DE3505250A1 - Aliphatisch ungesaettigte bis(polybromphenyl)diamide - Google Patents
Aliphatisch ungesaettigte bis(polybromphenyl)diamideInfo
- Publication number
- DE3505250A1 DE3505250A1 DE19853505250 DE3505250A DE3505250A1 DE 3505250 A1 DE3505250 A1 DE 3505250A1 DE 19853505250 DE19853505250 DE 19853505250 DE 3505250 A DE3505250 A DE 3505250A DE 3505250 A1 DE3505250 A1 DE 3505250A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- trans
- bis
- diyl group
- diyl
- 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.)
- Granted
Links
- 150000001470 diamides Chemical class 0.000 title description 7
- 229920000642 polymer Polymers 0.000 claims abstract description 44
- -1 1,3-butadiene-1,4-diyl group Chemical group 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000003063 flame retardant Substances 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 44
- IJUNKLAVMFKPCX-OWOJBTEDSA-N (e)-n,n'-bis(2,4,6-tribromophenyl)but-2-enediamide Chemical compound BrC1=CC(Br)=CC(Br)=C1NC(=O)\C=C\C(=O)NC1=C(Br)C=C(Br)C=C1Br IJUNKLAVMFKPCX-OWOJBTEDSA-N 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- UWTUEMKLYAGTNQ-OWOJBTEDSA-N (e)-1,2-dibromoethene Chemical group Br\C=C\Br UWTUEMKLYAGTNQ-OWOJBTEDSA-N 0.000 claims description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 38
- 239000000654 additive Substances 0.000 description 30
- 230000000996 additive effect Effects 0.000 description 27
- 239000000047 product Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 229920001903 high density polyethylene Polymers 0.000 description 11
- 239000004700 high-density polyethylene Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 230000004580 weight loss Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- 239000003365 glass fiber Substances 0.000 description 6
- ZLYYJUJDFKGVKB-OWOJBTEDSA-N (e)-but-2-enedioyl dichloride Chemical compound ClC(=O)\C=C\C(Cl)=O ZLYYJUJDFKGVKB-OWOJBTEDSA-N 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
- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010561 standard procedure Methods 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000010304 firing Methods 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 229920005669 high impact polystyrene Polymers 0.000 description 3
- 239000004797 high-impact polystyrene Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
- PDERGHFHIOCEML-UHFFFAOYSA-N 5-chloro-4-oxopentanoyl chloride Chemical compound ClCC(=O)CCC(Cl)=O PDERGHFHIOCEML-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000005485 electric heating Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester 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
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- WLBUACIFTBBBAW-ZPUQHVIOSA-N (2e,4e)-hexa-2,4-dienedioyl dichloride Chemical compound ClC(=O)\C=C\C=C\C(Cl)=O WLBUACIFTBBBAW-ZPUQHVIOSA-N 0.000 description 1
- QHYNHZKMXIYZSL-OWOJBTEDSA-N (E)-pent-2-enedioyl dichloride Chemical compound C(\C=C\CC(=O)Cl)(=O)Cl QHYNHZKMXIYZSL-OWOJBTEDSA-N 0.000 description 1
- HSWCYBAOSLIGJO-OWOJBTEDSA-N (e)-hex-3-enedioyl dichloride Chemical compound ClC(=O)C\C=C\CC(Cl)=O HSWCYBAOSLIGJO-OWOJBTEDSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- BGESVUAXFYXTLZ-MQQKCMAXSA-N 1,3,5-tribromo-2-[(2E,4E)-hexa-2,4-dienyl]benzene Chemical compound BrC1=C(C(=CC(=C1)Br)Br)C\C=C\C=C\C BGESVUAXFYXTLZ-MQQKCMAXSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- VPFMJGCHDCVATR-UHFFFAOYSA-N 2,3,4,5,6-pentabromoaniline Chemical compound NC1=C(Br)C(Br)=C(Br)C(Br)=C1Br VPFMJGCHDCVATR-UHFFFAOYSA-N 0.000 description 1
- ZRLODVWGYJSMCP-UHFFFAOYSA-N 2,3,4,5-tetrabromoaniline Chemical compound NC1=CC(Br)=C(Br)C(Br)=C1Br ZRLODVWGYJSMCP-UHFFFAOYSA-N 0.000 description 1
- TWMMWNOMJFONOA-UHFFFAOYSA-N 2,3,4,6-tetrabromoaniline Chemical compound NC1=C(Br)C=C(Br)C(Br)=C1Br TWMMWNOMJFONOA-UHFFFAOYSA-N 0.000 description 1
- MDRUKDLYOLTXBU-UHFFFAOYSA-N 2,3,4-tribromoaniline Chemical compound NC1=CC=C(Br)C(Br)=C1Br MDRUKDLYOLTXBU-UHFFFAOYSA-N 0.000 description 1
- HWFWICXQCPRXNY-UHFFFAOYSA-N 2,3,5,6-tetrabromoaniline Chemical compound NC1=C(Br)C(Br)=CC(Br)=C1Br HWFWICXQCPRXNY-UHFFFAOYSA-N 0.000 description 1
- BRFIPEIKLLLCJW-UHFFFAOYSA-N 2,3,5-tribromoaniline Chemical compound NC1=CC(Br)=CC(Br)=C1Br BRFIPEIKLLLCJW-UHFFFAOYSA-N 0.000 description 1
- IANBJQQTAKDKDC-UHFFFAOYSA-N 2,4,5-tribromoaniline Chemical compound NC1=CC(Br)=C(Br)C=C1Br IANBJQQTAKDKDC-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
- FJBYYZKYMWMKRT-UHFFFAOYSA-N 3,4,5-tribromoaniline Chemical compound NC1=CC(Br)=C(Br)C(Br)=C1 FJBYYZKYMWMKRT-UHFFFAOYSA-N 0.000 description 1
- IMIMOZJZVIDJRG-HNQUOIGGSA-N C(\C=C\CCC(=O)Cl)(=O)Cl Chemical compound C(\C=C\CCC(=O)Cl)(=O)Cl IMIMOZJZVIDJRG-HNQUOIGGSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 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
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000011787 zinc oxide 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
- C08K5/20—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58147884A | 1984-02-17 | 1984-02-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3505250A1 true DE3505250A1 (de) | 1985-09-12 |
| DE3505250C2 DE3505250C2 (enrdf_load_html_response) | 1988-12-29 |
Family
ID=24325363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853505250 Granted DE3505250A1 (de) | 1984-02-17 | 1985-02-15 | Aliphatisch ungesaettigte bis(polybromphenyl)diamide |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE3505250A1 (enrdf_load_html_response) |
| IL (1) | IL74249A (enrdf_load_html_response) |
| NL (1) | NL8500249A (enrdf_load_html_response) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0642509A4 (en) * | 1991-10-04 | 1995-01-31 | Sloan Kettering Inst Cancer | NEW POTENTIAL INDUCTORS OF TERMINAL DIFFERENTIATION AND METHODS OF USE. |
| USRE38506E1 (en) | 1991-10-04 | 2004-04-20 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and methods of use thereof |
-
1985
- 1985-01-30 NL NL8500249A patent/NL8500249A/nl not_active Application Discontinuation
- 1985-02-05 IL IL74249A patent/IL74249A/xx unknown
- 1985-02-15 DE DE19853505250 patent/DE3505250A1/de active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0642509A4 (en) * | 1991-10-04 | 1995-01-31 | Sloan Kettering Inst Cancer | NEW POTENTIAL INDUCTORS OF TERMINAL DIFFERENTIATION AND METHODS OF USE. |
| US6087367A (en) * | 1991-10-04 | 2000-07-11 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and methods of use thereof |
| USRE38506E1 (en) | 1991-10-04 | 2004-04-20 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| IL74249A0 (en) | 1985-05-31 |
| NL8500249A (nl) | 1985-09-16 |
| DE3505250C2 (enrdf_load_html_response) | 1988-12-29 |
| IL74249A (en) | 1988-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2622414C2 (de) | Polybutylenterephthalatabmischungen mit hoher Schlagzähigkeit und ihre Verwendung | |
| DE2515473B2 (de) | Flaminwidrige, lineare Polyester | |
| DE2647699A1 (de) | N-substituierte tetrahalogenphthalimide, verfahren zu ihrer herstellung und ihre verwendung als feuerhemmende mittel | |
| EP1436344B1 (de) | Thermoplastische formmassen mit verbesserter schmelzestabilität auf basis von polyarylenethersulfonen | |
| EP1276816A1 (de) | Polyarylethersulfon/polyamid-blends mit verbesserter zähigkeit und fliessfähigkeit | |
| DE2612312A1 (de) | Formmassen aus mischungen halogenhaltiger und halogenfreier, polyfunktioneller, aromatischer cyansaeureester | |
| DE2433189C3 (de) | Schwer entflammbare, glasfaserverstärkte Polytetramethylenterephthalatformmasse | |
| DE2417663A1 (de) | Flammhemmende thermoplastische zusammensetzungen | |
| EP0613916A1 (de) | Formmasse auf der Grundlage von Polyarylenethern mit Anhydridendgruppen | |
| DE2837378C3 (de) | Flammwidrige Formmassen | |
| DE3505250C2 (enrdf_load_html_response) | ||
| EP0545309B1 (de) | Mischungen aus flüssigkristallinen Copolymeren, Polyetherimiden und Verträglichkeitsvermittlern sowie deren Verwendung | |
| DE4200931A1 (de) | Flammgeschuetzte thermoplastische polyesterformmasse und ihre verwendung | |
| EP0025018B1 (de) | Flammwidrige Kunststofformmasse | |
| EP0466002B1 (de) | Stabilisierte Polyaryletherketon-Formmassen | |
| DE3887231T2 (de) | Trisubstituierte s-Triazine, ihre Herstellung und ihre Verwendung. | |
| US4546139A (en) | Polybromo dinaphthyl ethers | |
| DE69103296T2 (de) | Flammenhemmende Verbindungen und sie enthaltende Zusammensetzungen. | |
| DE2028037A1 (enrdf_load_html_response) | ||
| DE3300180A1 (de) | Polyhalogenphthalimidoalkyl-verbindungen | |
| EP0545308A2 (de) | Mischungen aus flüssigkristallinen Copolymeren und Fluorthermoplasten sowie deren Verwendung | |
| DE2733564A1 (de) | 1,3,6-tris(4,6-diamino-1,3,5-triazin- 2-yl)hexan und diese verbindung enthaltende harzmassen | |
| EP0414124B1 (de) | Mehrkomponentenlegierung mit einer Glastemperatur | |
| EP0571398B1 (de) | Ternäre polymerlegierungen auf basis von polyaryletherketonen mit einer glastemperatur | |
| DE2642513A1 (de) | Flammwidrige polyesterharzmassen und verfahren zu ihrer herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |