DE2545292C3 - Azaadamantanverbindungen als Stabilisatoren für organische Polymerisatzusammensetzungen - Google Patents
Azaadamantanverbindungen als Stabilisatoren für organische PolymerisatzusammensetzungenInfo
- Publication number
- DE2545292C3 DE2545292C3 DE2545292A DE2545292A DE2545292C3 DE 2545292 C3 DE2545292 C3 DE 2545292C3 DE 2545292 A DE2545292 A DE 2545292A DE 2545292 A DE2545292 A DE 2545292A DE 2545292 C3 DE2545292 C3 DE 2545292C3
- Authority
- DE
- Germany
- Prior art keywords
- group
- polymer
- atom
- hydrogen atom
- azaadamantane
- 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.)
- Expired
Links
- WENISBCJPGSITQ-UHFFFAOYSA-N 1-azatricyclo[3.3.1.13,7]decane Chemical class C1C(C2)CC3CC1CN2C3 WENISBCJPGSITQ-UHFFFAOYSA-N 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title claims description 8
- 239000003381 stabilizer Substances 0.000 title description 20
- 229920000620 organic polymer Polymers 0.000 title description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- -1 phosphoryl group Chemical group 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 229920001059 synthetic polymer Polymers 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229920000098 polyolefin Polymers 0.000 claims description 6
- 230000000087 stabilizing effect Effects 0.000 claims description 6
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 4
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 239000005033 polyvinylidene chloride Substances 0.000 description 4
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FXXRPTKTLVHPAR-UHFFFAOYSA-N 1,3,5-triaza-7-phosphaadamantane Chemical compound C1N(C2)CN3CN1CP2C3 FXXRPTKTLVHPAR-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 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
- 239000002253 acid Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 150000001565 benzotriazoles Chemical class 0.000 description 2
- 229910052793 cadmium Chemical class 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical class [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000001782 photodegradation Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- GPOGLVDBOFRHDV-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)O GPOGLVDBOFRHDV-UHFFFAOYSA-N 0.000 description 1
- BPHLLGJNQPYNDP-UHFFFAOYSA-N 1,3,5-triaza-7-phosphaadamantane 7-oxide Chemical compound C1N(C2)CN3CN2CP1(=O)C3 BPHLLGJNQPYNDP-UHFFFAOYSA-N 0.000 description 1
- IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 1
- JHDKQAQKZPYXGT-UHFFFAOYSA-N 2,2-bis(3-tert-butyl-4-hydroxyphenyl)butanoic acid Chemical compound C=1C=C(O)C(C(C)(C)C)=CC=1C(C(O)=O)(CC)C1=CC=C(O)C(C(C)(C)C)=C1 JHDKQAQKZPYXGT-UHFFFAOYSA-N 0.000 description 1
- JEYHANFMWMDEPL-UHFFFAOYSA-N 2,6-bis-(4-methylphenyl)sulfonyl-2,6-diazatricyclo[3.3.1.13,7]decane Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2CC(N3S(=O)(=O)C=4C=CC(C)=CC=4)CC1CC3C2 JEYHANFMWMDEPL-UHFFFAOYSA-N 0.000 description 1
- YVNBVXTZGKSZLV-UHFFFAOYSA-N 2,6-diazatricyclo[3.3.1.13,7]decane Chemical compound C1C(N2)CC3CC2CC1N3 YVNBVXTZGKSZLV-UHFFFAOYSA-N 0.000 description 1
- AKUWZGOYTBCYAE-UHFFFAOYSA-N 2,6-dihydroxy-2,6-diazatricyclo[3.3.1.13,7]decane Chemical compound C1C(N2O)CC3N(O)C1CC2C3 AKUWZGOYTBCYAE-UHFFFAOYSA-N 0.000 description 1
- XQZSBXGEQVOISG-UHFFFAOYSA-N 2,6-dimethyl-2,6-diazatricyclo[3.3.1.13,7]decane Chemical compound C1C(N2C)CC3N(C)C1CC2C3 XQZSBXGEQVOISG-UHFFFAOYSA-N 0.000 description 1
- ASVYVGULTXXNKB-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyl-2-azatricyclo[3.3.1.13,7]decane Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C2)CC3CC2CC1C3 ASVYVGULTXXNKB-UHFFFAOYSA-N 0.000 description 1
- ZLSDEVRDASOICE-UHFFFAOYSA-N 2-azaadamantane Chemical compound C1C(N2)CC3CC1CC2C3 ZLSDEVRDASOICE-UHFFFAOYSA-N 0.000 description 1
