NL1011394C2 - Bereiding van sterisch gehinderde amine-ethers. - Google Patents

Bereiding van sterisch gehinderde amine-ethers. Download PDF

Info

Publication number: NL1011394C2
Authority: NL; Netherlands
Prior art keywords: alkyl; formula; group; substituted; independently
Prior art date: 1998-02-25

Application number

NL1011394A

Other languages

English (en)

Dutch (nl)

Other versions

NL1011394A1 (nl

Inventor

Alessandro Zedda

Massimiliano Sala

Gianluca Ferri

Original Assignee

Ciba Sc Holding 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.)

1998-02-25

Filing date

1999-02-25

Publication date

1999-10-26

1998-02-25 Priority claimed from IT98MI000366A external-priority patent/ITMI980366A1/it

1999-02-25 Application filed by Ciba Sc Holding Ag filed Critical Ciba Sc Holding Ag

1999-08-26 Publication of NL1011394A1 publication Critical patent/NL1011394A1/xx

1999-10-26 Application granted granted Critical

1999-10-26 Publication of NL1011394C2 publication Critical patent/NL1011394C2/nl

Links

-1 amine ethers Chemical class 0.000 title claims description 224
238000002360 preparation method Methods 0.000 title claims description 19
150000001875 compounds Chemical class 0.000 claims description 148
229910052739 hydrogen Inorganic materials 0.000 claims description 104
239000000203 mixture Substances 0.000 claims description 99
239000001257 hydrogen Substances 0.000 claims description 81
125000000217 alkyl group Chemical group 0.000 claims description 76
229910052799 carbon Inorganic materials 0.000 claims description 66
125000003118 aryl group Chemical group 0.000 claims description 57
125000004432 carbon atom Chemical group C* 0.000 claims description 54
125000000753 cycloalkyl group Chemical group 0.000 claims description 52
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
229910052736 halogen Inorganic materials 0.000 claims description 46
150000002367 halogens Chemical group 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
125000001931 aliphatic group Chemical group 0.000 claims description 39
238000000034 method Methods 0.000 claims description 38
229910052757 nitrogen Inorganic materials 0.000 claims description 37
229910052760 oxygen Inorganic materials 0.000 claims description 35
125000002947 alkylene group Chemical group 0.000 claims description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
239000001301 oxygen Substances 0.000 claims description 34
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 34
238000000576 coating method Methods 0.000 claims description 33
150000002431 hydrogen Chemical class 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 30
239000003381 stabilizer Substances 0.000 claims description 30
125000003342 alkenyl group Chemical group 0.000 claims description 26
229910052751 metal Inorganic materials 0.000 claims description 23
239000002184 metal Substances 0.000 claims description 22
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
229910052698 phosphorus Inorganic materials 0.000 claims description 20
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 19
239000011230 binding agent Substances 0.000 claims description 19
239000011574 phosphorus Chemical group 0.000 claims description 19
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 18
125000006575 electron-withdrawing group Chemical group 0.000 claims description 17
125000005842 heteroatom Chemical group 0.000 claims description 16
229930195733 hydrocarbon Natural products 0.000 claims description 16
125000005647 linker group Chemical group 0.000 claims description 16
230000008569 process Effects 0.000 claims description 16
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
239000003795 chemical substances by application Substances 0.000 claims description 15
150000002430 hydrocarbons Chemical class 0.000 claims description 15
125000003884 phenylalkyl group Chemical group 0.000 claims description 15
125000002252 acyl group Chemical group 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000004122 cyclic group Chemical group 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
239000004215 Carbon black (E152) Substances 0.000 claims description 13
239000011248 coating agent Substances 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
229920000620 organic polymer Polymers 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
239000000463 material Substances 0.000 claims description 11
230000000087 stabilizing effect Effects 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
239000011593 sulfur Chemical group 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 9
229920001169 thermoplastic Polymers 0.000 claims description 9
125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 8
230000015556 catabolic process Effects 0.000 claims description 8
238000006731 degradation reaction Methods 0.000 claims description 8
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
125000000732 arylene group Chemical group 0.000 claims description 7
239000003063 flame retardant Substances 0.000 claims description 7
238000007254 oxidation reaction Methods 0.000 claims description 7
230000001590 oxidative effect Effects 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
229910052710 silicon Inorganic materials 0.000 claims description 7
239000010703 silicon Chemical group 0.000 claims description 7
239000004416 thermosoftening plastic Substances 0.000 claims description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 6
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
239000004611 light stabiliser Substances 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
239000011368 organic material Substances 0.000 claims description 6
239000000049 pigment Substances 0.000 claims description 6
OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
125000006839 xylylene group Chemical group 0.000 claims description 6
239000006096 absorbing agent Substances 0.000 claims description 5
238000005984 hydrogenation reaction Methods 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 5
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
125000002993 cycloalkylene group Chemical group 0.000 claims description 4
WMNPPTFIWBUUQT-NAWIUCTOSA-N G12 Chemical compound C1=NC(C(NC(N)=N2)=O)=C2N1[C@@H]([C@@H]1O)O[C@H](COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2CO)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)[C@H]1OP(O)(=O)OC[C@H]([C@@H](O)[C@H]1O)O[C@H]1N1C(N=C(NC2=O)N)=C2N=C1 WMNPPTFIWBUUQT-NAWIUCTOSA-N 0.000 claims description 3
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
125000004450 alkenylene group Chemical group 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
230000026030 halogenation Effects 0.000 claims description 3
238000005658 halogenation reaction Methods 0.000 claims description 3
150000002978 peroxides Chemical class 0.000 claims description 3
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
239000004014 plasticizer Substances 0.000 claims description 3
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 3
229910052720 vanadium Inorganic materials 0.000 claims description 3
150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 3
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 claims description 2
YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 claims description 2
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims description 2
239000012965 benzophenone Substances 0.000 claims description 2
150000008366 benzophenones Chemical class 0.000 claims description 2
239000000975 dye Substances 0.000 claims description 2
150000002823 nitrates Chemical class 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 6
125000001589 carboacyl group Chemical group 0.000 claims 2
150000001735 carboxylic acids Chemical class 0.000 claims 2
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 1
101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 claims 1
125000004423 acyloxy group Chemical group 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
230000009974 thixotropic effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 55
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
229920001577 copolymer Polymers 0.000 description 40
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
239000000047 product Substances 0.000 description 40
229920000642 polymer Polymers 0.000 description 37
150000003254 radicals Chemical class 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000003054 catalyst Substances 0.000 description 27
150000001721 carbon Chemical group 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 22
150000001412 amines Chemical class 0.000 description 22
229920005989 resin Polymers 0.000 description 22
239000011347 resin Substances 0.000 description 22
238000003756 stirring Methods 0.000 description 22
239000003973 paint Substances 0.000 description 21
229910000027 potassium carbonate Inorganic materials 0.000 description 20
239000008199 coating composition Substances 0.000 description 19
150000002148 esters Chemical group 0.000 description 19
229920001684 low density polyethylene Polymers 0.000 description 19
239000004702 low-density polyethylene Substances 0.000 description 19
235000011181 potassium carbonates Nutrition 0.000 description 18
239000007787 solid Substances 0.000 description 18
239000004743 Polypropylene Substances 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
229920001155 polypropylene Polymers 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 15
239000000843 powder Substances 0.000 description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 12
239000004952 Polyamide Substances 0.000 description 12
239000007859 condensation product Substances 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
229920002647 polyamide Polymers 0.000 description 12
229920000515 polycarbonate Polymers 0.000 description 12
239000004417 polycarbonate Substances 0.000 description 12
239000008096 xylene Substances 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
239000011572 manganese Substances 0.000 description 11
229920000728 polyester Polymers 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
239000005977 Ethylene Substances 0.000 description 10
229920000877 Melamine resin Polymers 0.000 description 10
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
239000004698 Polyethylene Substances 0.000 description 10
150000001252 acrylic acid derivatives Chemical class 0.000 description 10
229910052794 bromium Inorganic materials 0.000 description 10
238000001723 curing Methods 0.000 description 10
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 10
239000010410 layer Substances 0.000 description 10
229920000573 polyethylene Polymers 0.000 description 10
239000004814 polyurethane Substances 0.000 description 10
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
239000000654 additive Substances 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
238000001914 filtration Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
229920002857 polybutadiene Polymers 0.000 description 9
229920000647 polyepoxide Polymers 0.000 description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000005062 Polybutadiene Substances 0.000 description 8
239000004721 Polyphenylene oxide Substances 0.000 description 8
239000007983 Tris buffer Substances 0.000 description 8
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
238000001035 drying Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
229920002635 polyurethane Polymers 0.000 description 8
229910001220 stainless steel Inorganic materials 0.000 description 8
239000010935 stainless steel Substances 0.000 description 8
239000000758 substrate Substances 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
239000012964 benzotriazole Substances 0.000 description 7
229920001903 high density polyethylene Polymers 0.000 description 7
239000004700 high-density polyethylene Substances 0.000 description 7
229910052748 manganese Inorganic materials 0.000 description 7
239000000575 pesticide Substances 0.000 description 7
229920000570 polyether Polymers 0.000 description 7
238000006116 polymerization reaction Methods 0.000 description 7
229920006324 polyoxymethylene Polymers 0.000 description 7
230000006641 stabilisation Effects 0.000 description 7
238000011105 stabilization Methods 0.000 description 7
239000004925 Acrylic resin Substances 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000004594 Masterbatch (MB) Substances 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
239000003431 cross linking reagent Substances 0.000 description 6
150000001993 dienes Chemical class 0.000 description 6
229920001971 elastomer Polymers 0.000 description 6
238000005227 gel permeation chromatography Methods 0.000 description 6
239000012948 isocyanate Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 6
239000000178 monomer Substances 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
229920000058 polyacrylate Polymers 0.000 description 6
239000005056 polyisocyanate Substances 0.000 description 6
229920001228 polyisocyanate Polymers 0.000 description 6
229920000098 polyolefin Polymers 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
229920000178 Acrylic resin Polymers 0.000 description 5
239000004593 Epoxy Substances 0.000 description 5
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
229920000180 alkyd Polymers 0.000 description 5
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CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-UHFFFAOYSA-N 0.000 description 1
IMXRBCGZTVENAC-UHFFFAOYSA-N n-phenyl-n-(2,4,4-trimethylpentan-2-yl)aniline Chemical class C=1C=CC=CC=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 IMXRBCGZTVENAC-UHFFFAOYSA-N 0.000 description 1
NYLGUNUDTDWXQE-UHFFFAOYSA-N n-phenyl-n-prop-2-enylaniline Chemical compound C=1C=CC=CC=1N(CC=C)C1=CC=CC=C1 NYLGUNUDTDWXQE-UHFFFAOYSA-N 0.000 description 1
MHJCZOMOUCUAOI-UHFFFAOYSA-N n-tert-butyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(C(C)(C)C)C1=CC=CC=C1 MHJCZOMOUCUAOI-UHFFFAOYSA-N 0.000 description 1
125000005609 naphthenate group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002816 nickel compounds Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
IBGCXOFOCKCBNQ-UHFFFAOYSA-N nitro cyanate Chemical compound [O-][N+](=O)OC#N IBGCXOFOCKCBNQ-UHFFFAOYSA-N 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
239000002667 nucleating agent Substances 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
QANCZOOABLPKBN-UHFFFAOYSA-N octadecan-5-ol Chemical compound CCCCCCCCCCCCCC(O)CCCC QANCZOOABLPKBN-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
125000005474 octanoate group Chemical group 0.000 description 1
TWCBCCIODCKPGX-UHFFFAOYSA-N octyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]propanoate Chemical compound OC1=CC(OC(C)C(=O)OCCCCCCCC)=CC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 TWCBCCIODCKPGX-UHFFFAOYSA-N 0.000 description 1
XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 description 1
NTTIENRNNNJCHQ-UHFFFAOYSA-N octyl n-(3,5-ditert-butyl-4-hydroxyphenyl)carbamate Chemical compound CCCCCCCCOC(=O)NC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NTTIENRNNNJCHQ-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001312 palmitoyl 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])[H] 0.000 description 1
239000011087 paperboard Substances 0.000 description 1
229960000490 permethrin Drugs 0.000 description 1
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000002688 persistence Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
229960000969 phenyl salicylate Drugs 0.000 description 1
SYMZQKVFAWDEFD-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethyl-1-propoxypiperidin-4-yl)methanone Chemical compound C1C(C)(C)N(OCCC)C(C)(C)CC1C(=O)C1=CC=CC=C1 SYMZQKVFAWDEFD-UHFFFAOYSA-N 0.000 description 1
ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000010452 phosphate Chemical group 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 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
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
229920003055 poly(ester-imide) Polymers 0.000 description 1
229920001643 poly(ether ketone) Polymers 0.000 description 1
229920002492 poly(sulfone) Polymers 0.000 description 1
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002312 polyamide-imide Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920002480 polybenzimidazole Polymers 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920006393 polyether sulfone Polymers 0.000 description 1
229920001601 polyetherimide Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940068886 polyethylene glycol 300 Drugs 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920000069 polyphenylene sulfide Polymers 0.000 description 1
229920005606 polypropylene copolymer Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920005749 polyurethane resin 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
229920002620 polyvinyl fluoride Polymers 0.000 description 1
239000005033 polyvinylidene chloride Substances 0.000 description 1
229920002981 polyvinylidene fluoride Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
208000003383 pontocerebellar hypoplasia type 3 Diseases 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
MVCPDOUDYOUTKS-UHFFFAOYSA-N propanedithioic acid Chemical compound CCC(S)=S MVCPDOUDYOUTKS-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
230000001012 protector Effects 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
238000000518 rheometry Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
229940066675 ricinoleate Drugs 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
210000002374 sebum Anatomy 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
229940074404 sodium succinate Drugs 0.000 description 1
ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003860 storage Methods 0.000 description 1
229920000638 styrene acrylonitrile Polymers 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000003760 tallow Substances 0.000 description 1
MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 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
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000000000 tetracarboxylic acids Chemical class 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
235000019303 thiodipropionic acid Nutrition 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
125000003944 tolyl group Chemical group 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
150000003918 triazines Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
150000003628 tricarboxylic acids Chemical class 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
AOQUKZYKYIPBFR-UHFFFAOYSA-N trihydroxy-nonyl-phenyl-$l^{5}-phosphane Chemical compound CCCCCCCCCP(O)(O)(O)C1=CC=CC=C1 AOQUKZYKYIPBFR-UHFFFAOYSA-N 0.000 description 1
CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
239000002966 varnish Substances 0.000 description 1
229920001866 very low density polyethylene Polymers 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
229910052845 zircon Inorganic materials 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1
239000011590 β-tocopherol Substances 0.000 description 1
235000007680 β-tocopherol Nutrition 0.000 description 1
239000002478 γ-tocopherol Substances 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
239000002446 δ-tocopherol Substances 0.000 description 1

Classifications

- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C08K5/0066—Flame-proofing or flame-retarding additives
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Hydrogenated Pyridines (AREA)
Compositions Of Macromolecular Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NL1011394A 1998-02-25 1999-02-25 Bereiding van sterisch gehinderde amine-ethers. NL1011394C2 (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
ITMI980366		1998-02-25
IT98MI000366A ITMI980366A1 (it)	1998-02-25	1998-02-25	Preparazione di eteri amminici stericamente impediti
US10471898A	1998-06-25	1998-06-25
US10471898		1998-06-25

Publications (2)

Publication Number	Publication Date
NL1011394A1 NL1011394A1 (nl)	1999-08-26
NL1011394C2 true NL1011394C2 (nl)	1999-10-26

Family

ID=26331570

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1011394A NL1011394C2 (nl)	1998-02-25	1999-02-25	Bereiding van sterisch gehinderde amine-ethers.

Country Status (17)

Country	Link
JP (2)	JP4798815B2 (2)
KR (1)	KR100561146B1 (2)
CN (2)	CN100384826C (2)
AR (1)	AR015238A1 (2)
BE (1)	BE1014990A5 (2)
BR (1)	BR9900807B1 (2)
CA (2)	CA2262435C (2)
CZ (1)	CZ302752B6 (2)
DE (2)	DE19964603B4 (2)
ES (1)	ES2159462B1 (2)
FR (1)	FR2777004B1 (2)
GB (1)	GB2334717B (2)
ID (1)	ID23225A (2)
MY (1)	MY123467A (2)
NL (1)	NL1011394C2 (2)
RU (1)	RU2224758C2 (2)
SG (1)	SG74700A1 (2)

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1999
- 1999-02-06 SG SG1999000492A patent/SG74700A1/en unknown
- 1999-02-08 MY MYPI99000420A patent/MY123467A/en unknown
- 1999-02-17 GB GB9903463A patent/GB2334717B/en not_active Expired - Lifetime
- 1999-02-22 CZ CZ20080401A patent/CZ302752B6/cs not_active IP Right Cessation
- 1999-02-23 AR ARP990100722A patent/AR015238A1/es active IP Right Grant
- 1999-02-23 CA CA002262435A patent/CA2262435C/en not_active Expired - Lifetime
- 1999-02-23 FR FR9902218A patent/FR2777004B1/fr not_active Expired - Lifetime
- 1999-02-23 CA CA2643170A patent/CA2643170C/en not_active Expired - Lifetime
- 1999-02-24 RU RU99103614/04A patent/RU2224758C2/ru active
- 1999-02-24 KR KR1019990006156A patent/KR100561146B1/ko not_active Expired - Lifetime
- 1999-02-24 DE DE19964603A patent/DE19964603B4/de not_active Expired - Lifetime
- 1999-02-24 CN CNB2004100473618A patent/CN100384826C/zh not_active Expired - Lifetime
- 1999-02-24 CN CNB991033833A patent/CN1202085C/zh not_active Expired - Lifetime
- 1999-02-24 DE DE19907945A patent/DE19907945B4/de not_active Expired - Lifetime
- 1999-02-24 ES ES009900376A patent/ES2159462B1/es not_active Expired - Lifetime
- 1999-02-24 ID IDP990142D patent/ID23225A/id unknown
- 1999-02-25 BR BRPI9900807-6B1A patent/BR9900807B1/pt active IP Right Grant
- 1999-02-25 BE BE9900127A patent/BE1014990A5/fr not_active IP Right Cessation
- 1999-02-25 JP JP04790499A patent/JP4798815B2/ja not_active Expired - Lifetime
- 1999-02-25 NL NL1011394A patent/NL1011394C2/nl not_active IP Right Cessation
2010
- 2010-08-17 JP JP2010182352A patent/JP2011006443A/ja active Pending

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6683142B2 (en)	1998-03-09	2004-01-27	Ciba Specialty Chemicals Corporation	1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators
US6927295B2 (en)	1998-03-09	2005-08-09	Ciba Specialty Chemicals Corp.	1-alkoxy-polyalkyl-piperidine derivatives and their use as polymerization regulators

