DE2646218C3 - Phosphorhaltige Verbindungen, Verfahren zu deren Herstellung und Verwendung derselben zur Flammfestmachung - Google Patents
Phosphorhaltige Verbindungen, Verfahren zu deren Herstellung und Verwendung derselben zur FlammfestmachungInfo
- Publication number
- DE2646218C3 DE2646218C3 DE2646218A DE2646218A DE2646218C3 DE 2646218 C3 DE2646218 C3 DE 2646218C3 DE 2646218 A DE2646218 A DE 2646218A DE 2646218 A DE2646218 A DE 2646218A DE 2646218 C3 DE2646218 C3 DE 2646218C3
- Authority
- DE
- Germany
- Prior art keywords
- phosphorus
- acid
- reaction
- flame
- parts
- 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.)
- Expired
Links
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 67
- 239000011574 phosphorus Substances 0.000 title claims description 64
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 51
- 150000001875 compounds Chemical class 0.000 title claims description 44
- 238000004519 manufacturing process Methods 0.000 title description 32
- 238000000034 method Methods 0.000 title description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 66
- 229920000728 polyester Polymers 0.000 description 47
- 239000003063 flame retardant Substances 0.000 description 46
- 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 description 34
- 238000006243 chemical reaction Methods 0.000 description 33
- -1 triphenyl phosphate Chemical class 0.000 description 26
- 229920000642 polymer Polymers 0.000 description 25
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 22
- 239000007788 liquid Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 238000005809 transesterification reaction Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 12
- 150000002009 diols Chemical class 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 239000000835 fiber Substances 0.000 description 10
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 10
- 150000003018 phosphorus compounds Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- 230000032050 esterification Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
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- 238000000862 absorption spectrum Methods 0.000 description 6
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- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
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- 239000004246 zinc acetate Substances 0.000 description 5
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- 125000005843 halogen group Chemical group 0.000 description 4
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- 239000011701 zinc Substances 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GKMXREIWPASRMP-UHFFFAOYSA-J dipotassium;oxalate;oxygen(2-);titanium(4+) Chemical compound [O-2].[K+].[K+].[Ti+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O GKMXREIWPASRMP-UHFFFAOYSA-J 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- 238000001879 gelation Methods 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 229920006158 high molecular weight polymer Polymers 0.000 description 3
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- 150000002739 metals Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
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- 230000003247 decreasing effect Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- ITMIAZBRRZANGB-UHFFFAOYSA-N but-3-ene-1,2-diol Chemical compound OCC(O)C=C ITMIAZBRRZANGB-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- MRSOZKFBMQILFT-UHFFFAOYSA-L diazanium;oxalate;titanium(2+) Chemical compound [NH4+].[NH4+].[Ti+2].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O MRSOZKFBMQILFT-UHFFFAOYSA-L 0.000 description 1
- VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012757 flame retardant agent Substances 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 description 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- YXTFRJVQOWZDPP-UHFFFAOYSA-M sodium;3,5-dicarboxybenzenesulfonate Chemical compound [Na+].OC(=O)C1=CC(C(O)=O)=CC(S([O-])(=O)=O)=C1 YXTFRJVQOWZDPP-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
- C07F9/657163—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 the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—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 the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12416475A JPS5247891A (en) | 1975-10-14 | 1975-10-14 | Phosphorus-containing flame retarders |
| JP51006924A JPS582240B2 (ja) | 1976-01-23 | 1976-01-23 | 新規含リン化合物 |
| JP1508876A JPS5298395A (en) | 1976-02-13 | 1976-02-13 | Phosphorus-containing incombustible agent |
| JP1509076A JPS5922717B2 (ja) | 1976-02-13 | 1976-02-13 | 新規な有機リン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2646218A1 DE2646218A1 (de) | 1977-04-28 |
| DE2646218B2 DE2646218B2 (de) | 1980-01-10 |
| DE2646218C3 true DE2646218C3 (de) | 1980-10-16 |
Family
ID=27454598
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2646218A Expired DE2646218C3 (de) | 1975-10-14 | 1976-10-13 | Phosphorhaltige Verbindungen, Verfahren zu deren Herstellung und Verwendung derselben zur Flammfestmachung |
| DE2660334A Expired DE2660334C2 (de) | 1975-10-14 | 1976-10-13 | Verwendung von bestimmten Phosphor enthaltenden Verbindungen zum Flammfestmachen von Polyestern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2660334A Expired DE2660334C2 (de) | 1975-10-14 | 1976-10-13 | Verwendung von bestimmten Phosphor enthaltenden Verbindungen zum Flammfestmachen von Polyestern |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4127590A (OSRAM) |
| CA (1) | CA1077499A (OSRAM) |
| DE (2) | DE2646218C3 (OSRAM) |
| FR (1) | FR2327996A1 (OSRAM) |
| GB (1) | GB1534092A (OSRAM) |
| IT (1) | IT1078706B (OSRAM) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0212622A3 (en) * | 1985-08-29 | 1988-02-17 | Teijin Limited | Flameproofing synthetic fiber |
| EP0648809A1 (de) * | 1993-10-09 | 1995-04-19 | Hoechst Aktiengesellschaft | Pillarme und schwer entflammbare Mischungen aus einem Phosphor und einem Silizium enthaltenden Polyester |
| EP0640638A3 (de) * | 1993-08-27 | 1995-06-07 | Hoechst Ag | Pillarm und schwer entflammbar modifizierte Polyester, Verfahren zu ihrer Herstellung und daraus geformte Gebilde. |
| US8389901B1 (en) | 2010-05-27 | 2013-03-05 | Awds Technologies Srl | Welding wire guiding liner |
| US8674263B2 (en) | 2009-07-20 | 2014-03-18 | Awds Technologies Srl | Wire guiding liner, in particular a welding wire liner, with biasing means between articulated guiding bodies |
| US8882018B2 (en) | 2011-12-19 | 2014-11-11 | Sidergas Spa | Retainer for welding wire container and welding wire container with retainer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53128195A (en) * | 1977-04-15 | 1978-11-08 | Sanko Kaihatsu Kagaku Kenkiyuu | Flame retarder |
| JPS5912693B2 (ja) * | 1978-05-24 | 1984-03-24 | 株式会社三光開発科学研究所 | 難燃剤 |
| IT1130965B (it) * | 1979-03-19 | 1986-06-18 | Sanko Kaihatsu Kagaku Kenk | Agente ritardanti di fiamma |
| JPS60126293A (ja) * | 1983-12-09 | 1985-07-05 | Sanko Kaihatsu Kagaku Kenkyusho:Kk | 環状有機りん化合物及びその製造方法 |
| DE4402710A1 (de) * | 1994-01-29 | 1995-08-03 | Hoechst Ag | Verfahren zur Herstellung phosphorhaltiger Dicarbonsäurealkylester und Dicarbonsäuren |
| DE4436079A1 (de) | 1994-10-10 | 1996-04-11 | Hoechst Ag | Verfahren zur Herstellung phosphorhaltiger Dicarbonsäuren |
| US5530088A (en) * | 1995-06-21 | 1996-06-25 | Industrial Technology Research Institute | Heat resistant phosphorus-containing polymeric flame retardant and process for preparing the same |
| DE19613064C2 (de) * | 1996-04-01 | 1998-12-17 | Clariant Gmbh | Phosphormodifizierte Epoxidharzmischungen aus Epoxidharzen, phosphorhaltigen Verbindungen und einem Härter, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19613063C2 (de) * | 1996-04-01 | 1998-09-17 | Clariant Gmbh | Phosphormodifizierte Epoxidharze und ein Verfahren zu ihrer Herstellung |
| DE19619095A1 (de) | 1996-05-06 | 1997-11-13 | Schill & Seilacher | Flammfeste Epoxidharze und Flammschutzmittel für Epoxidharze |
| DE19711523C2 (de) * | 1997-03-19 | 2000-06-29 | Schill & Seilacher | Verfahren zur Herstellung eines DOP-ITS-Addukts und dessen Verwendung |
| DE19933932B4 (de) * | 1999-07-20 | 2006-06-14 | Schill + Seilacher Ag | Verfahren zur Herstellung von DOP und danach hergestelltes DOP mit reduziertem OPP-Gehalt |
| US6245880B1 (en) * | 1999-10-08 | 2001-06-12 | Toyo Boseki Kabushiki Kaisha | Organophosphorous composition, method of producing organophosphorous compound, polyester composition and method of producing the same |
| EP1101785A1 (de) * | 1999-11-15 | 2001-05-23 | Alcatel | Hohl- oder Bündelader |
| WO2002042374A1 (en) * | 2000-11-27 | 2002-05-30 | Kolon Industries Inc. | Flame retardant polybutyleneterephthalate resin |
| JP3926328B2 (ja) * | 2001-07-19 | 2007-06-06 | 株式会社カネカ | 人工毛髪 |
| US7186784B2 (en) * | 2001-09-20 | 2007-03-06 | Nof Corporation | Phosphorus-containing carboxylic acid derivatives process for preparations thereof and flame retardant |
| DE10203969C1 (de) * | 2002-01-31 | 2003-10-02 | Thueringisches Inst Textil | Verfahren zur Herstellung mehrfach DOPO-haltiger organischer Verbindungen und ihre Verwendung |
| US20050245647A1 (en) * | 2002-02-22 | 2005-11-03 | Kaneka Corporation | Flame-retardant polyester fiber and artificial hair comprising the same |
| WO2004113355A1 (de) | 2003-06-18 | 2004-12-29 | Thüringisches Institut für Textil- und Kunststoff-Forschung e.V. | Verfahren zur herstellung mehrfach dopo-haltiger organischer verbindungen und ihre verwendung |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3577381A (en) | 1968-04-25 | 1971-05-04 | Fmc Corp | Heat stabilization of polyester resin with phenylphosphinic acids |
| US3594347A (en) | 1968-09-05 | 1971-07-20 | Allied Chem | Polyesters containing aryl phosphinates |
| US3676393A (en) | 1968-10-14 | 1972-07-11 | Goodyear Tire & Rubber | Polyesters stabilized by phosphorus compounds |
| US3702878A (en) | 1969-12-31 | 1972-11-14 | Sanko Chemical Co Ltd | Cyclic organophosphorus compounds and process for making same |
-
1976
- 1976-10-07 US US05/730,512 patent/US4127590A/en not_active Expired - Lifetime
- 1976-10-13 DE DE2646218A patent/DE2646218C3/de not_active Expired
- 1976-10-13 IT IT69470/76A patent/IT1078706B/it active
- 1976-10-13 DE DE2660334A patent/DE2660334C2/de not_active Expired
- 1976-10-13 FR FR7630829A patent/FR2327996A1/fr active Granted
- 1976-10-14 GB GB42791/76A patent/GB1534092A/en not_active Expired
- 1976-10-14 CA CA263,391A patent/CA1077499A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3577381A (en) | 1968-04-25 | 1971-05-04 | Fmc Corp | Heat stabilization of polyester resin with phenylphosphinic acids |
| US3594347A (en) | 1968-09-05 | 1971-07-20 | Allied Chem | Polyesters containing aryl phosphinates |
| US3676393A (en) | 1968-10-14 | 1972-07-11 | Goodyear Tire & Rubber | Polyesters stabilized by phosphorus compounds |
| US3702878A (en) | 1969-12-31 | 1972-11-14 | Sanko Chemical Co Ltd | Cyclic organophosphorus compounds and process for making same |
Non-Patent Citations (2)
| Title |
|---|
| Referat der JP 4 315-74 im Hochmolekularbericht 1975 |
| Referat der JP 6174-73 im Hochmolekularbericht 1974 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0212622A3 (en) * | 1985-08-29 | 1988-02-17 | Teijin Limited | Flameproofing synthetic fiber |
| EP0640638A3 (de) * | 1993-08-27 | 1995-06-07 | Hoechst Ag | Pillarm und schwer entflammbar modifizierte Polyester, Verfahren zu ihrer Herstellung und daraus geformte Gebilde. |
| EP0648809A1 (de) * | 1993-10-09 | 1995-04-19 | Hoechst Aktiengesellschaft | Pillarme und schwer entflammbare Mischungen aus einem Phosphor und einem Silizium enthaltenden Polyester |
| US8674263B2 (en) | 2009-07-20 | 2014-03-18 | Awds Technologies Srl | Wire guiding liner, in particular a welding wire liner, with biasing means between articulated guiding bodies |
| US8389901B1 (en) | 2010-05-27 | 2013-03-05 | Awds Technologies Srl | Welding wire guiding liner |
| US8882018B2 (en) | 2011-12-19 | 2014-11-11 | Sidergas Spa | Retainer for welding wire container and welding wire container with retainer |
Also Published As
| Publication number | Publication date |
|---|---|
| US4127590A (en) | 1978-11-28 |
| FR2327996A1 (fr) | 1977-05-13 |
| CA1077499A (en) | 1980-05-13 |
| DE2646218A1 (de) | 1977-04-28 |
| IT1078706B (it) | 1985-05-08 |
| GB1534092A (en) | 1978-11-29 |
| DE2646218B2 (de) | 1980-01-10 |
| FR2327996B1 (OSRAM) | 1981-07-24 |
| DE2660334C2 (de) | 1986-10-16 |
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