CN115536909B - Halogen-free flame retardant composition and preparation method and application thereof - Google Patents
Halogen-free flame retardant composition and preparation method and application thereof Download PDFInfo
- Publication number
- CN115536909B CN115536909B CN202210684184.2A CN202210684184A CN115536909B CN 115536909 B CN115536909 B CN 115536909B CN 202210684184 A CN202210684184 A CN 202210684184A CN 115536909 B CN115536909 B CN 115536909B
- Authority
- CN
- China
- Prior art keywords
- flame retardant
- halogen
- retardant composition
- hypophosphite
- free flame
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 227
- 239000000203 mixture Substances 0.000 title claims abstract description 168
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 title claims abstract description 112
- 238000002360 preparation method Methods 0.000 title claims abstract description 37
- 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 99
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 78
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 52
- 238000002156 mixing Methods 0.000 claims abstract description 28
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims abstract description 26
- 229910052751 metal Inorganic materials 0.000 claims abstract description 21
- 239000002184 metal Substances 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 16
- -1 amine cations Chemical class 0.000 claims description 82
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 33
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 28
- 229920000877 Melamine resin Polymers 0.000 claims description 27
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 27
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 26
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000011787 zinc oxide Substances 0.000 claims description 18
- 229910001377 aluminum hypophosphite Inorganic materials 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 17
- 239000000347 magnesium hydroxide Substances 0.000 claims description 17
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 17
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 16
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 11
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 10
- 150000004692 metal hydroxides Chemical class 0.000 claims description 10
- 229910044991 metal oxide Inorganic materials 0.000 claims description 9
- 150000004706 metal oxides Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 claims description 7
- 229960004887 ferric hydroxide Drugs 0.000 claims description 7
- 229910001195 gallium oxide Inorganic materials 0.000 claims description 7
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 claims description 7
- 229910001381 magnesium hypophosphite Inorganic materials 0.000 claims description 7
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims description 6
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- SEQVSYFEKVIYCP-UHFFFAOYSA-L magnesium hypophosphite Chemical compound [Mg+2].[O-]P=O.[O-]P=O SEQVSYFEKVIYCP-UHFFFAOYSA-L 0.000 claims description 6
- 239000000467 phytic acid Substances 0.000 claims description 6
- 235000002949 phytic acid Nutrition 0.000 claims description 6
- 229940068041 phytic acid Drugs 0.000 claims description 6
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 6
- 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 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 claims description 5
- CQYBWJYIKCZXCN-UHFFFAOYSA-N diethylaluminum Chemical compound CC[Al]CC CQYBWJYIKCZXCN-UHFFFAOYSA-N 0.000 claims description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
- LOAHJABDATVOQU-UHFFFAOYSA-N ethyl(methyl)alumane Chemical compound C[AlH]CC LOAHJABDATVOQU-UHFFFAOYSA-N 0.000 claims description 5
- 229910021506 iron(II) hydroxide Inorganic materials 0.000 claims description 5
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 5
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 5
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 5
- 229940007718 zinc hydroxide Drugs 0.000 claims description 5
- XXSPKSHUSWQAIZ-UHFFFAOYSA-L 36026-88-7 Chemical compound [Ni+2].[O-]P=O.[O-]P=O XXSPKSHUSWQAIZ-UHFFFAOYSA-L 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 4
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 229910001382 calcium hypophosphite Inorganic materials 0.000 claims description 4
- 229940064002 calcium hypophosphite Drugs 0.000 claims description 4
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 4
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 claims description 4
- 229910001383 lithium hypophosphite Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000395 magnesium oxide Substances 0.000 claims description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 4
- 229910001380 potassium hypophosphite Inorganic materials 0.000 claims description 4
- CRGPNLUFHHUKCM-UHFFFAOYSA-M potassium phosphinate Chemical compound [K+].[O-]P=O CRGPNLUFHHUKCM-UHFFFAOYSA-M 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- CNALVHVMBXLLIY-IUCAKERBSA-N tert-butyl n-[(3s,5s)-5-methylpiperidin-3-yl]carbamate Chemical compound C[C@@H]1CNC[C@@H](NC(=O)OC(C)(C)C)C1 CNALVHVMBXLLIY-IUCAKERBSA-N 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 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 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 2
- 229930024421 Adenine Natural products 0.000 claims description 2
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 claims description 2
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims description 2
- 229960000643 adenine Drugs 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- SZOADBKOANDULT-UHFFFAOYSA-K antimonous acid Chemical compound O[Sb](O)O SZOADBKOANDULT-UHFFFAOYSA-K 0.000 claims description 2
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
- WMWLMWRWZQELOS-UHFFFAOYSA-N bismuth(III) oxide Inorganic materials O=[Bi]O[Bi]=O WMWLMWRWZQELOS-UHFFFAOYSA-N 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000292 calcium oxide Substances 0.000 claims description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229940104302 cytosine Drugs 0.000 claims description 2
- 229940029575 guanosine Drugs 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims description 2
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 claims description 2
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 claims description 2
- 229940035893 uracil Drugs 0.000 claims description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 claims 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims 2
- VASIZKWUTCETSD-UHFFFAOYSA-N oxomanganese Chemical compound [Mn]=O VASIZKWUTCETSD-UHFFFAOYSA-N 0.000 claims 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 claims 2
- 150000007973 cyanuric acids Chemical class 0.000 claims 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 claims 1
- DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 claims 1
- VEETXHURKVEAET-UHFFFAOYSA-N methyl(propyl)alumane Chemical compound C[AlH]CCC VEETXHURKVEAET-UHFFFAOYSA-N 0.000 claims 1
- 238000001338 self-assembly Methods 0.000 claims 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims 1
- 229910001887 tin oxide Inorganic materials 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 5
- 239000011347 resin Substances 0.000 abstract description 5
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 239000004033 plastic Substances 0.000 abstract description 3
- 229920003023 plastic Polymers 0.000 abstract description 3
- 238000005034 decoration Methods 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000806 elastomer Substances 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 239000002861 polymer material Substances 0.000 description 25
- 238000003756 stirring Methods 0.000 description 20
- 239000004114 Ammonium polyphosphate Substances 0.000 description 19
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 19
- 229920001276 ammonium polyphosphate Polymers 0.000 description 19
- 239000004743 Polypropylene Substances 0.000 description 17
- 229920001155 polypropylene Polymers 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 15
- 230000004584 weight gain Effects 0.000 description 15
- 235000019786 weight gain Nutrition 0.000 description 15
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 239000011574 phosphorus Substances 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 229960005141 piperazine Drugs 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 10
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 8
- BAERPNBPLZWCES-UHFFFAOYSA-N (2-hydroxy-1-phosphonoethyl)phosphonic acid Chemical compound OCC(P(O)(O)=O)P(O)(O)=O BAERPNBPLZWCES-UHFFFAOYSA-N 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 238000002485 combustion reaction Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
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Classifications
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Abstract
The invention relates to a halogen-free flame retardant composition, a preparation method and application thereof, wherein the halogen-free flame retardant composition is a flame retardant composition composed of organic phosphonate, cyanuric acid and/or metal cyanurate and hypophosphite; the halogen-free flame retardant composition is obtained by uniformly mixing organic phosphonate, cyanuric acid and/or metal cyanurate and hypophosphite or mixing organic phosphonate, cyanuric acid and/or metal cyanurate, hypophosphite and other components in proportion. The flame retardant composition has excellent flame retardance and good cost performance, has little influence on the mechanical properties of resin, and is suitable for various industrial fields requiring flame retardant resin components, such as new energy battery shells and electronic components, internal and external decoration materials of vehicles such as automobiles, coating materials of electronic and electric components, covers or chassis, plastic components for household appliances such as refrigerators and air conditioners, OA equipment components such as office and household appliances, and elastomer coating materials for cables in IT industry, new energy charging cables, and the like.
