JP2006520426A5 - - Google Patents
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- Publication number
- JP2006520426A5 JP2006520426A5 JP2006509021A JP2006509021A JP2006520426A5 JP 2006520426 A5 JP2006520426 A5 JP 2006520426A5 JP 2006509021 A JP2006509021 A JP 2006509021A JP 2006509021 A JP2006509021 A JP 2006509021A JP 2006520426 A5 JP2006520426 A5 JP 2006520426A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- cycloalkyl
- group
- light stabilizer
- 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.)
- Pending
Links
- 150000001412 amines Chemical class 0.000 claims description 34
- 239000004611 light stabiliser Substances 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims 65
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 48
- 150000003839 salts Chemical class 0.000 claims 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 239000001257 hydrogen Substances 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 30
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 28
- 229910052698 phosphorus Inorganic materials 0.000 claims 28
- 239000011574 phosphorus Substances 0.000 claims 28
- 150000002431 hydrogen Chemical class 0.000 claims 27
- 230000002378 acidificating effect Effects 0.000 claims 26
- 239000002798 polar solvent Substances 0.000 claims 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 24
- 239000002904 solvent Substances 0.000 claims 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 18
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 17
- 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 claims 14
- 125000004437 phosphorous atom Chemical group 0.000 claims 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 12
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 10
- 125000000732 arylene group Chemical group 0.000 claims 10
- 239000012454 non-polar solvent Substances 0.000 claims 10
- 125000001931 aliphatic group Chemical group 0.000 claims 9
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- SGVUHPSBDNVHKL-UHFFFAOYSA-N 1,3-dimethylcyclohexane Chemical compound CC1CCCC(C)C1 SGVUHPSBDNVHKL-UHFFFAOYSA-N 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 6
- 229920000728 polyester Polymers 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 4
- 150000002009 diols Chemical group 0.000 claims 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 4
- 125000005647 linker group Chemical group 0.000 claims 4
- 150000002894 organic compounds Chemical class 0.000 claims 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 4
- 239000008096 xylene Substances 0.000 claims 4
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 claims 3
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 3
- 239000002244 precipitate Substances 0.000 claims 3
- 239000011877 solvent mixture Substances 0.000 claims 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 239000012455 biphasic mixture Substances 0.000 claims 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical group OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical group OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical group OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000012456 homogeneous solution Substances 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 229920000515 polycarbonate Polymers 0.000 claims 1
- 239000004417 polycarbonate Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 238000001694 spray drying Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 CN(C(CC1*)=O)C1=O Chemical compound CN(C(CC1*)=O)C1=O 0.000 description 6
- 239000000126 substance Substances 0.000 description 4
- OWXXKGVQBCBSFJ-UHFFFAOYSA-N 6-n-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[2-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]ami Chemical compound N=1C(NCCCN(CCN(CCCNC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC(N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 OWXXKGVQBCBSFJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000463 material Substances 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45226303P | 2003-03-05 | 2003-03-05 | |
| US10/392,575 US20040183053A1 (en) | 2003-03-20 | 2003-03-20 | Process for the preparation of a hindered amine light stabilizer salt |
| PCT/US2004/006436 WO2004078837A1 (en) | 2003-03-05 | 2004-03-03 | Process for the preparation of a hindered amine light stabilizer salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006520426A JP2006520426A (ja) | 2006-09-07 |
| JP2006520426A5 true JP2006520426A5 (enExample) | 2006-10-19 |
Family
ID=32965333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006509021A Pending JP2006520426A (ja) | 2003-03-05 | 2004-03-03 | ヒンダードアミン光安定剤塩の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1599536B1 (enExample) |
| JP (1) | JP2006520426A (enExample) |
| KR (1) | KR20050115891A (enExample) |
| AT (1) | ATE354614T1 (enExample) |
| BR (1) | BRPI0407971A (enExample) |
| DE (1) | DE602004004876T8 (enExample) |
| WO (1) | WO2004078837A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070238814A1 (en) * | 2006-04-10 | 2007-10-11 | Basf Corporation | Method of making coating compositions |
| EP4194513A4 (en) * | 2020-08-07 | 2024-08-28 | Kuraray Co., Ltd. | COMPOSITION, RESIN COMPOSITION AND MOLDED BODY COMPRISING SAME |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0411660A (ja) * | 1990-04-27 | 1992-01-16 | Kyodo Yakuhin Kk | 合成樹脂組成物 |
| JPH0459852A (ja) * | 1990-06-29 | 1992-02-26 | Kyodo Yakuhin Kk | 塩化ビニル系樹脂組成物 |
| ES2099721T3 (es) * | 1990-10-29 | 1997-06-01 | Cytec Tech Corp | Composiciones sinergicas absorbentes de radiacion ultravioleta que contienen hidroxi aril triazinas y tetraalquil piperidinas. |
| US5441997A (en) * | 1992-12-22 | 1995-08-15 | General Electric Company | High density polyester-polycarbonate molding composition |
| EP0675159A1 (en) * | 1994-03-29 | 1995-10-04 | General Electric Company | Ultraviolet light stabilized polymer compositions |
| JPH10298439A (ja) * | 1997-04-28 | 1998-11-10 | Sakai Chem Ind Co Ltd | 樹脂用安定剤及びその利用 |
| US6635698B2 (en) * | 2000-12-22 | 2003-10-21 | General Electric Company | Flame retardant polycarbonate polyester composition |
-
2004
- 2004-03-03 EP EP04716925A patent/EP1599536B1/en not_active Expired - Lifetime
- 2004-03-03 KR KR1020057016487A patent/KR20050115891A/ko not_active Ceased
- 2004-03-03 WO PCT/US2004/006436 patent/WO2004078837A1/en not_active Ceased
- 2004-03-03 BR BRPI0407971-0A patent/BRPI0407971A/pt not_active IP Right Cessation
- 2004-03-03 DE DE602004004876T patent/DE602004004876T8/de active Active
- 2004-03-03 JP JP2006509021A patent/JP2006520426A/ja active Pending
- 2004-03-03 AT AT04716925T patent/ATE354614T1/de not_active IP Right Cessation
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