CN109081944A - 二烷基二硫代次磷酸盐阻燃剂及其应用 - Google Patents
二烷基二硫代次磷酸盐阻燃剂及其应用 Download PDFInfo
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- CN109081944A CN109081944A CN201810684880.7A CN201810684880A CN109081944A CN 109081944 A CN109081944 A CN 109081944A CN 201810684880 A CN201810684880 A CN 201810684880A CN 109081944 A CN109081944 A CN 109081944A
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- Prior art keywords
- flame
- retardant
- compound
- melamine
- retardant polymer
- Prior art date
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Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 98
- -1 dithio hypophosphite Chemical compound 0.000 title claims abstract description 49
- 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 abstract description 52
- 229920000642 polymer Polymers 0.000 claims abstract description 38
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 24
- 239000000206 moulding compound Substances 0.000 claims abstract description 15
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 238000000465 moulding Methods 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 6
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 5
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 5
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 229910052718 tin Inorganic materials 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910003202 NH4 Inorganic materials 0.000 claims abstract description 3
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 3
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 229910052742 iron Inorganic materials 0.000 claims abstract description 3
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 3
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 3
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 3
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 3
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- 239000011701 zinc Substances 0.000 claims description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 229920000877 Melamine resin Polymers 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 238000001125 extrusion Methods 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- TVHALOSDPLTTSR-UHFFFAOYSA-H hexasodium;[oxido-[oxido(phosphonatooxy)phosphoryl]oxyphosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O TVHALOSDPLTTSR-UHFFFAOYSA-H 0.000 claims description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide 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
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 229920000388 Polyphosphate Polymers 0.000 claims description 4
- 150000001399 aluminium compounds Chemical class 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229940043430 calcium compound Drugs 0.000 claims description 4
- 150000001674 calcium compounds Chemical class 0.000 claims description 4
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 4
- HVHZIOXTVVFZGV-UHFFFAOYSA-N diphosphono hydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical class NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(=O)OP(O)(O)=O HVHZIOXTVVFZGV-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 150000002681 magnesium compounds Chemical class 0.000 claims description 4
- 150000002697 manganese compounds Chemical class 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
- 239000002245 particle 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
- 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 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 239000001205 polyphosphate Substances 0.000 claims description 4
- 235000011176 polyphosphates Nutrition 0.000 claims description 4
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 4
- 239000011135 tin Substances 0.000 claims description 4
- 150000003606 tin compounds Chemical class 0.000 claims description 4
- 150000003752 zinc compounds Chemical class 0.000 claims description 4
- 239000004114 Ammonium polyphosphate Substances 0.000 claims description 3
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 3
- 229920001276 ammonium polyphosphate Polymers 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 150000002019 disulfides Chemical class 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 3
- 150000003377 silicon compounds Chemical class 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- 229920001187 thermosetting polymer Polymers 0.000 claims description 3
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004254 Ammonium phosphate Substances 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-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
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 claims description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 claims description 2
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims description 2
- 235000019289 ammonium phosphates Nutrition 0.000 claims description 2
- OXIACMHTSQNJCY-UHFFFAOYSA-N bis[hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate 1,3,5-triazine-2,4,6-triamine Chemical class 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
- 238000003490 calendering Methods 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 238000000748 compression moulding Methods 0.000 claims description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 2
- 238000001746 injection moulding Methods 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 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 2
- 238000003475 lamination Methods 0.000 claims description 2
- 239000011572 manganese Substances 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
- 238000002156 mixing Methods 0.000 claims description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229920006254 polymer film Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229920001909 styrene-acrylic polymer Polymers 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000004634 thermosetting polymer Substances 0.000 claims description 2
- FOVKHTSFPJLUQN-UHFFFAOYSA-N 1-ethoxy-1,3,5-triazinane-2,4,6-trione Chemical class CCON1C(=O)NC(=O)NC1=O FOVKHTSFPJLUQN-UHFFFAOYSA-N 0.000 claims 1
- 238000000071 blow moulding Methods 0.000 claims 1
- 239000001177 diphosphate Substances 0.000 claims 1
- 235000011180 diphosphates Nutrition 0.000 claims 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims 1
- 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 1
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 229920005594 polymer fiber Polymers 0.000 claims 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 abstract description 3
- 230000000979 retarding effect Effects 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 229910001868 water Inorganic materials 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical group CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 7
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
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- 238000013329 compounding Methods 0.000 description 5
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- 230000000996 additive effect Effects 0.000 description 3
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- 239000004110 Zinc silicate Substances 0.000 description 1
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- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
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- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
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- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
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- 229920006115 poly(dodecamethylene terephthalamide) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920006128 poly(nonamethylene terephthalamide) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
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- 229920001225 polyester resin Polymers 0.000 description 1
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- 229920006380 polyphenylene oxide Polymers 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000005402 stannate group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ALHBQZRUBQFZQV-UHFFFAOYSA-N tin;tetrahydrate Chemical compound O.O.O.O.[Sn] ALHBQZRUBQFZQV-UHFFFAOYSA-N 0.000 description 1
- JUWGUJSXVOBPHP-UHFFFAOYSA-B titanium(4+);tetraphosphate Chemical compound [Ti+4].[Ti+4].[Ti+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JUWGUJSXVOBPHP-UHFFFAOYSA-B 0.000 description 1
- 230000007704 transition Effects 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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide 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
- 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
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- IPCXNCATNBAPKW-UHFFFAOYSA-N zinc;hydrate Chemical compound O.[Zn] IPCXNCATNBAPKW-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5398—Phosphorus bound to sulfur
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34928—Salts
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- C08K7/00—Use of ingredients characterised by shape
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
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- C—CHEMISTRY; METALLURGY
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- C08L2201/00—Properties
- C08L2201/22—Halogen free composition
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Abstract
本发明公开了一种二烷基二硫代次磷酸盐阻燃剂,结构式如下式(I)所示,式中,R1、R2独立地选自直链烷基或支链烷基,所述直链烷基或支链烷基的碳数为1~6;M选自Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、K、H或NH4,m为1~4。本发明公开了一种新型的无卤阻燃剂,具有阻燃性能优异、耐高温、低水溶性的优点;还公开了以其作为阻燃剂或阻燃协效剂,与其他阻燃剂复配制备阻燃聚合物模塑料以及阻燃聚合物模塑制品。
Description
技术领域
本发明涉及阻燃剂的技术领域,具体涉及一种二烷基二硫代次磷酸盐阻燃剂及其在阻燃剂组合物中的用途,以及涉及包含阻燃剂组合物制备的阻燃聚合物模塑料及阻燃聚合物模塑制品。
背景技术
高分子材料大多具有可燃性,但在很多应用领域,对材料提出了阻燃的要求,比如电器电子领域、电线电缆、家具、建筑、汽车内饰、纺织品等,即要求可燃易燃的高分子材料达到阻燃。
通常是通过向高分子材料中加入阻燃剂,来实现高分子材料的阻燃。传统的阻燃剂以溴系阻燃剂为主,但大量的研究发现,添加有溴系阻燃剂的阻燃高分子材料遇火灾燃烧后,会产生大量的浓烟和有毒物质,导致人员窒息,引起二次伤害;此外,这些材料的废弃物在高温回收时,容易生成二噁英等致癌物质,引起环境污染。
因此,针对卤系阻燃剂的问题,近年来开发新型无卤阻燃剂成为热点,出现了大量新型无卤阻燃剂,并在多个应用领域得到良好应用。
在无卤阻燃剂中,大致可以分为磷系阻燃剂、氮系阻燃剂、硅系阻燃剂以及无机氢氧化物类阻燃剂。其中,尤以磷系阻燃剂最为重要,这类阻燃剂具有高的阻燃效率,添加量低,对基材的力学性能影响较小。比如红磷、各种有机磷酸酯以及有机次磷酸盐等都得到了较好的应用。
二乙基次磷酸盐阻燃剂属于典型的有机次磷酸盐类阻燃剂,由于具有较高的磷含量,所以其具备了磷系阻燃剂较高的阻燃特性。但其阻燃过程较为复杂,在气相阻燃的同时兼具凝聚相阻燃。其具有阻燃性高、分解温度高、吸水低等优点,在阻燃聚酯、阻燃聚酰胺、阻燃聚氨酯等材料领域中均得到了较好的应用。
如Brehme S等(Phosphorus polyester versus aluminiumphosphinale inPBT.Polym Degrad Stab,2011,96(5):875-884)在制备阻燃聚酯(PBT)的过程中,以20%的二乙基次磷酸铝的添加量,使PBT树脂的LOI值达到45.5%,同时达到UL94/V0标准。
但该阻燃剂仍然存在一定的问题:
(1)在一些应用时,要实现较高的阻燃要求,还需要与含氮的化合物复配,如与MPP复配;
(2)其仍有一定的吸水性,在某些领域的应用仍受限制,如环氧覆铜板电子领域等。
因此,开发一种具有更高阻燃性能,同时具有耐高温低水溶性特点的新型阻燃剂,仍然是现有无卤阻燃体系面临的问题。
发明内容
本发明公开了一种新型的无卤阻燃剂及其应用,该无卤阻燃剂具有阻燃性能优异、耐高温、低水溶性的优点。
具体技术方案如下:
一种二烷基二硫代次磷酸盐,结构式如下式(I)所示:
式中,R1、R2独立地选自直链烷基或支链烷基,所述直链烷基或支链烷基的碳数为1~6;
M选自Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、K、H或NH4,m为1~4。
优选地,所述R1、R2独立地选自甲基、乙基、正丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基或异己基;
所述M选自Mg、Ca、Al、Sn、Ti或Zn;
进一步优选,所述二烷基二硫代次磷酸盐选自二甲基二硫代次磷酸铝、甲基乙基二硫代次磷酸铝、二乙基二硫代次磷酸铝、二丙基二硫代次磷酸铝、二丁基二硫代次磷酸铝、二甲基二硫代次磷酸锌、甲基乙基二硫代次磷酸锌、二乙基二硫代次磷酸锌、二丙基二硫代次磷酸锌、二丁基二硫代次磷酸锌、二甲基二硫代次磷酸钛、甲基乙基二硫代次磷酸钛、二乙基二硫代次磷酸钛、二丁基二硫代次磷酸钛。
发明人通过研究惊奇地发现,本发明公开的二烷基二硫代次磷酸盐化合物具有很好的阻燃性能,同时具有很高的热稳定性和低水溶性,这些特点表明该化合物可以用作高分子材料的高效阻燃剂。在其阻燃机理上,可能存在P、S和Al的协同作用。
经测试,所述二烷基二硫代次磷酸盐具有如下的物性参数:
颗粒尺寸为0.1~1000μm,优选为10~500μm,进一步优选为50~100μm;
水中的溶解度(20℃)为0.001~1%,优选为小于0.1%;
起始分解温度大于330℃;
堆密度为80~800g/L,优选为200~500g/L;
残留水分为0.1~5%,优选为小于0.5%。
本发明还公开了所述二烷基二硫代次磷酸盐的一种制备工艺,以制备二烷基二硫代次磷酸铝为例,具体为:
(1)将二烷基二硫代次磷酸钠溶液与硫酸铝溶液在酸性条件下反应,得到二烷基二硫代次磷酸铝沉淀物的悬浮液;
(2)所述悬浮液将过滤、洗涤并在120℃下干燥,粉碎至一定粒径,得到二烷基二硫代次磷酸铝阻燃剂。
其中,作为原料的二烷基二硫代次磷酸钠可以通过市售获得,或者通过如下方法制备:
(a)直链烯烃与磷化氢在引发剂存在并且在一定的温度和压力下可以发生自由基加成反应,生成二烷基磷化氢;
(b)将二烷基磷化氢与硫磺反应生成二烷基二硫代次磷酸;
(c)将二烷基二硫代次磷酸与氢氧化钠反应生成易溶于水的二烷基二硫代次磷酸钠盐。
本发明还公开了所述的二烷基二硫代次磷酸盐作为阻燃剂的用途。
包括:
以所述的二烷基二硫代次磷酸盐与其它添加剂组成的阻燃剂组合物。
按重量百分比计,所述阻燃剂组合物的组成包括:
二烷基二硫代次磷酸盐 50~99.9%;
阻燃协同剂 0.1~50%;
所述阻燃协同剂包括:
蜜白胺、蜜勒胺、三聚二氰亚胺、蜜胺磷酸盐、二蜜胺磷酸盐、五蜜胺三磷酸盐、三蜜胺二磷酸盐、四蜜胺三磷酸盐、六蜜胺五磷酸盐、蜜胺二磷酸盐、蜜胺四磷酸盐、蜜胺焦磷酸盐、蜜胺聚磷酸盐、蜜白胺聚磷酸盐、蜜勒胺聚磷酸盐、三聚二氰胺聚磷酸盐中的至少一种;
和/或,
三(羟乙基)异氰尿酸酯与芳族多羧酸的低聚物酯、苯并胍胺、三(羟乙基)异氰脲酸酯、脲囊素、甘脲、蜜胺氰脲酸酯、脲氰尿酸酯、双氰胺、胍中的至少一种;
和/或,
二烷基次磷酸盐、次磷酸盐、烷基亚磷酸盐、亚磷酸盐中的至少一种;
和/或,
碳二亚胺、单异氰酸酯、多异氰酸酯、苯乙烯-丙烯酸聚合物中的至少一种;
和/或,
磷酸铵、磷酸氢铵、磷酸二氢铵、聚磷酸铵中的至少一种;
和/或,
镁化合物、钙化合物、锌化合物、铝化合物、锰化合物、锡化合物、硅化合物中的至少一种。
上述列举的若干类添加剂种类,可以单独存在,也可以混合使用。
所述的二烷基次磷酸盐、次磷酸盐、烷基亚磷酸盐、亚磷酸盐,优选铝盐或锌盐。
所述的聚磷酸铵,分子式为(NH4PO3)Z,Z为1~10000。
所述的镁化合物、钙化合物、锌化合物、铝化合物、锰化合物、锡化合物、硅化合物中的化合物,包括氧化物、氢氧化物以及各种盐,如碳酸盐、硅酸盐、硼酸盐、锡酸盐等等。
优选地:
所述镁化合物,如氧化镁,氢氧化镁,水滑石,二水滑石,碳酸镁或碳酸镁钙。
所述钙化合物,如氢氧化钙,氧化钙,水铝钙石。
所述锌化合物,如氧化锌,氢氧化锌,水和氧化锌,碳酸锌,锡酸锌,羟基锡酸锌,碱性硅酸锌,碱性磷酸锌,碱性硼酸锌,碱性钼酸锌或碱性硫化锌。
所述铝化合物,如氧化铝,氢氧化铝,薄水铝石,水铝氧,磷酸铝,亚磷酸铝或烷基亚磷酸铝。
所述锰化合物,如氧化锰、氢氧化锰。
所述锡化合物,如氢氧化锡。
在上述优选原料基材上,进一步优选,所述阻燃剂组合物的组成包括:
二烷基二硫代次磷酸盐 70~95%;
阻燃协同剂 5~30%。
优选地,所述阻燃剂组合物的平均颗粒尺寸为0.1~3000μm,优选为0.1~1000μm,进一步优选为1~100μm。
堆密度为80~1500g/L,优选为200~1000g/L。
还包括:
直接以所述的二烷基二硫代次磷酸盐与基材及其它组分组成的阻燃聚合物模塑料,按重量百分比计,所述阻燃聚合物模塑料的组成包括:
或者,以所述的阻燃剂组合物与基材及其它组分组成的阻燃聚合物模塑料,按重量百分比计,所述阻燃聚合物模塑料的组成包括:
所述聚合物基材选自热塑性聚合物,如聚酯、聚酰胺、聚苯乙烯等、热塑性弹性体或热固性聚合物,如环氧树脂、聚氨酯等。
本发明可以使用的聚合物是热固性和热塑性聚合物。聚合物优选是单烯烃和二烯烃的聚合物;单烯烃和二烯烃之间或与其它乙烯基单体的共聚物;C5-C9烃树脂;聚苯乙烯类树脂;苯乙烯或α-甲基苯乙烯与二烯或与丙烯酸衍生物的共聚物;苯乙烯或α-甲基苯乙烯的接枝共聚物;含卤聚合物;α,β-不饱和酸和其衍生物的聚合物;不饱和醇和胺或其酰基衍生物或其缩醛的聚合物;环醚的均聚物和共聚物;聚缩醛;聚苯醚和聚苯硫醚;聚醚,聚酯或具有端羟基基团的聚丁二烯和另一方面衍生自脂族或芳族多异氰酸酯的聚氨酯,以及这些物质的前体。二胺和二羧酸,和/或氨基羧酸,或相应内酰胺的聚酰胺和共聚酰胺;二羧酸和二醇,和/或羟基羧酸,或相应内酯;聚脲,聚酰亚胺,聚酰胺酰亚胺,聚醚酰亚胺,聚酯酰亚胺,聚乙内酰胺和聚苯并咪唑;聚碳酸酯和聚酯碳酸酯;聚砜,聚醚砜,和聚醚酮;醛和酚、脲或蜜胺的交联聚合物。醇酸树脂;饱和或不饱和二羧酸与多元醇的共聚酯,以及乙烯基化合物作为交联剂的不饱和聚酯树脂,以及这些物质的含卤、阻燃改性;取代的可交联丙烯酸树脂;通过蜜胺树脂,脲树脂,异氰酸酯,异氰尿酸酯,多异氰酸酯或环氧树脂交联的醇酸树脂,聚酯树脂和丙烯酸树脂;衍生自脂族,环脂族,杂环,或芳族缩水甘油基化合物的交联环氧树脂;上述聚合物的混合物。
所述助剂选自抗氧剂、加工润滑剂、光稳定剂、抗静电剂等;所述填料选自玻纤、碳纤、矿物填料等。
在上述优选原料基材上,进一步优选,所述阻燃聚合物模塑料的组成包括:
将上述各原料混合均匀后,经熔融挤出、冷却后即得到所述阻燃聚合物模塑料。
具体为:将各原料在混合器中混合,在相对高的处理温度下在配混组合装置中将聚合物熔体匀化,并随后引出该匀化的聚合物挤出物,冷却,再将它分成多个部分。
优选的处理温度,对于聚苯乙烯是170~200℃,对于聚丙烯是
200~300℃,对于PET是250~290℃,对于PBT是230~270℃,对于PA6是260~290℃,对于PA66是260~290℃,对于高温尼龙(如PA46,PA4T,PA6T,PA9T,PA10T,PA12T等)是290~320℃,对于聚碳酸酯是280~320℃。
配混组合装置优选来自单螺杆挤出机,多区螺杆,或双螺杆挤出机。
作为螺杆直径(D)倍数,挤出机(配混组合装置)的有效螺杆长度(L)优选为4~200D(即长径比为4~200),优选10~50D。
可用于本发明的配混组合装置是双螺杆挤出机,单螺杆挤出机,三段螺杆和/或短压缩区螺杆的多段螺杆挤出机,捏合机,具有3至12个围绕静止芯旋转的小螺杆的环挤出机,行星齿轮挤出机,排气挤出机,串联挤出机,具有反旋转双螺杆的配混机等。
用于本发明的有效螺杆长度在单螺杆挤出机的情况下是20至40D,在多段螺杆挤出机的情况下是25D,包括加料部分(L=10D),过渡部分(L=6D),冲挤部分(L=9D);在双螺杆挤出机的情况下是8至48D。制备得到的阻燃聚合物模塑物,残余水分含量为0.01至10%重量,优选为0.1~1%重量。
还包括:
一种阻燃聚合物模塑制品,以所述的阻燃聚合物模塑料为原料,经注塑、压塑、吹塑、铸模、压延、层压或涂覆工艺后制备得到所述阻燃聚合物模塑制品;
所述阻燃聚合物模塑制品包括阻燃聚合物膜、阻燃聚合物长丝或阻燃聚合物纤维,应用于电气和电子领域。使用本发明制备的阻燃聚合物模塑制品作为灯部件,如灯座和灯架,插头和线路板,线圈架,用于电器、电容器或接触器的外壳,和电路开关,继电器外壳和反射器等。
与现有技术相比,本发明具有如下优点:
本发明提供了一种新型的二烷基二硫代次磷酸盐阻燃剂,与高分子材料的相容性好,且具有优异的热稳定性,起始分解温度不低于340℃;可作为阻燃剂,也可作为阻燃协效剂,与其他阻燃剂复配用作高分子材料的阻燃体系。
具体实施方式
实施例1二乙基二硫代次磷酸铝的制备
分别配制浓度20wt%的二乙基二硫代次磷酸钠水溶液1056g和浓度30wt%的硫酸铝水溶液228g,向反应器中加入脱盐水1000g,并加入浓度25wt%的硫酸水溶液50g,升温至80℃,开始向反应釜内按比例同步滴加二乙基二硫代次磷酸钠水溶液和硫酸铝溶液,得到二乙基二硫代次磷酸铝沉淀物,2小时滴加完成,保温1小时,然后过滤、洗涤、烘干,得到二乙基二硫代次磷酸铝阻燃剂185g(收率95%)。
经测试,产物的起始分解温度350℃,其水中溶解度为0.04%。
对产物进行能谱分析,元素分析结果如表1所示。
表1
元素 | wt% |
C K | 31.9 |
S K | 42.5 |
Al K | 5.9 |
P K | 19.7 |
表1中各元素含量与理论计算量很接近,表明所制备的化合物是二乙基二硫代次磷酸铝化合物。
实施例2二异丁基二硫代次磷酸铝的制备
分别配制浓度20wt%的二异丁基二硫代次磷酸钠水溶液1392g和浓度30wt%的硫酸铝溶液228g,向反应器中加入脱盐水1500g,并加入浓度25wt%的硫酸溶液75g,升温至80℃,开始向反应釜内按比例同步滴加二异丁基二硫代次磷酸钠水溶液和硫酸铝溶液,得到二异丁基二硫代次磷酸铝沉淀物,2小时滴加完成,保温1小时,然后过滤、洗涤、烘干,得到二异丁基二硫代次磷酸铝阻燃剂254g(收率97%)。
经测试,产物的起始分解温度350℃,其水中溶解度为0.02%。
对产物进行能谱分析,元素分析结果如表2所示。
表2
元素 | wt% |
C K | 47.6 |
S K | 32.2 |
Al K | 4.7 |
P K | 15.5 |
表2中各元素含量与理论计算量很接近,表明所制备的化合物是二异丁基二硫代次磷酸铝化合物。
实施例3二乙基二硫代次磷酸锌的制备
分别配制浓度20wt%的二乙基二硫代次磷酸钠水溶液1056g和浓度30wt%的硫酸锌溶液322g,向反应器中加入脱盐水1700g,并加入浓度25wt%的硫酸溶液85g,升温至80℃,开始向反应釜内按比例同步滴加二乙基二硫代次磷酸钠水溶液和硫酸锌溶液,得到二乙基二硫代次磷酸锌沉淀物,2小时滴加完成,保温1小时,然后过滤、洗涤、烘干,得到二乙基二硫代次磷酸锌阻燃剂205g(收率92%)。
经测试,产物的起始分解温度350℃,其水中溶解度为0.1%。
对产物进行能谱分析,元素分析结果如表3所示。
表3
元素 | wt% |
C K | 27.8 |
S K | 36.2 |
Zn K | 18.2 |
P K | 17.8 |
表3中各元素含量与理论计算量很接近,表明所制备的化合物是二乙基二硫代次磷酸锌化合物。
对比例1
二乙基次磷酸铝,起始分解温度为320℃,水中溶解度为0.1%。
对比例2
二乙基次磷酸锌,起始分解温度为330℃,水中溶解度为4.0%。
应用例1
采用55wt%的尼龙66,30wt%的玻纤,10wt%的实施例1制备的二乙基二硫代次磷酸铝和5wt%三聚氰胺聚磷酸盐(MPP),按照现有制备方法制得阻燃玻纤增强尼龙66,并制样测试阻燃性能,材料阻燃达到UL94V0
(1.6mm)。
应用例2
采用55wt%的PBT,30wt%的玻纤,10wt%的实施例1制备的二乙基二硫代次磷酸铝和5wt%三聚氰胺聚磷酸盐(MPP),按照所述一般规程制得阻燃玻纤增强PBT,并制样测试阻燃性能,材料阻燃达到UL94V0(1.6mm)。
Claims (10)
1.一种二烷基二硫代次磷酸盐,其特征在于,结构式如下式(I)所示:
式中,R1、R2独立地选自直链烷基或支链烷基,所述直链烷基或支链烷基的碳数为1~6;
M选自Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、K、H或NH4,m为1~4。
2.根据权利要求1所述的二烷基二硫代次磷酸盐,其特征在于,所述R1、R2独立地选自甲基、乙基、正丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、正己基或异己基;
所述M选自Mg、Ca、Al、Sn、Ti或Zn;
所述二烷基二硫代次磷酸的颗粒尺寸为0.1~1000μm。
3.一种根据权利要求1或2所述的二烷基二硫代次磷酸盐作为阻燃剂的用途。
4.一种阻燃剂组合物,其特征在于,包括根据权利要求1或2所述的二烷基二硫代次磷酸盐;
按重量百分比计,所述阻燃剂组合物的组成包括:
二烷基二硫代次磷酸盐 50~99.9%;
阻燃协同剂 0.1~50%;
所述阻燃协同剂包括:
蜜白胺、蜜勒胺、三聚二氰亚胺、蜜胺磷酸盐、二蜜胺磷酸盐、五蜜胺三磷酸盐、三蜜胺二磷酸盐、四蜜胺三磷酸盐、六蜜胺五磷酸盐、蜜胺二磷酸盐、蜜胺四磷酸盐、蜜胺焦磷酸盐、蜜胺聚磷酸盐、蜜白胺聚磷酸盐、蜜勒胺聚磷酸盐、三聚二氰胺聚磷酸盐中的至少一种;
和/或,
三(羟乙基)异氰尿酸酯与芳族多羧酸的低聚物酯、苯并胍胺、三(羟乙基)异氰脲酸酯、脲囊素、甘脲、蜜胺氰脲酸酯、脲氰尿酸酯、双氰胺、胍中的至少一种;
和/或,
二烷基次磷酸盐、次磷酸盐、烷基亚磷酸盐、亚磷酸盐中的至少一种;
和/或,
磷酸铵、磷酸氢铵、磷酸二氢铵、聚磷酸铵中的至少一种;
和/或,
碳二亚胺、单异氰酸酯、多异氰酸酯、苯乙烯-丙烯酸聚合物中的至少一种;
和/或,
镁化合物、钙化合物、锌化合物、铝化合物、锰化合物、锡化合物、硅化合物中的至少一种。
5.根据权利要求4所述的阻燃剂组合物,其特征在于,所述阻燃剂组合物的平均颗粒尺寸为0.1~3000μm。
6.一种阻燃聚合物模塑料,其特征在于,包括根据权利要求1或2所述的二烷基二硫代次磷酸盐;
按重量百分比计,所述阻燃聚合物模塑料的组成包括:
7.一种阻燃聚合物模塑料,其特征在于,包括根据权利要求4或5所述的阻燃剂组合物;
按重量百分比计,所述阻燃聚合物模塑料的组成包括:
8.根据权利要求6或7所述的阻燃聚合物模塑料,其特征在于,所述聚合物基材选自热塑性聚合物、热塑性弹性体或热固性聚合物。
9.一种根据权利要求6或7所述的阻燃聚合物模塑料的制备方法,其特征在于,将各原料混合均匀后,经熔融挤出、冷却后得到所述阻燃聚合物模塑料;
采用单螺杆挤出机或双螺杆挤出机进行熔融挤出。
10.一种阻燃聚合物模塑制品,其特征在于,以根据权利要求6或7所述的阻燃聚合物模塑料为原料,经注塑、压塑、吹塑、铸模、压延、层压或涂覆工艺后制备得到所述阻燃聚合物模塑制品;
所述阻燃聚合物模塑制品包括阻燃聚合物膜、阻燃聚合物长丝或阻燃聚合物纤维。
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