DK2890702T3 - Fremgangsmåde til fremstilling af phosphorholdige flammehæmmende midler. - Google Patents
Fremgangsmåde til fremstilling af phosphorholdige flammehæmmende midler. Download PDFInfo
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- DK2890702T3 DK2890702T3 DK13780050.4T DK13780050T DK2890702T3 DK 2890702 T3 DK2890702 T3 DK 2890702T3 DK 13780050 T DK13780050 T DK 13780050T DK 2890702 T3 DK2890702 T3 DK 2890702T3
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- Prior art keywords
- process according
- residues
- residue
- guanamine
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- 239000003063 flame retardant Substances 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 16
- 229910052698 phosphorus Inorganic materials 0.000 title description 12
- 239000011574 phosphorus Substances 0.000 title description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- -1 phosphoryl residues Chemical group 0.000 claims description 24
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229920000877 Melamine resin Polymers 0.000 claims description 14
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 13
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 5
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 235000013312 flour Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 7
- 238000007254 oxidation reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000004679 31P NMR spectroscopy Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000002516 radical scavenger Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- STCBHSHARMAIOM-UHFFFAOYSA-N 1-methyl-1h-imidazol-1-ium;chloride Chemical compound Cl.CN1C=CN=C1 STCBHSHARMAIOM-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QPQGTZMAQRXCJW-UHFFFAOYSA-N [chloro(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(Cl)C1=CC=CC=C1 QPQGTZMAQRXCJW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000007974 melamines Chemical class 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- UKDDQGWMHWQMBI-UHFFFAOYSA-O 1,2-diphytanoyl-sn-glycero-3-phosphocholine Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)CC(=O)OCC(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CC(C)CCCC(C)CCCC(C)CCCC(C)C UKDDQGWMHWQMBI-UHFFFAOYSA-O 0.000 description 1
- PSICBBXHZMXMGB-UHFFFAOYSA-N 2-n,4-n,6-n-tris(benzo[c][2,1]benzoxaphosphinin-6-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound O1C2=CC=CC=C2C2=CC=CC=C2P1NC1=NC(NP2C3=CC=CC=C3C3=CC=CC=C3O2)=NC(NP2C3=CC=CC=C3C3=CC=CC=C3O2)=N1 PSICBBXHZMXMGB-UHFFFAOYSA-N 0.000 description 1
- UBPQITZLYDWRFS-UHFFFAOYSA-N 3,4-dihydro-1H-triazine-2,4-diamine Chemical compound NC1NN(N)NC=C1 UBPQITZLYDWRFS-UHFFFAOYSA-N 0.000 description 1
- GCDRIRYINCSSIW-UHFFFAOYSA-N 6-chlorobenzo[c][2,1]benzoxaphosphinine 6-oxide Chemical compound C1=CC=C2P(Cl)(=O)OC3=CC=CC=C3C2=C1 GCDRIRYINCSSIW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 101100387911 Caenorhabditis elegans dop-2 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- VBQRUYIOTHNGOP-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinine 6-oxide Chemical compound C1=CC=C2P(=O)OC3=CC=CC=C3C2=C1 VBQRUYIOTHNGOP-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013462 industrial intermediate Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical class C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- WEWFIUPOLKEEJP-UHFFFAOYSA-N triazine-4,6-diamine Chemical class NC1=CC(N)=NN=N1 WEWFIUPOLKEEJP-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/66—Derivatives of melamine in which a hetero atom is directly attached to a nitrogen atom of melamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4476—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of aromatic amines (N-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6521—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657154—Cyclic esteramides of oxyacids of phosphorus
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Fireproofing Substances (AREA)
Claims (11)
1. Fremgangsmåde til fremstilling af forbindelser med følgende formel (I):
(I) hvor: resten R1 er udvalgt fra -NH2, -NH2-ZAZ såvel som monovalente alkyl- og arylrester, resterne A er hver udvalgt, uafhængigt af hinanden, fra følgende phosphorylrester DOPO-, DPhPO- og DPhOPO-:
indekserne x, y og z, uafhængigt af hinanden, repræsenterer hver 0 eller 1, hvor mindst ét af indekserne + 0; i hvilken, i et første trin, melamin eller, når R1 er en alkyl- eller arylrest, det tilsvarende alkyl- eller arylguanamin omsættes med et eller flere af følgende phosphinylchlorider D0P-C1, DPhP-Cl og DPhOP-Cl:
med henblik på at binde en eller flere phosphinylrester til aminogruppe(r) af melamin eller guanamin, hvorefter i et andet trin den bundne phosphi-nylrest(er) oxideres ved omsætning med et oxiderende middel for at danne tilsvarende phosphorylrest(er).
