NL1011162C2 - Oxopiperazinyl-derivaten en tegen licht gestabiliseerde samenstellingen. - Google Patents

Oxopiperazinyl-derivaten en tegen licht gestabiliseerde samenstellingen. Download PDF

Info

Publication number: NL1011162C2
Authority: NL; Netherlands
Prior art keywords: alkyl; substituted; formula; alkylene; group
Prior art date: 1998-02-02

Application number

NL1011162A

Other languages

English (en)

Dutch (nl)

Other versions

NL1011162A1 (nl

Inventor

Graziano Zagnoni

Stephen Mark Andrews

Alessandro Zedda

Dario Dr Lazzari

Mirko Dr Rossi

Valerio Dr Borzatta

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.)

1998-02-02

Filing date

1999-01-28

Publication date

1999-09-24

1999-01-28 Application filed by Ciba Sc Holding Ag filed Critical Ciba Sc Holding Ag

1999-08-04 Publication of NL1011162A1 publication Critical patent/NL1011162A1/xx

1999-09-24 Application granted granted Critical

1999-09-24 Publication of NL1011162C2 publication Critical patent/NL1011162C2/nl

Links

239000000203 mixture Substances 0.000 title claims description 122
-1 oxyl Chemical group 0.000 claims description 246
150000001875 compounds Chemical class 0.000 claims description 152
125000000217 alkyl group Chemical group 0.000 claims description 142
229910052739 hydrogen Inorganic materials 0.000 claims description 96
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 90
239000001257 hydrogen Substances 0.000 claims description 82
125000002947 alkylene group Chemical group 0.000 claims description 60
238000000034 method Methods 0.000 claims description 59
125000003545 alkoxy group Chemical group 0.000 claims description 51
125000003118 aryl group Chemical group 0.000 claims description 51
125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 49
229920000642 polymer Polymers 0.000 claims description 49
239000000463 material Substances 0.000 claims description 48
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 38
229910052757 nitrogen Inorganic materials 0.000 claims description 37
229910052760 oxygen Inorganic materials 0.000 claims description 37
239000003381 stabilizer Substances 0.000 claims description 34
125000004450 alkenylene group Chemical group 0.000 claims description 32
125000001931 aliphatic group Chemical group 0.000 claims description 31
125000000753 cycloalkyl group Chemical group 0.000 claims description 31
125000003884 phenylalkyl group Chemical group 0.000 claims description 30
239000000654 additive Substances 0.000 claims description 29
125000003342 alkenyl group Chemical group 0.000 claims description 28
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 25
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
239000001301 oxygen Substances 0.000 claims description 23
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 15
BUMXGCXFKGZOCK-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3,3,5,5-tetramethylpiperazin-2-one Chemical compound CC1(C)CN(CCO)C(=O)C(C)(C)N1 BUMXGCXFKGZOCK-UHFFFAOYSA-N 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
238000000576 coating method Methods 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
239000011368 organic material Substances 0.000 claims description 13
239000011593 sulfur Substances 0.000 claims description 13
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 12
125000005724 cycloalkenylene group Chemical group 0.000 claims description 12
125000004956 cyclohexylene group Chemical group 0.000 claims description 12
239000000975 dye Substances 0.000 claims description 12
125000001624 naphthyl group Chemical group 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 11
125000002071 phenylalkoxy group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
230000000087 stabilizing effect Effects 0.000 claims description 10
101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 9
229910052751 metal Inorganic materials 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
229910052708 sodium Inorganic materials 0.000 claims description 9
239000011734 sodium Substances 0.000 claims description 9
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 8
239000011248 coating agent Substances 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
239000000839 emulsion Substances 0.000 claims description 7
125000003700 epoxy group Chemical group 0.000 claims description 7
229920000620 organic polymer Polymers 0.000 claims description 7
239000000049 pigment Substances 0.000 claims description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
239000012965 benzophenone Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
239000011591 potassium Substances 0.000 claims description 6
229910052700 potassium Inorganic materials 0.000 claims description 6
125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 claims description 6
125000004423 acyloxy group Chemical group 0.000 claims description 5
125000001118 alkylidene group Chemical group 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000002993 cycloalkylene group Chemical group 0.000 claims description 5
125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 5
125000000524 functional group Chemical group 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 5
229910052709 silver Inorganic materials 0.000 claims description 5
239000004332 silver Substances 0.000 claims description 5
229920001169 thermoplastic Polymers 0.000 claims description 5
WFGMRESWHYSOKC-UHFFFAOYSA-N 1,3,3,4-tetramethylpiperazin-2-one Chemical group CN1CCN(C)C(C)(C)C1=O WFGMRESWHYSOKC-UHFFFAOYSA-N 0.000 claims description 4
XOEYGHCZKJSLEL-UHFFFAOYSA-N 1-(2-hydroxypropyl)-3,3,5,5-tetramethylpiperazin-2-one Chemical compound CC(O)CN1CC(C)(C)NC(C)(C)C1=O XOEYGHCZKJSLEL-UHFFFAOYSA-N 0.000 claims description 4
239000003963 antioxidant agent Substances 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
239000004611 light stabiliser Substances 0.000 claims description 4
230000000737 periodic effect Effects 0.000 claims description 4
FIJRXCZCDLDNHG-UHFFFAOYSA-N 1-(2-hydroxypropyl)-3,3,4,5,5-pentamethylpiperazin-2-one Chemical compound CC(O)CN1CC(C)(C)N(C)C(C)(C)C1=O FIJRXCZCDLDNHG-UHFFFAOYSA-N 0.000 claims description 3
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 3
HTTGVORJOBRXRJ-UHFFFAOYSA-N 2-(triazin-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=NN=N1 HTTGVORJOBRXRJ-UHFFFAOYSA-N 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
239000004593 Epoxy Substances 0.000 claims description 3
239000000758 substrate Substances 0.000 claims description 3
239000004416 thermosoftening plastic Substances 0.000 claims description 3
FINHMKGKINIASC-UHFFFAOYSA-N Tetramethylpyrazine Chemical compound CC1=NC(C)=C(C)N=C1C FINHMKGKINIASC-UHFFFAOYSA-N 0.000 claims description 2
125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
239000004014 plasticizer Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 15
125000001589 carboacyl group Chemical group 0.000 claims 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
241001331845 Equus asinus x caballus Species 0.000 claims 1
125000000000 cycloalkoxy group Chemical group 0.000 claims 1
230000009974 thixotropic effect Effects 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 58
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
239000000243 solution Substances 0.000 description 38
238000002360 preparation method Methods 0.000 description 37
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
229920001577 copolymer Polymers 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
239000010410 layer Substances 0.000 description 31
239000000047 product Substances 0.000 description 31
238000005481 NMR spectroscopy Methods 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
150000003254 radicals Chemical class 0.000 description 24
125000004435 hydrogen atom Chemical class [H]* 0.000 description 23
239000003921 oil Substances 0.000 description 23
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 22
239000008096 xylene Substances 0.000 description 22
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000004743 Polypropylene Substances 0.000 description 21
229920001155 polypropylene Polymers 0.000 description 21
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
239000003153 chemical reaction reagent Substances 0.000 description 16
150000001412 amines Chemical class 0.000 description 15
239000004417 polycarbonate Substances 0.000 description 15
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 14
230000000996 additive effect Effects 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
239000004952 Polyamide Substances 0.000 description 12
239000003054 catalyst 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
239000007787 solid Substances 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
239000004698 Polyethylene Substances 0.000 description 11
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 11
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238000000921 elemental analysis Methods 0.000 description 11
229920000573 polyethylene Polymers 0.000 description 11
239000000843 powder Substances 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
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 10
229920002857 polybutadiene Polymers 0.000 description 10
238000006116 polymerization reaction Methods 0.000 description 10
108010010803 Gelatin Proteins 0.000 description 9
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239000005062 Polybutadiene Substances 0.000 description 9
125000002252 acyl group Chemical group 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
239000012964 benzotriazole Substances 0.000 description 9
239000008273 gelatin Substances 0.000 description 9
229920000159 gelatin Polymers 0.000 description 9
235000019322 gelatine Nutrition 0.000 description 9
235000011852 gelatine desserts Nutrition 0.000 description 9
229920005989 resin Polymers 0.000 description 9
239000011347 resin Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000007983 Tris buffer Substances 0.000 description 8
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
150000004985 diamines Chemical class 0.000 description 8
229920001684 low density polyethylene Polymers 0.000 description 8
239000004702 low-density polyethylene Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
229920000915 polyvinyl chloride Polymers 0.000 description 8
239000004800 polyvinyl chloride Substances 0.000 description 8
ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 8
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239000002253 acid Substances 0.000 description 7
150000001335 aliphatic alkanes Chemical class 0.000 description 7
238000009835 boiling Methods 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
239000007859 condensation product Substances 0.000 description 7
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238000012545 processing Methods 0.000 description 7
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 6
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239000002585 base Substances 0.000 description 6
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238000005227 gel permeation chromatography Methods 0.000 description 6
238000007641 inkjet printing Methods 0.000 description 6
239000011572 manganese Substances 0.000 description 6
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
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239000002243 precursor Chemical group 0.000 description 6
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
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238000002844 melting Methods 0.000 description 5
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AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 5
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229910014033 C-OH Inorganic materials 0.000 description 4
229910014570 C—OH Inorganic materials 0.000 description 4
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PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000004721 Polyphenylene oxide Substances 0.000 description 4
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239000007868 Raney catalyst Substances 0.000 description 4
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241001104043 Syringa Species 0.000 description 4
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239000006096 absorbing agent Substances 0.000 description 4
150000001252 acrylic acid derivatives Chemical class 0.000 description 4
229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 4
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239000004927 clay Substances 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 4
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FDAKZQLBIFPGSV-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)NC(C)(C)C1 FDAKZQLBIFPGSV-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
ZRPOKHXBOZQSOX-UHFFFAOYSA-N n-heptadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCC ZRPOKHXBOZQSOX-UHFFFAOYSA-N 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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150000002816 nickel compounds Chemical class 0.000 description 1
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RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
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XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
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235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
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230000001012 protector Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
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238000010526 radical polymerization reaction Methods 0.000 description 1
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CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
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150000004760 silicates Chemical class 0.000 description 1
229910052814 silicon oxide Inorganic materials 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
235000010265 sodium sulphite Nutrition 0.000 description 1
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125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
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150000003568 thioethers Chemical class 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
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239000011732 tocopherol Substances 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
125000000297 undecanoyl 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])[H] 0.000 description 1
125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920006337 unsaturated polyester resin Polymers 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
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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
239000004711 α-olefin Substances 0.000 description 1
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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
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Classifications

- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
- G03C1/8155—Organic compounds therefor
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0633—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
- 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
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings

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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)
Physics & Mathematics (AREA)
Materials Engineering (AREA)
Engineering & Computer Science (AREA)
General Physics & Mathematics (AREA)
Plural Heterocyclic Compounds (AREA)
Compositions Of Macromolecular Compounds (AREA)
Hydrogenated Pyridines (AREA)
Detergent Compositions (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paints Or Removers (AREA)

NL1011162A 1998-02-02 1999-01-28 Oxopiperazinyl-derivaten en tegen licht gestabiliseerde samenstellingen. NL1011162C2 (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP98810074		1998-02-02
EP98810074		1998-02-02

Publications (2)

Publication Number	Publication Date
NL1011162A1 NL1011162A1 (nl)	1999-08-04
NL1011162C2 true NL1011162C2 (nl)	1999-09-24

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ID=8235916

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL1011162A NL1011162C2 (nl)	1998-02-02	1999-01-28	Oxopiperazinyl-derivaten en tegen licht gestabiliseerde samenstellingen.

Country Status (19)

Country	Link
US (1)	US6642383B2 (fr)
JP (1)	JPH11269155A (fr)
KR (1)	KR19990072373A (fr)
CN (2)	CN1198806C (fr)
AR (1)	AR014952A1 (fr)
BE (1)	BE1011972A3 (fr)
BR (1)	BR9900277A (fr)
CA (1)	CA2260568A1 (fr)
CZ (1)	CZ32699A3 (fr)
DE (1)	DE19903870A1 (fr)
ES (1)	ES2158768B1 (fr)
FR (1)	FR2777005B1 (fr)
GB (1)	GB2333774B (fr)
ID (1)	ID21840A (fr)
IT (1)	IT1307736B1 (fr)
NL (1)	NL1011162C2 (fr)
SG (1)	SG80008A1 (fr)
TW (1)	TW557313B (fr)
ZA (1)	ZA99769B (fr)

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US6905525B2 (en)	2001-04-02	2005-06-14	Ciba Specialty Chemicals Corporation	Candle wax stabilized with piperazinones
US6544305B2 (en)	2001-04-02	2003-04-08	Ciba Specialty Chemicals Corporation	Candle wax stabilized with piperazinones
US7153896B2 (en) *	2003-11-14	2006-12-26	Eastman Kodak Company	Element for protein microarrays
BR112014003974B1 (pt) *	2011-08-26	2019-10-01	Dow Global Technologies Llc	Processo para fazer uma piperazina mono- ou di-alcoxilada através da alcoxilação de um composto de piperazina
TWI447154B (zh)	2012-11-27	2014-08-01	Ind Tech Res Inst	聚氯乙烯製品與其表面處理方法

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1999
- 1999-01-04 TW TW088100088A patent/TW557313B/zh not_active IP Right Cessation
- 1999-01-21 SG SG9900130A patent/SG80008A1/en unknown
- 1999-01-26 ID IDP990053D patent/ID21840A/id unknown
- 1999-01-26 GB GB9901574A patent/GB2333774B/en not_active Expired - Fee Related
- 1999-01-28 NL NL1011162A patent/NL1011162C2/nl not_active IP Right Cessation
- 1999-01-29 CA CA002260568A patent/CA2260568A1/fr not_active Abandoned
- 1999-01-29 AR ARP990100371A patent/AR014952A1/es unknown
- 1999-01-29 CZ CZ99326A patent/CZ32699A3/cs unknown
- 1999-01-29 JP JP11022900A patent/JPH11269155A/ja not_active Withdrawn
- 1999-02-01 IT IT1999MI000180A patent/IT1307736B1/it active
- 1999-02-01 BR BR9900277-9A patent/BR9900277A/pt not_active IP Right Cessation
- 1999-02-01 FR FR9901080A patent/FR2777005B1/fr not_active Expired - Fee Related
- 1999-02-01 BE BE9900061A patent/BE1011972A3/fr not_active IP Right Cessation
- 1999-02-01 DE DE19903870A patent/DE19903870A1/de not_active Ceased
- 1999-02-01 ZA ZA9900769A patent/ZA99769B/xx unknown
- 1999-02-01 ES ES009900199A patent/ES2158768B1/es not_active Expired - Fee Related
- 1999-02-02 KR KR1019990003387A patent/KR19990072373A/ko not_active Ceased
- 1999-02-02 CN CNB991017439A patent/CN1198806C/zh not_active Expired - Fee Related
- 1999-02-02 CN CN2004101022409A patent/CN1660821A/zh active Pending
2001
- 2001-05-14 US US09/855,905 patent/US6642383B2/en not_active Expired - Fee Related

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Also Published As

Publication number	Publication date
US20020115859A1 (en)	2002-08-22
AR014952A1 (es)	2001-04-11
CN1660821A (zh)	2005-08-31
SG80008A1 (en)	2001-04-17
FR2777005A1 (fr)	1999-10-08
US6642383B2 (en)	2003-11-04
JPH11269155A (ja)	1999-10-05
KR19990072373A (ko)	1999-09-27
CZ32699A3 (cs)	1999-09-15
GB2333774B (en)	2000-07-19
BR9900277A (pt)	2000-05-30
NL1011162A1 (nl)	1999-08-04
GB9901574D0 (en)	1999-03-17
CA2260568A1 (fr)	1999-08-02
ZA99769B (en)	1999-08-02
FR2777005B1 (fr)	2004-12-17
ES2158768B1 (es)	2002-03-01
ITMI990180A1 (it)	2000-08-01
CN1234400A (zh)	1999-11-10
ID21840A (id)	1999-08-05
TW557313B (en)	2003-10-11
DE19903870A1 (de)	1999-08-05
ES2158768A1 (es)	2001-09-01
IT1307736B1 (it)	2001-11-19
CN1198806C (zh)	2005-04-27
BE1011972A3 (fr)	2000-03-07
GB2333774A (en)	1999-08-04

Legal Events

Date	Code	Title	Description
1999-12-01	PD2B	A search report has been drawn up
2006-10-02	VD1	Lapsed due to non-payment of the annual fee	Effective date: 20060801

Publication	Publication Date	Title
EP1015436B1 (fr)	2003-04-16	Morpholinones en tant qu'agents de stabilite a la lumiere
NL1006140C2 (nl)	2000-07-07	Mengsels van polyalkylpiperidine-4-yldicarbonzuuresters als stabilisatoren voor organische materialen.
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.
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.
US6642383B2 (en)	2003-11-04	Oxopiperazinyl derivatives and light stabilized compositions
BE1012760A3 (fr)	2001-03-06	Composition stabilisee, compose contenu dans celle-ci comme stabilisant et utilisation de ce compose.
BE1013526A5 (fr)	2002-03-05	Composes stabilisants, compositions et produits les contenant et leur procede d'utilisation.
EP1133490B1 (fr)	2005-07-27	Derives de piperazinone
EP1282605B1 (fr)	2008-01-02	Derives de thioimidazolidine comme photostabilisants dans des polymeres
FR2746799A1 (fr)	1997-10-03	Composes stabilisants, composition les contenant et leur procede d'utilisation
NL9400515A (nl)	1994-11-01	Nieuwe piperidine-triazine-verbindingen die geschikt zijn voor gebruik als stabiliseermiddelen voor organische materialen.
US20090318592A1 (en)	2009-12-24	Process for the Synthesis of Amine Ethers
FR2763948A1 (fr)	1998-12-04	Produits et melanges stabilisants, composition les contenant et procede les utilisant
GB2377441A (en)	2003-01-15	Piperazinone derivatives
DE19633125A1 (de)	1997-03-13	Offenkettige und cyclische Monophosphonite