TWI614263B - 二膦酸與二烷膦酸之混合物,彼之製法與應用 - Google Patents
二膦酸與二烷膦酸之混合物,彼之製法與應用 Download PDFInfo
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- TWI614263B TWI614263B TW101142471A TW101142471A TWI614263B TW I614263 B TWI614263 B TW I614263B TW 101142471 A TW101142471 A TW 101142471A TW 101142471 A TW101142471 A TW 101142471A TW I614263 B TWI614263 B TW I614263B
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- 239000000203 mixture Substances 0.000 title claims abstract description 111
- 239000002253 acid Substances 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims description 10
- 150000007513 acids Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title abstract description 4
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 229920000642 polymer Polymers 0.000 claims description 87
- -1 nitrogen-containing compound Chemical class 0.000 claims description 52
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 claims description 41
- MJUJXFBTEFXVKU-UHFFFAOYSA-N diethyl phosphonate Chemical compound CCOP(=O)OCC MJUJXFBTEFXVKU-UHFFFAOYSA-N 0.000 claims description 36
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 28
- 239000003063 flame retardant Substances 0.000 claims description 28
- 238000000465 moulding Methods 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 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 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 14
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- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- 229920001187 thermosetting polymer Polymers 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
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- 239000000654 additive Substances 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 229920001169 thermoplastic Polymers 0.000 claims description 10
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
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- 229920000388 Polyphosphate Polymers 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
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- 239000001205 polyphosphate Substances 0.000 claims description 7
- 235000011176 polyphosphates Nutrition 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
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- 239000000835 fiber Substances 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
- 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 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001345 alkine derivatives 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
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 4
- GOQJMMHTSOQIEI-UHFFFAOYSA-N hex-5-yn-1-ol Chemical compound OCCCCC#C GOQJMMHTSOQIEI-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 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
- 150000003254 radicals Chemical group 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
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 150000001622 bismuth compounds Chemical class 0.000 claims description 3
- OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 229940070710 valerate Drugs 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical group CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 claims description 2
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 claims description 2
- VPLXJIGDEIRJLV-UHFFFAOYSA-N 12,12-dimethyltridec-1-yne Chemical group CC(CCCCCCCCCC#C)(C)C VPLXJIGDEIRJLV-UHFFFAOYSA-N 0.000 claims description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical group CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 claims description 2
- CCTFAOUOYLVUFG-UHFFFAOYSA-N 2-(1-amino-1-imino-2-methylpropan-2-yl)azo-2-methylpropanimidamide Chemical group NC(=N)C(C)(C)N=NC(C)(C)C(N)=N CCTFAOUOYLVUFG-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
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 235000015510 Cucumis melo subsp melo Nutrition 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
- MYQLDSGQAKVDPQ-UHFFFAOYSA-N OP(O)(=O)OP(=O)(O)OP(=O)(O)O.N1=C(N)N=C(N)N=C1N.N1=C(N)N=C(N)N=C1N Chemical compound OP(O)(=O)OP(=O)(O)OP(=O)(O)O.N1=C(N)N=C(N)N=C1N.N1=C(N)N=C(N)N=C1N MYQLDSGQAKVDPQ-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims description 2
- 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 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
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 229960000458 allantoin Drugs 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- 235000019395 ammonium persulphate Nutrition 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 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
- NEEDEQSZOUAJMU-UHFFFAOYSA-N but-2-yn-1-ol Chemical compound CC#CCO NEEDEQSZOUAJMU-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
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 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
- 239000001177 diphosphate Substances 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052621 halloysite Inorganic materials 0.000 claims description 2
- MELUCTCJOARQQG-UHFFFAOYSA-N hex-2-yne Chemical compound CCCC#CC MELUCTCJOARQQG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 2
- 238000005470 impregnation Methods 0.000 claims description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002681 magnesium compounds Chemical class 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical group NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 claims description 2
- SYWIXHZXHQDFOO-UHFFFAOYSA-N methyl n-phenyliminocarbamate Chemical compound COC(=O)N=NC1=CC=CC=C1 SYWIXHZXHQDFOO-UHFFFAOYSA-N 0.000 claims description 2
- 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
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 2
- VUGRNZHKYVHZSN-UHFFFAOYSA-N oct-1-yn-3-ol Chemical compound CCCCCC(O)C#C VUGRNZHKYVHZSN-UHFFFAOYSA-N 0.000 claims description 2
- UMIPWJGWASORKV-UHFFFAOYSA-N oct-1-yne Chemical compound CCCCCCC#C UMIPWJGWASORKV-UHFFFAOYSA-N 0.000 claims description 2
- GZTNBKQTTZSQNS-UHFFFAOYSA-N oct-4-yne Chemical compound CCCC#CCCC GZTNBKQTTZSQNS-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- ZKGFCAMLARKROZ-UHFFFAOYSA-N oxozinc;hydrate Chemical compound O.[Zn]=O ZKGFCAMLARKROZ-UHFFFAOYSA-N 0.000 claims description 2
- GVSZYZPUKJBOJQ-UHFFFAOYSA-N pentyl 2-methylpropaneperoxoate Chemical group CCCCCOOC(=O)C(C)C GVSZYZPUKJBOJQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
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- 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 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- UXDZLUCNRYCZCG-UHFFFAOYSA-L zinc;phthalate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O UXDZLUCNRYCZCG-UHFFFAOYSA-L 0.000 description 1
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Abstract
本發明係關於一種至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸之混合物
其中R1,R2 相同或不同且各自獨立地為H、C1-C18-烷基、C2-C18-烯基、C6-C18-芳基、C7-C18-烷芳基,R5 是C1-C18-伸烷基、C2-C18-伸烯基、C6-C18-伸芳基、C7-C18-烷基伸芳基
其中R3,R4 相同或不同且各自獨立地為C1-C18-烷基、C2-C18-烯基、C6-C18-芳基和/或C7-C18-烷芳基。
本發明亦係關於這些混合物之製法和彼等之用途。
Description
本發明係關於至少一種二膦酸與至少一種二烷膦酸之混合物,彼之製法與應用。
在各種裝置(例如,電腦、相機、行動電話、LCD和TFT螢幕及其他電子裝置)中逐漸提高使用度的印刷電路板之製造時,尋求使用不同材料,特別是聚合物。這些特別包括熱固物、玻璃纖維強化的熱固物和熱塑物。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具有阻燃性。
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未受損或變形。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。
特別是,即使在預浸物(“預浸滲的纖維”的簡稱)和積層物的情況中熱膨脹顯著,因為這些預浸物和積層物構成印刷電路板的初步形式或先質。
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(例如經加工的印刷電路板)。
本發明的目的係對用於預浸物、印刷電路板和積層物的聚合物予以修飾,使得它們的熱膨脹僅極低(若有的話)並滿足尺寸安定性。
藉一種由至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸所成混合物達到此目的
其中R1,R2 相同或不同且各自獨立地為H、C1-C18-烷基、C2-C18-烯基、C6-C18-芳基、C7-C18-烷芳基,R5 是C1-C18-伸烷基、C2-C18-伸烯基、C6-C18-伸芳基、C7-C18-烷基伸芳基
其中R3,R4 相同或不同且各自獨立地為C1-C18-烷基、C2-C18-烯基、C6-C18-芳基和/或C7-C18-烷芳
基。
較佳地,R1、R2相同或不同且各自為H、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;R3、R4相同或不同且與R1和R2無關地各自為甲基、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,而R5為伸乙基、伸丁基、伸己基或伸辛基。
更佳地,R1、R2、R3和R4相同或不同且各自為乙基和/或丁基,而R5係伸乙基或伸丁基。
該混合物較佳地包含0.1至99.9重量%式(I)的二膦酸和99.9至0.1重量%式(II)的二烷膦酸。
該混合物較佳地亦包含60至99.9重量%式(I)的二膦酸和40至0.1重量%式(II)的二烷膦酸。
較佳混合物包含80至99.9重量%式(I)的二膦酸和20至0.1重量%式(II)的二烷膦酸。
特別佳的混合物包含90至99.9重量%式(I)的二膦酸和10至0.1重量%式(II)的二烷膦酸。
特別佳的混合物包含95至99.9重量%式(I)的二膦酸和5至0.1重量%式(II)的二烷膦酸。
極佳的混合物包含98至99.9重量%式(I)的二膦酸和2至0.1重量%式(II)的二烷膦酸。
較佳地,該二膦酸係伸乙基-1,2-雙(乙膦酸)、伸乙基-1,2-雙(丙膦
酸)、伸乙基-1,2-雙(丁膦酸)、伸乙基-1,2-雙(戊膦酸)、伸乙基-1,2-雙(己膦酸)、丁烷-1,2-雙(乙膦酸)、丁烷-1,2-雙(丙膦酸)、丁烷-1,2-雙(丁膦酸)、丁烷-1,2-雙(戊膦酸)、丁烷-1,2-雙(己膦酸)、己烷-1,2-雙(乙膦酸)、己烷-1,2-雙(丙膦酸)、己烷-1,2-雙(丁膦酸)、己烷-1,2-雙(戊膦酸)或己烷-1,2-雙(己膦酸),而該二烷膦酸係二乙膦酸、二丙膦酸、二丁膦酸、二戊膦酸或二己膦酸。
該較佳混合物包含98至99.9重量%的伸乙基-1,2-雙(乙膦酸)和2至0.1重量%的二乙膦酸。
該混合物較佳地另包含至少一種增效劑。
該增效劑較佳地為含氮的化合物,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,如膦酸和彼等的鹽、膦酸和彼等的鹽和/或膦氧化物、膦氮烯(phosphazene)和/或哌(焦)磷酸鹽;碳二亞胺、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)三聚異氰酸鹽與芳族多羧酸的低聚酯之氮化合物、或苯并胍胺、乙醯胍胺、參(羥乙基)三聚異氰酸酯、乙內醯脲(allantoin)、甘脲(glycoluril)、三聚氰酸鹽、三聚氰酸鹽-環氧化物化合物、脲三聚氰酸脲、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11項中之至少一項之至少一種式(I)的二膦酸和至少一種式(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11
項中之至少一項之混合物之方法,其包含令膦酸來源與炔在引發劑存在下反應。
較佳地,該膦酸來源是乙膦酸而該炔是乙炔、甲基乙炔、1-丁炔、1-己炔、2-己炔、1-辛炔、4-辛炔、1-丁炔-4-醇、2-丁炔-1-醇、3-丁炔-1-醇、5-己炔-1-醇、1-辛炔-3-醇、1-戊炔、苯基乙炔、三甲基矽基乙炔和/或二苯基乙炔,而該引發劑係具有氮-氮或氧-氧鍵的自由基引發劑,且該反應溫度介於50和150℃之間。
該自由基引發劑係2,2’-偶氮基雙(2-脒基丙烷)二氯化氫、2,2’-偶氮基雙(N,N’-二伸甲基異丁脒)二氯化氫、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、三級戊基過氧化氫和/或2,5-二甲基-2,5-二(三級丁基過氧基)己烷。
該溶劑較佳地包含直鏈或支鏈烷、經烷基取代的芳族溶劑、與水不互溶或僅部分與水互溶的醇或醚、水和/或乙酸。
該醇較佳地係甲醇、丙醇、異丁醇、和/或正丁醇、或包含這些醇與水之混合物。
本發明亦係關於一種如申請專利範圍第1至11項中之至少一項之至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸之混合物之用途,其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。
本發明另係關於一種如申請專利範圍第1至13項中之至少一項之至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸之混合物之用途,其作為阻燃劑,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製組成物,用以製造阻燃性聚合物模製物和/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製組成物及聚合物模製物、膜、纖絲和纖維,其包含0.5至45重量%如申請專利範圍第1至13項中之至少一項之
混合物、55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,其中組份的和為100重量%。
本發明最後係關於一種阻燃性熱塑性或熱固性聚合物模製組成物及聚合物模製物、膜、纖絲和纖維,其包含2至30重量%如申請專利範圍第1至13項中之至少一項之混合物、60至94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,其中組份的和為100重量%。
式(I)的二膦酸與式(II)的二烷膦酸之較佳混合物係,例如:伸乙基-1,2-雙(乙膦酸)和二乙膦酸,伸乙基-1,2-雙(乙膦酸)和丁基乙基膦酸,伸乙基-1,2-雙(乙膦酸)和丁基丁基膦酸,伸乙基-1,2-雙(乙膦酸)和己基乙基膦酸,伸乙基-1,2-雙(乙膦酸)和辛基乙基膦酸,伸乙基-1,2-雙(乙膦酸)和己基丁基膦酸,伸乙基-1,2-雙(丁膦酸)和二乙膦酸,伸乙基-1,2-雙(丁膦酸)和丁基乙基膦酸,伸乙基-1,2-雙(丁膦酸)和丁基丁基膦酸,伸乙基-1,2-雙(丁膦酸)和己基乙基膦酸,伸乙基-1,2-雙(丁膦酸)和辛基乙基膦酸,
伸乙基-1,2-雙(丁膦酸)和己基丁基膦酸,伸丁基-1,2-雙(乙膦酸)和二乙膦酸,伸丁基-1,2-雙(乙膦酸)和丁基乙基膦酸,伸丁基-1,2-雙(乙膦酸)和丁基丁基膦酸,伸丁基-1,2-雙(乙膦酸)和己基乙基膦酸,伸丁基-1,2-雙(乙膦酸)和辛基乙基膦酸,伸丁基-1,2-雙(乙膦酸)和己基丁基膦酸,伸丁基-1,2-雙(丁膦酸)和二乙膦酸,伸丁基-1,2-雙(丁膦酸)和丁基乙基膦酸,伸丁基-1,2-雙(丁膦酸)和丁基丁基膦酸,伸丁基-1,2-雙(丁膦酸)和己基乙基膦酸,伸丁基-1,2-雙(丁膦酸)和辛基乙基膦酸,伸丁基-1,2-雙(丁膦酸)和己基丁基膦酸。
前述化合物亦可為多組份混合物形式。較佳的三組份混合物為,例如,伸乙基-1,2-雙(乙膦酸)和二乙膦酸和丁基乙基膦酸、伸乙基-1,2-雙(乙膦酸)和丁基乙基膦酸和丁基丁基膦酸、伸丁基-1,2-雙(乙膦酸)和二乙膦酸和丁基乙基膦酸、伸乙基-1,2-雙(乙膦酸)和伸丁基-1,2-雙(乙膦酸)和二乙膦酸等。
較佳的4組份混合物係,例如,伸乙基-1,2-雙(乙膦酸)和伸丁基-1,2-雙(乙膦酸)和二乙膦酸和丁基乙基膦酸等。
亦較佳者係由98至99.9重量%伸乙基-1,2-雙(乙膦酸)和2至0.1重量%二乙膦酸所組成之混合物。
該增效劑較佳地為至少一種膨脹中和物質。膨脹中和物質防止聚合物膨脹或將膨脹降至極低值。
具有一或多種增效劑的較佳混合物係包含99至50重量%如申請專利範圍第1至11項中之至少一項之混合物和1至50重量%增效劑者。
較佳地,本發明之至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸之混合物混入聚合物系統中而處理。
該混合藉捏和、分散和/或壓出進行。
特別佳之處理本發明之至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸之混合物的方式係藉反應性摻入聚合物系統中。此反應性摻入之特徵在於所得至聚合物系統的聚合物壓出物之永久結合,因此本發明之至少一種至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸之混合物無法自聚合物瀝濾出來。
較佳地,亦藉由添加摻入聚合物系統中的方式,使用本發明之至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸之混合物。
本發明之至少一種式(I)的二膦酸與至少一種式(II)的二烷膦酸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,如二烷膦酸鹽(phosphinate)、烷膦酸鹽(phosphonate)、磷酸鹽、烷膦酸(phosphonic acid)、二烷膦酸(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製組成物和聚合物模製物之適當聚合物添加劑為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,如聚醯胺、聚酯或聚苯乙烯和/或熱固性聚合物。
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,固化的環氧樹脂。
該熱固性聚合物更佳地為經酚和/或雙氰胺和/或觸媒固化的環氧樹脂。
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。
該環氧樹脂較佳地源自於清漆和雙酚A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、聚丁烯-1、聚-4-甲基戊烯-1、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-丁烯-1共聚物、丙烯-異丁烯共聚物、乙烯-丁烯-1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;及此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,例如苯乙烯於聚丁二烯上、苯乙烯於聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物上、苯乙烯和丙烯腈(或甲基丙烯腈)於聚丁二烯上;苯乙烯、丙烯腈和甲基丙烯酸甲酯於聚丁二烯上;苯乙烯和順丁烯二酸酐於聚丁二烯上;苯乙烯、丙烯腈和順丁烯二酸酐或順丁二烯醯亞胺於聚丁二烯上;苯乙烯和順丁二烯醯亞胺於聚丁二烯上、苯乙烯和丙烯酸烷酯或甲基丙烯酸烷酯於聚丁二烯上、苯乙烯和丙烯腈於乙烯-丙烯-二烯三聚物上、苯乙烯和丙烯腈於聚丙烯酸烷酯或聚甲基丙烯酸烷酯上、苯乙烯和丙烯腈於丙烯酸酯-丁二烯共聚物上、及彼等之混合物,其被稱為,例如,ABS、MBS、ASA或AES聚合物。
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、表氯醇均聚物和共聚物,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、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-不飽和酸和彼等之衍生物衍生者,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衍生者或彼等的醯基衍生物或縮醛,如聚乙烯醇、聚乙酸乙烯酯、硬脂酸酯、苯甲酸酯或順丁烯二酸酯、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、聚酯和聚丁二烯及脂族或芳族聚異氰酸酯和彼等的先質衍生的聚胺甲酸酯。
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(伸丁基己二醯二胺),Nylon® 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’-伸己基己二醯胺),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(伸己基壬醯胺),Nylon® 6/9,得自DuPont)、尼龍6/10(聚(伸己基癸二醯胺)、Nylon® 6/10,得自DuPont)、尼龍6/12(聚(伸己基十二烷二醯胺),Nylon® 6/12,得自DuPont)、尼龍6/66(聚(伸己基癸二醯胺-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(聚伸庚基庚二醯胺,Nylon® 7,7,得自DuPont)、
尼龍8(聚-8-胺基辛酸,Nylon® 8,得自DuPont)、尼龍8,8(聚伸辛基辛二醯胺,Nylon® 8,8,得自DuPont)、尼龍9(聚-9-胺基壬酸,Nylon® 9,得自DuPont)、尼龍9,9(聚伸壬基壬二醯胺,Nylon® 9,9,得自DuPont)、尼龍10(聚-10-胺基癸酸,Nylon® 10,得自DuPont)、尼龍10,9(聚伸癸基癸二醯胺,Nylon® 10,9,得自DuPont)、尼龍10,10(聚伸癸基癸二醯胺,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;製自己二胺和異酞酸和/或對酞酸的聚醯胺(聚伸己基異酞醯胺、聚伸己基對酞醯胺)和任意地彈性體作為改質劑(如聚-2,4,4-三甲基伸己基對酞醯胺或聚-間-伸苯基異酞醯胺)之聚醯胺。前述聚醯胺與聚烯烴之嵌段共聚物、烯烴共聚物、離聚物或化學鍵結的或接枝的彈性體;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、聚尿囊素和聚苯并咪唑。
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衍生的聚酯,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,亦為彼等之經鹵化的阻燃改質物。
該聚合物較佳地包含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,該聚合物為醇酸樹脂、聚酯樹脂和丙烯酸酯樹脂,彼等經三聚氰胺樹脂、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。
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、雜環狀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)有或無加速劑地交聯。
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)。該聚合物可以為可雷射標記。
所製得的模製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。
藉以下的實例說明本發明。
阻燃性聚合物模製組成物及阻燃性聚合物模製物之製造、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,模製組成物在射出模製機(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。
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
基本上,根據本發明之方法的實施方式係使得反應混合物於指定的反應條件下暴於相對高的乙炔流率(至少12升/小時,較佳地至少18升/小時)。乙炔通過反應溶液直到轉化率足夠且時間足以持續反應之後,停止乙炔進料並在惰性氣氛(較佳為氮)中操作。用於此目的,反應混合物較佳地以氮自設備驅離,反應混合物冷卻之後,藉抽氣濾出形成的固體,於氮氣氛下再分散於溶劑中,清洗並在
真空乾燥箱中於80至180℃乾燥數小時。
