TW201335171A - 至少一種二烷膦酸與至少一種其他不同的二烷膦酸之混合物、彼之製法及彼之用途 - Google Patents
至少一種二烷膦酸與至少一種其他不同的二烷膦酸之混合物、彼之製法及彼之用途 Download PDFInfo
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- TW201335171A TW201335171A TW101142473A TW101142473A TW201335171A TW 201335171 A TW201335171 A TW 201335171A TW 101142473 A TW101142473 A TW 101142473A TW 101142473 A TW101142473 A TW 101142473A TW 201335171 A TW201335171 A TW 201335171A
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- acid
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- formula
- dialkylphosphonic
- mixture
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- 239000002253 acid Substances 0.000 title claims abstract description 151
- 239000000203 mixture Substances 0.000 title claims abstract description 120
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims abstract description 4
- 229920000642 polymer Polymers 0.000 claims description 76
- -1 nitrogen-containing compound Chemical class 0.000 claims description 59
- MJUJXFBTEFXVKU-UHFFFAOYSA-N diethyl phosphonate Chemical compound CCOP(=O)OCC MJUJXFBTEFXVKU-UHFFFAOYSA-N 0.000 claims description 40
- DEKKNVOOBDLURO-UHFFFAOYSA-N hexan-2-ylphosphonic acid Chemical compound CCCCC(C)P(O)(O)=O DEKKNVOOBDLURO-UHFFFAOYSA-N 0.000 claims description 37
- 238000000465 moulding Methods 0.000 claims description 34
- AHXZGOMBHYIOMA-UHFFFAOYSA-N heptan-3-ylphosphonic acid Chemical compound CCC(CCCC)P(O)(O)=O AHXZGOMBHYIOMA-UHFFFAOYSA-N 0.000 claims description 29
- VLNACYCQXLHHJP-UHFFFAOYSA-N hexan-3-ylphosphonic acid Chemical compound CCCC(CC)P(O)(O)=O VLNACYCQXLHHJP-UHFFFAOYSA-N 0.000 claims description 28
- XPLOQMVUXWZLET-UHFFFAOYSA-N n-hexylphosphonate ethyl ester Chemical compound CCCCCC[P@@](O)(=O)OCC XPLOQMVUXWZLET-UHFFFAOYSA-N 0.000 claims description 28
- MNSRFSRDBLNETM-UHFFFAOYSA-N heptan-4-ylphosphonic acid Chemical compound CCCC(P(O)(O)=O)CCC MNSRFSRDBLNETM-UHFFFAOYSA-N 0.000 claims description 27
- 239000003063 flame retardant Substances 0.000 claims description 25
- OMDMJIAMNPLNSN-UHFFFAOYSA-N pentan-3-ylphosphonic acid Chemical compound CCC(CC)P(O)(O)=O OMDMJIAMNPLNSN-UHFFFAOYSA-N 0.000 claims description 25
- 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 24
- PVBGKAMVCZUNFQ-UHFFFAOYSA-N 1-propoxyphosphonoyloxypropane Chemical compound CCCOP(=O)OCCC PVBGKAMVCZUNFQ-UHFFFAOYSA-N 0.000 claims description 22
- CHHAABPEARTNDD-UHFFFAOYSA-N decan-5-ylphosphonic acid Chemical compound CCCCCC(P(O)(O)=O)CCCC CHHAABPEARTNDD-UHFFFAOYSA-N 0.000 claims description 22
- BXRPMFQIBGNELU-UHFFFAOYSA-N CCCCC(P(O)(O)=O)CCC Chemical compound CCCCC(P(O)(O)=O)CCC BXRPMFQIBGNELU-UHFFFAOYSA-N 0.000 claims description 21
- YVOCEKGQGPCOQB-UHFFFAOYSA-N nonan-4-ylphosphonic acid Chemical compound C(CC)C(CCCCC)P(O)(O)=O YVOCEKGQGPCOQB-UHFFFAOYSA-N 0.000 claims description 21
- GKIQHTGBORJXKZ-UHFFFAOYSA-N undecylphosphonic acid Chemical compound CCCCCCCCCCCP(O)(O)=O GKIQHTGBORJXKZ-UHFFFAOYSA-N 0.000 claims description 21
- GOIKRCUXPMCDRL-UHFFFAOYSA-N CCCCC(P(O)(O)=O)CCCC Chemical compound CCCCC(P(O)(O)=O)CCCC GOIKRCUXPMCDRL-UHFFFAOYSA-N 0.000 claims description 20
- 239000003822 epoxy resin Substances 0.000 claims description 16
- 229920000647 polyepoxide Polymers 0.000 claims description 16
- 229920001187 thermosetting polymer Polymers 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 229920001169 thermoplastic Polymers 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 239000004634 thermosetting polymer Substances 0.000 claims description 10
- 239000004416 thermosoftening plastic Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
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- 239000001205 polyphosphate Substances 0.000 claims description 7
- 235000011176 polyphosphates Nutrition 0.000 claims description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- 239000000945 filler 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
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 4
- 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 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012779 reinforcing material Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 3
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims description 3
- 150000001463 antimony compounds Chemical class 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 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 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 3
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- KCHNMIKAMRQBHD-UHFFFAOYSA-N 1-hydroperoxypentane Chemical group CCCCCOO KCHNMIKAMRQBHD-UHFFFAOYSA-N 0.000 claims description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 claims description 2
- TVWBTVJBDFTVOW-UHFFFAOYSA-N 2-methyl-1-(2-methylpropylperoxy)propane Chemical compound CC(C)COOCC(C)C TVWBTVJBDFTVOW-UHFFFAOYSA-N 0.000 claims description 2
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 claims description 2
- FRZFZMDQKDAJRJ-UHFFFAOYSA-N 6-methyldecan-1-amine Chemical compound CCCCC(C)CCCCCN FRZFZMDQKDAJRJ-UHFFFAOYSA-N 0.000 claims description 2
- YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 claims description 2
- PFPSOZSOSPOAPX-UHFFFAOYSA-N 7-(7-oxoazepane-2-carbonyl)azepan-2-one Chemical compound C1CCCC(=O)NC1C(=O)C1CCCCC(=O)N1 PFPSOZSOSPOAPX-UHFFFAOYSA-N 0.000 claims description 2
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- BUZAHHWYIYJFDZ-UHFFFAOYSA-N NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(=O)OP(O)(O)=O Chemical compound NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(=O)OP(O)(O)=O BUZAHHWYIYJFDZ-UHFFFAOYSA-N 0.000 claims description 2
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- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims description 2
- FDJZNXLKZOXHPN-UHFFFAOYSA-N [hydroxy(phosphonooxy)phosphoryl] phosphono hydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O FDJZNXLKZOXHPN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 229960000458 allantoin Drugs 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- OXIACMHTSQNJCY-UHFFFAOYSA-N bis[hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate 1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(=O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)O.N1=C(N)N=C(N)N=C1N OXIACMHTSQNJCY-UHFFFAOYSA-N 0.000 claims description 2
- 229910001593 boehmite Inorganic materials 0.000 claims description 2
- IUTYMBRQELGIRS-UHFFFAOYSA-N boric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OB(O)O.NC1=NC(N)=NC(N)=N1 IUTYMBRQELGIRS-UHFFFAOYSA-N 0.000 claims description 2
- FSRYENDEMMDKMT-UHFFFAOYSA-N butoxy ethaneperoxoate Chemical group CCCCOOOC(C)=O FSRYENDEMMDKMT-UHFFFAOYSA-N 0.000 claims description 2
- ZGPBOPXFOJBLIV-UHFFFAOYSA-N butoxycarbonyloxy butyl carbonate Chemical group CCCCOC(=O)OOC(=O)OCCCC ZGPBOPXFOJBLIV-UHFFFAOYSA-N 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
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- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 claims description 2
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- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 2
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- 239000013067 intermediate product Substances 0.000 claims description 2