Description
Technical Field
The invention belongs to the technical field of halogen-free flame retardants, relates to a halogen-free flame retardant composition, a preparation method and application thereof, and in particular relates to a flame retardant composition composed of organic phosphonate, cyanuric acid or metal salt and hypophosphite.
Background
The polypropylene (PP) has the advantages of light weight, no toxicity, small density, excellent mechanical property, good electrical insulation, good chemical corrosion resistance, low price, easy molding and processing and the like, and is widely applied to the fields of electronic appliances, communication equipment, household appliances, automobiles, building materials and the like. However, PP has poor flame resistance, is easy to burn, has an oxygen index of only 17.4%, generates a large amount of combustion heat, and is accompanied by a combustion dripping phenomenon, thereby easily causing a fire hazard. Therefore, the PP flame retardant problem is becoming one of the hot spots of research.
The halogen flame retardant plays an important role in PP flame retardance due to the high-efficiency flame retardance, and the common brominated flame retardants such as decabromodiphenylethane, octabromoether flame retardants, bromotriazine, TBC and the like have high flame retardance efficiency on PP.
The phosphorus flame retardant has the advantages of low toxicity, low smoke and good cost performance, and is most attractive in the field of flame retardant development. The red phosphorus is an inorganic phosphorus flame retardant with excellent performance, has small smoke generation amount and wide application range, can be used independently, and can also be used together with other flame retardants. The modification treatment is necessary for solving the problems that red phosphorus is easy to absorb moisture, oxidize, release highly toxic gas, explode dust and the like in the use process. The most effective method for modifying red phosphorus is surface coating. The decomposition temperature of the modified red phosphorus can be increased from 240 ℃ to 320 ℃.
The nitrogen flame retardant has the advantages of low toxicity, high decomposition temperature, suitability for processing and the like, and becomes a very popular flame retardant. The most commonly used nitrogen-based flame retardant is melamine and its derivatives. The nitrogen flame retardant is usually compounded with other flame retardants such as phosphorus flame retardants and halogen flame retardants.
Chinese patent CN200580005684.3 discloses a flame retardant composition which is formed by adding a component (D) to a flame retardant composition composed of a component (a), a component (B), and a component (C); wherein the total of the components (A) and (B) is 100 parts by weight; the component (A) is a methylphenidate in an amount of 1 to 99 parts by weightSalts of oxazine with inorganic phosphorus compounds, such as piperazine phosphate, piperazine pyrophosphate, piperazine polyphosphate or mixtures of these piperazine salts; the component (B) is 99 to 1 part by weight, which is a salt of melamine with an inorganic phosphorus compound, such as melamine phosphate, melamine pyrophosphate, melamine polyphosphate or a mixture of these salts; the component (C) may be mixed with other flame retardants and flame retardant auxiliaries, or may be mixed with antioxidants such as phenolic antioxidants, phosphorus antioxidants and sulfur antioxidants; an ultraviolet absorber, a hindered amine compound, and other weather resistance improving agents; 0 to 50 weight parts of optional components of resin mixture such as nucleating agent, heavy metal inerting agent, metal soap, hydrotalcite, filler, antistatic agent, lubricant, pigment, antibacterial agent, mildew inhibitor, rodenticide and the like; the component (D) has a viscosity of 5000mm at 25 ℃ of 0.01 to 20 parts by weight 2 Silicone oil of/s or less. Other flame retardants described in this patent include inorganic flame retardants and organic flame retardants such as halogen flame retardants, phosphate flame retardants, ammonium polyphosphate, magnesium hydroxide, aluminum hydroxide and other metal hydroxides. Inorganic compounds such as zinc oxide, titanium oxide, aluminum oxide, magnesium hydroxide, hydrotalcite, talc, etc. of inorganic flame retardants, and surface-treated products thereof, in particular, some inorganic flame retardants coated with ultrafine particles or nanoparticles. Examples of the organic flame retardant include melamine cyanurate, pentaerythritol, and polytetrafluoroethylene. The flame retardant efficiency is improved by adding these components. It is particularly mentioned that polytetrafluoroethylene anti-dripping agents are preferably added.
The particle diameter, melting point, viscosity, etc. of the flame retardant aid may be selected so as to have excellent flame retarding effect or powder characteristics.
Further, chinese patent CN200880111829.1 reports an improvement of the above-mentioned patent, in which a monoamide compound of a higher aliphatic carboxylic acid and/or a monoester compound obtained by reacting a higher aliphatic carboxylic acid with a 1-to 3-membered alcohol compound are added mainly in an amount of 0.01 to 20 parts by mass. Chinese patent CN201580062883.1 reports an improved technique based on the above patent, mainly the addition of bicyclic phosphate compounds. Chinese patent CN201680004956.6 reports an improved technique based on the above patent, mainly the addition of aliphatic dicarboxylic ether ester compounds.
The common feature of the above patents is that the flame retardance and other properties are improved by silicone oil surface treatment and addition of other flame retardant additives on the basis of the phosphates of piperazine and melamine.
The literature (preparation of melamine polyphosphonates and performance studies of flame retardant polyolefins thereof, shuoshi university, 2015) has investigated the synthesis and use of melamine hydroxyethylidene bisphosphonate (MHEDP). When 12% MHEDP, 12% ammonium polyphosphate (APP) and 6% Melamine Phosphate (MP) are added into polypropylene (PP), the PP can reach UL-94V-0 grade (3.2 mm), the limiting oxygen index reaches 35%, and meanwhile, the mechanical property is kept better. The literature (synthesis of new melamine based flame retardants and their use in flame retardant polypropylene, the university of east China, published treatises, 2012) reports the synthesis of a new melamine phosphonate by reaction of ethylenediamine tetramethylene phosphonic acid with melamine, which is used in combination with APP for flame retardant PP.
Literature (research of organic-metal hybrid compound flame-retardant polypropylene [ J ]. Chinese plastics, 2018, 32 (5): 73-78) reports that an Intumescent Flame Retardant (IFR) is prepared by compounding an organic-metal hybrid triazine compound (SCTCFA-ZnO) and APP, and the influence of the synergistic effect of the SCTCFA-ZnO/APP on the flame retardant property of the PP composite material is researched through the characterization methods such as LOI test, vertical combustion test, cone calorimetric analysis, thermal weightlessness analysis, scanning electron microscope analysis and the like. The result shows that the APP and SCTCFA-ZnO can be compounded to improve the flame retardant property of the PP material. When the IFR addition amount is 25% (mass fraction, the same applies below) and the APP/SCTCFA-Zn O mass ratio is 2/1, the LOI of the composite material is highest and reaches 31.1%, and the UL 94V-0 level is achieved.
The flame retardant technologies reported in the above documents all use APP in a large proportion, and inorganic phosphorus flame retardants such as ammonium polyphosphate used for flame retardation of polyolefin as general-purpose resins are liable to cause aggregation due to poor compatibility with polymers, and thus cause degradation or instability of product performance; in addition, inorganic ammonium polyphosphate is easily hydrolyzed, resulting in poor moisture resistance of flame retardant products, and deterioration of electrical properties and the like.
The literature (flame retardant application of dicyandiamide cyanurate in polypropylene [ J ]. Plastic industry, 2021, 4 months, 49, 4 th edition, 163-168) Liu Qin et al reports that flame retardant polypropylene (Liu Qin et al) was compounded with dicyandiamide cyanurate and Jiao Pai, and when the compounding ratio of dicyandiamide cyanurate to Jiao Pai was 1:2, the addition amount was 24%, UL94 reached V0 (1.5 mm), the LOI was 29.3%, the addition 21% LOI was 27.5% (UL 94V 0,2.5 mm), and the addition 30% LOI was 32.2%.
Heretofore, halogen-free flame retardant systems for polyolefins which have been industrialized can be divided into APP/polyol based APP (typically pentaerythritol and its derivatives)/melamine and APP and triazine char formers, and piperazine pyrophosphate and melamine polyphosphate (MPP) systems. In recent years, some new flame-retardant systems are reported in literature, such as novel organic phosphonates reported by Zhao Haizhu, you Lihua and the like, which are compounded with APP for use, but the addition amount is large, and the problem of hygroscopicity of APP is not solved. In contrast, the piperazine pyrophosphate and melamine polyphosphate (MPP) system developed as typified by japanese patent No. Ai Dike (chinese patent No. CN 200580005684.3) also has problems of hygroscopicity of inorganic salts and easiness of agglomeration of powder, but the surface treatment can improve the system, but has problems of unstable flame retardant property, poor durability of moisture resistance, and the like.
Disclosure of Invention
Aiming at the defects of the prior art, the invention discovers that the composition of the organic phosphonate, cyanuric acid or metal salt and hypophosphite thereof has excellent flame retardance and can overcome the defects of powder agglomeration, hygroscopicity of flame-retardant products and the like in repeated intensive researches, thereby realizing efficient flame retardance and excellent moisture resistance of the flame retardant composition. The invention aims to provide a halogen-free flame retardant composition and a preparation method and application thereof, in particular to a flame retardant composition compounded by organic phosphonate, cyanuric acid or metal salt and hypophosphite thereof and a preparation method and application thereof. The flame retardant composition provided by the invention has the advantages of easily available raw materials and easiness in realizing industrial production and application. The flame retardant composition can be widely applied to flame retardance of materials such as polyolefin, polyamide, polyester, polyurethane and the like, and has good application prospect as a flame retardant.
In order to achieve the above purpose, the invention adopts the following technical scheme:
a halogen-free flame retardant composition comprising the following components in parts by weight:
75-90 parts of organic phosphonate;
9-15 parts of cyanuric acid and/or cyanuric acid metal salt;
1-10 parts of hypophosphite;
the molecular structure of the organic phosphonate consists of organic amine cations with the structure shown in the formula (I), metal ions with the structure shown in the formula (II) and organic phosphonic acid anions with the structure shown in the formula (III) or the formula (IV), and the total charge value of the anions is equal to the total charge value of the cations;
wherein m=1, 2 or 3; n=1, 2, 3, 4 or 5;0<p≤2，0≤q<2, and p+q=2; 0<x≤2，0≤y<2, and x+y=2; h=1, 2, 3, 4, 5, 6 or 7; r, R * And R' "are each independently selected from alkyl groups with or without heteroatom substituents, aromatic hydrocarbon groups with or without heteroatom substituents, cyclic groups formed by carbon atoms and other atoms, or cyclic groups with heteroatom substituents; r 'and R' are each independently selected from one of H, alkyl and aryl groups or R 'and R' form a cyclic group in the same molecule; m is more than one metal element.
As a preferable technical scheme:
a halogen-free flame retardant composition as described above, the organic phosphonate being prepared by self-assembling reaction of organic phosphonic acid, metal oxide and/or metal hydroxide and organic amine in a certain molar ratio into a reactor;
the molar ratio of the organic amine to the metal oxide and/or the metal hydroxide is 1:0.1-5.0, the molar ratio of the organic amine to the sum of the molar amount of metal ions in the metal oxide and/or the metal hydroxide multiplied by the metal valence to the molar amount of the organic phosphonic acid is 1:1/v-1, and v is the total number of P-O-H units contained in one organic phosphonic acid molecule.
The halogen-free flame retardant composition has the advantages that the organic phosphonic acid is phytic acid or has more than one of general structures shown in (A), (B), (C) and (D); specifically, phytic acid, methylphosphonic acid, phenylphosphonic acid, 2-carboxyethylmethylphosphinic acid, 2-carboxyethylphenylphosphinic acid, N-bis (phosphonomethyl) glycine, 3-aminopropane-1-phosphonic acid, hydroxyethylidene diphosphonic acid, aminotrimethylene phosphonic acid, ethylenediamine tetramethylene phosphonic acid, 2-phosphonic butane-1, 2, 4-tricarboxylic acid, phosphonoglycolic acid, diethylenetriamine pentamethylene phosphonic acid, bis 1, 6-hexylidene triamine pentamethylene phosphonic acid, and the like;
in the formula (A), R 1 Is alkyl, aryl, aralkyl, and the like,Or cyclic groups of carbon atoms with other atoms, e.g. nitrogen, phosphorus, oxygen and sulfur, where R 3 Is hydrogen, alkyl or aryl, X is hydroxy, mercapto, carboxyl, nitro or sulfo;
in the formula (B), R 2 Is alkyl, aryl, pyridyl, piperidinyl, and the like,Or cyclic groups of carbon atoms with other atoms, e.g. nitrogen, phosphorus, oxygen and sulfur, R' 2 A cyclic group which is a hydroxyl group, an alkyl group, an aromatic hydrocarbon group, or a carbon atom and other atoms;
in the formula (C), R 4 And R is 5 Each independently selected from alkyl, aromatic hydrocarbon groups, or cyclic groups of carbon atoms with other atoms such as nitrogen, phosphorus, oxygen, and sulfur; r is R 6 Is alkyl, aryl, aralkyl, and the like,Or cyclic groups of carbon atoms with other atoms such as nitrogen, phosphorus, oxygen and sulfur;
in the formula (D), R 7 Is alkyl, aryl, aralkyl, and the like,Or cyclic groups of carbon atoms with other atoms such as nitrogen, phosphorus, oxygen and sulfur.
