DE2456864A1 - Stabilisatoren fuer synthetische polymere - Google Patents
Stabilisatoren fuer synthetische polymereInfo
- Publication number
- DE2456864A1 DE2456864A1 DE19742456864 DE2456864A DE2456864A1 DE 2456864 A1 DE2456864 A1 DE 2456864A1 DE 19742456864 DE19742456864 DE 19742456864 DE 2456864 A DE2456864 A DE 2456864A DE 2456864 A1 DE2456864 A1 DE 2456864A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- formula
- hydrogen
- tert
- methyl
- 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.)
- Granted
Links
- 239000003381 stabilizer Substances 0.000 title claims description 22
- 229920001059 synthetic polymer Polymers 0.000 title description 4
- -1 tert-amyl group Chemical group 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000006289 hydroxybenzyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 229920000620 organic polymer Polymers 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical class CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 23
- 229920000642 polymer Polymers 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000004743 Polypropylene Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229920001155 polypropylene Polymers 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RULPVRPMLUDXPR-UHFFFAOYSA-N 2-[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]propanedioic acid Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC(C(O)=O)C(O)=O RULPVRPMLUDXPR-UHFFFAOYSA-N 0.000 description 3
- GHQOUFDDPQNBDR-UHFFFAOYSA-N 2-benzyl-2-hydroxypropanedioic acid Chemical class OC(=O)C(O)(C(O)=O)CC1=CC=CC=C1 GHQOUFDDPQNBDR-UHFFFAOYSA-N 0.000 description 3
- ABBAQSIKFAPOHH-UHFFFAOYSA-N 2-butyl-2-[(4-hydroxyphenyl)methyl]propanedioic acid Chemical compound CCCCC(C(O)=O)(C(O)=O)CC1=CC=C(O)C=C1 ABBAQSIKFAPOHH-UHFFFAOYSA-N 0.000 description 3
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- JOBALMNTXJSMJJ-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidin-4-amine Chemical class CC1C(N)CCN(C)C1(C)C JOBALMNTXJSMJJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 2
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- CXPJAKCERKFUME-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) propanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 CXPJAKCERKFUME-UHFFFAOYSA-N 0.000 description 2
- UPVKSNXKHZOFBC-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) 2,2-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]propanedioate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(C(=O)OC2CC(C)(C)NC(C)(C)C2)C(=O)OC2CC(C)(C)NC(C)(C)C2)=C1 UPVKSNXKHZOFBC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- CGXOAAMIQPDTPE-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CN1C(C)(C)CC(N)CC1(C)C CGXOAAMIQPDTPE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical class CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
- CKFBEAMXCODQHI-UHFFFAOYSA-N C(CCC)OC(CSCC1=CC=C(C=C1)O)=O Chemical compound C(CCC)OC(CSCC1=CC=C(C=C1)O)=O CKFBEAMXCODQHI-UHFFFAOYSA-N 0.000 description 1
- HWTGONITCTVHSC-UHFFFAOYSA-N CC(C)(C)C1(C=C(C=CC1O)CN(C)C)C(C)(C)C Chemical compound CC(C)(C)C1(C=C(C=CC1O)CN(C)C)C(C)(C)C HWTGONITCTVHSC-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 101100272588 Escherichia coli (strain K12) bisC gene Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 101100099970 Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd) torZ gene Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000095 alkaline earth hydride Inorganic materials 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- HWUHPAFORPMXLH-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) 2,2-bis[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]propanedioate Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC1=C(C)C=C(C(C)(C)C)C(O)=C1C HWUHPAFORPMXLH-UHFFFAOYSA-N 0.000 description 1
- LIRQACVOMSIKKA-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) 2-[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]propanedioate Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(=O)OC1CC(C)(C)NC(C)(C)C1 LIRQACVOMSIKKA-UHFFFAOYSA-N 0.000 description 1
- DGBLGWVHPYOSAI-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) propanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(=O)OC1CC(C)(C)NC(C)(C)C1 DGBLGWVHPYOSAI-UHFFFAOYSA-N 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- HSMPDPBYAYSOBC-UHFFFAOYSA-N khellin Chemical compound O1C(C)=CC(=O)C2=C1C(OC)=C1OC=CC1=C2OC HSMPDPBYAYSOBC-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical class NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical class NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- YTXCAJNHPVBVDJ-UHFFFAOYSA-N octadecyl propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CC YTXCAJNHPVBVDJ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 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
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 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
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1727173A CH589056A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-12-10 | 1973-12-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2456864A1 true DE2456864A1 (de) | 1975-06-12 |
| DE2456864C2 DE2456864C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-03-09 |
Family
ID=4424096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742456864 Granted DE2456864A1 (de) | 1973-12-10 | 1974-12-02 | Stabilisatoren fuer synthetische polymere |
Country Status (19)
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2647452A1 (de) | 1975-11-07 | 1977-05-18 | Ciba Geigy Ag | Neue hydroxybenzylmalonsaeure-derivate |
| DE2705219A1 (de) * | 1976-02-12 | 1977-08-18 | Mobay Chemical Corp | Stabilisierte polycarbonatformmassen |
| DE2718458A1 (de) * | 1976-05-04 | 1977-11-24 | Ciba Geigy Ag | Neue stabilisatoren |
| DE2755340A1 (de) * | 1976-12-23 | 1978-06-29 | Ciba Geigy Ag | Neue polyalkylpiperidinderivate |
| EP0002260A3 (en) * | 1977-12-02 | 1979-06-27 | Ciba-Geigy Ag | Malonic acid derivatives of sterically hindered piperidines, process for their preparation and stabilised organic matter |
| DE2913853A1 (de) * | 1979-04-06 | 1980-10-23 | Roehm Gmbh | Verfahren zum polymerisieren von methylmethacrylat |
| EP0778298A2 (de) | 1995-12-07 | 1997-06-11 | Bayer Ag | Festkörperreiche Bindemittelkombination |
| EP1101780A2 (de) | 1999-11-17 | 2001-05-23 | Bayer Ag | Neue, festkörperrreiche Bindemittelkombinationen und deren Verwendung |
| EP2112198A1 (en) | 2008-04-24 | 2009-10-28 | 3V SIGMA S.p.A | Mixtures of sterically hindered amines for the stabilisation of polymers |
| EP2112141A1 (en) | 2008-04-23 | 2009-10-28 | 3V SIGMA S.p.A | Oligomeric sterically hindered amines and their use as polymer stabilizers |
| EP2366732A2 (en) | 2010-03-15 | 2011-09-21 | 3V SIGMA S.p.A | Mixtures of sterically hindered amines for polymer stabilisation |
| US8063144B2 (en) | 2004-11-25 | 2011-11-22 | Bayer Materialscience Ag | Polyisocyanate mixtures, a process for their preparation and their use in coating compositions |
| WO2012153260A1 (en) | 2011-05-10 | 2012-11-15 | 3V Sigma S.P.A. | Mixture of sterically hindered amines for polymer stabilization |
| EP3424977A1 (en) | 2017-06-30 | 2019-01-09 | 3V SIGMA S.p.A | Hindered polymeric amines |
| EP3428156A1 (en) | 2017-07-11 | 2019-01-16 | 3V SIGMA S.p.A | Hindered amines |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4110305A (en) * | 1971-11-30 | 1978-08-29 | Ciba-Geigy Corporation | Polymers stabilized by esters of piperidinols |
| US4052361A (en) * | 1974-12-30 | 1977-10-04 | American Cyanamid Company | N-(2,2-dimethyl-6,6-di(lower alkyl)-4-piperidinyl)-amides of hindered 3,5-dialkyl-4-hydroxybenzoic acids and use as light stabilizers in polyolefins |
| GB1496844A (en) * | 1975-05-28 | 1978-01-05 | Ciba Geigy Ag | Stabilization of polymers |
| US4202816A (en) * | 1975-06-19 | 1980-05-13 | Ciba-Geigy Corporation | Novel light stabilizers |
| CH601232A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1975-12-08 | 1978-06-30 | Ciba Geigy Ag | |
| DE2656769A1 (de) * | 1975-12-29 | 1977-07-14 | Ciba Geigy Ag | Neue phenol-stabilisatoren |
| US4197236A (en) * | 1976-04-28 | 1980-04-08 | Ciba-Geigy Corporation | Piperidine stabilizers |
| DE2717087A1 (de) * | 1976-04-28 | 1977-11-10 | Ciba Geigy Ag | Neue stabilisatoren |
| JPS537748A (en) * | 1976-07-12 | 1978-01-24 | Toray Ind Inc | Synthetic resin composition having improved light resistance and gas-stain resistance |
| JPS53144579A (en) * | 1977-05-18 | 1978-12-15 | Sankyo Co Ltd | 4-aminopolyalkylpiperidine derivatives |
| JPS5429400A (en) * | 1977-08-08 | 1979-03-05 | Sankyo Co Ltd | Polymer comprising polyalkylpiperidine and its use as stabilizers |
| US4164480A (en) * | 1978-01-09 | 1979-08-14 | Eastman Kodak Company | Polychromophoric ultraviolet stabilizers and their use in organic compositions |
| US4185003A (en) * | 1978-02-16 | 1980-01-22 | E. I. Du Pont De Nemours And Company | Stabilized copolyetheresters |
| DE2962873D1 (en) * | 1978-04-14 | 1982-07-08 | Ciba Geigy Ag | Aminodibenzoxaphosphorines, process for their preparation and their use as stabilisators |
| DE2960925D1 (en) * | 1978-05-18 | 1981-12-17 | Ciba Geigy Ag | Dioxaphosphepines, their preparation and use as stabilisers for organic materials |
| US4279720A (en) * | 1978-07-13 | 1981-07-21 | Ciba-Geigy Corporation | Photocurable composition |
| IT1110826B (it) * | 1979-02-01 | 1986-01-06 | Montedison Spa | N-alchil-piperidin derivati dell'acido idrossi-benzil malonico e loro impiego come stabilizzanti per polimeri |
| US4322527A (en) * | 1979-05-15 | 1982-03-30 | Ciba-Geigy Corporation | 6-Amino-dibenz[d,g][1,3,2]dioxaphosphocines |
| US4377651A (en) * | 1979-10-05 | 1983-03-22 | Phillips Petroleum Company | Polyolefin stabilization |
| IT1193839B (it) * | 1979-11-06 | 1988-08-24 | Montedison Spa | Poliesteri di n,n-di-alcanol-ammine con acidi di-(idrossi-alchilbenzil) malonici e loro impiego come stabilizzanti per polimeri |
| JPS56501881A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1980-01-14 | 1981-12-24 | ||
| US4402983A (en) * | 1980-09-19 | 1983-09-06 | E. I. Du Pont De Nemours & Co. | Powder coating composition for automotive topcoat |
| EP0112802B1 (de) * | 1982-12-16 | 1988-01-07 | Ciba-Geigy Ag | Farbphotographisches Aufzeichnungsmaterial |
| US4487870A (en) * | 1982-12-27 | 1984-12-11 | Exxon Research & Engineering Co. | UV Stabilizer system and UV stabilized polyolefins |
| US4751272A (en) * | 1986-05-01 | 1988-06-14 | Toray Industries, Inc. | Process for producing oxymethylene copolymer and resinous composition |
| US4874391A (en) * | 1986-07-29 | 1989-10-17 | Ciba-Geigy Corporation | Process for photochemical stabilization of polyamide fiber material and mixtures thereof with other fibers: water-soluble copper complex dye and light-stabilizer |
| ATE102666T1 (de) * | 1988-06-14 | 1994-03-15 | Ciba Geigy Ag | Verfahren zum fotochemischen stabilisieren von ungefaerbten und gefaerbten polypropylenfasern. |
| US4892784A (en) * | 1988-07-27 | 1990-01-09 | Kimberly-Clark Corporation | Surface treatment for inhibiting thermal oxidation of polypropylene fabrics |
| US5030243A (en) * | 1989-01-05 | 1991-07-09 | Ciba-Geigy Corporation | Process for the photochemical stabilization of undyed and dyeable artificial leather with a sterically hindered amine |
| US5932640A (en) | 1989-01-21 | 1999-08-03 | Clariant Finance (Bvi) Limited | Dyeability or mass coloration of synthetic polyamide |
| US5015683A (en) * | 1989-03-21 | 1991-05-14 | Ciba-Geigy Corporation | Bis(1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-amine derivatives and stabilized compositions |
| EP0409771A3 (en) * | 1989-06-27 | 1991-06-12 | Ciba-Geigy Ag | Process of photochemical and thermal stabilization of polyamide fibres, dyeable by acid and basic dyes, and of their mixtures amongst themselves and with other fibres |
| IT1247974B (it) * | 1991-06-04 | 1995-01-05 | Sigma Prod Chim | Derivati di piperidina, loro preparazione e uso |
| DE19707733B4 (de) | 1996-02-29 | 2017-07-20 | Synthopol Chemie Dr.Rer.Pol. Koch Gmbh & Co Kg | Neue Polyesterpolyole und ihre Verwendung als Polyolkomponente in Zweikomponenten-Polyurethanlacken |
| TWI224995B (en) * | 1998-03-19 | 2004-12-11 | Ciba Sc Holding Ag | Stabilization of wood substrates |
| DE10322620A1 (de) * | 2003-05-20 | 2004-12-16 | Bayer Materialscience Ag | Festkörperreiche Bindemittelkombinationen für kratzfeste Decklacke |
| US20050137322A1 (en) * | 2003-12-17 | 2005-06-23 | Roesler Richard R. | Silane modified two-component polyurethane coating |
| KR20070121747A (ko) * | 2005-04-18 | 2007-12-27 | 코니카 미놀타 옵토 인코포레이티드 | 셀룰로오스에스테르 필름 및 그의 제조 방법, 광학 필름,편광판 및 액정 표시 장치 |
| DK1981944T3 (en) * | 2005-11-10 | 2016-04-18 | Ppg Bv | EPOXY-Based Coatings |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2258752A1 (de) * | 1971-11-30 | 1973-06-07 | Ciba Geigy Ag | Neue piperidin-derivate |
| DE2257997A1 (de) * | 1971-11-30 | 1973-06-14 | Ciba Geigy Ag | Piperidinolester |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3721704A (en) * | 1967-02-17 | 1973-03-20 | Geigy Chem Corp | Esters of (dialkyl-4-hydroxy-phenyl)malonic acid and related compounds |
| US3640928A (en) * | 1968-06-12 | 1972-02-08 | Sankyo Co | Stabilization of synthetic polymers |
| NL154241C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-01-29 | 1900-01-01 | ||
| US3992390A (en) * | 1971-11-30 | 1976-11-16 | Brian Holt | Esters of piperidinols |
-
1973
- 1973-12-10 CH CH1727173A patent/CH589056A5/xx not_active IP Right Cessation
-
1974
- 1974-01-01 AR AR256818A patent/AR204430A1/es active
- 1974-10-31 SE SE7413720A patent/SE7413720L/xx unknown
- 1974-11-21 US US05/525,810 patent/US3993655A/en not_active Expired - Lifetime
- 1974-11-30 JP JP49138810A patent/JPS5817500B2/ja not_active Expired
- 1974-12-02 DE DE19742456864 patent/DE2456864A1/de active Granted
- 1974-12-06 GB GB5278574A patent/GB1442100A/en not_active Expired
- 1974-12-06 CA CA215,346A patent/CA1032946A/en not_active Expired
- 1974-12-09 BR BR10269/74A patent/BR7410269A/pt unknown
- 1974-12-09 AT AT982174A patent/AT331522B/de not_active IP Right Cessation
- 1974-12-09 ZA ZA00747815A patent/ZA747815B/xx unknown
- 1974-12-09 BE BE151298A patent/BE823114A/xx unknown
- 1974-12-09 IL IL46203A patent/IL46203A0/xx unknown
- 1974-12-09 ES ES432713A patent/ES432713A1/es not_active Expired
- 1974-12-09 FR FR7440235A patent/FR2253742B1/fr not_active Expired
- 1974-12-09 AU AU76194/74A patent/AU7619474A/en not_active Expired
- 1974-12-09 SU SU742083824A patent/SU708995A3/ru active
- 1974-12-09 IT IT30297/74A patent/IT1026868B/it active
- 1974-12-10 NL NL7416065A patent/NL7416065A/xx not_active Application Discontinuation
-
1978
- 1978-06-13 US US05/915,346 patent/US4221701A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2258752A1 (de) * | 1971-11-30 | 1973-06-07 | Ciba Geigy Ag | Neue piperidin-derivate |
| DE2257997A1 (de) * | 1971-11-30 | 1973-06-14 | Ciba Geigy Ag | Piperidinolester |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2647452A1 (de) | 1975-11-07 | 1977-05-18 | Ciba Geigy Ag | Neue hydroxybenzylmalonsaeure-derivate |
| DE2661090C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1975-11-07 | 1990-02-08 | Ciba-Geigy Ag, Basel, Ch | |
| DE2705219A1 (de) * | 1976-02-12 | 1977-08-18 | Mobay Chemical Corp | Stabilisierte polycarbonatformmassen |
| DE2718458A1 (de) * | 1976-05-04 | 1977-11-24 | Ciba Geigy Ag | Neue stabilisatoren |
| DE2755340A1 (de) * | 1976-12-23 | 1978-06-29 | Ciba Geigy Ag | Neue polyalkylpiperidinderivate |
| EP0002260A3 (en) * | 1977-12-02 | 1979-06-27 | Ciba-Geigy Ag | Malonic acid derivatives of sterically hindered piperidines, process for their preparation and stabilised organic matter |
| DE2913853A1 (de) * | 1979-04-06 | 1980-10-23 | Roehm Gmbh | Verfahren zum polymerisieren von methylmethacrylat |
| EP0778298A2 (de) | 1995-12-07 | 1997-06-11 | Bayer Ag | Festkörperreiche Bindemittelkombination |
| EP1101780A2 (de) | 1999-11-17 | 2001-05-23 | Bayer Ag | Neue, festkörperrreiche Bindemittelkombinationen und deren Verwendung |
| US8063144B2 (en) | 2004-11-25 | 2011-11-22 | Bayer Materialscience Ag | Polyisocyanate mixtures, a process for their preparation and their use in coating compositions |
| EP2112141A1 (en) | 2008-04-23 | 2009-10-28 | 3V SIGMA S.p.A | Oligomeric sterically hindered amines and their use as polymer stabilizers |
| US8003718B2 (en) | 2008-04-23 | 2011-08-23 | 3V Sigma S.P.A. | Oligomeric sterically hindered amines and their use as polymer stabilisers |
| EP2112198A1 (en) | 2008-04-24 | 2009-10-28 | 3V SIGMA S.p.A | Mixtures of sterically hindered amines for the stabilisation of polymers |
| US7713444B2 (en) | 2008-04-24 | 2010-05-11 | 3V Sigma S.P.A. | Mixtures of sterically hindered amines for the stabilisation of polymers |
| EP2366732A2 (en) | 2010-03-15 | 2011-09-21 | 3V SIGMA S.p.A | Mixtures of sterically hindered amines for polymer stabilisation |
| WO2012153260A1 (en) | 2011-05-10 | 2012-11-15 | 3V Sigma S.P.A. | Mixture of sterically hindered amines for polymer stabilization |
| EP3424977A1 (en) | 2017-06-30 | 2019-01-09 | 3V SIGMA S.p.A | Hindered polymeric amines |
| EP3428156A1 (en) | 2017-07-11 | 2019-01-16 | 3V SIGMA S.p.A | Hindered amines |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7413720L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-11 |
| BE823114A (fr) | 1975-06-09 |
| JPS50116529A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-11 |
| FR2253742A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-04 |
| ATA982174A (de) | 1975-11-15 |
| SU708995A3 (ru) | 1980-01-05 |
| DE2456864C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-03-09 |
| ES432713A1 (es) | 1976-12-16 |
| AU7619474A (en) | 1976-06-10 |
| US3993655A (en) | 1976-11-23 |
| GB1442100A (en) | 1976-07-07 |
| BR7410269A (pt) | 1976-06-29 |
| CA1032946A (en) | 1978-06-13 |
| IL46203A0 (en) | 1975-03-13 |
| IT1026868B (it) | 1978-10-20 |
| ZA747815B (en) | 1975-12-31 |
| AR204430A1 (es) | 1976-02-06 |
| JPS5817500B2 (ja) | 1983-04-07 |
| US4221701A (en) | 1980-09-09 |
| FR2253742B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-22 |
| NL7416065A (nl) | 1975-06-12 |
| AT331522B (de) | 1976-08-25 |
| CH589056A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2456864A1 (de) | Stabilisatoren fuer synthetische polymere | |
| DE2760429C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2319816C2 (de) | Piperidin-Derivate, Verfahren zu deren Herstellung und deren Verwendung | |
| EP0024338B1 (de) | Neue Triazinderivate, ihre Herstellung und ihre Verwendung als Stabilisatoren für synthetische Polymere | |
| DE2264582C3 (de) | Synthetische Polymermasse, die gegen licht- und Wärmeeinwirkung stabilisiert ist | |
| DE2352658C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2203533A1 (de) | 4-piperidonketalderivate, ihre herstellung und ihre verwendung als stabilisatoren | |
| DE2654058A1 (de) | Hydroxybenzylmalonsaeurederivate | |
| DE2851448A1 (de) | Stabilisierung von polymeren | |
| EP0013443B1 (de) | 2,2,6,6-Tetramethylpiperidin-Derivate, Verfahren zu ihrer Herstellung und mit ihrer Hilfe stabilisierte synthetische Polymere | |
| DE2128757A1 (de) | Piperidinderivate und deren Verwendung als Stabilisatoren | |
| DE2233122C3 (de) | 1,3,8-Triaza-7,7,9,9 -tetramethyl-spiro [4.5] decan-2,4-dione | |
| DE2219695A1 (de) | Bicyclische Phosphorverbindungen | |
| DE2621841A1 (de) | Lichtschutzmittel fuer polymere | |
| DE2745058A1 (de) | Bis-polyalkylpiperidine | |
| DE2421309A1 (de) | Veresterte isopropanolamine, verfahren zu ihrer herstellung und verwendung derselben | |
| DE2656999A1 (de) | Neue phosphite | |
| EP0000487A1 (de) | Enolgruppen enthaltende Verbindungen, deren Metallchelate, deren Herstellung und Verwendung als Lichtschutzmittel insbesondere in hochmolekularen Verbindungen. | |
| DE2043748A1 (de) | Piperidin spiro oxirandenvate, Verfahren zu ihrer Herstellung und ihre Anwendung als Stabilisatoren | |
| EP0300161B1 (de) | Stabilisatorsystem | |
| DE2203447A1 (de) | Diazepinon als Stabilisator | |
| DE2819882A1 (de) | Mit polyalkylthiobenzolen stabilisierte massen | |
| CH597185A5 (en) | Stabilising synthetic polymers, pref polyolefines | |
| DE2656748C2 (de) | Phosphitgemische, Verfahren zu ihrer Herstellung und ihre Verwendung zum Stabilisieren organischer Materialien | |
| DE2805821A1 (de) | Neue metallsalze von hydroxybenzoesaeuren, die durch polyalkylpiperidin-liganden komplexiert sind |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |