WO2022195041A1 - Stabilisator-zusammensetzung, verwendung der stabilisator-zusammensetzung, verfahren zur stabilisierung von kondensationspolymeren gegen hydrolytischen abbau sowie hydrolysestabilisierte zusammensetzung und formkörper oder formteil hieraus - Google Patents
Stabilisator-zusammensetzung, verwendung der stabilisator-zusammensetzung, verfahren zur stabilisierung von kondensationspolymeren gegen hydrolytischen abbau sowie hydrolysestabilisierte zusammensetzung und formkörper oder formteil hieraus Download PDFInfo
- Publication number
- WO2022195041A1 WO2022195041A1 PCT/EP2022/057056 EP2022057056W WO2022195041A1 WO 2022195041 A1 WO2022195041 A1 WO 2022195041A1 EP 2022057056 W EP2022057056 W EP 2022057056W WO 2022195041 A1 WO2022195041 A1 WO 2022195041A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- bis
- aziridinecarboxamide
- aziridinyl
- acid
- Prior art date
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- 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
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- PJPGMULJEYSZBS-VZFHVOOUSA-N valienol Chemical compound OCC1=C[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O PJPGMULJEYSZBS-VZFHVOOUSA-N 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- HREVPIABJKTEDU-CNVXYERZSA-N viscumitol Chemical compound CO[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@H]1OC HREVPIABJKTEDU-CNVXYERZSA-N 0.000 description 1
- HREVPIABJKTEDU-UHFFFAOYSA-N viscumitol Natural products COC1C(O)C(O)C(O)C(O)C1OC HREVPIABJKTEDU-UHFFFAOYSA-N 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
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 235000010930 zeaxanthin Nutrition 0.000 description 1
- 239000001775 zeaxanthin Substances 0.000 description 1
- 229940043269 zeaxanthin Drugs 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 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
- BHTBHKFULNTCHQ-UHFFFAOYSA-H zinc;tin(4+);hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Sn+4] BHTBHKFULNTCHQ-UHFFFAOYSA-H 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
-
- 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
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/38—Boron-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- 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
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/06—Polyethene
-
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
- C08L69/005—Polyester-carbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Definitions
- Stabilizer composition use of the stabilizer composition, process for stabilizing condensation polymers against hydrolytic degradation, and hydrolysis-stabilized composition and molding or molding made therefrom
- the present invention relates to a novel stabilizer composition based on an aziridine and at least one hydrotalcite, zeolite, dawsonite or mixtures thereof.
- the stabilizer composition is suitable for stabilizing condensation polymers, in particular aliphatic polyesters, against hydrolytic degradation.
- the invention also relates to the use of the stabilizer composition according to the invention and to a method for stabilizing condensation polymers against hydrolytic degradation.
- the present invention relates to moldings and moldings that can be produced from the composition according to the invention.
- Polycondensation polymers such as polyesters, polyamides and polycarbonates are generally classified as hydrolysis-sensitive polymers, since the chemical bonds of these polymers can be broken by water. This can be advantageous for degradation of these polymers, for example in the environment, but is also often a disadvantage, particularly in the case of technical applications and desired extended useful lives.
- Polymers from fossil raw materials are increasingly being replaced by polymers from renewable raw materials.
- These "bio" polymers are, for example, based on aliphatic polyesters such as polylactic acid, also referred to as polylactide or PLA.
- aliphatic ester groups are significantly more sensitive to hydrolysis than (partly) aromatic ester groups (see, for example, M. Dröscher et al, Angewandte Makromolecular Chemistry 1984, 128, 203-213).
- WO 2012 072 489 mentions carbodiimides, polycarbodiimides, epoxides, alkyl ketene dimers and oxazolidinones as hydrolysis stabilizers.
- CN 101 759 969 describes hydrolysis-resistant PLA-based compositions which contain carbodiimides, epoxy, oxoazolines, oxazines or aziridines.
- Compositions are also known, for example from WO 94/24201, which contain further additives such as calcium oxide or calcium silicates in addition to the hydrolysis stabilizer in the form of epoxides.
- drilling fluids which can contain aziridines, hydrotalcites and degradable polymers (WO2015/065575).
- Polycondensates containing aziridines are therefore to be regarded as the closest prior art.
- aziridines in polyesters and PLA is mentioned in US 3959228, in TW 1472575, in US 2014/0100318 or US 2016/024297.
- Patent claim 9 specifies possible uses of the stabilizer composition
- patent claim 10 relates to a method for stabilizing condensation polymers against hydrolytic degradation
- Patent claim 13 relates to a hydrolysis-stabilized composition
- patent claim 17 to a molded part or a molded body that can be produced from the hydrolysis-stabilized composition.
- the present invention thus relates to a stabilizer composition consisting of at least one aziridine and at least one hydrotalcite, zeolite, dawsonite or mixtures thereof.
- polyesters with combinations of aziridines with hydrotalcites, zeolites or dawsonite have particularly good hydrolytic stability. These combinations have not previously been described in the literature.
- New hydrolysis-stabilized plastic compositions made from polycondensation polymers such as polyesters or polyamides, as well as new stabilizer compositions for improving the hydrolytic stability with high effectiveness, particularly in the case of biopolymers such as PLA, are made available.
- the at least one aziridine is selected from the group consisting of monofunctional, difunctional, tetrafunctional and/or multifunctional aziridines with, for example, the following structures:
- 1-Aziridinepropionic acid 2-methyl-, 1,1'-[2-[[3-[3-(1-aziridinyl)-1-oxopropoxy]-2-(hydroxymethyl)-2-[[3-( 2-methyl-1-aziridinyl)-1-ox-opropoxy]methyl]propoxy]methyl]-2-[[3-(2-methyl-1-aziridinyl)-1-ox-opropoxy]methyl]-1,3 -propanediyl]ester;
- Particularly suitable aziridines are:
- Particularly preferred aziridines are the following compounds:
- aziridines mentioned are commercially available, e.g. from Menadiona (Barcelona, Spain) or Polyaziridine LLC (Palm Beach, USA).
- the at least one hydrotalcite is preferably selected from the group consisting of compounds of the general formula (M 2+ ) 1-x . (M 3+ ) x . (OH) 2 . (A n- ) x/n . m H 2 O where
- A is an anion with the valence n, preferably OH-, HCO 3 -, CH 3 COO-, C 6 H 5 COO-, CO 3 2- , SO 4 2- , HPO 4 2- , n is 1 or 2,
- m is a number from 0 to 20.
- the hydrotalcites are selected from the group consisting of Ca 4 Al 2 (OH) 12 CO 3 • 5 H 2 O, Al 2 O 3 • 6 MgO • CO 2 • 12 H 2 O, Mg 4.5 Al 2 (OH ) 13 • CO 3 • 3.5 H 2 O, Mg 6 AI 2 (OH) 16 • CO 3 • 4 H 2 O, 4 MgO • AIO3 • CO 2 • 9 H 2 O, 4 MgO • AI 2 O 3 • CO 2 • 6 H 2 O, ZnO • 3 MgO • Al 2 O 3 • CO 2 • 8-9 H 2 O and ZnO • 3 MgO • Al 2 O 3 • CO 2 • 5-6 H 2 O.
- the at least one dawsonite is selected from the group consisting of compounds of the general formula whereby
- M an element selected from the group consisting of H, Li, Na, K, Mg 1/2 , Ca 1/2 , Sr 1/2 , Zn 1/2 ;
- Z is a substituent selected from the group consisting of CO2, SO2, (Cl 2 O 7 ) 1/2 , B 4 O 6 , S 2 O 2 (thiosulfate) and/or C 2 O 2 (oxalate); m if M is Mg 1/2 , Ca 1/2 , a number between 1 and 2, in all other cases a number between 1 and 3; n is a number between 1 and 4; o a number between 2 and 4; and p is a number between 0 and 30.
- the at least one dawsonite is selected from the group consisting of potassium aluminocarbonate sodium aluminothiosulphate potassium alumosulfite Calcium alumooxalate ⁇ (CaO) (Al 2 O 3 ) (C 2 O 2 ) 2 .5H 2 O ⁇ , magnesium alumotet- .aborate ⁇ (MgO)-(AI 2 O 3 ) ⁇ (B 4 O 6 ) 2 ⁇ 5 H 2 O ⁇ , sodium alumodihydroxycarbonate, potassium alumodihydroxycarbonate and naturally occurring alkali alumocarbonate minerals such as indigirite, tunisit, alumohydrocalcite and Strontiodresserit.
- potassium aluminocarbonate sodium aluminothiosulphate potassium alumosulfite Calcium alumooxalate ⁇ (CaO) (Al 2 O 3 ) (C 2 O 2 ) 2 .5H 2 O ⁇ magnesium al
- the at least one zeolite is preferably selected from the group consisting of compounds of the general formula
- M an element of the first or second main group, in particular Li, Na, K, Mg, Ca, Sr or Ba; y:x has a value from 0.8 to 15, preferably from 0.8 to 1.2, and w is a number from 0 to 300, preferably from 0.5 to 5.
