thermoplastic material being inhibited or prevented.
- component (A) and additionally component (B) into the new thermoplastic material, the Plastic stabilized against oxidative, thermal and / or actinic degradation.
- the present invention is particularly characterized in that a combination of polyphenols and alditols (sugar alcohols) and / or cyclitols is used to stabilize new thermoplastic materials.
- sugar alcohols and polyols are merely components in formulations for the heat stabilization of polyvinyl chloride (PVC) and other halogen-containing polymers such as polyvinylidene chloride (PVDC) in compositions which contain metal soaps as heat stabilizers.
- PVC polyvinyl chloride
- PVDC polyvinylidene chloride
- This stabilizing effect of polyols in halogen-containing polymers is explained by the fact that the zinc compounds which promote PVC degradation are chelated and deactivated (see HO Wirth, H. Andreas, Pure Appl. Chem. 1977, 49, 627-648 ; T. lida, K. Goto, J. Appl. Pol. Sci. 1980, 25, 887-900) or in order to achieve a reaction as an HCI scavenger in Zn-free PVC (see J. Steenwijk et al. Pol. Degr. Stab. 2006, 2233-2240).
- the introduction of at least one polyphenol and at least one alditol and / or at least one cyclitol alone and optionally together with at least one further primary and / or at least one secondary antioxidant is a very effective one Stabilization of new thermoplastic material against oxidative, thermal and / or actinic degradation can be achieved.
- both polyphenols and alditols or cyclitols are very environmentally friendly and inexpensive compounds. The process according to the invention can thus be used to stabilize new thermoplastic plastics in a very effective, environmentally friendly and cost-effective manner against oxidative, thermal and / or actinic degradation.
- the polyphenols (A) have at least at least one aromatic group with at least 2 phenol groups or at least two aromatic groups with one phenol group each and are preferably isolated from natural products, obtained from natural products by a bio-chemical route, chemically modified from natural products or produced in a nature-identical manner by chemical means.
- Suitable polyphenols (A) are, for example, bile acids, hydroxytyrosol, flavonols such as e.g. Chrysin, quercetin, hesperidin, neohesperidin, naringin, marin, kaempferol, fisetin, anthocyanins, e.g. Delphinidine and malvidin, carnosolic acid, carnosol, rosemic acid and resveratrol, tannins, silymarin, containing silybin, isosylibine, silydianine, ellagic acid.
- flavonols such as e.g. Chrysin, quercetin, hesperidin, neohesperidin, naringin, marin, kaempferol, fisetin, anthocyanins, e.g. Delphinidine and malvidin, carnosolic acid, carnosol, rosemic acid and resver
- the polyphenols are preferably isolated from natural substances and are therefore renewable raw materials; if necessary, a chemical-synthetic reaction can take place after isolation and purification.
- esters of bile acid e.g. Hexyl, heptyl, octyl, nonyl, decyl, isodecyl, lauryl, stearyl, myristyl, cetyl or oleyl gallate.
- natural products are often mixtures of different active substances and mixtures of optical isomers.
- Preferred polyphenols are the following structures:
- Tannins such as Gallotannin (Corilagin)
- Tannin or quercetin are particularly preferred.
- the at least one alditol has the empirical formula
- Ri is an optionally substituted sugar residue.
- the at least one alditol is preferably selected from the group consisting of 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.
- the at least one alditol mannitol or erythritol is very particularly preferred.
- Maltitol can also be present as a so-called syrup, which is obtained industrially by hydrogenating glucose and, in addition to maltitol, sorbitol, also contains hydrogenated oligo- and polysaccharides with alditol end groups.
- the alditols can be present in different optical isomers, for example in the D or L form or meso form.
- heptitol and octitol are: 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
- Preferred alditols and substituted alditols have a melting point of> 100 ° C., have low water solubility and low water absorption (hygroscopy).
- Other preferred compounds melt at the usual processing conditions of polyolefins in the range from 150 to -250 C, and e have a decomposition temperature> 250 e C.
- cyclitols ie. H. ring-shaped polyols can be used.
- 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 (myo-inositol) being preferred.
- inositol myo, scyllo, D-chiro-, L-chiro-, muco-, neo-, allo epi- and cis-inositol
- the alditols or cyclitols contained as components (B) are understood in terms of their total weight as component (B), so that the entirety of the alditols and / or cyclitols contained is always to be understood here.
- a further preferred embodiment provides that component (A) and component (B) in a weight ratio of 5:95 to 90:10, preferably 10:90 to 90:10, particularly preferably 20:80 to 80 : 20, into which new thermoplastic materials are introduced.
- thermoplastic synthetic material 94.0 to 99.96 parts by weight, preferably 98.5 to 99.91 parts by weight of a thermoplastic synthetic material or mixtures thereof.
- thermoplastic new material is selected from the group consisting of
- polymers of olefins or diolefins such as e.g. Polyethylene, especially LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE and UHMWPE, metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-penten-l, polybutadiene, polyisoprene,
- olefins or diolefins such as e.g. Polyethylene, especially LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE and UHMWPE, metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-penten-l, polybutadiene, polyisoprene,
- Polycyclooctene, polyalkylene-carbon monoxide copolymers, as well as corresponding copolymers in the form of statistical 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 graft polymers such as, for example, polypropylene-g-maleic anhydride, polypropylene-g-acrylic acid and polyethylene-g-acrylic acid, polyethylene-polybutyl acrylate-g-maleic acid hydride, long chain branched polypropylene copolymers, which are produced with alpha-olefins as comonomers, in particular 1-butene.
- polystyrene polymethylstyrene, polyvinylnaphthalene, styrene-butadiene (SB), styrene-butadiene-styrene (SBS ), Styrene-ethylene-butylene-styrene (SEBS), styrene-ethylene-propylene-styrene, styrene-soprene, styrene-isoprene-styrene (SIS), styrene-butadiene-acrylonitrile (ABS), styrene-acrylonitrile-acrylate (ASA ), Styrene-ethylene, styrene-maleic anhydride polymers including corresponding graft copolymers
- halogen-containing polymers e.g. Polyvinyl chloride (PVC), polychloroprene, polyvinylidene chloride (PVDC), copolymers of vinyl chloride and vinylidene chloride, copolymers of vinyl chloride and vinyl acetate, chlorinated polyethylene, polyvinylidene fluoride, epichlorohydrin homo- and copolymers, in particular with ethylene oxide (ECO),
- PVC Polyvinyl chloride
- PVDC polychloroprene
- PVDC polyvinylidene chloride
- copolymers of vinyl chloride and vinylidene chloride copolymers of vinyl chloride and vinyl acetate
- chlorinated polyethylene polyvinylidene fluoride
- epichlorohydrin homo- and copolymers in particular with ethylene oxide (ECO)
- polymers of unsaturated esters such as e.g. Polyacrylates and polymethacrylates such as polymethyl methacrylate (PMMA), polybutyl acrylate, polylauryl acrylate, polystearyl acrylate, polyacrylonitrile, polyacrylamides, and corresponding copolymers such as e.g. Polyacrylonitrile-polyalkyl acrylate,
- PMMA polymethyl methacrylate
- PMMA polybutyl acrylate
- polylauryl acrylate polylauryl acrylate
- polystearyl acrylate polyacrylonitrile
- polyacrylamides polyacrylamides
- copolymers such as e.g. Polyacrylonitrile-polyalkyl acrylate
- Polyvinyl alcohol polyvinyl acetate, polyvinyl butyral, polyallyl phthalate, polylallyl melamine,
- polyacetals e.g. Polyoxymethylene (POM)
- POM Polyoxymethylene
- corresponding copolymers e.g. Copolymers with butanal
- Polypropylene glycol polyethylene oxide, polypropylene oxide, polytet ra hyd rof u ra n, i) polyurethanes of hydroxy-terminated polyethers or polyesters and aromatic or aliphatic isocyanates, such as
- 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 e.g. Hexamethylene diamine or m-xylylenediamine or from aliphatic dicarboxylic acids such as e.g. Adipic acid or sebacic acid and aromatic diamines such as e.g. 1,4- or 1,3-diaminobenzene, blends of different polyamides, e.g. PA-6 and PA 6.6 or blends of polyamides and polyolefins such as e.g. PA / PP,
- Polyphthalamides e.g. made from terephthalic acid and / or isophthalic acid and aliphatic diamines such as e.g
- polyimides polyamide-imides, polyetherimides, polyesterimides, poly (ether) ketones, polysulfones, polyether sulfones, polyarylsulfones, polyphenylene sulfide, polybenzimidazoles, polyhydantoins,
- polyesters from aliphatic or aromatic dicarboxylic acids and diols or from hydroxy carboxylic acids such as e.g. Polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polypropylene terephthalate (PTT), polyethylene naphthylate (PEN), poly
- Polyhydroxynaphthalate polylactic acid (PLA), polyhydroxybutyrate (PBT), polyhydroxyvalate (PHV), polyethylene succinate,
- PC polycarbonates
- polyester carbonates and blends of these, such as PC / ABS, PC / PBT, PC / PET / PBT, PC / PA
- cellulose derivatives e.g. Cellulose nitrate, cellulose acetate, cellulose propionate, cellulose butyrate,
- epoxy resins consisting of di- or polyfunctional epoxy compounds in combination with e.g. Hardeners based on amines, anhydrides, dicyandiamide, mercaptans, isoicyanates or catalytic hardeners,
- phenolic resins such as, for example, phenol-formaldehyde resins, urea-formaldehyde resins or melamine-formaldehyde resins
- unsaturated polyester resins made from unsaturated dicarboxylic acids and diols with vinyl compounds such as styrene, alkyd resins
- silicones such as those based on dimethylsiloxanes, methylphenylsiloxanes or diphenylsiloxanes, the silicones mentioned also being fully or partially terminated, for example vinyl-terminated can
- the new thermoplastic material is particularly preferably selected from the group consisting of polymers of olefins or diolefins, such as e.g. Polyethylene, especially LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE and UHMWPE, metallocene-PE (m-PE), polypropylene, polyisobutylene, poly-4-methyl-pentene-1, polybutadiene, polyisoprene, polycyclooctene, polyalkylene carbon monoxide Copolymers, and corresponding copolymers in the form of statistical or block structures such as Polypropylene-polyethylene (EP), EPM or EPDM, ethylene-vinyl acetate (EVA), ethylene-acrylic esters, e.g.
- Polyethylene especially LDPE, LLDPE, VLDPE, ULDPE, MDPE, HDPE and UHMWPE, metallocene-PE (m-PE), polypropylene, polyisobutylene, poly
- Ethylene butyl acrylate, ethylene acrylic acid glycidyl acrylate, and corresponding graft polymers such as e.g. Polypropylene-g-maleic anhydride, polypropylene-g-acrylic acid and polyethylene-g-acrylic acid.
- thermoplastic new polyolefin is very particularly preferred.
- the new thermoplastic material can be polypropylene, in particular thus a polypropylene or polyethylene, in particular therefore a polyethylene.
- Polymers made from renewable raw materials in particular polyesters such as polylactic acid (PLA), polyhydroxybutyrate (PBT), polyhydroxyvalerate (PHV), polyethylene succinate, polybutylene succinate (PBS) and polyamides made from renewable raw materials such as polyamide 10, 10 or polyamide 11, are also particularly preferred.
- the polymers are halogen-free.
- thermoplastic synthetic material for example a further primary antioxidant
- additional stabilizers for example a further primary antioxidant
- a further primary antioxidant for example a further primary antioxidant
- a primary antioxidant is used to stabilize the new thermoplastic material, this is preferred, selected from the group consisting of phenolic antioxidants, amines, lactones and mixtures thereof.
- Alkylated monophenols such as 2,6-di-te / t-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-te / t-butyl-4-ethylphenol, 2 , 6-di-tert-butyl-4- n-butylphenol, 2,6-di-te / t-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2- (a-methylcyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-te / t-butyl-4-methoxymethylphenol, linear or branched nonylphenols, such as, for example 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6- (l , -methylund
- Alkylthiomethylphenols e.g. 2,4-dioctylthiomethyl-6-te / t-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol;
- Hydroquinones and alkylated hydroquinones such as e.g. 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-te / t-butylhydroquinone, 2,5-di-te / t-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2, 6-di-te / t-butylhydroquinone, 2,5-di-ferf-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-te / t-butyl- 4-hydroxyphenyl stearate, bis (3,5-di-tert-butyl-4-hydroxylphenyl) adipate;
- Tocopherols such as, for example, ⁇ -, ⁇ -, y-, d-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-te / t- butyl-3-methylphenol), 4,4'-thiobis (6-te / t-butyl-2-methylphenol), 4,4 , -thiobis (3,6-di-sec-amylphenol), 4,4 '-Bis (2,6-dimethyl-4-hydroxyphenyl) disulfide;
- Hydroxylated thiodiphenyl ethers such as 2,2, thiobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'-thiobis (6-te
- Alkylidene bisphenols such as 2,2'-methylenebis (6-te / t-butyl-4-methylphenol), 2,2-methylenebis (6-fe / f-butyl-4-ethylphenol), 2,2'-methylenebis [ 4-methyl-6- (a-methylcyclohexyl) phenol], 2,2 , -methylene bis (4-methyl-6-cyclhexylphenol),
- N- and S-benzyl compounds e.g. 3,5,3 ', 5'-tetra / t-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy-3,5-di -te / t-butylbenzylmercaptoacetate, tris (3,5-di- / t-butyl-4-hydroxybenzyl) amine, bis (4-te / t-butyl-3-hydroxy-2,6-dimethyl-benzylQdithioterephthalate, Bis (3,5-di-te / t-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-te / t-butyl-4-hydroxybenzylmercaptoacetate;
- Hydroxybenzylated malonates such as, for example, dioctadecyl 2,2-bis (3,5-di-tert-butvl-2-hydroxybenzyl malonate, dioctadecyl 2- (3-te / t-butyl-4-hydroxy-5-methyl-benzyl Qmalonate, Didodecylmercaptoethyl-2,2-bis (3,5-di-te / t-butyl-4-hydroxybenzylQmalonate, bis [4- (l, l, 3,3-tetramethylbutyl) phenyl] -2,2-bis ( 3,5-di-te / t-butyl-4-hydroxybenzyl) malonate; Aromatic hyd roxybenzyl compounds, such as 1,3,5-tris (3,5-di-fert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,4-bis (3,5-di
- Triazine compounds e.g. 2,4-bis (octylmercapto) -6- (3,5-di-fert-butyl-4-hydroxyanilino) -l, 3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di -te / t-butyl-4-hydroxyanilino) -l, 3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-te / t-butyl-4-hydroxyphenoxy) -l, 3rd , 5-triazine, 2,4,6-tris (3,5-di-te / t-butyl-4-hydroxyphenoxy) - 1,2,3-triazine, 1,3,5-tris (3,5- di-te / t-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-te / t-buty
- Benzylphosphonates e.g. Dimethyl-2,5-di-te / t-butyl-4-hydroxybenzylphosphonate, Dietyhl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, di-octadecyl-3,5-di-te / t- butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-fert-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3,5-di-te / t-butyl-4-hydroxybenzylphosphonic acid;
- Acylaminophenols e.g. 4-hydroxylauranilide, 4-hydroxystearanilide, octyl-N- (3,5-di-t / t-butyl-4-hydroxyphenyl) carbamate;
- Esters of ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with mono- 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, trimethylol propane, 4-hydroxymethyl-l-phospha-2,6,7-trioxabicyclo [2.2.2] o
- Esters of ß- (5-te / t-butyl-4-hydroxy-3-methylphenyl) propionic acid with mono- 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, penta- erythritol, tris (hydroxyethyl) isocyanate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2,6,7-trioxabicyclo
- Esters of ß- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with mono- 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-l-phospha-2,6,7-trioxabicyclo [2.2.2] octane;
- Esters of (3,5-di-fert-butyl-4-hydroxyphenyl) acetic acid with mono- or polyhydric alcohols e.g. Methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2,6,7-trioxabicyclo [2.2.2] octane;
- Amides of ß- (3,5-di-te / t-butyl-4-hydroxyphenyl) propionic acid e.g. N, N'- bis (3,5-di-te / t-butyl-4-hydroxyphenylpropionyl) hexamethylenediamide, N, N'- bis (3,5-di-te / t-butyl-4-hydroxyphenylpropionyl) hexamethylenediamide, N, N'- bis (3,5-di-te / t-butyl-4-hydroxyphenylpropionyl) hexamethylenediamide, N, N'- bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazide, N, N'-bis [2- (3- [3,5-di / t-butyl-4-hydroxyphenyl] propionyloxy) ethyl] oxamide (Nau
- vitamin C Ascorbic acid (vitamin C).
