NL195036C - Synthetische polymeer met stabilisator en (1-hydrocarbyloxy-2,2,6,6-tetraalkylpiperidine)-1,3,5-triazine-derivaat daarvoor. - Google Patents
Synthetische polymeer met stabilisator en (1-hydrocarbyloxy-2,2,6,6-tetraalkylpiperidine)-1,3,5-triazine-derivaat daarvoor. Download PDFInfo
- Publication number
- NL195036C NL195036C NL9300751A NL9300751A NL195036C NL 195036 C NL195036 C NL 195036C NL 9300751 A NL9300751 A NL 9300751A NL 9300751 A NL9300751 A NL 9300751A NL 195036 C NL195036 C NL 195036C
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- carbon atoms
- bis
- tetramethylpiperidin
- butylamino
- Prior art date
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- 229920001059 synthetic polymer Polymers 0.000 title claims description 11
- 239000003381 stabilizer Substances 0.000 title description 27
- 150000001875 compounds Chemical class 0.000 claims description 122
- -1 piperazine-1,4-diyl moiety Chemical group 0.000 claims description 98
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 125000006309 butyl amino group Chemical group 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 31
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 18
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 239000011521 glass Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 8
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229960002684 aminocaproic acid Drugs 0.000 claims description 4
- 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 4
- 238000003818 flash chromatography Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003918 triazines Chemical class 0.000 claims description 4
- 230000002411 adverse Effects 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000002274 desiccant Substances 0.000 claims description 3
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000466 oxiranyl group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- XPLIZFLVQHXHRB-UHFFFAOYSA-N 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1OC1CCCCC1 XPLIZFLVQHXHRB-UHFFFAOYSA-N 0.000 claims description 2
- CRJHAHKKNZLODZ-UHFFFAOYSA-N 2-[[4,6-bis[4-(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl)butylamino]-1,3,5-triazin-2-yl]-(2-hydroxyethyl)amino]ethanol Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1CCCCNC1=NC(NCCCCC2CC(C)(C)N(OCCCCCCCC)C(C)(C)C2)=NC(N(CCO)CCO)=N1 CRJHAHKKNZLODZ-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 2
- FSHFXNVZNMBWPO-UHFFFAOYSA-N N-[4-(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl)butyl]-1,3,5-triazin-2-amine Chemical compound C(CCCCCCC)ON1C(CC(CC1(C)C)CCCCNC1=NC=NC=N1)(C)C FSHFXNVZNMBWPO-UHFFFAOYSA-N 0.000 claims 2
- 238000004587 chromatography analysis Methods 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 239000006188 syrup Substances 0.000 claims 2
- 235000020357 syrup Nutrition 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 17
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 description 10
- 239000011707 mineral Substances 0.000 description 10
- 235000010755 mineral Nutrition 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 210000003298 dental enamel Anatomy 0.000 description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 6
