CN102171230B - 用于阻燃剂的亚膦酸衍生物的加氢磷酰化 - Google Patents
用于阻燃剂的亚膦酸衍生物的加氢磷酰化 Download PDFInfo
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- CN102171230B CN102171230B CN200980138912.2A CN200980138912A CN102171230B CN 102171230 B CN102171230 B CN 102171230B CN 200980138912 A CN200980138912 A CN 200980138912A CN 102171230 B CN102171230 B CN 102171230B
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- 239000003063 flame retardant Substances 0.000 title description 38
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 147
- 150000001336 alkenes Chemical class 0.000 claims abstract description 111
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 63
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 45
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 36
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 24
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 14
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 14
- 229910052742 iron Inorganic materials 0.000 claims abstract description 13
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 11
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 8
- -1 isobutyl- Chemical group 0.000 claims description 219
- 150000005690 diesters Chemical class 0.000 claims description 87
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 71
- 150000002148 esters Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 40
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 239000011591 potassium Substances 0.000 claims description 40
- 239000011734 sodium Substances 0.000 claims description 35
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 31
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 229910052723 transition metal Inorganic materials 0.000 claims description 29
- 150000003624 transition metals Chemical class 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 26
- 229910052782 aluminium Inorganic materials 0.000 claims description 25
- 239000002585 base Substances 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000011701 zinc Substances 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 150000002736 metal compounds Chemical class 0.000 claims description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 15
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 15
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 13
- 239000011575 calcium Substances 0.000 claims description 13
- 239000010936 titanium Substances 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 11
- 239000004411 aluminium Substances 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000011777 magnesium Substances 0.000 claims description 10
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229960004063 propylene glycol Drugs 0.000 claims description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 8
- ZCHHRLHTBGRGOT-SNAWJCMRSA-N (E)-hex-2-en-1-ol Chemical compound CCC\C=C\CO ZCHHRLHTBGRGOT-SNAWJCMRSA-N 0.000 claims description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 8
- 229910052728 basic metal Inorganic materials 0.000 claims description 8
- UIZVMOZAXAMASY-UHFFFAOYSA-N hex-5-en-1-ol Chemical compound OCCCCC=C UIZVMOZAXAMASY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- ZCHHRLHTBGRGOT-PLNGDYQASA-N (z)-hex-2-en-1-ol Chemical compound CCC\C=C/CO ZCHHRLHTBGRGOT-PLNGDYQASA-N 0.000 claims description 6
- BVOSSZSHBZQJOI-UHFFFAOYSA-N 1-Hexen-3-ol Chemical compound CCCC(O)C=C BVOSSZSHBZQJOI-UHFFFAOYSA-N 0.000 claims description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- VTIODUHBZHNXFP-UHFFFAOYSA-N hex-4-en-1-ol Chemical compound CC=CCCCO VTIODUHBZHNXFP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 235000013772 propylene glycol Nutrition 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical group [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 claims description 6
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical group [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 6
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 5
- 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 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003818 basic metals Chemical class 0.000 claims description 5
- 150000004054 benzoquinones Chemical class 0.000 claims description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 5
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 229940059574 pentaerithrityl Drugs 0.000 claims description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- 239000004159 Potassium persulphate Chemical group 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 150000001409 amidines Chemical class 0.000 claims description 4
- 235000019395 ammonium persulphate Nutrition 0.000 claims description 4
- 229910052788 barium Inorganic materials 0.000 claims description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 4
- HPGPEWYJWRWDTP-UHFFFAOYSA-N lithium peroxide Chemical group [Li+].[Li+].[O-][O-] HPGPEWYJWRWDTP-UHFFFAOYSA-N 0.000 claims description 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 4
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 claims description 4
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 claims description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 4
- 235000019394 potassium persulphate Nutrition 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 3
- AYQPVPFZWIQERS-VOTSOKGWSA-N (E)-oct-2-en-1-ol Chemical compound CCCCC\C=C\CO AYQPVPFZWIQERS-VOTSOKGWSA-N 0.000 claims description 3
- WUOACPNHFRMFPN-VIFPVBQESA-N (R)-(+)-alpha-terpineol Chemical compound CC1=CC[C@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-VIFPVBQESA-N 0.000 claims description 3
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 claims description 3
- BKILWHYRLBCASZ-UHFFFAOYSA-M 2-[bis(2-hydroxyethyl)amino]ethanol;2-hydroxypropanoate;phenylmercury(1+) Chemical compound CC(O)C([O-])=O.[Hg+]C1=CC=CC=C1.OCCN(CCO)CCO BKILWHYRLBCASZ-UHFFFAOYSA-M 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 claims description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000004160 Ammonium persulphate Chemical group 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004386 Erythritol Substances 0.000 claims description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 3
- 229930192627 Naphthoquinone Natural products 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- AYQPVPFZWIQERS-UHFFFAOYSA-N cis-2-octen-1-ol Natural products CCCCCC=CCO AYQPVPFZWIQERS-UHFFFAOYSA-N 0.000 claims description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 3
- 229940009714 erythritol Drugs 0.000 claims description 3
- 235000019414 erythritol Nutrition 0.000 claims description 3
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 claims description 3
- 229960005150 glycerol Drugs 0.000 claims description 3
- LNPNXWKVAFKIBX-UHFFFAOYSA-N hex-5-en-2-ol Chemical compound CC(O)CCC=C LNPNXWKVAFKIBX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000011133 lead Substances 0.000 claims description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 150000002791 naphthoquinones Chemical class 0.000 claims description 3
- 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 claims description 3
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- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-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
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229960003761 propamidine Drugs 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- GJPYYNMJTJNYTO-UHFFFAOYSA-J sodium aluminium sulfate Chemical compound [Na+].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GJPYYNMJTJNYTO-UHFFFAOYSA-J 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- UHCGLDSRFKGERO-UHFFFAOYSA-N strontium peroxide Chemical compound [Sr+2].[O-][O-] UHCGLDSRFKGERO-UHFFFAOYSA-N 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- UWNNZXDNLPNGQJ-UHFFFAOYSA-N tert-butyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(C)(C)C UWNNZXDNLPNGQJ-UHFFFAOYSA-N 0.000 description 1
- KVWOTUDBCFBGFJ-UHFFFAOYSA-N tert-butyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)C KVWOTUDBCFBGFJ-UHFFFAOYSA-N 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000008467 tissue growth Effects 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 229910000349 titanium oxysulfate Inorganic materials 0.000 description 1
- CMWCOKOTCLFJOP-UHFFFAOYSA-N titanium(3+) Chemical compound [Ti+3] CMWCOKOTCLFJOP-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- ROUPZXDBSPQFLE-UHFFFAOYSA-N triazanium;phosphate;hydrate Chemical compound [NH4+].[NH4+].[NH4+].O.[O-]P([O-])([O-])=O ROUPZXDBSPQFLE-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-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-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- NGOCMUBXJDDBLB-UHFFFAOYSA-N trifluoromethanesulfonic acid;zinc Chemical compound [Zn].OS(=O)(=O)C(F)(F)F NGOCMUBXJDDBLB-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
- 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
- ZBZHVBPVQIHFJN-UHFFFAOYSA-N trimethylalumane Chemical compound C[Al](C)C.C[Al](C)C ZBZHVBPVQIHFJN-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 229940048102 triphosphoric acid Drugs 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
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-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
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 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
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- 239000011576 zinc lactate Substances 0.000 description 1
- 235000000193 zinc lactate Nutrition 0.000 description 1
- 229940050168 zinc lactate Drugs 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- OMSYGYSPFZQFFP-UHFFFAOYSA-J zinc pyrophosphate Chemical compound [Zn+2].[Zn+2].[O-]P([O-])(=O)OP([O-])([O-])=O OMSYGYSPFZQFFP-UHFFFAOYSA-J 0.000 description 1
- XSMMCTCMFDWXIX-UHFFFAOYSA-N zinc silicate Chemical compound [Zn+2].[O-][Si]([O-])=O XSMMCTCMFDWXIX-UHFFFAOYSA-N 0.000 description 1
- 235000019352 zinc silicate Nutrition 0.000 description 1
- 229940006174 zinc valerate Drugs 0.000 description 1
- VRGNUPCISFMPEM-ZVGUSBNCSA-L zinc;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Zn+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O VRGNUPCISFMPEM-ZVGUSBNCSA-L 0.000 description 1
- HJSYJHHRQVHHMQ-ODZAUARKSA-L zinc;(z)-but-2-enedioate Chemical compound [Zn+2].[O-]C(=O)\C=C/C([O-])=O HJSYJHHRQVHHMQ-ODZAUARKSA-L 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- AGFGXVAAIXIOFZ-UHFFFAOYSA-L zinc;butanedioate Chemical compound [Zn+2].[O-]C(=O)CCC([O-])=O AGFGXVAAIXIOFZ-UHFFFAOYSA-L 0.000 description 1
- WDHVIZKSFZNHJB-UHFFFAOYSA-L zinc;butanoate Chemical compound [Zn+2].CCCC([O-])=O.CCCC([O-])=O WDHVIZKSFZNHJB-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-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
- HHIMNFJHTNVXBJ-UHFFFAOYSA-L zinc;dinitrite Chemical compound [Zn+2].[O-]N=O.[O-]N=O HHIMNFJHTNVXBJ-UHFFFAOYSA-L 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
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
- BUDAIZWUWHWZPQ-UHFFFAOYSA-L zinc;pentanoate Chemical compound [Zn+2].CCCCC([O-])=O.CCCCC([O-])=O BUDAIZWUWHWZPQ-UHFFFAOYSA-L 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- VXEZTJBNLUVPGK-UHFFFAOYSA-N zirconium(4+) hydrate Chemical compound O.[Zr+4] VXEZTJBNLUVPGK-UHFFFAOYSA-N 0.000 description 1
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic 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
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Abstract
本发明涉及由a)和b)形成的加合物,a)式(I)的烷基亚膦酸衍生物A-P(=O)(OX)-H(I),其中,A表示任选取代的C2-C18-烷基、C2-C18-烯基、C6-C18-芳烷基、C6-C18-芳烷基,和X表示H,任选取代的C1-C18-烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基、C2-C18-烯基,Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K、H和/或质子化的氮碱,和b)式(II)的可形成二酯的烯烃,其中,R2、R4相同或不同并表示CO2H、CO2R5、R6-CO2H、R6-CO2R5,且R1、R3相同或不同并表示H、R5;或者R1、R4相同或不同并表示CO2H、CO2R5、R6-CO2H、R6-CO2R5,且R2、R3相同或不同并表示H、R5;或者R2、R4相同或不同并表示-CO-O-CO-、-CO-S-CO-、-CO-NR1-CO-、-CO-PR1-CO-,且R1、R3相同或不同并表示H、R5;或者R1、R2相同或不同并表示CO2H、CN、CO2R5、R6-CO2H、R6-CO2R5,且R3、R4相同或不同并表示H、R5;或者R1、R2相同或不同并表示-CR2 3-CO-O-CO-、-CR2 3-CO-NR1-CO-、-CR2 3-CO-O-CO-CR2 3、-CR2 3-CO-NR1-CO-CR2 3,且R3、R4相同或不同并表示H、R5;或者R2和R4各自表示-CO-CR5=CR5-CO-,且R1、R3相同或不同并表示H、R5;R5=C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;R6=C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基;制备它们的方法和它们的用途。
Description
本发明涉及烷基亚膦酸衍生物和可形成二酯的烯烃的无卤加合物,用于它们的制备的无卤素的方法和它们的用途。
烷基亚膦酸衍生物和可形成二酯的烯烃的加合物仅仅是部分已知的,因为迄今为止它们完全不能获得或非常难于获得。尤其迄今为止不能以无卤素的方式制备产品。
氧杂-10-磷杂菲和可形成二酯的烯烃的加合物是已知的,制备它们的方法同样是已知的。这些加合物的技术上的缺点是它们的低的磷含量,而这例如对于阻燃而言是非常重要的。这使得使用较高浓度的加合物是必需的,并且可能对要保护免受火焰作用的对象,尤其是聚合物的根本性质产生负面的影响。
甲基亚膦酸和其酯在丙烯酸衍生物上的加合物是已知的。然而丙烯酸衍生物不是二(羧酸)酯形成剂,而是单羧酸酯形成剂。二(羧酸)酯形成剂可以通过两个羧酸基团嵌入聚合物链,单羧酸酯形成剂仅通过膦酸基团和一个羧酸基团嵌入。二羧酸连接的产物在聚合物中比仅与一个羧酸连接的那些连接得更具耐水解性。
为制备上文提到的甲基亚膦酸,在耗用卤素的方法中,通过黄磷与卤代烷的化学反应将烷基基团键合在磷原子上。这类耗用卤素的方法具有严重的缺陷,尤其因为在火灾中卤素化合物释放出毒性和腐蚀性的气体。原则上,卤素杂质在使用产品时是不利的,尤其在将产品在阻燃应用中作为合成结构单元使用时。
当作为合成结构单元使用时,由于卤素离子(特别是氯离子)的腐蚀性作用,必须使用技术上非常复杂和高成本的材料,以保证安全性。
在阻燃应用时,卤化物杂质导致许多缺陷:
在加工(阻燃热塑性聚合物模塑材料的复合、注塑)成阻燃性聚 合物成型体、聚合物膜、聚合物丝、聚合物纤维时,增加的腐蚀性可以导致生产设备的损坏。
由于腐蚀妨碍或者极大地限制了电子领域中的应用可能性。
在火灾中使用时,可以产生有损健康的和有损环境的含卤化氢的燃烧废气。
只有成功进行无卤制备,烷基亚膦酸衍生物和可形成二酯的烯烃的加合物才可以广泛地使用。
因此,本发明的目的是提供无卤的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物,且尤其是用于它们的制备的无卤素的方法,在所述方法中能够以特别简单的和经济的手段和方式,以及以相对高的产率制备所期望的加合物。目标产物是不含卤素的-与根据现有技术能够制备的那些相反。
尤其是,具有短侧链的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物根据本发明应当可再现地且以良好的产率制备。
现已令人惊讶地发现,根据本发明的加合物通过根据本发明的方法易于获得。
根据本发明的加合物相对于例如氧杂-10-磷杂菲的加合物的技术上的优点在于其更高的磷含量。因此,根据本发明的乙基亚膦酸的衣康酸加合物的磷含量相对于氧杂-10-磷杂菲的加合物的磷含量155至100。
由于根据本发明的方法是一种无卤素的方法,在根据本发明的产品中排除了上述仍含有含卤素的残基的产品的所有缺陷。
因此,本发明涉及烷基亚膦酸衍生物和可形成二酯的烯烃的加合物,它们的酸、酯和盐或其混合物。
因此,本发明的主题是加合物,其由a)和b)组成,
a)式(I)的烷基亚膦酸衍生物
A-P(=O)(OX)-H (I)
其中,
A表示任选取代的C2-C18-烷基、C2-C18-烯基、C6-C18-芳烷基、C6-C18- 芳烷基,
和
X表示H,任选取代的C1-C18-烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基、C2-C18-烯基,Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K、H和/或质子化的氮碱,和
b)式(II)的可形成二酯的烯烃
其中,
R2、R4相同或不同并表示CO2H、CO2R5、R6-CO2H、R6-CO2R5,
且
R1、R3相同或不同并表示H、R5;或者
R1、R4相同或不同并表示CO2H、CO2R5、R6-CO2H、R6-CO2R5,且R2、R3相同或不同并表示H、R5;或者
R2、R4相同或不同并表示-CO-O-CO-、-CO-S-CO-、-CO-NR1-CO-、-CO-PR1-CO-,且R1、R3相同或不同并表示H、R5;或者
R1、R2相同或不同并表示CO2H、CN、CO2R5、R6-CO2H、R6-CO2R5,且R3、R4相同或不同并表示H、R5;或者
R1、R2相同或不同并表示-CR2 3-CO-O-CO-、-CR2 3-CO-NR1-CO-、-CR2 3-CO-O-CO-CR2 3、-CR2 3-CO-NR1-CO-CR2 3,且R3、R4相同或不同并表示H、R5;或者
R2和R4各自表示-CO-CR5=CR5-CO-,且R1、R3相同或不同并表示H、R5;
R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;
R6表示C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基。
优选地,A是乙基、正丙基、异丙基、正丁基、异丁基、正戊基、异戊基、正己基、异己基、2-苯基乙基、1-苯基乙基、3-苯基丙基、2-苯基丙基、2-羟基乙基、3-羟基丙基、2-羧基乙基、3-羧基丙基、2-乙酸基乙基、3-乙酸基丙基、2-丁酸基乙基、3-丁酸基丙基、2-乙氧基乙基、3-乙氧基丙基、2-丙氧基乙基、3-丙氧基丙基、2-丁氧基乙基、3-丁氧基丙基、3-羧基丙基、2-氨基乙基和/或3-氨基丙基。
优选地,X是氢、甲基、乙基、丙基、丁基、戊基、辛基、乙基己基、乙二醇基、丙二醇基、丁二醇基、苄基、苯基、乙烯基或烯丙基,锂、钠、钾、镁、钙、钡、铝、铅、钛、铁、锌、铵、苯铵、三甲基铵、三乙基铵、三丙基铵、三丁基铵、四甲基铵、四乙基铵、四丙基铵、四丁基铵、三甲硅烷基铵或N-乙基哌啶。
优选地,可形成二酯的烯烃是马来酸、富马酸、衣康酸、苯基亚甲基丙二酸,它们的二甲酯、二乙酯、二丙酯、二异丙酯和二丁酯,马来酸酐、衣康酸酐、苯醌、萘醌或蒽醌。
本发明还涉及一种用于制备如说明书第[0018]-[0040]段中所定义的烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物的无卤素的方法,其特征在于,
a)将次膦酸源与不可形成二酯的烯烃(III)在催化剂A的存在下反应成烷基亚膦酸衍生物(I),
b)使如此获得的烷基亚膦酸衍生物(I)与可形成二酯的烯烃(I I)在催化剂B的存在下反应生成加合物,其中,烷基亚膦酸衍生物相应于式(I)
A-P(=O)(OX)-H (I)
其中,
A表示任选取代的C2-C18-烷基、C2-C18-烯基、C6-C18-芳烷基、C6-C18-芳烷基,和
X表示H,任选取代的C1-C18-烷基,C6-C18-芳基,C6-C18-芳烷基,C6-C18-烷基芳基、C2-C18-烯基,和催化剂A是过渡金属、过渡金属化合物和/或催化剂体系,其由过渡金属和/或过渡金属化合物和至少一种配体构成,和催化剂B是可形成过氧化物的化合物、过氧化合物、 偶氮化合物、碱金属、碱土金属、碱金属氢化物、碱土金属氢化物和/或碱金属醇化物、碱土金属醇化物。
优选地,A是乙基、正丙基、异丙基、正丁基、异丁基、正戊基、异戊基、正己基、异己基、2-苯基乙基、1-苯基乙基、3-苯基丙基、2-苯基丙基、2-羟基乙基、3-羟基丙基、2-羧基乙基、3-羧基丙基、2-乙酸基乙基、3-乙酸基丙基、2-丁酸基乙基、3-丁酸基丙基、2-乙氧基乙基、3-乙氧基丙基-、2-丙氧基乙基、3-丙氧基丙基、2-丁氧基乙基、3-丁氧基丙基、3-羧基丙基、2-氨基乙基和/或3-氨基丙基。
优选地,X是氢、甲基、乙基、丙基、丁基、戊基、辛基、乙基己基、乙二醇基、丙二醇基、丁二醇基、苄基、苯基、乙烯基或烯丙基,锂、钠、钾、镁、钙、钡、铝、铅、钛、铁、锌、铵、苯铵、三甲基铵、三乙基铵、三丙基铵、三丁基铵、四甲基铵、四乙基铵、四丙基铵、四丁基铵、三甲基甲硅烷基铵或N-乙基哌啶。
优选地,可形成二酯的烯烃相应于式(II)
其中,
R2、R4相同或不同并表示CO2H、CO2R5、R6-CO2H、R6-CO2R5,且R1、R3相同或不同并表示H、R5;或者
R1、R4相同或不同并表示CO2H、CO2R5、R6-CO2H、R6-CO2R5,且R2、R3相同或不同并表示H、R5;或者
R2、R4相同或不同并表示-CO-O-CO-、-CO-S-CO-、-CO-NR1-CO-、-CO-PR1-CO-,且R1、R3相同或不同并表示H、R5;或者
R1、R2相同或不同并表示CO2H、CN、CO2R5、R6-CO2H、R6-CO2R5,且R3、R4相同或不同并表示H、R5;或者
R1、R2相同或不同并表示-CR2 3-CO-O-CO-、-CR2 3-CO-NR1-CO-、-CR2 3-CO-O-CO-CR2 3、-CR2 3-CO-NR1-CO-CR2 3,且R3、R4相同或不同并表示H、R5;或者
R2和R4各自表示-CO-CR5=CR5-CO-,且R1、R3相同或不同并表示H、R5;
R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;
R6表示C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基。
优选地,可形成二酯的烯烃是马来酸、富马酸、衣康酸、苯基亚甲基丙二酸,它们的二甲酯、二乙酯、二丙酯、二异丙酯和二丁酯,苯醌、萘醌或蒽醌。
优选地,次膦酸源是次膦酸、次膦酸的盐、次膦酸的酯或它们的混合物。
优选地,不可形成二酯的烯烃相应于通式(III)
其中,R7至R10相同或不同,且表示C1-C18烷基、C6-C18-芳基或C2-C18烯基。
优选地,不可形成二酯的烯烃(III)是乙烯、1-丙烯、1-丁烯、1-戊烯、1-己烯和/或1,3-丁二烯。
优选地,过渡金属和/或过渡金属化合物是源自第七和第八副族的那些。
优选地,过渡金属和/或过渡金属化合物是铑、镍、钯、钌和/或铂。
优选地,催化剂B是过氧化氢、过氧化钠、过氧化锂、过硫酸钾、过硫酸钠、过硫酸铵、过二硫酸钠、过硼酸钾、过氧乙酸、过氧化苯甲酰、二叔丁基过氧化物、和/或过二硫酸,和/或是偶氮二异丁腈、2,2′-偶氮双(2-脒基丙烷)-二盐酸盐和/或2,2′-偶氮双(N,N′-二亚甲基-异丁酰脒)-二盐酸盐,和/或是锂、氢化锂、氢化铝锂、甲基锂、丁基锂、叔丁基锂、二异丙基氨基锂、钠、氢化钠、硼氢化钠、甲醇钠、乙醇钠或丁醇钠、甲醇钾、乙醇钾和/或丁醇钾。
优选地,将步骤b)之后由烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)获得的反应产物在步骤c)中与成酯剂反应。
优选地,成酯剂是C1-C20饱和的和不饱和的一元、二元、三元和四元醇。
优选地,成酯剂是甲醇、乙醇、丙醇、丁醇、戊醇、辛醇、乙二醇、聚乙二醇、1,2-丙二醇、1,3-丙二醇、丁二醇、甘油、赤藓糖醇、季戊四醇、烯丙醇、3-丁烯-1-醇、3-羟基-1-丁烯、3-丁烯-2-醇、甲基乙烯基甲醇、2-甲基-2-丙烯-1-醇、甲基烯丙醇、2-丁烯-1-醇、巴豆醇、1-戊烯-3-醇、反-2-戊烯-1-醇、顺-2-戊烯-1-醇、3-戊烯-2-醇、4-戊烯-1-醇、4-戊烯-2-醇、1-己烯-3-醇、顺-2-己烯-1-醇、反-2-己烯-1-醇、顺-3-己烯-1-醇、反-3-己烯-1-醇、4-己烯-1-醇、5-己烯-1-醇、5-己烯-2-醇、1-庚烯-3-醇、1-辛烯-3-醇、反-2-辛烯-1-醇、油醇、萜烯醇、炔丙醇和/或2-丁炔-1,4-二醇。
优选地,将步骤b)之后由烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)获得的反应产物与催化剂C反应,在此将反应产物皂化。
优选地,催化剂C是酸、碱、水、无机酸、磺酸、碱金属氢氧化物和/或碱土金属氢氧化物。
本发明还涉及如说明书第[0018]-[0040]段中所定义的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)形成的加合物作为用于进一步合成的中间体,作为粘结剂,作为在环氧树脂、聚氨酯和不饱和聚酯树脂的固化中的交联剂或促进剂,作为聚合物稳定剂,作为植物保护剂,作为用于人和动物的治疗剂或治疗剂中的添加剂,作为螯合剂,作为矿物油添加剂,作为抗蚀剂,在洗涤剂和清洁剂应用中以及在电子应用中的用途。
此外,本发明涉及如说明书第[0018]-[0040]段中所定义的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)形成的加合物作为阻燃剂,尤其是用于透明漆和发泡型防火涂料的阻燃剂、用于木材和其它含纤维素产品的阻燃剂;作为聚合物的反应性和/或非反应性阻燃剂;用于制备阻燃聚合物模塑材料;用于制备阻燃聚合物成型体和/或用于通过浸渍为聚酯和纤维素纯织物和混纺织物进行阻燃性整理的用途。
本发明还涉及阻燃热塑性或热固性聚合物模塑材料,其含有0.5至45重量%的如说明书第[0018]-[0040]段中所定义的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)形成的加合物,0.5至99重量%的热塑性或热固性聚合物或它们的混合物,0至55重量%的添加剂和0至55重量%的填料或增强材料,其中,各组分之和为100重量%。
最后,本发明涉及阻燃热塑性或热固性聚合物成型体、聚合物膜、聚合物丝和聚合物纤维,其含有0.5至45重量%的如说明书第[0018]-[0040]段中所定义的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)形成的加合物,0.5至99重量%的热塑性或热固性聚合物或它们的混合物,0至55重量%的添加剂和0至55重量%的填料或增强材料,其中,各组分之和为100重量%。
根据本发明的方法,可以
a)使次膦酸源与不可形成二酯的烯烃(III)在催化剂A的存在下反应成烷基亚膦酸衍生物(I),
b)使如此获得的烷基亚膦酸衍生物(I)与可形成二酯的烯烃(II)任选地在催化剂B的存在下反应。
在根据本发明的方法的另一实施方式中,可以
a)使次膦酸源与不可形成二酯的烯烃(III)在催化剂A的存在下反应成烷基亚膦酸衍生物(I),
b)使如此获得的烷基亚膦酸衍生物(I)与可形成二酯的烯烃(II)任选地在催化剂B的存在下反应,和
c)然后与成酯剂反应。
以后将这种方法称为方法2。
在根据本发明的方法的再一实施方式中,可以
a)使次膦酸源与不可形成二酯的烯烃(III)在催化剂A的存在下反应成烷基亚膦酸衍生物(I),
b)使如此获得的烷基亚膦酸衍生物(I)与可形成二酯的烯烃(II)任选地在催化剂B的存在下反应,和
c)然后与催化剂C反应,其中将来自步骤b)的产物酯化。
以后将这种方法称为方法3。
优选地,在上述根据本发明的无卤素的方法结束时,可以将获得的烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物、其酸、盐或酯随后与Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、K的金属化合物和/或质子化的氮碱反应成这些金属和/或含氮化合物相应的烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物。
烷基亚膦酸酯优选是烷基酯、羟烷基酯、烷芳基酯、芳基酯和/或烯基酯。
在此,特别优选是甲酯、乙酯、丙酯、丁酯、戊酯、辛酯、乙基己酯、乙二醇酯、丙二醇酯、丁二醇酯、苄酯、苯酯、乙烯酯和/或烯丙酯。
可使用的可形成二酯的烯烃(II)是这种类型的:
其中R2、R4相同或不同,且表示CO2H、CO2R5、R6-CO2H、R6-CO2R5;R1、R3相同或不同,表示H、R5;R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;R6表示C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基。
优选地,R1、R4相同或不同,表示CO2H、CO2R5、R6-CO2H、R6-CO2R5;R2、R3相同或不同,表示H、R5;R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;R6表示C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基。
优选地,R2、R4相同或不同,表示-CO-O-CO-、-CO-S-CO-、-CO-NR1-CO-、-CO-PR1-CO-;R1、R3相同或不同,表示H、R5;R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基。
优选地,R1、R2也是相同的或不同的,表示CO2H、CN、CO2R5、R6-CO2H、 R6-CO2R5;R3、R4相同或不同,表示H、R5;R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;R6表示C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基。
优选地,R1、R2相同或不同,表示-CR2 3-CO-O-CO-、-CR2 3-CO-NR1-CO-、-CR2 3-CO-O-CO-CR2 3、-CR2 3-CO-NR1-CO-CR2 3,R3、R4相同或不同,表示H、R5;R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;
优选地,R2=R4,均表示-CO-CR5=CR5-CO-;R1、R3相同或不同且表示H、R5;R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基。
优选地,可形成二酯的烯烃(II)既可以以中间体制备(“原位”),也可以在其形成期间与烷基亚膦酸衍生物反应。
根据本发明的无卤素的方法的步骤a)的特征可在于,
a)将次膦酸源与不可形成二酯的烯烃(III)在催化剂A或者催化剂体系A的存在下反应,
b)任选除去溶剂和/或烯烃,
c)除去催化剂A,催化剂体系A,过渡金属和/或过渡金属化合物,
d)除去配体和/或络合剂,
e)除去助剂和/或烯烃。
根据本发明的无卤素的方法的步骤a)的特征可在于,将次膦酸源与烯烃在催化剂A的存在下反应,并滤除不溶性产物。
根据本发明的无卤素的方法的步骤a)的特征还可在于,
a)将次膦酸源与不可形成二酯的烯烃(III)在催化剂A的存在下反应,
b)任选滤除催化剂A,
c)除去配体和/或络合剂,
d)除去溶剂,
e)任选将除去的催化剂或配体和/或络合剂的至少90%回收到步骤a)中。
特别优选地,烯烃(III)的R7、R8、R9、R10相同或不同,且彼此独立地表示H、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和/或苯基。
优选地,还使用官能化的烯烃,诸如异硫氰酸烯丙酯、甲基丙烯酸烯丙酯、2-烯丙基苯酚、N-烯丙基硫脲、2-(烯丙基硫基)-2-噻唑啉、烯丙基三甲基硅烷、乙酸烯丙酯、乙酰乙酸烯丙酯、烯丙醇、烯丙胺、烯丙基苯、烯丙基腈、氰乙酸烯丙酯、烯丙基茴香醚、反-2-戊烯醛、顺-2-戊烯腈、1-戊烯-3-醇、4-戊烯-1-醇、4-戊烯-2-醇、反-2-己烯醛、反-2-己烯-1-醇、顺-3-己烯-1-醇、5-己烯-1-醇、苯乙烯、-甲基苯乙烯、4-甲基苯乙烯、乙酸乙烯酯、9-乙烯基蒽、2-乙烯基吡啶、4-乙烯基吡啶和1-乙烯基-2-吡咯烷酮。
特别优选地,烯烃是乙烯、1-丙烯、1-丁烯、1-戊烯、1-己烯和/或1,3-丁二烯。
优选地,用于催化剂A的过渡金属优选是第七和第八副族(按照新命名法为第7、8、9或10族的金属)的元素,诸如铼、钌、钴、铑、铱、镍、钯和铂。
优选地,作为过渡金属和过渡金属化合物来源使用其金属盐。合适的盐是无机酸的那些,其含有氟化物、氯化物、溴化物、碘化物、氟酸盐、氯酸盐、溴酸盐、碘酸盐、亚氟酸盐、亚氯酸盐、亚溴酸盐、亚碘酸盐、次氟酸盐、次氯酸盐、次溴酸盐、次碘酸盐、高氟酸盐、高氯酸盐、高溴酸盐、高碘酸盐、氰化物、氰酸盐、硝酸盐、氮化物、亚硝酸盐、氧化物、氢氧化物、硼酸盐、硫酸盐、亚硫酸盐、硫化物、过硫酸盐、硫代硫酸盐、氨基磺酸盐、磷酸盐、亚磷酸盐、次磷酸盐、磷化物、碳酸盐和磺酸盐(例如甲磺酸盐、氯磺酸盐、氟磺酸盐、三氟甲磺酸盐、苯磺酸盐、萘磺酸盐、甲苯磺酸盐、叔丁基磺酸盐、2-羟基丙磺酸盐和磺化离子交换树脂)的阴离子;和/或其含有有机盐,诸如乙酰丙酮盐和具有最多20个碳原子的羧酸盐,例如甲酸盐、乙酸盐、丙酸盐、丁酸盐、草酸盐、硬脂酸盐和柠檬酸盐,以及具有最多20个碳原子的卤代羧酸盐,例如三氟乙酸盐、三氯乙酸盐的阴离子。
过渡金属和过渡金属化合物的另一来源是过渡金属与四苯基硼酸阴离子和卤代四苯基硼酸阴离子的盐,诸如全氟苯基硼酸盐。
合适的盐同样包括复盐和络盐,其由一种或多种过渡金属离子,和彼此独立的一种或多种碱金属离子、碱土金属离子、铵离子、有机铵离子、鏻离子和有机鏻离子,和彼此独立的一种或多种上述阴离子构成。合适的复盐例如是六氯钯酸铵和四氯钯酸铵。
优选地,过渡金属的来源是元素态的过渡金属和/或处于其零价状态的过渡金属化合物。
优选地,以金属态使用或者以与其它金属的合金的形式使用过渡金属,这其中优选硼、锆、钽、钨、铼、钴、铱、镍、钯、铂和/或金。在所用的合金中,过渡金属含量优选为45-99.95重量%。
优选以微分散形式(0.1mm-100μm的粒度)使用过渡金属。
优选地,过渡金属以负载在金属氧化物(例如氧化铝、二氧化硅、二氧化钛、二氧化锆、氧化锌、氧化镍、氧化钒、氧化铬、氧化镁、Celite、硅藻土)上,负载在金属碳酸盐(例如碳酸钡、碳酸钙、碳酸锶)上,负载在金属硫酸盐(例如硫酸钡、硫酸钙、硫酸锶)上,负载在金属磷酸盐(例如磷酸铝、磷酸钒)上,负载在金属碳化物(例如碳化硅)上,负载在金属铝酸盐(例如铝酸钙)上,负载在金属硅酸盐(例如硅酸铝、白垩、沸石、膨润土、蒙脱石、锂蒙脱石)上,负载在官能化硅酸盐、官能化硅胶(例如SiliaBond、QuadraSilTM)上,负载在官能化聚硅氧烷(例如Deloxan)上,负载在金属氮化物上,负载在炭、活性炭、莫来石、铝土矿、辉锑矿、白钨矿、钙钛矿、水滑石、杂多阴离子上,负载在官能化和未官能化的纤维素、壳聚糖、角蛋白、杂多阴离子上,负载在离子交换剂(例如AmberliteTM、AmberjetTM、AmbersepTM、Dowex、Lewatit、ScavNet)上,负载在官能化聚合物(例如Chelex、QuadraPureTM、Smopex、PolyOrgs)上,负载在聚合物键合的磷烷、磷烷氧化物、次膦酸盐、膦酸盐、磷酸盐、胺、铵盐、酰胺、硫代酰胺、脲、硫脲、三嗪、咪唑、吡唑、吡啶、嘧啶、吡嗪、硫醇、硫醚、硫醇酯、醇、烷氧化物、醚、酯、 羧酸、乙酸酯、缩醛、肽、杂芳烯、聚乙烯亚胺/二氧化硅和/或树状大分子上的形式使用。
合适的金属盐和/或过渡金属的来源优选同样是其络合物。金属盐和/或过渡金属的络合物由金属盐或者过渡金属和一种或多种络合剂构成。合适的络合剂例如是烯烃、二烯烃、腈、二腈、一氧化碳、膦、二膦、亚磷酸酯、二亚磷酸酯、二亚苄基丙酮、环戊二烯、茚或苯乙烯。合适的金属盐和/或过渡金属的络合物可以负载在上述载体材料上。
优选地,上述负载的过渡金属的含量是0.01至20重量%,更优选0.1至10重量%,尤其是0.2至5重量%,基于载体材料的总质量计。
合适的过渡金属和过渡金属化合物的来源例如是钯、铂、镍、铑;负载在氧化铝、氧化硅、碳酸钡、硫酸钡、碳酸钙、碳酸锶、炭、活性炭上的钯、铂、镍、铑;铂-钯-金合金、铝-镍合金、铁-镍合金、镧系-镍合金、锆-镍合金、铂-铱合金、铂-铑合金;Raney镍、镍-锌-铁氧化物;钯(II)、镍(II)、铂(II)、铑的氯化物、溴化物、碘化物、氟化物、氢化物、氧化物、过氧化物、氰化物、硫酸盐、硝酸盐、磷化物、硼化物、铬氧化物、钴氧化物、碱式碳酸盐、环己烷丁酸盐、氢氧化物、钼酸盐、辛酸盐、草酸盐、高氯酸盐、酞菁化物、5,9,14,18,23,27,32,36-八丁氧基-2,3-萘酞菁化物、磺酸盐、高氯酸盐、硫氰酸盐、双(2,2,6,6-四甲基-3,5-庚二酮酸盐)、丙酸盐、乙酸盐、硬脂酸盐、2-乙基己酸盐、乙酰丙酮化物、六氟乙酰丙酮化物、四氟硼酸盐、硫代硫酸盐、三氟乙酸盐、酞菁四磺酸四钠盐、甲基化物、环戊二烯化物、甲基环戊二烯化物、乙基环戊二烯化物、五甲基环戊二烯化物、2,3,7,8,12,13,17,18-八乙基-21H,23H-卟吩化物、5,10,15,20-四苯基-21H,23H-卟吩化物、双(5-[[4-(二甲氨基)苯基]亚氨基]-8(5H)-喹啉酮)化物、2,11,20,29-四叔丁基-2,3-萘酞菁化物、2,9,16,23-四苯氧基-29H,31H-酞菁化物、5,10,15,20-四(五氟苯基)-21H,23H-卟吩化物,和它们的1,4-双(二苯基膦)丁烷络合物、 1,3-双(二苯基膦)丙烷络合物、2-(2′-二叔丁基膦)联苯络合物、乙腈络合物、苯甲腈络合物、乙二胺络合物、氯仿络合物、1,2-双(苯亚磺酰)乙烷络合物、(1,3-双(2,6-二异丙基苯基)咪唑啉)(3-氯吡啶)络合物、2′-(二甲氨基)-2-联苯基络合物、二降冰片基膦络合物、2-(二甲氨基甲基)二茂铁络合物、烯丙基络合物、双(二苯基膦)丁烷络合物、(N-琥珀酰亚胺基)双(三苯基膦)络合物、二甲基苯基膦络合物、甲基二苯基膦络合物、1,10-菲咯啉络合物、1,5-环辛二烯络合物、N,N,N′,N′-四甲基乙二胺络合物、三苯基膦络合物、三邻甲苯基膦络合物、三环己基膦络合物、三丁基膦络合物、三乙基膦络合物、2,2′-双(二苯基膦)-1,1′-联萘络合物、1,3-双(2,6-二异丙基苯基)咪唑-2-亚基络合物、1,3-双(均三甲苯基)咪唑-2-亚基络合物、1,1′-双(二苯基膦)二茂铁络合物、1,2-双(二苯基膦)乙烷络合物、N-甲基咪唑络合物、2,2′-联吡啶络合物、(双环[2.2.1]-庚-2,5-二烯)络合物、双(二叔丁基(4-二甲氨基苯基)膦)络合物、双(叔丁基异氰酸酯)络合物、二乙二醇二甲醚络合物、乙二醇二甲醚络合物、1,2-二甲氧基乙烷络合物、双(1,3-二氨基-2-丙醇)络合物、双(N,N-二乙基乙二胺)络合物、1,2-二氨基环己烷络合物、吡啶络合物、2,2′:6′,2″-三联吡啶络合物、乙硫醚络合物、乙烯络合物、胺络合物;六氯钯(IV)酸钾、六氯钯(IV)酸钠、六氯钯(IV)酸铵、四氯钯(II)酸钾、四氯钯(II)酸钠、四氯钯(II)酸铵、三叔丁基膦溴化钯(I)二聚体、(2-甲基烯丙基)氯化钯(II)二聚体、双(二亚苄基丙酮)钯(0)、三(二亚苄基丙酮)二钯(0)、四(三苯基膦)钯(0)、四(三环己基膦)钯(0)、双[1,2-双(二苯基膦)乙烷]钯(0)、双(3,5,3′,5′-二甲氧基亚苄基丙酮)钯(0)、双(三叔丁基膦)钯(0)、内消旋四苯基四苯并卟吩钯、四(甲基二苯基膦)钯(0)、三(3,3′,3″-次膦基-三(苯磺酸)钯(0)九钠盐、1,3-双(2,4,6-三甲基苯基)-咪唑-2-亚基(1,4-萘醌)钯(0)、1,3-双(2,6-二异丙基苯基)-咪唑-2-亚基(1,4-萘醌)钯(0)、和它们的氯仿络合物;
烯丙基氯化镍(II)二聚体、硫酸镍(II)铵、双(1,5-环辛二烯)镍(0)、双(三苯基膦)二羰基镍(0)、四(三苯基膦)镍(0)、四(三苯基 亚磷酸)镍(0)、六氟镍(IV)酸钾、四氰基镍(II)酸钾、仲高碘酸镍(IV)钾、四溴镍(II)酸二锂,四氰基镍(II)酸钾;
氯化铂(IV)、氧化铂(IV)、硫化铂(IV)、六氯合铂(IV)酸钾、六氯合铂(IV)酸钠、六氯合铂(IV)酸铵、四氯合铂(II)酸钾、四氯合铂(II)酸铵、四氰基铂(II)酸钾、三甲基(甲基环戊二烯基)铂(IV)、顺-二胺四氯合铂(IV)、三氯(乙烯基)铂(II)酸钾、六羟基铂(IV)酸钠、四氨基铂(II)合四氯化铂(II)、六氯合铂(IV)酸四丁基铵、乙烯双(三苯基膦)铂(0)、铂(0)-1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷、铂(0)-2,4,6,8-四甲基-2,4,6,8-四乙烯基环四硅氧烷、四(三苯基膦)铂(0)、八乙基卟吩铂、氯铂酸、羰基铂;氯代双(乙烯)铑二聚体、六癸酰六铑、(1,5-环辛二烯)氯铑二聚体、(降冰片二烯)氯铑二聚体、(1,5-己二烯)氯铑二聚体。
配体优选是式(IV)的膦
PR11 3 (IV)
式中,基团R11彼此独立地表示氢,直链、支链或环状的C1-C20烷基,C6-C20烷基芳基,C2-C20烯基,C2-C20炔基,C1-C20羧酸酯基,C1-C20烷氧基,C2-C20烯基氧基,C2-C20炔基氧基,C2-C20烷氧羰基,C1-C20烷硫基,C1-C20烷基磺酰基,C1-C20烷基亚磺酰基,甲硅烷基和/或其衍生物,和/或被至少一个R12取代的苯基或被至少一个R12取代的萘基。R12彼此独立地表示氢,氟,氯,溴,碘,NH2,硝基,羟基,氰基,甲酰基,直链、支链或环状的C1-C20烷基,C1-C20烷氧基,HN(C1-C20烷基),N(C1-C20烷基)2,-CO2-(C1-C20烷基),-CON(C1-C20烷基)2,-OCO(C1-C20烷基),NHCO(C1-C20烷基),C1-C20酰基,-SO3M,-SO2N(R13)M,-CO2M,-PO3M2,-AsO3M2,-SiO2M,-C(CF3)2OM(M=H、Li、Na或K),其中R13表示氢,氟,氯,溴,碘,直链、支链或环状的C1-C20烷基,C2-C20烯基,C2-C20炔基,C1-C20羧酸酯基,C1-C20烷氧基,C2-C20烯基氧基,C2-C20炔基氧基,C2-C20烷氧羰基,C1-C20烷硫基,C1-C20烷基磺酰基,C1-C20烷基亚磺酰基,甲硅烷基和/或其衍生物,芳基,C6-C20芳烷基,C6-C20烷基芳基,苯基和/或联苯基。优选所有R11基团是相同的。
合适的膦(IV)例如是三甲基膦、三乙基膦、三丙基膦、三异丙基膦、三丁基膦、三异丁基膦、三异戊基膦、三己基膦、三环己基膦、三辛基膦、三癸基膦、三苯基膦、二苯基甲基膦、苯基二甲基膦、三(邻甲苯基)膦、三(对甲苯基)膦、乙基二苯基膦、二环己基苯基膦、2-吡啶基二苯基膦、双(6-甲基-2-吡啶基)苯基膦、三(对氯苯基)膦、三(对甲氧基苯基)膦、二苯基(2-磺酸基苯基)膦;二苯基(3-磺酸基苯基)膦的钾、钠、铵盐,双(4,6-二甲基-3-磺酸基苯基)(2,4-二甲基苯基)膦的钾、钠、铵盐,双(3-磺酸基苯基)苯基膦的钾、钠、铵盐,三(4,6-二甲基-3-磺酸基苯基)膦的钾、钠、铵盐,三(2-磺酸基苯基)膦的钾、钠、铵盐,三(3-磺酸基苯基)膦的钾、钠、铵盐;2-双(二苯基膦乙基)三甲基碘化铵,2′-二环己基膦-2,6-二甲氧基-3-磺酸基-1,1′-联苯钠盐,亚磷酸三甲酯和/或亚磷酸三苯酯。
配体特别优选是如下通式的双齿配体
R11M″-Z-M″R11 (V)。
式中,M″彼此独立地代表N、P、As或Sb。两个M″优选是相同的,并且特别优选M″表示磷原子。
每个R11基团彼此独立地代表式(VI)所描述的基团。优选所有R11基团是相同的。
Z优选是二价的桥联基团,其含有至少1个桥原子,优选含有2至6个桥原子。
桥原子可以选自C原子、N原子、O原子、Si原子和S原子。Z优选是含有至少一个碳原子的有机桥联基团。Z优选是含有1至6个桥原子的有机桥联基团,其中至少两个是碳原子,所述碳原子可以是未取代的或取代的。
基团Z优选是-CH2-、-CH2-CH2-、-CH2-CH2-CH2-、-CH2-CH(CH3)-CH2-、-CH2-C(CH3)2-CH2-、-CH2-C(C2H5)-CH2-、-CH2-Si(CH3)2-CH2-、-CH2-O-CH2-、-CH2-CH2-CH2-CH2-、-CH2-CH(C2H5)-CH2-、-CH2-CH(n-Pr)-CH和-CH2-CH(n-Bu)-CH2-,未取代或取代的1,2-苯基、1,2-环己基、1,1′-二茂铁基或1,2-二茂铁基、2,2′-(1,1′-联苯基)-、4,5-呫吨基和/或 氧二-2,1-亚苯基。
合适的双齿膦配体(V)例如是1,2-双(二甲基膦基)乙烷、1,2-双(二乙基膦基)乙烷、1,2-双(二丙基膦基)乙烷、1,2-双(二异丙基膦基)乙烷、1,2-双(二丁基膦基)乙烷、1,2-双(二叔丁基膦基)乙烷、1,2-双(二环己基膦基)乙烷和1,2-双(二苯基膦基)乙烷;1,3-双(二环己基膦基)丙烷、1,3-双(二异丙基膦基)丙烷、1,3-双(二叔丁基膦基)丙烷和1,3-双(二苯基膦基)丙烷;1,4-双(二异丙基膦基)丁烷和1,4-双(二苯基膦基)丁烷;1,5-双(二环己基膦基)戊烷;1,2-双(二叔丁基膦基)苯、1,2-双(二苯基膦基)苯、1,2-双(二环己基膦基)苯、1,2-双(二环戊基膦基)苯、1,3-双(二叔丁基膦基)苯、1,3-双(二苯基膦基)苯、1,3-双(二环己基膦基)苯和1,3-双(二环戊基膦基)苯;9,9-二甲基-4,5-双(二苯基膦基)呫吨、9,9-二甲基-4,5-双(二苯基膦基)-2,7-二叔丁基呫吨、9,9-二甲基-4,5-双(二叔丁基膦基)呫吨、1,1′-双(二苯基膦基)二茂铁、2,2′-双(二苯基膦基)-1,1′-联萘、2,2′-双(二对甲苯基膦基)-1,1′-联萘、(氧二-2,1-亚苯基)双(二苯基膦)、2,5-(二异丙基磷杂环戊烷基)苯、2,3-O-异丙叉基-2,3-二羟基-1,4-双(二苯基膦基)丁烷、2,2′-双(二叔丁基膦基)-1,1′-联苯、2,2′-双(二环己基膦基)-1,1′-联苯、2,2′-双(二苯基膦基)-1,1′-联苯、2-(二叔丁基膦基)-2′-(N,N-二甲氨基)联苯、2-(二环己基膦基)-2′-(N,N-二甲氨基)联苯、2-(二苯基膦基)-2′-(N,N-二甲氨基)联苯、2-(二苯基膦基)乙胺、2-[2-(二苯基膦基)乙基]吡啶;1,2-双(二-4-磺酸基苯基膦基)苯的钾、钠、铵盐,(2,2′-双[[双(3-磺酸基苯基)膦基]甲基]-4,4′,7,7′-四磺酸基-1,1′-联萘的钾、钠、铵盐,(2,2′-双[[双(3-磺酸基苯基)膦基]甲基]-5,5′-四磺酸基-1,1′-联苯的钾、钠、铵盐,(2,2′-双[[双(3-磺酸基苯基)膦基]甲基]-1,1′-联萘的钾、钠、铵盐,(2,2′-双[[双(3-磺酸基苯基)膦基]甲基]-1,1′-联苯的钾、钠、铵盐,9,9-二甲基-4,5-双(二苯基膦基)-2,7-磺酸基呫吨的钾、钠、铵盐,9,9-二甲基-4,5-双(二叔丁基膦基)-2,7-磺酸基呫吨的钾、钠、铵盐,1,2-双(二-4-磺酸基苯基膦基)苯的钾、钠、铵盐,内消旋-四(4-磺酸基苯 基)卟吩的钾、钠、铵盐,内消旋-四(2,6-二氯-3-磺酸基苯基)卟吩的钾、钠、铵盐,内消旋-四(3-磺酸基均三甲苯基)卟吩的钾、钠、铵盐,四(4-羧基苯基)卟吩的钾、钠、铵盐和5,11,17,23-磺酸基-25,26,27,28-四羟基杯[4]芳烃的钾、钠、铵盐。
此外,式(IV)和(V)的配体可以通过基团R11和/或桥联基团键合至合适的聚合物或无机基底。
催化剂体系具有1∶0.01至1∶100,优选1∶0.05至1∶10,且尤其是1∶1至1∶4的过渡金属-配体摩尔比。
优选地,方法步骤a)、b)和c)中的反应可选地在气氛中进行,所述气氛含有另外的气体成分,例如氮气、氧气、氩气、二氧化碳;温度为-20至340℃,尤其是20至180℃,且总压力为1至100巴。
在方法步骤a)、b)和c)之后,产物和/或成分和/或过渡金属和/或过渡金属化合物和/或催化剂体系和/或配体和/或反应物的分离可选地通过蒸馏或精馏、结晶或沉淀、过滤或离心、吸附或色谱法或者其它已知的方法来进行。
根据本发明,溶剂、助剂和任选的其它挥发性成分通过例如蒸馏、过滤和/或萃取而除去。
优选地,方法步骤a)、b)和c)中的反应可选地在吸收塔、喷塔、泡柱、搅拌釜、喷淋床发生器、流管、环管反应器和/或捏合机中进行。
合适的混合设备例如是锚式、桨式、MIG、螺旋桨、叶轮、涡轮、十字搅拌器,分散盘,空化(气化)搅拌器,转子-定子混合器,静态混合器,文丘里喷嘴和/或气密电动泵。
优选地,反应溶液/混合物在此经历这样的混合强度,其相当于旋转雷诺数为1至1,000,000,优选100至100,000。
优选地,各反应物料的强效搅拌在供能为0.080至10kW/m3,优选0.30至1.65kW/m3的条件下进行。
优选地,在反应期间,各催化剂A以均相地和/或非均相形式发挥作用。因此,以非均相作用的催化剂在反应期间总以悬浮形式起作用或者结合至固相的形式发挥作用。
优选地,催化剂A在反应之前和/或反应开始时和/或在反应期间原位生成。
优选地,各反应在作为单相体系的溶剂中,在均相或非均相的混合物中和/或在气相中进行。
采用多相体系时可以附加使用相转移催化剂。
根据本发明的反应可以在液相中、在气相中或在超临界相中进行。在此,催化剂A处于液体状态时优选以均相形式或作为悬浮液使用,而处于气相或超临界操作方式的情况下,固定床设备是有利的。
合适的溶剂是水;醇,例如甲醇、乙醇、异丙醇、正丙醇、正丁醇、异丁醇、叔丁醇、正戊醇、异戊醇、叔戊醇、正己醇、正辛醇、异辛醇、正十三烷醇、苯甲醇等。进一步优选是二醇,例如乙二醇、1,2-丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、二乙二醇等;脂肪烃,例如戊烷、己烷、庚烷、辛烷和石油醚、石油精、煤油、石油、石蜡油等;芳香烃,例如苯、甲苯、二甲苯、均三甲苯、乙苯、二乙基苯等;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷、氯苯、四氯化碳、四溴乙烯等;脂环烃,例如环戊烷、环己烷和甲基环己烷等;醚,例如茴香醚(甲基苯基醚)、叔丁基甲基醚、二苄醚、乙醚、二氧六环、二苯醚、甲基乙烯基醚、四氢呋喃、三异丙基醚等;二醇醚,例如二乙二醇二乙醚、二乙二醇二甲醚(二甘醇二甲醚)、二乙二醇单丁醚、二乙二醇单甲醚、1,2-二甲氧基乙烷(DME,单甘醇二甲醚)、乙二醇单丁醚、三乙二醇二甲醚(三甘醇二甲醚)、三乙二醇单甲醚等;酮,例如丙酮、二异丁酮、甲基正丙基酮、甲基乙基酮、甲基异丁基酮等;酯,例如甲酸甲酯、乙酸甲酯、乙酸乙酯、乙酸正丙酯和乙酸正丁酯等;羧酸,例如甲酸、乙酸、丙酸、丁酸等;单独或彼此组合使用。
合适的溶剂还有所使用的烯烃和次膦酸源。这对于获得较高的空-时产率是有利的。
优选地,反应在烯烃和/或溶剂自身的蒸汽压下进行。
优选地,反应在0.01至100巴的烯烃分压下,特别优选在0.1 至10巴的烯烃分压下进行。
优选地,反应以1∶10,000至1∶0.001的次膦酸-烯烃摩尔比,特别优选以1∶30至1∶0.01的比例进行。
优选地,反应以1∶1至1∶0.00000001的次膦酸-催化剂摩尔比,特别优选在1∶0.01至1∶0.000001下进行。
优选地,反应以1∶10,000至1∶0的次膦酸-溶剂摩尔比,特别优选在1∶50至1∶1下进行。
一种根据本发明的用于制备烷基亚膦酸和其衍生物(I)的方法的特征在于,将次膦酸源与烯烃在催化剂存在下反应并将产物(I)(烷基亚膦酸或烷基亚膦酸盐、烷基亚膦酸酯)从催化剂、过渡金属或过渡金属化合物、配体、络合剂、盐和副产物中分离。
根据本发明,催化剂、催化剂体系、过渡金属和/或过渡金属化合物通过加入助剂1分离,并通过萃取和/或过滤除去催化剂、催化剂体系、过渡金属和/或过渡金属化合物。
根据本发明,配体和/或络合剂通过用助剂2萃取和/或用助剂2蒸馏而分离。
助剂1优选是水和/或至少一个金属捕捉剂(金属清除剂)家族的成员。优选的金属捕捉剂是金属氧化物,诸如氧化铝、二氧化硅、二氧化钛、二氧化锆、氧化锌、氧化镍、氧化钒、氧化铬、氧化镁、Celite 、硅藻土;金属碳酸盐,诸如碳酸钡、碳酸钙、碳酸锶;金属硫酸盐,诸如硫酸钡、硫酸钙、硫酸锶;金属磷酸盐,诸如磷酸铝、磷酸钒;金属碳化物,诸如碳化硅;金属铝酸盐,诸如铝酸钙;金属硅酸盐,诸如硅酸铝、白垩、沸石、膨润土、蒙脱石、锂蒙脱石;官能化的硅酸盐、官能化的硅胶,诸如SiliaBond、QuadraSilTM;官能化的聚硅氧烷,诸如Deloxan ;金属氮化物;炭;活性炭;莫来石;铝矾土;辉锑矿;白钨矿;钙钛矿;水滑石;官能化和未官能化的纤维素、壳聚糖、角蛋白、杂多阴离子;离子交换剂,诸如AmberliteTM、AmberjetTM、AmbersepTM、Dowex、Lewatit、ScavNet;官能化的聚合物,诸如Chelex、QuadraPureTM、Smopex、PolyOrgs;聚合物键合的磷烷、 磷烷氧化物、次膦酸盐、膦酸盐、磷酸盐、胺、铵盐、酰胺、硫代酰胺、脲、硫脲、三嗪、咪唑、吡唑、吡啶、嘧啶、吡嗪、硫醇、硫醚、硫醇酯、醇、烷氧化物、醚、酯、羧酸、乙酸酯、缩醛、肽、杂芳烯、聚乙烯亚胺/二氧化硅和/或树状大分子。
优选地,助剂1以这样的量添加,该量相当于在助剂1上0.1-40重量%的金属负载量。
优选地,助剂1在温度20-90℃下使用。
优选地,助剂1的停留时间为0.5-360分钟。
助剂2优选为上述的根据本发明的溶剂,如优选在方法步骤a)中使用。
优选地,在根据本发明的方法中,步骤b)在添加催化剂B下进行。优选的是 酸、碱、自由基引发剂和光引发剂。
优选的碱是有机碱和/或金属有机碱。
优选的金属有机碱是第一和第二主族和第四副族的醇盐。特别优选是甲醇钠、乙醇钠、丁醇钠、甲醇钾、乙醇钾、丁醇钾、钛(IV)酸丙酯和/或钛(IV)酸丁酯。
优选的催化剂B还有金属,金属氢化物,例如锂、氢化锂、氢化铝锂、甲基锂、丁基锂、叔丁基锂、二异丙基氨基锂、钠、氢化钠、硼氢化钠。
优选的用于步骤b)的自由基引发剂是过氧化合物,诸如过一硫酸、过硫酸钾(过一硫酸钾)、CaroatTM、OxoneTM、过二硫酸、过硫酸钾(过二硫酸钾)、过硫酸钠(过二硫酸钠)、过硫酸铵(过二硫酸铵)。
特别优选的是在步骤b)的溶剂体系中可以形成过氧化物的化合物,诸如过氧化钠、过氧化钠二过氧化氢合物、过氧化钠二过氧化氢水合物、过氧化钠二水合物、过氧化钠八水合物、过氧化锂、过氧化锂单过氧化氢三水合物、过氧化钙、过氧化锶、过氧化钡、过氧化镁、过氧化锌、超氧化钾、超氧化钾二过氧化氢合物、过硼酸钠四水合物、过硼酸钠三水合物、过硼酸钠一水合物、无水过硼酸钠、过硼酸钾过 氧化氢合物、过硼酸镁、过硼酸钙、过硼酸钡、过硼酸锶、过硼酸钾、过一磷酸、过氧焦磷酸、过氧焦磷酸钾、过氧焦磷酸铵、过氧焦磷酸钾铵(复盐)、碳酸钠过氧化氢合物、过氧化氢脲、过氧草酸铵、过氧化钡过氧化氢合物、过氧化钡过氧化氢合物、过氧化氢钙、过氧化钙过氧化氢合物、三磷酸二过氧磷酸铵水合物、氟化钾过氧化氢合物、氟化钾三过氧化氢合物、氟化钾二过氧化氢合物、焦磷酸钠二过氧化氢合物、焦磷酸钠二过氧化氢合物八水合物、乙酸钾过氧化氢合物、磷酸钠过氧化氢合物、硅酸钠过氧化氢合物。
优选的催化剂B是过氧化氢、过甲酸、过乙酸、过氧化苯甲酰、二叔丁基过氧化物、过氧化二异丙苯、2,4-二氯过氧化苯甲酰、过氧化癸酰、过氧化月桂酰、氢过氧化枯烯、过氧化蒎烯、萜烷过氧化氢、叔丁基过氧化氢、过氧化乙酰丙酮、过氧化甲乙酮、过氧化丁二酸、过氧化二(十六烷基)二碳酸酯、过氧化乙酸叔丁酯、叔丁基过氧马来酸、过氧化苯甲酸叔丁酯、乙酰环己基磺酰基过氧化物。
优选地,作为用于步骤b)的自由基引发剂使用水溶性偶氮引发剂。优选的是偶氮类引发剂,诸如Dupont-Biesteritz公司的VAZO 522,2′-偶氮双(2,4-二甲基-戊腈)、VAZO 64(偶氮-双-(异丁腈),AIBN)、VAZO 67 2,2′-偶氮双(2-甲基丁腈)、VAZO 88 1,1′-偶氮双(环己烷-1-腈)、VAZO 68,Wako Chemicals的V-70 2,2′-偶氮双(4-甲氧基-2,4-二甲基戊腈)、V-65 2,2′-偶氮双(2,4-二甲基戊腈)、V-601偶氮二异丁酸二甲酯、V-59 2,2′-偶氮双(2-甲基丁腈)、V-40 1,1′-偶氮双(环己烷-1-腈)、VF-096 2,2′-偶氮双[N-(2-丙烯基)-2-甲基丙酰胺]、V-30 1-[(氰基-1-甲基乙基)偶氮]甲酰胺、VAm-110 2,2′-偶氮双(N-丁基-2-甲基-丙酰胺)、VAm-111 2,2′-偶氮双(N-环己基-2-甲基丙酰胺)、VA-046B 2,2′-偶氮双[2-(2-咪唑啉-2-基)丙烷二硫酸酯二水合物、VA-057 2,2′-偶氮双[N-(2-羧乙基)-2-甲基丙脒]四水合物、VA-061 2,2′-偶氮双[2-(2-咪唑啉-2-基)丙烷]、VA-080 2,2′-偶氮双{2-甲基-N-[1,1-双(羟甲基)-2-羟乙基]丙酰胺、VA-085 2,2′-偶氮双{2-甲基-N-[2-(1-羟基-丁基)]丙酰胺}、VA-086 2,2′- 偶氮双[2-甲基-N-(2-羟乙基)-丙酰胺]。
合适的还有偶氮类引发剂,诸如2-叔丁基偶氮-2-氰基丙烷、偶氮二异丁酸二甲酯、偶氮二异丁腈、2-叔丁基偶氮-1-氰基环己烷、1-叔戊基偶氮-1-氰基环己烷。进一步优选的是烷基过缩酮,诸如2,2-双-(叔丁基过氧化)丁烷、3,3-双(叔丁基过氧化)丁酸乙酯、1,1-二-(叔丁基过氧化)环己烷。
优选地,步骤b)中催化剂B比烷基亚膦酸衍生物的比例为1比100至100比1,特别优选1比50至1比1。
优选地,步骤b)中溶剂比烷基亚膦酸衍生物的比例为1比1,000至50比1。
优选地,基于含磷化合物计,引发剂B以每小时0.01至10摩尔%催化剂的速率计量添加。
优选地,步骤b)中的反应在可形成二酯的烯烃(II)和/或溶剂自身的蒸汽压下进行。
合适的溶剂是在步骤a)中提及的溶剂。
优选地,步骤b)中的反应在0.01-100巴的可形成二酯的烯烃的分压下进行。
优选地,步骤b)中的反应在0至250℃的温度,特别优选在20至200℃,且尤其是在50至150℃下进行。
优选地,步骤b)中的反应在1至100巴的总压力下进行。
此外,本发明的主题是一种在金属醇化物(催化剂B)存在下,通过烷基亚膦酸酯(I)与可形成酯的烯烃反应,以连续制备烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物的方法,其特征在于,
a)在设定为用于循环反应混合物、配有冷却设备以及溢流口的独立反应器中预置与反应器体积相应的体积量的制备加合物的烷基亚膦酸衍生物和形成二酯的烯烃,任选以与金属醇化物相应的醇作为溶剂的混合物的方式,并进行循环;
b)在对进行循环的反应器内容物进行冷却的情况下,向反应器中连续导入烷基亚膦酸酯(I)、可形成酯的烯烃(II)以及金属醇化物的醇 溶液,并在约0至80℃的温度在约5-120分钟的时间反应,其中,烷基亚膦酸酯(I)相对可形成酯的烯烃(II)的摩尔比为1比0.9-2,且基于烷基亚膦酸酯(I)计,金属醇化物的量约为0.1至5摩尔%;
和
c)通过反应器的溢流口连续蒸馏出含有本发明方法产物的混合物,并从该混合物中分离出烷基亚膦酸衍生物和可形成二酯的烯烃的加合物。
根据本发明的方法的一种优选实施方式中,反应组分的转化在20至50℃的温度下进行。用反应组分和催化剂溶液给反应器装料例如可以这样进行,
a)将烷基亚膦酸酯(I)、可形成酯的烯烃(II)以及金属醇化物的醇溶液分开而引入反应器中;
b)将烷基亚膦酸酯(I)和可形成酯的烯烃(II)与金属醇化物的醇溶液分开而引入反应器中;或者
c)将烷基亚膦酸酯(I)和金属醇化物的醇溶液与可形成酯的烯烃(II)分开而引入反应器中。
烷基亚膦酸酯(I)的酯基和可形成酯的烯烃(II)的酯基可以相同或不同。此外,当作为溶剂使用的醇和/或金属醇化物的醇组分相应于烷基亚膦酸酯(I)的醇组分和/或可形成酯的烯烃(II)的醇组分时是适宜的。
最后,优选的本发明的特征在于,烷基亚膦酸酯(I)相对于可形成酯的烯烃(II)的摩尔比为1比1-1.3;基于烷基亚膦酸酯(I)计,催化剂B的量为1-5摩尔%;和基于每摩尔烷基亚膦酸酯(I),作为溶剂使用的醇的量为0.1-1,000摩尔。
如果将烷基亚膦酸酯(I)和可形成酯的烯烃(II)与不同的酯基以及这些酯基相应的金属醇化物的醇溶液使用,可获得混合产物。
根据本发明的方法,能够以工业化的规模、以迄今为止未达到过的约95%的产率连续地生产烷基亚膦酸衍生物和可形成二酯的烯烃的加合物。
优选地,在步骤b)中在真空中于0.01至1巴下除去挥发性成分。
优选地,根据本发明的烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物的用途是
-作为粘结剂,例如用于铸造材料和铸造用沙;
-作为在环氧树脂、聚氨酯和不饱和聚酯树脂的固化中的交联剂或促进剂;
-作为聚合物稳定剂,例如作为用于棉织物、聚合物纤维、塑料的光稳定剂和/或热稳定剂;
-作为植物保护剂,例如作为植物生长调节剂,作为除草剂、除草剂、杀虫剂、(土壤)杀菌剂;
-作为用于人和动物的诊断剂、治疗剂或治疗剂中的添加剂,例如作为酶调节剂,用于刺激组织生长;
-作为螯合剂,例如用于在工业供水系统中、在石油生产和在金属处理剂中沉积物的控制;
-作为矿物油添加剂,例如作为抗氧化剂和用于提高辛烷值;
-作为抗蚀剂;
-在洗涤剂和清洁剂应用中,例如作为脱色剂;
-在电子应用中,例如在用于电容器、一次电池和蓄电池的聚合电解质中,以及作为感光层中的自由基捕获剂;
-用于聚酯的聚合催化剂;
-用于聚酯纤维和聚酰胺纤维的可共缩聚阻燃剂;
-聚酯母料;
-用于聚合物的热稳定剂、光稳定剂;
-作为用于血管紧张素转化酶抑制剂的中间产物;
-作为用于细胞功能控制和免疫、炎症、神经和其它疾病治疗的丙氨酰氨肽酶抑制剂或者作为其合成的中间产物;
-作为二肽基肽酶IV抑制剂或作为其合成的中间产物;
-作为用于治疗高血压的环氧化物水解酶抑制剂或者作为其合成的中间产物;
-用于纤维预处理、纤维表面改性。
优选地,根据本发明的烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物的用途是通过方法2的步骤c)中的酯化用于制备酯(和聚酯),条件是或者式(I)中X=H,或者式(II)中R2、R4或R1、R4或R1、R2相同或不同,且至少一个代表选自CO2H、R6-CO2H;或者R2与R4相同,且至少一个代表选自-CO-O-CO-、-CO-S-CO-、-O-NR1-CO-、-CO-PR1-CO-;或者R1、R2相同,且至少一个代表选自-CR2 3-CO-O-CO-、-CR2 3-CO-NR1-CO-、-CR2 3-CO-O-CO-CR2 3、-CR2 3-CO-NR1-CO-CR2 3;
R1、R3或R2、R3或R3、R4相同或不同,且至少一个代表选自H、R5;
R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;
R6表示C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基。
根据本发明优选的是,在方法2的步骤c)中将这样的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃部分形成的加合物通过与成酯剂反应而酯化,所述加合物在烷基亚膦酸部分带有未酯化的次膦酸官能团。
根据本发明优选的是,在方法2的步骤c)中将这样的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃部分形成的加合物通过与成酯剂反应而酯化,所述加合物在可形成二酯的烯烃部分带有未酯化的羧酸官能团。
根据本发明优选的是,在方法2的步骤c)中将这样的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃部分形成的加合物通过与成酯剂反应而进行酯交换,所述加合物在烷基亚膦酸部分带有酯官能团。
根据本发明优选的是,在方法2的步骤c)中将这样的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃部分的加合物通过与成酯剂反应而进行酯交换,所述加合物在羧酸部分带有酯官能团。
根据本发明,合适的成酯剂是C1-C20的,饱和的和不饱和的,一元、二元、三元和四元醇,特别优选C1-C8的,饱和的和不饱和的,一元、二元、三元和四元醇,非常特别优选甲醇、乙醇、丙醇、丁醇、戊醇、辛醇、乙二醇、聚乙二醇、1,2-丙二醇、1,3-丙二醇、丁二醇、 甘油、赤藓糖醇、季戊四醇、烯丙醇、3-丁烯-1-醇、3-羟基-1-丁烯、3-丁烯-2-醇、甲基乙烯基甲醇、2-甲基-2-丙烯-1-醇、甲基烯丙醇、2-丁烯-1-醇、巴豆醇、1-戊烯-3-醇、反-2-戊烯-1-醇、顺-2-戊烯-1-醇、3-戊烯-2-醇、4-戊烯-1-醇、4-戊烯-2-醇、1-己烯-3-醇、顺-2-己烯-1-醇、反-2-己烯-1-醇、顺-3-己烯-1-醇、反-3-己烯-1-醇、4-己烯-1-醇、5-己烯-1-醇、5-己烯-2-醇、1-庚烯-3-醇、1-辛烯-3-醇、反-2-辛烯-1-醇、油醇、萜烯醇、炔丙醇和/或2-丁炔-1,4-二醇。
优选地,根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物的用途是通过在方法3的步骤c)中皂化制备酸,条件是或者式I中X表示H、C1-C18-烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基、C2-C18-烯基;或者式(II)中R2、R4或R1、R4或R1、R2相同或不同,且至少一个代表选自CO2H、R6-CO2H;或者R2与R4相同,且至少一个代表选自-CO-O-CO-、-CO-S-CO-、-O-NR1-CO-、-CO-PR1-CO-;或者R1、R2相同,且至少一个代表选自-CR2 3-CO-O-CO-、-CR2 3-CO-NR1-CO-、-CR2 3-CO-O-CO-CR2 3、-CR2 3-CO-NR1-CO-CR2 3;R1、R3或R2、R3或R3、R4相同或不同,且至少一个代表选自H、R5;R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;R6表示C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基。
根据本发明优选的是,在方法3的步骤c)中将这样的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃部分形成的加合物通过与催化剂C反应而皂化生成次膦酸官能团,所述加合物在烷基亚膦酸部分带有酯官能团。
根据本发明优选的是,在方法3的步骤c)中将这样的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃部分形成的加合物通过与催化剂C反应而皂化生成羧酸官能团,所述加合物在羧酸部分带有酯官能团。
根据本发明优选的是,在方法3的步骤c)中将这样的由烷基亚膦酸衍生物(I)和可形成二酯的烯烃部分形成的加合物通过与催化剂C反应而皂化生成羧酸官能团,所述加合物在羧酸部分带有至少一个腈官能团。
根据本发明优选的催化剂C是 酸、 碱、水;优选是无机酸,如盐酸、硫酸、硝酸、磷酸、磺酸、碱金属氢氧化物或碱土金属氢氧化物。
合适的碱是金属、金属氢化物和金属醇化物,例如锂、氢化锂、氢化铝锂、甲基锂、丁基锂、叔丁基锂、二异丙基氨基锂、钠、氢化钠、硼氢化钠、甲醇钠、乙醇钠或丁醇钠、甲醇钾、乙醇钾或丁醇钾,此外还有氢氧化钠、氢氧化钾、氢氧化锂和氢氧化钡。
非常特别优选是硫酸、盐酸、磷酸、甲基苯磺酸;氢氧化钠溶液、氢氧化钾溶液、氢氧化钙溶液。
如果获得了烷基亚膦酸(I)和可形成二酯的烯烃(II)的加合物的盐,可以将它们与无机酸反应成相应的酸,并与步骤b)类似地进行酯化。
如果获得了烷基亚膦酸和可形成二酯的烯烃的加合物的铵盐,可以首先将其与碱反应生成烷基亚膦酸和可形成二酯的烯烃的加合物的盐,然后与无机酸反应生成相应的酸,并与步骤b)类似地进行酯化。
优选地,酸或碱水解可以在水和惰性溶剂的存在下进行。合适的惰性溶剂是在方法步骤a)中提及的溶剂,优选是具有1至6个碳原子的低分子量的醇。
在进行水解时,水的存在是重要的。水量可以从作为最小量的化学计量的所需量延伸到过量。
水解优选以1∶1至1∶1,000,特别优选1∶1至1∶10的磷/水摩尔比进行。
水解优选以1∶1至1∶300,特别优选1∶1至1∶20的磷/碱或磷/酸摩尔比进行。
所使用的溶剂的量一般为0.5kg至1.5kg每kg烷基亚膦酸(I)和可形成二酯的烯烃(II)的加合物,优选为0.6kg至1.0kg。
反应温度优选为50至140℃,优选为80至130℃。
优选地,反应在1至100巴的总压力下进行,特别优选在1至10巴的总压力下进行。
反应时间为0.2至20小时,特别优选1至12小时。
烷基亚膦酸(I)和可形成二酯的烯烃(II)的加合物可以随后反应生成另外的金属盐。
优选地,所使用的金属化合物是金属Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、K的化合物,特别优选Mg、Ca、Al、Ti、Zn、Sn、Ce、Fe的化合物。
作为溶剂,合适的是方法步骤a)中使用的溶剂。
优选地,反应在水性介质中进行。
优选地,反应在改进的溶剂体系中进行。为此添加酸性成分、增溶剂、抑泡剂等。
优选地,将烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物、其酸、酯和/或碱金属盐与Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的金属化合物反应生成这些金属的烷基亚膦酸衍生物和可形成二酯的烯烃(II)的加合物。
在此,反应以如下烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物与金属的摩尔比进行:8比1至1比3(对于四价金属离子或者具有稳定的四价氧化态的金属),6比1至1比3(对于三价金属离子或者具有稳定的三价氧化态的金属),4比1至1比3(对于二价金属离子或者具有稳定的二价氧化态的金属),以及3比1至1比4(对于一价金属离子或者具有稳定的一价氧化态的金属)。
优选地,将烷基亚膦酸和可形成二酯的烯烃(II)的加合物的酯和/或碱金属盐转化成相应的酸,并将其与Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的金属化合物反应生成这些金属的烷基亚膦酸和可形成二酯的烯烃的加合物。
优选地,将烷基亚膦酸和可形成二酯的烯烃(II)的加合物的酸和酯转化成碱金属盐,并将其与Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的金属化合物反应生成这些金属的烷基亚膦酸和可形成二酯的烯烃(II)的加合物。
优选地,用于方法步骤c)的Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce 或Fe的金属化合物是金属、金属氧化物、金属氢氧化物、氢氧化金属氧化物、金属硼酸盐、金属碳酸盐、金属碱式碳酸盐、金属碱式碳酸盐水合物、金属碱式碳酸混盐、金属碱式碳酸混盐水合物、金属磷酸盐、金属硫酸盐、金属硫酸盐水合物、金属碱式硫酸盐水合物、金属碱式硫酸混盐水合物、金属硫酸氧盐、金属乙酸盐、硝酸金属盐、金属氟化物、金属氟化物水合物、金属氯化物、金属氯化物水合物、金属氯氧化物、金属溴化物、金属碘化物、金属碘化物水合物、金属羧酸衍生物和/或金属烷氧化物。
优选地,金属化合物是氯化铝、氢氧化铝、硝酸铝、硫酸铝、硫酸氧钛、硝酸锌、氧化锌、氢氧化锌和/或硫酸锌。
合适的还有金属铝、氟化铝、羟铝基氯化物、溴化铝、碘化铝、硫化铝、硒化铝;磷化铝、次磷酸铝、锑化铝、氮化铝;碳化铝、六氟硅酸铝;氢化铝、氢化铝钙、硼氢化铝;氯酸铝;硫酸铝钠、硫酸铝钾、硫酸铝铵、硝酸铝、偏磷酸铝、磷酸铝、硅酸铝、硅酸镁铝、碳酸铝、铝水滑石、碳酸铝钠、硼酸铝;硫氰酸铝;氧化铝、铝酸,它们的相应的水合物和/或聚氢氧化铝化合物,其优选具有9至40重量%的铝含量。
合适的还有单、二、寡聚、多聚羧酸的铝盐,例如二乙酸铝、乙酰酒石酸铝、甲酸铝、乳酸铝、草酸铝、酒石酸铝、油酸铝、棕榈酸铝、硬脂酸铝、三氟甲磺酸铝、苯甲酸铝、水杨酸铝、8-氧代喹啉铝。
同样合适的是元素、金属锌以及锌盐,例如卤化锌(氟化锌、氯化锌、溴化锌、碘化锌)。
合适的还有硼酸锌、碳酸锌、碱式碳酸锌、硅酸锌、六氟硅酸锌、锡酸锌、碱式锡酸锌、碱式碳酸铝镁锌;硝酸锌、亚硝酸锌、磷酸锌、焦磷酸锌;硫酸锌、磷化锌、硒化锌、碲化锌和第七主族的含氧酸的锌盐(次卤酸盐;亚卤酸盐;卤酸盐,例如碘酸锌;高卤酸盐,例如高氯酸锌);拟卤化物的锌盐(硫氰酸锌,氰酸锌,氰化锌);氧化锌、过氧化锌、氢氧化锌或混合的氢氧化锌氧化物。
优选的是过渡金属含氧酸的锌盐(例如氢氧化铬酸(VI)锌,亚铬 酸锌,钼酸锌,高锰酸锌,钼酸锌)。
合适的还有单、二、寡聚、多聚羧酸的锌盐,例如甲酸锌、乙酸锌、三氟乙酸锌、丙酸锌、丁酸锌、戊酸锌、辛酸锌、油酸锌、硬脂酸锌、草酸锌、酒石酸锌、柠檬酸锌、苯甲酸锌、水杨酸锌、乳酸锌、丙烯酸锌、马来酸锌、丁二酸锌,氨基酸(甘氨酸)的盐、酸性的羟基官能化盐(苯酚锌等),对苯酚磺酸锌、乙酰丙酮酸锌、锡酸锌、二甲基二硫代氨基甲酸锌、三氟甲磺酸锌。
在钛化合物方面合适的是金属钛以及钛(III)和/或(IV)的氯化物、硝酸盐、硫酸盐、甲酸盐、乙酸盐、溴化物、氟化物、氯氧化物、硫酸氧化物、氧化物、正丙氧化物、正丁氧化物、异丙氧化物、乙氧化物、2-乙基己氧化物。
合适的还有金属锡以及锡盐(氯化亚锡(II)和/或氯化锡(IV));氧化锡和烷氧化锡,例如叔丁氧锡(IV)。
合适的还有氟化铈(III)、氯化铈(III)、硝酸铈(III)。
对于锆化合物,优选是金属锆以及锆盐(诸如氯化锆、硫酸锆、乙酸氧锆、氯化氧锆)。进一步优选是氧化锆以及叔丁氧锆(IV)。
优选地,反应优选在0.1至70重量%,更优选5至40重量%的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物的盐的固含量下进行。
优选地,反应在20至250℃的温度下,优选在80至120℃的温度下进行。
反应在0.01至1,000巴之间,优选0.1至100巴的压力下进行。
优选地,反应在1×10-7至1×102h的反应时间内进行。
优选地,金属Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物可选地具有0.01至10重量%,优选0.1至1重量%的残余水分;0.1至2,000μm,优选10至500μm的平均粒度;80至800g/l,优选200至700g/l的容积密度;根据Pfrengle的流动性在0.5至10,优选1至5。
优选地,根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的 加合物的用途是作为阻燃剂。
根据本发明的由烷基亚膦酸衍生物和可形成二酯的烯烃形成的加合物可以通过它们的官能团作为共聚物组分嵌入热塑性聚合物(例如聚酯)中。在共聚过程中,调整加合物的含量以便在阻燃性整理过的聚合物中产生所期望的阻燃性。与常规的具有填料特征或添加特征的阻燃剂相比,优点在于:均匀的分散、在聚合物中持久地固定(没有流出或蒸出)和改善的机械韧性和强度性能。这类阻燃性共聚物也可以复合到聚合物中。产生这样的共混物,其与常规的具有填料特征或添加剂特征的阻燃剂相比同样具有更有利的性质。
根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物也可以任选地并入,如在EP-A-1693403中所描述的那样:该文献中的阻燃热塑性模塑材料包含烷基亚膦酸衍生物和可形成二酯的烯烃的加合物作为聚合物主链中的结构单元。根据本发明的加合物之后通过形成化学键反应进入到聚合物大分子中。这可以通过在单体聚合时嵌入而发生,或通过经打断大分子链并嵌入根据本发明的加合物的事后嵌入而发生。
根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物作为结构单元在聚合物主链中可以随机地分布在大分子上。相应地,它们也可以偶尔作为端基出现(例如US-A-3941752中所描述)。
原则上,可以采用每种可能的将根据本发明的加合物反应到聚合物中的方法。例如可以将热塑性聚合物与根据本发明的加合物混合。
根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物也可以作为结构单元在聚酰胺的聚合物主链中使用。典型地,这样的阻燃性聚酰胺含有介于0.05和5.0重量%之间的磷,优选介于0.4和2.0重量%之间。
优选地,根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物的用途是用于制备阻燃热塑性聚合物模塑材料。
优选地,所述阻燃热塑性模塑材料含有0.5至45重量%的根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物,0.5至95重 量%的热塑性聚合物或它们的混合物,其中各组分之和为100重量%。
优选地,所述阻燃热塑性模塑材料含有0.5至40重量%的根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物,10至85.5重量%的热塑性聚合物或它们的混合物,2至40重量%的添加剂,2至40重量%的填料或增强材料,其中各组分之和为100重量%。
优选地,添加剂是抗氧化剂、抗静电剂、发泡剂、另外的阻燃剂、热稳定剂、抗冲击改性剂、加工助剂、润滑剂、光稳定剂、抗滴落剂、增容剂、补强剂、填料、晶核形成剂、成核剂、用于激光标记的添加剂、水解稳定剂、链增长剂、涂料颜料、增塑剂和/或塑化剂。
优选的添加剂还有三水合铝,氧化锑,溴代芳香烃或溴代脂环烃,酚,醚,氯化石蜡,六氯环戊二烯加合物,红磷,三聚氰胺衍生物,氰尿酸三聚氰胺,多聚磷酸铵和氢氧化镁;此外还有另外的阻燃剂,尤其是二烃基次膦酸的盐。
优选地,聚合物是热塑性或热固性聚合物。
优选地,热塑性聚合物是单烯烃和二烯烃的聚合物,例如聚丙烯、聚异丁烯、聚1-丁烯、聚4-甲基-1-戊烯、聚异戊二烯或聚丁二烯,以及环烯烃的聚合物,例如环戊烯的聚合物或降冰片烯的聚合物;还有聚乙烯(任选可以交联),例如高密度聚乙烯(HDPE)、高分子量高密度聚乙烯(HDPE-HMW)、超高分子量高密度聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、线性低密度聚乙烯(LLDPE)、极低密度聚乙烯(VLDPE),及它们的混合物。
优选地,热塑性聚合物是单烯烃和二烯烃彼此之间的共聚物或与另外的乙烯基单体的共聚物,例如乙烯-丙烯共聚物、线性低密度聚乙烯(LLDPE)和它们与低密度聚乙烯(LDPE)的混合物、丙烯-1-丁烯共聚物、丙烯-异丁烯共聚物、乙烯-1-丁烯共聚物、乙烯-己烯共聚物、乙烯-甲基戊烯共聚物、乙烯-庚烯共聚物、乙烯-辛烯共聚物、丙烯-丁二烯共聚物、异丁烯-异戊二烯共聚物、乙烯-丙烯酸烷基酯共聚物、乙烯-甲基丙烯酸烷基酯共聚物、乙烯-乙酸乙烯酯共聚物和它们与一氧化碳的共聚物,或乙烯-丙烯酸共聚物和它们的盐(离聚物),以及 乙烯与丙烯和一种二烯(例如己二烯、二环戊二烯、亚乙基降冰片烯)的三元共聚物;还有这样的共聚物彼此之间的混合物,例如聚丙烯/乙烯-丙烯共聚物,LDPE/乙烯-乙酸乙烯酯共聚物、LDPE-乙烯-丙烯酸共聚物、LLDPE/乙烯-乙酸乙烯酯共聚物、LLDPE/乙烯-丙烯酸共聚物,和交替的或无规的聚烯烃/一氧化碳共聚物及它们与其他聚合物(如聚酰胺)的混合物。
优选地,聚合物是含烃类树脂(例如C5-C9),包括其氢化改性物(例如增粘树脂)和聚烯烃与淀粉的混合物。
优选地,热塑性聚合物是聚苯乙烯、聚对甲基苯乙烯和/或聚-α-甲基苯乙烯。
优选地,热塑性聚合物是苯乙烯或α-苯乙烯与二烯或丙烯酸衍生物的共聚物,例如苯乙烯-丁二烯、苯乙烯-丙烯腈、苯乙烯-甲基丙烯酸烷基酯、苯乙烯-丁二烯-丙烯酸烷基酯和苯乙烯-丁二烯-甲基丙烯酸烷基酯、苯乙烯-马来酸酐、苯乙烯-丙烯腈-丙烯酸甲酯;由苯乙烯共聚物和另一种聚合物(例如聚丙烯酸酯、二烯聚合物或乙烯-丙烯-二烯三元共聚物)构成的高冲击韧性的混合物;以及苯乙烯类的嵌段共聚物,例如苯乙烯-丁二烯-苯乙烯、苯乙烯-异戊二烯-苯乙烯、苯乙烯-乙烯/丁烯-苯乙烯或苯乙烯-乙烯/丙烯-苯乙烯。
优选地,热塑性聚合物还有苯乙烯或α-甲基苯乙烯的接枝共聚物,例如苯乙烯接枝到聚丁二烯上,苯乙烯接枝到聚丁二烯-苯乙烯共聚物或接枝到聚丁二烯-丙烯腈共聚物上,苯乙烯和丙烯腈(或甲基丙烯腈)接枝到聚丁二烯上;苯乙烯、丙烯腈和甲基丙烯酸甲酯接枝到聚丁二烯上;苯乙烯和马来酸酐接枝到聚丁二烯上;苯乙烯、丙烯腈和马来酸酐或马来酰亚胺接枝到聚丁二烯上;苯乙烯和马来酰亚胺接枝到聚丁二烯上、苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯接枝到聚丁二烯上;苯乙烯和丙烯腈接枝到乙烯-丙烯-二烯烃三元共聚物上,苯乙烯和丙烯腈接枝到聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上,苯乙烯和丙烯腈接枝到丙烯酸酯-丁二烯共聚物上,以及它们的混合物,例如作为所谓的ABS(丙烯腈-丁二烯-苯乙烯)-、MBS(甲基丙烯酸 甲酯-丁二烯-苯乙烯)-、ASA(丙烯腈-苯乙烯-丙烯酸酯)-或AES(丙烯腈-乙烯-苯乙烯)-聚合物已知的那些。
优选地,热塑性聚合物是含卤聚合物,例如聚氯异戊二烯;氯化橡胶;氯化和溴化的由异丁烯-异戊二烯构成的共聚物(卤代丁基橡胶);氯化或氯磺酰化的聚乙烯;乙烯和氯化乙烯的共聚物;表氯醇均聚物和表氯醇共聚物,尤其是由含卤素的乙烯基化合物构成的聚合物,例如聚氯乙烯、聚偏氯乙烯、聚氟乙烯、聚偏氟乙烯;以及它们的共聚物,诸如氯乙烯-偏氯乙烯、氯乙烯-乙酸乙烯酯或偏氯乙烯-乙酸乙烯酯。
优选地,热塑性聚合物是衍生自α,β-不饱和酸和它们的衍生物的聚合物,诸如聚丙烯酸酯和聚甲基丙烯酸酯、用丙烯酸丁酯抗冲改性的聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈和所提及的单体彼此之间或与另外的不饱和单体的共聚物,例如丙烯腈-丁二烯共聚物、丙烯腈-丙烯酸烷基酯共聚物、丙烯腈-丙烯酸烷氧基烷基酯共聚物、丙烯腈-卤代乙烯共聚物或丙烯腈-甲基丙烯酸烷基酯-丁二烯三元共聚物。
优选地,热塑性聚合物是衍生自不饱和醇和胺或者其缩醛或丙烯酸衍生物的那些,诸如聚乙烯醇、聚乙酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸二烯丙酯、聚烯丙基三聚氰胺;以及它们与烯烃的共聚物。
优选地,热塑性聚合物是环醚的均聚物和共聚物,诸如聚亚烷基二醇、聚氧化乙烯、聚氧化丙烯或它们与双缩水甘油醚的共聚物。
优选地,聚合物是热塑性聚缩醛,诸如聚甲醛,以及这样的聚甲醛,其含有例如氧化乙烯的共聚单体;用热塑性聚氨酯、丙烯酸酯或MBS改性的聚缩醛。
优选地,热塑性聚合物是聚苯醚和聚苯硫醚和它们与苯乙烯聚合物或聚酰胺的混合物。
优选地,热塑性聚合物是聚氨酯,其衍生自聚醚、聚酯和聚丁二烯(一方面具有端羟基,且另一方面具有脂族或芳族多异氰酸酯), 以及它们的前体。
优选地,热塑性聚合物是聚酰胺和共聚酰胺,其衍生自二胺和二羧酸和/或衍生自氨基羧酸或相应的内酰胺,诸如尼龙4、尼龙6(Akulon K122,DSM;Zytel 7301,DuPont公司;Durethan B 29,Bayer公司)、尼龙6/6(Zytel 101,DuPont公司;Durethan A30,Durethan AKV,Durethan AM,Bayer公司;Ultramid A3,BASF公司)、尼龙6/10、尼龙6/9、尼龙6/12、尼龙4/6、尼龙12/12、尼龙11、尼龙12(GrillamidL20,Ems Chemie公司);来自间二甲苯、二胺和己二酸的芳族聚酰胺;由六亚甲基二胺和间苯二甲酸和/或对苯二甲酸和任选的作为改性剂的一种弹性体制备的聚酰胺,例如聚-2,4,4-三甲基六亚甲基-对苯二甲酰胺或聚-间亚苯基间苯二甲酰胺;上文提到的聚酰胺与聚烯烃、烯烃共聚物、离子聚合物或化学键合或接枝的弹性体,或者与聚醚(例如与聚乙二醇、聚丙二醇或聚丁二醇)形成的嵌段共聚物。还有经EPDM或ABS改性的聚酰胺或共聚酰胺;以及在处理过程中缩合的聚酰胺(“RIM聚酰胺体系”)。
优选地,热塑性聚合物是聚脲、聚酰亚胺、聚酰胺酰亚胺、聚醚酰亚胺、聚酯酰亚胺、聚乙内酰脲和聚苯并咪唑。
优选地,热塑性聚合物是衍生自二羧酸和二醇和/或羟基羧酸或相应的内酯的聚酯,诸如聚对苯二甲酸乙二酯;聚对苯二甲酸丁二酯(Celanese公司的Celanex 2500、Celanex 2002;BASF公司的Ultradur);聚-1,4-二羟甲基环己烷-对苯二甲酸酯;聚羟基苯甲酸酯;以及嵌段聚醚酯,其衍生自具有羟基端基的聚醚;还有用聚碳酸酯或MBS改性的聚酯。
优选地,热塑性聚合物是聚碳酸酯、聚酯碳酸酯,还有聚砜、聚醚砜和聚醚酮。
优选地,聚合物是上述聚合物的混合物(共混物)例如PP/EPDM(聚丙烯/乙烯-丙烯-二烯橡胶)、聚酰胺/EPDM或ABS、PVC/EVA、PVC/ABS、PVC/MBS、PC/ABS、PBTP/ABS、PC/ASA、PC/PBT、PVC/CPE、PVC/丙烯酸酯、POM/热塑性PUR、PC/热塑性PUR、POM/丙烯酸酯、 POM/MBS、PPO/HIPS、PPO/PA 6.6和共聚物、PA/HDPE、PA/PP、PA/PPO、PBT/PC/ABS或PBT/PET/PC,其中PP表示聚丙烯、EPDM表示(乙烯-丙烯-二烯橡胶)、ABS表示丙烯腈-丁二烯-苯乙烯、PVC表示聚氯乙烯、EVA表示乙烯-乙酸乙烯酯、MBS表示甲基丙烯酸甲酯-丁二烯-苯乙烯、PC表示聚碳酸酯、PBTP表示聚对苯二甲酸丁二酯、CPE表示氯化聚乙烯、POM表示聚甲醛、PPO表示聚苯醚、PUR表示聚氨酯、PC表示聚碳酸酯、HIPS表示高抗冲聚苯乙烯、PA表示聚酰胺、HDPE表示高密度聚乙烯、PBT表示聚对苯二甲酸丁二酯、PET表示聚对苯二甲酸乙二酯。
优选地,根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物的用途是用于制备阻燃性聚合物成型体、聚合物膜、聚合物丝和聚合物纤维。
优选地,阻燃性聚合物成型体、聚合物膜、聚合物丝和聚合物纤维含有0.5至45重量%的根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物,0.5至98重量%的热塑性聚合物或它们的混合物,0.5至55重量%的添加剂和0.5至55重量%的填料或增强材料。
最后,本发明还涉及一种用于制备阻燃性聚合物成型体的方法,其特征在于,将根据本发明的阻燃性聚合物模塑材料通过注塑(例如注塑机(型号Aarburg Allrounder))和挤压、发泡注塑成型、气辅注塑成型、吹塑成型、铸塑成型、压延成型、层压法或在升高的温度涂覆加工成阻燃性聚合物成型体。
根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物可以通过官能团作为共聚组分插入热固性聚合物(例如不饱和聚酯或环氧化物)中。
优选地,热固性聚合物是不饱和聚酯树脂(UP树脂),其衍生自饱和的和不饱和的二羧酸或其酸酐与多元醇的共聚酯,以及作为交联剂的乙烯基化合物。UP树脂通过采用引发剂(例如过氧化物)和促进剂的自由基聚合反应而固化。
优选的用于制备聚酯树脂的不饱和二羧酸和二羧酸衍生物是马来 酸酐和富马酸酐。
优选的饱和二羧酸是邻苯二甲酸、间苯二甲酸、对苯二甲酸、四氢邻苯二甲酸、己二酸。
优选的二醇是1,2-丙二醇、乙二醇、二乙二醇和新戊二醇、新戊二醇、乙氧基化或丙氧基化的双酚A。
优选的用于交联的乙烯基化合物是苯乙烯。
优选的固化体系是过氧化物和金属共引发剂,例如氢过氧化物和辛酸钴和/或过氧化苯甲酰和芳族胺和/或紫外光和光敏剂,例如安息香醚。
优选的氢过氧化物是二叔丁基过氧化物、过氧化辛酸叔丁酯、过氧化新戊酸叔丁酯、过氧化(2-乙基己酸)叔丁酯、过氧化马来酸叔丁酯、过氧化异丁酸叔丁酯、过氧化苯甲酰、二乙酰过氧化物、过氧化丁二酰、过氧化对氯苯甲酰、过氧化二碳酸二环己酯。
优选地,基于所有共聚单体的质量计算,以0.1至20重量%,优选0.2至15重量%的量使用引发剂。
优选的金属共引发剂是钴化合物、锰化合物、铁化合物、钒化合物、镍化合物或铅化合物。优选地,基于所有共聚单体的质量计算,以0.05至1重量%的量使用金属共引发剂。
优选的芳族胺是二甲基苯胺、二甲基对甲苯、二乙基苯胺和苯基二乙醇胺。
一种用于制备阻燃性共聚物的方法的特征在于,将至少一种乙烯型不饱和二羧酸酐(衍生自至少一种C4-C8二羧酸),至少一种乙烯基芳族化合物和多元醇共聚,并与根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物反应。
一种用于制备阻燃热固性材料的方法的特征在于,将热固性树脂与由根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物构成的阻燃组分混合,并将产生的混合物在3至10巴的压力和20至60℃的温度下湿压(冷压)。
另一种用于制备阻燃热固性材料的方法的特征在于,将热固性树 脂与由根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物构成的阻燃组分混合,并将产生的混合物在3至10巴的压力和80至150℃的温度下湿压(温压或热压)。
优选地,聚合物是交联的环氧树脂,其衍生自脂族、脂环族、杂环或芳族缩水甘油基化合物,例如双酚A二缩水甘油醚、双酚F二缩水甘油醚,其借助于常规固化剂和/或促进剂交联。
合适的缩水甘油基化合物是双酚A二缩水甘油醚;双酚F二缩水甘油醚;苯酚-甲醛树脂和甲酚-甲醛树脂的多缩水甘油醚;邻苯二甲酸、间苯二甲酸和对苯二甲酸,以及偏苯三酸的多缩水甘油醚;芳族胺和杂环氮碱的N-缩水甘油基化合物;以及多元脂族醇的二缩水甘油基化合物和多缩水甘油基化合物。
合适的固化剂是多胺,诸如二乙三胺、三乙四胺、氨基乙基哌嗪、异佛尔酮二胺、多氨基胺、二氨基二苯甲烷、二氨基二苯酚砜和双氰胺;同样还有多元酸或它们的酸酐,例如邻苯二甲酸酐、马来酸酐、四氢邻苯二甲酸酐、甲基四氢邻苯二甲酸酐、六氢邻苯二甲酸酐和甲基六氢邻苯二甲酸酐;以及酚,例如苯酚-酚醛清漆-树脂、甲酚-酚醛清漆-树脂、二环戊二烯-苯酚加合物树脂、苯酚芳烷基树脂、甲酚芳烷基树脂、萘酚芳烷基树脂、双酚-改性苯酚芳烷基树脂、苯酚三羟甲基甲烷树脂、四苯酚基乙烷树脂、萘酚-酚醛清漆-树脂、萘酚-苯酚共缩聚物树脂、萘酚-甲酚共缩聚物树脂、双酚-改性苯酚树脂和氨基三嗪-改性苯酚树脂。所有的固化剂可以单独或彼此组合使用。
在聚合时用于交联的合适的催化剂或者促进剂是季胺、苄基二甲基胺、N-烷基吡啶、咪唑、1-甲基咪唑、2-甲基咪唑、2-乙基-4-甲基咪唑、2-乙基-4-甲基咪唑、2-苯基咪唑、2-十七烷基咪唑、有机酸的金属盐、路易斯酸和胺络合物盐。
环氧树脂适合于包装带电的或者电学的组件并用于饱和操作和浸渍操作。在电工学中,环氧树脂压倒性地用于阻燃性整理并用于电路板和绝缘子。
优选地,聚合物是交联的聚合物,其一方面衍生自醛,另一方面 衍生自酚、脲或三聚氰胺,诸如酚醛树脂、脲醛树脂和三聚氰胺甲醛树脂。优选地,聚合物是可交联的丙烯酸树脂,其衍生自取代的丙烯酸酯,例如衍生自环氧丙烯酸酯、氨基甲酸酯丙烯酸酯或聚酯丙烯酸酯。
优选地,聚合物是醇酸树脂、聚酯树脂和丙烯酸树脂,其与三聚氰胺树脂、脲醛树脂、异氰酸酯、异氰脲酸酯、多异氰酸酯或环氧树脂交联。
本发明还涉及阻燃性聚氨酯模塑材料,其通过0.1至50重量份的根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物与30至65重量份的多异氰酸酯和30至65重量份的多元醇反应而制备。
用于制备阻燃性聚氨酯模塑材料的方法的特征在于,将170至70重量份、优选130至80重量份的多异氰酸酯与100重量份的多元醇,0.1至50重量份的根据本发明的烷基亚膦酸衍生物和可形成二酯的烯烃的加合物和0.1至4重量份、特别优选1至2重量份的催化剂进行反应,并可选地用0.1至1.8重量份、优选0.3至1.6重量份的发泡剂发泡。
优选的多元醇是乙二醇、1,2-丙二醇、双酚A、三羟甲基丙烷、甘油、季戊四醇、山梨醇、糖、降解淀粉、乙二胺、二氨基甲苯和/或苯胺的氧化烯烃加合物,其用作引发剂。优选的氧烷基化试剂优选含有2至4个碳原子,特别优选是氧化乙烯和氧化丙烯。
优选的聚酯多元醇通过多元醇(诸如乙二醇、二乙二醇、丙二醇、1,4-丁二醇、1,5-戊二醇、甲基戊二醇、1,6-己二醇、三羟甲基丙烷、甘油、季戊四醇、二甘油、葡萄糖和/或山梨醇)与二元酸(草酸、丙二酸、丁二酸、酒石酸、己二酸、癸二酸、马来酸、富马酸、邻苯二甲酸和/或对苯二甲酸)缩聚而获得。这些聚酯多元醇可以单独或彼此组合使用。
合适的多异氰酸酯是芳族、脂环族或脂族的具有不少于两个异氰酸酯基团的多异氰酸酯,及其混合物。优选是芳族多异氰酸酯,诸如甲苯二异氰酸酯、亚甲基二苯基二异氰酸酯、萘二异氰酸酯、苯二甲 基二异氰酸酯、三-(4-异氰酸基苯基)甲烷和多亚甲基多苯基二异氰酸酯;脂环族多异氰酸酯,诸如亚甲基二苯基二异氰酸酯、甲苯二异氰酸酯;脂族多异氰酸酯和六亚甲基二异氰酸酯、异佛尔酮二异氰酸酯、Demeryl二异氰酸酯、1,1-亚甲基双(4-异氰酸环己烷-4,4′-异氰酸基二环己基甲烷异构体混合物、1,4-环己基二异氰酸酯、Desmodur-型号(Bayer)和赖氨酸二异氰酸酯及其混合物。
合适的多异氰酸酯是改性的产物,其通过将多异氰酸酯与多元醇、脲、碳二亚胺和/或缩二脲反应而获得。
用于制备聚氨酯的合适的催化剂是强碱,羧酸的碱金属盐或脂族季胺。优选是四级的氢氧化铵,碱金属氢氧化物或醇化物,乙酸钠或乙酸钾,辛酸钾,苯甲酸钠,1,4-二氮杂双环[2.2.2]辛烷,N,N,N′,N′-四甲基六亚甲基二胺,N,N,N′,N′-四甲基丙二胺,N,N,N′,N′,N″-五甲基二乙三胺,N,N′-二-(C1-C2)-烷基哌嗪,三甲基氨基乙基哌嗪,N,N-二甲基环己基胺,N,N-二甲基苄胺,N-甲基吗啉,N-乙基吗啉,三甲胺、三乙胺、三丁胺、三乙二胺、双(二甲基氨基烷基)哌嗪,N,N,N′,N′-四甲基乙二胺,N,N-二乙基苄胺,双(N,N-二乙基氨基乙基)己二酸酯,N,N,N′,N′-四甲基-1,3-丁二胺,N,N-二乙基-β-苯基乙基胺,1,2-二甲基咪唑,2-甲基咪唑等。
优选地,多异氰酸酯相对于多元醇的重量比例为170比70,优选130比80,基于多元醇的100重量份计。
优选地,催化剂的重量比例为0.1至4重量份,特别优选1至2重量份,基于多元醇的100重量份计。
用于聚氨酯的优选的发泡剂是水、烃、氯氟烃、氟代烃等。用于聚氨酯的发泡剂的量是0.1至1.8重量份,优选0.3至1.6重量份,且尤其是0.8至1.6重量份,基于多元醇的100重量份计。
通过以下实施例阐释本发明。
阻燃性聚合物模塑材料和阻燃性聚合物成型体的制备、加工和测 试
将阻燃成分与聚合物粒料及任选的添加剂混合,并在双螺杆挤出机上(型号Leistritz LSM 30/34)于230至260℃(PBT-GV)或260至280℃(PA 66-GV)的温度加工。将均质化的聚合物束拔出,在水浴中冷却并随后造粒。
充分干燥后,将模塑材料在注塑机(型号Aarburg Allrounder)上于240至270℃(PBT-GV)或260至290℃(PA66-GV)的物料温度加工成试验样品。该试验样品根据UL 94-测试法(Underwriter Laboratories)针对抗火性(阻燃)进行测试并分级。
对由每一种混合物构成的测试样品测定消防等级UL 94(Underwriter Laboratories),在厚度1.5mm的测试样品上。
根据UL94得到以下消防等级:
V-0:续燃时间不超过10秒,10次点火的总续燃时间不多于50秒,没有燃烧滴落,试样没有完全燃尽,点火结束后大于30秒无试样残炽;
V-1:点火结束后续燃时间不超过30秒,10次点火的总续燃时间不超过250秒,点火结束后大于60秒无试样残炽,其余标准同V-0的情况;
V-2:通过燃烧滴落引燃棉絮,其余标准同V-1的情况;
不可分级的(nkl):不满足消防等级V-2。
此外,对一些所研究的试样测量LOI值。LOI值(极限氧指数)依照ISO4589确定。依照ISO4589,LOI对应于在氧气和氮气的混合物中刚好仍能维持塑料燃烧的最低氧浓度的体积百分数。LOI值越高,所测试的材料的越难燃。
LOI 23 可燃
LOI 24-28 有条件的可燃
LOI 29-35 阻燃
LOI>36 特别阻燃
实施例1
在室温下于配有搅拌器和强效冷凝器的三颈烧瓶中预置188g水,并在搅拌下通入氮气脱气。然后在氮气下加入0.2mg硫酸钯(II)和2.3mg三(3-磺酸基苯基)-膦三钠盐并搅拌,然后加入溶于66g水中的66g次膦酸。将反应溶液转移至21-B ü chi反应器中并在搅拌下加压充入乙烯,并将反应混合物加热至80℃。吸收28g乙烯之后冷却至室温并排除游离的乙烯。将反应混合物在旋转蒸发仪上除去溶剂。向残余物中混入100g去离子水并在室温下搅拌。过滤获得的残余物并用甲苯萃取滤液,之后在旋转蒸发仪上脱除溶剂,收集获得的乙基亚膦酸。
实施例2
如实施例1中,将66g次膦酸,188g丁醇,28g乙烯,0.47mg三(二亚苄基丙酮)二钯和0.63mg4,5-双(二苯基膦基)-9,9-二甲基咕吨进行反应,然后除去后面的二者并随后再次加入124g正丁醇。在80-110℃的反应温度下通过共沸蒸馏除去形成的水。通过在1毫巴下蒸馏纯化产物(乙基亚膦酸正丁酯)。
实施例3
将94.1g乙基亚膦酸(如实施例1中制备)和52.0g衣康酸在配有搅拌器、回流冷凝管、温度计和氮气导入管的四颈烧瓶中加热至160℃。反应开始后,继续搅拌15min,再次加入36.4g衣康酸,并在另外的30min后加入41.6g衣康酸。在减压下蒸馏出挥发性成分。获得220g由乙基亚膦酸和衣康酸形成的加合物,其含有13.4%的磷。氧杂-10-磷杂菲与衣康酸的加合物仅含有9%的磷。
实施例4
将94.1g乙基亚膦酸(如实施例1中制备)和116g马来酸装入配有搅拌器、回流冷凝管、温度计和氮气导入管的四颈圆底烧瓶中。 于1h内在约10℃滴加16.4g 5%浓度的AIBN在冰醋酸中的溶液。之后在真空中蒸馏出溶剂。获得191g由乙基亚膦酸和马来酸形成的加合物,其含有14.5%的磷。氧杂-10-磷杂菲与马来酸的加合物仅含有9.3%的磷。
实施例5
将94.1g乙基亚膦酸(如实施例1中制备)和144g富马酸二甲酯装入配有搅拌器、回流冷凝管、温度计和氮气导入管的四颈圆底烧瓶中,加热至150℃并继续搅拌2h。在减压下蒸馏出挥发性成分。获得226g由乙基亚膦酸和富马酸二甲酯形成的加合物,其含有13.1%的磷。氧杂-10-磷杂菲与富马酸二甲酯的加合物仅含有8.6%的磷。
实施例6
将150g乙基亚膦酸正丁酯(如实施例2中制备)和116g富马酸预置于217.4g丁醇中,并加热至沸腾。在搅拌下计量加入溶于130.4g丁醇的13.0g Wako V65B引发剂。在真空中蒸馏出溶剂。获得240g由乙基亚膦酸正丁酯和富马酸形成的加合物,其含有11.6%的磷。
实施例7
在氮气气氛下将158g衣康酸二甲酯加热至150℃,并在搅拌下计量加入150g乙基亚膦酸正丁酯(如实施例2中制备)。在减压下蒸馏出挥发性成分。获得296g由乙基亚膦酸正丁酯和衣康酸二甲酯形成的加合物,其含有10.4%的磷。
实施例8
将150g乙基亚膦酸正丁酯(如实施例2中制备)和242g衣康酸二丁酯在217.4g丁醇中加热至沸腾。在搅拌下计量加入溶于130g 丁醇的13g Wako V65B引发剂。在真空中蒸馏出溶剂。获得377g由乙基亚膦酸正丁酯和衣康酸二丁酯形成的加合物,其含有7.7%的磷。
实施例9
在配有温度计、回流冷凝管、搅拌器和滴液漏斗的五颈烧瓶中预置228g马来酸二丁酯和150g乙基亚膦酸正丁酯。在搅拌下如此快速地滴加5g丁醇钠(30%),使得温度不超过60℃,然后在真空中蒸馏出挥发性成分。获得363g由乙基亚膦酸正丁酯和马来酸二丁酯形成的加合物,其含有8.1%的磷。
实施例10
在反应容器中将94.1g乙基亚膦酸(如实施例1中制备)和98.1g马来酸酐于氮气气氛下加热至150℃,并进行反应。获得183g由乙基亚膦酸和马来酸酐形成的加合物。
实施例11
在反应容器中将150g乙基亚膦酸正丁酯(如实施例2中制备)和112g衣康酸酐于氮气气氛下加热至150℃,并进行反应。获得257g由乙基亚膦酸正丁酯和衣康酸酐形成的加合物,其含有11.5%的磷。
实施例12
将150g乙基亚膦酸正丁酯(如实施例2中制备)和108g苯醌加入400g 2-乙氧基乙醇中,并在搅拌下加热至70℃,继续搅拌并随后冷却。过滤出产物,用72ml 2-乙氧基乙醇和72ml甲醇洗涤并于130℃在真空中干燥。获得220g由乙基亚膦酸正丁酯和苯醌形成的加合物,其含有11.9%的磷。
实施例13
在高压搅拌釜中,将94.1g乙基亚膦酸(如实施例1中制备)和112g衣康酸酐加热至150℃,并在氮气气氛下进行反应。冷却后加入155g乙二醇和0.4g草酸钛钾并继续搅拌。通过抽真空蒸馏除去易挥发性成分。获得314g由乙基亚膦酸和衣康酸形成的加合物的乙二醇酯,其含有10%的磷。
实施例14
将94.1g乙基亚膦酸(如实施例1中制备)和116g马来酸装入配有搅拌器、冷凝管、温度计和氮气导入管的四颈圆底烧瓶中。在1h内于约90℃滴加16.4g 5%浓度的AIBN在乙二醇中的溶液。然后加入330g乙二醇并加热至200℃。在4h内以与乙二醇的混合物的方式蒸馏除去水。获得248g由乙基亚膦酸和马来酸形成的加合物的乙二醇酯,其含有12.5%的磷。
实施例15
将9.4g乙基亚膦酸(如实施例1中制备)和13g衣康酸装入配有搅拌器、冷凝管、温度计和氮气导入管的四颈圆底烧瓶中。将反应溶液于160℃加热1h。通过减压蒸馏将挥发性成分蒸馏除去。获得22g由乙基亚膦酸和衣康酸形成的加合物。
然后加入290g对苯二甲酸,188g乙二醇,0.29g乙酸钙,并在200℃加热2h。之后加入0.29g无水磷酸三钠和0.14g氧化锑(III),加热至280℃并在一小时内缓慢抽真空。该聚合物产物(420g)含有0.7%的磷,特性粘度为0.67,LOI为33.4。
实施例16
将94.1g乙基亚膦酸(如实施例1中制备)和13g衣康酸装入配有搅拌器、冷凝管、温度计和氮气导入管的四颈圆底烧瓶中。将反应溶液加热至160℃,并在减压下蒸馏除去挥发性成分。获得220g由乙基亚膦酸和衣康酸形成的加合物并转移至三颈烧瓶中。加入124g 乙二醇并在160℃排出酯化形成的水。向如此获得的反应产物的十分之一中加入290g对苯二甲酸,176g乙二醇,0.29g乙酸钙,并在200℃加热2h。然后加入0.29g无水磷酸三钠和0.14g氧化锑(III),加热至280℃,并之后在一小时内缓慢抽真空。该聚合物产物(约420g)含有0.7%的磷,特性粘度为0.68,LOI为32.1,未处理的聚对苯二甲酸乙二酯的LOI约为25。
实施例17
将9.41g乙基亚膦酸(如实施例1中制备)和11.6g马来酸装入配有搅拌器、冷凝管、温度计和氮气导入管的四颈圆底烧瓶中。将反应溶液于160℃加热1h并在减压下蒸馏除去挥发性成分。获得约19g由乙基亚膦酸和马来酸形成的加合物。然后加入367g对苯二甲酸二甲酯,238g 1,4-丁二醇,0.22g钛酸四丁酯和0.05g乙酸锂,并将该混合物首先在搅拌下于130至180℃加热2h,然后负压下加热至270℃。该聚合物产物(503g)含有0.6%的磷,特性粘度为0.96,LOI为35,未处理的聚对苯二甲酸丁二酯的LOI为23。
实施例18
将9.41g乙基亚膦酸(如实施例1中制备)和11.6g马来酸装入配有搅拌器、冷凝管、温度计和氮气导入管的四颈圆底烧瓶中。将反应溶液加热至160℃。减压下蒸馏除去挥发性成分。获得19g由乙基亚膦酸和马来酸形成的加合物,并转移至三颈烧瓶中。加入15.2g1,3-丙二醇,并在160℃蒸馏出酯化形成的水。然后加入367g对苯二甲酸二甲酯,186g 1,3-丙二醇,0.22g钛酸四丁酯和0.05g乙酸锂,并将混合物首先在搅拌下于130至180℃加热2h,然后负压下加热至270℃。该聚合物产物(480g)含有0.6%的磷,特性粘度为0.94,LOI为37。
实施例19
在配有温度计、回流冷凝管、搅拌器和滴液漏斗的五颈烧瓶中预置228g马来酸二丁酯和150g乙基亚膦酸正丁酯(如实施例2中制备)。在搅拌下如此快速地滴加5g丁醇钠(30%),使得温度不超过60℃。将其继续反应30min,并在真空中蒸馏除去易挥发性成分。然后加入几滴浓盐酸和235g水并回流加热。通过添加另外的60g水缓慢地蒸馏除去丁醇,并获得195g乙基亚膦酸和马来酸的加合物。
实施例20(环氧树脂的制备)
在配有回流冷凝管、搅拌器、温度计和氮气导入管的250ml五颈烧瓶中,将100g具有0.55mol/100g的环氧值的双酚A二缩水甘油醚(Beckopox EP 140,Solutia公司)和30g(0.134mol)由乙基次膦酸和衣康酸形成的加合物(如实施例3中制备)在搅拌下加热至最高150℃。30min后产生透明的熔体。在150℃再搅拌一小时后将熔体冷却并研磨。获得124.8g白色粉末形式的阻燃性环氧树脂,其具有3.2重量%的磷含量。
实施例21(UP树脂的制备)
在配有搅拌器、分水器、温度计、回流冷凝管和氮气导入管的21烧瓶中,将29.36g邻苯二甲酸酐,19.6g马来酸酐,15.2g丙二醇,25.3g由乙基亚膦酸和衣康酸形成的加合物(如实施例3中制备)的二(2-羟乙基)酯,20g二甲苯和50mg氢醌在搅拌下和通入氮气下加热至100℃。当放热反应开始时除去加热。反应减弱后在约190℃继续搅拌。分离出14g水后,蒸馏除去二甲苯,并获得88g阻燃性UP树脂。
使用的试剂
Claims (8)
1.用于制备烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)的加合物的无卤素的方法,
A-P(=O)(OX)-H (I)
其中,
A是乙基、正丙基、异丙基、正丁基、异丁基、正戊基、异戊基、正己基、异己基、2-苯基乙基、1-苯基乙基、3-苯基丙基、2-苯基丙基、2-羟基乙基、3-羟基丙基、2-羧基乙基、3-羧基丙基、2-乙酸基乙基、3-乙酸基丙基、2-丁酸基乙基、3-丁酸基丙基、2-乙氧基乙基、3-乙氧基丙基、2-丙氧基乙基、3-丙氧基丙基、2-丁氧基乙基、3-丁氧基丙基、3-羧基丙基、2-氨基乙基和/或3-氨基丙基;
和
X表示氢、甲基、乙基、丙基、丁基、戊基、辛基、乙基己基、乙二醇基、丙二醇基、丁二醇基、苄基、苯基、乙烯基和/或烯丙基,锂、钠、钾、镁、钙、钡、铝、铅、钛、铁、锌、铵、苯铵、三甲基铵、三乙基铵、三丙基铵、三丁基铵、四甲基铵、四乙基铵、四丙基铵、四丁基铵、三甲基甲硅烷基铵或N-乙基哌啶,
其中,
R2、R4相同或不同并表示CO2H、CO2R5、R6-CO2H、R6-CO2R5,且
R1、R3相同或不同并表示H、R5;或者
R1、R4相同或不同并表示CO2H、CO2R5、R6-CO2H、R6-CO2R5,且
R2、R3相同或不同并表示H、R5;或者
R2、R4相同或不同并表示-CO-O-CO-、-CO-S-CO-、-CO-NR1-CO-、-CO-PR1-CO-,且R1、R3相同或不同并表示H、R5;或者
R1、R2相同或不同并表示CO2H、CN、CO2R5、R6-CO2H、R6-CO2R5,且
R3、R4相同或不同并表示H、R5;或者
R1、R2相同或不同并表示-CR2 3-CO-O-CO-、-CR2 3-CO-NR1-CO-、-CR2 3-CO-O-CO-CR2 3、-CR2 3-CO-NR1-CO-CR2 3,且R3、R4相同或不同并表示H、R5;或者
R2和R4各自表示-CO-CR5=CR5-CO-,且R1、R3相同或不同并表示H、R5;
R5表示C1-C18烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基;
R6表示C2-C18-亚烷基、C6-C18-亚芳基、C6-C18-烷亚芳基和/或C6-C18-芳亚烷基;
所述方法包括:
a)将次膦酸源与不可形成二酯的烯烃(III)在催化剂A的存在下反应成烷基亚膦酸衍生物(I),
其中,R7至R10相同或不同,且表示H、C1-C18烷基、C6-C18-芳基或C2-C18烯基,
b)使如此获得的烷基亚膦酸衍生物(I)与可形成二酯的烯烃(II)在催化剂B的存在下反应生成加合物,
其中
催化剂A是过渡金属、过渡金属化合物和/或催化剂体系,其由过渡金属和/或过渡金属化合物和至少一种配体构成,其中所述过渡金属和/或过渡金属化合物是铑、镍、钯、钌和/或铂,和
催化剂B是可形成过氧化物的化合物、过氧化合物、偶氮化合物、碱金属、碱土金属、碱金属氢化物、碱土金属氢化物和/或碱金属醇化物、碱土金属醇化物,
其中可形成二酯的烯烃是马来酸、富马酸、衣康酸、苯基亚甲基丙二酸,它们的二甲酯、二乙酯、二丙酯、二异丙酯和二丁酯,苯醌或萘醌,以及其中不可形成二酯的烯烃(III)是乙烯、1-丙烯、1-丁烯、1-戊烯和/或1-己烯。
2.根据权利要求1的方法,其特征在于,次膦酸源是次膦酸、次膦酸的盐、次膦酸的酯或它们的混合物。
3.根据权利要求1或2的方法,其特征在于,催化剂B是过氧化氢、过氧化钠、过氧化锂、过硫酸钾、过硫酸钠、过硫酸铵、过二硫酸钠、过硼酸钾、过氧乙酸、过氧化苯甲酰、二叔丁基过氧化物、和/或过二硫酸,和/或是偶氮二异丁腈、2,2′-偶氮双(2-脒基丙烷)-二盐酸盐和/或2,2′-偶氮双(N,N′-二亚甲基-异丁酰脒)-二盐酸盐,和/或是锂、氢化锂、氢化铝锂、甲基锂、丁基锂、叔丁基锂、二异丙基氨基锂、钠、氢化钠、硼氢化钠、甲醇钠、乙醇钠或丁醇钠、甲醇钾、乙醇钾和/或丁醇钾。
4.根据权利要求1的方法,其特征在于,将步骤b)之后由烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)获得的反应产物在步骤c)中与成酯剂反应。
5.根据权利要求4的方法,其特征在于,成酯剂是C1-C20饱和的和不饱和的一元、二元、三元和四元醇。
6.根据权利要求4或5的方法,其特征在于,成酯剂是甲醇、乙醇、丙醇、丁醇、戊醇、辛醇、乙二醇、聚乙二醇、1,2-丙二醇、1,3-丙二醇、丁二醇、甘油、赤藓糖醇、季戊四醇、烯丙醇、3-丁烯-1-醇、3-羟基-1-丁烯、3-丁烯-2-醇、甲基乙烯基甲醇、2-甲基-2-丙烯-1-醇、甲基烯丙醇、2-丁烯-1-醇、巴豆醇、1-戊烯-3-醇、反-2-戊烯-1-醇、顺-2-戊烯-1-醇、3-戊烯-2-醇、4-戊烯-1-醇、4-戊烯-2-醇、1-己烯-3-醇、顺-2-己烯-1-醇、反-2-己烯-1-醇、顺-3-己烯-1-醇、反-3-己烯-1-醇、4-己烯-1-醇、5-己烯-1-醇、5-己烯-2-醇、1-庚烯-3-醇、1-辛烯-3-醇、反-2-辛烯-1-醇、油醇、萜烯醇、炔丙醇和/或2-丁炔-1,4-二醇。
7.根据权利要求1或2的方法,其特征在于,将步骤b)之后由烷基亚膦酸衍生物(I)和可形成二酯的烯烃(II)获得的反应产物与催化剂C反应。
8.根据权利要求7的方法,其特征在于,催化剂C是布朗斯台德酸、布朗斯台德碱、水、无机酸、磺酸、碱金属氢氧化物和/或碱土金属氢氧化物。
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2008
- 2008-12-19 DE DE102008064012A patent/DE102008064012A1/de not_active Withdrawn
-
2009
- 2009-10-06 CN CN201310654932.3A patent/CN103665031A/zh active Pending
- 2009-10-06 US US13/140,563 patent/US8592505B2/en not_active Expired - Fee Related
- 2009-10-06 CN CN200980138912.2A patent/CN102171230B/zh not_active Expired - Fee Related
- 2009-10-06 EP EP09740265.5A patent/EP2379575B1/de not_active Expired - Fee Related
- 2009-10-06 ES ES09740265.5T patent/ES2629852T3/es active Active
- 2009-10-06 WO PCT/EP2009/007145 patent/WO2010069421A1/de active Application Filing
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US6090968A (en) * | 1998-06-29 | 2000-07-18 | Clariant Gmbh | Process for preparing phosphinic esters |
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US20110251310A1 (en) | 2011-10-13 |
CN102171230A (zh) | 2011-08-31 |
WO2010069421A1 (de) | 2010-06-24 |
US8592505B2 (en) | 2013-11-26 |
DE102008064012A1 (de) | 2010-06-24 |
CN103665031A (zh) | 2014-03-26 |
JP2012512198A (ja) | 2012-05-31 |
ES2629852T3 (es) | 2017-08-16 |
EP2379575A1 (de) | 2011-10-26 |
JP5641658B2 (ja) | 2014-12-17 |
EP2379575B1 (de) | 2017-04-12 |
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