Also Published As

Publication number	Publication date
CZ302752B6 (cs)	2011-10-19
FR2777004A1 (fr)	1999-10-08
CA2262435C (en)	2009-12-22
KR19990072904A (ko)	1999-09-27
FR2777004B1 (fr)	2005-12-30
CN1235159A (zh)	1999-11-17
CA2262435A1 (en)	1999-08-25
RU2224758C2 (ru)	2004-02-27
BE1014990A5 (fr)	2004-08-03
ES2159462A1 (es)	2001-10-01
CN100384826C (zh)	2008-04-30
GB9903463D0 (en)	1999-04-07
GB2334717B (en)	2000-04-26
JP2011006443A (ja)	2011-01-13
CN1202085C (zh)	2005-05-18
CA2643170A1 (en)	1999-08-25
DE19907945A1 (de)	1999-08-26
JPH11315067A (ja)	1999-11-16
DE19964603B4 (de)	2013-02-28
AR015238A1 (es)	2001-04-18
SG74700A1 (en)	2000-08-22
BR9900807A (pt)	2000-03-28
NL1011394A1 (nl)	1999-08-26
MY123467A (en)	2006-05-31
CN1552758A (zh)	2004-12-08
KR100561146B1 (ko)	2006-03-15
ID23225A (id)	2000-03-30
JP4798815B2 (ja)	2011-10-19
BR9900807B1 (pt)	2013-06-11
DE19907945B4 (de)	2013-06-06
CA2643170C (en)	2013-04-16
GB2334717A (en)	1999-09-01
ES2159462B1 (es)	2002-05-01

Legal Events

Date	Code	Title	Description
2000-01-03	PD2B	A search report has been drawn up
2019-02-27	MK	Patent expired because of reaching the maximum lifetime of a patent	Effective date: 20190224

Publication	Publication Date	Title
US6117995A (en)	2000-09-12	Preparation of sterically hindered amine ethers
CA2262435C (en)	2009-12-22	Preparation of sterically hindered amine ethers
AU731977B2 (en)	2001-04-12	Hydroxyphenyltriazines
NL1006140C2 (nl)	2000-07-07	Mengsels van polyalkylpiperidine-4-yldicarbonzuuresters als stabilisatoren voor organische materialen.
US20130041148A1 (en)	2013-02-14	Process for the synthesis of n-alkoxyamines
JP5497077B2 (ja)	2014-05-21	トリスレゾリシニルトリアジン
EP0754723B1 (de)	1999-04-28	Synergistisches Stabilisatorgemisch
BE1011940A3 (fr)	2000-03-07	Composes stabilisants et leurs melanges, procede pour les preparer, composition les contenant et procede les utilisant.
NL1018187C2 (nl)	2001-12-28	Stabilisatormengsels.
CA2209008A1 (en)	1997-12-28	Oxazoline compounds as stabilizers
NL1013844C2 (nl)	2001-11-29	Sterisch gehinderde amineverbindingen.
NL1001605C2 (nl)	1997-04-03	Nieuwe 2,2,6,6-tetramethylpiperidine-derivaten voor toepassing als sta- biliseermiddelen voor organische materialen tegen licht, hitte en oxida- tie.
US6177491B1 (en)	2001-01-23	Block oligomers containing 1-Hydrocarbyloxy-2,2,6,6-Tetramethyl-4-piperidyl groups as stabilizers for organic materials
US6353044B1 (en)	2002-03-05	Light-stabilized organic polymers
EP0837064A2 (de)	1998-04-22	Addukte aus Aminen und Epoxyd-HALS und ihre Verwendung als Stabilisatoren
GB2371543A (en)	2002-07-31	3,3,5,5-Tetraalkyl-piperazine-2,6-dione stabilizers
MXPA99010920A (es)	2000-09-04	Oligomeros de bloque que contienen grupos 1-hidrocarbiloxi-2,2,6,6-tetrametil-4-piperidilo como estabilizantes para materiales organicos