IL109251A - Bromine-converted diphenylalcane products, processes for their preparation and anti-flame formulation containing them - Google Patents

Bromine-converted diphenylalcane products, processes for their preparation and anti-flame formulation containing them

Info

Publication number: IL109251A
Authority: IL; Israel
Prior art keywords: product; brominated; diphenylalkane; brominated diphenylalkane; flame retardant
Prior art date: 1993-04-07

Application number

IL10925194A

Other languages

English (en)

Hebrew (he)

Other versions

IL109251A0 (en

Original Assignee

Great Lakes Chemical Corp

Priority date (The priority date 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 date listed.)

1993-04-07

Filing date

1994-04-07

Publication date

1999-05-09

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=21931414&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL109251(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1994-04-07 Application filed by Great Lakes Chemical Corp filed Critical Great Lakes Chemical Corp

1994-07-31 Publication of IL109251A0 publication Critical patent/IL109251A0/xx

1999-05-09 Publication of IL109251A publication Critical patent/IL109251A/en

Links

239000003063 flame retardant Substances 0.000 title claims description 58
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 title claims description 44
239000000203 mixture Substances 0.000 title claims description 42
238000000034 method Methods 0.000 title claims description 36
230000008569 process Effects 0.000 title claims description 29
238000009472 formulation Methods 0.000 title claims description 26
238000002360 preparation method Methods 0.000 title description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 75
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 74
229910052794 bromium Inorganic materials 0.000 claims description 74
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 55
238000005893 bromination reaction Methods 0.000 claims description 45
230000031709 bromination Effects 0.000 claims description 39
239000003054 catalyst Substances 0.000 claims description 36
239000007787 solid Substances 0.000 claims description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
BZQKBFHEWDPQHD-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenyl)ethyl]benzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1CCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br BZQKBFHEWDPQHD-UHFFFAOYSA-N 0.000 claims description 23
239000006185 dispersion Substances 0.000 claims description 23
239000000463 material Substances 0.000 claims description 23
239000003849 aromatic solvent Substances 0.000 claims description 21
229910052742 iron Inorganic materials 0.000 claims description 21
229920000642 polymer Polymers 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 16
-1 particulate Substances 0.000 claims description 16
239000002002 slurry Substances 0.000 claims description 15
BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical group C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 claims description 11
238000002844 melting Methods 0.000 claims description 11
230000008018 melting Effects 0.000 claims description 11
230000001070 adhesive effect Effects 0.000 claims description 9
239000004816 latex Substances 0.000 claims description 9
239000000853 adhesive Substances 0.000 claims description 8
229920000126 latex Polymers 0.000 claims description 8
238000009835 boiling Methods 0.000 claims description 7
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 7
238000000354 decomposition reaction Methods 0.000 claims description 6
238000004090 dissolution Methods 0.000 claims description 6
238000001035 drying Methods 0.000 claims description 6
239000000080 wetting agent Substances 0.000 claims description 6
239000008199 coating composition Substances 0.000 claims description 5
238000001816 cooling Methods 0.000 claims description 5
230000001747 exhibiting effect Effects 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
230000000979 retarding effect Effects 0.000 claims description 4
239000000839 emulsion Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910021576 Iron(III) bromide Inorganic materials 0.000 claims description 2
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims 1
239000000047 product Substances 0.000 description 92
238000006243 chemical reaction Methods 0.000 description 27
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 26
239000002904 solvent Substances 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
238000004458 analytical method Methods 0.000 description 16
238000000576 coating method Methods 0.000 description 16
238000011282 treatment Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000010992 reflux Methods 0.000 description 14
239000000243 solution Substances 0.000 description 14
229910052782 aluminium Inorganic materials 0.000 description 12
238000005260 corrosion Methods 0.000 description 11
238000002411 thermogravimetry Methods 0.000 description 11
IFPMZBBHBZQTOV-UHFFFAOYSA-N 1,3,5-trinitro-2-(2,4,6-trinitrophenyl)-4-[2,4,6-trinitro-3-(2,4,6-trinitrophenyl)phenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C=2C(=C(C=3C(=CC(=CC=3[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)C(=CC=2[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O IFPMZBBHBZQTOV-UHFFFAOYSA-N 0.000 description 10
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
239000011248 coating agent Substances 0.000 description 10
230000007797 corrosion Effects 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
239000000758 substrate Substances 0.000 description 10
239000004411 aluminium Substances 0.000 description 9
239000002245 particle Substances 0.000 description 8
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229920001577 copolymer Polymers 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000004744 fabric Substances 0.000 description 6
239000000376 reactant Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
239000011347 resin Substances 0.000 description 6
238000013019 agitation Methods 0.000 description 5
229910000410 antimony oxide Inorganic materials 0.000 description 5
125000001246 bromo group Chemical class Br* 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229920005669 high impact polystyrene Polymers 0.000 description 5
239000004797 high-impact polystyrene Substances 0.000 description 5
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 5
239000002562 thickening agent Substances 0.000 description 5
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 4
AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
229910000831 Steel Inorganic materials 0.000 description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
239000000178 monomer Substances 0.000 description 4
229920000728 polyester Polymers 0.000 description 4
238000012545 processing Methods 0.000 description 4
238000011084 recovery Methods 0.000 description 4
239000000176 sodium gluconate Substances 0.000 description 4
229940005574 sodium gluconate Drugs 0.000 description 4
235000012207 sodium gluconate Nutrition 0.000 description 4
239000010959 steel Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000004753 textile Substances 0.000 description 4
229920001169 thermoplastic Polymers 0.000 description 4
239000004416 thermosoftening plastic Substances 0.000 description 4
230000004584 weight gain Effects 0.000 description 4
235000019786 weight gain Nutrition 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 description 3
230000008901 benefit Effects 0.000 description 3
235000010290 biphenyl Nutrition 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
239000002738 chelating agent Substances 0.000 description 3
239000008139 complexing agent Substances 0.000 description 3
238000013329 compounding Methods 0.000 description 3
WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
229920001155 polypropylene Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
239000004677 Nylon Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229920006397 acrylic thermoplastic Polymers 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
229910052785 arsenic Inorganic materials 0.000 description 2
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
229910052797 bismuth Inorganic materials 0.000 description 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
238000001514 detection method Methods 0.000 description 2
230000029087 digestion Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
229910021478 group 5 element Inorganic materials 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000002484 inorganic compounds Chemical class 0.000 description 2
239000012796 inorganic flame retardant Substances 0.000 description 2
229910010272 inorganic material Inorganic materials 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
238000000465 moulding Methods 0.000 description 2
229920001778 nylon Polymers 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 2
239000000049 pigment Substances 0.000 description 2
239000004014 plasticizer Substances 0.000 description 2
229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000344 soap Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
238000012360 testing method Methods 0.000 description 2
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 2
238000005406 washing Methods 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
SSSBYZTYRWXPNJ-UHFFFAOYSA-N 10-phenyldecylbenzene Chemical compound C=1C=CC=CC=1CCCCCCCCCCC1=CC=CC=C1 SSSBYZTYRWXPNJ-UHFFFAOYSA-N 0.000 description 1
SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 1
ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 2,8-bis(diphenylphosphoryl)dibenzothiophene Chemical compound C=1C=CC=CC=1P(C=1C=C2C3=CC(=CC=C3SC2=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ZCJJIQHVZCFSGZ-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
GLJFYGFBITUZOE-UHFFFAOYSA-N 4-phenylbutylbenzene Chemical compound C=1C=CC=CC=1CCCCC1=CC=CC=C1 GLJFYGFBITUZOE-UHFFFAOYSA-N 0.000 description 1
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 1
AZZHCIXSZZXEAS-UHFFFAOYSA-N 5-phenylpentylbenzene Chemical compound C=1C=CC=CC=1CCCCCC1=CC=CC=C1 AZZHCIXSZZXEAS-UHFFFAOYSA-N 0.000 description 1
DVGPMIRVCZNXMD-UHFFFAOYSA-N 6-phenylhexylbenzene Chemical compound C=1C=CC=CC=1CCCCCCC1=CC=CC=C1 DVGPMIRVCZNXMD-UHFFFAOYSA-N 0.000 description 1
GQJMIKVSYWHDMK-UHFFFAOYSA-N 7-phenylheptylbenzene Chemical compound C=1C=CC=CC=1CCCCCCCC1=CC=CC=C1 GQJMIKVSYWHDMK-UHFFFAOYSA-N 0.000 description 1
PVBAGVQDXYRYAO-UHFFFAOYSA-N 8-phenyloctylbenzene Chemical compound C=1C=CC=CC=1CCCCCCCCC1=CC=CC=C1 PVBAGVQDXYRYAO-UHFFFAOYSA-N 0.000 description 1
WXQQXUQJVUAIDQ-UHFFFAOYSA-N 9-phenylnonylbenzene Chemical compound C=1C=CC=CC=1CCCCCCCCCC1=CC=CC=C1 WXQQXUQJVUAIDQ-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
229910000975 Carbon steel Inorganic materials 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
101100381997 Danio rerio tbc1d32 gene Proteins 0.000 description 1
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238000005773 Enders reaction Methods 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229910001209 Low-carbon steel Inorganic materials 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
101100381999 Mus musculus Tbc1d32 gene Proteins 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
150000004074 biphenyls Chemical class 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
229950005228 bromoform Drugs 0.000 description 1
229920005549 butyl rubber Polymers 0.000 description 1
239000010962 carbon steel Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
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230000008859 change Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical class C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000004519 grease Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000011551 heat transfer agent Substances 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000009972 noncorrosive effect Effects 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
239000004745 nonwoven fabric Substances 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic 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
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000004321 preservation Methods 0.000 description 1
238000011027 product recovery Methods 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000005086 pumping Methods 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000005070 sampling Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000565 sealant Substances 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
241000894007 species Species 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000004758 synthetic textile Substances 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
238000012546 transfer Methods 0.000 description 1
UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/392—Separation; Purification; Stabilisation; Use of additives by crystallisation; Purification or separation of the crystals
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Analytical Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Fireproofing Substances (AREA)
Compositions Of Macromolecular Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

IL10925194A 1993-04-07 1994-04-07 Bromine-converted diphenylalcane products, processes for their preparation and anti-flame formulation containing them IL109251A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4426693A	1993-04-07	1993-04-07

Publications (2)

Publication Number	Publication Date
IL109251A0 IL109251A0 (en)	1994-07-31
IL109251A true IL109251A (en)	1999-05-09

Family

ID=21931414

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10925194A IL109251A (en)	1993-04-07	1994-04-07	Bromine-converted diphenylalcane products, processes for their preparation and anti-flame formulation containing them

Country Status (9)

Country	Link
US (1)	US5457248A (fr)
EP (1)	EP0693100B1 (fr)
JP (1)	JPH08510208A (fr)
KR (1)	KR960701969A (fr)
AU (1)	AU6498594A (fr)
DE (1)	DE69413217T2 (fr)
IL (1)	IL109251A (fr)
TW (1)	TW343212B (fr)
WO (1)	WO1994022978A1 (fr)

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1994
- 1994-04-07 JP JP6522496A patent/JPH08510208A/ja active Pending
- 1994-04-07 EP EP94912399A patent/EP0693100B1/fr not_active Expired - Lifetime
- 1994-04-07 DE DE69413217T patent/DE69413217T2/de not_active Expired - Fee Related
- 1994-04-07 IL IL10925194A patent/IL109251A/en not_active IP Right Cessation
- 1994-04-07 AU AU64985/94A patent/AU6498594A/en not_active Abandoned
- 1994-04-07 KR KR1019950704380A patent/KR960701969A/ko not_active Ceased
- 1994-04-07 US US08/224,345 patent/US5457248A/en not_active Expired - Lifetime
- 1994-04-07 WO PCT/US1994/003841 patent/WO1994022978A1/fr not_active Ceased
- 1994-06-14 TW TW083105356A patent/TW343212B/zh active

Also Published As

Publication number	Publication date
WO1994022978A1 (fr)	1994-10-13
EP0693100A1 (fr)	1996-01-24
IL109251A0 (en)	1994-07-31
DE69413217D1 (de)	1998-10-15
KR960701969A (ko)	1996-03-28
EP0693100A4 (fr)	1996-04-24
US5457248A (en)	1995-10-10
EP0693100B1 (fr)	1998-09-09
HK1009977A1 (en)	1999-06-11
JPH08510208A (ja)	1996-10-29
AU6498594A (en)	1994-10-24
DE69413217T2 (de)	1999-02-18
TW343212B (en)	1998-10-21

Legal Events

Date	Code	Title
2002-02-10	NP	Permission for amending the patent specification granted (section 66, patents law 1967)
2003-11-23	KB	Patent renewed
2004-06-01	KB	Patent renewed
2008-06-05	KB	Patent renewed
2012-11-29	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0693100B1 (fr)	1998-09-09	Produits a base de diphenylalcane bromine et procedes associes
EP0784648B1 (fr)	2006-06-21	Procede de bromuration en continu et produits resultants
US6117371A (en)	2000-09-12	Continuous bromination process and products thereof
CA2047256C (fr)	2002-03-05	Methode pour obtenir un produit predominant dans le decabromodiphenylalcane
KR100219894B1 (ko)	1999-09-01	데카브로모디페닐 알칸 생성물 및 그의 제조방법
KR101536032B1 (ko)	2015-07-10	저분자량의 브롬화 중합체, 이들의 제조 방법 및 열가소성 배합물에서 이들의 용도
US6008283A (en)	1999-12-28	Oligomeric flame retardant additive
EP0047549A2 (fr)	1982-03-17	Procédé de bromination de polystyrènes
CA2094470C (fr)	2005-09-27	Produit renfermant surtout du decabromodiphenylethane, a blancheur amelioree
US5077334A (en)	1991-12-31	Flame-retarded formulations of thermoplastics and decabromodiphenylethane
US5124496A (en)	1992-06-23	Process for decabromodiphenylalkane predominant product
EP0335953A4 (fr)	1990-02-20	Procede de production d'alkylbenzenes superieurs polybromes.
HK1009977B (en)	2000-04-20	Brominated diphenylalkane products and processes
EP2137253B1 (fr)	2016-08-03	Désactivateur/inhibiteur de métaux lourds utilisés dans des polymères oléfiniques
JP3004113B2 (ja)	2000-01-31	デカブロモジフエニルアルカン方法
Gibbs et al.	1914	CLXXV.—Experiments on the migration of para-halogen atoms in phenols