DE3300180C2 - - Google Patents
Info
- Publication number
- DE3300180C2 DE3300180C2 DE3300180A DE3300180A DE3300180C2 DE 3300180 C2 DE3300180 C2 DE 3300180C2 DE 3300180 A DE3300180 A DE 3300180A DE 3300180 A DE3300180 A DE 3300180A DE 3300180 C2 DE3300180 C2 DE 3300180C2
- Authority
- DE
- Germany
- Prior art keywords
- carbonate
- ethyl
- reaction mixture
- deposition
- bromine
- 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 2- (tetrabromophthalimido) ethyl pentabromphenyl carbonate Chemical compound 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 83
- 229910052794 bromium Inorganic materials 0.000 claims description 70
- 239000000460 chlorine Substances 0.000 claims description 51
- 229910052801 chlorine Inorganic materials 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 47
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 46
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 45
- 229920000642 polymer Polymers 0.000 claims description 34
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 28
- 239000003063 flame retardant Substances 0.000 claims description 28
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- YGKZJNQEGZOVFH-UHFFFAOYSA-N (2,4,6-tribromo-3-ethylphenyl) hydrogen carbonate Chemical compound CCC1=C(C(=C(C=C1Br)Br)OC(=O)O)Br YGKZJNQEGZOVFH-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000007787 solid Substances 0.000 description 96
- 239000011541 reaction mixture Substances 0.000 description 94
- 230000008021 deposition Effects 0.000 description 68
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 238000000926 separation method Methods 0.000 description 50
- 239000000243 solution Substances 0.000 description 39
- 238000010992 reflux Methods 0.000 description 35
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
- 239000000047 product Substances 0.000 description 32
- 238000012360 testing method Methods 0.000 description 32
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- 238000004811 liquid chromatography Methods 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- 239000000654 additive Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 20
- 238000001914 filtration Methods 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- ZEEJBQJAPCTECM-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C(Br)C2=C1C(=O)N(CCO)C2=O ZEEJBQJAPCTECM-UHFFFAOYSA-N 0.000 description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 14
- 230000000996 additive effect Effects 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000004793 Polystyrene Substances 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 150000008064 anhydrides Chemical class 0.000 description 11
- QXGQDWRMEVHRAK-UHFFFAOYSA-N bis[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl] carbonate Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCOC(=O)OCCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O QXGQDWRMEVHRAK-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 10
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 230000004580 weight loss Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004566 IR spectroscopy Methods 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 238000002411 thermogravimetry Methods 0.000 description 9
- QLMQRJJLWGQDDG-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) carbonochloridate Chemical compound ClC(=O)OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br QLMQRJJLWGQDDG-UHFFFAOYSA-N 0.000 description 8
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000001569 carbon dioxide Substances 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical group 0.000 description 8
- 239000004700 high-density polyethylene Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001414 amino alcohols Chemical class 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229920001903 high density polyethylene Polymers 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- JPZLJAXIOWPRJM-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-(5-hydroxypentyl)isoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(=O)N(CCCCCO)C2=O JPZLJAXIOWPRJM-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- UBIWRHNFEDLHSD-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) 2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl carbonate Chemical compound O=C1C2=C(Br)C(Br)=C(Br)C(Br)=C2C(=O)N1CCOC(=O)OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br UBIWRHNFEDLHSD-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 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 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FUAWLDKQVCRQPB-UHFFFAOYSA-N 2,4-dibromo-3,5,6-trichlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Br)C(Cl)=C1Br FUAWLDKQVCRQPB-UHFFFAOYSA-N 0.000 description 4
- QRFTXHFUNIFHST-UHFFFAOYSA-N 4,5,6,7-tetrabromoisoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C2C(=O)NC(=O)C2=C1Br QRFTXHFUNIFHST-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000005485 electric heating Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229940004975 interceptor Drugs 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- AOSAVHRILYUBSN-UHFFFAOYSA-N 4,5,6-tribromo-2-(2-chloroethyl)isoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C2C(=O)N(CCCl)C(=O)C2=C1 AOSAVHRILYUBSN-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- NRKAYFNNPYXBLP-UHFFFAOYSA-N bis[5-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)pentyl] carbonate Chemical compound O=C1C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C(=O)N1CCCCCOC(=O)OCCCCCN1C(=O)C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2C1=O NRKAYFNNPYXBLP-UHFFFAOYSA-N 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 239000002516 radical scavenger Substances 0.000 description 3
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- BCPDKUOGJIICPL-UHFFFAOYSA-N (2,3,4,5,6-pentabromophenyl) 2-(4,5,6-tribromo-1,3-dioxoisoindol-2-yl)ethyl carbonate Chemical compound O=C1C=2C(Br)=C(Br)C(Br)=CC=2C(=O)N1CCOC(=O)OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br BCPDKUOGJIICPL-UHFFFAOYSA-N 0.000 description 2
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 2
- ZQEMULIECSQHJU-UHFFFAOYSA-N 2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl (2,4,6-tribromophenyl) carbonate Chemical compound BrC1=CC(Br)=CC(Br)=C1OC(=O)OCCN1C(=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C1=O ZQEMULIECSQHJU-UHFFFAOYSA-N 0.000 description 2
- YSXNORJDWJNWHV-UHFFFAOYSA-N 2-(4,5,6-tribromo-1,3-dioxoisoindol-2-yl)ethyl carbonochloridate Chemical compound BrC1=C(Br)C(Br)=C2C(=O)N(CCOC(=O)Cl)C(=O)C2=C1 YSXNORJDWJNWHV-UHFFFAOYSA-N 0.000 description 2
- WYLPYLHDMNVOQP-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-(5-chloropentyl)isoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C2=C1C(=O)N(CCCCCCl)C2=O WYLPYLHDMNVOQP-UHFFFAOYSA-N 0.000 description 2
- YSIJKYDFHNOFEN-UHFFFAOYSA-N 4,5,6-tribromo-2-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C2C(=O)N(CCO)C(=O)C2=C1 YSIJKYDFHNOFEN-UHFFFAOYSA-N 0.000 description 2
- KUSJVBWDLIVLIG-UHFFFAOYSA-N 4,5,6-tribromo-2-benzofuran-1,3-dione Chemical compound BrC1=C(Br)C(Br)=CC2=C1C(=O)OC2=O KUSJVBWDLIVLIG-UHFFFAOYSA-N 0.000 description 2
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YHDSTFKCTSIXKN-UHFFFAOYSA-N [bromo(chloro)-$l^{3}-chloranyl]formyl chloride Chemical compound ClCl(Br)C(Cl)=O YHDSTFKCTSIXKN-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 2
- 239000004703 cross-linked polyethylene Substances 0.000 description 2
- 229920003020 cross-linked polyethylene Polymers 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000933 poly (ε-caprolactam) Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- OVWUIIOIVQKPSE-UHFFFAOYSA-N 2,3,3-trichloroprop-2-enyl 4-(4-chloroanilino)-4-oxobutanoate Chemical compound ClC(Cl)=C(Cl)COC(=O)CCC(=O)NC1=CC=C(Cl)C=C1 OVWUIIOIVQKPSE-UHFFFAOYSA-N 0.000 description 1
- YBUYUFUUMVETOE-UHFFFAOYSA-N 2,3,4,5-tetrabromo-6-(2-hydroxyethylcarbamoyl)benzoic acid Chemical compound OCCNC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O YBUYUFUUMVETOE-UHFFFAOYSA-N 0.000 description 1
- IWCZSSJDSDXULX-UHFFFAOYSA-N 2,3,4-tribromo-6-[(3-hydroxy-2-methylpropyl)carbamoyl]benzoic acid Chemical compound OCC(C)CNC(=O)C1=CC(Br)=C(Br)C(Br)=C1C(O)=O IWCZSSJDSDXULX-UHFFFAOYSA-N 0.000 description 1
- WWGQHTJIFOQAOC-UHFFFAOYSA-N 2,3,5-trichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1Cl WWGQHTJIFOQAOC-UHFFFAOYSA-N 0.000 description 1
- SSCLLPHDHZJNPX-UHFFFAOYSA-N 2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl carbonochloridate Chemical compound BrC1=C(Br)C(Br)=C(Br)C2=C1C(=O)N(CCOC(=O)Cl)C2=O SSCLLPHDHZJNPX-UHFFFAOYSA-N 0.000 description 1
- NWYYWIJOWOLJNR-UHFFFAOYSA-N 2-Amino-3-methyl-1-butanol Chemical compound CC(C)C(N)CO NWYYWIJOWOLJNR-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- HFUMJHZNXZZWED-UHFFFAOYSA-N 2-bromo-3,5,6-trichlorophenol Chemical compound OC1=C(Cl)C(Cl)=CC(Cl)=C1Br HFUMJHZNXZZWED-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- RGUIGXFOHAOFLG-UHFFFAOYSA-N 2-n,3-n-dimethylpyridine-2,3-diamine Chemical compound CNC1=CC=CN=C1NC RGUIGXFOHAOFLG-UHFFFAOYSA-N 0.000 description 1
- SZNHBHMKJUPBPK-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-(2-chloroethyl)isoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C(Br)C2=C1C(=O)N(CCCl)C2=O SZNHBHMKJUPBPK-UHFFFAOYSA-N 0.000 description 1
- WSKSHHDHKIAMKX-UHFFFAOYSA-N 4,5,6-trichloro-2-benzofuran-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=CC2=C1C(=O)OC2=O WSKSHHDHKIAMKX-UHFFFAOYSA-N 0.000 description 1
- MQABZEKRHIDHBT-UHFFFAOYSA-N 4,5,7-tribromo-2-benzofuran-1,3-dione Chemical compound BrC1=CC(Br)=C(Br)C2=C1C(=O)OC2=O MQABZEKRHIDHBT-UHFFFAOYSA-N 0.000 description 1
- PAODPKLYMCJZEG-UHFFFAOYSA-N 4,5,7-trichloro-2-benzofuran-1,3-dione Chemical compound ClC1=CC(Cl)=C(Cl)C2=C1C(=O)OC2=O PAODPKLYMCJZEG-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- FWQYCZFMFPZQBN-UHFFFAOYSA-N 4-bromo-2,3,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Br)C(Cl)=C1Cl FWQYCZFMFPZQBN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- AZTQABZDEZOZIE-UHFFFAOYSA-N C(CCN1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl)CCOC(=O)O Chemical compound C(CCN1C(=O)C2=C(C1=O)C(=C(C(=C2Cl)Cl)Cl)Cl)CCOC(=O)O AZTQABZDEZOZIE-UHFFFAOYSA-N 0.000 description 1
- GPLCVJXZXXXJTP-UHFFFAOYSA-N CC(CN1C(=O)C2=C(C1=O)C(=C(C(=C2Br)Br)Br)Br)C3=C(C(=C(C=C3Br)Br)OC(=O)O)Br Chemical compound CC(CN1C(=O)C2=C(C1=O)C(=C(C(=C2Br)Br)Br)Br)C3=C(C(=C(C=C3Br)Br)OC(=O)O)Br GPLCVJXZXXXJTP-UHFFFAOYSA-N 0.000 description 1
- GRSHBJGUJKHZCQ-UHFFFAOYSA-N CC(CN1C(=O)C2=C(C1=O)C(=C(C=C2Br)Br)Br)C3(C(C(=C(C(=C3Br)Br)Br)Br)Br)OC(=O)O Chemical compound CC(CN1C(=O)C2=C(C1=O)C(=C(C=C2Br)Br)Br)C3(C(C(=C(C(=C3Br)Br)Br)Br)Br)OC(=O)O GRSHBJGUJKHZCQ-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- DCUFXXQKNYNUFH-UHFFFAOYSA-N OC(OC(CCN(C(C(C1=C(C(Br)=C2Br)Br)=C2Br)=O)C1=O)(C(C(Br)=C1Br)Br)C(Br)=C1Br)=O Chemical compound OC(OC(CCN(C(C(C1=C(C(Br)=C2Br)Br)=C2Br)=O)C1=O)(C(C(Br)=C1Br)Br)C(Br)=C1Br)=O DCUFXXQKNYNUFH-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- GLMRCTIBJCEHLX-UHFFFAOYSA-N bis(2,3,4,5,6-pentabromophenyl) carbonate Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC(=O)OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br GLMRCTIBJCEHLX-UHFFFAOYSA-N 0.000 description 1
- MFOGRZVJAHRYAG-UHFFFAOYSA-N bis[2-(4,5,6,7-tetrachloro-1,3-dioxoisoindol-2-yl)ethyl] carbonate Chemical compound O=C1C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C(=O)N1CCOC(=O)OCCN1C(=O)C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2C1=O MFOGRZVJAHRYAG-UHFFFAOYSA-N 0.000 description 1
- YIKOBJVLZDVBHR-UHFFFAOYSA-N bis[2-(4,5,6-tribromo-1,3-dioxoisoindol-2-yl)ethyl] carbonate Chemical compound O=C1C2=CC(Br)=C(Br)C(Br)=C2C(=O)N1CCOC(=O)OCCN1C(=O)C(C=C(C(=C2Br)Br)Br)=C2C1=O YIKOBJVLZDVBHR-UHFFFAOYSA-N 0.000 description 1
- JATJBJAWFHKRJD-UHFFFAOYSA-N bis[2-(4,5,7-tribromo-1,3-dioxoisoindol-2-yl)ethyl] carbonate Chemical compound O=C1C(C(=CC(Br)=C2Br)Br)=C2C(=O)N1CCOC(=O)OCCN1C(=O)C(C(Br)=C(Br)C=C2Br)=C2C1=O JATJBJAWFHKRJD-UHFFFAOYSA-N 0.000 description 1
- SJXKALAQTVDSQN-UHFFFAOYSA-N bis[2-(4,5,7-trichloro-1,3-dioxoisoindol-2-yl)ethyl] carbonate Chemical compound O=C1C(C(=CC(Cl)=C2Cl)Cl)=C2C(=O)N1CCOC(=O)OCCN1C(=O)C(C(Cl)=C(Cl)C=C2Cl)=C2C1=O SJXKALAQTVDSQN-UHFFFAOYSA-N 0.000 description 1
- LRJDXNIBNCZQBL-UHFFFAOYSA-N bis[3-(4,5,6-trichloro-1,3-dioxoisoindol-2-yl)propyl] carbonate Chemical compound O=C1C2=CC(Cl)=C(Cl)C(Cl)=C2C(=O)N1CCCOC(=O)OCCCN1C(=O)C(C=C(C(=C2Cl)Cl)Cl)=C2C1=O LRJDXNIBNCZQBL-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- XHRRYUDVWPPWIP-UHFFFAOYSA-N pentyl carbonochloridate Chemical compound CCCCCOC(Cl)=O XHRRYUDVWPPWIP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- C08K5/3415—Five-membered rings
- C08K5/3417—Five-membered rings condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Indole Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/337,660 US4414396A (en) | 1982-01-07 | 1982-01-07 | Polyhalophthalimidoalkyl-functional carbonates and haloformates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3300180A1 DE3300180A1 (de) | 1983-07-14 |
| DE3300180C2 true DE3300180C2 (OSRAM) | 1987-10-22 |
Family
ID=23321470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833300180 Granted DE3300180A1 (de) | 1982-01-07 | 1983-01-05 | Polyhalogenphthalimidoalkyl-verbindungen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4414396A (OSRAM) |
| JP (1) | JPS58126864A (OSRAM) |
| DE (1) | DE3300180A1 (OSRAM) |
| FR (1) | FR2519340B1 (OSRAM) |
| GB (1) | GB2114127B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666958A (en) * | 1982-01-07 | 1987-05-19 | Ppg Industries, Inc. | Polymeric compositions containing polyhalophthalimidoalkyl-functional carbonates |
| US4578409A (en) * | 1985-01-14 | 1986-03-25 | Mobay Chemical Corporation | Flame retarding silanes |
| US4753970A (en) * | 1986-04-21 | 1988-06-28 | Nippon Kasei Chemical Co., Ltd. | Fire-retardant polyolefin composition |
| US4999391A (en) * | 1988-03-25 | 1991-03-12 | Atochem North America, Inc. | Halogen substituted phthalimide flame retardants |
| US4904795A (en) * | 1988-03-25 | 1990-02-27 | Pennwalt Corporation | Halogen substituted phthalimide flame retardants |
| WO2012099847A2 (en) * | 2011-01-17 | 2012-07-26 | Isp Investments Inc. | Compounds, monomers, and polymers containing a carbonate linkage |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2451637A (en) * | 1947-02-01 | 1948-10-19 | Eastman Kodak Co | N(beta-hydroxy ethyl)-tetraiodophthalimide |
| US2657169A (en) * | 1950-10-28 | 1953-10-27 | Ethyl Corp | N-aminophthalic imides and salts thereof as fungicidal compositions |
| BE544762A (OSRAM) * | 1955-01-28 | |||
| US3240792A (en) * | 1961-03-22 | 1966-03-15 | Imp Smelting Corp Ltd | Tetrafluorophthalic acids and derivatives |
| FR1405916A (fr) * | 1963-05-27 | 1965-07-16 | Hooker Chemical Corp | Compositions polymères ignifuges et de propriétés thermiques améliorées |
| US3313763A (en) * | 1963-05-27 | 1967-04-11 | Hooker Chemical Corp | Fire retardant polymer compositions having improved thermal properties |
| US3251855A (en) * | 1964-02-17 | 1966-05-17 | Upjohn Co | Derivatives of phthalimide |
| DE1257778B (de) * | 1964-08-13 | 1968-01-04 | Huels Chemische Werke Ag | Verfahren zur Herstellung von N-2-Acyloxyaethyl-phthalimiden |
| US3873567A (en) * | 1968-09-05 | 1975-03-25 | Universal Oil Prod Co | N-substituted polybromoaromatic ortho-dicarboximides |
| US4581396A (en) | 1968-09-18 | 1986-04-08 | Raychem Corporation | Flame retardants and compositions containing them |
| CH515954A (de) * | 1968-10-17 | 1971-11-30 | Bayer Ag | Selbstverlöschende Polyamid-Formmasse |
| US3624024A (en) * | 1970-02-24 | 1971-11-30 | Eastman Kodak Co | Flame retardant poly(tetramethylene terephthalate) molding compositions |
| US3978079A (en) * | 1972-02-04 | 1976-08-31 | American Cyanamid Company | Chemiluminescence |
| US3868388A (en) * | 1972-10-20 | 1975-02-25 | Cities Service Co | Flame-retardant composition |
| US3847869A (en) * | 1973-09-28 | 1974-11-12 | Gen Electric | Method for preparing polyetherimides |
| US4003862A (en) * | 1975-10-23 | 1977-01-18 | Michigan Chemical Corporation | N-substituted tetrahalophthalimides as flame retardants |
| US4125535A (en) * | 1976-06-04 | 1978-11-14 | Cities Service Company | Process for preparing bisimides and bisimides prepared thereby |
| FR2369261A1 (fr) * | 1976-10-28 | 1978-05-26 | Dynamit Nobel Ag | Derives de tetrabromophtalimide et leur application a titre d'agents d'ignifugation |
| DE2656954A1 (de) * | 1976-12-16 | 1978-06-29 | Dynamit Nobel Ag | Esterimide und ihre verwendung als flammschutzmittel |
| US4140862A (en) * | 1977-01-17 | 1979-02-20 | Cities Service Company | Salts of diamines and tetrahalophthalates |
| US4197133A (en) * | 1977-10-14 | 1980-04-08 | Ciba-Geigy Corporation | Photo-curable compositions of matter containing bis-azidophthalimidyl derivatives |
| US4250096A (en) * | 1977-10-14 | 1981-02-10 | Ciba-Geigy Corporation | 3- and 4-Azidophthalic acid derivatives |
| US4263222A (en) * | 1980-02-22 | 1981-04-21 | General Electric Company | Dichloroformates |
-
1982
- 1982-01-07 US US06/337,660 patent/US4414396A/en not_active Expired - Fee Related
-
1983
- 1983-01-05 DE DE19833300180 patent/DE3300180A1/de active Granted
- 1983-01-06 GB GB08300207A patent/GB2114127B/en not_active Expired
- 1983-01-06 JP JP58000749A patent/JPS58126864A/ja active Granted
- 1983-01-06 FR FR8300159A patent/FR2519340B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6345668B2 (OSRAM) | 1988-09-12 |
| JPS58126864A (ja) | 1983-07-28 |
| GB2114127A (en) | 1983-08-17 |
| GB8300207D0 (en) | 1983-02-09 |
| DE3300180A1 (de) | 1983-07-14 |
| GB2114127B (en) | 1985-09-04 |
| FR2519340A1 (fr) | 1983-07-08 |
| FR2519340B1 (fr) | 1986-04-11 |
| US4414396A (en) | 1983-11-08 |
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