於室溫,具有攪拌器和有護套的螺旋冷凝管之三頸瓶中先引入5852克四氫呋喃並於攪拌和氮氣通過時“脫氣”,所有的進一步反應在氮氣下進行。之後,添加70毫克的參(二亞苯基丙酮)二鈀和95毫克的4,5-雙(二苯基膦基)-9,9-二甲基且此混合物再攪拌15分鐘,之後添加於198克水中的198克膦酸。此反應溶液轉移至2升Büchi反應器中。攪拌此反應混合物時,反應器引入乙烯至2.5巴且此反應混合物加熱至80℃。吸收56克乙烯之後,此混合物冷卻至室溫並燒除自由的乙烯。
此反應混合物在旋轉式蒸發器中於最高60℃和350-10毫巴下蒸除溶劑。300克去礦質水加至殘渣中,混合物在氮氣氛下於室溫攪拌1小時。所得殘渣經過濾且濾液以200毫升甲苯萃取。此含水相於旋轉式蒸發器上於最高60℃和250-10毫巴下蒸除溶劑。31P NMR(D2O,偶合的):多重峰中的二重峰,36.7 ppm;乙膦酸。
0.5莫耳乙膦酸(根據實例1製得)於初時在作為溶劑的正丁醇中引入並以氮氣流惰性化,同時攪拌30分鐘並加熱至80℃。乙炔以18升/小時通過反應溶液,0.2莫耳%引發劑以3小時計量引入,令此混合物反應較長時
間。之後,以氮將乙炔驅除至設備外。反應混合物冷卻之後,形成的固體藉抽氣濾出並以丙酮再分散,清洗及在真空乾燥箱中於100℃乾燥4小時。以產率65%,得到34.8克伸乙基-1,2-雙(乙膦酸)(99.9重量%)和二乙膦酸(0.1重量%)之混合物。
0.5莫耳乙膦酸(根據實例1製得)於初時在作為溶劑的正丁醇中引入並以氮氣流惰性化,同時攪拌30分鐘並加熱至85℃。乙炔以20升/小時通過反應溶液,0.2莫耳%引發劑以2.5小時計量引入。持續反應30分鐘之後,中止乙炔進料並以氮將乙炔驅除至設備外。反應混合物冷卻之後,形成的固體藉抽氣濾出並以75克丙酮再分散,清洗及在真空乾燥箱中於100℃乾燥4小時。以產率65%,得到34.9克伸乙基-1,2-雙(乙膦酸)(98重量%)和二乙膦酸(2重量%)之混合物。
0.5莫耳乙膦酸(根據實例1製得)於初時在作為溶劑的正丁醇中引入並以氮氣流惰性化,同時攪拌30分鐘並加熱至90℃。乙炔以30升/小時通過反應溶液,0.2莫耳%引發劑以2小時計量引入。持續反應30分鐘之後,中止乙炔進料並以氮將乙炔驅除至設備外。反應混合物冷卻之後,形成的固體藉抽氣濾出並以75克丙酮再分散,清
洗及在真空乾燥箱中於100℃乾燥4小時。以產率63%,得到34.2克伸乙基-1,2-雙(乙膦酸)(90重量%)和二乙膦酸(10重量%)之混合物。
21.5克純的二乙膦酸加至根據實例2合成之伸乙基-1,2-雙(乙膦酸)(99.9重量%)和二乙膦酸(0.1重量%)之混合物中,以得到60重量%伸乙基-1,2-雙(乙膦酸)和40重量%二乙膦酸之混合物。前述二乙膦酸係根據EP-B-1544205的實例8製得,其中蒸餾依循其中的“Addition of sulfuric acid”步驟進行,以得到純的二乙膦酸,並因此而未轉化成二乙膦酸鹽。
34.8克純的二乙膦酸加至根據實例2合成之伸乙基-1,2-雙(乙膦酸)(99.9重量%)和二乙膦酸(0.1重量%)之混合物中,以得到50重量%伸乙基-1,2-雙(乙膦酸)和50重量%二乙膦酸之混合物。前述二乙膦酸係根據EP-B-1544205的實例8製得,其中蒸餾依循其中的“Addition of sulfuric acid”步驟進行,以得到純的二乙膦酸,並因此而未轉化成二乙膦酸鹽。
100份經磷改質的環氧樹脂與對應OH當量的酚樹脂混合並加熱至150℃。此液化該等組份。逐漸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-苯基咪唑且此混合物再度攪拌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分鐘並於之後添加2-苯基咪唑。應選擇苯基咪唑的量,使得膠凝時間為240秒。之後,進一步添加溶劑以建立標的黏度(黏度杯(flow cup))。之後,混合物濾經400微米篩網以移除過量的樹脂粒。之後,梭織玻璃織物(7628型,203克/平方米)浸入溶液中,直到織物完全潤濕。小心地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℃短時間初步固化,使得溶劑被移除且預浸物經預交聯。應檢測這些預浸物的膠凝時間。令8個預浸物積層並在受熱的加壓機中固化。經固化的積層物的樹脂含量為30-50%。
根據ASTM E831-06測定製得之模製物(積層物)之熱膨脹。
根據製造聚合物模製物之方法,使用100重量%雙酚A樹脂製造積層物。
根據實例2及後續以有機溶劑清洗產物,得到純的伸乙基-1,2-雙(乙膦酸)。根據製造聚合物模製物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A樹脂和10重量%伸乙基-1,2-雙(乙膦酸)所構成的組成物製造模製物。
首先,根據EP-B-1544205的實例8製造二乙膦酸,其中添加硫酸及之後蒸餾以得到純的二乙膦酸。根據製造聚合物模製物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A樹脂和10重量%二乙膦酸所構成的組成物製造模製物。
根據製造聚合物模製物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A樹脂和10重量%根據實例2之本發明之伸乙基-1,2-雙(乙膦酸)和二乙膦酸之混合物製造模製物。
根據製造聚合物模製物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A樹脂和10重量%根據實例3之本發明之伸乙基-1,2-雙(乙膦酸)和二乙膦酸之混合物製造模製物。
根據製造聚合物模製物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A樹脂和10重量%根據實例4之本發明之伸乙基-1,2-雙(乙膦酸)和二乙膦酸之混合物製造模製物。
根據製造聚合物模製物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A樹脂和10重量%根據實例5之本發明之伸乙基-1,2-雙(乙膦酸)和二乙膦酸之混合物製造模製物。
根據製造聚合物模製物的一般方法,使用由90重量%具硬化劑和觸媒的雙酚A樹脂和10重量%根據實例6之本發明之伸乙基-1,2-雙(乙膦酸)和二乙膦酸之混合物製造模製物。
相較於純積層物(實例7),包含本發明之伸乙基-1,2-雙(乙膦酸)和二乙膦酸之混合物的積層物之值降低;熱膨脹因此極低。二乙膦酸含量提高可獲進一步改良。
相較於以前技術(實例7),本發明之混合物的熱膨脹係數值較低,意謂本發明之產物使得所製得的模製物的膨脹較低並因此而符合尺寸安定性的要求。
1000克對酞酸二甲酯以720毫升乙二醇和230毫克Mn(OCOCH3)4*4H2O於溫度170-220℃在氮氣氛下轉酯化。分離甲醇之後,17.2克自實例4得到的本發明之混合物於220℃添加,添加350毫克Sb2O3之後,反應槽進一步加熱至250℃並同時施以真空。在2小時內,於0.2毫米汞柱和287℃進行此聚合反應。所得產物的熔點為240-244℃且磷含量為0.5%,其為粒形式。
所得聚合物粒與任何添加劑混合且彼等於溫度為250至290℃(PET-GR)在雙螺桿擠壓機(型號:Leistritz LSM 30/34)中摻合。排放此經均質化的聚合物條,在水浴中冷卻並於之後粒化。充分乾燥之後,該模製組成物在射出模製機(型號:Aarburg Allrounder)上於熔融溫度250至300℃(PET-GR)加工以得到試樣。
在1.6毫米厚的試樣上測定UL 94燃燒分級和LOI。1.6毫米厚的模製物具V-0等級和LOI為28%。
Claims (26)
- 一種至少一種式(I)的二膦酸與至少一種式(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R5為伸乙基、伸丁基、伸己基或伸辛基。
- 如申請專利範圍第1項之混合物,其中R1、R2、R3和R4相同或不同且各自為乙基和/或丁基,而R5係伸 乙基或伸丁基。
- 如申請專利範圍第1至3項中任一項之混合物,其包含0.1至99.9重量%式(I)的二膦酸和99.9至0.1重量%式(II)的二烷膦酸。
- 如申請專利範圍第1至3項中任一項之混合物,其包含60至99.9重量%式(I)的二膦酸和40至0.1重量%式(II)的二烷膦酸。
- 如申請專利範圍第1至3項中任一項之混合物,其包含80至99.9重量%式(I)的二膦酸和20至0.1重量%式(II)的二烷膦酸。
- 如申請專利範圍第1至3項中任一項之混合物,其包含90至99.9重量%式(I)的二膦酸和10至0.1重量%式(II)的二烷膦酸。
- 如申請專利範圍第1至3項中任一項之混合物,其包含95至99.9重量%式(I)的二膦酸和5至0.1重量%式(II)的二烷膦酸。
- 如申請專利範圍第1至3項中任一項之混合物,其包含98至99.9重量%式(I)的二膦酸和2至0.1重量%式(II)的二烷膦酸。
- 如申請專利範圍第1至3項中任一項之混合物,其中該二膦酸係伸乙基-1,2-雙(乙膦酸)、伸乙基-1,2-雙(丙膦酸)、伸乙基-1,2-雙(丁膦酸)、伸乙基-1,2-雙(戊膦 酸)、伸乙基-1,2-雙(己膦酸)、丁烷-1,2-雙(乙膦酸)、丁烷-1,2-雙(丙膦酸)、丁烷-1,2-雙(丁膦酸)、丁烷-1,2-雙(戊膦酸)、丁烷-1,2-雙(己膦酸)、己烷-1,2-雙(乙膦酸)、己烷-1,2-雙(丙膦酸)、己烷-1,2-雙(丁膦酸)、己烷-1,2-雙(戊膦酸)或己烷-1,2-雙(己膦酸),而該二烷膦酸係二乙膦酸、二丙膦酸、二丁膦酸、二戊膦酸或二己膦酸。
- 如申請專利範圍第1至3項中任一項之混合物,其包含98至99.9重量%的伸乙基-1,2-雙(乙膦酸)和2至0.1重量%的二乙膦酸。
- 如申請專利範圍第1至3項中任一項之混合物,其另包含至少一種增效劑,係為含氮化合物;鋁化合物;鎂化合物;錫化合物;銻化合物;鋅化合物;矽化合物;磷化合物;碳二亞胺、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)三聚異氰酸鹽與芳族多羧酸的低聚酯之氮化合物、或苯并胍胺、乙醯胍胺、參(羥乙基)三 聚異氰酸酯、乙內醯脲(allantoin)、甘脲(glycoluril)、三聚氰酸鹽、三聚氰酸鹽-環氧化物化合物、脲三聚氰酸脲、二氰醯胺、胍、胍磷酸鹽和/或硫酸鹽。
- 如申請專利範圍第12項之混合物,其中該增效劑為蜜勒胺(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、蜜勒聚磷酸鹽和/或三聚二氰亞胺聚磷酸鹽;或者為氫氧化鋁、多水高嶺土(halloysite)、藍寶石產物、水鋁土(boehmite)、奈水鋁土(nanoboehmite);或者為氫氧化鎂;或者為氧化錫;或者為氧化銻;或者為氧化鋅、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;或者為矽酸鹽和/或聚矽氧;或者 為膦酸和彼等的鹽、膦酸和彼等的鹽和/或膦氧化物、膦氮烯(phosphazene)和/或哌(焦)磷酸鹽。
- 如申請專利範圍第1至3項中任一項之混合物,其包含99至1重量%如申請專利範圍第1至11項中之至少一項之至少一種式(I)的二膦酸和至少一種式(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11項中之至少一項之混合物之方法,其包含令膦酸來源與炔在引發劑存在下反應。
- 如申請專利範圍第15項之方法,其中該膦酸來源是乙膦酸而該炔是乙炔、甲基乙炔、1-丁炔、1-己炔、2-己炔、1-辛炔、4-辛炔、1-丁炔-4-醇、2-丁炔-1-醇、3-丁炔-1-醇、5-己炔-1-醇、1-辛炔-3-醇、1-戊炔、苯基乙炔、三甲基矽基乙炔和/或二苯基乙炔,而該引發劑係具有氮-氮或氧-氧鍵的自由基引發劑,且反應溫度介於50至150℃。
- 如申請專利範圍第15或16項之方法,其中該自由基引發劑係2,2’-偶氮基雙(2-脒基丙烷)二氯化氫、2,2’-偶氮基雙(N,N’-二伸甲基異丁脒)二氯化氫、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、三級戊基過氧化氫和/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,其於溶劑中進行,且該溶劑包含直鏈或支鏈烷、經烷基取代的芳族溶劑、與水不互溶或僅部分與水互溶的醇或醚、水和/或乙酸。
- 如申請專利範圍第18項之方法,其中該醇係異丁醇和/或正丁醇、或包含這些醇與水之混合物。
- 一種如申請專利範圍第1至11項中之至少一項之混合物之用途,其在環氧樹脂之固化中作為加速劑、及用於電子應用。
- 一種如申請專利範圍第1至14項中之至少一項之混合物之用途,其作為阻燃劑、用以製造阻燃性聚合物模製組成物、用以製造阻燃性聚合物模製物和/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。
- 如申請專利範圍第21項之用途,其中該阻燃劑 為透明塗層和泡脹塗層的阻燃劑、木材和其他纖維素產品的阻燃劑、聚合物的反應性和/或非反應性阻燃劑。
- 一種阻燃性聚合物模製組成物,其包含0.5至50重量%如申請專利範圍第1至14項中之至少一項之混合物、50至99.5重量%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,其中組份的和為100重量%,該聚合物為熱塑性或熱固性聚合物。
- 一種阻燃性聚合物模製物,其包含0.5至50重量%如申請專利範圍第1至14項中之至少一項之混合物、50至99.5重量%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,其中組份的和為100重量%,該模製物為膜、纖絲或纖維。
- 一種阻燃性聚合物模製組成物,其包含2至30重量%如申請專利範圍第1至14項中之至少一項之混合物、60至94重量%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,其中組份的和為100重量%,該聚合物為熱塑性或熱固性聚合物。
- 一種阻燃性聚合物模製物,其包含2至30重量%如申請專利範圍第1至14項中之至少一項之混合物、60至94重量%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,其中組份的和為100重量%,該模製物為膜、纖絲或纖維。
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DE102011120190A1 (de) | 2011-12-05 | 2013-06-06 | Clariant International Limited | Mischungen von Aluminium-Hydrogenphosphiten mit Aluminiumsalzen, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
DE102011120191A1 (de) | 2011-12-05 | 2013-06-06 | Clariant International Ltd. | Mischungen von Aluminiumphosphit mit schwerlöslichen Aluminiumsalzen und Fremdionen, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
DE102011120200A1 (de) | 2011-12-05 | 2013-06-06 | Clariant International Ltd. | Flammschutzmittel-Mischungen enthaltend Flammschutzmittel und Aluminiumphosphite, Verfahren zu ihrer Herstellung und ihre Verwendung |
DE102011120218A1 (de) | 2011-12-05 | 2013-06-06 | Clariant International Ltd. | Alkali-Aliminium-Mischphosphite, Verfahren zur ihrer Herstellung sowie deren Verwendung |
DE102011121591A1 (de) | 2011-12-16 | 2013-06-20 | Clariant International Ltd. | Gemische aus Dialkylphosphinsäuren und Alkylphosphonsäuren, ein Verfahren zu deren Herstellung und ihre Verwendung |
DE102011121900A1 (de) | 2011-12-21 | 2013-06-27 | Clariant International Ltd. | Gemische von mindestens einer Dialkylphosphinsäure mit mindestens einer anderen, davon unterschiedlichen Dialkylphosphinsäure, Verfahren zu deren Herstellung und ihre Verwendung |
DE102014001222A1 (de) | 2014-01-29 | 2015-07-30 | Clariant lnternational Ltd | Halogenfreie feste Flammschutzmittelmischung und ihre Verwendung |
FR3053693B1 (fr) * | 2016-07-11 | 2018-08-17 | Arkema France | Composition liquide comprenant un additif a base de phosphore, son utilisation et materiau ou composition obtenu apres polymerisation de la composition |
DE102016213281A1 (de) * | 2016-07-20 | 2018-01-25 | Clariant Plastics & Coatings Ltd | Flammschutzmittelmischungen, ihre Herstellung und ihre Verwendung |
WO2019049668A1 (ja) * | 2017-09-07 | 2019-03-14 | 株式会社Adeka | 組成物及び難燃性樹脂組成物 |
CN109267345A (zh) * | 2018-09-17 | 2019-01-25 | 张家港市万能氨纶制品有限公司 | 一种防火氨纶丝 |
CN112194822B (zh) * | 2020-08-12 | 2021-12-21 | 天津科技大学 | 一种含磷阻燃剂、制备方法、改性环氧树脂 |
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US20150005421A1 (en) | 2015-01-01 |
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HK1198765A1 (zh) | 2015-06-05 |
CN104093727B (zh) | 2016-11-09 |
BR112014014148A2 (pt) | 2017-06-13 |
ES2710017T3 (es) | 2019-04-22 |
SG11201403119TA (en) | 2014-09-26 |
WO2013087179A1 (de) | 2013-06-20 |
EP2791152A1 (de) | 2014-10-22 |
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TW201335170A (zh) | 2013-09-01 |
JP2015509910A (ja) | 2015-04-02 |
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