The halogen-free flame retardant composition comprises aluminum oxide, calcium oxide, magnesium oxide, ferrous oxide, ferric oxide, zinc oxide, titanium oxide, antimony oxide, zirconium oxide, bismuth trioxide, gallium oxide, lanthanum oxide, and vanadium oxide (VO, V) 2 O 3 、VO 2 、V 2 O 5 ) The metal hydroxide is one or more of aluminum hydroxide, calcium hydroxide, magnesium hydroxide, ferrous hydroxide, ferric hydroxide, zinc hydroxide, titanium hydroxide, antimony hydroxide, zirconium hydroxide, tin hydroxide and barium hydroxide.
The halogen-free flame retardant composition, wherein the organic amine is more than one of melamine, piperazine, dicyandiamide, guanidine, ethylenediamine, diethylenetriamine, triethylenetetramine, propylenediamine, cyclohexanediamine, morpholine, ethanolamine, melam, melem, cytosine, uracil, guanosine and adenine.
The organic phosphonate is obtained by reacting one of the organic phosphonic acid, one of the metal oxide and/or the metal hydroxide and one of the organic amine, and the halogen-free flame retardant composition of the invention can be provided with only one organic phosphonate or can comprise a plurality of organic phosphonates at the same time.
The halogen-free flame retardant composition comprises more than one of zinc cyanurate, calcium cyanurate, magnesium cyanurate, stannous cyanurate, tin cyanurate, ferrous cyanurate, ferric cyanurate, titanium cyanurate and aluminum cyanurate.
A halogen-free flame retardant composition as described above wherein the hypophosphite is aluminum hypophosphite, calcium hypophosphite, lithium hypophosphite, potassium hypophosphite, magnesium hypophosphite, nickel hypophosphite, melamine hypophosphite, aluminum diethyl hypophosphite, aluminum methylethyl hypophosphite, aluminum methylpropyl hypophosphite, zinc diethyl hypophosphite or magnesium diethyl hypophosphite.
A halogen-free flame retardant composition as described above, the halogen-free flame retardant composition further comprising other components;
other components are other flame retardants and/or adjuvants, such as phosphate flame retardants, ammonium polyphosphate, metal hydrates, zinc oxide, titanium oxide, aluminum oxide, magnesium hydroxide, hydrotalcite, talc, wollastonite powder, silicone powder, and melamine cyanurate, pentaerythritol, dipentaerythritol, tripentaerythritol, THEIC and TGIC, anti-drip agents polytetrafluoroethylene, polysiloxanes.
In one halogen-free flame retardant composition as described above, the other components are added in an amount of 0.5 to 5wt% based on the total amount of the halogen-free flame retardant composition.
The invention also provides a preparation method of the halogen-free flame retardant composition, which is characterized in that organic phosphonate, cyanuric acid and/or metal cyanurate and hypophosphite are mixed uniformly or the organic phosphonate, the cyanuric acid and/or the metal cyanurate, the hypophosphite and other components are mixed uniformly in proportion to obtain the halogen-free flame retardant composition.
The invention further provides application of the halogen-free flame retardant composition, wherein the halogen-free flame retardant composition is added into a polymer or a flammable material needing to obtain flame retardance, and the flame retardant polymer or the flame retardant material is obtained.
The mechanism of the invention is as follows:
in the initial stage of combustion of the flame-retardant polymer, the organic groups of the organic phosphonate can form innumerable microreactors on a surface layer compatible with the polymer, wherein molecular self-assembly reaction can be carried out between the organic phosphonic acid, the metal oxide or the hydroxide and the organic amine to generate a network structure containing P-O-N, P-O-M bonds with a special structure, further chemical reaction of carbon generation and micro-foaming is generated, the reaction model is shown in figure 1, in particular to the induction effect of metal ions, so that the electrophilicity of phosphorus is effectively improved, and the catalytic carbon generation effect is enhanced; meanwhile, the cyanuric acid group has good reactivity with organic amine, and a graphite-like triazine ring-containing structural system with a honeycomb structure is rapidly generated, so that the heat insulation and mass transfer blocking effects are good; in addition, the hypophosphite has stronger reducibility, oxygen in the air and oxygen-containing free radicals generated in the early stage of thermal oxygen degradation of the polymer can be quenched in a cooperation way at the periphery of the microreactor in a certain temperature area, as shown in a reaction model shown in figure 1, so that the progress of a combustion free radical chain reaction is effectively prevented, the flame retardant efficiency is effectively improved, and the char formation-micro foaming effect in the microreactor and the effect of the reduction quenching free radicals of the hypophosphite are mutually cooperated in the flame retardant system of the invention. Especially, the existence of organic groups in the molecular structure can effectively prevent agglomeration among flame retardant powder, improve the dispersibility and moisture resistance of the flame retardant in the flame retardant material, and improve the physical and flame retardant properties. Meanwhile, the flame retardance of the flame retardant composition is realized through countless microreactors, and the flame retardance is uniformly distributed in the flame retardant material, so that the flame retardance is more stable; in addition, the stability of the flame retardant property of the flame retardant material in a humid environment is ensured due to the improvement of the moisture resistance. The flame retardant composition has the advantages of easily available raw materials, simple and easy process, and good market application prospect.
The beneficial effects are that:
(1) The preparation method of the halogen-free flame retardant composition has the advantages of easily available raw materials, simple and easy process and easy realization of industrialization;
(2) According to the halogen-free flame retardant composition, the organic phosphonate and cyanuric acid or salt in the components form a flame retardant microreactor in the initial combustion stage, so that the catalytic carbonization effect is enhanced, and the efficient flame retardant effect is achieved;
(3) The halogen-free flame retardant composition disclosed by the application has the advantages of high flame retardant efficiency, good mechanical property and flame retardant property and wide application range.
Drawings
FIG. 1 is a schematic illustration of a flame retardant composition microreactor char forming foaming flame retardant model.
Detailed Description
The application is further described below in conjunction with the detailed description. It is to be understood that these examples are illustrative of the present application and are not intended to limit the scope of the present application. Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the teachings of the present application, and such equivalents are intended to fall within the scope of the application as defined in the appended claims.
In the application, referring to the hygroscopicity evaluation method reported in Chinese patent ZL200580005684.3, a flame-retardant polymer material and a blank material without flame retardant are respectively manufactured into a material with the same thickness (such as a sheet with the thickness of 1 mm), the weight gain condition is tested after the material is placed for 14 days in an environment with the relative humidity of 100% at 70 ℃, the difference of the weight increase percentage of the flame-retardant polymer material minus the weight increase percentage of the blank material without flame retardant is recorded as the weight gain rate of the flame-retardant polymer material, and the hygroscopicity is evaluated according to the size of the weight gain rate (the smaller the weight gain rate is, the smaller the hygroscopicity is).
Example 1
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing phytic acid in proper water and fully stirring for 0.5h;
(2) Mixing zinc oxide and melamine to obtain a mixture, continuously adding the mixture into the system in the step (1), after the mixture is added in 1 hour, gradually heating to 90 ℃, and maintaining stirring for 5 hours;
wherein, the mol ratio of the phytic acid to the melamine to the zinc oxide is 0.1:1:0.1; the water consumption in the step (1) is as follows: 2000mL of water is added to each 100g of total amount of phytic acid, zinc oxide and melamine;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 2
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing phenylphosphonic acid in proper ethanol and fully stirring for 4 hours;
(2) Adding a mixture of aluminum hydroxide and ferric hydroxide and piperazine into the system in the step (1) for 5 times respectively, wherein the interval time is the same each time, the addition amount is the same each time, the addition is completed within 5 hours, the temperature is gradually increased to 40 ℃, and stirring is maintained for 6 hours;
wherein, in the mixture of the aluminum hydroxide and the ferric hydroxide, the molar ratio of the aluminum hydroxide to the ferric hydroxide is 2:3; the molar ratio of the phenylphosphonic acid, the piperazine to the mixture of the aluminum hydroxide and the ferric hydroxide is 16:1:5; the ethanol dosage in the step (1) is as follows: adding 100mL of ethanol to 100g of the total amount of the mixture of phenylphosphonic acid, aluminum hydroxide and ferric hydroxide and piperazine;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 3
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing 2-carboxyethyl methyl phosphinic acid in proper n-propanol and fully stirring for 1h;
(2) Continuously adding a mixture of titanium dioxide and magnesium hydroxide and dicyandiamide into the system in the step (1) respectively, after finishing adding in 2 hours, gradually heating to 50 ℃, and maintaining stirring for 10 hours;
wherein, in the mixture of titanium dioxide and magnesium hydroxide, the mol ratio of the titanium dioxide to the magnesium hydroxide is 1:3; the molar ratio of the 2-carboxyethyl methyl phosphinic acid, dicyandiamide to the mixture of titanium dioxide and magnesium hydroxide is 11:1:4; the dosage of the n-propanol in the step (1) is as follows: 1900mL of n-propanol are added per 100g of the total amount of dicyandiamide and the mixture of 2-carboxyethyl methyl phosphinic acid, titanium dioxide and magnesium hydroxide;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 4
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing the amino trimethylene phosphonic acid in the appropriate isobutanol and stirring thoroughly for 1.5h;
(2) Adding a mixture of zirconium oxide and antimony trioxide and cyclohexanediamine into the system in the step (1) for 6 times respectively, wherein the interval time is the same each time, the adding amount is the same each time, the adding is completed within 6 hours, the temperature is gradually increased to 100 ℃, and stirring is maintained for 8 hours;
wherein, in the mixture of zirconia and antimonous oxide, the mol ratio of the zirconia to the antimonous oxide is 2:1; the molar ratio of the mixture of aminotrimethylene phosphonic acid, cyclohexanediamine, zirconia and antimony trioxide is 6.4:1:1.5; the dosage of the isobutanol in the step (1) is as follows: 1800mL of isobutanol was added per 100g of the total amount of the mixture of aminotrimethylene phosphonic acid, zirconia and antimony trioxide and cyclohexanediamine;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 5
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing the hydroxyethylidene diphosphonic acid in proper acetone and fully stirring for 2.5h;
(2) Adding a mixture of morpholine, piperazine and ethanolamine and ferrous hydroxide into the system in the step (1) for 7 times respectively, wherein the interval time is the same each time, the adding amount is the same each time, the adding is completed within 6.5 hours, the temperature is gradually increased to 50 ℃, and stirring is maintained for 1 hour;
Wherein the molar ratio of morpholine, piperazine and ethanolamine in the mixture of morpholine, piperazine and ethanolamine is 1:5:4; the molar ratio of the hydroxyethylidene diphosphonic acid to the mixture of morpholine, piperazine and ethanolamine to the ferrous hydroxide is 1:1:0.5; the dosage of the acetone in the step (1) is as follows: 1600mL of acetone is added to 100g of the total amount of the mixture of the hydroxyethylidene diphosphonic acid, the ferrous hydroxide, the morpholine, the piperazine and the ethanolamine;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 6
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) The phosphonoglycolic acid is dispersed in the appropriate DMF and stirred thoroughly for 3h;
(2) Adding vanadium pentoxide and dicyandiamide into the system in the step (1) for 10 times respectively, wherein the interval time is the same each time, the adding amount is the same each time, the adding is completed within 10 hours, the temperature is gradually increased to 100 ℃, and stirring is maintained for 5 hours;
wherein the molar ratio of the phosphonic glycolic acid to the dicyandiamide to the vanadium pentoxide is 4:1:0.4; the DMF usage in step (1) is as follows: 1000mL of DMF is added per 100g of total amount of phosphonic glycolic acid, vanadium pentoxide and dicyandiamide;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 7
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Diethylenetriamine pentamethylenephosphonic acid was dispersed in an appropriate acetone/cyclohexanone mixture (V/v=1:1) and stirred thoroughly for 3.5h;
(2) Continuously adding a mixture of gallium oxide and aluminum hydroxide and melamine into the system in the step (1) respectively, after finishing adding in 2 hours, gradually heating to 40 ℃, and maintaining stirring for 6 hours;
wherein, in the mixture of gallium oxide and aluminum hydroxide, the molar ratio of gallium oxide to aluminum hydroxide is 1:30; the molar ratio of the mixture of diethylenetriamine pentamethylene phosphonic acid, melamine, gallium oxide and aluminum hydroxide is 5.3:1:3.1; the amount of acetone/cyclohexanone mixture in step (1) is: 900mL of the acetone/cyclohexanone mixture was added per 100g of the total amount of melamine and the mixture of diethylenetriamine pentamethylene phosphonic acid, gallium oxide and aluminum hydroxide;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
Example 8
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing the amino trimethylene phosphonic acid in proper water and fully stirring for 0.5h;
(2) Mixing zinc hydroxide and melam to obtain a mixture, adding the mixture into the system in the step (1) for 5 times, wherein the interval time is the same each time, the adding amount is the same each time, the adding is completed within 5 hours, and the temperature is gradually increased to 80 ℃ and stirring is maintained for 10 hours;