- phenolic antioxidants are monophenolic antioxidants based on renewable raw materials such as. B. Tocopherols (Vitamin E).
- the phenolic antioxidant pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate or octadecyl 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate is very particularly preferred as primary antioxidant used.
- r, r'-di-tert-octyldiphenylamine 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylamino-phenol, bis (4-methoxyphenyQamine, 2,6-di-tert -butyl-4-dimethylaminomethyl-phenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N, N, N ', N'-tetra-methyl-4,4'-diaminodiphenylmethane, l, 2- Bis [(2-methylphenyl) amino] ethane, l, 2-bis (phenylamino) propane, (o-tolyl) biguanide, bis [4- (l ', 3'-dimethylbutyl) phenyl]
- Preferred amine antioxidants are:
- N-oxides e.g. N, N-dialkylhydroxylamines, N, N-dibenzylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-distearylhydroxylamine, N-benzyl-a-phenylnitron, N-octadecyl-a-hexadecylnitron, and Genox EP (sold by Addivant) according to the formula:
- Preferred lactones are:
- Benzofuranones and indolinones such as e.g. 3- (4- (2-acetoxyethoxy) phenyl] -5,7-di-tert-butyl-benzofuran-2-one, 5,7-di-tert-butyl-3- [4- (2-stearoyloxyethoxy) - phenyl] benzofuran-2-one, 3,3'-bis [5,7-di-tert-butyl-3- (4- (2-hydroxyethoxy] phenyl) benzofuran-2-one), 5,7-di tert-butyl-3- (4-ethoxyphenyl) benzofuran-2-one, 3- (4-acetoxy-3,5-dimethylphenyl) -5,7-di-tert-butyl-benzofuran-2-one, 3- (3,5-dimethyl-4-pivaloyloxyphenyl) -5,7-di-tert-butyl-benzo
- the at least one secondary antioxidant is selected from the group consisting of phosphorus compounds, in particular phosphites and phosphonites, organosulfur compounds, in particular sulfides and disulfides, and Mixtures of these.
- phosphites or phosphonites examples include triphenyl phosphite, diphenylalkyl phosphite, phenyl dialkyl phosphite, tri (nonyl phenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris (2,4-di-te / t-butylphenyl) phosphite - erythritol diphosphite, bis (2,4-di-te / t-butylphenyl) pentaerythritol diphosphite, bis (2,4-di-cumylphenyl) pentaerythritol diphosphite, bis (2,6-di-te / t-butyl-4-methylphenyl
- Particularly preferred phosphites / phosphonites are:
- the phosphite tris (2,4-di-te / t-butylphenyl) phosphite is particularly preferably used as a secondary antioxidant.
- Preferred sulfur compounds are:
- a secondary antioxidant in addition to the minimum A secondary antioxidant can also be used as another primary antioxidant.
- thermoplastic synthetic material In the event that additional components are added to the thermoplastic synthetic material, these 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.
- At least one additive which is selected from the group consisting of UV absorbers, light stabilizers, metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, toughness improvers, plasticizers, anti-plasticizers, lubricants, rheology modifiers, can preferably also be introduced into the new thermoplastic plastic , Thixotropic agents, chain extenders, optical brighteners, antimicrobial agents, antistatic agents, thermally and / or electrically conductive additives, slip agents, antiblocking agents, coupling agents, crosslinking agents, anti-crosslinking agents, hydrophilizing agents, hydrophobizing agents, adhesion promoters, detergents, anti-caking agents, acidifiers, blowing agents -Additives, defoaming agents, odor scavengers, marking agents In, antifogging agents, fillers, reinforcing materials and mixtures thereof.