- hydrotalcites, zeolites, dawsonites or mixtures thereof are used as an anhydrous formulation.
- the weight ratio of the total of the aziridine to all of the at least one hydrotalcite, dawsonite and/or zeolite is from 20:1 to 1:20, preferably from 10:1 to 1:10, particularly preferably from 5:1 to 1:5.
- the present invention relates to the use of a stabilizer composition according to the invention as described above for stabilizing condensation polymers against hydrolytic degradation.
- the present invention relates to a process for stabilizing condensation polymers against hydrolytic degradation, in which a stabilizer composition according to the invention, described above, is admixed to or blended with the condensation polymer.
- the stabilizer composition is present in a weight ratio of from 0.01 to 10% by weight, preferably from 0.05 to 5% by weight. %, particularly preferably from 0.1 to 3% by weight, based on the polycondensation polymer, is used or mixed in.
- the present invention relates to a hydrolysis-stabilized composition containing or consisting of at least one condensation polymer and a stabilizer composition according to the invention according to any one of claims 1 to 8.
- the condensation polymer is selected from the group consisting of a) polyamides, such as polyamide-6, 6.6, 6.9, 6.10, 4.6, 4.10, 6.12, 10.10 , 10.12, 12.12, polyamide 4, polyamide 7, polyamide 8, polyamide 9, polyamide 11, polyamide 12 and (partly) aromatic polyamides such as polyphthalamides, for example produced from terephthalic acid and/or isophthalic acid and aliphatic diamines such as hexamethylenediamine or m-xylylenediamine or from aliphatic dicarboxylic acids such as adipic acid o- of sebacic acid and aromatic diamines such as 1,4- or 1,3-diaminobenzene, referred to, for example, as polyamide 6T, polyamide 9T, polyamide 61, polyamide 6-3-T, blends of different polyamides such as PA-6 and PA 6.6, PA6T and PA6I, PA-6.6
- polyesters made from aliphatic or aromatic dicarboxylic acids and diols or from hydroxycarboxylic acids in particular aliphatic polyesters such as polyethylene terephthalate (PET), polybutylene terephthalate (PBT), polytrimethylene terephthalate (PTT), polypropylene terephthalate (PPT), polyethylene naphthylate (PEN) , poly-1,4-dimethylol-cyclohexane terephthalate, polyhydroxybenzoate, polyhydroxynaphthalate, polylactic acid (PLA), polyhydroxybutyrate (PHB), polyhydroxyvalerate (PHV), polybutylene succinate (PBS), polybutylene succinate adipate (PBSA), polyethylene succinate cinate, polycaprolactone, c) polycarbonates, polyester carbonates, and blends such as PC/ABS, PC/PBT, PC/PET/PBT, PC/PA, d) and mixtures, combinations or blends of
- polymers specified under a) to c) can have both amorphous and (partially) crystalline morphologies.
- polyesters are aliphatic polyesters, i. H. Polyester which can be produced from aliphatic dicarboxylic acids and aliphatic diols or from aliphatic lactones.
- diols for aliphatic polyesters examples include ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 1,6-hexanediol, 2,5-hexanediol, 3 -Methyl-2,4-pentanediol, 2-methyl-2,4-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol , -1,6,2-ethylhexanediol-1,3, 2,2-diethylpropanediol-1,3, 2,2-bis(4-hydroxycyclohexyl)propane, 2,2-bis(4-hydroxypropoxyphenyl
- dicarboxylic acids examples include malonic acid, dimethylmalonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, brassylic acid, tetradecanedioic acid, hexadecanedioic acid, cyclohexane-1,3-dicarboxylic acid or cyclohexane-1,4-dicarboxylic acid.
- aromatic structures can also be present to a minor extent, up to 20 mol %, preferably less than 10 mol %, very particularly preferably less than 1 mol %.
- Suitable aromatic structures are hydroquinone, resorcinol, 2,6-naphthalenediol, 1,8-naphthalenediol, bisphenol-A in the case of diols, and terephthalic acid, isophthalic acid, naphthalene-2,6-dicarboxylic acid in the case of dicarboxylic acids, an example of a heterocyclic aromatic dicarboxylic acid is 2,5-furandicarboxylic acid.