wherein, the mol ratio of the amino trimethylene phosphonic acid, the melam and the zinc hydroxide is 1.25:1:0.5; the water consumption in the step (1) is as follows: 800mL of water was added per 100g total of aminotrimethylene phosphonic acid, zinc hydroxide and melam;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 9
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing the hydroxyethylidene diphosphonic acid in proper n-butanol and fully stirring for 4 hours;
(2) Continuously adding a mixture of aluminum hydroxide and magnesium hydroxide and miller amine into the system in the step (1) respectively, finishing the addition within 1.5 hours, gradually heating to 50 ℃, and maintaining stirring for 8 hours;
Wherein, in the mixture of the aluminum hydroxide and the magnesium hydroxide, the molar ratio of the aluminum hydroxide to the magnesium hydroxide is 0.55:0.3; the molar ratio of hydroxyethylidene diphosphonic acid, melem to the mixture of aluminium hydroxide and magnesium hydroxide is 1.75:1:0.85; the dosage of n-butanol in the step (1) is as follows: 700mL of n-butanol was added per 100g of the total amount of the mixture of hydroxyethylidene diphosphonic acid, aluminum hydroxide, and magnesium hydroxide, and Millem;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 10
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing ethylenediamine tetramethylene phosphonic acid in proper acetone and fully stirring for 2.5h;
(2) Continuously adding a mixture of ferrous oxide, zinc oxide and aluminum hydroxide and melamine into the system in the step (1) respectively, finishing the addition within 2 hours, gradually heating to 70 ℃, and maintaining stirring for 3 hours;
wherein, in the mixture of ferrous oxide, zinc oxide and aluminum hydroxide, the molar ratio of the ferrous oxide, the zinc oxide and the aluminum hydroxide is 3:1:10; the molar ratio of ethylenediamine tetramethylene phosphonic acid, melamine to the mixture of ferrous oxide, zinc oxide and aluminum hydroxide is 1:1:1.4; the dosage of the acetone in the step (1) is as follows: 300mL of acetone was added per 100g of the total amount of the mixture of ethylenediamine tetramethylene phosphonic acid, melamine, and ferrous oxide, zinc oxide, and aluminum hydroxide;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
example 11
The preparation method of the organic phosphonic acid compound salt comprises the following specific steps:
(1) Dispersing the amino trimethylene phosphonic acid in proper acetone and fully stirring for 2.5h;
(2) Continuously adding a mixture of ferrous oxide, vanadium trioxide and aluminum hydroxide and guanidine into the system in the step (1) respectively, after finishing adding in 2 hours, gradually heating to 70 ℃, and maintaining stirring for 3 hours;
wherein, in the mixture of ferrous oxide, vanadium trioxide and aluminum hydroxide, the molar ratio of the ferrous oxide, the vanadium trioxide and the aluminum hydroxide is 0.2:0.25:2; the molar ratio of the amino trimethylene phosphonic acid, guanidine to the mixture of ferrous oxide, vanadium trioxide and aluminum hydroxide is 2:1.1:2.45; the dosage of the acetone in the step (1) is as follows: 1000mL of acetone was added per 100g total amount of the mixture of aminotrimethylene phosphonic acid, guanidine and ferrous oxide, zinc oxide and aluminum hydroxide;
(3) Filtering the precipitate obtained in the step (2), drying and crushing to obtain an organic phosphonic acid compound salt;
the molecular structure of the finally prepared organic phosphonic acid compound salt is as follows:
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Example 12
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, cyanuric acid and aluminum hypophosphite prepared in the example 1 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 90 parts of organic phosphonate, 9 parts of cyanuric acid and 1 part of aluminum hypophosphite.
And (3) carrying out melt blending on the prepared halogen-free flame retardant composition and polybutylene terephthalate (vinca 1100-211M), extruding and granulating to obtain the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 8wt%, the flame-retardant grade of the prepared flame-retardant polymer material is UL 94V 0, and the weight gain rate is 0.82wt%.
Example 13
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate prepared in the example 2, the mixture of cyanuric acid and zinc cyanurate in a mass ratio of 1:1, calcium hypophosphite and triphenylphosphine oxide according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 75 parts of organic phosphonate, 15 parts of a mixture of cyanuric acid and zinc cyanurate and 10 parts of calcium hypophosphite; triphenylphosphine oxide was added in an amount of 0.5wt% based on the total halogen-free flame retardant composition.
And (3) carrying out melt blending on the prepared halogen-free flame retardant composition and polyurethane (Lu Borun polyester TPU S392A) and extruding and granulating to obtain the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 15wt%, the flame-retardant grade of the prepared flame-retardant polymer material is UL 94V 0, and the weight gain rate is 0.95wt%.
Example 14
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, the calcium cyanurate, the nickel hypophosphite and the ammonium polyphosphate prepared in the embodiment 3 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 85 parts of organic phosphonate, 10 parts of calcium cyanurate and 5 parts of nickel hypophosphite; the ammonium polyphosphate was added in an amount of 5wt% based on the total amount of the halogen-free flame retardant composition.
And (3) melting and blending the prepared halogen-free flame retardant composition with nylon 6 (Yue Hua YH 800), extruding and granulating to obtain the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 6wt%, the flame-retardant grade of the prepared flame-retardant polymer material is UL 94V 0, and the weight gain rate is 0.92wt%.
Example 15
A preparation method of a halogen-free flame retardant composition comprises the following steps:
Uniformly mixing the organic phosphonate, the magnesium cyanurate, the lithium hypophosphite and the triphenyl phosphate prepared in the example 4 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 78 parts of organic phosphonate, 14 parts of magnesium cyanurate and 8 parts of lithium hypophosphite; the triphenyl phosphate was added in an amount of 1wt% based on the total amount of the halogen-free flame retardant composition.
The prepared halogen-free flame retardant composition is melt-blended with ABS (Qimei, brand 707) and then extruded and granulated to prepare the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 12wt%, the flame-retardant grade of the prepared flame-retardant polymer material is UL 94V 0, and the weight gain rate is 0.65wt%.
Example 16
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, stannous cyanurate, potassium hypophosphite and zinc oxide prepared in the example 5 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 80 parts of organic phosphonate, 10 parts of stannous cyanurate and 10 parts of potassium hypophosphite; the zinc oxide was added in an amount of 2wt% based on the total halogen-free flame retardant composition.
And (3) carrying out melt blending on the prepared halogen-free flame retardant composition and SBS resin (Kraton SBS D1116 AIM) and extruding and granulating to obtain the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 18wt%, and the flame-retardant grade of the prepared flame-retardant polymer material is UL 94V 0 and the weight gain rate is 0.6wt%.
Example 17
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, the tin cyanurate, the magnesium hypophosphite and the titanium oxide prepared in the example 6 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 88 parts of organic phosphonate, 9 parts of tin cyanurate and 3 parts of magnesium hypophosphite; the amount of titanium oxide added was 3wt% based on the total halogen-free flame retardant composition.