- thermoplastic new plastic is additionally introduced into the thermoplastic new plastic
- Acid scavengers preferably calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium lactate, calcium stearoyl 2-lactate, hydrotalcites, in particular synthetic hydrotalcites based on aluminum, magnesium and zinc, hydrocalumites, zeolites, alkaline earth metal oxides, in particular calcium oxide and magnesium oxide, alkaline earth metal carbonates Calcium carbonate, magnesium carbonate and dolomite, and hydroxides, in particular brucite (magnesium hydroxide), b) light stabilizers, preferably light stabilizers from the group of hindered amines,
- 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-te / t-butyl-2'-hydroxyphenyl) benzotriazole, 2- (5'-te / t-butyl-2'-hydroxy-phenyl) benzotriazole, 2- (2'-hydroxy-5 '- (l, l, 3,3-tetramethylbutyl) phenyl) benzotriazole, 2 - (3 ', 5'-Di-te / t-butyl-2'-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3'-te / t-butyl-2'-hydroxy-5'-methylphenyl-5- chlorobenzotriazole, 2- (3'-sec-butyl-5'-te / t-butyl-2'-hydroxyphenyl) benzotriazole,
- 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.
- Suitable acrylates are, for example, ethyl-a-cyano- ⁇ , ⁇ -diphenyl acrylate, isooctyl-a-cyano- ⁇ , ⁇ -diphenyl acrylate, methyl-a-carbomethoxycinnamate, methyl-a-cyano- ⁇ -methyl-p-methoxycinnamate, Butyl-a-cya no-ß-methyl-p-methoxycinnamate, methyl-a-carbomethoxy-p-methoxycinnamate and N- (ß-carbomethoxy-ß-cyanovinyl) -2-methylindoline.
- Suitable esters of benzoic acids are, for example, 4-te / t-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoylresorcinol, 2,4-di-te / t-butylphenyl-3,5- di-te / t-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-te / t-butyl-4-hydroxybenzoate, octa-decyl-3,5-di-te / t-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-te / t-butylphenyl-
- Suitable oxamides are, for example , 4,4'-dioctyloxyoxanilide, 2,2'-diethoxy-oxanilide, 2,2'-dioctyloxy-5,5'-di-te / t-butoxanilide, 2,2'-didodecyloxy-5,5 '-di-te / t-butoxanilide, 2-ethoxy-2 , -ethyloxanilide, N, N'-bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5-te / t-butyl-2'-ethoxanilide and its blends with 2-
- 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) -l, 3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -l , 3,5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2 i 4-dimethylphenyl) -l, 3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl ) -4,6-bis (4-methylphenyl-l, 3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl
- 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-l, 2,4-triazole,
- Suitable hindered amines are, for example, l, bis (2,2,6,6-tetramethyl-4-piperidyl) succinate, bis (1,2,6,6-pentamethyl-4-piperidyl) sebazate, bis (l octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebazate, l-cyclohexyloxy-2, 2,6,6-tetramethyl-4-octadecylaminopiperidine, bis (l-acyl-2,2,6,6 tetramethyl piperidin-4-yl) sebazate 1- (2-hydroxy-2-methylpropoxy) -4-hydroxy-2, 2,6,6-tetramethylpiperidine, 1- (2-hydroxy-2-methylpropoxy) -4-oxo -2,2,6,6-tetra-methylpiperidine, bis (l-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, N, N'-bis-form
- the structures specified above also include the sterically hindered NH, 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:
- n is in each case 3 to 100.
- Suitable dispersants are, for example:
- Polyacrylates e.g. Copolymers with long chain side groups, polyacrylate block copolymers, alkyl amides: e.g. N, N'-1,2-ethanediylbisoctadecanamide, sorbitan esters, e.g. Monostearyl sorbitan esters, titanates and zirconates each with long chain substituents, reactive copolymers with functional groups e.g. Polypropylene-co-acrylic acid, polypropylene-co-maleic anhydride, polyethylene n-co-glycidyl methacrylate, polystyrene-old maleic anhydride, poly
- Siloxanes e.g. Dimethylsilanediol-ethylene oxide copolymer, polyphenylsiloxane copolymer, amphiphilic copolymers: e.g. Polyethylene block polyethylene oxide, dendrimers, e.g. hydroxyl group-containing dendrimers.
- Suitable nucleating agents are, for example, talc, alkali or alkaline earth metal salts of mono- and polyfunctional carboxylic acids, such as, for. B. benzoic acid, succinic acid, adipic acid, e.g. Sodium benzoate, zinc glycerolate, aluminum hydroxy-bis (4-te / t-butyl) benzoate, benzylidene sorbitols such as e.g.
- Trimesic acid tricyclohexylamide trimesic acid tri (4-methylcyclohexylamide), trimesic acid tri (tert.butylamide)
- N, N ', N "-l 3,5-benzen
- Suitable anti-nucleating agents are, for example, azine dyes such as e.g. Nigrosine, ionic liquids and / or lithium salts.
- Suitable flame retardants include:
- Inorganic flame retardants such as Al (OH) 3 , Mg (OH) 2 , AIO (OH), MgC0 3 , layered silicates such as montmorillonite or sepiolite, not or organically modified, double salts such as Mg-Al-silicates, POSS- (Polyhedral oligomeric silsesquioxane) compounds, huntite, hydromagnesite or halloysite as well as Sb 2 0 3 (ATO), Sb 2 0 5 , MO0 3 , ammonium molybdate (AOM), zinc stannate, zinc hydroxystate, b) Nitrogen-containing flame retardants such as melamine, Meier, melam, melon, melamine derivatives, melamine condensation products or melamine salts, benzoguanamine, polyisocyanurates, allantoin, phosphacenes, in particular melamine cyanurate, melamine phosphate, dimelamine salts,
- radical formers e.g. Alkoxyamines, hydroxylamine esters, azo compounds, sulfenamides, sulfenimides, dicumyl or polycumyl, hydroxyimides and their derivatives such as e.g. Hydroxyimide ester or hydroxyimide ether
- phosphorus-containing flame retardants such as red phosphorus, phosphates such as e.g. Resorcinol diphosphate, bisphenol A diphosphate and their oligomers, triphenyl phosphate, ethylenediamine diphosphate, phosphinates such as e.g. Salts of hypophosphorous acid and its derivatives such as alkylphosphinate salts e.g.
- DOPO 9,10-dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide
- Halogen-containing flame retardants based on chlorine and bromine such as, for example, polybrominated diphenyl oxides, such as, for example, decabromodiphenyl oxide, tris (3-bromo-2,2-bis (bromomethyl) propyl phosphate, tris (tribromoneopentyl) phosphate, tetrabromophthalic acid, 1, 2-bis (tribromophenoxy) ethane, hexabromocyclododecane, brominated diphenylethane, tris (2,3-dibromopropyl) isocyanurate, ethylene bis (tetrabromophthalimide), tetrabromobisphenol A, brominated polystyrene, brominated polybutadiene or polystyrene-brominated, polystyrene-brominated Copolymers, brominated polyphenylene ether, brominated epoxy resin, polypentabromo
- Sulfur-containing compounds such as elemental sulfur, disulfides and polysulfides, thiuram sulfide, dithiocarbamates, mercaptobenzothiazole and sulfenamides,
- antidrip agents such as Polytetrafluoroethylene,
- Silicon-containing compounds such as Polyphenylsiloxanes
- carbon modifications such as e.g. Carbon nanotubes (CNT), expanded graphite or graphene
- Suitable fillers and reinforcing materials are, for example, synthetic or natural materials such as e.g. Calcium carbonate, silicates, glass fibers, glass balls (solid or hollow), talc, mica, kaolin, barium sulfate, metal oxides and metal hydroxides, carbon black, graphite, carbon nanotubes, graphene, wood flour or fibers from natural products such as e.g. Cellulose or synthetic fibers such as polyester or polyamide fibers.
- Other suitable fillers are hydrotalcites or zeolites or layered silicates such as e.g. Montmorillonite, bentonite, beidelite, mica, hectorite, saponite, vermiculite, ledikite, magadite, lllite, kaolinite, wollastonite, attapulgite.
- 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, and organic pigments are, for example
- Other suitable pigments are effect pigments based on metal or pearlescent pigments based on metal oxide.
- Suitable chain extenders for the linear molecular weight build-up of polycondensation polymers such as polyesters or polyamides are, for example, diepoxides, bis-oxazolines, bis-oxazolones, bis-oxazines, diisocyanates, dianhydrides, bis-acyl lactams, bis-maleimides, dicyanates, carbodiimides or polycarbodiimides.
- Other suitable chain extenders are polymeric compounds such as polystyrene-polyacrylate-polyglycidyl (meth) acrylate Copolymers, polystyrene-maleic anhydride copolymers and polyethylene-maleic anhydride copolymers.
- 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. of the following structures:
- Suitable antistatic agents include ethoxylated alkylamines, fatty acid esters, alkyl sulfonates and polymers such as e.g. Polyether amides.
- Suitable antiozonants are the amines mentioned above, e.g. 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-
- Suitable electrically conductive additives are the antistatic agents already mentioned and, furthermore, electrically conductive fillers such as carbon black, graphene, carbon nanotubes (CNTs), metal powder such as copper or silver, but also conductive polymers such as polyanilines, polypyrrole or polythiophenes.
- Suitable thermally conductive additives are, for example, aluminosilicates, aluminum nitride or boron nitride.
- Suitable odor traps are, for example, inorganic absorbents such as zeolites, hydrotalcites, silicates or organic complexing or reactive compounds such as zinc riceneolate or epoxides.
- Suitable marking agents are, for example, fluorescent dyes, rare earths or antistokes crystals such as yttrium oxysulfides, gadolinium oxysulfides or cerium tantalum oxides, which are associated with rare earths such as e.g. ERbium or ytterbium are doped and show luminescence under IR irradiation. These markers can be used in small ppm amounts to identify the polymer or the additive for identification e.g. of the manufacturer are added.
- Suitable mold release agents are, for example, montan waxes.
- Components (A) and (B) and, if appropriate, the additional additives can be incorporated into the plastic recyclate by customary processing methods, the polymer being melted and mixed with the additive composition according to the invention and any further additives, preferably by mixer, kneader and extruder.
- Preferred processing machines are extruders such as e.g. Single-screw extruders, twin-screw extruders, planetary roller extruders, ring extruders, co-kneaders, which are preferably equipped with vacuum degassing. Processing can be carried out under air or possibly under inert gas conditions such as done under nitrogen.
- the present invention further relates to a plastic composition containing or consisting of
- the plastic composition is characterized in that the plastic composition
- thermoplastic synthetic material 94.0 to 99.96 parts by weight, preferably 98.5 to 99.91 parts by weight, of a thermoplastic synthetic material or mixtures thereof,
- composition according to the invention preferably contains at least one primary antioxidant and at least one secondary antioxidant, but it is also possible for the composition according to the invention to be free from the further primary and / or secondary antioxidants.
- the plastic composition according to the invention additionally contains at least one additive which is selected from the group consisting of UV absorbers, light stabilizers, metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, impact strength improvers, plasticizers, lubricants, rheology modifiers, Thixotropic agents, chain extenders, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anti-crosslinking agents, hydrophilizing agents, hydrophobizing agents, adhesion promoters, diperging agents, compatibilizers, oxygen scavengers, additive agents, de-scavenger agents, de-scavenger agents, de-scavenger agents Odor traps, markers, anti-fogging agents, fillers, reinforcement substances and mixtures thereof. It is further preferred that the plastic composition additionally contains at least one additive which is selected from the group consisting of
- Acid scavengers preferably calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium stearate, calcium lactate, calcium stearoyl-2-lactate, hydrotalcites, especially synthetic hydrotalcites based on aluminum, magnesium and zinc, hydrocalumites, zeolites, alkaline earth oxides, especially calcium oxide and magnesium oxide, zinc oxide Alkaline earth carbonates, in particular calcium carbonate, magnesium carbonate and dolomite, and hydroxides, in particular brucite,
- the plastic composition according to the invention can preferably be produced using a method according to the invention for stabilizing new thermoplastic material against oxidative, thermal and / or actinic degradation, or was produced therewith.
- the at least one secondary antioxidant is selected from the group consisting of phosphorus compounds, in particular phosphites and phosphonites, organosulfur compounds, in particular sulfides and disulfides, and mixtures thereof .
- the phosphite tris (2,4-diet / t-butylphenyl) phosphite is particularly preferably contained as a secondary antioxidant in the plastic composition according to the invention.
- the present invention also relates to a molding compound or a molded part which can be produced from the plastic composition according to the invention, in particular in the form of injection molded parts, foils, films, lacquers, coatings, Foams, fibers, cables, pipes, profiles, hollow bodies, tapes, membranes, eg geomembranes and / or adhesives, which are manufactured by extrusion, injection molding, blow molding, calendering, pressing processes, spinning processes, brushing, dipping and / or rotomoulding eg for the electrical industry, for the construction industry, for the transport industry, for medical applications, for household and electrical appliances, for vehicle parts, for mechanical engineering, for agricultural applications, for medical technology, for consumer goods, for sporting goods, for Packaging, for furniture, and / or for textiles.
- the present invention also relates to a stabilizer composition for stabilizing new thermoplastic material against oxidative, thermal and / or actinic degradation, consisting of
- component (B) at least one alditol and / or at least one cyclitol. It is preferred here that component (A) and component (B) are present in a weight ratio of 5:95 to 90:10, preferably 10:90 to 90:10, particularly preferably 20:80 to 80:20.
- the present invention also relates to the use of a stabilizer composition containing or consisting of
- thermoplastic plastics thermoplastic virgin resins, thermoplastic pristine resins
- a commercially available polypropylene (Moplen HP 500N, Lyondell Basell Industries) was homogenized in a powder-powder mixture with the stabilizers specified in Table 2 and in a twin-screw microextruder (MC 5, manufacturer DSM) circulated for 30 minutes at 200 ° C and 200 revolutions per minute and the decrease in force recorded.
- the force is a direct measure of the molecular weight of polypropylene, the lower the decrease, the higher the stability.
- A0-1 Pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate
- P-1 tris (2,4-di-tert-butylphenyl) phosphite
- the synergistic combination according to the invention proves to be superior to the synthetic commercial synergistic combinations of A0-1 and PI (comparative example 2), since there is less degradation of the polymer over the test period.
- the individual components on the other hand, have little or no effect, since the degradation of the polymer takes place close to the polymer without addition.
- a commercially available base-stabilized polypropylene (Moplen HP 500N, Lyondell Basell Industries) in the form of a granulate was homogenized with the powdery stabilizers specified in Table 3 and in a 16 mm twin screw extruder (PTW 16, manufacturer: Haake, L / D ratio: 20) at 210 ° C maximum temperature and 140 revolutions / min extruded and granulated. After extrusion, the MVR (230 ° C / 2.16 kg) was measured in accordance with DIN / ISO 1133.
- Sabostab UV40 is a 1,6-hexanediamine
- Araldit GT 6071 is a commercial product from Huntsman.
- the examples according to the invention have a lower MVR during processing, i.e. less degradation and thus improved processing stability.
- the examples according to the invention have a lower MVR during processing, i.e. less degradation and thus improved processing stability.
- the synergistic combination according to the invention shows a clear stabilizing effect, since less degradation, i.e. a higher residual force is proven.
- inventive example 7 for 504 hours at 150 e C in a convection oven was stored, it is shown an unchanged after storage MVR value of 15.0 [cm 3/10 min].
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Abstract
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DE102018218120.9A DE102018218120A1 (de) | 2018-10-23 | 2018-10-23 | Verfahren zur Stabilisierung von thermoplastischer Kunststoffneuware sowie stabilisierte Kunststoffzusammensetzungen, hieraus hergestellte Formmassen und Formteile, Stabilisator-Zusammensetzungen sowie Verwendungen hiervon |
PCT/EP2019/078221 WO2020083740A1 (de) | 2018-10-23 | 2019-10-17 | Verfahren zur stabilisierung von thermoplastischer kunststoffneuware sowie stabilisierte kunststoffzusammensetzungen, hieraus hergestellte formmassen und formteile, stabilisator-zusammensetzungen sowie verwendungen hiervon |
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US (1) | US20210388176A1 (de) |
EP (1) | EP3870641A1 (de) |
JP (1) | JP2022505635A (de) |
KR (1) | KR20210102884A (de) |
CN (1) | CN113166470A (de) |
DE (1) | DE102018218120A1 (de) |
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DE102020124025A1 (de) | 2020-09-15 | 2022-03-17 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verwendung von Dieugenol, Oligomeren und/oder Polymeren von Eugenol zur Stabilisierung von organischen Materialien, stabilisiertes organisches Material sowie Verfahren zur Stabilisierung von organischen Materialien |
CN112251011B (zh) * | 2020-09-18 | 2022-05-24 | 东莞市雄林新材料科技股份有限公司 | 一种光稳定型tpu复合材料及其制备方法 |
CN117957279A (zh) * | 2021-09-09 | 2024-04-30 | Sabic环球技术有限责任公司 | 具有改进的辐射稳定性的聚丙烯组合物 |
WO2023076723A1 (en) * | 2021-11-01 | 2023-05-04 | Interfacial Consultants Llc | Biodegradable polymer compositions |
CN114437447B (zh) * | 2022-01-26 | 2022-12-23 | 福州大学 | 一种高力学性能可降解复合泡沫材料及其制备方法 |
CN114716750B (zh) * | 2022-03-23 | 2023-09-26 | 武汉金发科技有限公司 | 一种聚烯烃母粒及其制备方法和应用 |
CN114621522B (zh) * | 2022-03-25 | 2024-01-02 | 上海金发科技发展有限公司 | 一种聚丙烯组合物及其制备方法和应用 |
DE102022203654A1 (de) | 2022-04-12 | 2023-10-12 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verfahren zur Stabilisierung von Übergangsmetall enthaltenden Kunststoffen, stabilisierte, übergangsmetallhaltige Kunststoffzusammensetzungen, Formmasse oder Formteil sowie Verwendung einer Stabilisatorzusammensetzung zur Stabilisierung von Übergangsmetall enthaltenden Kunststoffen |
CN115340710A (zh) * | 2022-06-30 | 2022-11-15 | 广元瑞峰新材料有限公司 | 一种环保增塑交联剂及其制备方法 |
KR102476307B1 (ko) * | 2022-07-25 | 2022-12-12 | 구경환 | 우수한 강도 및 내부식성을 갖는 유체 저장탱크 및 이의 제조방법 |
US20240084112A1 (en) * | 2022-08-23 | 2024-03-14 | Impact Biolife Science, Inc. | Antimicrobial plastic |
CN116063793B (zh) * | 2023-02-28 | 2024-03-12 | 武汉金发科技有限公司 | 一种聚烯烃复合材料及其制备方法和应用 |
CN116496570B (zh) * | 2023-04-24 | 2024-02-27 | 浙江丹亭新材料有限公司 | 一种具有智能温控功能的电热材料及其制备方法 |
CN116675909B (zh) * | 2023-05-10 | 2024-01-02 | 荣成荣鹰橡胶制品有限公司 | 一种实心轮胎的制备方法 |
CN116925560B (zh) * | 2023-07-15 | 2024-02-09 | 广东安拓普聚合物科技股份有限公司 | 一种建筑装饰板材及其制备方法 |
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DE102009014856A1 (de) * | 2009-03-30 | 2010-10-07 | H.C. Starck Clevios Gmbh | Polymerbeschichtungen mit verbesserter UV- und Temperaturstabilität |
EP2471862B1 (de) * | 2009-08-24 | 2015-05-27 | Adeka Corporation | Vinylchloridharzzusammensetzung für transparente produkte |
WO2011129396A1 (ja) * | 2010-04-14 | 2011-10-20 | 住友化学株式会社 | 熱可塑性ポリマー組成物および安定剤組成物 |
US20140039066A1 (en) * | 2012-08-03 | 2014-02-06 | Piped Limited | Formulation for gritty foam dispenser |
US20160068656A1 (en) * | 2014-09-09 | 2016-03-10 | Celanese Acetate Llc | Cellulose ester plastics and methods and articles relating thereto |
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DE102017217312A1 (de) * | 2017-09-28 | 2019-03-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Stabilisierung von halogenfreien thermoplastischen Kunststoff-Rezyklaten sowie stabilisierte Kunststoffzusammensetzungen und hieraus hergestellte Formmassen und Formteile |
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