2. Fremgangsmåde ifølge krav 1 kendetegnet ved, at den monovalente alkyl- eller arylrest af R1 er udvalgt fra -CH3 og -C6H5.
3. Fremgangsmåde ifølge krav 1 eller krav 2 kendetegnet ved, at et peroxid er anvendt som det oxiderende middel.
4. Fremgangsmåde ifølge krav 3 kendetegnet ved, at hydro- genperoxidet eller t-butyl-hydroperoxid er anvendt som det oxiderende middel.
5. Fremgangsmåde ifølge et hvilket som helst af de foregå ende krav kendetegnet ved, at det første trin er udført i nærvær af en syrefjerner.
6. Fremgangsmåde ifølge krav 5 kendetegnet ved, at syre- fjerneren samtidigt fungerer som et opløsningsmiddel.
7. Fremgangsmåde ifølge krav 6 kendetegnet ved, at 1- methylimidazol er anvendt som syrefjerner og opløs ningsmiddel .
8. Fremgangsmåde ifølge et hvilket som helst af de foregå ende krav kendetegnet ved, at det andet trin udføres i et organisk opløsningsmiddel, der er udvalgt fra chlorform og toluen.
9. Fremgangsmåde ifølge et hvilket som helst af de foregå ende krav kendetegnet ved, at det første trin udføres ved en temperatur, der ligger i området 100 °C til 200 °C.
10. Fremgangsmåde ifølge et hvilket som helst af de foregå ende krav kendetegnet ved, at det andet trin udføres ved en temperatur, der ligger i området 50 °C til 100 °C. 11. 2,4,6-tris(9,10-dihydro-9-oxa-10-oxo-10- phosphaphenanthren-10-ylamino)-1,3,5-triazin (DOPO3- mel) :
hvor DOPO- svarer til rester
12. Anvendelse af 2,4,6-tris ( 9,10-dihydro-9-oxa-10-oxo-l0-phosphaphenanthren-10-ylamino)-1,3,5-triazin som et flammehæmmende middel.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ATA944/2012A AT513327B1 (de) | 2012-08-29 | 2012-08-29 | Verfahren zur Herstellung von phosphorhaltigen Verbindungen |
| PCT/AT2013/050167 WO2014032070A1 (de) | 2012-08-29 | 2013-08-28 | Verfahren zur herstellung von phosphorhaltigen flammschutzmitteln |
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| Publication Number | Publication Date |
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| DK2890702T3 true DK2890702T3 (da) | 2016-12-19 |
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| DK13780050.4T DK2890702T3 (da) | 2012-08-29 | 2013-08-28 | Fremgangsmåde til fremstilling af phosphorholdige flammehæmmende midler. |
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| US (1) | US9238777B2 (da) |
| EP (1) | EP2890702B1 (da) |
| JP (1) | JP2015530999A (da) |
| KR (1) | KR20150052138A (da) |
| AT (1) | AT513327B1 (da) |
| DK (1) | DK2890702T3 (da) |
| RU (1) | RU2639161C2 (da) |
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| CN106633052B (zh) * | 2015-11-04 | 2019-06-25 | 华中师范大学 | 磷杂菲-三嗪双官能团低聚物及其制备方法与阻燃应用 |
| CN105541917B (zh) * | 2016-01-27 | 2017-10-17 | 厦门大学 | 一种磷氮协同聚酯阻燃剂及其制备方法 |
| KR102054675B1 (ko) * | 2017-06-20 | 2019-12-11 | (주)엔나노텍 | 난연성 에스테르 폴리올 및 이의 제조방법과, 상기 난연성 에스테르 폴리올을 포함하여 제조되는 폴리이소시아누레이트 |
| TWI668228B (zh) * | 2018-05-21 | 2019-08-11 | 國立中興大學 | 磷系化合物、其製備方法與阻燃固化物 |
| CN110938235B (zh) * | 2019-11-13 | 2021-09-17 | 上海力道新材料科技股份有限公司 | 含三嗪结构dopo氨基衍生物阻燃剂及其制法和应用 |
| CN110982121B (zh) * | 2019-12-05 | 2021-09-28 | 营口理工学院 | 一种三嗪基磷氮系阻燃剂及其制备方法和应用 |
| KR102477271B1 (ko) * | 2020-12-18 | 2022-12-13 | 한국신발피혁연구원 | 고인성 및 난연성을 가지는 열경화성 수지 조성물 |
| CN113025248B (zh) * | 2021-03-17 | 2021-11-23 | 东莞市德聚胶接技术有限公司 | 一种热固环氧胶及其制备方法 |
| WO2023153508A1 (ja) * | 2022-02-14 | 2023-08-17 | 三光株式会社 | 高屈折率を示す、トリアジン環を有する新規なジヒドロオキサフォスファフェナントレン誘導体及びその製造方法 |
| CN115073522B (zh) * | 2022-07-20 | 2022-11-18 | 上海沪正纳米科技有限公司 | 基于dopo基团含硅磷氮的化合物及其制备方法和用途 |
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| JPH0812692A (ja) * | 1994-06-23 | 1996-01-16 | Asahi Chem Ind Co Ltd | 新規な含窒素有機燐化合物及びその製法 |
| TW593526B (en) | 2001-09-20 | 2004-06-21 | Wangsuen Su Jen | Phosphorus group containing flame retardant hardener, advanced epoxy resins and cured epoxy resins thereof |
| DE102004042833B4 (de) * | 2004-09-04 | 2022-01-05 | Chemische Fabrik Budenheim Kg | Polyphosphatderivat einer 1,3,5-Triazonverbindung, Verfahren zu dessen Herstellung und dessen Verwendung |
| JP2007196631A (ja) * | 2006-01-30 | 2007-08-09 | Adeka Corp | 感熱記録材料 |
| CN102190814B (zh) * | 2011-03-25 | 2012-11-21 | 武汉工程大学 | 六苯基磷酸酯三聚氰胺盐阻燃剂制备方法 |
| CN102190801B (zh) | 2011-03-29 | 2012-11-21 | 湖南科技大学 | 一种以单一乳化剂制备非离子型氧化聚乙烯蜡乳液的方法 |
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2012
- 2012-08-29 AT ATA944/2012A patent/AT513327B1/de not_active IP Right Cessation
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2013
- 2013-08-28 JP JP2015528803A patent/JP2015530999A/ja active Pending
- 2013-08-28 RU RU2015110993A patent/RU2639161C2/ru active
- 2013-08-28 KR KR1020157007873A patent/KR20150052138A/ko not_active Application Discontinuation
- 2013-08-28 EP EP13780050.4A patent/EP2890702B1/de not_active Not-in-force
- 2013-08-28 DK DK13780050.4T patent/DK2890702T3/da active
- 2013-08-28 WO PCT/AT2013/050167 patent/WO2014032070A1/de active Application Filing
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2890702B1 (de) | 2016-08-24 |
| US20150203759A1 (en) | 2015-07-23 |
| RU2015110993A (ru) | 2016-10-20 |
| JP2015530999A (ja) | 2015-10-29 |
| AT513327B1 (de) | 2014-06-15 |
| EP2890702A1 (de) | 2015-07-08 |
| AT513327A1 (de) | 2014-03-15 |
| KR20150052138A (ko) | 2015-05-13 |
| WO2014032070A1 (de) | 2014-03-06 |
| US9238777B2 (en) | 2016-01-19 |
| RU2639161C2 (ru) | 2017-12-20 |
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