MXPA06005648A - Composiciones aditivas, retardantes de flama y poliuretanos retardantes de flama. - Google Patents
Composiciones aditivas, retardantes de flama y poliuretanos retardantes de flama.Info
- Publication number
- MXPA06005648A MXPA06005648A MXPA06005648A MXPA06005648A MXPA06005648A MX PA06005648 A MXPA06005648 A MX PA06005648A MX PA06005648 A MXPA06005648 A MX PA06005648A MX PA06005648 A MXPA06005648 A MX PA06005648A MX PA06005648 A MXPA06005648 A MX PA06005648A
- Authority
- MX
- Mexico
- Prior art keywords
- chlorophosphate
- consists essentially
- anhydride
- reaction product
- carbon atoms
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 127
- 239000003063 flame retardant Substances 0.000 title claims abstract description 62
- 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 abstract description 56
- 239000000654 additive Substances 0.000 title claims abstract description 21
- 230000000996 additive effect Effects 0.000 title claims abstract description 21
- 239000004814 polyurethane Substances 0.000 title description 7
- 229920002635 polyurethane Polymers 0.000 title description 4
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 64
- -1 brominated aromatic diester diol Chemical class 0.000 claims abstract description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 56
- 239000007788 liquid Substances 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 42
- 229920005830 Polyurethane Foam Polymers 0.000 claims abstract description 35
- 239000011496 polyurethane foam Substances 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 25
- 239000006260 foam Substances 0.000 claims abstract description 21
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 20
- 150000001412 amines Chemical class 0.000 claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002530 phenolic antioxidant Substances 0.000 claims abstract description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 126
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 123
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 48
- 150000002148 esters Chemical class 0.000 claims description 46
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 claims description 43
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 229910019142 PO4 Inorganic materials 0.000 claims description 32
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 31
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 31
- 229910052794 bromium Inorganic materials 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 239000004615 ingredient Substances 0.000 claims description 29
- 239000010452 phosphate Substances 0.000 claims description 28
- 150000008064 anhydrides Chemical class 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 27
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 27
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 claims description 26
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 24
- 238000009472 formulation Methods 0.000 claims description 21
- 229920005862 polyol Polymers 0.000 claims description 21
- 150000003077 polyols Chemical class 0.000 claims description 21
- 239000003153 chemical reaction reagent Substances 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- FANGQVKSFHFPBY-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FANGQVKSFHFPBY-UHFFFAOYSA-N 0.000 claims description 16
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical group C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 claims description 16
- 150000002924 oxiranes Chemical class 0.000 claims description 16
- 239000012948 isocyanate Substances 0.000 claims description 14
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 239000004604 Blowing Agent Substances 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 12
- 150000001266 acyl halides Chemical class 0.000 claims description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 claims description 4
- 238000005292 vacuum distillation Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000306 component Substances 0.000 description 46
- 235000021317 phosphate Nutrition 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000126 substance Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- FREZLSIGWNCSOQ-UHFFFAOYSA-N 3-methylbutanoyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(=O)CC(C)C FREZLSIGWNCSOQ-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002176 Pluracol® Polymers 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000000159 acid neutralizing agent Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YEYCMBWKTZNPDH-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)C1=CC=CC=C1 YEYCMBWKTZNPDH-UHFFFAOYSA-N 0.000 description 1
- RQHMQURGSQBBJY-UHFFFAOYSA-N (2,2-dichloroacetyl) 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC(=O)C(Cl)Cl RQHMQURGSQBBJY-UHFFFAOYSA-N 0.000 description 1
- FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 1
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- RBNSZWOCWHGHMR-UHFFFAOYSA-N (2-iodoacetyl) 2-iodoacetate Chemical compound ICC(=O)OC(=O)CI RBNSZWOCWHGHMR-UHFFFAOYSA-N 0.000 description 1
- ZHHCWQGVXYGWCW-UHFFFAOYSA-N 1,1,1-trichloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxyethane Chemical compound ClC(Cl)(Cl)COP(Cl)(=O)OCC(Cl)(Cl)Cl ZHHCWQGVXYGWCW-UHFFFAOYSA-N 0.000 description 1
- HPJCPSYPYUEEJE-UHFFFAOYSA-N 1,1,1-trichloro-4-[chloro(4,4,4-trichlorobutoxy)phosphoryl]oxybutane Chemical compound ClC(Cl)(Cl)CCCOP(Cl)(=O)OCCCC(Cl)(Cl)Cl HPJCPSYPYUEEJE-UHFFFAOYSA-N 0.000 description 1
- FOUJVQQBUJCOLS-UHFFFAOYSA-N 1,1-dibromo-3-[chloro(3,3-dibromopropoxy)phosphoryl]oxypropane Chemical compound BrC(Br)CCOP(=O)(Cl)OCCC(Br)Br FOUJVQQBUJCOLS-UHFFFAOYSA-N 0.000 description 1
- GVPRYQFXULLTPU-UHFFFAOYSA-N 1,1-dichloro-2-[chloro(2,2-dichloroethenoxy)phosphoryl]oxyethene Chemical compound ClC(Cl)=COP(Cl)(=O)OC=C(Cl)Cl GVPRYQFXULLTPU-UHFFFAOYSA-N 0.000 description 1
- HZWGSSYOAIWJJB-UHFFFAOYSA-N 1,2,3-tribromo-4-[chloro(2,3,4-tribromobutoxy)phosphoryl]oxybutane Chemical compound BrCC(Br)C(Br)COP(=O)(Cl)OCC(Br)C(Br)CBr HZWGSSYOAIWJJB-UHFFFAOYSA-N 0.000 description 1
- COWMHTOCXHIQHS-UHFFFAOYSA-N 1,2-dichloro-3-[chloro(2,3-dichloropropoxy)phosphoryl]oxypropane Chemical compound ClCC(Cl)COP(Cl)(=O)OCC(Cl)CCl COWMHTOCXHIQHS-UHFFFAOYSA-N 0.000 description 1
- AGQJYXFUQQGXSU-UHFFFAOYSA-N 1,4-dibromo-2-[chloro-(2,5-dibromophenoxy)phosphoryl]oxybenzene Chemical compound C=1C(Br)=CC=C(Br)C=1OP(=O)(Cl)OC1=CC(Br)=CC=C1Br AGQJYXFUQQGXSU-UHFFFAOYSA-N 0.000 description 1
- QZCLIGGLTKDZPQ-UHFFFAOYSA-N 1-[[3,5-bis(bromomethyl)phenoxy]-chlorophosphoryl]oxy-3,5-bis(bromomethyl)benzene Chemical compound C=1C(CBr)=CC(CBr)=CC=1OP(=O)(Cl)OC1=CC(CBr)=CC(CBr)=C1 QZCLIGGLTKDZPQ-UHFFFAOYSA-N 0.000 description 1
- IWGBOBUFRAEIJH-UHFFFAOYSA-N 1-[chloro(ethenoxy)phosphoryl]oxyethene Chemical compound C=COP(=O)(Cl)OC=C IWGBOBUFRAEIJH-UHFFFAOYSA-N 0.000 description 1
- BAAIJPNWVQTSPU-UHFFFAOYSA-N 1-[chloro(heptoxy)phosphoryl]oxyheptane Chemical compound CCCCCCCOP(Cl)(=O)OCCCCCCC BAAIJPNWVQTSPU-UHFFFAOYSA-N 0.000 description 1
- PIXASLFUIBPUPU-UHFFFAOYSA-N 1-[chloro(hexoxy)phosphoryl]oxyhexane Chemical compound CCCCCCOP(Cl)(=O)OCCCCCC PIXASLFUIBPUPU-UHFFFAOYSA-N 0.000 description 1
- QDMDEACVMQNHDO-UHFFFAOYSA-N 1-[chloro(nonoxy)phosphoryl]oxynonane Chemical compound CCCCCCCCCOP(Cl)(=O)OCCCCCCCCC QDMDEACVMQNHDO-UHFFFAOYSA-N 0.000 description 1
- MGWMBNBSQQGLAW-UHFFFAOYSA-N 1-[chloro(propoxy)phosphoryl]oxypropane Chemical compound CCCOP(Cl)(=O)OCCC MGWMBNBSQQGLAW-UHFFFAOYSA-N 0.000 description 1
- RKQCRIBSOCCBQJ-UHFFFAOYSA-N 1-[chloro-(2-methylphenoxy)phosphoryl]oxy-2-methylbenzene Chemical compound CC1=CC=CC=C1OP(Cl)(=O)OC1=CC=CC=C1C RKQCRIBSOCCBQJ-UHFFFAOYSA-N 0.000 description 1
- VYHGCXOQLBEEJN-UHFFFAOYSA-N 1-[chloro-(3,5-dimethylphenoxy)phosphoryl]oxy-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(OP(Cl)(=O)OC=2C=C(C)C=C(C)C=2)=C1 VYHGCXOQLBEEJN-UHFFFAOYSA-N 0.000 description 1
- BNDUYVNXBZYPMZ-UHFFFAOYSA-N 1-[chloro-(4-methylphenoxy)phosphoryl]oxy-4-methylbenzene Chemical compound C1=CC(C)=CC=C1OP(Cl)(=O)OC1=CC=C(C)C=C1 BNDUYVNXBZYPMZ-UHFFFAOYSA-N 0.000 description 1
- KYNLYVFUBUCGTG-UHFFFAOYSA-N 1-[chloro-(4-propan-2-ylphenoxy)phosphoryl]oxy-4-propan-2-ylbenzene Chemical compound C1=CC(C(C)C)=CC=C1OP(Cl)(=O)OC1=CC=C(C(C)C)C=C1 KYNLYVFUBUCGTG-UHFFFAOYSA-N 0.000 description 1
- AVZJCJNBKHVPDQ-UHFFFAOYSA-N 1-bromo-3-[3-bromopropoxy(chloro)phosphoryl]oxypropane Chemical compound BrCCCOP(=O)(Cl)OCCCBr AVZJCJNBKHVPDQ-UHFFFAOYSA-N 0.000 description 1
- ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
- XETKNKZXWYEULP-UHFFFAOYSA-N 1-chloro-2-[chloro(2-chloroethoxy)phosphoryl]oxyethane Chemical compound ClCCOP(Cl)(=O)OCCCl XETKNKZXWYEULP-UHFFFAOYSA-N 0.000 description 1
- PMGATFZDMDTJKE-UHFFFAOYSA-N 1-chloro-4-[chloro-(4-chlorophenoxy)phosphoryl]oxybenzene Chemical compound C1=CC(Cl)=CC=C1OP(Cl)(=O)OC1=CC=C(Cl)C=C1 PMGATFZDMDTJKE-UHFFFAOYSA-N 0.000 description 1
- AJCRRVGEPDVNLK-UHFFFAOYSA-N 1-chloro-8-[chloro-(8-chloronaphthalen-1-yl)oxyphosphoryl]oxynaphthalene Chemical compound C1=CC(Cl)=C2C(OP(Cl)(=O)OC=3C=CC=C4C=CC=C(C=34)Cl)=CC=CC2=C1 AJCRRVGEPDVNLK-UHFFFAOYSA-N 0.000 description 1
- QPBYBLZYMNWGMO-UHFFFAOYSA-N 2,2,3-trimethyloxirane Chemical compound CC1OC1(C)C QPBYBLZYMNWGMO-UHFFFAOYSA-N 0.000 description 1
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- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- RHQSBXZVIMBYKW-UHFFFAOYSA-N 2,4-dichloro-1-[chloro-(2,4-dichlorophenoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC(Cl)=CC=C1OP(Cl)(=O)OC1=CC=C(Cl)C=C1Cl RHQSBXZVIMBYKW-UHFFFAOYSA-N 0.000 description 1
- ZDXGQHXSMPGQRI-UHFFFAOYSA-N 2,6-ditert-butyl-3-[(2,4-ditert-butyl-3-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC=C1CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C ZDXGQHXSMPGQRI-UHFFFAOYSA-N 0.000 description 1
- QLMGIWHWWWXXME-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)acetic acid Chemical compound CC(C)(C)C1=CC(CC(O)=O)=CC(C(C)(C)C)=C1O QLMGIWHWWWXXME-UHFFFAOYSA-N 0.000 description 1
- WCBBNGGFTGRHNV-UHFFFAOYSA-N 2-(3-tert-butyl-4-hydroxy-5-methylphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC(C)=C(O)C(C(C)(C)C)=C1 WCBBNGGFTGRHNV-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- KWNRPFNOKIDPLN-UHFFFAOYSA-N 2-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoic acid Chemical compound CC(C)C1=CC(C(C)C(O)=O)=CC(C(C)C)=C1O KWNRPFNOKIDPLN-UHFFFAOYSA-N 0.000 description 1
- JJKKKEJWTMIBRQ-UHFFFAOYSA-N 2-[4-hydroxy-3-methyl-5-(2-methylbutan-2-yl)phenyl]hexanoic acid Chemical compound CCCCC(C(O)=O)C1=CC(C)=C(O)C(C(C)(C)CC)=C1 JJKKKEJWTMIBRQ-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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- UKYNESNNFCHAEV-UHFFFAOYSA-N 3,4-dibromooxolane-2,5-dione Chemical compound BrC1C(Br)C(=O)OC1=O UKYNESNNFCHAEV-UHFFFAOYSA-N 0.000 description 1
- AGULWIQIYWWFBJ-UHFFFAOYSA-N 3,4-dichlorofuran-2,5-dione Chemical compound ClC1=C(Cl)C(=O)OC1=O AGULWIQIYWWFBJ-UHFFFAOYSA-N 0.000 description 1
- HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-UHFFFAOYSA-N 0.000 description 1
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- IHBVNSPHKMCPST-UHFFFAOYSA-N 3-bromopropanoyl chloride Chemical compound ClC(=O)CCBr IHBVNSPHKMCPST-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
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- MELPJGOMEMRMPL-UHFFFAOYSA-N 9-oxabicyclo[6.1.0]nonane Chemical compound C1CCCCCC2OC21 MELPJGOMEMRMPL-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- JMFKQZQQTSIXFY-UHFFFAOYSA-N ClC(COP(OCC(Cl)Cl)(=O)Cl)Cl Chemical compound ClC(COP(OCC(Cl)Cl)(=O)Cl)Cl JMFKQZQQTSIXFY-UHFFFAOYSA-N 0.000 description 1
- QONUJRHZWGPJPC-UHFFFAOYSA-N ClCC(Cl)COP(=O)(O)OCC(Cl)CCl Chemical compound ClCC(Cl)COP(=O)(O)OCC(Cl)CCl QONUJRHZWGPJPC-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
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- 239000005977 Ethylene Substances 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- RFRQZJYGPMVWNO-UHFFFAOYSA-N [chloro(cyclopentyloxy)phosphoryl]oxycyclopentane Chemical compound C1CCCC1OP(=O)(Cl)OC1CCCC1 RFRQZJYGPMVWNO-UHFFFAOYSA-N 0.000 description 1
- SVNGYUMAOUOHCE-UHFFFAOYSA-N [chloro(cyclopropyloxy)phosphoryl]oxycyclopropane Chemical compound C1CC1OP(=O)(Cl)OC1CC1 SVNGYUMAOUOHCE-UHFFFAOYSA-N 0.000 description 1
- NGFFLHMFSINFGB-UHFFFAOYSA-N [chloro(methoxy)phosphoryl]oxymethane Chemical compound COP(Cl)(=O)OC NGFFLHMFSINFGB-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- SVYONMGCIOEHOO-UHFFFAOYSA-N bis(1,2-dibromoethyl) hydrogen phosphate Chemical compound BrCC(Br)OP(=O)(O)OC(Br)CBr SVYONMGCIOEHOO-UHFFFAOYSA-N 0.000 description 1
- MJNADLMYQJTRGW-UHFFFAOYSA-N bis(1,4-dibromonaphthalen-2-yl) hydrogen phosphate Chemical compound C1=CC=CC2=C(Br)C(OP(=O)(OC=3C(=C4C=CC=CC4=C(Br)C=3)Br)O)=CC(Br)=C21 MJNADLMYQJTRGW-UHFFFAOYSA-N 0.000 description 1
- CFRHVJAOAULIRG-UHFFFAOYSA-N bis(1-bromo-3-chloropropan-2-yl) hydrogen phosphate Chemical compound ClCC(CBr)OP(=O)(O)OC(CCl)CBr CFRHVJAOAULIRG-UHFFFAOYSA-N 0.000 description 1
- QZUZYRQEGHDUJR-UHFFFAOYSA-N bis(1-methylcyclohexyl) hydrogen phosphate Chemical compound C1CCCCC1(C)OP(O)(=O)OC1(C)CCCCC1 QZUZYRQEGHDUJR-UHFFFAOYSA-N 0.000 description 1
- ROLQPIOIXBZPFD-UHFFFAOYSA-N bis(2,2,2-trichloroethyl) hydrogen phosphate Chemical compound ClC(Cl)(Cl)COP(=O)(O)OCC(Cl)(Cl)Cl ROLQPIOIXBZPFD-UHFFFAOYSA-N 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
- WIPUEFWYSZFGLX-UHFFFAOYSA-N bis(2,2-dichlorocyclohexyl) hydrogen phosphate Chemical compound C1CCCC(Cl)(Cl)C1OP(=O)(O)OC1CCCCC1(Cl)Cl WIPUEFWYSZFGLX-UHFFFAOYSA-N 0.000 description 1
- FMYQTDSYXPAKKF-UHFFFAOYSA-N bis(2,4-dibromophenyl) hydrogen phosphate Chemical compound C=1C=C(Br)C=C(Br)C=1OP(=O)(O)OC1=CC=C(Br)C=C1Br FMYQTDSYXPAKKF-UHFFFAOYSA-N 0.000 description 1
- FAEDFEUORGJVOF-UHFFFAOYSA-N bis(2,5-dichlorophenyl) hydrogen phosphate Chemical compound C=1C(Cl)=CC=C(Cl)C=1OP(=O)(O)OC1=CC(Cl)=CC=C1Cl FAEDFEUORGJVOF-UHFFFAOYSA-N 0.000 description 1
- RNKDFEYVFWYXEK-UHFFFAOYSA-N bis(2,5-dimethylphenyl) hydrogen phosphate Chemical compound CC1=CC=C(C)C(OP(O)(=O)OC=2C(=CC=C(C)C=2)C)=C1 RNKDFEYVFWYXEK-UHFFFAOYSA-N 0.000 description 1
- RYUPAQFDLMRRET-UHFFFAOYSA-N bis(2-bromoethenoxy)-chloro-sulfanylidene-$l^{5}-phosphane Chemical compound BrC=COP(=S)(Cl)OC=CBr RYUPAQFDLMRRET-UHFFFAOYSA-N 0.000 description 1
- UUEFDGORLDWVJF-UHFFFAOYSA-N bis(2-bromoethenyl) hydrogen phosphate Chemical compound BrC=COP(=O)(O)OC=CBr UUEFDGORLDWVJF-UHFFFAOYSA-N 0.000 description 1
- IUVCKFXOOWHDOD-UHFFFAOYSA-N bis(2-bromophenoxy)-chloro-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=C(Br)C=1OP(=S)(Cl)OC1=CC=CC=C1Br IUVCKFXOOWHDOD-UHFFFAOYSA-N 0.000 description 1
- QDGIPGUZJVCWDY-UHFFFAOYSA-N bis(2-bromopropoxy)-chloro-sulfanylidene-$l^{5}-phosphane Chemical compound CC(Br)COP(Cl)(=S)OCC(C)Br QDGIPGUZJVCWDY-UHFFFAOYSA-N 0.000 description 1
- HCZIEWHRARORGB-UHFFFAOYSA-N bis(2-chloronaphthalen-1-yl) hydrogen phosphate Chemical compound C1=CC=C2C(OP(=O)(OC=3C4=CC=CC=C4C=CC=3Cl)O)=C(Cl)C=CC2=C1 HCZIEWHRARORGB-UHFFFAOYSA-N 0.000 description 1
- UZFHQOAXJYGYPN-UHFFFAOYSA-N bis(2-chloropentyl) hydrogen phosphate Chemical compound CCCC(Cl)COP(O)(=O)OCC(Cl)CCC UZFHQOAXJYGYPN-UHFFFAOYSA-N 0.000 description 1
- IOPCEPCSTBOTEG-UHFFFAOYSA-N bis(2-chlorophenyl) hydrogen phosphate Chemical compound C=1C=CC=C(Cl)C=1OP(=O)(O)OC1=CC=CC=C1Cl IOPCEPCSTBOTEG-UHFFFAOYSA-N 0.000 description 1
- OHRCKPRYDGSBRN-UHFFFAOYSA-N bis(2-methylphenyl) hydrogen phosphate Chemical compound CC1=CC=CC=C1OP(O)(=O)OC1=CC=CC=C1C OHRCKPRYDGSBRN-UHFFFAOYSA-N 0.000 description 1
- BEAFHPLLBXXUHK-UHFFFAOYSA-N bis(2-propan-2-ylphenyl) hydrogen phosphate Chemical compound CC(C)C1=CC=CC=C1OP(O)(=O)OC1=CC=CC=C1C(C)C BEAFHPLLBXXUHK-UHFFFAOYSA-N 0.000 description 1
- OSPGCGMHPWVBNN-UHFFFAOYSA-N bis(3-bromocyclopentyl) hydrogen phosphate Chemical compound C1CC(Br)CC1OP(=O)(O)OC1CCC(Br)C1 OSPGCGMHPWVBNN-UHFFFAOYSA-N 0.000 description 1
- NOZQQXUDZNLSEM-UHFFFAOYSA-N bis(3-bromopropyl) hydrogen phosphate Chemical compound BrCCCOP(=O)(O)OCCCBr NOZQQXUDZNLSEM-UHFFFAOYSA-N 0.000 description 1
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- NYGQJFIWPGPERC-UHFFFAOYSA-N bis(4,4,4-tribromobutyl) hydrogen phosphate Chemical compound BrC(Br)(Br)CCCOP(=O)(O)OCCCC(Br)(Br)Br NYGQJFIWPGPERC-UHFFFAOYSA-N 0.000 description 1
- QYBXCCDNYZHKQD-UHFFFAOYSA-N bis(bromomethoxy)-chloro-sulfanylidene-$l^{5}-phosphane Chemical compound BrCOP(=S)(Cl)OCBr QYBXCCDNYZHKQD-UHFFFAOYSA-N 0.000 description 1
- YGSJTHLHZSXRQO-UHFFFAOYSA-N bis(chloromethyl) hydrogen phosphate Chemical compound ClCOP(=O)(O)OCCl YGSJTHLHZSXRQO-UHFFFAOYSA-N 0.000 description 1
- WKMLEMCDOHPDCF-UHFFFAOYSA-N bis(dibromomethyl) hydrogen phosphate Chemical compound BrC(Br)OP(=O)(O)OC(Br)Br WKMLEMCDOHPDCF-UHFFFAOYSA-N 0.000 description 1
- PFWTWIIECBCANP-UHFFFAOYSA-N bis(ethenyl) hydrogen phosphate Chemical compound C=COP(=O)(O)OC=C PFWTWIIECBCANP-UHFFFAOYSA-N 0.000 description 1
- RMRGTONBWKAEEX-UHFFFAOYSA-N bis(pent-4-enyl) hydrogen phosphate Chemical compound C=CCCCOP(=O)(O)OCCCC=C RMRGTONBWKAEEX-UHFFFAOYSA-N 0.000 description 1
- RMFLFIKRMMPQDQ-UHFFFAOYSA-N bis(tribromomethyl) hydrogen phosphate Chemical compound BrC(Br)(Br)OP(=O)(O)OC(Br)(Br)Br RMFLFIKRMMPQDQ-UHFFFAOYSA-N 0.000 description 1
- MZASWNNFDGQBFT-UHFFFAOYSA-N bis(trichloromethyl) hydrogen phosphate Chemical compound ClC(Cl)(Cl)OP(=O)(O)OC(Cl)(Cl)Cl MZASWNNFDGQBFT-UHFFFAOYSA-N 0.000 description 1
- ZMJAMLYPKVCMJX-UHFFFAOYSA-N bis[(3-bromocyclopentyl)oxy]-chloro-sulfanylidene-$l^{5}-phosphane Chemical compound C1CC(Br)CC1OP(=S)(Cl)OC1CCC(Br)C1 ZMJAMLYPKVCMJX-UHFFFAOYSA-N 0.000 description 1
- QBPKAOWWNCQLEW-UHFFFAOYSA-N bis[2-(trichloromethyl)phenyl] hydrogen phosphate Chemical compound C=1C=CC=C(C(Cl)(Cl)Cl)C=1OP(=O)(O)OC1=CC=CC=C1C(Cl)(Cl)Cl QBPKAOWWNCQLEW-UHFFFAOYSA-N 0.000 description 1
- UFNJQOZNICXXFF-UHFFFAOYSA-N bis[3,5-bis(bromomethyl)phenyl] hydrogen phosphate Chemical compound C=1C(CBr)=CC(CBr)=CC=1OP(=O)(O)OC1=CC(CBr)=CC(CBr)=C1 UFNJQOZNICXXFF-UHFFFAOYSA-N 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 125000005340 bisphosphate group Chemical group 0.000 description 1
- JFUAPDIQFCBQEQ-UHFFFAOYSA-N bromo-[bromomethoxy(chloro)phosphoryl]oxymethane Chemical compound BrCOP(=O)(Cl)OCBr JFUAPDIQFCBQEQ-UHFFFAOYSA-N 0.000 description 1
- OKOSPWNNXVDXKZ-UHFFFAOYSA-N but-3-enoyl chloride Chemical compound ClC(=O)CC=C OKOSPWNNXVDXKZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
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- ZRSPTVIRKWIYOG-UHFFFAOYSA-N chloro-dipentoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCOP(Cl)(=S)OCCCCC ZRSPTVIRKWIYOG-UHFFFAOYSA-N 0.000 description 1
- XZNHGHRDZQVVQR-UHFFFAOYSA-N chloro-diphenoxy-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=S)(Cl)OC1=CC=CC=C1 XZNHGHRDZQVVQR-UHFFFAOYSA-N 0.000 description 1
- VZWIGIXJYOZQQJ-UHFFFAOYSA-N chloro-sulfanylidene-bis(2,2,2-trichloroethoxy)-$l^{5}-phosphane Chemical compound ClC(Cl)(Cl)COP(Cl)(=S)OCC(Cl)(Cl)Cl VZWIGIXJYOZQQJ-UHFFFAOYSA-N 0.000 description 1
- NSSJIFLJGSQOQC-UHFFFAOYSA-N chloro-sulfanylidene-bis(4,4,4-tribromobutoxy)-$l^{5}-phosphane Chemical compound BrC(Br)(Br)CCCOP(=S)(Cl)OCCCC(Br)(Br)Br NSSJIFLJGSQOQC-UHFFFAOYSA-N 0.000 description 1
- DLFMBNLZFSTQRS-UHFFFAOYSA-N chloro-sulfanylidene-bis(trichloromethoxy)-$l^{5}-phosphane Chemical compound ClC(Cl)(Cl)OP(Cl)(=S)OC(Cl)(Cl)Cl DLFMBNLZFSTQRS-UHFFFAOYSA-N 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-M dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)([O-])OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-M 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- SWXUEJURRAEAMJ-UHFFFAOYSA-N dicyclobutyl hydrogen phosphate Chemical compound C1CCC1OP(=O)(O)OC1CCC1 SWXUEJURRAEAMJ-UHFFFAOYSA-N 0.000 description 1
- POVJEPOYXLSCLY-UHFFFAOYSA-N dicyclopentyl hydrogen phosphate Chemical compound C1CCCC1OP(=O)(O)OC1CCCC1 POVJEPOYXLSCLY-UHFFFAOYSA-N 0.000 description 1
- PYGPMDXRQICOAP-UHFFFAOYSA-N dicyclopropyl hydrogen phosphate Chemical compound C1CC1OP(=O)(O)OC1CC1 PYGPMDXRQICOAP-UHFFFAOYSA-N 0.000 description 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- ITJPTURSPJESQC-UHFFFAOYSA-N diethyl pentyl phosphate Chemical compound CCCCCOP(=O)(OCC)OCC ITJPTURSPJESQC-UHFFFAOYSA-N 0.000 description 1
- WZPMZMCZAGFKOC-UHFFFAOYSA-N diisopropyl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC(C)C WZPMZMCZAGFKOC-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WJZUIWBZDGBLKK-UHFFFAOYSA-M dipentyl phosphate Chemical compound CCCCCOP([O-])(=O)OCCCCC WJZUIWBZDGBLKK-UHFFFAOYSA-M 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- YEWZQCDRZRYAEB-UHFFFAOYSA-M ditert-butyl phosphate Chemical compound CC(C)(C)OP([O-])(=O)OC(C)(C)C YEWZQCDRZRYAEB-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000004124 hock Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WRXFONORSZHETC-UHFFFAOYSA-N phenyl propan-2-yl hydrogen phosphate Chemical compound CC(C)OP(O)(=O)OC1=CC=CC=C1 WRXFONORSZHETC-UHFFFAOYSA-N 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- YIPZJTGXMJGCFV-UHFFFAOYSA-N tribromo-[chloro(tribromomethoxy)phosphoryl]oxymethane Chemical compound BrC(Br)(Br)OP(=O)(Cl)OC(Br)(Br)Br YIPZJTGXMJGCFV-UHFFFAOYSA-N 0.000 description 1
- SONASQDMXRVTFG-UHFFFAOYSA-N trichloro-[chloro(trichloromethoxy)phosphoryl]oxymethane Chemical compound ClC(Cl)(Cl)OP(Cl)(=O)OC(Cl)(Cl)Cl SONASQDMXRVTFG-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000004876 x-ray fluorescence Methods 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
-
- 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
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- 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
- 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
- C09K21/14—Macromolecular materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/719,948 US7153901B2 (en) | 2003-11-21 | 2003-11-21 | Flame retardant, additive compositions, and flame retardant polyurethanes |
| PCT/US2004/038071 WO2005052018A2 (en) | 2003-11-21 | 2004-11-16 | Flame retardant, additive compositions, and flame retardant polyurethanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06005648A true MXPA06005648A (es) | 2006-08-17 |
Family
ID=34591465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06005648A MXPA06005648A (es) | 2003-11-21 | 2004-11-16 | Composiciones aditivas, retardantes de flama y poliuretanos retardantes de flama. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7153901B2 (https=) |
| EP (1) | EP1685176A2 (https=) |
| JP (1) | JP2007513224A (https=) |
| KR (1) | KR20060123176A (https=) |
| CN (1) | CN1882629A (https=) |
| AU (1) | AU2004292526A1 (https=) |
| BR (1) | BRPI0417049A (https=) |
| CA (1) | CA2546299A1 (https=) |
| IL (1) | IL175687A0 (https=) |
| MX (1) | MXPA06005648A (https=) |
| RU (1) | RU2006121970A (https=) |
| UA (1) | UA84722C2 (https=) |
| WO (1) | WO2005052018A2 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1574995A1 (en) * | 2004-03-12 | 2005-09-14 | Thomson Licensing S.A. | Method for encoding interlaced digital video data |
| MX2008012835A (es) * | 2006-04-06 | 2008-10-17 | Albemarle Corp | Composiciones de aditivo retardante de flama y uso de las mismas. |
| JP2010522268A (ja) * | 2007-03-26 | 2010-07-01 | アルベマール・ユーロプ・エスピーアールエル | 低煙性難燃性ポリウレタンフォーム製剤 |
| ES2377527T3 (es) * | 2007-08-07 | 2012-03-28 | Albemarle Corporation | Pirorretardantes adecuados para el uso en espumas de poliuretano viscoelásticas |
| CN101476479B (zh) * | 2009-01-20 | 2011-01-05 | 中国科学技术大学 | 一种防治矿井煤自燃的泡沫型阻化剂及其使用方法 |
| US9309366B2 (en) | 2011-03-16 | 2016-04-12 | Chemtura Corporation | Reactive flame retardants blends for flexible polyurethane foams |
| US20120264839A1 (en) | 2011-04-14 | 2012-10-18 | Chemtura Corporation | Flame retardant blends for flexible polyurethane foams |
| TWI638005B (zh) | 2011-08-19 | 2018-10-11 | 法克斯聚合物股份有限公司 | 具優越耐火性之熱塑性聚胺基甲酸酯 |
| CN102585148B (zh) * | 2011-12-28 | 2014-04-16 | 万华化学集团股份有限公司 | 制备高阻燃性聚异氰脲酸酯泡沫用组合料 |
| CN103012739B (zh) * | 2012-12-21 | 2014-10-29 | 山东一诺威聚氨酯股份有限公司 | 阻燃改性mdi及其制备方法 |
| EP2948464A4 (en) | 2013-01-22 | 2016-12-07 | Frx Polymers Inc | PHOSPHORUS-BASED EPOXY BINDINGS AND COMPOSITIONS THEREOF |
| WO2014170316A1 (en) * | 2013-04-16 | 2014-10-23 | Basf Se | Phosphorous containing flame retardants |
| GB2523756B (en) * | 2014-03-03 | 2017-01-11 | Addivant Switzerland Gmbh | Antioxidant compositions |
| US10738176B2 (en) | 2016-12-06 | 2020-08-11 | International Business Machines Corporation | Flame-retardant polyallyl and polyalkenyl isocyanurate compounds |
| CN108795543A (zh) * | 2017-05-03 | 2018-11-13 | 中国石油天然气股份有限公司 | 一种工程机械专用液压油组合物 |
| CN112851909B (zh) * | 2021-01-14 | 2022-08-05 | 万华化学（宁波）有限公司 | 一种储存稳定的多异氰酸酯组合物 |
| CN117701239B (zh) * | 2023-12-26 | 2024-06-11 | 苏州添易朗科技有限公司 | 一种uv和热双重固化的改性有机硅胶粘剂及其制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5566917A (en) * | 1978-11-14 | 1980-05-20 | Toyo Tire & Rubber Co Ltd | Manufacture of non-yellowing integral polyurethane foam |
| JPS6150944A (ja) | 1984-08-20 | 1986-03-13 | Agency Of Ind Science & Technol | 新規臭素化フタル酸アリルエステル化合物 |
| JPS61227550A (ja) | 1986-01-24 | 1986-10-09 | Agency Of Ind Science & Technol | 臭素化フタル酸アリル系エステルの製造方法 |
| JPS62298560A (ja) | 1986-06-19 | 1987-12-25 | Nippon Shokubai Kagaku Kogyo Co Ltd | 新規臭素化フタル酸エステル化合物 |
| JPS63251408A (ja) | 1987-04-07 | 1988-10-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | 高屈折率樹脂 |
| FR2681595B1 (fr) | 1991-09-24 | 1994-09-02 | Rhone Poulenc Chimie | Procede d'esterification de sels d'acides carboxyliques. |
| CA2302707A1 (en) * | 1997-09-30 | 1999-04-08 | Rosemarie A. Boccuzzi | Stabilized polyether polyol and polyurethane foam obtained therefrom |
| WO2000035999A1 (en) | 1998-12-18 | 2000-06-22 | The Dow Chemical Company | Polyurethane based foam containing exfoliating graphite and the process for the preparation thereof |
| US6812276B2 (en) | 1999-12-01 | 2004-11-02 | General Electric Company | Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom |
| AU2001230056A1 (en) | 2000-01-13 | 2001-07-24 | Shell Internationale Research Maatschappij B.V. | Polyol formulation |
| US6521703B2 (en) | 2000-01-18 | 2003-02-18 | General Electric Company | Curable resin composition, method for the preparation thereof, and articles derived thereform |
| WO2002062863A2 (en) | 2000-12-29 | 2002-08-15 | World Properties Inc. | Flame retardant polyurethane composition and method of manufacture thereof |
| EP1312630B1 (en) | 2001-10-31 | 2012-12-12 | Tosoh Corporation | Process for the production of flexible polyurethane foams |
| US20030153656A1 (en) | 2002-01-11 | 2003-08-14 | Rinus Sjerps | Flame retardant polyurethanes and polyisocyanurates, and additives therefor |
| AU2002256360A1 (en) | 2002-04-25 | 2003-11-10 | World Properties Inc. | Flame retardant polyurethane composition and method of manufacture thereof |
| US20040171722A1 (en) | 2003-02-28 | 2004-09-02 | Brown William R. | Flame retardant polyurethanes and additive compositions for use in producing them |
-
2003
- 2003-11-21 US US10/719,948 patent/US7153901B2/en not_active Expired - Fee Related
-
2004
- 2004-11-16 EP EP04819525A patent/EP1685176A2/en not_active Withdrawn
- 2004-11-16 CA CA002546299A patent/CA2546299A1/en not_active Abandoned
- 2004-11-16 RU RU2006121970/04A patent/RU2006121970A/ru not_active Application Discontinuation
- 2004-11-16 BR BRPI0417049-0A patent/BRPI0417049A/pt not_active IP Right Cessation
- 2004-11-16 CN CNA2004800342041A patent/CN1882629A/zh active Pending
- 2004-11-16 AU AU2004292526A patent/AU2004292526A1/en not_active Abandoned
- 2004-11-16 UA UAA200606949A patent/UA84722C2/ru unknown
- 2004-11-16 WO PCT/US2004/038071 patent/WO2005052018A2/en not_active Ceased
- 2004-11-16 MX MXPA06005648A patent/MXPA06005648A/es unknown
- 2004-11-16 KR KR1020067009827A patent/KR20060123176A/ko not_active Withdrawn
- 2004-11-16 JP JP2006541291A patent/JP2007513224A/ja not_active Withdrawn
-
2006
- 2006-05-16 IL IL175687A patent/IL175687A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7153901B2 (en) | 2006-12-26 |
| CN1882629A (zh) | 2006-12-20 |
| BRPI0417049A (pt) | 2007-02-06 |
| US20050113495A1 (en) | 2005-05-26 |
| CA2546299A1 (en) | 2005-06-09 |
| KR20060123176A (ko) | 2006-12-01 |
| UA84722C2 (ru) | 2008-11-25 |
| WO2005052018A3 (en) | 2005-08-18 |
| RU2006121970A (ru) | 2007-12-27 |
| JP2007513224A (ja) | 2007-05-24 |
| IL175687A0 (en) | 2006-09-05 |
| WO2005052018A2 (en) | 2005-06-09 |
| EP1685176A2 (en) | 2006-08-02 |
| AU2004292526A1 (en) | 2005-06-09 |
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