- Suitable hydroxycarboxylic acids are, for example, lactic acid, glycolic acid, 4-hydroxybutyric acid, 3-hydroxybutyric acid or 3-hydroxyvaleric acid, and a hydroxycarboxylic acid with aromatic components is mandelic acid.
- polyesters are, in particular, polybutylene terephthalate (PBT) and copolymers of 1,4-butanediol with terephthalic acid, adipic acid or sebacic acid.
- PBT polybutylene terephthalate
- copolymers of 1,4-butanediol with terephthalic acid, adipic acid or sebacic acid are preferred polyesters.
- Preferred polyamides are in particular polyamide 6, polyamide 6.6, blends of polyamide 6 with polyamide 6.6, polyamide 10.10, polyamide 10.12, polyamide 12.12, polyamide 11 and polyamide 12.
- compositions can contain other additives selected from the group consisting of secondary antioxidants, UV absorbers, light stabilizers, metal deactivators, filler deactivators, antiozonants, nucleating agents, antinucleating agents, impact modifiers, plasticizers, lubricants, rheology modifiers , thixotropic agents, chain extenders, processing aids, additives, flame retardants, pigments, dyes, optical brighteners, antimicrobial agents, antistatic agents, slip agents, antiblocking agents, coupling agents, crosslinking agents, anticrosslinking agents, hydrophilizing agents, hydrophobing agents, hydrolysis stabilizers, adhesion promoters, dispersing agents, compatibilizers, oxygen scavengers, acid scavengers, Blowing agents, degradation additives, defoaming aids, odor traps, marking agents, antifogging agents, fillers and reinforcing materials are used.
- additives selected from the group consisting of secondary antioxidants, UV absorbers, light stabilizer
- compositions contain, in particular, phosphites or phosphonites, fillers or acid scavengers.
- Suitable phenolic antioxidants are:
- Alkylated monophenols such as 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di -tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methyl-phenol, 2-( ⁇ -methylcyclohexyl)-4,6-dimethylphenol , 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethyl- phenol, linear or branched nonylphenols such as 2,6-dinonyl- 4-methyl-phenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-dimethyl-6-(
- alkylthiomethyl phenols such as 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol;
- Hydroquinones and alkylated hydroquinones such as 2,6-di-tert-butyl-4-methyloxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4 -octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl -4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxylphenyl)adipate;
- Tocopherols such as ⁇ -, ⁇ -, ⁇ -, ⁇ -tocopherol and mixtures of these (vitamin E); Hydroxylated thiodiphenyl ethers such as 2,2'-thiobis(6-tert-butyl-4-methyl-phenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl- 3-methyl- phenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-secamylphenol), 4,4'-bis( 2,6-dimethyl-4-hydroxyphenyl) disulfide;
- Hydroxylated thiodiphenyl ethers such as 2,2'-thiobis(6-tert-butyl-4-methyl-phenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl- 3-
- Alkylidenebisphenols such as 2,2'-methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl- 6-( ⁇ -methylcyclohexyl)phenol], 2,2'-methylenebis(4-methyl-6-cyclohexylphenol), 2,2'-methylenebis(6-nonyl-4-methylphenol), 2,2'-methylenebis(4 ,6-di-tert-butylphenol), 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2, 2'-methylenebis[6-(a-methylbenzyl)-4-nonylphenol], 2,2'-methylenebis[6-( ⁇ , ⁇ -dimethylbenzyl)-4-nonyl
- O-, N- and S-benzyl compounds such as 3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate , tridecyl 4-hydroxy-3,5-di-tert-butyl-benzyl-mercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy -2,6-dimethyl-benzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate;
- Hydroxybenzylated malonates such as dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, dioctadecyl-2-(3-tert-butyl-4-hydroxy-5-methyl-benzyl) malonate, didodecylmercaptoethyl 2,2-bis(3,5-di-tert-butyl-4-hydroxy-benzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2- bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate; Aromatic hydroxybenzyl compounds such as 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert- butyl-4-hydroxy-benzyl)-2,3,5,6-te
- Triazine compounds such as 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3 ,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxy-phenoxy) -1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3, 5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(
- Benzyl phosphonates such as dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl
- acylaminophenols such as 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate;
- Esters of ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with monohydric or polyhydric alcohols e.g. methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol , 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2
- Esters of ⁇ -(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with monohydric or polyhydric alcohols for example methanol, ethanol, n-octanol, i-octanol, octade- canol, 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]oc
- Esters of ⁇ -(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with monohydric or polyhydric alcohols e.g. methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2- Propanediol, Neopentyl Glycol, Thiodiethylene Glycol, Diethylene Glycol, Triethylene Glycol, Pentaerythritol, Tris-(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-
- Esters of (3,5-di-tert-butyl-4-hydroxyphenyl)acetic acid with monohydric or polyhydric alcohols e.g. methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;
- Amides of ⁇ -(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid such as N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N' - Bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'- Bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N'-
- vitamin C Ascorbic acid (vitamin C).
- Particularly preferred phenolic antioxidants are the following structures:
- n is an integer and is between 2 and 10.
- phenolic antioxidants are based on renewable raw materials phenolic antioxidants such.
- chrysin quercitin, hesperidin, neohesperidin, naringin, Morin, kaempferol, fisetin, datiscetin, luteolin, apigenin, taxifolin, isoflavones such as genistein, genistin, daidzein, daidzin, formononetin, anthocyanins such as delphinidin and malvidin, curcumin, carnosic acid, carnosol, rosmarinic acid, tannin and resveratrol and carotenoids with alcoholic groups, such as beta-cryptoxanthin, lutein, zeaxanthin or astaxanthin.
- alcoholic groups such as beta-cryptoxanthin, lutein, zeaxanthin or astaxanthin.
- Suitable aminic antioxidants are:
- Preferred amine antioxidants are: N,N'-diisopropyl-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-p-
- Particularly preferred aminic antioxidants are the structures:
- Preferred hydroxylamines or N-oxides are, for example, N,N-dialkylhydroxylamine, N,N-dibenzylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-distearylhydroxylamine, N-benzyl- ⁇ -phenylnitrone, N- Octadecyl-a-hexadecylnitrone, as well as Genox EP (SI Group) according to the formula:
- Suitable lactones are benzofuranones and indolinones such as 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-benzofur
- Preferred fillers are calcium carbonate, silicates, talc, mica, kaolin, metal oxides and metal hydroxides, carbon black, graphite, wood flour or fibers from natural products such as cellulose.
- Other suitable fillers are hydrotalcites or zeolites or phyllosilicates such as montmorillonite, bentonite, beidelite, mica, hectorite, saponite, vermiculite, ledikite, magadite, illite, kaolinite, wollastonite, attapulgite.
- Suitable secondary antioxidants are in particular phosphites or phosphonites such as e.g.
- Triphenyl phosphite diphenylalkyl phosphites, phenyldialkyl phosphites, tri(nonylphenyl) phosphite, trilauryl phosphites, trioctadecyl phosphite, distearylpentaerythritol diphosphite, tris-(2,4-di-tert-butylphenyl) phosphite, diisodecylpentaerythritol diphosphite, bis(2,4-di-tert -butylphenyl)pentaerythritol diphosphite, bis(2,4-di-cumylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, diisodecyloxy
- Particularly preferred phosphites are:
- a preferred phosphonite is:
- Suitable secondary antioxidants are also organo-sulphur compounds such as sulfides and disulfides, for example distearyl thiodipropionate, dilauryl thiodipropionate, ditridecyldithiopropionate, ditetradecyl thiodipropionate, 3-(dodecylthio)-, 1,1'-[2,2-bis[[3-(dodecylthio). )-1-oxopropoxy]methyl]-1,3-propanediyl]propanoic acid ester.
- organo-sulphur compounds such as sulfides and disulfides, for example distearyl thiodipropionate, dilauryl thiodipropionate, ditridecyldithiopropionate, ditetradecyl thiodipropionate, 3-(dodecylthio)-, 1,1'-[2,2-bis[
- Suitable acid scavengers are salts of mono, di, tri or tetravalent metals, preferably alkali metals, alkaline earth metals, aluminum or zinc, formed in particular with fatty acids, such as calcium stearate, magnesium stearate, zinc stearate, aluminum stearate, calcium laurate, Calcium behenate, calcium lactate, calcium stearoyl-2-lactate
- Suitable acid scavengers are hydrotalcites, in particular synthetic hydrotalcites based on aluminium, magnesium and zinc, hydrocalumites, zeolites, alkaline earth metal oxides, in particular calcium oxide and magnesium oxide as well as zinc oxide, alkaline earth metal carbonates, in particular calcium carbonate, magnesium carbonate and dolomite, and hydroxides, in particular brucite (magnesium hydroxide),
- Suitable co-stabilizers are also polyols, in particular alditols or cyclitols.
