JPS6360742B2 - - Google Patents
Info
- Publication number
- JPS6360742B2 JPS6360742B2 JP56022330A JP2233081A JPS6360742B2 JP S6360742 B2 JPS6360742 B2 JP S6360742B2 JP 56022330 A JP56022330 A JP 56022330A JP 2233081 A JP2233081 A JP 2233081A JP S6360742 B2 JPS6360742 B2 JP S6360742B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclic imide
- tetramethyl
- substituted
- formula
- cyclic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 cyclic imide Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229920000098 polyolefin Polymers 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 2
- 238000006303 photolysis reaction Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 229910052760 oxygen Inorganic materials 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 13
- 238000009835 boiling Methods 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 8
- 238000004364 calculation method Methods 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
- 238000005698 Diels-Alder reaction Methods 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000013065 commercial product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 2
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- KKZZSTCINUMTGD-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidin-4-ol Chemical compound CC1C(O)CCN(C)C1(C)C KKZZSTCINUMTGD-UHFFFAOYSA-N 0.000 description 1
- ZWAPXGVAJHESST-UHFFFAOYSA-N 1,2,3-trimethylcyclohexa-1,3-diene Chemical compound CC1=C(C)C(C)=CCC1 ZWAPXGVAJHESST-UHFFFAOYSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- OXAUHFISPWLGBV-UHFFFAOYSA-N 2-(2,2,6,6-tetramethylpiperidin-4-yl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1C(C)(C)NC(C)(C)CC1N1C(=O)C2CCCCC2C1=O OXAUHFISPWLGBV-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- FBIXXCXCZOZFCO-UHFFFAOYSA-N 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 FBIXXCXCZOZFCO-UHFFFAOYSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- ZCLZEKRMZKLVOX-UHFFFAOYSA-N 3-hexadecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 ZCLZEKRMZKLVOX-UHFFFAOYSA-N 0.000 description 1
- ATOPDRFFSGZPSM-UHFFFAOYSA-N 3-octadecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 ATOPDRFFSGZPSM-UHFFFAOYSA-N 0.000 description 1
- PUNCKRPTQOMTAO-UHFFFAOYSA-N 4-methyl-2-(2,2,6,6-tetramethylpiperidin-4-yl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound CC1CCCC(C2=O)C1C(=O)N2C1CC(C)(C)NC(C)(C)C1 PUNCKRPTQOMTAO-UHFFFAOYSA-N 0.000 description 1
- WWHKCKYSXZTSEP-UHFFFAOYSA-N 5-methyl-2-(2,2,6,6-tetramethylpiperidin-4-yl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1C(C)CCC(C2=O)C1C(=O)N2C1CC(C)(C)NC(C)(C)C1 WWHKCKYSXZTSEP-UHFFFAOYSA-N 0.000 description 1
- RFDDAWIOAAZBTG-UHFFFAOYSA-N 5-methyl-2-(2,2,6,6-tetramethylpiperidin-4-yl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1=CC(C)CC(C2=O)C1C(=O)N2C1CC(C)(C)NC(C)(C)C1 RFDDAWIOAAZBTG-UHFFFAOYSA-N 0.000 description 1
- 241000220450 Cajanus cajan Species 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- DHZBEENLJMYSHQ-XCVPVQRUSA-N cantharidin Chemical compound C([C@@H]1O2)C[C@@H]2[C@]2(C)[C@@]1(C)C(=O)OC2=O DHZBEENLJMYSHQ-XCVPVQRUSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803006272 DE3006272A1 (de) | 1980-02-20 | 1980-02-20 | Cyclische imide, deren herstellung und verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56131567A JPS56131567A (en) | 1981-10-15 |
| JPS6360742B2 true JPS6360742B2 (OSRAM) | 1988-11-25 |
Family
ID=6095053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2233081A Granted JPS56131567A (en) | 1980-02-20 | 1981-02-19 | Cyclic imide, its manufacture and its use |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4356307A (OSRAM) |
| EP (1) | EP0034805B1 (OSRAM) |
| JP (1) | JPS56131567A (OSRAM) |
| DE (2) | DE3006272A1 (OSRAM) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4520171A (en) * | 1982-05-05 | 1985-05-28 | Hercules Incorporated | Polymeric hindered amines |
| US4472547A (en) * | 1983-06-30 | 1984-09-18 | Ciba-Geigy Corporation | N-Piperidyl lactam light stabilizers |
| US4547537A (en) * | 1984-08-02 | 1985-10-15 | Ciba-Geigy Corporation | N-Piperidyl tetrahydro-1,4-oxazin-2-one light stabilizers |
| US4778837A (en) * | 1985-05-03 | 1988-10-18 | American Cyanamid Company | Low basicity hindered amine light stabilizers |
| US4619956A (en) * | 1985-05-03 | 1986-10-28 | American Cyanamid Co. | Stabilization of high solids coatings with synergistic combinations |
| US4743657A (en) * | 1986-03-17 | 1988-05-10 | Milliken Research Corporation | Method for preparing polymer bound stabilizers made from non-homopolymerizable stabilizers |
| JPS62253657A (ja) * | 1986-04-28 | 1987-11-05 | Adeka Argus Chem Co Ltd | 安定化された高分子材料組成物 |
| US5241067A (en) * | 1987-06-12 | 1993-08-31 | Elf Atochem North America, Inc. | Piperidinyl phthalimide hindered amine light stabilizers |
| US4824884A (en) * | 1987-08-12 | 1989-04-25 | Pennwalt Corporation | Cyclic anhydride derivatives of hydrazide functionalized hindered amine light stabilizers |
| US4874803A (en) * | 1987-09-21 | 1989-10-17 | Pennwalt Corporation | Dianhydride coupled polymer stabilizers |
| US4798836A (en) * | 1987-10-26 | 1989-01-17 | Adeka Argus Chemical Co., Ltd. | Bis-(2,2,6,6-tetramethyl-piperidyl) diimides as light stabilizers for synthetic polymers |
| DE69125095T2 (de) * | 1990-10-29 | 1997-08-21 | Cytec Tech Corp | Hydroxyaryltriazine und Tetraalkylpiperidine enthaltende synergistische UV-Absorbermischung |
| IT1247977B (it) * | 1991-06-04 | 1995-01-05 | Ciba Geigy Spa | Stabilizzazione di materiali organici polimerici mediante l`impiego dimiscele sinergiche costituite da ammine cicliche stericamente impeditee derivati del 3-pirazolidinone o del 1,2,4,-triazolidin-3,5,-dione |
| TW358820B (en) | 1995-04-11 | 1999-05-21 | Ciba Sc Holding Ag | Synergistic stabilizer mixture |
| TW390897B (en) * | 1995-07-21 | 2000-05-21 | Ciba Sc Holding Ag | Synergistic stabilizer mixture |
| US5618909A (en) * | 1995-07-27 | 1997-04-08 | Alliedsignal Inc. | Light stabilized polyamide substrate and process for making |
| TW467931B (en) * | 1996-08-22 | 2001-12-11 | Ciba Sc Holding Ag | Stabilizer mixtures |
| GB2354245B (en) * | 1996-08-22 | 2001-04-25 | Ciba Sc Holding Ag | Stabilizer mixtures for polyolefins |
| US6946517B2 (en) * | 1999-08-17 | 2005-09-20 | Ciba Specialty Chemicals Corporation | Stabilizer mixtures |
| CN1235958C (zh) * | 2000-05-31 | 2006-01-11 | 西巴特殊化学品控股有限公司 | 稳定剂混合物 |
| KR20030036930A (ko) * | 2000-10-16 | 2003-05-09 | 시바 스페셜티 케미칼스 홀딩 인크. | 분말 피막용 안정제 |
| US6545156B1 (en) | 2000-11-03 | 2003-04-08 | Cytec Technology Corp. | Oligomeric hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same |
| US6492521B2 (en) | 2000-11-03 | 2002-12-10 | Cytec Technology Corp. | Hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same |
| US6727300B2 (en) | 2000-11-03 | 2004-04-27 | Cytec Technology Corp. | Polymeric articles containing hindered amine light stabilizers based on multi-functional carbonyl compounds |
| US6414155B1 (en) | 2000-11-03 | 2002-07-02 | Cytec Technology Corp. | Oligomeric hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same |
| US20030225191A1 (en) | 2002-04-12 | 2003-12-04 | Francois Gugumus | Stabilizer mixtures |
| JP2005528497A (ja) * | 2002-05-30 | 2005-09-22 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 安定化された物品 |
| US20030236325A1 (en) * | 2002-05-30 | 2003-12-25 | Michela Bonora | Agricultural articles |
| GB0508350D0 (en) * | 2005-04-26 | 2005-06-01 | Great Lakes Chemical Europ | Stabilized crosslinked polyolefin compositions |
| JP2009502852A (ja) * | 2005-07-25 | 2009-01-29 | ビーエーエスエフ ソシエタス・ヨーロピア | 皮膚化粧品調製物 |
| US7968623B2 (en) * | 2007-08-06 | 2011-06-28 | General Cable Technologies Corp. | Tree resistant insulation compositions |
| CN102702169B (zh) * | 2012-06-19 | 2013-10-16 | 南通惠康国际企业有限公司 | 光稳定剂3-十二烷基-1-(1,2,2,6,6-五甲基哌啶基)-吡咯-2,5-二烷酮的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3684765A (en) * | 1970-01-08 | 1972-08-15 | Sankyo Co | Stabilization of synthetic polymers |
| US4053615A (en) * | 1972-10-21 | 1977-10-11 | John Wyeth & Brother Limited | Phthalimidopiperidines and anti-convulsant compositions thereof |
| DE2963604D1 (en) * | 1978-06-21 | 1982-10-28 | Ciba Geigy Ag | Light stabilization of acid catalysed stoving enamels |
| IT1097753B (it) * | 1978-07-28 | 1985-08-31 | Chimosa Chimica Organica Spa | Compcsti piperidinici, processo per la loro preparazione e loro impiego come stabil izzanti per polimeri sintetici |
-
1980
- 1980-02-20 DE DE19803006272 patent/DE3006272A1/de not_active Withdrawn
-
1981
- 1981-02-17 US US06/234,609 patent/US4356307A/en not_active Expired - Lifetime
- 1981-02-19 JP JP2233081A patent/JPS56131567A/ja active Granted
- 1981-02-19 DE DE8181101172T patent/DE3163035D1/de not_active Expired
- 1981-02-19 EP EP81101172A patent/EP0034805B1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56131567A (en) | 1981-10-15 |
| DE3006272A1 (de) | 1981-08-27 |
| EP0034805B1 (de) | 1984-04-11 |
| EP0034805A1 (de) | 1981-09-02 |
| US4356307A (en) | 1982-10-26 |
| DE3163035D1 (en) | 1984-05-17 |
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