And (3) melting and blending the prepared halogen-free flame retardant composition with polylactic acid (marine organism REVODE 210), extruding and granulating to obtain the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 10wt%, and the flame-retardant grade of the prepared flame-retardant polymer material is UL94V0, and the weight gain rate is 0.89wt%.
Example 18
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate prepared in the example 7, ferrous cyanurate, methyl ethyl aluminum hypophosphite and dipentaerythritol according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 82 parts of organic phosphonate, 10 parts of ferrous cyanurate and 8 parts of methyl ethyl aluminum hypophosphite; dipentaerythritol is added in an amount of 4wt% based on the total amount of the halogen-free flame retardant composition.
The prepared halogen-free flame retardant composition and high-density polyethylene (China petrochemical trade name: 5000S) are melt blended and then extruded and granulated to prepare the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 20wt%, the flame-retardant grade of the prepared flame-retardant polymer material is UL94V0, and the weight gain rate is 0.35wt%.
Example 19
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, the ferric cyanurate, the melamine hypophosphite and the magnesium oxide prepared in the example 8 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 90 parts of organic phosphonate, 8.5 parts of ferric cyanurate and 1.5 parts of melamine hypophosphite; the amount of magnesium oxide added was 2wt% of the total halogen-free flame retardant composition.
The prepared halogen-free flame retardant composition and polypropylene (China petrochemical brand T30S) are melt-blended and then extruded and granulated to prepare the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 18wt%, the flame-retardant grade of the prepared flame-retardant polymer material is UL94V0, and the weight gain rate is 1.05wt%.
Example 20
A preparation method of a halogen-free flame retardant composition comprises the following steps:
Uniformly mixing the organic phosphonate, the titanium cyanurate, the diethyl aluminum hypophosphite and the magnesium hydroxide prepared in the example 9 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 76 parts of organic phosphonate, 15 parts of titanium cyanurate and 9 parts of diethyl aluminum hypophosphite; the magnesium hydroxide was added in an amount of 3wt% based on the total amount of the halogen-free flame retardant composition.
And (3) melting and blending the prepared halogen-free flame retardant composition with EVA (Tosoh 634 VA), extruding and granulating to obtain the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 16wt%, the flame-retardant grade of the prepared flame-retardant polymer material is UL 94V 0, and the weight gain rate is 0.88wt%.
Example 21
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate prepared in the example 10, aluminum cyanurate, zinc diethyl hypophosphite and hydrotalcite according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 84 parts of organic phosphonate, 11 parts of aluminum cyanurate and 5 parts of zinc diethyl hypophosphite; the hydrotalcite was added in an amount of 4wt% based on the total amount of the halogen-free flame retardant composition.
The prepared halogen-free flame retardant composition and 30% glass fiber reinforced nylon 66 (Shenma EPR 2701) are melt blended and then extruded and granulated to prepare the flame retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 15wt%, and the flame retardant grade of the prepared flame retardant polymer material is UL 94V 0 and the weight gain rate is 1.01wt%.
Example 22
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, cyanuric acid, aluminum hypophosphite and aluminum oxide prepared in the example 5 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 86 parts of organic phosphonate, 12 parts of cyanuric acid and 2 parts of aluminum hypophosphite; the amount of alumina added was 3wt% of the total halogen-free flame retardant composition.
The prepared halogen-free flame retardant composition is melt-blended with PC/ABS alloy (7:3, PC is SABIC LEXAN101, ABS is Qimei 757) and then extruded and granulated to prepare the flame-retardant polymer material, wherein the addition amount of the halogen-free flame retardant composition is 10.5wt%, the flame-retardant grade of the prepared flame-retardant polymer material is UL 94V 0, and the weight gain rate is 0.66wt%.
Example 23
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, cyanuric acid, magnesium hypophosphite and tripentaerythritol prepared in the example 11 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 85 parts of organic phosphonate, 9 parts of cyanuric acid and 6 parts of magnesium hypophosphite; tripentaerythritol is added in an amount of 3wt% based on the total halogen-free flame retardant composition.
Example 24
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, cyanuric acid, methyl ethyl aluminum hypophosphite and THEIC prepared in the example 4 in proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 83.1 parts of organic phosphonate, 13.5 parts of cyanuric acid and 3.4 parts of methyl ethyl aluminum hypophosphite; the THEIC was added in an amount of 4wt% based on the total halogen-free flame retardant composition.
Example 25
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, cyanuric acid, melamine hypophosphite and TGIC prepared in the example 3 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 80.5 parts of organic phosphonate, 10.5 parts of cyanuric acid and 8.5 parts of melamine hypophosphite; TGIC was added in an amount of 4wt% based on the total halogen-free flame retardant composition.
Example 26
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, cyanuric acid, diethyl aluminum hypophosphite and polytetrafluoroethylene prepared in the example 2 in proportion to obtain a halogen-free flame retardant composition;
Wherein the weight portions of the components are as follows: 83 parts of organic phosphonate, 12 parts of cyanuric acid and 5 parts of diethyl aluminum hypophosphite; the polytetrafluoroethylene was added in an amount of 5% by weight based on the total amount of the halogen-free flame retardant composition.
Example 27
A preparation method of a halogen-free flame retardant composition comprises the following steps:
uniformly mixing the organic phosphonate, cyanuric acid, zinc diethyl hypophosphite and polysiloxane (brand FCA-107) prepared in the example 1 according to a proportion to obtain a halogen-free flame retardant composition;
wherein the weight portions of the components are as follows: 85 parts of organic phosphonate, 10 parts of cyanuric acid and 5 parts of zinc diethyl hypophosphite; the polysiloxane was added in an amount of 5wt% of the total halogen-free flame retardant composition.
Example 28
A method of preparing a halogen-free flame retardant composition, the specific procedure being substantially as in example 27, except that the organophosphonate prepared in example 1 is replaced with the organophosphonate prepared in examples 1 and 2, and the ratio of the two organophosphonates is 1:1; and the polysiloxane is replaced with melamine cyanurate.
Claims (10)
1. The halogen-free flame retardant composition is characterized by comprising the following components in parts by weight:
75-90 parts of organic phosphonate;
9-15 parts of cyanuric acid and/or cyanuric acid metal salt;
1-10 parts of hypophosphite;
the molecular structure of the organic phosphonate consists of organic amine cations with the structure shown in the formula (I), metal ions with the structure shown in the formula (II) and organic phosphonic acid anions with the structure shown in the formula (III) or the formula (IV), and the total charge value of the anions is equal to the total charge value of the cations;
wherein m=1, 2 or 3; n=1, 2, 3, 4 or 5;0<p≤2，0<q<2, and p+q=2; 0<x≤2，0<y<2, and x+y=2; h=1, 2, 3, 4, 5, 6 or 7; r, R * And R' "are each independently selected from alkyl groups containing or not containing heteroatom substituents, containingOr an aromatic hydrocarbon group containing no heteroatom substituent, a cyclic group formed by a carbon atom and other atoms, or a cyclic group containing a heteroatom substituent; r 'and R' are each independently selected from one of H, alkyl and aryl groups or R 'and R' form a ring group in the same molecule; m is more than one metal element;
the organic phosphonate is prepared by putting organic phosphonic acid, metal oxide and/or metal hydroxide and organic amine into a reactor through self-assembly reaction;
the molar ratio of the organic amine to the metal oxide and/or the metal hydroxide is 1:0.1-5.0, the molar ratio of the organic amine to the sum of the molar amount of metal ions in the metal oxide and/or the metal hydroxide multiplied by the metal valence to the molar amount of the organic phosphonic acid is 1:1/v-1, and v is the total number of P-O-H units contained in one organic phosphonic acid molecule.
2. The halogen-free flame retardant composition of claim 1 wherein the organic phosphonic acid is phytic acid or has one or more of the general structures shown in (a), (B), (C), and (D):
in the formula (A), R 1 Is alkyl, aryl, aralkyl, and the like,Or a cyclic group formed by a carbon atom and other atoms, wherein R 3 Is hydrogen, alkyl or aryl, X is hydroxy, mercapto, carboxyl, nitro or sulfo;
in the formula (B), R 2 Is alkyl, aryl, pyridyl, piperidinyl, and the like,Or cyclic groups formed by carbon atoms and other atoms, R' 2 A cyclic group which is a hydroxyl group, an alkyl group, an aromatic hydrocarbon group, or a carbon atom and other atoms;
in the formula (C), R 4 And R is 5 Each independently selected from alkyl, aromatic hydrocarbon groups or cyclic groups formed by carbon atoms and other atoms; r is R 6 Is alkyl, aryl, aralkyl, and the like,Or a cyclic group formed by a carbon atom and other atoms;
in the formula (D), R 7 Is alkyl, aryl, aralkyl, and the like,Or cyclic groups formed by carbon atoms with other atoms.
3. The halogen-free flame retardant composition of claim 2 wherein the metal oxide is one or more of aluminum oxide, calcium oxide, magnesium oxide, ferrous oxide, ferric oxide, zinc oxide, titanium oxide, antimony oxide, zirconium oxide, bismuth trioxide, gallium oxide, lanthanum oxide, vanadium oxide, manganese monoxide, manganese dioxide, stannous oxide, tin oxide, and barium oxide and the metal hydroxide is one or more of aluminum hydroxide, calcium hydroxide, magnesium hydroxide, ferrous hydroxide, ferric hydroxide, zinc hydroxide, titanium hydroxide, antimony hydroxide, zirconium hydroxide, tin hydroxide, and barium hydroxide.
4. A halogen-free flame retardant composition according to claim 3 wherein the organic amine is one or more of melamine, piperazine, dicyandiamide, guanidine, ethylenediamine, diethylenetriamine, triethylenetetramine, propylenediamine, cyclohexanediamine, morpholine, ethanolamine, melam, melem, cytosine, uracil, guanosine and adenine.
5. The halogen-free flame retardant composition of claim 1 wherein the metal cyanurate salt is one or more of zinc cyanurate, calcium cyanurate, magnesium cyanurate, stannous cyanurate, tin cyanurate, ferrous cyanurate, ferric cyanurate, titanium cyanurate, and aluminum cyanurate.
6. A halogen-free flame retardant composition according to claim 1, wherein the hypophosphite is aluminum hypophosphite, calcium hypophosphite, lithium hypophosphite, potassium hypophosphite, magnesium hypophosphite, nickel hypophosphite, melamine hypophosphite, diethyl aluminum hypophosphite, methyl ethyl aluminum hypophosphite, methyl propyl aluminum hypophosphite, diethyl zinc hypophosphite or diethyl magnesium hypophosphite.
7. A halogen-free flame retardant composition according to claim 1, wherein the halogen-free flame retardant composition further comprises other components;
The other components are other flame retardants and/or adjuvants.
8. A halogen-free flame retardant composition according to claim 7, wherein the other components are added in an amount of 0.5 to 5wt% of the total halogen-free flame retardant composition.
9. A process for the preparation of a halogen-free flame retardant composition as claimed in any one of claims 1 to 8, characterized in that: and (3) uniformly mixing the organic phosphonate, the cyanuric acid and/or the metal cyanurate and the hypophosphite or further mixing the organic phosphonate, the cyanuric acid and/or the metal cyanurate, the hypophosphite and other components according to a proportion to obtain the halogen-free flame retardant composition.
10. Use of a halogen-free flame retardant composition according to any of claims 1 to 8, characterized in that: and adding the halogen-free flame retardant composition into a polymer or a flammable material which needs to obtain flame retardance, thus obtaining the flame retardant polymer or the flame retardant material.
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| WO2014003279A1 (en) * | 2012-06-27 | 2014-01-03 | 주식회사 두본 | Method for preparing melamine phosphate-based flame retardant |
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| CN113354867A (en) * | 2020-03-06 | 2021-09-07 | 南通诺为新材料科技有限公司 | Flame-retardant thermoplastic polyamide, flame retardant and application |
| WO2022110392A1 (en) * | 2020-11-26 | 2022-06-02 | 浙江旭森非卤消烟阻燃剂有限公司 | Halogen-free flame retardant having good flame retardancy and processibility, and flame-retardant resin composition |
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| US9752009B2 (en) * | 2015-01-26 | 2017-09-05 | Lanxess Solutions Us Inc. | Flame retardant polymer compositions comprising heat treated phosphorus compounds and melam |
| CN116023410A (en) * | 2018-12-20 | 2023-04-28 | 朗盛公司 | Process for the preparation of phosphorus-containing flame retardants and their use in polymer compositions |
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| WO2006090751A1 (en) * | 2005-02-23 | 2006-08-31 | Polyplastics Co., Ltd. | Flame retardant resin composition |
| WO2014003279A1 (en) * | 2012-06-27 | 2014-01-03 | 주식회사 두본 | Method for preparing melamine phosphate-based flame retardant |
| CN107075202A (en) * | 2014-09-18 | 2017-08-18 | 弗劳恩霍弗应用研究促进协会 | Organic epoxide imide salts are used as the purposes of fire retardant, flame-retardant plastic composition, its preparation method and molded parts, paint or coating |
| CN113354867A (en) * | 2020-03-06 | 2021-09-07 | 南通诺为新材料科技有限公司 | Flame-retardant thermoplastic polyamide, flame retardant and application |
| WO2022110392A1 (en) * | 2020-11-26 | 2022-06-02 | 浙江旭森非卤消烟阻燃剂有限公司 | Halogen-free flame retardant having good flame retardancy and processibility, and flame-retardant resin composition |
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