IE43555B1 - Plastics compositions containing polar phenolic antioxidants - Google Patents

Plastics compositions containing polar phenolic antioxidants

Info

Publication number: IE43555B1
Authority: IE; Ireland
Prior art keywords: plastics; bis; carbon atoms; alkyl; acid
Prior art date: 1975-10-02

Application number

IE2169/76A

Other languages

English (en)

Other versions

IE43555L (en

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1975-10-02

Filing date

1976-10-01

Publication date

1981-03-25

1976-10-01 Application filed by Hoechst Ag filed Critical Hoechst Ag

1977-04-02 Publication of IE43555L publication Critical patent/IE43555L/xx

1981-03-25 Publication of IE43555B1 publication Critical patent/IE43555B1/en

Links

229920003023 plastic Polymers 0.000 title claims abstract description 26
239000004033 plastic Substances 0.000 title claims abstract description 26
239000000203 mixture Substances 0.000 title claims abstract description 12
239000002530 phenolic antioxidant Substances 0.000 title abstract description 5
-1 rare earth metal cation Chemical class 0.000 claims abstract description 22
239000003381 stabilizer Substances 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
150000001768 cations Chemical class 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 8
150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 6
150000001412 amines Chemical class 0.000 claims abstract description 5
150000001336 alkenes Chemical class 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
230000000737 periodic effect Effects 0.000 claims abstract description 4
229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 4
229910052723 transition metal Inorganic materials 0.000 claims abstract description 4
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
239000000463 material Substances 0.000 claims description 14
229920000642 polymer Polymers 0.000 claims description 7
229920000098 polyolefin Polymers 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
229910000329 aluminium sulfate Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
159000000013 aluminium salts Chemical class 0.000 claims description 2
150000003839 salts Chemical class 0.000 abstract description 30
239000003963 antioxidant agent Substances 0.000 abstract description 6
239000004743 Polypropylene Substances 0.000 abstract description 5
229920001155 polypropylene Polymers 0.000 abstract description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract description 3
230000006641 stabilisation Effects 0.000 abstract 1
238000011105 stabilization Methods 0.000 abstract 1
239000002253 acid Substances 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
230000008018 melting Effects 0.000 description 9
238000002844 melting Methods 0.000 description 9
150000002148 esters Chemical class 0.000 description 8
239000011701 zinc Substances 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
230000000087 stabilizing effect Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000011575 calcium Substances 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 3
239000004593 Epoxy Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001735 carboxylic acids Chemical group 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
229920005862 polyol Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
VKOUCJUTMGHNOR-UHFFFAOYSA-N Diphenolic acid Chemical compound C=1C=C(O)C=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C=C1 VKOUCJUTMGHNOR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
229920001328 Polyvinylidene chloride Polymers 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
VMNKHSPZIGIPLL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] dihydrogen phosphite Chemical compound OCC(CO)(CO)COP(O)O VMNKHSPZIGIPLL-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000003925 fat Substances 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000011133 lead Substances 0.000 description 2
239000004611 light stabiliser Substances 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
238000000034 method Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
239000005033 polyvinylidene chloride Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
229910052712 strontium Inorganic materials 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
VWRFVLCNPQJMAJ-UHFFFAOYSA-N 1,2,3-triaza-5-phosphatricyclo[3.3.1.13,7]decane Chemical compound C1C2CN3CP(C2)CN1N3 VWRFVLCNPQJMAJ-UHFFFAOYSA-N 0.000 description 1
TZVXUYAWDQEGRA-UHFFFAOYSA-N 1,2-diazatricyclo[3.3.1.13,7]decane Chemical class C1C(N2)CC3CC1CN2C3 TZVXUYAWDQEGRA-UHFFFAOYSA-N 0.000 description 1
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 1
KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 description 1
DHBPAQUDNKLCEJ-UHFFFAOYSA-N 2-hydroxybenzoic acid;phenol Chemical class OC1=CC=CC=C1.OC(=O)C1=CC=CC=C1O DHBPAQUDNKLCEJ-UHFFFAOYSA-N 0.000 description 1
ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical class OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
ZLFHNCHMEGLFKL-UHFFFAOYSA-N 3,3-bis(3-tert-butyl-4-hydroxyphenyl)butanoic acid Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(CC(O)=O)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 ZLFHNCHMEGLFKL-UHFFFAOYSA-N 0.000 description 1
PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004709 Chlorinated polyethylene Substances 0.000 description 1
229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
239000003490 Thiodipropionic acid Substances 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000005396 acrylic acid ester group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000004411 aluminium Chemical class 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical class [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
229940089960 chloroacetate Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
FGFJYALWOJLWQR-UHFFFAOYSA-N cyclohexanone;propanoic acid Chemical compound CCC(O)=O.O=C1CCCCC1 FGFJYALWOJLWQR-UHFFFAOYSA-N 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
229950010286 diolamine Drugs 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000012760 heat stabilizer Substances 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052745 lead Inorganic materials 0.000 description 1
239000000944 linseed oil Substances 0.000 description 1
235000021388 linseed oil Nutrition 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229920006113 non-polar polymer Polymers 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical class [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
PWYYWQHXAPXYMF-UHFFFAOYSA-N strontium(2+) Chemical compound [Sr+2] PWYYWQHXAPXYMF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003784 tall oil Substances 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical class C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
- 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
- C08K5/13—Phenols; Phenolates
- C08K5/138—Phenolates

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Compositions Of Macromolecular Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IE2169/76A 1975-10-02 1976-10-01 Plastics compositions containing polar phenolic antioxidants IE43555B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19752544014 DE2544014A1 (de)	1975-10-02	1975-10-02	Polare phenolische antioxidantien zur stabilisierung von kunststoffen

Publications (2)

Publication Number	Publication Date
IE43555L IE43555L (en)	1977-04-02
IE43555B1 true IE43555B1 (en)	1981-03-25

Family

ID=5958078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE2169/76A IE43555B1 (en)	1975-10-02	1976-10-01	Plastics compositions containing polar phenolic antioxidants

Country Status (11)

Country	Link
JP (1)	JPS5246038A (it)
BE (1)	BE846925A (it)
CA (1)	CA1055521A (it)
DE (1)	DE2544014A1 (it)
DK (1)	DK444676A (it)
FR (1)	FR2326442A1 (it)
GB (1)	GB1521567A (it)
IE (1)	IE43555B1 (it)
IT (1)	IT1070813B (it)
LU (1)	LU75917A1 (it)
NL (1)	NL7610693A (it)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5624418A (en) *	1979-08-08	1981-03-09	Toray Ind Inc	Preparation of polyester
CA1325217C (en) *	1983-11-07	1993-12-14	John T. Lai	3,5-dialkyl-4-hydroxyphenyl-substituted derivatives
FR2573084B1 (fr) *	1984-11-14	1987-02-20	Rhone Poulenc Spec Chim	Compositions a base de polyolefines contenant un chelate de cuivre et un phosphite organique
JPS63267365A (ja) *	1987-04-24	1988-11-04	Terumo Corp	ホロ−フアイバ−型人工臓器の製造方法
US5356546A (en) *	1992-04-16	1994-10-18	The Lubrizol Corporation	Metal salts useful as additives for fuels and lubricants
CN115819238A (zh) *	2020-03-26	2023-03-21	优禘股份有限公司	一种低迁移受阻酚抗氧化合物、制备方法及组合物
DE102020203988A1 (de) *	2020-03-27	2021-09-30	Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein	Verwendung von Hydroxyzimtsäuresalzen zur Stabilisierung von organischen Materialien, stabilisiertes organisches Material, Verfahren zur Stabilisierung von organischen Materialien, spezifische Stabilisatoren sowie Stabilisatorzusammensetzungen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH387657A (de) *	1958-07-08	1965-02-15	Bayer Ag	Verfahren zur Herstellung von 3,5,3',5'-tetrasubstituierten 4,4'-Dihydroxydiphenylmethincarbonsäuresalzen
US3723489A (en) *	1971-02-25	1973-03-27	Ciba Geigy Corp	Metal derivatives of 3,5-di-t-butyl-4-hydroxyphenyl propionic acid
GB1396875A (en) *	1971-07-27	1975-06-11	Ici Ltd	Hydroxyaryl carboxylic acids and esters thereof and their use as antioxidants

1975
- 1975-10-02 DE DE19752544014 patent/DE2544014A1/de not_active Withdrawn
1976
- 1976-09-27 NL NL7610693A patent/NL7610693A/xx not_active Application Discontinuation
- 1976-09-30 GB GB40613/76A patent/GB1521567A/en not_active Expired
- 1976-09-30 IT IT27868/76A patent/IT1070813B/it active
- 1976-09-30 JP JP51116698A patent/JPS5246038A/ja active Pending
- 1976-10-01 IE IE2169/76A patent/IE43555B1/en unknown
- 1976-10-01 LU LU75917A patent/LU75917A1/xx unknown
- 1976-10-01 DK DK444676A patent/DK444676A/da not_active Application Discontinuation
- 1976-10-01 CA CA262,543A patent/CA1055521A/en not_active Expired
- 1976-10-04 FR FR7629762A patent/FR2326442A1/fr not_active Withdrawn
- 1976-10-04 BE BE171224A patent/BE846925A/xx unknown

Also Published As

Publication number	Publication date
JPS5246038A (en)	1977-04-12
LU75917A1 (it)	1977-05-11
NL7610693A (nl)	1977-04-05
BE846925A (fr)	1977-04-04
DE2544014A1 (de)	1977-04-14
CA1055521A (en)	1979-05-29
IE43555L (en)	1977-04-02
FR2326442A1 (fr)	1977-04-29
GB1521567A (en)	1978-08-16
DK444676A (da)	1977-04-03
IT1070813B (it)	1985-04-02

Publication	Publication Date	Title
EP0165209B1 (de)	1989-07-19	o,p-Bifunktionalisierte, o'-substituierte Phenole
US2944086A (en)	1960-07-05	1, 1-bis(3, 5-dialkyl-4-hydroxyphenyl) methanes
US4963594A (en)	1990-10-16	Heat/color stabilized polymers of vinyl chloride
US4870214A (en)	1989-09-26	Antioxidant
US3839506A (en)	1974-10-01	Hindered phenol pentaerythritol phosphonate
US3737485A (en)	1973-06-05	Tripentaerythritol tetraphosphite
US3364250A (en)	1968-01-16	Methyl beta-(3, 5-di-tert-butyl-4-hydroxyphenyl) propionate
EP0092497B1 (en)	1987-01-07	Synergistic antioxidant mixtures
KR910008056A (ko)	1991-05-30	안정화된 염소-함유 중합체 조성물
CA1190036A (en)	1985-07-09	Phosphoric acid compounds as co-stabilisers for me(ii)-carboxylates and/or me(ii)-phenolates in pvc
CA1055521A (en)	1979-05-29	Polar phenolic antioxidants for the stabilization of plastics
JPH10231407A (ja)	1998-09-02	食品接触及び医療グレードのｐｖｃ用安定化剤
CA1304868C (en)	1992-07-07	Thermoplastics stabilized against the action of light
US3678095A (en)	1972-07-18	Substituted derivatives of malonic acid useful as stabilizers
US3655832A (en)	1972-04-11	Polycarbocyclic phenolic phosphites
GB1563287A (en)	1980-03-26	Cyclopentyl substituted methylene bisphenols and their use as antioxidants
US4539354A (en)	1985-09-03	Stabilized ethylene/chlorotrifluoroethylene copolymer composition
US4340514A (en)	1982-07-20	Non-toxic liquid stabilizer for halogenated hydrocarbon resins and process for stabilizing such resins
US4081475A (en)	1978-03-28	Trialkylsubstituted hydroxybenzyl malonates and stabilized compositions
US3702837A (en)	1972-11-14	Hydroxyphenylalkyleneyl isocyanurate synergist combinations
CA1073923A (en)	1980-03-18	Salicylic acid derivatives
CA1326681C (en)	1994-02-01	Substituted phenols and their use as stabilizers
US3897388A (en)	1975-07-29	Antioxidant comprising a hydroxy aromatic compound containing sulfur and organic phosphite
US3396130A (en)	1968-08-06	Organic triphosphites and synthetic resin compositions containing the same
US3657321A (en)	1972-04-18	4 4'-alkylidene-diphenol-bis-(di-t-butyl-4'''-hydroxyphenyl) alkanoates