CA1041509A - Derives de la piperidine - Google Patents

Derives de la piperidine

Info

Publication number: CA1041509A
Authority: CA; Canada
Prior art keywords: residue; carbon atoms; parts; hydrogen; formula
Prior art date: 1972-04-21
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

Application number

CA264,259A

Other languages

English (en)

Inventor

Barry Cook

James Jack

Alexander M. Chalmers

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy 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.)

1972-04-21

Filing date

1976-10-27

Publication date

1978-10-31

1972-04-21 Priority claimed from GB1855872A external-priority patent/GB1393551A/en

1976-10-27 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1978-10-31 Application granted granted Critical

1978-10-31 Publication of CA1041509A publication Critical patent/CA1041509A/fr

Status Expired legal-status Critical Current

Links

150000003053 piperidines Chemical class 0.000 title abstract 2
229920000642 polymer Polymers 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims description 61
229910052739 hydrogen Inorganic materials 0.000 claims description 61
150000001875 compounds Chemical class 0.000 claims description 55
125000004432 carbon atom Chemical group C* 0.000 claims description 53
239000000203 mixture Substances 0.000 claims description 44
229910052757 nitrogen Inorganic materials 0.000 claims description 36
229910052799 carbon Inorganic materials 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
230000006866 deterioration Effects 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
229920000098 polyolefin Polymers 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
125000001033 ether group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
125000000101 thioether group Chemical group 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
230000000087 stabilizing effect Effects 0.000 claims 2
229920005613 synthetic organic polymer Polymers 0.000 claims 1
239000003381 stabilizer Substances 0.000 abstract description 17
239000011368 organic material Substances 0.000 abstract description 9
-1 n-octyl Chemical group 0.000 description 78
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
239000007787 solid Substances 0.000 description 40
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
238000002844 melting Methods 0.000 description 36
230000008018 melting Effects 0.000 description 36
239000000463 material Substances 0.000 description 35
238000010992 reflux Methods 0.000 description 33
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
238000000921 elemental analysis Methods 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
150000002431 hydrogen Chemical group 0.000 description 21
235000019441 ethanol Nutrition 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000007983 Tris buffer Substances 0.000 description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 13
150000002989 phenols Chemical class 0.000 description 13
239000003208 petroleum Substances 0.000 description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000011734 sodium Substances 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
239000002904 solvent Substances 0.000 description 11
FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000004743 Polypropylene Substances 0.000 description 9
238000009835 boiling Methods 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
229920001155 polypropylene Polymers 0.000 description 8
239000000047 product Substances 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000000654 additive Substances 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
239000000284 extract Substances 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
238000003756 stirring Methods 0.000 description 6
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
239000003963 antioxidant agent Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
238000004821 distillation Methods 0.000 description 5
238000000034 method Methods 0.000 description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
230000000996 additive effect Effects 0.000 description 4
238000004949 mass spectrometry Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
230000005855 radiation Effects 0.000 description 4
ZPHLQJFYCYTLLX-UHFFFAOYSA-N 2-chloro-4,6-bis(methylsulfanyl)-1,3,5-triazine Chemical compound CSC1=NC(Cl)=NC(SC)=N1 ZPHLQJFYCYTLLX-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000005864 Sulphur Chemical group 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001412 amines Chemical group 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000011888 foil Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000004611 light stabiliser Substances 0.000 description 3
150000002815 nickel Chemical class 0.000 description 3
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
LXVKMWBQSJTIPX-UHFFFAOYSA-N 2,6-dichloro-n,n-dimethylpyrimidin-4-amine Chemical compound CN(C)C1=CC(Cl)=NC(Cl)=N1 LXVKMWBQSJTIPX-UHFFFAOYSA-N 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
YLVXPXINUWURSG-UHFFFAOYSA-N [hydroxy(phenyl)methyl]phosphonic acid Chemical compound OP(=O)(O)C(O)C1=CC=CC=C1 YLVXPXINUWURSG-UHFFFAOYSA-N 0.000 description 2
239000006096 absorbing agent Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
238000000265 homogenisation Methods 0.000 description 2
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
238000004898 kneading Methods 0.000 description 2
239000003446 ligand Substances 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000002667 nucleating agent Substances 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
229920000915 polyvinyl chloride Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
239000008096 xylene Substances 0.000 description 2
HQEPZWYPQQKFLU-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(O)=C1C(=O)C1=CC=CC=C1 HQEPZWYPQQKFLU-UHFFFAOYSA-N 0.000 description 1
LSFYCRUFNRBZNC-UHFFFAOYSA-N (2-hydroxyphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1O LSFYCRUFNRBZNC-UHFFFAOYSA-N 0.000 description 1
HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
ATLWFAZCZPSXII-UHFFFAOYSA-N (2-octylphenyl) 2-hydroxybenzoate Chemical compound CCCCCCCCC1=CC=CC=C1OC(=O)C1=CC=CC=C1O ATLWFAZCZPSXII-UHFFFAOYSA-N 0.000 description 1
GOZHNJTXLALKRL-UHFFFAOYSA-N (5-benzoyl-2,4-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 GOZHNJTXLALKRL-UHFFFAOYSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical class C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VLTHAKKFNPUWSB-UHFFFAOYSA-N 1-benzyl-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1CC1=CC=CC=C1 VLTHAKKFNPUWSB-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
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
LKIVHUKSDDLFMW-UHFFFAOYSA-N 1-phenylpentylphosphonic acid Chemical compound CCCCC(P(O)(O)=O)C1=CC=CC=C1 LKIVHUKSDDLFMW-UHFFFAOYSA-N 0.000 description 1
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
WIXBXJIVPHLUHV-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-prop-2-enylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1CC=C WIXBXJIVPHLUHV-UHFFFAOYSA-N 0.000 description 1
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LLMGRFACCRADSB-UHFFFAOYSA-N octadecyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)acetate octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CC(=O)OCCCCCCCCCCCCCCCCCC.C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CCC(=O)OCCCCCCCCCCCCCCCCCC LLMGRFACCRADSB-UHFFFAOYSA-N 0.000 description 1
RNVAPPWJCZTWQL-UHFFFAOYSA-N octadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RNVAPPWJCZTWQL-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000003973 paint Substances 0.000 description 1
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
229960000969 phenyl salicylate Drugs 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
238000001782 photodegradation Methods 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229920006122 polyamide resin Polymers 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000005033 polyvinylidene chloride Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical class [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000009987 spinning Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)

CA264,259A 1972-04-21 1976-10-27 Derives de la piperidine Expired CA1041509A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB1855872A GB1393551A (en)	1972-04-21	1972-04-21	Piperidine derivatives
GB546973		1973-02-03
CA168,344A CA1003417A (en)	1972-04-21	1973-04-10	Piperidine derivatives

Publications (1)

Publication Number	Publication Date
CA1041509A true CA1041509A (fr)	1978-10-31

Family

ID=27162701

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA264,259A Expired CA1041509A (fr)	1972-04-21	1976-10-27	Derives de la piperidine

Country Status (1)

Country	Link
CA (1)	CA1041509A (fr)

1976
- 1976-10-27 CA CA264,259A patent/CA1041509A/fr not_active Expired

Publication	Publication Date	Title
US3925376A (en)	1975-12-09	Piperidine derivatives
US4028334A (en)	1977-06-07	Piperidine derivatives
US4191683A (en)	1980-03-04	Derivatives of 4-aminopiperidine as stabilizers for polymers
US4038280A (en)	1977-07-26	Hydroxyaryl-tetramethyl-piperidines
USRE31342E (en)	1983-08-09	Piperidyl carboxylates
US5668198A (en)	1997-09-16	Polymer stabilizers containing both hindered amine and hydroxylamine moieties
CA1140926A (fr)	1983-02-08	Stabilisateurs a base de triazine
US4480092A (en)	1984-10-30	Alkylated polyalkylenepolyamines, substituted oxo-piperazinyl-triazines
US4075165A (en)	1978-02-21	Stabilization of polymers by penta- or hexa-substituted 4-piperidinol derivatives
US4141883A (en)	1979-02-27	Stabilization of synthetic polymers by penta-or-hexa-substituted 4-piperidinol derivatives
US4046737A (en)	1977-09-06	Piperidine derivatives
US4049647A (en)	1977-09-20	Bis piperidyl carboxylates
US4014887A (en)	1977-03-29	Substituted piperidin-4-ols
US3850877A (en)	1974-11-26	Piperidine stabilizers for polymers
US4547538A (en)	1985-10-15	Alkylated polyalkylenepolyamines, substituted oxo-piperazinyl-triazines and UV light stabilized compositions
US3939168A (en)	1976-02-17	4-Piperidine acetamides
IL44629A (en)	1977-02-28	Stabilization of synthetic polymers by means of certain 1-substituted piperidine derivatives
US3929804A (en)	1975-12-30	4-Piperidine acetamide compounds
US3956310A (en)	1976-05-11	N-carbamoyl imidazolidinones and imidazolidinethiones
US3960809A (en)	1976-06-01	Compositions stabilized with hindered piperidine carboxylic acids
US3959291A (en)	1976-05-25	Piperidine derivatives
US3954779A (en)	1976-05-04	4-(4'-Hydroxycyclohexyl)-2,2,6,6-tetramethyl piperidines
US3962255A (en)	1976-06-08	1,4-diazaepine-5-ones
US3998784A (en)	1976-12-21	Compositions stabilized with piperidine derivatives
CA1041509A (fr)	1978-10-31	Derives de la piperidine