- Polyols are, for example, pentaerythritol, dipentaerythritol, tripentaerythritol, short-chain polyether polyols or polyester polyols, as well as 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 may be selected from the group consisting of inositol (myo, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi- and cis-inositol), 1,2 ,3,4-tetrahydroxycyclohexane, 1,2,3,4,5-pentahydroxycyclohexane, Quercitol, Viscumitol, Bornesitol, Conduritol, Ononitol, Pinitol, Pinpollitol, quebrachitol, ciceritol, quinic acid, shikimic acid and valienol, preference being given to myo-inositol (myo-inositol).
- inositol myo, scyllo-, D-chiro-, L-chiro-, muco-, neo-, allo-, epi- and cis-i
- Suitable light stabilizers are compounds based on 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, esters of benzoic acids, acrylates, oxamides and 2-(2-hydroxyphenyl)-1,3,5-triazines.
- 2-(2'-hydroxyphenyl)benzotriazoles examples include 2-(2'-hydroxy-5'methylphenyl)benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)benzotriazole , 2-(5'-tert-butyl-2'-hydroxyphenyl)benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3 ',5'-Di-tert-butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl-5-chlorobenzotriazole, 2-( 3'-sec-butyl-5'-tert-butyl-2'-hydroxy-phenyl)benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl)benzotriazo
- 2-hydroxybenzophenones 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy and 2'-hydroxy -4,4'-dimethyloxy derivatives of 2-hydroxybenzophenones.
- Suitable acrylates are ethyl ⁇ -cyano- ⁇ , ⁇ -diphenyl acrylate, isooctyl ⁇ -cyano- ⁇ , ⁇ -diphenyl acrylate, methyl ⁇ -carbomethoxycinnamate, methyl ⁇ -cyano- ⁇ -methyl-p-methoxycinnamate, butyl ⁇ -cyano- ⁇ -methyl-p-methoxycinnamate, methyl ⁇ -carbomethoxy-p-methoxycinnamate and N-( ⁇ -carbo-methoxy- ⁇ -cyanovinyl)-2-methylindoline.
- esters of benzoic acids are 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl-3,5-di-tert- butyl 4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxy-benzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6- di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.
- Suitable oxamides are 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'- di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and its mixtures with 2- ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.
- 2-(2-hydroxyphenyl)-1,3,5-triazines examples include 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy- 4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl) -1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy -4-octyloxyphenyl)-4,6-bis(4-methyl- phenyl-1,3,5-triazine, 2-(2-Hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethyl- phenyl)-1,
- suitable metal deactivators are N,N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4- hydroxy-phenyl-propionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyldihydrazide, oxanilide, isophthaloyldihydrazide, sebacoylbis- phenylhydrazide, N,N'-diacetyladipoyldihydrazide, N,N'-bis(salicyloyl) oxylyldihydrazide, N,N'-bis(salicyloyl)thiopropionyldihydrazide.
- metal deactivators are:
- Suitable low molecular weight hindered amines are 1,1-bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebazate, bis( 1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebazate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)-n-butyl-3,5-di-tert -butyl-4-hydroxy-benzylmalonate, the condensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensation products of N,N'-bis( 2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris(
- the structures given above also include the sterically hindered N-H, N-alkyl such as N-methyl or N-octyl, the N-alkoxy derivatives such as N-methoxy or N-octyloxy, the cycloalkyl derivatives such as N -cyclohexyloxy and the N-(2-hydroxy-2-methylpropoxy) analogs.
- Preferred low molecular weight hindered amines also have the following structures:
- Preferred oligomeric or polymeric hindered amines are:
- n is in each case from 3 to 100.
- Another suitable light stabilizer is Hostanox NOW (manufacturer: Clariant SE) with the following general structure: where R is -OC(O)-C 15 H 31 or -OC(O)-C 17 H 35 .
- the structures given 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.
- Suitable dispersing agents are:
- Polyacrylates e.g., copolymers with long-chain side groups, polyacrylate block copolymers, alkylamides: e.g., N,N'-1,2-ethanediylbisoctadecanamide sorbitan esters, e.g., monostearyl sorbitan esters, titanates and zirconates, reactive copolymers with functional groups, e.g., polypropylene-co-acrylic acid, Polypropylene-co-maleic anhydride, polyethylene-co-glycidyl methacrylate, polystyrene-alt-maleic anhydride-polysiloxanes: e.g.
- dimethylsilanediol-ethylene oxide copolymer polyphenylsiloxane copolymer, amphiphilic copolymers: e.g. polyethylene block polyethylene oxide, dendrimers, e.g. den - drimmer.
- Suitable antinucleating 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 , AlO(OH), MgCO 3 , phyllosilicates such as montmorillonite or sepiolite, unmodified or organically modified, double salts such as Mg-Al- Silicates, POSS (polyhedral oligomeric silsesquioxane) compounds, huntite, hydromagnesite or halloysite as well as 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, polyisocyanurate, allantoin, phosphacene, in particular melamine cyanurate, melamine phosphate, dimelamin phosphate,
- plasticizers examples include phthalic acid esters, adipic acid esters, citric acid esters, 1,2-cyclohexanedicarboxylic acid esters, trimellitic acid esters, isosorbide esters, phosphate esters, epoxides such as epoxidized soybean oil or aliphatic polyesters.
- Suitable lubricants and processing aids are, for example, polyethylene waxes, polypropylene waxes, salts of fatty acids such as calcium stearate, zinc stearate or salts of montan waxes, amide waxes such as erucic acid amide or oleic acid amides, fluoropolymers, silicones or neoalkoxy titanate and zirconates.
- Suitable pigments can be inorganic or organic in nature.
- Inorganic pigments are, for example, titanium dioxide, zinc oxide, zinc sulfide, iron oxide, ultramarine, carbon black, organic pigments are, for example, anthraquinones, anthanthrones, benzimidazolones, quinacridones, diketopyrrolopyrroles, dioxazines, indanthrones, isoindolinones, azo compounds, perylenes, phthalocyanines nine or pyranthrones.
- Other suitable pigments are metal-based effect pigments or metal-oxide-based pearlescent pigments.
- Suitable optical brighteners are, for example, bisbenzoxazoles, phenylcoumarins or bis(styryl)biphenyls and in particular optical brighteners of the formulas:
- Suitable filler deactivators are, for example, polysiloxanes, polyacrylates, in particular block copolymers such as polymethacrylic acid-polyalkylene oxide or polyglycidyl (meth)acrylates and their copolymers, for example with styrene, and epoxides, for example of the following structures:
- Suitable antistatic agents are ethoxylated alkylamines, fatty acid esters, alkylsulfonates and polymers such as polyetheramides.
- Suitable antiozonants are the amines mentioned above, such as N,N'-diisopropyl-p-phenylenediamine, N,N'-di-sec-butyl-p-phenylenediamine, N,N'-bis(1,4-dimethylpentyl) -p-phenylenediamine, N,N'-dicyclohexyl-p-phenylenedi- min, N-isopropyl-N'-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N'-phenyl -p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine.
- Suitable nucleating agents are talc, alkali metal or alkaline earth metal salts of mono- and polyfunctional carboxylic acids such as. benzoic acid, succinic acid, adipic acid, e.g ) phosphate, as well as trisamides and diamides such as e.g. propanamide) or 2,6-naphthalene dicarboxylic acid dicyclohexylamide.
- Suitable additives for increasing the molecular weight of polycondensation polymers are diepoxides, bis-oxazolines, bis-oxazolones, bis-oxazines, diisocyanates, dianhydrides, bis-acyllactams, bis-maleimides, dicyanates, carbodiimides.
- chain extenders are polymeric compounds such as, for example, polystyrene-polyacrylate-polyglycidyl (meth)acrylate copolymers, polystyrene-maleic anhydride copolymers and polyethylene-maleic anhydride copolymers.
- Suitable additives for increasing the electrical conductivity are, for example, the antistatic agents mentioned, 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 aluminum nitrides and boron nitrides.
- suitable infrared-active additives are aluminum silicates, hydrotalcites or dyes such as phthalocyanines or anthraquinones.
- suitable mold release agents are silicones, soaps and waxes such as montan waxes.
- the additive composition described above and any additional additives are incorporated into the plastic using conventional processing methods, with the polymer being melted and mixed with the additive composition according to the invention and any other additives, preferably using mixers, kneaders or extruders.
- Preferred processing machines are extruders such as, for example, single-screw extruders, twin-screw extruders, planetary roller extruders, ring extruders, co-kneaders, which are preferably equipped with vacuum degassing.
- the processing can take place under air or possibly under inert gas conditions.
- 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 compositions according to the invention in a polymer.
- the present invention relates to a molded part or a molded body that can be produced from a hydrolysis-stabilized composition according to the present invention.
- the molded part or molded body is selected from the group consisting of foils, films, foams, fibers, cables and pipes, profiles, hollow bodies, ribbons, membranes such as geomembranes, or adhesives, which are produced via extrusion, injection molding , blow molding, calendering, pressing processes, spinning processes, rotomoulding, e.g. for the electrical and electronics industry, construction industry, transport industry (car, plane, ship, train), for medical applications, for household and electrical appliances, vehicle parts, consumer goods , packaging, furniture, textiles.
- Hydrotalcite 1 Actilox CAH EXP 0213; Supplier: Nabaltec Hydrotalcite 2: DHT-4C; Supplier: Kisuma Chemicals, calcined version of
- Hydrotalcite 3 Hycite 713; Supplier: Clariant SE
- Hydrotalcite 4 Sorbacid 911; Supplier: Clariant SE
- Hydrotalcite 5 DHT-4A; Supplier: Kisuma Chemicals
- AlfaAesar type 13X molecular sieve was used as the zeolite.
- the aziridine is the POLY-U Powder from the manufacturer Menadiona.
- the chemical name is N,N'-(methylenedi-p-phenylene)bis(aziridine-1-carboxamide).
- a polylactide (PLA) (Luminy L130, supplier: Total Corbion) was tested together with the additives specified in Table 1 at a maximum of 200° C. in a twin-screw extruder (Process 11, manufacturer ThermoScientific) at a throughput of 800 g/h.
- Polymer and additives were dried overnight in a vacuum dryer before processing. After compounding, the compounds were aged in deionized water at 60 °C in a heating cabinet for 2 weeks (336 hours). After aging, the samples were dried overnight and the MVR determined (190 °C / 2.16 kg).
- a polybutylene terephthalate (PBT) (Pocan B1204, supplier: Lanxess) was extruded together with the additives specified in Table 2 at a maximum of 245° C. in a twin-screw extruder (Process 11, manufacturer ThermoScientific) at a throughput of 800 g/h.
- Polymer and additives were dried overnight in a vacuum dryer before processing. After compounding, the compounds were aged at 85°C in an oven for 2 weeks (336 hours) in deionized water. After aging, the samples were dried overnight and the MVR was determined (250 °C / 2.16 kg).
- a polyamide 6 (PA6) (Ultramid B27E, supplier: BASF) was combined with the additives specified in Table 3 at a maximum of 245° C. in a microcompounder (Micro 5cc Twin Screw Extruder, manufacturer DSM) compounded. Polymer and additives were dried overnight in a vacuum dryer before processing. After compounding, the compounds were aged at 85°C in an oven for 2 weeks (336 hours) in deionized water. After aging, the samples were dried overnight and the molecular weight determined by GPC.
- PA6 Ultramid B27E, supplier: BASF
- the MVR is a measure of the molecular weight of the polymer. The higher the MVR, the lower the molecular weight and thus the degradation of the polymer by hydrolysis that has taken place. The lower the MVR increase, the higher the hydrolytic stability. The combinations according to the invention therefore exhibit excellent hydrolytic stability.
Abstract
Description
Claims
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JP2023553994A JP2024510155A (ja) | 2021-03-17 | 2022-03-17 | 安定剤組成物、安定剤組成物の使用、縮合ポリマーを加水分解による分解に対して安定化させるための方法、及び加水分解安定化された組成物、及びそれから得られる成形品又は成形部品 |
CN202280022459.4A CN117015566A (zh) | 2021-03-17 | 2022-03-17 | 稳定剂组合物、稳定剂组合物的用途、用于稳定缩聚物以防止其水解降解的方法、以及水解稳定的组合物及其模塑品或模塑件 |
EP22716213.8A EP4308642A1 (de) | 2021-03-17 | 2022-03-17 | Stabilisator-zusammensetzung, verwendung der stabilisator-zusammensetzung, verfahren zur stabilisierung von kondensationspolymeren gegen hydrolytischen abbau sowie hydrolysestabilisierte zusammensetzung und formkörper oder formteil hieraus |
KR1020237035322A KR20230158068A (ko) | 2021-03-17 | 2022-03-17 | 안정제 조성물, 안정제 조성물의 용도, 가수분해에 대한 축합 중합체의 안정화 방법, 및 가수분해 안정화 조성물 및 이로부터의 성형된 물품 또는 성형된 부품 |
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DE102021202598A1 (de) | 2022-09-22 |
EP4308642A1 (de) | 2024-01-24 |
JP2024510155A (ja) | 2024-03-06 |
KR20230158068A (ko) | 2023-11-17 |
CN117015566A (zh) | 2023-11-07 |
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