BE1014990A5 - Procede de preparation d'ethers d'amine a empechement sterique, composes de cette classe et leur utilisation pour stabiliser une matiere organique. - Google Patents

Procede de preparation d'ethers d'amine a empechement sterique, composes de cette classe et leur utilisation pour stabiliser une matiere organique. Download PDF

Info

Publication number: BE1014990A5
Authority: BE; Belgium
Prior art keywords: group; formula; alkyl; substituted; independently
Prior art date: 1998-02-25

Application number

BE9900127A

Other languages

English (en)

French (fr)

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

2004-08-03

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

2004-08-03 Application granted granted Critical

2004-08-03 Publication of BE1014990A5 publication Critical patent/BE1014990A5/fr

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150000001875 compounds Chemical class 0.000 title claims abstract description 152
238000000034 method Methods 0.000 title claims abstract description 41
-1 amine ethers Chemical class 0.000 title claims description 213
239000005416 organic matter Substances 0.000 title claims description 10
230000002265 prevention Effects 0.000 title 1
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 42
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
239000003381 stabilizer Substances 0.000 claims abstract description 36
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 28
230000008569 process Effects 0.000 claims abstract description 27
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 20
238000002360 preparation method Methods 0.000 claims abstract description 18
125000005647 linker group Chemical group 0.000 claims abstract description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
238000007254 oxidation reaction Methods 0.000 claims abstract description 13
125000004122 cyclic group Chemical group 0.000 claims abstract description 12
230000003647 oxidation Effects 0.000 claims abstract description 12
239000003063 flame retardant Substances 0.000 claims abstract description 9
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 7
239000000203 mixture Substances 0.000 claims description 104
229910052739 hydrogen Inorganic materials 0.000 claims description 84
239000001257 hydrogen Substances 0.000 claims description 80
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 57
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
229910052799 carbon Inorganic materials 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 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
125000001931 aliphatic group Chemical group 0.000 claims description 40
150000001721 carbon Chemical group 0.000 claims description 40
125000003118 aryl group Chemical group 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
229910052760 oxygen Inorganic materials 0.000 claims description 34
239000001301 oxygen Substances 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 28
150000002367 halogens Chemical class 0.000 claims description 28
238000000576 coating method Methods 0.000 claims description 27
125000003342 alkenyl group Chemical group 0.000 claims description 26
125000002947 alkylene group Chemical group 0.000 claims description 26
125000000753 cycloalkyl group Chemical group 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 23
125000005843 halogen group Chemical group 0.000 claims description 20
229910052751 metal Inorganic materials 0.000 claims description 20
239000002184 metal Substances 0.000 claims description 20
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 19
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 19
229910052698 phosphorus Inorganic materials 0.000 claims description 19
239000011574 phosphorus Substances 0.000 claims description 19
239000011230 binding agent Substances 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
125000005842 heteroatom Chemical group 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
125000003884 phenylalkyl group Chemical group 0.000 claims description 15
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 12
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 12
150000002430 hydrocarbons Chemical class 0.000 claims description 12
239000000463 material Substances 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
229910052717 sulfur Inorganic materials 0.000 claims description 12
239000011593 sulfur Substances 0.000 claims description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
229920000620 organic polymer Polymers 0.000 claims description 11
230000015556 catabolic process Effects 0.000 claims description 10
239000011248 coating agent Substances 0.000 claims description 10
238000006731 degradation reaction Methods 0.000 claims description 10
OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 10
229920002554 vinyl polymer Polymers 0.000 claims description 10
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
229920001169 thermoplastic Polymers 0.000 claims description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
229930195733 hydrocarbon Natural products 0.000 claims description 8
238000005984 hydrogenation reaction Methods 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
125000002993 cycloalkylene group Chemical group 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 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 Substances 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000000732 arylene group Chemical group 0.000 claims description 6
125000001589 carboacyl group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000000049 pigment Substances 0.000 claims description 6
125000001424 substituent 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 5
239000004215 Carbon black (E152) Substances 0.000 claims description 5
239000006096 absorbing agent Substances 0.000 claims description 5
230000026030 halogenation Effects 0.000 claims description 5
238000005658 halogenation reaction Methods 0.000 claims description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
230000000087 stabilizing effect Effects 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#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
239000007800 oxidant agent Substances 0.000 claims description 4
150000002978 peroxides Chemical class 0.000 claims description 4
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
239000011368 organic material Substances 0.000 claims description 3
230000001590 oxidative effect Effects 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
125000006839 xylylene group Chemical group 0.000 claims description 3
125000004642 (C1-C12) alkoxy group Chemical group 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
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
239000012965 benzophenone Substances 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
125000001183 hydrocarbyl group Chemical group 0.000 claims 3
150000001735 carboxylic acids Chemical class 0.000 claims 2
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 1
125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims 1
150000008366 benzophenones Chemical class 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 50
239000000047 product Substances 0.000 description 50
150000003254 radicals Chemical class 0.000 description 41
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 36
229920000642 polymer Polymers 0.000 description 35
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 34
239000003054 catalyst Substances 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
238000003756 stirring Methods 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
229920001684 low density polyethylene Polymers 0.000 description 22
239000004702 low-density polyethylene Substances 0.000 description 22
239000008199 coating composition Substances 0.000 description 21
239000003973 paint Substances 0.000 description 21
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
150000001412 amines Chemical class 0.000 description 19
239000012074 organic phase Substances 0.000 description 18
229910000027 potassium carbonate Inorganic materials 0.000 description 18
235000011181 potassium carbonates Nutrition 0.000 description 16
239000004743 Polypropylene Substances 0.000 description 15
150000002148 esters Chemical class 0.000 description 15
229920001155 polypropylene Polymers 0.000 description 15
229920000178 Acrylic resin Polymers 0.000 description 14
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
239000000843 powder Substances 0.000 description 14
229920005989 resin Polymers 0.000 description 14
239000011347 resin Substances 0.000 description 14
239000007787 solid Substances 0.000 description 14
239000004925 Acrylic resin Substances 0.000 description 13
239000004952 Polyamide Substances 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
229920002647 polyamide Polymers 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 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
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
239000007983 Tris buffer Substances 0.000 description 11
230000006641 stabilisation Effects 0.000 description 11
238000011105 stabilization Methods 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
239000007859 condensation product Substances 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
239000011572 manganese Substances 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
101150041968 CDC13 gene Proteins 0.000 description 9
239000004594 Masterbatch (MB) Substances 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 9
239000000654 additive 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
229920000728 polyester Polymers 0.000 description 9
239000004814 polyurethane Substances 0.000 description 9
239000000758 substrate Substances 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
239000005062 Polybutadiene Substances 0.000 description 8
239000004698 Polyethylene Substances 0.000 description 8
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
238000001723 curing Methods 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
229920000573 polyethylene Polymers 0.000 description 8
229910001220 stainless steel Inorganic materials 0.000 description 8
239000010935 stainless steel Substances 0.000 description 8
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
150000001993 dienes Chemical class 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
229920002635 polyurethane Polymers 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 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
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000003431 cross linking reagent Substances 0.000 description 6
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
229920001971 elastomer Polymers 0.000 description 6
229940093476 ethylene glycol Drugs 0.000 description 6
239000004611 light stabiliser Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
150000002739 metals Chemical class 0.000 description 6
AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 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
229920000915 polyvinyl chloride Polymers 0.000 description 6
239000004800 polyvinyl chloride Substances 0.000 description 6
239000002966 varnish Substances 0.000 description 6
239000004593 Epoxy Substances 0.000 description 5
239000004721 Polyphenylene oxide Substances 0.000 description 5
150000001252 acrylic acid derivatives Chemical class 0.000 description 5
229920000180 alkyd Polymers 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
239000012964 benzotriazole Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000003822 epoxy resin Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
230000009931 harmful effect Effects 0.000 description 5
229920001903 high density polyethylene Polymers 0.000 description 5
239000004700 high-density polyethylene Substances 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
229910052748 manganese Inorganic materials 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000178 monomer Substances 0.000 description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
229940117969 neopentyl glycol Drugs 0.000 description 5
229920000098 polyolefin Polymers 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
150000005846 sugar alcohols Polymers 0.000 description 5
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BLBLVDQTHWVGRA-UHFFFAOYSA-N n-butyl-3-[4-[4-(butylamino)-1,2,2,6,6-pentamethylpiperidin-3-yl]-6-chloro-1,3,5-triazin-2-yl]-1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)N(C)C(C)(C)C1C1=NC(Cl)=NC(C2C(N(C)C(C)(C)CC2NCCCC)(C)C)=N1 BLBLVDQTHWVGRA-UHFFFAOYSA-N 0.000 description 1
BYYFPVDBAHOLDX-UHFFFAOYSA-N n-dodecyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCCCCCCCCCC)C1=CC=CC=C1 BYYFPVDBAHOLDX-UHFFFAOYSA-N 0.000 description 1
LRUUZFQPCUFYPV-UHFFFAOYSA-N n-dodecyldodecan-1-imine oxide Chemical compound CCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCC LRUUZFQPCUFYPV-UHFFFAOYSA-N 0.000 description 1
GBMIPYGHTZRCRH-UHFFFAOYSA-N n-ethylethanimine oxide Chemical compound CC[N+]([O-])=CC GBMIPYGHTZRCRH-UHFFFAOYSA-N 0.000 description 1
ZRPOKHXBOZQSOX-UHFFFAOYSA-N n-heptadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCC ZRPOKHXBOZQSOX-UHFFFAOYSA-N 0.000 description 1
DBCWENWKZARTGU-UHFFFAOYSA-N n-heptadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC=[N+]([O-])CCCCCCCCCCCCCCCCC DBCWENWKZARTGU-UHFFFAOYSA-N 0.000 description 1
GCDJFNYVSDFWDB-UHFFFAOYSA-N n-hexadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC GCDJFNYVSDFWDB-UHFFFAOYSA-N 0.000 description 1
FHAFFFSIDLDWQA-UHFFFAOYSA-N n-hexadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC=[N+]([O-])CCCCCCCCCCCCCCCC FHAFFFSIDLDWQA-UHFFFAOYSA-N 0.000 description 1
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 1
MCMMSXFAWOGWQE-UHFFFAOYSA-N n-octadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC MCMMSXFAWOGWQE-UHFFFAOYSA-N 0.000 description 1
HORBOHJHQGXXOR-UHFFFAOYSA-N n-octadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCCC HORBOHJHQGXXOR-UHFFFAOYSA-N 0.000 description 1
QXJGVICBAANVMZ-UHFFFAOYSA-N n-octyloctan-1-imine oxide Chemical compound CCCCCCCC[N+]([O-])=CCCCCCCC QXJGVICBAANVMZ-UHFFFAOYSA-N 0.000 description 1
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
SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-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
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
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
239000004843 novolac epoxy resin Substances 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
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
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 description 1
230000003287 optical effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
238000010422 painting Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
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
229920001568 phenolic resin Polymers 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
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
150000003003 phosphines Chemical class 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003018 phosphorus compounds 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
150000003053 piperidines Chemical class 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
229920003229 poly(methyl methacrylate) 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
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002312 polyamide-imide Polymers 0.000 description 1
229920002480 polybenzimidazole 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
239000004848 polyfunctional curative Substances 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920001021 polysulfide 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
235000021395 porridge Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl 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
238000010526 radical polymerization reaction Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 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
229910052895 riebeckite Inorganic materials 0.000 description 1
229910052707 ruthenium 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
239000000565 sealant Substances 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
IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 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
125000006850 spacer group Chemical group 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure 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
229920006249 styrenic copolymer Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 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
229920005613 synthetic organic polymer Polymers 0.000 description 1
229920001059 synthetic polymer Polymers 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
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000000000 tetracarboxylic acids Chemical class 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
229920002725 thermoplastic elastomer Polymers 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
235000019149 tocopherols Nutrition 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
230000017105 transposition Effects 0.000 description 1
229940055764 triaz Drugs 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
SHEXSXZCZQBTFI-UHFFFAOYSA-N tridecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)-2-sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)C(S)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SHEXSXZCZQBTFI-UHFFFAOYSA-N 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
239000003981 vehicle Substances 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
BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 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
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 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

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
- 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
- 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
- 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

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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)

BE9900127A 1998-02-25 1999-02-25 Procede de preparation d'ethers d'amine a empechement sterique, composes de cette classe et leur utilisation pour stabiliser une matiere organique. BE1014990A5 (fr)

Applications Claiming Priority (2)

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

Publications (1)

Publication Number	Publication Date
BE1014990A5 true BE1014990A5 (fr)	2004-08-03

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ID=26331570

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE9900127A BE1014990A5 (fr)	1998-02-25	1999-02-25	Procede de preparation d'ethers d'amine a empechement sterique, composes de cette classe et leur utilisation pour stabiliser une matiere organique.

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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CA2576816C (en) *	2004-08-31	2012-10-16	Ciba Specialty Chemicals Holding Inc.	Stabilization of organic materials
PL1807395T3 (pl) *	2004-11-02	2016-06-30	Basf Se	Sposób syntezy n-alkoksyamin
ES2388886T3 (es) *	2006-11-23	2012-10-19	Basf Se	Procedimiento para la preparación de N-alilaminas terciarias estéricamente impedidas
KR101608094B1 (ko) *	2007-12-21	2016-03-31	바스프 에스이	나노 구조 ｕｖ 흡수제
KR20120043090A (ko) *	2009-08-18	2012-05-03	바스프 에스이	안정화된 중합체 봉지재를 가진 광전 모듈
DK2475655T3 (en) *	2009-09-10	2018-01-15	Basf Se	STERICALLY HINDED AMIN STABILIZER
EP2630137B1 (en) *	2010-10-20	2015-04-01	Basf Se	Sterically hindered amine light stabilizers with mixed functionalization
EP2514800B2 (de)	2011-04-21	2018-03-07	Merck Patent GmbH	Verbindungen und flüssigkristallines Medium
EP3526288B1 (en)	2016-10-14	2021-08-04	Basf Se	Stabilizer composition
CA3055864A1 (en) *	2017-03-28	2018-10-04	Basf Se	Light stabilizer mixture
CN109503554B (zh) *	2018-12-13	2020-10-30	天津利安隆新材料股份有限公司	一种聚合型受阻胺类光稳定剂ha-88的制备方法
JP7515497B2 (ja) *	2019-03-08	2024-07-12	ビーエーエスエフソシエタス・ヨーロピア	立体障害アミン安定剤混合物
CN112126060B (zh)	2019-06-25	2022-05-31	北京天罡助剂有限责任公司	一种聚合型高分子空间位阻胺及其制备方法
CN113354813B (zh) *	2021-06-02	2023-07-04	宿迁联盛科技股份有限公司	一种低碱性受阻胺光稳定剂nor 371的制备方法
JP2025511683A (ja)	2022-04-04	2025-04-16	ジェネアスケム・アーゲー	立体障害ニトロキシルエーテルを調製するためのプロセス
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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

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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
ES2159462A1 (es)	2001-10-01
CN100384826C (zh)	2008-04-30
NL1011394C2 (nl)	1999-10-26
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
2019-03-25	MK	Patent expired because of reaching the maximum lifetime of a patent	Effective date: 20190225

Publication	Publication Date	Title
US6677451B2 (en)	2004-01-13	Preparation of sterically hindered amine ethers
FR2777004A1 (fr)	1999-10-08	Procede de preparation d'ethers d'amine a empechement sterique, composes de cette classe et leur utilisation pour stabiliser une matiere organique
BE1012526A5 (fr)	2000-12-05	Melange stabilisant, composition le contenant et procede l'utilisant pour stabiliser une matiere organique.
BE1012428A3 (fr)	2000-11-07	Hydroxyphenyltriazines et compositions de polymeres organiques stabilisees par des hydroxyphenyltriazines.
BE1010551A3 (fr)	1998-10-06	Composition de polymere organique synthetique stabilise, procede de stabilisation du polymere et utilisation de la composition.
JP4907823B2 (ja)	2012-04-04	安定剤混合物
US20110015315A1 (en)	2011-01-20	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
BE1011937A3 (fr)	2000-03-07	Compose stabilisant, composition le contenant et procede l'utilisant.
BE1011940A3 (fr)	2000-03-07	Composes stabilisants et leurs melanges, procede pour les preparer, composition les contenant et procede les utilisant.
BE1009750A3 (fr)	1997-07-01	Composes de piperidine contenant des groupes silicies, composition les contenant et procede les utilisant pour stabiliser des matieres organiques.
FR2809739A1 (fr)	2001-12-07	Melanges de stabilisants
JPH10114760A (ja)	1998-05-06	安定剤としてのオキサゾリン化合物
BE1013528A3 (fr)	2002-03-05	Produit stabilisant, comopsition le contenant et son procede d'utilisation.
BE1011939A3 (fr)	2000-03-07	Produits stabilisants et leurs melanges composition les contenant et procede les utilisant.
BE1012760A3 (fr)	2001-03-06	Composition stabilisee, compose contenu dans celle-ci comme stabilisant et utilisation de ce compose.
BE1011972A3 (fr)	2000-03-07	Compose stabilisant, composition le contenant et son utilisation.
BE1011938A3 (fr)	2000-03-07	Produits et melanges stabilisants, composition les contenant et procede les utilisant.
BE1011936A3 (fr)	2000-03-07	Produits et melanges stabilisants, composition les contenant et procede les utilisant.