- SFKPKRNMAQJGTL-UHFFFAOYSA-N 2-benzyl-6-methyl-2,6-diazatricyclo[3.3.1.13,7]decane Chemical compound CN1C(C2)CC3CC1CC2N3CC1=CC=CC=C1 SFKPKRNMAQJGTL-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
- KWTRRXDFJUGAHM-UHFFFAOYSA-N 2-hydroxy-2,6-diazatricyclo[3.3.1.13,7]decane Chemical compound C1C(N2)CC3N(O)C1CC2C3 KWTRRXDFJUGAHM-UHFFFAOYSA-N 0.000 description 1
- NIYOVKMGBKJDDO-UHFFFAOYSA-N 2-hydroxy-6-methyl-2,6-diazatricyclo[3.3.1.13,7]decane Chemical compound C1C(N2O)CC3N(C)C1CC2C3 NIYOVKMGBKJDDO-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
- LUQRPHRPONSIJV-UHFFFAOYSA-N 2-methyl-2,6-diazatricyclo[3.3.1.13,7]decane Chemical compound C1C(N2)CC3N(C)C1CC2C3 LUQRPHRPONSIJV-UHFFFAOYSA-N 0.000 description 1
- UGDYSCSSQAEHGD-UHFFFAOYSA-N 2-thia-1,3,5-triaza-7-phosphaadamantane 2,2-dioxide Chemical compound C1N(C2)CN3S(=O)(=O)N1CP2C3 UGDYSCSSQAEHGD-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
- 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
- WXMJWQSOWLXJOA-UHFFFAOYSA-N 7-amino-1,3,5-triazaadamantane Chemical compound C1N(C2)CN3CN2CC1(N)C3 WXMJWQSOWLXJOA-UHFFFAOYSA-N 0.000 description 1
- LPPLVTOEOMJNPS-UHFFFAOYSA-N 7-nitro-1,3,5-triazaadamantane Chemical compound C1N(C2)CN3CN2CC1([N+](=O)[O-])C3 LPPLVTOEOMJNPS-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- GDFBWYPDDMNUBA-UHFFFAOYSA-N N-butyl-1,3,5-triazatricyclo[3.3.1.13,7]decan-7-amine Chemical compound C1N(C2)CN3CN2CC1(NCCCC)C3 GDFBWYPDDMNUBA-UHFFFAOYSA-N 0.000 description 1
- TUTJFXMZANNBCP-UHFFFAOYSA-N N-heptyl-1,3,5-triazatricyclo[3.3.1.13,7]decan-7-amine Chemical compound C1N(C2)CN3CN2CC1(NCCCCCCC)C3 TUTJFXMZANNBCP-UHFFFAOYSA-N 0.000 description 1
- YQEMFALFYWEEDU-UHFFFAOYSA-N N-hexyl-1,3,5-triazatricyclo[3.3.1.13,7]decan-7-amine Chemical compound C1N(C2)CN3CN2CC1(NCCCCCC)C3 YQEMFALFYWEEDU-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- UWYKIOBACKWXBD-UHFFFAOYSA-N ac1l8q03 Chemical compound C1N(C2)CN3CN2CC1(NCCC)C3 UWYKIOBACKWXBD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 229960003805 amantadine Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- YJHQSBJFMDFVKK-UHFFFAOYSA-N benzene-1,2-diol;benzoic acid Chemical class OC1=CC=CC=C1O.OC(=O)C1=CC=CC=C1 YJHQSBJFMDFVKK-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 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
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 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
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000000344 soap 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
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004711 α-olefin Substances 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/50—Phosphorus bound to carbon only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3495—Six-membered rings condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2545292A DE2545292C3 (de) | 1975-10-09 | 1975-10-09 | Azaadamantanverbindungen als Stabilisatoren für organische Polymerisatzusammensetzungen |
| NL7610963A NL7610963A (nl) | 1975-10-09 | 1976-10-04 | Azaaedamantaanverbindingen als stabilisatoren voor organische polymeerpreparaten. |
| US05/729,483 US4082723A (en) | 1975-10-09 | 1976-10-04 | Aza-adamantane compound stabilizers for organic polymer compositions |
| CH1266876A CH629233A5 (de) | 1975-10-09 | 1976-10-06 | Verwendung von azaadamantanverbindungen zum stabilisieren von kunststoff-formmassen. |
| GB41721/76A GB1536297A (en) | 1975-10-09 | 1976-10-07 | Aza-adamantane stabilizers for synthetic polymer compositions |
| IT28106/76A IT1068553B (it) | 1975-10-09 | 1976-10-07 | Composti azaadamantanici come stabilizzanti per composizioni di polimeri organici |