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- 238000006068 polycondensation reaction Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
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- 230000003647 oxidation Effects 0.000 description 5
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- 229920000307 polymer substrate Polymers 0.000 description 5
- CLUHWBURHNNGPK-UHFFFAOYSA-M sodium;6-aminohexanoate Chemical compound [Na+].NCCCCCC([O-])=O CLUHWBURHNNGPK-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000087 stabilizing effect Effects 0.000 description 5
- 239000004471 Glycine Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 3
- MCLXKFUCPVGZEN-UHFFFAOYSA-N 4,6-dichloro-1,3,5-triazin-2-amine Chemical compound NC1=NC(Cl)=NC(Cl)=N1 MCLXKFUCPVGZEN-UHFFFAOYSA-N 0.000 description 3
- YZXTWMQYSSMUFH-UHFFFAOYSA-N 4-[6-(1-amino-2,2,6,6-tetramethylpiperidin-4-yl)hexyl]-2,2,6,6-tetramethylpiperidin-1-amine Chemical compound C1C(C)(C)N(N)C(C)(C)CC1CCCCCCC1CC(C)(C)N(N)C(C)(C)C1 YZXTWMQYSSMUFH-UHFFFAOYSA-N 0.000 description 3
- SMPQMYLDYRJSSW-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis[4-(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl)butyl]-1,3,5-triazine-2,4-diamine Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1CCCCNC1=NC(Cl)=NC(NCCCCC2CC(C)(C)N(OCCCCCCCC)C(C)(C)C2)=N1 SMPQMYLDYRJSSW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- QZOKXAUBQJGXNT-UHFFFAOYSA-N n-[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl]-1,3,5-triazin-2-amine Chemical compound C1C(C)(C)N(OC2CCCCC2)C(C)(C)CC1CCCCNC1=NC=NC=N1 QZOKXAUBQJGXNT-UHFFFAOYSA-N 0.000 description 3
- 150000003053 piperidines Chemical class 0.000 description 3
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
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- 238000003860 storage Methods 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 2
- DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- IESVFTNUSZYHKD-UHFFFAOYSA-N 2-[[4,6-bis[4-(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl)butylamino]-1,3,5-triazin-2-yl]amino]ethanol Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1CCCCNC1=NC(NCCO)=NC(NCCCCC2CC(C)(C)N(OCCCCCCCC)C(C)(C)C2)=N1 IESVFTNUSZYHKD-UHFFFAOYSA-N 0.000 description 2
- RWHKJOHWSHGJIF-UHFFFAOYSA-N 2-n,4-n-bis[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl]-1,3,5-triazine-2,4,6-triamine Chemical compound C1C(C)(C)N(OC2CCCCC2)C(C)(C)CC1CCCCNC(N=1)=NC(N)=NC=1NCCCCC(CC1(C)C)CC(C)(C)N1OC1CCCCC1 RWHKJOHWSHGJIF-UHFFFAOYSA-N 0.000 description 2
- WEMYJYSLHKLYKZ-UHFFFAOYSA-N 2-n,4-n-bis[4-(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl)butyl]-1,3,5-triazine-2,4,6-triamine Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1CCCCNC1=NC(N)=NC(NCCCCC2CC(C)(C)N(OCCCCCCCC)C(C)(C)C2)=N1 WEMYJYSLHKLYKZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Polyurethanes Or Polyureas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87867892 | 1992-05-05 | ||
| US07/878,678 US5216156A (en) | 1992-05-05 | 1992-05-05 | Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NL9300751A NL9300751A (nl) | 1993-12-01 |
| NL195036C true NL195036C (nl) | 2003-06-25 |
Family
ID=25372567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL9300751A NL195036C (nl) | 1992-05-05 | 1993-05-04 | Synthetische polymeer met stabilisator en (1-hydrocarbyloxy-2,2,6,6-tetraalkylpiperidine)-1,3,5-triazine-derivaat daarvoor. |
Country Status (16)
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1271711B (it) * | 1994-11-09 | 1997-06-04 | Ciba Geigy Spa | Derivati della 2,2,6,6-tetrametilpiperidina utili come stabilizzanti alla luce, al calore e all'ossidazione per materiali organici |
| US6037441A (en) * | 1996-12-18 | 2000-03-14 | Basf Corporation | Non-acrylic durability enhancing agents, method therefore and cured coating compositions containing the same |
| US6166148A (en) * | 1996-12-18 | 2000-12-26 | Basf Corporation | Durability enhancing agents, method therefore and cured coating compositions containing the same |
| US6147163A (en) * | 1996-12-18 | 2000-11-14 | Basf Corporation | Acrylic oligomeric and polymeric durability enhancing agents, method therefore and cured coating compositions containing the same |
| US6599963B2 (en) | 1997-06-30 | 2003-07-29 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| US5844026A (en) * | 1997-06-30 | 1998-12-01 | Ciba Specialty Chemicals Corporation | N,N',N''-tris{2,4-bis Hydrocarbyloxy-2,2,6,6-tetra-methylpiperidin-4-yl)alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipropylamines, their isomers and bridged derivatives and polymer compositions stabilized therewith |
| US6472456B1 (en) * | 1997-06-30 | 2002-10-29 | Ciba Specialty Chemicals Corp. | Flame retardant compositions |
| US6383716B1 (en) | 1997-08-22 | 2002-05-07 | Asahi Kasei Kabushiki Kaisha | Stable photosensitive resin composition |
| CN1280576A (zh) * | 1997-12-08 | 2001-01-17 | Cytec技术有限公司 | 吗啉代封端的受阻胺取代的氨基三嗪和其作为光稳定剂的应用 |
| SG74700A1 (en) * | 1998-02-25 | 2000-08-22 | Ciba Sc Holding Ag | Preparation of sterically hindered amine ethers |
| ITMI980366A1 (it) | 1998-02-25 | 1999-08-25 | Ciba Spec Chem Spa | Preparazione di eteri amminici stericamente impediti |
| US6051164A (en) * | 1998-04-30 | 2000-04-18 | Cytec Technology Corp. | Methods and compositions for protecting polymers from UV light |
| AU738331B2 (en) * | 1999-02-19 | 2001-09-13 | Asahi Kasei Kabushiki Kaisha | Stable photosensitive resin composition |
| TWI273115B (en) * | 2000-12-12 | 2007-02-11 | Ciba Sc Holding Ag | Improved weatherability of flame retardant polyolefin |
| CA2467711C (en) * | 2001-12-10 | 2011-11-01 | Ciba Specialty Chemicals Holding Inc. | Flame retardant compositions |
| US7323502B2 (en) * | 2002-03-12 | 2008-01-29 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| US20040002559A1 (en) * | 2002-04-10 | 2004-01-01 | Malisa Troutman | Flame retardant coatings |
| MY139230A (en) * | 2002-10-17 | 2009-08-28 | Ciba Holding Inc | Flame retardant polymeric electrical parts |
| US7550599B2 (en) * | 2003-02-26 | 2009-06-23 | Ciba Specialty Chemicals Corporation | Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines |
| ATE539058T1 (de) * | 2003-02-26 | 2012-01-15 | Basf Se | Wasserverträgliche sterisch gehinderte hydroxysubstitutierte alkoxyamine |
| SI1807395T1 (sl) | 2004-11-02 | 2016-04-29 | Basf Se | Proces za sintezo N-alkoksiaminov |