- 150000002681 magnesium compounds Chemical class 0.000 claims description 2
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- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 claims description 2
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- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 claims description 2
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- SIGUVTURIMRFDD-UHFFFAOYSA-M sodium dioxidophosphanium Chemical compound [Na+].[O-][PH2]=O SIGUVTURIMRFDD-UHFFFAOYSA-M 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
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- 238000003786 synthesis reaction Methods 0.000 claims description 2
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims description 2
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- KHKSXAYMYFVLBL-UHFFFAOYSA-N tris(phosphanyl) phosphate Chemical compound POP(=O)(OP)OP KHKSXAYMYFVLBL-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
本發明係關於一種至少一種式(I)的二烷膦酸與至少一種不同之式(II)的二烷膦酸之混合物□其中R1,R2 相同或不同且各自為C1-C18-烷基、C2-C18-烯基、C6-C18-芳基、C7-C18-烷芳基,□其中R3,R4 相同或不同且各自為C1-C18-烷基、C2-C18-烯基、C6-C18-芳基和/或C7-C18-烷芳基,先決條件是R3和R4基團中之至少一者不同於R1和R2;及彼等之製法和其用途。
Description
本發明係關於至少一種二烷膦酸與至少一種其他不同的二烷膦酸之混合物、彼之製法及彼之用途。
在日益增進地應用於各種裝置(例如,電腦、相機、行動電話、LCD和TFT螢幕及其他電子裝置)的印刷電路板之製造中,使用不同材料,特別是聚合物。這些特別包括熱固性材料、玻璃纖維強化的熱固性材料和熱塑性材料。由於環氧樹脂的良好性質,所以彼等特別常被使用。
根據相關標準(IPC-4101,Specification for Base Materials for Rigid and Multilayer Printed Boards),這些印刷電路板必須被賦予阻燃性。
印刷電路板在其製造期間內的熱膨脹是一個問題。印刷電路板的電子產品製造商的條件要求印刷電路板耐受高熱應力且不會受損或變形。導電跡線(無鉛焊料)施於印刷電路板係於高至約260℃的溫度進行。因此,重要的是,印刷電路板於熱應力下不捲曲且產品維持尺寸安定。
即使在預浸體(“預浸漬的纖維”的簡稱)和積層物的情況中,熱膨脹特別明顯,由於這些材料構成印刷電路板的初步形式或前驅物所致。
因此,重要的是,儘量降低試樣的熱膨脹以得到良好之尺寸安定的產物(例如經完成的印刷電路板)。
因此,本發明的目的係使用於預浸物、印刷電路板和積層物的聚合物改性,使得它們的熱膨脹僅極低(若有的話)並滿足尺寸安定性。
藉一種至少一種式(I)的二烷膦酸(dialkylphosphinic acid)與至少一種不同之式(II)的二烷膦酸之混合物達到此目的
其中R1,R2 相同或不同且各自為C1-C18-烷基、C2-C18-烯基、C6-C18-芳基、C7-C18-烷芳基,
其中R3,R4 相同或不同且各自為C1-C18-烷基、C2-C18-烯基、C6-C18-芳基和/或C7-C18-烷芳基,先決條件是R3和R4基團中之至少一者不同於R1和R2。
較佳地,R1和R2相同或不同且各自為甲基、乙基、正丙基、異丙基、正丁基、異丁基、三級丁基、正戊基、異戊基、正己基、異己基和/或苯基。
較佳地,R3和R4相同或不同且各自為甲基、乙基、正丙基、異丙基、正丁基、異丁基、三級丁基、正戊基、異戊基、正己基、異己基和/或苯基,先決條件是R3和R4基團中之至少一者不同於R1和R2。
較佳地,該混合物包含0.1至99.9重量%式(I)的二烷膦酸和99.9至0.1重量%不同之式(II)的二烷膦酸。
更佳地,該混合物包含40至99.9重量%式(I)的二烷膦酸和60至0.1重量%不同之式(II)的二烷膦酸。
另較佳地,該混合物包含60至99.9重量%式(I)的二烷膦酸和40至0.1重量%不同之式(II)的二烷膦酸。
亦較佳地,該混合物包含80至99.9重量%式(I)的二烷膦酸和20至0.1重量%不同之式(II)的二烷膦酸。
同樣較佳地,該混合物包含90至99.9重量%式(I)的二烷膦酸和10至0.1重量%不同之式(II)的二烷膦酸。
另較佳地,該混合物包含95至99.9重量%式(I)的二烷膦酸和5至0.1重量%不同之式(II)的二烷膦酸。
但特別佳地,該混合物包含98至99.9重量%式(I)的二烷膦酸和2至0.1重量%不同之式(II)的二烷膦酸。
較佳地,該二烷膦酸係二乙基膦酸、乙基丙基膦酸、乙基丁基膦酸、乙基戊基膦酸、乙基己基膦酸、二丙基膦酸、丙基丁基膦酸、丙基戊基膦酸、丙基己基膦酸、二丁
基膦酸、丁基戊基膦酸、丁基己基膦酸、二戊基膦酸、戊基己基膦酸和/或二己基膦酸。
根據本發明,特別佳的混合物包含98至99.9重量%的二乙基膦酸和2至0.1重量%的丁基乙基膦酸。
本發明之混合物較佳地另包含至少一種增效劑,而該增效劑為含氮化合物,例如蜜勒胺(melem)、蜜白胺(melam)、三聚二氰亞胺(melon)、三聚氰胺(melamine)硼酸鹽、三聚氰胺三聚氰酸鹽、三聚氰胺磷酸鹽、二(三聚氰胺)磷酸鹽、五(三聚氰胺)三磷酸鹽、三(三聚氰胺)二磷酸鹽、肆(三聚氰胺)三磷酸鹽、陸(三聚氰胺)五磷酸鹽、三聚氰胺二磷酸鹽、三聚氰胺四磷酸鹽、三聚氰胺焦磷酸鹽、三聚氰胺聚磷酸鹽、蜜白胺聚磷酸鹽、蜜勒胺聚磷酸鹽和/或三聚二氰亞胺聚磷酸鹽;鋁化合物,如氫氧化鋁、多水高嶺土(halloysite)、藍寶石產物、水鋁土(boehmite)、奈水鋁土(nanoboehmite);鎂化合物,如氫氧化鎂;錫化合物,如氧化錫;銻化合物,如氧化銻;鋅化合物,如氧化鋅、氫氧化鋅、氧化鋅水合物、碳酸鋅、錫酸鋅、羥基錫酸鋅、矽酸鋅、磷酸鋅、硼磷酸鋅、硼酸鋅和/或鉬酸鋅;矽化合物,如矽酸鹽和/或聚矽氧;磷化合物,如亞膦酸(phosphinic acid)和彼等的鹽、膦酸(phosphonic acid)和彼等的鹽和/或膦氧化物、膦氮烯
(phosphazene)和/或哌(焦)磷酸鹽;碳化二醯亞胺、哌、(聚)異氰酸酯、苯乙烯-丙烯酸系聚合物;和/或羰基雙己內醯胺;得自參(羥乙基)三聚異氰酸酯與芳族多羧酸的低聚酯之氮化合物、或6-苯基胍胺(benzoguguanamine)、6-甲基胍胺(acetoguanamine)、參(羥乙基)三聚異氰酸酯、乙內醯脲(allantoin)、甘脲(glycoluril)、三聚氰酸酯、三聚氰酸酯-環氧化物化合物、脲三聚氰酸酯、二氰醯胺、胍、胍磷酸鹽和/或硫酸鹽。
該混合物較佳地包含99至1重量%如申請專利範圍第1至7項中至少一項之至少一種式(I)的二烷膦酸和至少一種不同之式(II)的二烷膦酸之混合物及1至99重量%增效劑。
本發明亦係關於一種製造如申請專利範圍第1至12項中任一項之混合物的方法,其包含令磷來源與引發劑和烯烴反應及以無機酸處理所得者,並藉由濃縮和處理而令其轉化成至少一種式(I)的二烷膦酸和至少一種不同之式(II)的二烷膦酸之混合物。
較佳地,該磷來源係亞膦酸鹽,該烯烴係乙烯,該無機酸係硫酸或氫氯酸,而該自由基引發劑係2,2’-偶氮基雙(2-脒基丙烷)二氫氯酸鹽、2,2’-偶氮基雙(N,N’-二伸甲基異丁脒)二氫氯酸鹽、偶氮基雙(異丁腈)、4,4’-偶氮基雙(4-氰基戊酸)和/或2,2’-偶氮基雙(2-甲基丁腈)或過氧化氫、過氧基二硫酸銨、過氧基二硫酸鉀、二苄醯過氧化物
、二-三級丁基過氧化物、過乙酸、二異丁基過氧化物、過氧基新癸酸異丙苯酯、過氧基新癸酸三級丁酯、過氧基三級戊酸三級丁酯、過氧基三級戊酸三級戊酯、過氧基二碳酸二丙酯、過氧基二碳酸二丁酯、過氧基二碳酸二肉豆蔻酯、二月桂醯過氧化物、過氧基-2-乙基己酸1,1,3,3-四甲基丁酯、過氧基-2-乙基己基碳酸三級戊酯、過氧基異丁酸三級戊酯、1,1-二(三級丁基過氧基)環己烷、過氧基苯甲酸三級丁酯、過氧基乙酸三級丁酯、過氧基二乙基乙酸三級丁酯、過氧基異丙基碳酸三級丁酯、2,2-二(三級丁基過氧基)丁烷、三級戊基氫過氧化物和/或2,5-二甲基-2,5-二(三級丁基過氧基)己烷。
較佳地,該方法的實施方式係令亞膦酸鈉與乙烯反應之後與稀硫酸反應,濃縮,過濾和蒸餾,以得到二乙基膦酸與丁基乙基膦酸之混合物。
較佳地,該反應發生於溶劑中,且該溶劑係醇、酸或水。
較佳地,該反應溫度介於50和150℃之間。
本發明亦含括如申請專利範圍第1至12項中任一項之混合物之用途,其係作為用於進一步合成的中間產物,作為黏合劑,在環氧樹脂、聚胺甲酸酯和不飽和聚酯樹脂之固化中作為交聯劑或加速劑,作為聚合物安定劑,作為作物保護組成物,作為螯合劑,作為礦油添加劑,作為抗腐蝕劑,用於清洗和清潔組成物應用及用於電子應用。
更特別地,本發明含括如申請專利範圍第1至14項
中任一項之混合物之用途,其係用作為阻燃劑,特別是作為透明塗層和泡脹塗層的阻燃劑,作為木材和其他纖維素產品的阻燃劑,作為聚合物的反應性和/或非反應性阻燃劑,用以製造阻燃性聚合物模塑組成物,用以製造阻燃性聚合物模塑物和/或用以藉由浸滲而賦予聚酯及純和摻合的纖維素織品阻燃性,及作為增效劑。
本發明亦係關於一種阻燃性熱塑性或熱固性聚合物模塑組成物以及聚合物模塑物、膜、纖絲或纖維,其包含0.5至45重量%如申請專利範圍第1至14項中任一項之混合物、0.5至99.5重量%熱塑性或熱固性聚合物或彼等之混合物、0至55重量%添加劑和0至55重量%填料或強化材料,其中組份的總和為100重量%。
最後,本發明亦係關於一種阻燃性熱塑性或熱固性聚合物模塑組成物以及聚合物模塑物、膜、纖絲或纖維,其包含1至30重量%如申請專利範圍第1至14項中任一項之混合物、10至95重量%熱塑性或熱固性聚合物或彼等之混合物、2至30重量%添加劑和2至30重量%填料或強化材料,其中組份的總和為100重量%。
本發明主張含有至少一種式(I)的二烷膦酸與至少一種不同之式(II)的二烷膦酸之混合物,先決條件是R3和R4基團中之至少一者不同於R1和R2。此意謂R3或R4不同於R1和R2,或二者皆不同,即,R3和R4不同於R1和R2。
至少一種式(I)的二烷膦酸與至少一種不同之式(II)的
二烷膦酸之較佳混合物由以下者所構成:二甲基膦酸和甲基乙基膦酸,二甲基膦酸和甲基丙基膦酸,二甲基膦酸和甲基丁基膦酸,二甲基膦酸和甲基戊基膦酸,二甲基膦酸和甲基己基膦酸,二甲基膦酸和乙基乙基膦酸,二甲基膦酸和乙基丙基膦酸,二甲基膦酸和乙基丁基膦酸,二甲基膦酸和乙基戊基膦酸,二甲基膦酸和乙基己基膦酸,二甲基膦酸和丙基丙基膦酸,二甲基膦酸和丙基丁基膦酸,二甲基膦酸和丙基戊基膦酸,二甲基膦酸和丙基己基膦酸,二甲基膦酸和丁基丁基膦酸,二甲基膦酸和丁基戊基膦酸,二甲基膦酸和丁基己基膦酸,二甲基膦酸和戊基戊基膦酸,二甲基膦酸和戊基己基膦酸,二甲基膦酸和己基己基膦酸,二乙基膦酸和甲基乙基膦酸,二乙基膦酸和甲基丙基膦酸,二乙基膦酸和甲基丁基膦酸,
二乙基膦酸和甲基戊基膦酸,二乙基膦酸和甲基己基膦酸,二乙基膦酸和乙基丙基膦酸,二乙基膦酸和乙基丁基膦酸,二乙基膦酸和乙基戊基膦酸,二乙基膦酸和乙基己基膦酸,二乙基膦酸和丙基丙基膦酸,二乙基膦酸和丙基丁基膦酸,二乙基膦酸和丙基戊基膦酸,二乙基膦酸和丙基己基膦酸,二乙基膦酸和丁基丁基膦酸,二乙基膦酸和丁基戊基膦酸,二乙基膦酸和丁基己基膦酸,二乙基膦酸和戊基戊基膦酸,二乙基膦酸和戊基己基膦酸,二乙基膦酸和己基己基膦酸,二丙基膦酸和甲基乙基膦酸,二丙基膦酸和甲基丙基膦酸,二丙基膦酸和甲基丁基膦酸,二丙基膦酸和甲基戊基膦酸,二丙基膦酸和甲基己基膦酸,二丙基膦酸和乙基丙基膦酸,二丙基膦酸和乙基丁基膦酸,二丙基膦酸和乙基戊基膦酸,
二丙基膦酸和乙基己基膦酸,二丙基膦酸和丙基丁基膦酸,二丙基膦酸和丙基戊基膦酸,二丙基膦酸和丙基己基膦酸,二丙基膦酸和丁基丁基膦酸,二丙基膦酸和丁基戊基膦酸,二丙基膦酸和丁基己基膦酸,二丙基膦酸和戊基戊基膦酸,二丙基膦酸和戊基己基膦酸,二丙基膦酸和己基己基膦酸,二丁基膦酸和甲基乙基膦酸,二丁基膦酸和甲基丙基膦酸,二丁基膦酸和甲基丁基膦酸,二丁基膦酸和甲基戊基膦酸,二丁基膦酸和甲基己基膦酸,二丁基膦酸和乙基丙基膦酸,二丁基膦酸和乙基丁基膦酸,二丁基膦酸和乙基戊基膦酸,二丁基膦酸和乙基己基膦酸,二丁基膦酸和丙基丁基膦酸,二丁基膦酸和丙基戊基膦酸,二丁基膦酸和丙基己基膦酸,二丁基膦酸和丁基戊基膦酸,二丁基膦酸和丁基己基膦酸,
二丁基膦酸和戊基戊基膦酸,二丁基膦酸和戊基己基膦酸,二丁基膦酸和己基己基膦酸,二戊基膦酸和甲基乙基膦酸,二戊基膦酸和甲基丙基膦酸,二戊基膦酸和甲基丁基膦酸,二戊基膦酸和甲基戊基膦酸,二戊基膦酸和甲基己基膦酸,二戊基膦酸和乙基丙基膦酸,二戊基膦酸和乙基丁基膦酸,二戊基膦酸和乙基戊基膦酸,二戊基膦酸和乙基己基膦酸,二戊基膦酸和丙基丁基膦酸,二戊基膦酸和丙基戊基膦酸,二戊基膦酸和丙基己基膦酸,二戊基膦酸和丁基戊基膦酸,二戊基膦酸和丁基己基膦酸,二戊基膦酸和戊基己基膦酸,二戊基膦酸和己基己基膦酸,二己基膦酸和甲基乙基膦酸,二己基膦酸和甲基丙基膦酸,二己基膦酸和甲基丁基膦酸,二己基膦酸和甲基戊基膦酸,二己基膦酸和甲基己基膦酸,
二己基膦酸和乙基丙基膦酸,二己基膦酸和乙基丁基膦酸,二己基膦酸和乙基戊基膦酸,二己基膦酸和乙基己基膦酸,二己基膦酸和丙基丁基膦酸,二己基膦酸和丙基戊基膦酸,二己基膦酸和丙基己基膦酸,二己基膦酸和丁基戊基膦酸,二己基膦酸和丁基己基膦酸,二己基膦酸和戊基己基膦酸,甲基乙基膦酸和甲基丙基膦酸,甲基乙基膦酸和甲基丁基膦酸,甲基乙基膦酸和甲基戊基膦酸,甲基乙基膦酸和甲基己基膦酸,甲基乙基膦酸和乙基丙基膦酸,甲基乙基膦酸和乙基丁基膦酸,甲基乙基膦酸和乙基戊基膦酸,甲基乙基膦酸和乙基己基膦酸,甲基乙基膦酸和丙基丁基膦酸,甲基乙基膦酸和丙基戊基膦酸,甲基乙基膦酸和丙基己基膦酸,甲基乙基膦酸和丁基戊基膦酸,甲基乙基膦酸和丁基己基膦酸,甲基乙基膦酸和戊基己基膦酸,
甲基丙基膦酸和甲基丁基膦酸,甲基丙基膦酸和甲基戊基膦酸,甲基丙基膦酸和甲基己基膦酸,甲基丙基膦酸和乙基丙基膦酸,甲基丙基膦酸和乙基丁基膦酸,甲基丙基膦酸和乙基戊基膦酸,甲基丙基膦酸和乙基己基膦酸,甲基丙基膦酸和丙基丁基膦酸,甲基丙基膦酸和丙基戊基膦酸,甲基丙基膦酸和丙基己基膦酸,甲基丙基膦酸和丁基戊基膦酸,甲基丙基膦酸和丁基己基膦酸,甲基丙基膦酸和戊基己基膦酸,甲基丁基膦酸和甲基戊基膦酸,甲基丁基膦酸和甲基己基膦酸,甲基丁基膦酸和乙基丙基膦酸,甲基丁基膦酸和乙基丁基膦酸,甲基丁基膦酸和乙基戊基膦酸,甲基丁基膦酸和乙基己基膦酸,甲基丁基膦酸和丙基丁基膦酸,甲基丁基膦酸和丙基戊基膦酸,甲基丁基膦酸和丙基己基膦酸,甲基丁基膦酸和丁基戊基膦酸,甲基丁基膦酸和丁基己基膦酸,
甲基丁基膦酸和戊基己基膦酸,甲基戊基膦酸和甲基己基膦酸,甲基戊基膦酸和乙基丙基膦酸,甲基戊基膦酸和乙基丁基膦酸,甲基戊基膦酸和乙基戊基膦酸,甲基戊基膦酸和乙基己基膦酸,甲基戊基膦酸和丙基丁基膦酸,甲基戊基膦酸和丙基戊基膦酸,甲基戊基膦酸和丙基己基膦酸,甲基戊基膦酸和丁基戊基膦酸,甲基戊基膦酸和丁基己基膦酸,甲基戊基膦酸和戊基己基膦酸,甲基己基膦酸和乙基丙基膦酸,甲基己基膦酸和乙基丁基膦酸,甲基己基膦酸和乙基戊基膦酸,甲基己基膦酸和乙基己基膦酸,甲基己基膦酸和丙基丁基膦酸,甲基己基膦酸和丙基戊基膦酸,甲基己基膦酸和丙基己基膦酸,甲基己基膦酸和丁基戊基膦酸,甲基己基膦酸和丁基己基膦酸,甲基己基膦酸和戊基己基膦酸,乙基丙基膦酸和乙基丁基膦酸,乙基丙基膦酸和乙基戊基膦酸,
乙基丙基膦酸和乙基己基膦酸,乙基丙基膦酸和丙基丁基膦酸,乙基丙基膦酸和丙基戊基膦酸,乙基丙基膦酸和丙基己基膦酸,乙基丙基膦酸和丁基戊基膦酸,乙基丙基膦酸和丁基己基膦酸,乙基丙基膦酸和戊基己基膦酸,乙基丁基膦酸和乙基丙基膦酸,乙基丁基膦酸和乙基戊基膦酸,乙基丁基膦酸和乙基己基膦酸,乙基丁基膦酸和丙基丁基膦酸,乙基丁基膦酸和丙基戊基膦酸,乙基丁基膦酸和丙基己基膦酸,乙基丁基膦酸和丁基丙基膦酸,乙基丁基膦酸和丁基戊基膦酸,乙基丁基膦酸和丁基己基膦酸,乙基丁基膦酸和戊基乙基膦酸,乙基丁基膦酸和戊基丙基膦酸,乙基丁基膦酸和戊基丁基膦酸,乙基丁基膦酸和戊基己基膦酸,乙基戊基膦酸和乙基丙基膦酸,乙基戊基膦酸和乙基丁基膦酸,乙基戊基膦酸和乙基己基膦酸,乙基戊基膦酸和丙基丁基膦酸,
乙基戊基膦酸和丙基戊基膦酸,乙基戊基膦酸和丙基己基膦酸,乙基戊基膦酸和丁基丙基膦酸,乙基戊基膦酸和丁基戊基膦酸,乙基戊基膦酸和丁基己基膦酸,乙基戊基膦酸和戊基丙基膦酸,乙基戊基膦酸和戊基丁基膦酸,乙基戊基膦酸和戊基己基膦酸,乙基己基膦酸和乙基丙基膦酸,乙基己基膦酸和乙基丁基膦酸,乙基己基膦酸和乙基己基膦酸,乙基己基膦酸和丙基丁基膦酸,乙基己基膦酸和丙基戊基膦酸,乙基己基膦酸和丙基己基膦酸,乙基己基膦酸和丁基丙基膦酸,乙基己基膦酸和丁基戊基膦酸,乙基己基膦酸和丁基己基膦酸,乙基己基膦酸和戊基丙基膦酸,乙基己基膦酸和戊基丁基膦酸,乙基己基膦酸和戊基己基膦酸,丙基丁基膦酸和丙基戊基膦酸,丙基丁基膦酸和丙基己基膦酸,丙基丁基膦酸和丁基戊基膦酸,丙基丁基膦酸和丁基己基膦酸,
丙基丁基膦酸和戊基丙基膦酸,丙基丁基膦酸和戊基丁基膦酸,丙基丁基膦酸和戊基己基膦酸,丙基丁基膦酸和己基丁基膦酸,丙基丁基膦酸和己基丙基膦酸,丙基丁基膦酸和丙基己基膦酸,丙基丁基膦酸和丁基戊基膦酸,丙基丁基膦酸和丁基己基膦酸,丙基丁基膦酸和戊基丁基膦酸,丙基丁基膦酸和戊基己基膦酸,丙基己基膦酸和丁基己基膦酸,丙基己基膦酸和戊基丁基膦酸,丙基己基膦酸和戊基己基膦酸,丁基戊基膦酸和丁基己基膦酸,丁基戊基膦酸和戊基己基膦酸,丁基戊基膦酸和己基丁基膦酸,丁基戊基膦酸和己基戊基膦酸,丁基己基膦酸和戊基己基膦酸。
此列示亦包括所有變體,例如,正-、異-、三級-等,即,例如,三級丁基異戊基膦酸和異己基正戊基膦酸及所有的其他想像得到的混合物。
此外,多組份混合物亦可發生,例如,二甲基膦酸和甲基乙基膦酸及甲基丙基膦酸、二乙基膦酸和甲基乙基膦酸和二丙基膦酸等;據此,亦可為四組份混合物及具有更
多種前述二烷膦酸之混合物。
特別佳者係二甲基膦酸和丁基乙基膦酸、二乙基膦酸和丁基乙基膦酸、二丙基膦酸和丁基乙基膦酸、二丁基膦酸和丁基乙基膦酸、二甲基膦酸和己基乙基膦酸、二乙基膦酸和己基乙基膦酸之混合物。
該混合物較佳地包含0.1至99.9重量%式(I)的二烷膦酸與99.9至0.1重量%式(II)的丁基烷基膦酸之混合物。
該混合物較佳地包含99.9至50重量%式(I)的二烷膦酸與0.1至50重量%式(II)的丁基烷基膦酸之混合物。
該混合物更佳地包含80至99.5重量%式(I)的二烷膦酸與0.5至20重量%式(II)的丁基烷基膦酸之混合物。
該混合物較佳地包含95至99.9重量%式(I)的二烷膦酸與0.1至5重量%式(II)的丁基烷基膦酸之混合物。
較佳之式(I)的二烷膦酸係二乙基膦酸,而較佳之式(II)的丁基烷基膦酸係丁基乙基膦酸。
本發明特別含括由98至99.9重量%二乙基膦酸和2至0.1重量%丁基乙基膦酸所組成之混合物。
如前述者,該混合物較佳地另包含至少一種增效劑。該增效劑較佳地為至少一種膨脹中性(expansion-neutral)物質,此意謂其尺寸不會於熱或類似應力下改變。此變化可由熱膨脹係數定出。此描述在溫度改變時,物質尺寸之變化。
該混合物較佳地包含65至1重量%如申請專利範圍第1至12項中之至少一項之至少一種式(I)的二烷膦酸與
至少一種不同之式(II)的二烷膦酸之混合物和1至35重量%增效劑。
該混合物亦較佳地包含80至95重量%如申請專利範圍第1至12項中之至少一項之至少一種式(I)的二烷膦酸與至少一種不同之式(II)的二烷膦酸之混合物和5至20重量%增效劑。
根據本發明之方法中,所用溶劑較佳地為乙酸或水,而反應溫度較佳地為80至120℃。
較佳地,本發明之至少一種式(I)的二烷膦酸與至少一種不同之式(II)的二烷膦酸之混合物藉由混入聚合物系統中的方式處理。
該混合係藉捏和、分散和/或壓出進行。
較佳地,處理本發明之至少一種式(I)的二烷膦酸與至少一種不同之式(II)的二烷膦酸之混合物藉由添加摻入聚合物系統中之方式而使用。
特別佳地,本發明之至少一種式(I)的二烷膦酸與至少一種不同之式(II)的二烷膦酸之混合物藉由反應性摻入聚合物系統中之方式而使用。此反應性摻入之特徵在於永久結合至聚合物系統的聚合物壓出物,導致本發明之至少一種式(I)的二烷膦酸與至少一種不同之式(II)的二烷膦酸之混合物無法自聚合物壓出物溶濾出。
本發明之混合物可與其他阻燃劑和其他增效劑一起使用。該其他阻燃劑包括,例如,磷化合物,如亞膦酸鹽(phosphinate)、膦酸鹽(phosphonate)、磷酸鹽、膦酸
(phosphonic acid)、亞膦酸(phosphinic acid)、磷酸、膦、膦氧化物、磷氧化物和其他者。
用於阻燃性聚合物模塑組成物和聚合物模塑物之適當的聚合物添加劑為UV吸收劑、光安定劑、潤滑劑、著色劑、抗靜電劑、成核劑、填料、增效劑、強化劑和其他者。
該聚合物系統較佳地源自於熱塑性聚合物(例如聚醯胺、聚酯或聚苯乙烯)和/或熱固性聚合物之群組。
該熱固性聚合物較佳地為環氧樹脂。
該熱固性聚合物更佳地為經下列固化的環氧樹脂:酚和/或雙氰胺[更常為:酚衍生物(松香);醇和胺],特別是酚衍生物和雙氰胺。
該熱固性聚合物更佳地為經酚和/或雙氰胺和/或觸媒所固化的環氧樹脂。
該觸媒較佳地為咪唑化合物。
該環氧樹脂較佳地為聚環氧化合物。
該環氧樹脂較佳地為以清漆和雙酚A樹脂為底的樹脂。
該聚合物較佳地為單-和二烯烴之聚合物,例如聚丙烯、聚異丁烯、聚-1-丁烯、聚-4-甲基-1-戊烯、聚異戊二烯(polyisoprene)或聚丁二烯,及環烯烴(例如環戊烯或降冰片烯(norborene))的加成聚合物;及聚乙烯(其可任意地經交聯),如高密度聚乙烯(HDPE)、高密度高分子量聚乙烯(HDPE-HMW)、高密度超高分子量聚乙烯(HDPE-
UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、直鏈低密度聚乙烯(LLDPE)、支鏈低密度聚乙烯(BLDPE)、和彼等之混合物。
該聚合物較佳地為單-和二烯烴彼此或與其他乙烯基單體之共聚物,例如乙烯-丙烯共聚物、直鏈低密度聚乙烯(LLDPE)和彼等與低密度聚乙烯(LDPE)之混合物、丙烯-1-丁烯共聚物、丙烯-異丁烯共聚物、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、異丁烯-異戊二烯共聚物、乙烯-丙烯酸烷酯共聚物、乙烯-甲基丙烯酸烷酯共聚物、乙烯-乙酸乙烯酯共聚物及彼等與一氧化碳之共聚物、或乙烯-丙烯酸共聚物和彼等的鹽(離子聚合物)、及乙烯與丙烯和二烯(如己二烯、二環戊二烯或亞乙基降冰片烯)的三聚物;及這些共聚物彼此之混合物,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或無規聚烯烴(polyalkylene)/一氧化碳共聚物和彼等與其他聚合物(例如聚醯胺)之混合物。
該聚合物較佳地為烴樹脂(如C5-C9),包括彼等之氫化的改質物(如發黏樹脂)及聚烯烴和澱粉之混合物。
該聚合物較佳地為聚苯乙烯(Polystyrol® 143E(BASF))、聚(對-甲基苯乙烯)、聚(α-甲基苯乙烯)。
該聚合物較佳地為苯乙烯或α-甲基苯乙烯與二烯或
丙烯酸系衍生物之共聚物,例如苯乙烯-丁二烯、苯乙烯-丙烯腈、苯乙烯-甲基丙烯酸烷酯、苯乙烯-丁二烯-丙烯酸烷酯和甲基丙烯酸烷酯、苯乙烯-順丁烯二酸酐、苯乙烯-丙烯腈-丙烯酸甲酯;苯乙烯共聚物和其他聚合物(例如聚丙烯酸酯、二烯聚合物或乙烯-丙烯-二烯三聚物)之更耐衝擊的混合物;及苯乙烯的嵌段共聚物,例如苯乙烯-丁二烯-苯乙烯、苯乙烯-異戊二烯-苯乙烯、苯乙烯-乙烯/丁烯-苯乙烯或苯乙烯-乙烯/丙烯-苯乙烯。
該聚合物亦較佳地為苯乙烯或α-甲基苯乙烯的接枝共聚物,例如苯乙烯與聚丁二烯的接枝共聚物、苯乙烯與聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物的接枝共聚物、苯乙烯和丙烯腈(或甲基丙烯腈)與聚丁二烯的接枝共聚物;苯乙烯、丙烯腈和甲基丙烯酸甲酯與聚丁二烯的接枝共聚物;苯乙烯和順丁烯二酸酐與聚丁二烯的接枝共聚物;苯乙烯、丙烯腈和順丁烯二酸酐或順丁二烯醯亞胺與聚丁二烯的接枝共聚物;苯乙烯和順丁二烯醯亞胺與聚丁二烯的接枝共聚物、苯乙烯和丙烯酸烷酯或甲基丙烯酸烷酯與聚丁二烯的接枝共聚物、苯乙烯和丙烯腈與乙烯-丙烯-二烯三聚物的接枝共聚物、苯乙烯和丙烯腈與聚丙烯酸烷酯或聚甲基丙烯酸烷酯的接枝共聚物、苯乙烯和丙烯腈與丙烯酸酯-丁二烯共聚物的接枝共聚物、及彼等之混合物,其被稱為,例如,ABS、MBS、ASA或AES聚合物。
該苯乙烯聚合物較佳地為相對粗孔發泡體,如EPS(膨脹的聚苯乙烯),如Styropor(BASF)和/或具相對小孔的
發泡體,如XPS(擠出的剛性聚苯乙烯發泡體),如Styrodur®(BASF)。較佳者係聚苯乙烯發泡體,例如Austrotherm® XPS、Styrofoam®(Dow Chemical)、Floormate®、Jackodur®、Lustron®、Roofmate®、Sagex®和Telgopor®。
該聚合物較佳地為經鹵化的聚合物,例如聚氯平(polychloroprene)、氯橡膠、異丁烯-異戊二烯之氯化和溴化的共聚物(鹵丁基橡膠)、氯化或氯磺酸化的聚乙烯、乙烯和氯化的乙烯之共聚物、表氯醇均-和共聚物,特別是鹵化的乙烯基化合物之聚合物,例如聚氯乙烯、聚偏二氯乙烯、聚氟乙烯、聚偏二氟乙烯;和彼等之共聚物,如氯乙烯-偏二氯乙烯、氯乙烯-乙酸乙烯酯或偏二氯乙烯-乙酸乙烯酯。
該聚合物較佳地為自α,β-不飽和酸和其衍生物所衍生的聚合物,例如聚丙烯酸酯和聚甲基丙烯酸酯、聚甲基丙烯酸甲酯、聚丙烯醯胺和衝擊性經丙烯酸丁酯改質的聚丙烯腈、及所述單體彼此或與其他不飽和單體之共聚物(例如丙烯腈-丁二烯共聚物、丙烯腈-丙烯酸烷酯共聚物、丙烯腈-丙烯酸烷氧基烷酯共聚物、丙烯腈-鹵乙烯共聚物或丙烯腈-甲基丙烯酸烷酯-丁二烯三聚物)。
該聚合物較佳地為自不飽和醇和胺或彼等的醯基衍生物或縮醛所衍生的聚合物,例如聚乙烯醇、聚乙酸乙烯酯、硬脂酸乙烯酯、苯甲酸乙烯酯或順丁烯二酸乙烯酯、聚乙烯基丁縮醛、聚酞酸烯丙酯、聚烯丙基三聚氰胺;及彼
等與烯烴之共聚物。
該聚合物較佳地為環狀醚的均-和共聚物,如聚伸烷二醇、聚環氧乙烷、聚環氧丙烷或彼等與雙環氧丙醚之共聚物。
該聚合物較佳地為聚縮醛,如聚甲醛,和含有共聚單體(例如環氧乙烷)的聚甲醛;經熱塑性聚胺甲酸酯、丙烯酸酯或MBS改質的聚縮醛。
該聚合物較佳地為聚苯醚和聚苯硫醚及彼等與苯乙烯聚合物或聚醯胺之混合物。
該聚合物較佳地為自具有兩個末端羥基的聚醚、聚酯和聚丁二烯與脂族或芳族聚異氰酸酯和彼等的前驅物所衍生的聚胺甲酸酯。
該聚合物較佳地為聚醯胺和共聚醯胺,其係衍生自二胺和二羧酸和/或衍生自胺基羧酸或對應的內醯胺,如尼龍2/12、尼龍4(聚-4-胺基丁酸、Nylon® 4,得自DuPont)、尼龍4/6(聚(己二醯丁二胺),尼龍® 4/6,得自DuPont)、尼龍6(聚己內醯胺,聚-6-胺基己酸,Nylon® 6,得自DuPont,Akulon K122,得自DSM;Zytel® 7301,得自DuPont;Durethan® B 29,得自Bayer)、尼龍6/6((聚(N,N’-己二醯己二胺),Nylon® 6/6,得自DuPont,Zytel® 101,得自DuPont;Durethan A30、Durethan® AKV、Durethan® AM,得自Bayer;Ultramid®
A3,得自BASF)、尼龍6/9(聚(壬二醯己二胺),Nylon® 6/9,得自DuPont)、尼龍6/10(聚(癸二醯己二胺)、Nylon® 6/10,得自DuPont)、尼龍6/12(聚(十二烷二醯己二胺),Nylon® 6/12,得自DuPont)、尼龍6/66(聚(癸二醯己二胺-共-己內醯胺),Nylon® 6/66,得自DuPont)、尼龍7(聚-7-胺基庚酸,Nylon® 7,得自DuPont)、尼龍7,7(聚庚二醯庚二胺,Nylon® 7,7,得自DuPont)、尼龍8(聚-8-胺基辛酸,Nylon® 8,得自DuPont)、尼龍8,8(聚辛二醯辛二胺,Nylon® 8,8,得自DuPont)、尼龍9(聚-9-胺基壬酸,Nylon® 9,得自DuPont)、尼龍9,9(聚壬二醯壬二胺,Nylon® 9,9,得自DuPont)、尼龍10(聚-10-胺基癸酸,Nylon® 10,得自DuPont)、尼龍10,9(聚癸二醯癸二胺,Nylon® 10,9,得自DuPont)、尼龍10,10(聚癸二醯癸二胺,Nylon® 10,10,得自DuPont)、
尼龍11(聚-11-胺基十一烷酸,Nylon® 11,得自DuPont)、尼龍12(聚月桂基內醯胺,Nylon® 12,得自DuPont,Grillamid® L20,得自Ems Chemie)、出於間-二甲苯、二胺和己二酸的芳族聚醯胺;製自己二胺和異-和/或對酞酸的聚醯胺(聚異酞醯己二胺、聚對酞醯己二胺)和任意地彈性體作為改質劑(如聚-2,4,4-三甲基對酞醯己二胺或聚-間-伸苯基異酞醯胺)之聚醯胺。前述聚醯胺與聚烯烴、烯烴共聚物、離子聚合物或化學鍵結的或接枝的彈性體之嵌段共聚物;或與聚醚(例如與聚乙二醇、聚丙二醇或聚丁二醇)之嵌段共聚物。此外,經EPDM(乙烯-丙烯-二烯橡膠)或ABS(丙烯腈-丁二烯-苯乙烯)改質的聚醯胺或共聚醯胺;和在加工期間內縮合的聚醯胺(“RIM聚醯胺系統”)。
該聚合物較佳地為聚脲、聚醯亞胺、聚醯胺醯亞胺、聚醚醯亞胺、聚酯醯亞胺、聚乙內醯胺和聚苯并咪唑。
該聚合物較佳地為自二羧酸和二醇和/或自羥基羧酸或對應的內酯所衍生的內酯(如聚對酞酸乙二酯、聚對酞酸丁二酯(Celanex® 2500,Celanex® 2002,得自Celanese ;Ultradur®,得自BASF)、聚-1,4-二羥甲基環己烷對酞酸酯、聚羥基苯甲酸酯),和自具有羥基末端基團的聚醚所衍生的嵌段聚醚酯;及經聚碳酸酯或MBS改質的聚酯。
該聚合物較佳地為聚碳酸酯和聚酯碳酸酯。
該聚合物較佳地為聚碸、聚醚碸和聚醚酮。較佳地,
該聚合物係交聯聚合物,其一方面衍生自醛,而另一方面衍生自酚、脲或三聚氰胺,如酚-甲醛、脲-甲醛和三聚氰胺-甲醛樹脂。
該聚合物較佳地為乾燥和非乾燥的醇酸樹脂。
該聚合物較佳地為不飽和聚酯樹脂,其衍生自飽和和不飽和二羧酸與多羥基醇的共聚酯,且乙烯基化合物作為交聯劑,亦可為彼等之經鹵化的阻燃改質物。
該聚合物較佳地為可交聯的丙烯酸系樹脂,其衍生自經取代的丙烯酸系酯類,例如衍生自環氧基丙烯酸酯、胺甲酸酯丙烯酸酯或聚酯丙烯酸酯。
較佳地,該聚合物為經三聚氰胺樹脂、脲樹脂、異氰酸酯、三聚異氰酸酯、聚異氰酸酯或環氧樹脂交聯之醇酸樹脂、聚酯樹脂和丙烯酸酯樹脂。
該聚合物較佳地為經交聯的環氧樹脂,其衍生自脂族、環脂族、雜環或芳族環氧丙基化合物,例如雙酚A二環氧丙醚、雙酚F二環氧丙醚的產物,其經慣用硬化劑(例如酐或胺)在有或無加速劑情況下交聯。
該聚合物較佳地為前述聚合物之混合物(聚摻合物),例如,PP/EPDM(聚丙烯/乙烯-丙烯-二烯橡膠)、聚醯胺/EPDM或ABS(聚醯胺/乙烯-丙烯-二烯橡膠或丙烯腈-丁二烯-苯乙烯)、PVC/EVA(聚氯乙烯/乙烯-乙酸乙烯酯)、PVC/ABS(聚氯乙烯/丙烯腈-丁二烯-苯乙烯)、PVC/MBS(聚氯乙烯/甲基丙烯酸酯-丁二烯-苯乙烯)、PC/ABS(聚碳酸酯/丙烯腈-丁二烯-苯乙烯)、PBTP/ABS(聚對酞酸丁二
酯/丙烯腈-丁二烯-苯乙烯)、PC/ASA(聚碳酸酯/丙烯酸酯-苯乙烯-丙烯腈)、PC/PBT(聚碳酸酯/聚對酞酸丁二酯)、PVC/CPE(聚氯乙烯/氯化的聚乙烯)、PVC/丙烯酸酯(聚氯乙烯/丙烯酸酯)、POM/熱塑性PUR(聚甲醛/熱塑性聚胺甲酸酯)、PC/熱塑性PUR(聚碳酸酯/熱塑性聚胺甲酸酯)、POM/丙烯酸酯(聚甲醛/丙烯酸酯)、POM/MBS(聚甲醛/甲基丙烯酸酯-丁二烯-苯乙烯)、PPO/HIPS(聚苯醚/高衝擊性聚苯乙烯)、PPO/PA 6,6(聚苯醚/尼龍6,6)和共聚物、PA/HDPE(聚醯胺/高密度聚乙烯)、PA/PP(聚醯胺/聚乙烯)、PA/PPO(聚醯胺/聚苯醚)、PBT/PC/ABS(聚對酞酸丁二酯/聚碳酸酯/丙烯腈-丁二烯-苯乙烯)和/或PBT/PET/PC(聚對酞酸丁二酯/聚對酞酸乙二酯/聚碳酸酯)。
所製得的模塑物較佳地為具有規則或不規則底的長方形、或立方形、似立方形、墊形或稜柱形。
藉以下實例說明本發明。
阻燃性聚合物模塑組成物及阻燃性聚合物模塑物之製造、加工和測試
阻燃劑組份與聚合物粒和任何添加劑混合並在雙螺桿壓出機(型號:Leistritz LSM® 30/34)中於溫度230至260℃(PBT-GR)或260至280℃(PA 66-GR)摻合。排放均質化的聚合物條,在水浴中冷卻並於之後粒化。
充分乾燥之後,模塑組成物在射出模塑機(型號:
Aarburg Allrounder)上於溫度為240至270℃(PBT-GR)或260至290℃(PA 66-GR)加工以得到試樣。使用UL 94試驗(Underwriter Laboratories)測試試樣的阻燃性並分級。
各混合物的試樣以1.5毫米厚度的試樣進行UL 94燃燒分級(Underwriter Laboratories)。UL 94燃燒分級如下:
V-0:火燄施用終了之後,續燃時間(afterflame time)不曾超過10秒,10次施燄的總續燃時間不超過50秒,沒有火燄掉落,試樣未完全耗盡,試樣的餘燼時間(afterglow time)不曾超過30秒。
V-1:火燄施用終了之後,續燃時間不曾超過30秒,10次施燄的總續燃時間不超過250秒,火燄施用終了之後,試樣的餘燼時間不曾超過60秒,其他標準如同V-0。
V-2:棉指示劑被掉落的火燄點燃,其他標準如同V-1無法分級(ncl):無法符合V-2等級。
用於檢驗的一些樣品亦測定其LOI。LOI(限氧指數)係根據ISO 4589測定。根據ISO 4589,LOI對應於聚合物在氧和氮之混合物中仍維持燃燒的最低氧濃度(以體積%表示)。LOI越高,則所測試材料的不可燃性越高。
LOI 23 可燃
LOI 24-28 可燃性有限
LOI 29-35 阻燃
LOI>36 特別阻燃
所用化學品和縮寫:
酚清漆:Bakelite® PF 0790,得自Hexion
引發劑:Vazo 67,得自DuPont
根據EP-A-1544205的實例8,利用引發劑和乙烯,自次磷酸鈉得到二乙基膦酸金屬鹽溶液。此產物溶液以稀硫酸進行後續處理,濃縮,過濾及於184℃(1毫巴)蒸餾得到產率94%之二乙基膦酸(99.9重量%)和丁基乙基膦酸(0.01重量%)之混合物。
根據EP-A-1544205的實例8,利用引發劑和乙烯,自次磷酸鈉得到二乙基膦酸金屬鹽溶液。此產物溶液以稀硫酸進行後續處理,濃縮,過濾及於180-190℃(1毫巴)蒸餾得到產率92%之二乙基膦酸(98重量%)和丁基乙基膦酸(2重量%)之混合物。
以類似於EP-A-1544205的實例8的方式,利用引發劑和乙烯,自次磷酸鈉得到二乙基膦酸,其藉後續蒸餾而純化。
類似於WO-A-2009-010188,藉乙基膦酸與丁烯之反應合成丁基乙基膦酸。
藉由混合此二種純淨組份,得到重量比為90:10的
二乙基膦酸和丁基乙基膦酸之混合物。
以對應於實例3的方式,藉由混合兩種純淨組份,得到重量比為60:40的二乙基膦酸和丁基乙基膦酸之混合物。
以對應於實例3的方式,藉由混合兩種純淨組份,得到重量比為50:50的二乙基膦酸和丁基乙基膦酸之混合物。
初時將1000克環氧樹脂(如Beckopox EP 140)引至2升五頸瓶設備中。加熱至110℃ 1小時,並於減低壓力下移除揮發性組份。之後,反應混合物以氮加以惰性化並將瓶中的溫度提高至170℃。各情況中,添加118克磷化合物之混合物(選自實例1至5),同時在流動的氮下攪拌,觀察到放熱反應。所得樹脂為黃色並可自由流動。
100份經磷改質的環氧樹脂與1對應OH當量的酚清漆(氫氧化物當量105克/莫耳,熔點85-95℃)混合並加熱
至150℃。攪拌此混合物直到形成均勻混合物並使其冷卻至130℃。之後,添加0.03份2-苯基咪唑且再度攪拌此混合物5-10分鐘。之後,混合物於溫熱時倒入碟中並於140℃固化2小時及於200℃固化2小時。
100份的b)之經磷改質的環氧樹脂加至63份丙酮和27份Dowanol®PM中,並添加適當量的酚樹脂。此混合物攪拌30分鐘,之後添加2-苯基咪唑。之後,混合物濾經400微米篩網以移除過量的樹脂粒。之後,將梭織玻璃織物(7628型,203克/平方米)浸入該溶液中,直到織物完全潤濕。自該混合物拉出經潤濕的織物並移除過量的樹脂。之後,經潤濕的織物分階段地先在乾燥箱中於溫度高至165℃進行短時間初步固化,及之後在受熱的加壓機中完全固化。經固化的積層物的樹脂含量為30-50%。
根據ASTM E831-06測定製得之模塑物(積層物)之熱膨脹。
根據製造聚合物模塑物之一般方法,使用100重量%雙酚A樹脂以製造積層物。
以類似於專利案EP-A-1544205實例8的方式,利用
引發劑和乙烯,自次磷酸鈉得到二乙基膦酸,接著蒸餾以純化。
根據製造聚合物模塑物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A和10重量%二乙基膦酸所構成之組成物製造模塑物。
類似於WO-A-2009/010188,利用乙基膦酸與丁烯之反應,合成丁基乙基膦酸。
根據製造聚合物模塑物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A和10重量%丁基乙基膦酸所構成之組成物製造模塑物。
根據製造聚合物模塑物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A和10重量%根據實例1之本發明混合物所構成之組成物製造模塑物。
根據製造聚合物模塑物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A和10重量%根據實例2之本發明混合物所構成之組成物製造模塑物。
根據製造聚合物模塑物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A和10重量%根據實例3之本發明混合物所構成之組成物製造模塑物。
根據製造聚合物模塑物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A和10重量%根據實例4之本發明混合物所構成之組成物製造模塑物。
根據製造聚合物模塑物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A和10重量%根據實例5之本發明混合物所構成之組成物製造模塑物。
所得結果示於以下的表中:
相較於純積層物(實例6),包含本發明之二乙基膦酸和丁基乙基膦酸之混合物的積層物之熱膨脹係數值降低;熱膨脹因此極低。丁基乙基膦酸含量提高可獲進一步改良。本發明之產物使得所製得的模塑物的膨脹較低並因此而符合尺寸安定性的要求。
Claims (23)
- 一種至少一種式(I)的二烷膦酸(dialkylphosphinic acid)與至少一種不同之式(II)的二烷膦酸之混合物
- 如申請專利範圍第1項之混合物,其中R1和R2相同或不同且各自為甲基、乙基、正丙基、異丙基、正丁基、異丁基、三級丁基、正戊基、異戊基、正己基、異己基和/或苯基。
- 如申請專利範圍第1或2項之混合物,其中R3和R4相同或不同且各自為甲基、乙基、正丙基、異丙基、 正丁基、異丁基、三級丁基、正戊基、異戊基、正己基、異己基和/或苯基,先決條件是R3和R4基團中之至少一者不同於R1和R2。
- 如申請專利範圍第1項之混合物,其包含0.1至99.9重量%式(I)的二烷膦酸和99.9至0.1重量%不同之式(II)的二烷膦酸。
- 如申請專利範圍第1項之混合物,其包含40至99.9重量%式(I)的二烷膦酸和60至0.1重量%不同之式(II)的二烷膦酸。
- 如申請專利範圍第1項之混合物,其包含60至99.9重量%式(I)的二烷膦酸和40至0.1重量%不同之式(II)的二烷膦酸。
- 如申請專利範圍第1項之混合物,其包含80至99.9重量%式(I)的二烷膦酸和20至0.1重量%不同之式(II)的二烷膦酸。
- 如申請專利範圍第1項之混合物,其包含90至99.9重量%式(I)的二烷膦酸和10至0.1重量%不同之式(II)的二烷膦酸。
- 如申請專利範圍第1項之混合物,其包含95至99.9重量%式(I)的二烷膦酸和5至0.1重量%不同之式(II)的二烷膦酸。
- 如申請專利範圍第1項之混合物,其包含98至99.9重量%式(I)的二烷膦酸和2至0.1重量%不同之式(II)的二烷膦酸。
- 如申請專利範圍第1項之混合物,其中該二烷膦酸係二乙基膦酸、乙基丙基膦酸、乙基丁基膦酸、乙基戊基膦酸、乙基己基膦酸、二丙基膦酸、丙基丁基膦酸、丙基戊基膦酸、丙基己基膦酸、二丁基膦酸、丁基戊基膦酸、丁基己基膦酸、二戊基膦酸、戊基己基膦酸和/或二己基膦酸。
- 如申請專利範圍第1項之混合物,其包含98至99.9重量%的二乙基膦酸和2至0.1重量%的丁基乙基膦酸。
- 如申請專利範圍第1項之混合物,其另包含至少一種增效劑,而該增效劑為含氮化合物,例如蜜勒胺(melem)、蜜白胺(melam)、三聚二氰亞胺(melon)、三聚氰胺(melamine)硼酸鹽、三聚氰胺三聚氰酸鹽、三聚氰胺磷酸鹽、二(三聚氰胺)磷酸鹽、五(三聚氰胺)三磷酸鹽、三(三聚氰胺)二磷酸鹽、肆(三聚氰胺)三磷酸鹽、陸(三聚氰胺)五磷酸鹽、三聚氰胺二磷酸鹽、三聚氰胺四磷酸鹽、三聚氰胺焦磷酸鹽、三聚氰胺聚磷酸鹽、蜜白胺聚磷酸鹽、蜜勒胺聚磷酸鹽和/或三聚二氰亞胺聚磷酸鹽;鋁化合物,如氫氧化鋁、多水高嶺土(halloysite)、藍寶石產物、水鋁土(boehmite)、奈水鋁土(nanoboehmite);鎂化合物,如氫氧化鎂;錫化合物,如氧化錫;銻化合物,如氧化銻; 鋅化合物,如氧化鋅、氫氧化鋅、氧化鋅水合物、碳酸鋅、錫酸鋅、羥基錫酸鋅、矽酸鋅、磷酸鋅、硼磷酸鋅、硼酸鋅和/或鉬酸鋅;矽化合物,如矽酸鹽和/或聚矽氧;磷化合物,如亞膦酸(phosphinic acid)和彼等的鹽、膦酸(phosphonic acid)和彼等的鹽和/或膦氧化物、膦氮烯(phosphazene)和/或哌(焦)磷酸鹽;碳化二醯亞胺、哌、(聚)異氰酸酯、苯乙烯-丙烯酸系聚合物;和/或羰基雙己內醯胺;得自參(羥乙基)三聚異氰酸酯與芳族多羧酸的低聚酯之氮化合物、或6-苯基胍胺(benzoguguanamine)、6-甲基胍胺(acetoguanamine)、參(羥乙基)三聚異氰酸酯、乙內醯脲(allantoin)、甘脲(glycoluril)、三聚氰酸酯、三聚氰酸酯-環氧化物化合物、脲三聚氰酸酯、二氰醯胺、胍、胍磷酸鹽和/或硫酸鹽。
- 如申請專利範圍第1項之混合物,其包含99至1重量%如申請專利範圍第1至12項中至少一項之至少一種式(I)的二烷膦酸和至少一種不同之式(II)的二烷膦酸之混合物及1至99重量%增效劑。
- 一種製造如申請專利範圍第1至12項中任一項之混合物的方法,其包含令磷來源與引發劑和烯烴反應及以無機酸處理所得之經烷化的磷化合物,並藉由濃縮和處理而令其轉化成至少一種式(I)的二烷膦酸和至少一種不同之式(II)的二烷膦酸之混合物。
- 如申請專利範圍第15項之方法,其中該磷來源係亞膦酸鹽,該烯烴係乙烯,該無機酸係硫酸或氫氯酸,而該自由基引發劑係2,2’-偶氮基雙(2-脒基丙烷)二氫氯酸鹽、2,2’-偶氮基雙(N,N’-二伸甲基異丁脒)二氫氯酸鹽、偶氮基雙(異丁腈)、4,4’-偶氮基雙(4-氰基戊酸)和/或2,2’-偶氮基雙(2-甲基丁腈)或過氧化氫、過氧基二硫酸銨、過氧基二硫酸鉀、二苄醯過氧化物、二-三級丁基過氧化物、過乙酸、二異丁基過氧化物、過氧基新癸酸異丙苯酯、過氧基新癸酸三級丁酯、過氧基三級戊酸三級丁酯、過氧基三級戊酸三級戊酯、過氧基二碳酸二丙酯、過氧基二碳酸二丁酯、過氧基二碳酸二肉豆蔻酯、二月桂醯過氧化物、過氧基-2-乙基己酸1,1,3,3-四甲基丁酯、過氧基-2-乙基己基碳酸三級戊酯、過氧基異丁酸三級戊酯、1,1-二(三級丁基過氧基)環己烷、過氧基苯甲酸三級丁酯、過氧基乙酸三級丁酯、過氧基二乙基乙酸三級丁酯、過氧基異丙基碳酸三級丁酯、2,2-二(三級丁基過氧基)丁烷、三級戊基氫過氧化物和/或2,5-二甲基-2,5-二(三級丁基過氧基)己烷。
- 如申請專利範圍第15或16項之方法,其中亞膦酸鈉與乙烯反應之後與稀硫酸反應,濃縮,過濾和蒸餾,以得到二乙基膦酸與丁基乙基膦酸之混合物。
- 如申請專利範圍第15項之方法,其中該反應發生於溶劑中,且該溶劑係醇、酸或水。
- 如申請專利範圍第15項之方法,其中該反應溫 度介於50和150℃之間。
- 如申請專利範圍第1至12項中任一項之混合物之用途,其係作為用於進一步合成的中間產物,作為黏合劑,在環氧樹脂、聚胺甲酸酯和不飽和的聚酯樹脂之固化中作為交聯劑和/或加速劑,作為聚合物安定劑,作為作物保護組成物,作為螯合劑,作為礦油添加劑,作為抗腐蝕劑,用於清洗和清潔組成物應用及用於電子應用。
- 如申請專利範圍第1至14項中任一項之混合物之用途,其係作為阻燃劑,特別是作為透明塗層和泡脹塗層的阻燃劑,作為木材和其他纖維素產品的阻燃劑,作為聚合物的反應性和/或非反應性阻燃劑,用以製造阻燃性聚合物模塑組成物,用以製造阻燃性聚合物模塑物和/或用以藉由浸滲而賦予聚酯及純和摻合的纖維素織品阻燃性,及作為增效劑。
- 一種阻燃性熱塑性或熱固性聚合物模塑組成物或聚合物模塑物、膜、纖絲或纖維,其包含0.5至45重量%如申請專利範圍第1至14項中任一項之混合物、0.5至99.5重量%熱塑性或熱固性聚合物或彼等之混合物、0至55重量%添加劑和0至55重量%填料或強化材料,其中組份的總和為100重量%。
- 一種阻燃性熱塑性或熱固性聚合物模塑組成物或聚合物模塑物、膜、纖絲或纖維,其包含1至30重量%如申請專利範圍第1至14項中任一項之混合物、10至95重量%熱塑性或熱固性聚合物或彼等之混合物、2至30重 量%添加劑和2至30重量%填料或強化材料,其中組份的總和為100重量%。
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-
2011
- 2011-12-21 DE DE102011121900A patent/DE102011121900A1/de not_active Withdrawn
-
2012
- 2012-11-14 TW TW101142473A patent/TWI579294B/zh active
- 2012-12-13 JP JP2014547751A patent/JP6391094B2/ja active Active
- 2012-12-13 KR KR1020147020356A patent/KR102057435B1/ko active IP Right Grant
- 2012-12-13 US US14/364,972 patent/US20140350149A1/en not_active Abandoned
- 2012-12-13 CN CN201280063181.1A patent/CN104093728A/zh active Pending
- 2012-12-13 PL PL12805591T patent/PL2794623T3/pl unknown
- 2012-12-13 WO PCT/EP2012/005175 patent/WO2013091805A1/de active Application Filing
- 2012-12-13 EP EP12805591.0A patent/EP2794623B1/de active Active
- 2012-12-13 ES ES12805591.0T patent/ES2650627T3/es active Active
-
2017
- 2017-09-22 US US15/713,547 patent/US10246640B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
TWI579294B (zh) | 2017-04-21 |
EP2794623B1 (de) | 2017-10-18 |
DE102011121900A1 (de) | 2013-06-27 |
WO2013091805A1 (de) | 2013-06-27 |
EP2794623A1 (de) | 2014-10-29 |
US20140350149A1 (en) | 2014-11-27 |
KR102057435B1 (ko) | 2019-12-20 |
PL2794623T3 (pl) | 2018-03-30 |
US10246640B2 (en) | 2019-04-02 |
JP2015507658A (ja) | 2015-03-12 |
CN104093728A (zh) | 2014-10-08 |
US20180010047A1 (en) | 2018-01-11 |
KR20140112526A (ko) | 2014-09-23 |
JP6391094B2 (ja) | 2018-09-19 |
ES2650627T3 (es) | 2018-01-19 |
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