| LU75952A LU75952A1 (enExample) | 1975-10-09 | 1976-10-07 | |
| IE2220/76A IE44175B1 (en) | 1975-10-09 | 1976-10-08 | Aza-adamantane compound stabilizers for organic polymer compositions |
| DK454776A DK454776A (da) | 1975-10-09 | 1976-10-08 | Anvendelse af azaadamantanforbindelser til stabilisering af kunststof formmasser mod lys-og varmenedbrydning stabilliseret kunststof formmasse samt fremgangsmade til stabilisering af kunststof mod indvirkning af lys og varme |
| CA263,205A CA1085085A (en) | 1975-10-09 | 1976-10-08 | Aza-adamantane compound stabilizers for organic polymer compositions |
| JP51120493A JPS5247041A (en) | 1975-10-09 | 1976-10-08 | Compositions for synthetic resin molding |
| FR7630488A FR2327277A1 (fr) | 1975-10-09 | 1976-10-11 | Utilisation de derives d'aza-adamantanes pour stabiliser des matieres polymeres |
| BE171405A BE847157A (fr) | 1975-10-09 | 1976-10-11 | Utilisation de derives d'aza-adamantanes pour stabiliser des matieres polymeres, |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2545292A DE2545292C3 (de) | 1975-10-09 | 1975-10-09 | Azaadamantanverbindungen als Stabilisatoren für organische Polymerisatzusammensetzungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2545292A1 DE2545292A1 (de) | 1977-04-14 |
| DE2545292B2 DE2545292B2 (de) | 1979-09-06 |
| DE2545292C3 true DE2545292C3 (de) | 1980-05-29 |
Family
ID=5958768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2545292A Expired DE2545292C3 (de) | 1975-10-09 | 1975-10-09 | Azaadamantanverbindungen als Stabilisatoren für organische Polymerisatzusammensetzungen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4082723A (enExample) |
| JP (1) | JPS5247041A (enExample) |
| BE (1) | BE847157A (enExample) |
| CA (1) | CA1085085A (enExample) |
| CH (1) | CH629233A5 (enExample) |
| DE (1) | DE2545292C3 (enExample) |
| DK (1) | DK454776A (enExample) |
| FR (1) | FR2327277A1 (enExample) |
| GB (1) | GB1536297A (enExample) |
| IE (1) | IE44175B1 (enExample) |
| IT (1) | IT1068553B (enExample) |
| LU (1) | LU75952A1 (enExample) |
| NL (1) | NL7610963A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7049374B2 (en) | 2002-07-18 | 2006-05-23 | Chevron U.S.A. Inc. | Heterodiamondoids |
| US7312562B2 (en) | 2004-02-04 | 2007-12-25 | Chevron U.S.A. Inc. | Heterodiamondoid-containing field emission devices |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2616799A1 (de) * | 1976-04-15 | 1977-10-20 | Hoechst Ag | Substituierte triazaadamantanverbindungen, ihre herstellung und verwendung |
| DE2702205A1 (de) * | 1977-01-20 | 1978-07-27 | Hoechst Ag | N-substituierte triazaadamantanylharnstoffe als stabilisatoren fuer thermoplaste |
| US5019660A (en) * | 1990-01-30 | 1991-05-28 | Mobil Oil Corporation | Diamondoid polymeric compositions |
| US5053568A (en) * | 1990-11-15 | 1991-10-01 | Mobil Oil Corp. | Lubricant compositions comprising copolymers of 1-vinyladamantane and 1-alkenes and methods of preparing the same |
| DE4205450C2 (de) * | 1992-02-22 | 1996-04-18 | Du Pont Deutschland | Photothermographisches Aufzeichnungsmaterial |
| US5367097A (en) * | 1993-06-03 | 1994-11-22 | Mobil Oil Corporation | Lubricant composition and method for increasing diamondoid incorporation in polyalphaolefin-containing lubricant |
| US5345020A (en) * | 1993-06-03 | 1994-09-06 | Mobil Oil Corporation | Method for making diamondoid lubricant base stock by alkylation with an olefin in the presence of a Lewis acid |
| NL1005254C2 (nl) * | 1997-02-12 | 1998-08-13 | Dsm Nv | Kunststofsamenstelling met een verbeterde weersbestendigheid. |
| NL1009844C2 (nl) * | 1998-08-12 | 2000-02-15 | Dsm Nv | Kunststofsamenstelling met een verbeterde weersbestendigheid. |
| US7402835B2 (en) | 2002-07-18 | 2008-07-22 | Chevron U.S.A. Inc. | Heteroatom-containing diamondoid transistors |
| US7224532B2 (en) | 2002-12-06 | 2007-05-29 | Chevron U.S.A. Inc. | Optical uses diamondoid-containing materials |
| US7186853B2 (en) * | 2003-06-05 | 2007-03-06 | Crompton Corporation | Polymer compositions containing stabilizer compounds comprising tricyclodecylmethyl groups |
| CN102804481B (zh) | 2009-06-19 | 2015-05-20 | 松下电器产业株式会社 | 光电元件 |
| ES2627009B2 (es) * | 2016-01-26 | 2018-01-22 | Universidad De Almería | Aditivacion de resinas epoxi mediante complejos poliméricos homo y heterometálicos con 1,3,5-triaza-7-fosfaadamantanofosfina (PTA) y 3,7-dimetil-1,3,7-triaza-5-phosphabiciclo[3.3.1]nonane (dmoPTA) |
| KR102488018B1 (ko) * | 2017-09-26 | 2023-01-13 | 삼성디스플레이 주식회사 | 다환 화합물 및 이를 포함하는 유기 전계 발광 소자 |
| DE102020205096A1 (de) | 2020-04-22 | 2021-10-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verwendung von Hydroxycarbonsäuresalzen zur Stabilisierung von thermoplastischen Kondensationspolymeren, stabilisierte Formmasse und hieraus hergestellte Formmassen und Formteile |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3812065A (en) * | 1971-11-22 | 1974-05-21 | Tenneco Chem | Surface-coating compositions containing n-(substituted indazolyl-n1-methyl)hexamethylenetetraamonium halides |
| US3879396A (en) * | 1973-12-28 | 1975-04-22 | Ciba Geigy Corp | Bicyclic hindered amino acids and metal salts thereof |
| US3883477A (en) * | 1973-12-28 | 1975-05-13 | Ciba Geigy Corp | Compositions stabilized with 1,4-disubstituted-7-azabicyclo (2.2.1) heptane-2,5 or 2, 6-dicarboxylic acid esters |
| US3912742A (en) * | 1974-01-14 | 1975-10-14 | Ciba Geigy Corp | Acylated derivatives of 2,6-dihydroxy-9-azabicyclo (3.3.1)nonane |
| DE2634957C3 (de) * | 1976-08-04 | 1980-10-02 | Hoechst Ag, 6000 Frankfurt | l-Oxa-4,8-diaza-spiro- [43] -decane, ihre Herstellung und ihre Verwendung als Lichtschutzmittel |
-
1975
- 1975-10-09 DE DE2545292A patent/DE2545292C3/de not_active Expired
-
1976
- 1976-10-04 US US05/729,483 patent/US4082723A/en not_active Expired - Lifetime
- 1976-10-04 NL NL7610963A patent/NL7610963A/xx not_active Application Discontinuation
- 1976-10-06 CH CH1266876A patent/CH629233A5/de not_active IP Right Cessation
- 1976-10-07 LU LU75952A patent/LU75952A1/xx unknown
- 1976-10-07 GB GB41721/76A patent/GB1536297A/en not_active Expired
- 1976-10-07 IT IT28106/76A patent/IT1068553B/it active
- 1976-10-08 IE IE2220/76A patent/IE44175B1/en unknown
- 1976-10-08 DK DK454776A patent/DK454776A/da not_active Application Discontinuation
- 1976-10-08 CA CA263,205A patent/CA1085085A/en not_active Expired
- 1976-10-08 JP JP51120493A patent/JPS5247041A/ja active Pending
- 1976-10-11 FR FR7630488A patent/FR2327277A1/fr active Granted
- 1976-10-11 BE BE171405A patent/BE847157A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7049374B2 (en) | 2002-07-18 | 2006-05-23 | Chevron U.S.A. Inc. | Heterodiamondoids |
| US7312562B2 (en) | 2004-02-04 | 2007-12-25 | Chevron U.S.A. Inc. | Heterodiamondoid-containing field emission devices |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1068553B (it) | 1985-03-21 |
| GB1536297A (en) | 1978-12-20 |
| DE2545292A1 (de) | 1977-04-14 |
| NL7610963A (nl) | 1977-04-13 |
| FR2327277A1 (fr) | 1977-05-06 |
| LU75952A1 (enExample) | 1977-05-25 |
| CH629233A5 (de) | 1982-04-15 |
| JPS5247041A (en) | 1977-04-14 |
| DE2545292B2 (de) | 1979-09-06 |
| BE847157A (fr) | 1977-04-12 |
| DK454776A (da) | 1977-04-10 |
| CA1085085A (en) | 1980-09-02 |
| IE44175B1 (en) | 1981-09-09 |
| US4082723A (en) | 1978-04-04 |
| FR2327277B1 (enExample) | 1980-06-06 |
| IE44175L (en) | 1977-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |