JP2012510479A - カルボン酸のビニルエステルを用いてのモノカルボキシ官能化ジアルキルホスフィン酸、そのエステルおよび塩の製法ならびにその使用 - Google Patents
カルボン酸のビニルエステルを用いてのモノカルボキシ官能化ジアルキルホスフィン酸、そのエステルおよび塩の製法ならびにその使用 Download PDFInfo
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- JP2012510479A JP2012510479A JP2011538847A JP2011538847A JP2012510479A JP 2012510479 A JP2012510479 A JP 2012510479A JP 2011538847 A JP2011538847 A JP 2011538847A JP 2011538847 A JP2011538847 A JP 2011538847A JP 2012510479 A JP2012510479 A JP 2012510479A
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- Prior art keywords
- acid
- catalyst
- ester
- monocarboxy
- alkyl
- 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.)
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- 239000002253 acid Substances 0.000 title claims abstract description 118
- 150000002148 esters Chemical class 0.000 title claims abstract description 116
- 150000003839 salts Chemical class 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 63
- 150000007513 acids Chemical class 0.000 title claims abstract description 24
- 229920001567 vinyl ester resin Polymers 0.000 title claims abstract description 14
- 150000001735 carboxylic acids Chemical class 0.000 title abstract description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 title description 2
- -1 azo compound Chemical class 0.000 claims abstract description 120
- 239000003054 catalyst Substances 0.000 claims abstract description 69
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 35
- 150000003624 transition metals Chemical class 0.000 claims abstract description 33
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 23
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 21
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 18
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 17
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 17
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 16
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 16
- 150000001336 alkenes Chemical class 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 229910052718 tin Inorganic materials 0.000 claims abstract description 15
- 229910052742 iron Inorganic materials 0.000 claims abstract description 14
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 14
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 239000003446 ligand Substances 0.000 claims abstract description 12
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 10
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 10
- 239000007800 oxidant agent Substances 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 7
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 7
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 6
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 6
- 150000002829 nitrogen Chemical class 0.000 claims abstract description 5
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 229910052751 metal Inorganic materials 0.000 claims description 50
- 239000002184 metal Substances 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 229920000642 polymer Polymers 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- 239000003063 flame retardant Substances 0.000 claims description 29
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000011575 calcium Substances 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- 239000011591 potassium Chemical group 0.000 claims description 16
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 15
- 239000011777 magnesium Substances 0.000 claims description 15
- 239000012778 molding material Substances 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- 238000000465 moulding Methods 0.000 claims description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 150000002736 metal compounds Chemical class 0.000 claims description 11
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical group [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 11
- 150000002739 metals Chemical class 0.000 claims description 10
- 229910052684 Cerium Inorganic materials 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 229920001169 thermoplastic Polymers 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 8
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 8
- 229920001187 thermosetting polymer Polymers 0.000 claims description 8
- 239000004416 thermosoftening plastic Substances 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 150000004703 alkoxides Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 239000004634 thermosetting polymer Substances 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052500 inorganic mineral Chemical class 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000011707 mineral Chemical class 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052737 gold Inorganic materials 0.000 claims description 5
- 239000010931 gold Substances 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 239000011572 manganese Substances 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002978 peroxides Chemical group 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical group [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 claims description 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229940114081 cinnamate Drugs 0.000 claims description 4
- 239000003599 detergent Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- HPGPEWYJWRWDTP-UHFFFAOYSA-N lithium peroxide Chemical group [Li+].[Li+].[O-][O-] HPGPEWYJWRWDTP-UHFFFAOYSA-N 0.000 claims description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
- 230000002787 reinforcement Effects 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 125000006017 1-propenyl group Chemical group 0.000 claims description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical group NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003810 Jones reagent Substances 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229940117975 chromium trioxide Drugs 0.000 claims description 3
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 claims description 3
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 3
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical compound OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920005594 polymer fiber Polymers 0.000 claims description 3
- 229920006254 polymer film Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 3
- CQMJEZQEVXQEJB-UHFFFAOYSA-N 1-hydroxy-1,3-dioxobenziodoxole Chemical compound C1=CC=C2I(O)(=O)OC(=O)C2=C1 CQMJEZQEVXQEJB-UHFFFAOYSA-N 0.000 claims description 2
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims description 2
- 239000012027 Collins reagent Substances 0.000 claims description 2
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 claims description 2
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- KGMOILGNSGLXOE-UHFFFAOYSA-N but-1-enyl 2,2-dimethylpropanoate Chemical compound CCC=COC(=O)C(C)(C)C KGMOILGNSGLXOE-UHFFFAOYSA-N 0.000 claims description 2
- NLAMRLZPVVKXTK-UHFFFAOYSA-N but-1-enyl acetate Chemical compound CCC=COC(C)=O NLAMRLZPVVKXTK-UHFFFAOYSA-N 0.000 claims description 2
- AUEXPTMDQISBAE-UHFFFAOYSA-N but-1-enyl benzoate Chemical compound CCC=COC(=O)C1=CC=CC=C1 AUEXPTMDQISBAE-UHFFFAOYSA-N 0.000 claims description 2
- WAPXARIYQPWCKL-UHFFFAOYSA-N but-1-enyl butanoate Chemical compound CCCC(=O)OC=CCC WAPXARIYQPWCKL-UHFFFAOYSA-N 0.000 claims description 2
- VNBGOSGMCMHUPT-UHFFFAOYSA-N but-1-enyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=CCC VNBGOSGMCMHUPT-UHFFFAOYSA-N 0.000 claims description 2
- PYZGZDFIRJALLQ-UHFFFAOYSA-N but-1-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=CCC PYZGZDFIRJALLQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims description 2
- WGXGKXTZIQFQFO-CMDGGOBGSA-N ethenyl (e)-3-phenylprop-2-enoate Chemical compound C=COC(=O)\C=C\C1=CC=CC=C1 WGXGKXTZIQFQFO-CMDGGOBGSA-N 0.000 claims description 2
- YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 claims description 2
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 claims description 2
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 claims description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
- BNSOYWDFFBDEFB-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O BNSOYWDFFBDEFB-UHFFFAOYSA-L 0.000 claims description 2
- 238000005470 impregnation Methods 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- CCEBJCJWWSBXIW-UHFFFAOYSA-N prop-1-enyl 2,2-dimethylpropanoate Chemical compound CC=COC(=O)C(C)(C)C CCEBJCJWWSBXIW-UHFFFAOYSA-N 0.000 claims description 2
- IUXQFLRZZUQUPJ-UHFFFAOYSA-N prop-1-enyl benzoate Chemical compound CC=COC(=O)C1=CC=CC=C1 IUXQFLRZZUQUPJ-UHFFFAOYSA-N 0.000 claims description 2
- VZRLITNUXBWTTM-UHFFFAOYSA-N prop-1-enyl butanoate Chemical compound CCCC(=O)OC=CC VZRLITNUXBWTTM-UHFFFAOYSA-N 0.000 claims description 2
- CTZSTTBZAKGVFK-UHFFFAOYSA-N prop-1-enyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=CC CTZSTTBZAKGVFK-UHFFFAOYSA-N 0.000 claims description 2
- QPDZTPISJSOXMN-UHFFFAOYSA-N prop-1-enyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=CC QPDZTPISJSOXMN-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910001927 ruthenium tetroxide Inorganic materials 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 claims description 2
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- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
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- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 150000003002 phosphanes Chemical class 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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- 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 2
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- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
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- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 2
- IWAFYQVHXQRDEZ-UHFFFAOYSA-N (1-bromo-2-methylpropan-2-yl)-ditert-butylphosphane Chemical compound BrCC(C)(C)P(C(C)(C)C)C(C)(C)C IWAFYQVHXQRDEZ-UHFFFAOYSA-N 0.000 description 1
- RTGAJOPJZJDWAX-XVGSOSPHSA-N (1e,4e)-1,5-bis(3,5-dimethoxyphenyl)penta-1,4-dien-3-one;palladium Chemical compound [Pd].COC1=CC(OC)=CC(\C=C\C(=O)\C=C\C=2C=C(OC)C=C(OC)C=2)=C1.COC1=CC(OC)=CC(\C=C\C(=O)\C=C\C=2C=C(OC)C=C(OC)C=2)=C1 RTGAJOPJZJDWAX-XVGSOSPHSA-N 0.000 description 1
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- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
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- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- WXKCRCGKCOKJEF-UHFFFAOYSA-N prop-2-enyl 2-cyanoacetate Chemical compound C=CCOC(=O)CC#N WXKCRCGKCOKJEF-UHFFFAOYSA-N 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
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- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- DAFQZPUISLXFBF-UHFFFAOYSA-N tetraoxathiolane 5,5-dioxide Chemical compound O=S1(=O)OOOO1 DAFQZPUISLXFBF-UHFFFAOYSA-N 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
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- 229910001428 transition metal ion Inorganic materials 0.000 description 1
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- MOSFSEPBWRXKJZ-UHFFFAOYSA-N tridecylphosphane Chemical compound CCCCCCCCCCCCCP MOSFSEPBWRXKJZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- JDUSEMYGYCYQSK-UHFFFAOYSA-L trimagnesium;dioxido(oxidooxy)borane Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]OB([O-])[O-].[O-]OB([O-])[O-] JDUSEMYGYCYQSK-UHFFFAOYSA-L 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical group C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 description 1
- IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- PXYCJKZSCDFXLR-UHFFFAOYSA-N tris[4-(trifluoromethyl)phenyl]phosphane Chemical compound C1=CC(C(F)(F)F)=CC=C1P(C=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 PXYCJKZSCDFXLR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 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
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229940105296 zinc peroxide Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- ZNVKGUVDRSSWHV-UHFFFAOYSA-L zinc;4-hydroxybenzenesulfonate Chemical compound [Zn+2].OC1=CC=C(S([O-])(=O)=O)C=C1.OC1=CC=C(S([O-])(=O)=O)C=C1 ZNVKGUVDRSSWHV-UHFFFAOYSA-L 0.000 description 1
- MFMKGXZULQONRI-UHFFFAOYSA-L zinc;diiodate Chemical compound [Zn+2].[O-]I(=O)=O.[O-]I(=O)=O MFMKGXZULQONRI-UHFFFAOYSA-L 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 1
- YMTQMTSQMKJKPX-UHFFFAOYSA-L zinc;diphenoxide Chemical compound [Zn+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 YMTQMTSQMKJKPX-UHFFFAOYSA-L 0.000 description 1
- MLVWCBYTEFCFSG-UHFFFAOYSA-L zinc;dithiocyanate Chemical compound [Zn+2].[S-]C#N.[S-]C#N MLVWCBYTEFCFSG-UHFFFAOYSA-L 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 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
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4816—Acyclic saturated acids or derivatices which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4866—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the ester moiety containing a substituent or structure which is considered as characteristic
-
- 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Fireproofing Substances (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
アリルニッケル(II)クロリドダイマー、硫酸ニッケル(II)アンモニウム、ビス(1,5−シクロオクタジエン)ニッケル(0)、ビス(トリフェニルホスフィン)ジカルボニルニッケル(0)、テトラキス(トリフェニルホスフィン)ニッケル(0)、テトラキス(トリフェニルホスフィット)ニッケル(0)、ヘキサフルオロニッケル酸(IV)カリウム、テトラシアノニッケル酸(II)カリウム、パラ過ヨウ素酸ニッケル(IV)カリウム、テトラブロモニッケル酸(II)二リチウム、テトラシアノニッケル酸(II)カリウム;
白金(IV)の塩化物、酸化物、硫化物、カリウム、ナトリウム、アンモニウムのヘキサクロロ白金酸塩(IV)、カリウム、アンモニウムのテトラクロロ白金酸塩(II)、テトラシアノ白金酸(II)カリウム、トリメチル(メチルシクロペンタジエニル)白金(IV)、シス−ジアミンテトラクロロ白金(IV)、トリクロロ(エチレン)白金酸(II)カリウム、ヘキサヒドロキシ白金酸(IV)ナトリウム、テトラクロロ白金酸(II)テトラアミン白金(II)、ヘキサクロロ白金酸(IV)テトラブチルアンモニウム、エチレンビス(トリフェニルホスフィン)白金(0)、白金(0)−1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン、白金(0)−2,4,6,8−テトラメチル−2,4,6,8−テトラビニルシクロテトラシロキサン、テトラキス(トリフェニルホスフィン)白金(0)、白金オクタエチルポルフィリン、クロロ白金酸、カルボプラチン;
クロロビス(エチレン)ロジウムダイマー、ヘキサロジウムヘキサデカカルボニル、クロロ(1,5−シクロオクタジエン)ロジウムダイマー、クロロ(ノルボルナジエン)−ロジウムダイマー、クロロ(1,5−ヘキサジエン)ロジウムダイマーである。
PR9 3 (VIII)
式中、基R9は、互いに独立に、水素、直鎖、分枝鎖または環式C1〜C20アルキル、C6〜C20アルキルアリール、C2〜C20アルケニル、C2〜C20アルキニル、C1〜C20カルボキシレート、C1〜C20アルコキシ、C2〜C20アルケニルオキシ、C2〜C20アルキニルオキシ、C2〜C20アルコキシ−カルボニル、C1〜C20アルキルチオ、C1〜C20アルキルスルホニル、C1〜C20アルキルスルフィニル、シリルおよび/またはこれらの誘導体および/または少なくとも1個のR10で置換されているフェニルまたは少なくとも1個のR10で置換されているナフチルである。R10は、互いに独立に、水素、フッ素、塩素、臭素、ヨウ素、NH2、ニトロ、ヒドロキシ、シアノ、ホルミル、直鎖、分枝鎖または環式C1〜C20アルキル、C1〜C20アルコキシ、HN(C1〜C20アルキル)、N(C1〜C20アルキル)2、−CO2−(C1〜C20アルキル)、−CON(C1〜C20アルキル)2、−OCO(C1〜C20アルキル)、NHCO(C1〜C20アルキル)、C1〜C20アシル、−SO3M、−SO2N(R11)M、−CO2M、−PO3M2、−AsO3M2、−SiO2M、−C(CF3)2OM(M=H、Li、NaまたはK)であり、ここで、R11は、水素、フッ素、塩素、臭素、ヨウ素、直鎖、分枝鎖または環式C1〜C20アルキル、C2〜C20アルケニル、C2〜C20アルキニル、C1〜C20カルボキシレート、C1〜C20アルコキシ、C2〜C20アルケニルオキシ、C2〜C20アルキニルオキシ、C2〜C20アルコキシカルボニル、C1〜C20アルキルチオ、C1〜C20アルキルスルホニル、C1〜C20アルキルスルフィニル、シリルおよび/またはその誘導体、アリール、C6〜C20アリールアルキル、C6〜C20アルキルアリール、フェニルおよび/またはビフェニルを意味する。好ましくは、基R9は全て、同じである。
R9 2M”−Z−M”R9 2 (IX)
の二座リガンドである。式中、M”は互いに独立に、N、P、AsまたはSbを表す。好ましくは、両方のM”は同一であり、特に好ましくは、M”はリン原子である。
金、コロイド金、ルテニウム、活性炭担持、炭素担持、アルミナ担持のルテニウム、白金−パラジウム−金合金、金−ニッケル合金、金−ゲルマニウム合金、金−白金合金、金−パラジウム合金、金−ベリリウム合金、白金−ルテニウム合金、パラジウム−ルテニウム合金、金(I)および/または金(III)、ルテニウム(II)および/またはルテニウム(III)および/またはルテニウム(IV)の塩化物、臭化物、ヨウ化物、酸化物、シアン化物、カリウムシアン化物、ナトリウムシアン化物、硫化物、硫酸塩、水素化物、ニトロシル塩化物、ニトロシル硝酸塩、バソフェナントロリン二スルホン酸ナトリウム塩、チオ硫酸塩、過塩素酸塩、シクロペンタジエニル、エチルシクロペンタジエニル、ペンタメチルシクロペンタジエニル、インデニル、2−メチルアリル、プロピオン酸塩、酢酸塩、アセチルアセトナート、ヘキサフルオロアセチルアセトナート、テトラフルオロホウ酸塩、カリウムチオシアン酸塩、ナトリウムチオシアン酸塩、トリフルオロ酢酸塩、ビス(トリフルオロメタンスルホニル)イミド酸塩、ヘキサフルオロアンチモン酸塩、2−ピリジンカルボン酸塩ならびにこれらの1,4−ビス(ジフェニルホスフィン)ブタン錯体、1,3−ビス(ジフェニルホスフィノ)プロパン錯体、2−(2’−ジ−tert−ブチルホスフィン)ビフェニル錯体、アセトニトリル錯体、ベンゾニトリル錯体、ジノルボルニルホスフィン錯体、1,4−ビス(ジフェニルホスフィノ)ブタン錯体、ジメチルフェニルホスフィン錯体、メチルジフェニルホスフィン錯体、トリフェニルホスフィン錯体、トリ−o−トリルホスフィン錯体、トリシクロヘキシルホスフィン錯体、トリブチルホスフィン錯体、トリ−tert−ブチルホスフィン錯体、トリメチルホスフィン錯体、トリエチルホスフィン錯体、2,2’−ビス(ジフェニルホスフィノ)−1,1’−ビナフチル錯体、1,3−ビス(メシチル)イミダゾール−2−イリデン錯体、1,1’−ビス(ジフェニルホスフィノ)フェロセン錯体、(1,1’−ビフェニル−2−イル)ジ−tert−ブチルホスフィン錯体、1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾール−2−イリデン錯体、2−ジシクロヘキシル(2’,4’,6’−トリイソプロピルビフェニル)ホスフィン錯体、ジメチルスルフィド錯体、トリス(2,4−ジ−tert−ブチルフェニル)ホスフィット錯体、トリス(パラ−トリフルオロメチルフェニル)ホスフィン錯体、ビス(ジフェニルホスフィノ)メタン錯体、1,2−ビス(ジフェニルホスフィノ)エタン錯体、N−メチルイミダゾール錯体、1,10−フェナントロリン錯体、4,7−ジフェニル−1,10−フェナントロリン錯体、1,5−シクロオクタジエン錯体、1,3,5−シクロオクタトリエン錯体、ナフタレン錯体、p−シメン錯体、3−メチル−2−ブテニリデン錯体、ベンジリデン錯体、ピリジン錯体、2,3,7,8,12,13,17,18−オクタエチル−21H,23H−ポルフィン錯体、5,10,15,20−テトラフェニル−21H,23H−ポルフィン錯体、N,N,N’,N’−テトラメチルエチレンジアミン錯体、トリ−o−トリルホスフィン錯体、2,2’−ビス(ジフェニルホスフィノ)−1,1’−ビナフチル錯体、1,1’−ビス(ジフェニルホスフィノ)フェロセン錯体、2,2’−ビピリジン錯体、(ビシクロ[2.2.1]ヘプタ−2,5−ジエン)錯体、ビス(ジ−tert−ブチル(4−ジメチルアミノフェニル)ホスフィン)錯体、2−(ジ−tert−ブチルホスフィノ)エチルアミン錯体、(2−(ジフェニルホスフィノ)エチルアミン錯体、1,3−ビス(2,4,6−トリメチルフェニル)−2−イミダゾリジニリデン錯体、1,2−ジアミノシクロヘキサン錯体、ピリジン錯体、カルボニル錯体、エチレンジアミン錯体、アミン錯体;ジシアノ金酸(I)カリウム、テトラクロロ金酸(III)ナトリウム、塩化カリウム金(III)、金チオリンゴ酸ナトリウム、テトラフルオロホウ酸トリス(トリフェニルホスフィン金)オキソニウム、テトラブロモ金酸(III)水素;ヘキサクロロルテニウム酸(IV)アンモニウム、アクアペンタクロロルテニウム酸(III)カリウム、(1,5−シクロオクタジエン)−(1,3,5−シクロオクタトリエン)ルテニウム、トリルテニウムドデカカルボニル、Grubbs触媒。
0.01〜10重量%、好ましくは0.1〜1重量%の残留水分、
0.1〜2000μm、好ましくは10〜500μmの平均粒径、
80〜800g/l、好ましくは200〜700g/lの嵩密度、
0.5〜10、好ましくは1〜5のPfrengle流動性を有する。
V−0:10秒より長い残炎がなく、10回の点火での残炎時間の合計が50秒以下であり、火炎滴下がなく、試験品が完全には燃え尽きず、点火の終了後に30秒より長い試験片の残光がない
V−1:点火の終了後に30秒より長い残炎がなく、10回の点火での残炎時間の合計が250秒以下であり、点火の終了後に60秒より長い試験片の残光がなく、他の基準はV−0と同様
V−2:燃焼滴下により綿が着火、他の基準はV−1と同様
等級外(nkl):燃焼等級V−2を満たさない。
LOI 23 可燃性
LOI 24〜28 条件付きで可燃性
LOI 29〜35 耐燃性
LOI >36 特に耐燃性
VE水 完全脱塩水
AIBN アゾ−ビス−(イソブチロニトリル)、(WAKO Chemicals GmbH社)
WakoV65 2,2’−アゾビス(2,4−ジメチルバレロニトリル)(WAKO Chemicals GmbH社)
Deloxan(登録商標)THP II 金属捕捉剤(Evonik Industries AG社)
室温で、撹拌機および強力凝縮器(intensivkuehler)を備えた三つ口フラスコにまず水188gを投入し、撹拌および窒素導通下で、脱ガスする。次いで、窒素下で、硫酸パラジウム(II)0.2mgおよびトリス(3−スルホフェニル)ホスフィン三ナトリウム塩2.3mgを加え、撹拌し、次いで、水66g中のホスフィン酸66gを加える。反応溶液を2lBuechi反応器に移し、撹拌しながら加圧下でエチレンを入れ、反応混合物を80℃に加熱する。エチレン28gが吸収された後に冷却し、遊離のエチレンを排出する。反応混合物から、回転蒸発器で溶媒を除去する。残渣にVE水100gを加え、室温、窒素雰囲気下で撹拌し、次いで、濾過し、濾液をトルエンで抽出し、その後、回転蒸発器で溶媒を除去し、得られたエチル亜ホスホン酸を回収する。こうして、エチル亜ホスホン酸92g(理論量の98%)が得られる。
例1におけると同様にして、ホスフィン酸99g、ブタノール396g、エチレン42g、トリス(ジベンジリデンアセトン)ジパラジウム6.9mg、4,5−ビス(ジフェニルホスフィノ)−9,9−ジメチルキサンテン9.5mgを反応させ、次いで、精製のために、Deloxan(登録商標)THP IIを充填したカラムに通し、次いで、n−ブタノールを再び加える。80〜110℃の反応温度で、生じた水を共沸蒸留により除去する。生成物(エチル亜ホスホン酸ブチルエステル)を減圧下での蒸留により精製する。こうして、エチル亜ホスホン酸ブチルエステル189g(理論量の84%)が得られる。
例1におけると同様にして、ホスフィン酸198g、水198g、エチレン84g、硫酸パラジウム(II)6.1mg、9,9−ジメチル−4,5−ビス(ジフェニルホスフィノ)−2,7−スルホナトキサンテン二ナトリウム塩25.8mgを反応させ、次いで、精製のために、Deloxan(登録商標)THP IIを充填したカラムに通し、その後、n−ブタノールを加える。80〜110℃の反応温度で、生じた水を共沸蒸留により除去する。生成物(エチル亜ホスホン酸ブチルエステル、374g(理論量の83%))を減圧下での蒸留により精製する。
ガス入口管、温度計、強力撹拌機およびガス燃焼を伴う還流凝縮器を備えた500ml五つ口フラスコに、まずエチル亜ホスホン酸94g(1mol)(例1におけると同様にして製造)を投入する。室温で、エチレンオキシドを導入する。冷却下で、反応温度を70℃に調節し、80℃でさらに1時間反応させる。エチレンオキシド吸収は、65.7gである。生成物の酸価は、1mgKOH/g未満である。(エチル亜ホスホン酸2−ヒドロキシエチルエステル)129g(理論量の94%)が、無色透明の生成物として得られる。
エチル亜ホスホン酸564g(6mol)を水860gに溶かし、温度計、還流凝縮器、強力撹拌機および滴下漏斗を備えた5l五つ口フラスコにまず投入する。反応混合物を100℃に加熱した後に、大気圧で、酢酸ビニル602g(7mol)および5%ペルオキソ二硫酸ナトリウム溶液500g(酢酸ビニルに対して1.5mol%)を1時間以内で滴加する。続いて、水を真空下で留去する。残渣をテトラヒドロフランに入れ、不溶性の塩を濾別する。濾液の溶媒を真空中で分離する。クロマトグラフィーによる精製の後に、エチル−(2−アセトキシエチル)ホスフィン酸1.026g(理論量の95%)がオイルとして得られる。
ブタノール200g中のエチル亜ホスホン酸94g(1mol)(例1におけると同様にして製造)および酢酸ビニル86g(1mol)を撹拌機、還流凝縮器、温度計および窒素入口を備えた四つ口丸底フラスコ内のエタノール200ml中にまず投入し、加温する。1時間以内、約100℃で、5%AlBNのエタノール溶液98.4gを滴加する。その後、溶媒を真空中で留去した。クロマトグラフィーによる精製の後に、エチル−(2−アセトキシエチル)ホスフィン酸215g(理論量の91%)が得られる。
エチル亜ホスホン酸ブチルエステル150g(1mol)(例2に従って製造)および酪酸ビニル137g(1.2mol)をトルエン217g中で約100℃に加温する。撹拌下で、トルエン中10%のWakoV65溶液124gを配量添加する。溶媒を真空中で留去する。クロマトグラフィーによる精製の後に、エチル−(2−ブチルオキシエチル)ホスフィン酸ブチルエステル227g(理論量の86%)が得られる。
撹拌装置に、エチル(2−アセトキシエチル)ホスフィン酸(例6におけると同様にして製造)180g(1mol)を濃塩酸200ml(2mol)に溶かす。混合物を十分に撹拌しながら、約90℃に加温し、この温度で、約8時間反応させた。続いて、水を真空中で完全に留去する。残渣を酢酸に入れ、抽出する。濾液の溶媒を真空中で分離する。エチル−(2−ヒドロキシエチル)ホスフィン酸143g(理論量の94%)がオイルとして得られる。
撹拌装置に、ブタノール150g、水65g、水酸化ナトリウム150g(3.75mol)およびエチル(2−ブチルオキシエチル)−ホスフィン酸ブチルエステル330g(1.25mol)(例7におけると同様にして製造)をまず投入する。混合物を十分に撹拌しながら約120℃に加温し、この温度で約6時間反応させた。続いて、水250mlを加え、ブタノールを、蒸留により反応混合物から除去した。さらなる水500mlを加えた後に、濃硫酸約184g(1.88mol)を加えることにより、混合物を中和した。続いて、水を真空中で留去する。残渣をテトラヒドロフランに入れ、抽出する。不溶性の塩を濾別する。濾液の溶媒を真空中で留去する。エチル−(2−ヒドロキシエチル)ホスフィン酸220g(理論量の98%)がオイルとして得られる。
エチル−(2−ヒドロキシエチル)ホスフィン酸13.8g(0.1mol)(例8におけると同様にして製造)を水150mlに溶かし、2NのNaOH溶液を用いてpH9にする。続いて、Pt5%およびBi1%を含む活性炭0.45gを加え、この懸濁液を70℃に加温し、空気(10l/h)を懸濁液に導通させる。この際、懸濁液のpHを、2NのNaOH溶液を加えることによりpH=9に保持する。反応の終了後に、反応溶液から触媒を濾別し、洗浄し、塩酸で酸性にし、水を真空中で留去する。残渣をテトラヒドロフランに入れ、抽出する。不溶性の塩を濾別する。2−(エチルヒドロキシホスフィニル)酢酸14.0g(理論量の92%)が無色の固体として得られる。
エチル−(2−ヒドロキシエチル)ホスフィン酸13.8g(0.1mol)(例9におけると同様にして製造)を水150mlに溶かし、2NのNaOH溶液を用いてpH9に調節する。続いて、Pd5%およびBi1%を含む活性炭0.25gを加え、この懸濁液を70℃に加温し、30%過酸化水素溶液を1時間当たり1モル当量の流速で懸濁液に導通させる。この際、懸濁液のpHを、2NのNaOH溶液を加えることによりpH=9に保持する。反応の終了後に、反応溶液から触媒を濾別し、洗浄し、塩酸で酸性にし、水を真空中で留去する。残渣をテトラヒドロフランに入れ、抽出する。不溶性の塩を濾別する。2−(エチルヒドロキシホスフィニル)酢酸14.0g(理論量の92%)が無色の固体として得られる。
アセトン500ml中のエチル−(2−ヒドロキシエチル)ホスフィン酸13.8g(0.1mol)(例8におけると同様にして製造)に、Jones試薬0.11mol(水36.7mlおよび濃硫酸11.0ml中の三酸化クロム12.7g)を0℃で滴加した。反応混合物をさらに、氷冷しながら3時間半、および室温で1時間撹拌した。イソプロパノール12mlを加えた後に、氷水を加える。続いて、易揮発性成分を真空中で留去する。残渣をテトラヒドロフランに入れ、抽出する。不溶性の塩を濾別した。濾液の溶媒を真空中で分離し、残渣をアセトンから再結晶化させた。2−(エチルヒドロキシホスフィニル)酢酸12.3g(理論量の81%)が無色の固体として得られる。
2−(エチルヒドロキシホスフィニル)酢酸304g(2mol)の水溶液(例10に従って製造)を50%水酸化ナトリウム水溶液約160gと反応させ、水を真空中で留去する。2−(エチルヒドロキシホスフィニル)酢酸ナトリウム塩384g(理論量の98%)が無色の固体として得られた。
2−(エチルヒドロキシホスフィニル)酢酸912g(6mol)(例12におけると同様にして製造)を水860gに溶かし、温度計、還流凝縮器、強力撹拌機および滴下漏斗を備えた5l五つ口フラスコにまず投入し、50%水酸化ナトリウム溶液約960g(12mol)で中和する。85℃で、Al2(SO4)3・14H2Oの46%水溶液2583gである混合物を加える。続いて、得られた固体を濾別し、熱水で洗浄し、130℃、真空で乾燥させる。収量:無色の塩としての2−(エチルヒドロキシホスフィニル)酢酸アルミニウム(III)塩958g(理論量の95%)
2−(エチルヒドロキシホスフィニル)酢酸152g(1mol)(例11におけると同様にして製造)およびチタンテトラブチラート170gをトルエン500ml中で40時間還流加熱する。この際に生じるブタノールをトルエン成分と共に時々留去する。生じた溶液から、続いて溶媒を除去する。2−(エチルヒドロキシホスフィニル)酢酸チタン塩167g(理論量の96%)が得られる。
2−(エチルヒドロキシホスフィニル)酢酸456g(3mol)(例10におけると同様にして製造)を85℃で、トルエン400mlに溶かし、ブタノール888g(12mol)を加える。約100℃の反応温度で、生じた水を共沸蒸留により除去する。生成物2−(エチルブトキシホスフィニル)酢酸ブチルエステル(705g(理論量の89%))を減圧下で蒸留により精製する。
2−(エチルヒドロキシホスフィニル)酢酸456g(3.0mol)(例11におけると同様にして製造)を80℃でトルエン400mlに溶かし、1,4−ブタンジオール594g(6.6mol)を加え、水分離器を備えた蒸留装置中、約100℃で4時間エステル化させる。エステル化が終了した後に、トルエンを真空中で分離する。2−(エチル−4−ヒドロキシブチルホスフィニル)酢酸4−ヒドロキシブチルエステル781g(理論量の88%)が無色のオイルとして得られる。
2−(エチルブトキシホスフィニル)酢酸ブチルエステル528g(2mol)(例16におけると同様にして製造)にエチレングリコール155g(2.5mol)およびチタニルシュウ酸カリウム0.4gを加え、200℃で2時間撹拌する。徐々に排気することにより、易揮発性成分を留去する。リン12.2%を含有する2−(エチル−2−ヒドロキシエトキシホスフィニル)酢酸2−ヒドロキシエチルエステル494g(理論量の98%)が得られる。
2−(エチル−2−ヒドロキシエトキシホスフィニル)酢酸2−ヒドロキシエチルエステル25.4g(例18におけると同様にして製造)に、テレフタル酸290g、エチレングリコール188g、酢酸亜鉛0.34gを加え、200℃に2時間加熱する。次いで、リン酸三ナトリウム無水物0.29gおよび酸化アンチモン(III)0.14gを加え、280℃に加熱し、その後、排気する。得られた溶融物(355g、リン含量0.9%)から、酸素指数(LOI)をISO4589−2により測定するため、および火炎試験UL94(Underwriter Laboratories)のための厚さ1.6mmの試験片を射出成形する。こうして得られた試験片は38%のLOIを示し、UL94による火炎等級V−0を満たした。2−(エチル−2−ヒドロキシエトキシホスフィニル)−酢酸2−ヒドロキシエチルエステルを含有しない対応する試験片は、僅か31%のLOIを示し、UL94による火炎等級V−2を満たすのみであった。したがって、2−(エチル−2−ヒドロキシエトキシホスフィニル)−酢酸2−ヒドロキシエチルエステルを含有するポリエステル成形体は明らかに、難燃特性を示す。
2−(エチルヒドロキシホスフィニル)−酢酸12.8g(例10におけると同様にして製造)に、1,3−プロピレングリコール12.9gを加え、エステル化で生じた水を160℃で除去する。次いで、テレフタル酸ジメチル378g、1,3−プロパンジオール152g、チタン酸テトラブチル0.22gおよび酢酸リチウム0.05gを加え、混合物を撹拌しながら130〜180℃に2時間加熱し、その後、減圧下で270℃に加熱する。ポリマー(434g)は、リン0.6%を含有し、LOIは34である。
2−(エチルヒドロキシホスフィニル)−酢酸12.8g(例12におけると同様にして製造)に、テレフタル酸ジメチル367g、1,4−ブタンジオール170g、チタン酸テトラブチル0.22gおよび酢酸リチウム0.05gを加え、混合物を撹拌しながら、まず130〜180℃に2時間、次いで、減圧下で270℃に加熱する。ポリマー(424g)はリン0.6%を含有し、LOIは34であり、未処理のポリブチレンテレフタレートのLOIは23である。
還流凝縮器、撹拌機、温度計および窒素入口を備えた250ml五つ口フラスコで、エポキシ値0.55mol/100gを有するビスフェノール−A−ビスグリシジルエーテル100g(Beckopox EP 140、Solutia社)および2−(エチルヒドロキシホスフィニル)−酢酸19.8g(0.13mol)(例12においてと同様に製造)を撹拌しながら、最高150℃に加熱する。30分後に、透明な溶融物が生じる。150℃でさらに1時間撹拌した後に、溶融物を冷却し、乳鉢で破砕する。リン含量3.3重量%を有する白色の粉末118.5gが得られる。
撹拌機、水分離器、温度計、還流凝縮器および窒素入口を備えた2lフラスコで、フタル酸無水物29.4g、マレイン酸無水物19.6g、プロピレングリコール24.8g、2−(エチル−2−ヒドロキシエチルホスフィニル)−酢酸2−ヒドロキシエチルエステル17.7g(例18におけると同様にして製造)、キシレン20gおよびヒドロキノン50mgを撹拌しながら、および窒素を通過させながら100℃に加熱する。発熱反応が始まったら、加熱を外す。反応が和らいだ後に、約190℃でさらに撹拌する。水14gを分離した後に、キシレンを留去し、ポリマー溶融物を冷却する。2.3重量%のリン含量を有する白色の粉末88.7gが得られる。
ポリブチレンテレフタレート50重量%、2−(エチルヒドロキシホスフィニル)−酢酸アルミニウム(III)塩20重量%(例14におけると同様にして製造)とガラス繊維30重量%の混合物を二軸スクリュー押出機(Leistritz LSM 30/34型)で230〜260℃の温度で配合して、ポリマー成形材料にする。均質なポリマーストランドを押し出し、水浴中で冷却し、続いてペレット化する。乾燥の後に、成形材料を射出成形装置(Aarburg Allrounder型)で240〜270℃で加工してポリマー成形体にすると、UL−94等級V−0と決定される。
ポリアミド6.6 53重量%、ガラス繊維30重量%、2−(エチルヒドロキシホスフィニル)−酢酸チタン塩17重量%(例15におけると同様にして製造)の混合物を二軸スクリュー押出機(Leistritz LSM 30/34型)で配合してポリマー成形材料にする。均質なポリマーストランドを押し出し、水浴中で冷却し、続いてペレット化する。乾燥の後に、成形材料を射出成形装置(Aarburg Allrounder型)で260〜290℃で加工してポリマー成形体にすると、UL−94等級V−0が得られる。
Claims (17)
- モノカルボキシ官能化ジアルキルホスフィン酸、そのエステルおよび塩を製造する方法において、
a)ホスフィン酸源(I)を
- ステップd)に従って得られた前記モノカルボキシ官能化ジアルキルホスフィン酸、その塩またはそのエステル(III)を続いてステップe)で、Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、Kの金属化合物および/またはプロトン化窒素塩基と反応させて、これらの金属および/または窒素化合物の対応するモノカルボキシ官能化ジアルキルホスフィン酸塩(III)にすることを特徴とする、請求項1に記載の方法。
- ステップa)に従って得られた前記アルキル亜ホスホン酸、その塩またはエステル(II)および/またはステップb)に従って得られた前記一官能化ジアルキルホスフィン酸、その塩またはエステル(VI)および/またはステップc)に従って得られた前記一官能化ジアルキルホスフィン酸、その塩またはエステル(VII)および/またはステップd)に従って得られた前記モノカルボキシ官能化ジアルキルホスフィン酸、その塩またはエステル(III)および/またはそれぞれ生じるその反応溶液を、アルキレンオキシドまたはアルコールM−OHおよび/またはM’−OHでエステル化し、その時々に生じるアルキル亜ホスホン酸エステル(II)、一官能化ジアルキルホスフィン酸エステル(VI)および/または(VII)および/またはモノカルボキシ官能化ジアルキルホスフィン酸エステル(III)に、さらなる反応ステップb)、c)、d)またはe)を施すことを特徴とする、請求項1に記載の方法。
- 前記基C6〜C18アリール、C6〜C18アラルキルおよびC6〜C18アルキル−アリールが、SO3X2、COCH3、OH、CH2OH、CH3SO3X2、PO3X2、NH2、NO2、OCH3、SHおよび/またはOC(O)CH3で置換されていることを特徴とする、請求項1〜3のいずれか一つに記載の方法。
- R1、R2、R3、R4、R5、R6、R7が、同じかまたは異なり、互いに独立にH、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチルおよび/またはフェニルを意味することを特徴とする、請求項1〜4のいずれか一つに記載の方法。
- XおよびYが、同じかまたは異なり、それぞれH、Ca、Mg、Al、Zn、Ti、Fe、Ce、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert−ブチル、フェニル、エチレングリコール、プロピルグリコール、ブチルグリコール、ペンチルグリコール、ヘキシルグリコール、アリルおよび/またはグリセリンを意味することを特徴とする、請求項1〜5のいずれか一つに記載の方法。
- 前記遷移金属および/または遷移金属化合物が、第1、第7および第8亜族からのものであることを特徴とする、請求項1〜6のいずれか一つに記載の方法。
- 前記遷移金属および/または遷移金属化合物が、ロジウム、ニッケル、パラジウム、白金、ルテニウムおよび/または金であることを特徴とする、請求項1〜7のいずれか一つに記載の方法。
- 前記触媒Bが、過酸化水素、過酸化ナトリウム、過酸化リチウム、過硫酸カリウム、過硫酸ナトリウム、過硫酸アンモニウム、ペルオキソ二硫酸ナトリウム、ペルオキソホウ酸カリウム、過酢酸、過酸化ベンゾイル、過酸化ジ−t−ブチルおよび/またはペルオキソ二硫酸、および/またはアゾジイソブチロニトリル、2,2’−アゾビス(2−アミジノプロパン)−ジヒドロクロリドおよび/または2,2’−アゾビス(N,N’−ジメチレン−イソブチルアミジン)ジヒドロクロリドであることを特徴とする、請求項1〜8のいずれか一つに記載の方法。
- 前記触媒Cが、金属、金属水素化物、金属水酸化物および金属アルコキシド、ならびに鉱酸、例えば硫酸、硝酸、塩酸、リン酸またはこれらの混合物であることを特徴とする、請求項1〜9のいずれか一つに記載の方法。
- 前記酸化剤が、過マンガン酸カリウム、二酸化マンガン、三酸化クロム、重クロム酸カリウム、重クロム酸ピリジン、クロロクロム酸ピリジン、Collins試薬、Jones試薬、Corey−Gilman−Ganem試薬、(Dess−Martin)ペルヨージナン、o−ヨードキシ安息香酸、四酸化ルテニウム、二酸化ルテニウム、テトラ−n−プロピル−ペルルテネート、三塩化ルテニウム/過ヨウ素酸ナトリウム、二酸化ルテニウム/過ヨウ素酸ナトリウム、塩素、次亜塩素酸塩およびペルオキソ化合物であることを特徴とする、請求項1〜10のいずれか一つに記載の方法。
- 前記カルボン酸のビニルエステル(V)が、酢酸ビニル、プロピオン酸ビニル、酪酸ビニル、ピバル酸ビニル、安息香酸ビニル、ケイ皮酸ビニル、ステアリン酸ビニル、ラウリン酸ビニル、酢酸1−プロペニル、プロピオン酸1−プロペニル、酪酸1−プロペニル、ピバル酸1−プロペニル、安息香酸1−プロペニル、ケイ皮酸1−プロペニル、ステアリン酸1−プロペニル、ラウリン酸1−プロペニル、酢酸1−ブテニル、プロピオン酸1−ブテニル、酪酸1−ブテニル、ピバル酸1−ブテニル、安息香酸1−ブテニル、ケイ皮酸1−ブテニル、ステアリン酸1−ブテニル、ラウリン酸1−ブテニルであることを特徴とする、請求項1〜11のいずれか一つに記載の方法。
- 一般式M−OHの前記アルコールが、C1〜C18の炭素鎖長を有する直鎖または分枝鎖、飽和および不飽和の一価有機アルコールであり、一般式M’−OHの前記アルコールが、C1〜C18の炭素鎖長を有する直鎖または分枝鎖、飽和および不飽和の多価有機アルコールであることを特徴とする、請求項1〜12のいずれか一つに記載の方法。
- 請求項1〜13のいずれか一つの記載に従って製造されたモノカルボキシ官能化ジアルキルホスフィン酸、そのエステルおよび塩の、さらなる合成のための中間生成物として、結合剤として、エポキシ樹脂、ポリウレタンおよび不飽和ポリエステル樹脂を硬化させる際の架橋剤または促進剤として、ポリマー安定剤として、農薬として、ヒトおよび動物用の治療薬または治療薬添加剤として、金属イオン封鎖剤として、鉱油添加剤として、防食剤として、洗濯洗剤および洗浄剤用途において、ならびに電子用途においての使用。
- 請求項1〜13のいずれか一つの記載に従って製造されたモノカルボキシ官能化ジアルキルホスフィン酸、その塩およびエステルの、難燃剤、特にクリヤコートおよび発泡性防炎塗料用の難燃剤、木材および他のセルロース含有製品用の難燃剤として、ポリマー用の反応性および/または非反応性難燃剤として、難燃性ポリマー成形材料を製造するため、難燃性ポリマー成形体を製造するため、および/または含浸によりポリエステルおよびセルロース製の純粋および混紡織物を難燃性にするための使用。
- 請求項1〜13のいずれか一つの記載に従って製造されたモノカルボキシ官能化ジアルキルホスフィン酸、その塩またはエステル0.5〜45重量%、熱可塑性もしくは熱硬化性ポリマーまたはその混合物0.5〜95重量%、添加剤0〜55重量%ならびに充填剤または強化材0〜55重量%(ここで、成分の合計は100重量%である)を含有する難燃性熱可塑性または熱硬化性ポリマー成形材料。
- 請求項1〜13のいずれか一つの記載に従って製造されたモノカルボキシ官能化ジアルキルホスフィン酸、その塩またはエステル0.5〜45重量%、熱可塑性もしくは熱硬化性ポリマーまたはその混合物0.5〜95重量%、添加剤0〜55重量%ならびに充填剤または強化材0〜55重量%(ここで、成分の合計は100重量%である)を含有する難燃性熱可塑性または熱硬化性ポリマー成形体、ポリマーフィルム、ポリマーフィラメントおよびポリマー繊維。
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Also Published As
Publication number | Publication date |
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DE102008060036A1 (de) | 2010-06-10 |
CN102171227B (zh) | 2014-11-12 |
EP2373667B1 (de) | 2013-12-11 |
ES2448577T3 (es) | 2014-03-14 |
JP5619765B2 (ja) | 2014-11-05 |
US20110237721A1 (en) | 2011-09-29 |
EP2373667A1 (de) | 2011-10-12 |
US8735476B2 (en) | 2014-05-27 |
WO2010063342A1 (de) | 2010-06-10 |
CN102171227A (zh) | 2011-08-31 |
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