| WO2007016175A1 (en) * | 2005-07-28 | 2007-02-08 | Guasch Michael N | Fuel repellent compositions, fabrics and articles |
| EP1787989A1 (de) * | 2005-11-17 | 2007-05-23 | Degussa GmbH | Triazinverbindungen mit Aminogruppen- und Carboxygruppen-haltigen Substituenten |
| ES2553340T3 (es) * | 2007-12-12 | 2015-12-07 | Rigel Pharmaceuticals, Inc. | Compuestos de carboxamida, sulfonamida y amina para trastornos metabólicos |
| US20120145241A1 (en) * | 2009-08-18 | 2012-06-14 | Basf Se | Photovoltaic module with stabilized polymeric encapsulant |
| JP5556395B2 (ja) * | 2009-08-28 | 2014-07-23 | Ｊｓｒ株式会社 | 液晶配向剤、液晶配向膜、液晶表示素子 |
| TWI471095B (zh) * | 2009-12-21 | 2015-02-01 | Nippon Soda Co | 環胺化合物及殺蟎劑 |
| AR081721A1 (es) | 2010-02-25 | 2012-10-17 | Nippon Soda Co | Compuesto de amina ciclica y acaricida |
| RU2012145171A (ru) | 2010-03-25 | 2014-04-27 | Басф Се | Огнезащитные композиции солей фосфиновых кислот и нитроксильных производных |
| US8729163B2 (en) | 2010-07-28 | 2014-05-20 | Basf Se | Phosphinic acid hydrazide flame retardant compositions |
| WO2012013565A1 (en) | 2010-07-29 | 2012-02-02 | Basf Se | Phosphinic acid hydrazide flame retardant compositions |
| JP6246223B2 (ja) | 2012-10-23 | 2017-12-13 | ビーエーエスエフ エスイー | ポリマー安定剤基を含有するエチレン性不飽和オリゴマー |
| EP2743299A1 (de) | 2012-12-12 | 2014-06-18 | Zylum Beteiligungsgesellschaft mbH & Co. Patente II KG | Synergistische Zusammensetzung und deren Verwendung als Flammschutzmittel |
| EP2816097A1 (en) | 2013-06-18 | 2014-12-24 | Shell Internationale Research Maatschappij B.V. | Lubricating oil composition |
| CA2923385C (en) | 2013-09-27 | 2023-04-04 | Basf Se | Polyolefin compositions for building materials |
| TWI685524B (zh) | 2013-12-17 | 2020-02-21 | 美商畢克美國股份有限公司 | 預先脫層之層狀材料 |
| WO2016156328A1 (en) | 2015-03-31 | 2016-10-06 | Shell Internationale Research Maatschappij B.V. | Use of a lubricating composition comprising a hindered amine light stabilizer for improved piston cleanliness in an internal combustion engine |
| US9752093B2 (en) * | 2015-06-04 | 2017-09-05 | Chevron Oronite Company Llc | Borated polyol ester of hindered phenol antioxidant/friction modifier with enhanced performance |
| KR102580043B1 (ko) | 2015-07-20 | 2023-09-20 | 바스프 에스이 | 난연성 폴리올레핀 물품 |
| EP3263560A1 (en) | 2016-06-29 | 2018-01-03 | Borealis Agrolinz Melamine GmbH | Novel triazine-precondensate-aldehyde condensation products and method for obtaining the same |
| EP3263561A1 (en) | 2016-06-29 | 2018-01-03 | Borealis Agrolinz Melamine GmbH | Novel triazine precondensate and method for obtaining the same |
| CN109804008B (zh) | 2016-08-26 | 2021-03-12 | 道达尔研究技术弗吕公司 | 由包括聚乙烯的树脂组合物制成的帽或封闭件 |
| WO2020041181A1 (en) | 2018-08-22 | 2020-02-27 | Basf Se | Stabilized rotomolded polyolefin |
| EP3935052A1 (en) * | 2019-03-08 | 2022-01-12 | Basf Se | Sterically hindered amine stabilizer mixtures |
| WO2020190833A1 (en) | 2019-03-18 | 2020-09-24 | Basf Se | Uv curable compositions for dirt pick-up resistance |
| US20220282064A1 (en) | 2019-07-30 | 2022-09-08 | Basf Se | Stabilizer composition |
| CN117157355A (zh) | 2021-04-13 | 2023-12-01 | 道达尔能源一技术比利时公司 | 生产包含消费后树脂的聚乙烯的添加组合物的工艺以及由该组合物制成的帽或封闭件 |
| PL4321569T3 (pl) | 2022-08-12 | 2025-08-18 | Carl Freudenberg Kg | Ognioodporne usieciowane poliketony alifatyczne |
| US20240059867A1 (en) | 2022-08-12 | 2024-02-22 | Carl Freudenberg Kg | Flame-retardant molded articles for electrical devices |
| CN115611863B (zh) * | 2022-10-14 | 2023-11-14 | 天津大学浙江绍兴研究院 | 一种多功能三嗪基室温磷光材料及制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2642374A1 (de) * | 1976-09-21 | 1978-03-23 | Bayer Ag | Permanent stabilisierte polyurethane |
| DE2642386A1 (de) * | 1976-09-21 | 1978-03-23 | Bayer Ag | Permanent stabilisierte polyurethane |
| DE2862332D1 (en) * | 1977-12-30 | 1983-11-10 | Ciba Geigy Ag | Stabilisation of heat-curable metallic enamel paints against the action of light, humidity and oxygen by the addition of polyalkylpiperidine derivatives |
| DE2862264D1 (en) * | 1977-12-30 | 1983-07-07 | Ciba Geigy Ag | New polyalkylpiperidine derivatives of s-triazines, their use in the stabilisation of plastics and plastics stabilized in this way |
| DE2963604D1 (en) * | 1978-06-21 | 1982-10-28 | Ciba Geigy Ag | Light stabilization of acid catalysed stoving enamels |
| JPS58152881A (ja) * | 1982-03-08 | 1983-09-10 | Adeka Argus Chem Co Ltd | ビス（２−ヒドロキシエチル）アミノトリアジン化合物 |
| US4590231A (en) * | 1983-10-11 | 1986-05-20 | Ciba-Geigy Corporation | Polyolefin compositions stabilized against degradation using hydroxylamine derivatives |
| US4619956A (en) * | 1985-05-03 | 1986-10-28 | American Cyanamid Co. | Stabilization of high solids coatings with synergistic combinations |
| JPS6218444A (ja) * | 1985-07-16 | 1987-01-27 | Adeka Argus Chem Co Ltd | 安定化された高分子材料組成物 |
| JPS6218443A (ja) * | 1985-07-17 | 1987-01-27 | Adeka Argus Chem Co Ltd | 安定化高分子材料組成物 |
| FR2587340B1 (fr) * | 1985-09-13 | 1990-04-20 | Sandoz Sa | Nouvelles tetraalkylpiperidines, leur preparation et leur utilisation comme stabilisants des matieres polymeres |
| DE3888065T2 (de) * | 1987-09-21 | 1994-07-14 | Ciba-Geigy Ag, Basel | N-Acyloxy-substituierte sterisch gehinderte Aminstabilisatoren. |
| US5112890A (en) * | 1987-09-21 | 1992-05-12 | Ciba-Geigy Corporation | Stabilization of acid catalyzed thermoset resins |
| ES2065924T5 (es) * | 1987-09-21 | 2002-12-16 | Ciba Sc Holding Ag | Estabilizadores a base de amidas bloqueadas n-substituidas. |
| US5096950A (en) * | 1988-10-19 | 1992-03-17 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with NOR-substituted hindered amines |
| EP0365481A1 (en) * | 1988-10-19 | 1990-04-25 | Ciba-Geigy Ag | Polymeric substrates stabilized with N-substituted hindered amines |
| US5145893A (en) * | 1989-03-21 | 1992-09-08 | Ciba-Geigy Corporation | Non-migrating 1-hydrocarbyloxy hindered amine derivatives as polymer stabilizers |
| EP0389428A3 (en) * | 1989-03-21 | 1991-10-09 | Ciba-Geigy Ag | N,n-bis(l-hydroxycarbyloxy-2,2,6,6-tetramethyl-piperidin-4-yl) amino triazines and stabilized compositions |
| DE69008406T2 (de) * | 1989-03-21 | 1994-08-25 | Ciba Geigy Ag | N-Hydroxycarbyloxy-Derivate von s-Triazinen mit gehinderter Aminogruppe. |
| US5019613A (en) * | 1989-03-21 | 1991-05-28 | Ciba-Geigy Corporation | N-hydrocarbyloxy derivatives of hindered amine-substituted S-triazines |
| DE69026747T2 (de) * | 1989-03-21 | 1996-11-14 | Ciba Geigy Ag | Nichtwandernde 1-Hydrocarbyloxy-gehinderte Amineverbindungen als Polymerstabilisatoren |
| IT1230091B (it) * | 1989-04-27 | 1991-10-05 | Ciba Geigy Spa | Composti piperidin-triazinici atti all'impiego come stabilizzanti per materiali organici. |
| DE3919691A1 (de) * | 1989-06-16 | 1990-12-20 | Hoechst Ag | Polymere polyalkyl-1-oxa-diazaspirodecane |
| US5214084A (en) * | 1990-03-14 | 1993-05-25 | Sumitomo Chemical Company, Ltd. | Stabilized polypropylene resin composition |
| US5359703A (en) * | 1990-08-02 | 1994-10-25 | Xerox Corporation | Moving an object in a three-dimensional workspace |
-
1992
- 1992-05-05 US US07/878,678 patent/US5216156A/en not_active Expired - Lifetime
-
1993
- 1993-03-12 US US02/030,999 patent/US5300544A/en not_active Expired - Lifetime
- 1993-04-29 BE BE9300432A patent/BE1007753A3/fr not_active IP Right Cessation
- 1993-04-30 GB GB9308964A patent/GB2266717B/en not_active Expired - Lifetime
- 1993-05-03 IT ITMI930870A patent/IT1271467B/it active IP Right Grant
- 1993-05-03 AT AT0085893A patent/AT406162B/de not_active IP Right Cessation
- 1993-05-03 MX MX9302590A patent/MX9302590A/es unknown
- 1993-05-03 CA CA002095415A patent/CA2095415C/en not_active Expired - Lifetime
- 1993-05-04 FR FR9305276A patent/FR2690920B1/fr not_active Expired - Lifetime
- 1993-05-04 DE DE4314721A patent/DE4314721B4/de not_active Expired - Lifetime
- 1993-05-04 BR BR9301745A patent/BR9301745A/pt not_active IP Right Cessation
- 1993-05-04 KR KR1019930007784A patent/KR100253765B1/ko not_active Expired - Lifetime
- 1993-05-04 ES ES09300939A patent/ES2060548B1/es not_active Expired - Fee Related
- 1993-05-04 NL NL9300751A patent/NL195036C/nl not_active IP Right Cessation
- 1993-05-05 SE SE9301539A patent/SE505317C2/sv unknown
- 1993-05-06 JP JP12996293A patent/JP3259200B2/ja not_active Expired - Lifetime
- 1993-05-07 TW TW082103572A patent/TW237451B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2690920B1 (fr) | 1994-12-30 |
| ITMI930870A1 (it) | 1994-11-03 |
| IT1271467B (it) | 1997-05-28 |
| ATA85893A (de) | 1999-07-15 |
| JPH069582A (ja) | 1994-01-18 |
| NL9300751A (nl) | 1993-12-01 |
| SE9301539L (sv) | 1993-11-06 |
| SE505317C2 (sv) | 1997-08-04 |
| GB2266717A (en) | 1993-11-10 |
| SE9301539D0 (sv) | 1993-05-05 |
| BE1007753A3 (fr) | 1995-10-17 |
| CA2095415A1 (en) | 1993-11-06 |
| TW237451B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-01-01 |
| KR930023339A (ko) | 1993-12-18 |
| ES2060548B1 (es) | 1997-12-01 |
| GB2266717B (en) | 1996-07-24 |
| MX9302590A (es) | 1993-11-01 |
| KR100253765B1 (ko) | 2000-09-01 |
| GB9308964D0 (en) | 1993-06-16 |
| DE4314721B4 (de) | 2006-02-02 |
| FR2690920A1 (fr) | 1993-11-12 |
| ITMI930870A0 (it) | 1993-05-03 |
| US5216156A (en) | 1993-06-01 |
| CA2095415C (en) | 2004-08-10 |
| US5300544A (en) | 1994-04-05 |
| ES2060548A1 (es) | 1994-11-16 |
| BR9301745A (pt) | 1993-11-09 |
| DE4314721A1 (de) | 1993-11-11 |
| JP3259200B2 (ja) | 2002-02-25 |
| AT406162B (de) | 2000-03-27 |
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Free format text: CIBA SC HOLDING AG |
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| DNT | Communications of changes of names of applicants whose applications have been laid open to public inspection |
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