DE1259338B - Verfahren zur Herstellung von Phosphonaten - Google Patents
Verfahren zur Herstellung von PhosphonatenInfo
- Publication number
- DE1259338B DE1259338B DEP30370A DEP0030370A DE1259338B DE 1259338 B DE1259338 B DE 1259338B DE P30370 A DEP30370 A DE P30370A DE P0030370 A DEP0030370 A DE P0030370A DE 1259338 B DE1259338 B DE 1259338B
- Authority
- DE
- Germany
- Prior art keywords
- tris
- phosphite
- phosphonate
- glycol
- phosphonates
- 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.)
- Pending
Links
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000007983 Tris buffer Substances 0.000 claims description 17
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 240000003628 Lardizabala biternata Species 0.000 claims 1
- 229920000180 alkyd Polymers 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000002903 organophosphorus compounds Chemical class 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 239000006260 foam Substances 0.000 description 11
- -1 polyethylene Polymers 0.000 description 11
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 8
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000003063 flame retardant Substances 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- 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 4
- CCJKFLLIJCGHMO-UHFFFAOYSA-N 2-[diethoxyphosphorylmethyl(2-hydroxyethyl)amino]ethanol Chemical compound CCOP(=O)(OCC)CN(CCO)CCO CCJKFLLIJCGHMO-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical compound [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000011496 polyurethane foam Substances 0.000 description 3
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSJIDMXMCQYKEW-UHFFFAOYSA-N P(O)(O)=O.OCCCOCCC.CC(COC(C)CO)O Chemical compound P(O)(O)=O.OCCCOCCC.CC(COC(C)CO)O CSJIDMXMCQYKEW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- BJXXCOMGRRCAGN-CLFAGFIQSA-N [2,2-bis(hydroxymethyl)-3-[(z)-octadec-9-enoyl]oxypropyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(CO)(CO)COC(=O)CCCCCCC\C=C/CCCCCCCC BJXXCOMGRRCAGN-CLFAGFIQSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- TYKFFKQSDMJPBS-UHFFFAOYSA-N hexane-1,2,6-triol;2-methyloxirane Chemical compound CC1CO1.OCCCCC(O)CO TYKFFKQSDMJPBS-UHFFFAOYSA-N 0.000 description 2
- 150000004000 hexols Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- UXTISIJVABJRGZ-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl.CC(O)CCl UXTISIJVABJRGZ-UHFFFAOYSA-N 0.000 description 1
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- BOKRKKCPFKUCIZ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;2-methyloxirane Chemical compound CC1CO1.OCC(CO)(CO)CO BOKRKKCPFKUCIZ-UHFFFAOYSA-N 0.000 description 1
- QABUQFYJORNZBW-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;phosphorous acid Chemical compound OP(O)O.CC(O)COC(C)CO QABUQFYJORNZBW-UHFFFAOYSA-N 0.000 description 1
- ZKVBYWIXODLPIB-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol;phosphorous acid Chemical compound OP(O)O.CC(O)COC(C)COC(C)CO ZKVBYWIXODLPIB-UHFFFAOYSA-N 0.000 description 1
- ANHAEBWRQNIPEV-UHFFFAOYSA-N 2-chloroethyl dihydrogen phosphate Chemical compound OP(O)(=O)OCCCl ANHAEBWRQNIPEV-UHFFFAOYSA-N 0.000 description 1
- BJUPZVQSAAGZJL-UHFFFAOYSA-N 2-methyloxirane;propane-1,2,3-triol Chemical compound CC1CO1.OCC(O)CO BJUPZVQSAAGZJL-UHFFFAOYSA-N 0.000 description 1
- SAWRKIBKAKPLFS-UHFFFAOYSA-N 3-(3-chloropropoxy)propan-1-ol Chemical compound OCCCOCCCCl SAWRKIBKAKPLFS-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DCFONRSFSKRGBI-UHFFFAOYSA-N CC(C)O.CC(O)COC(C)CO Chemical compound CC(C)O.CC(O)COC(C)CO DCFONRSFSKRGBI-UHFFFAOYSA-N 0.000 description 1
- OCLUUUROQDRUIU-UHFFFAOYSA-N CCCCCCCCCOP(O)=O Chemical compound CCCCCCCCCOP(O)=O OCLUUUROQDRUIU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- OXYMMMUMVUNYHF-UHFFFAOYSA-N OP(O)=O.CC(O)COC(C)CO Chemical compound OP(O)=O.CC(O)COC(C)CO OXYMMMUMVUNYHF-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical group CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 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 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/48—Lubricating compositions characterised by the base-material being a macromolecular compound containing phosphorus
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/093—Polyol derivatives esterified at least twice by phosphoric acid groups
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/1411—Esters of phosphorous acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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)]
- C07F9/40—Esters 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives 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
- C07F9/547—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
- C07F9/657109—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 esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
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- 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
- C07F9/657181—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, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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- C—CHEMISTRY; METALLURGY
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- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Description
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Int. Cl.:
C07f
Nummer: 1 259 338
Aktenzeichen: P 30370IV b/12 ο
Anmeldetag: 16. Oktober 1962
Auslegetag: 25. Januar 1968
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung neuer Phosphonate.
Die Verbindungen, welche nach der Erfindung hergestellt werden und die freie Hydroxylgruppen
haben, sind besonders wertvoll als Reaktionspartner für Polyisocyanate, ζ. B. Toluoldiisocyanat, um geschäumte
Polyurethane oder um Polyurethanelastomere herzustellen, die flammenfest sind und gute
Färbeigenschaften besitzen. Sie sind als antistatische Agentien für Polyäthylen und Polypropylen und als
Farbakzeptoren von besonderem Interesse, wenn sie Polyurethan-, Polyäthylen-, Epoxy- oder Polypropylenharzen
beigemischt werden. Sie können auch zum Flammenfestmachen von Polyestern verwendet
werden, indem man sie mit den Polysäuren, z. B. Terephthalsäure, Phthalsäure und Adipinsäure umsetzt.
Derartige Polyester lassen sich als Beschichtungsmittel für Holz oder Metall verwenden. Polyurethane
können als Beschichtungsmittel für Textilien, z. B. Mäntel, Anzüge und Kleider, als auch für
Isolationen in Gebäuden, Teppichunterlagen, Fäden, Becher und Schutzüberzüge für Stahl, Holz und Glas
verwendet werden.
Die erfindungsgemäß herstellbaren Phosphonate sind ebenfalls als Mittel zum Flammenfestmachen von
Zellulose und Zelluloseestern geeignet, während die hydroxylhaltigen Phosphonate als Reaktionspartner
für die Herstellung von Epoxyharzen verwendet werden können.
Die Erfindung betrifft die Herstellung von Phosphonaten und ist dadurch gekennzeichnet, daß man
ein Tris-(polypropylenglykol)-phosphit mit einer oder mehreren Phosphitgruppierungen in an sich bekannter
Weise a) mit einer katalytischen Menge oder b) mit einem Überschuß eines Alkylhalogenids bei erhöhter
Temperatur umsetzt.
Wenn ein Tris-(polypropylenglykol)-phosphit mit einer katalytischen Menge eines Alkylchlorids oder
-bromids bei erhöhter Temperatur behandelt wird, z. B. mit 5 Molprozent n-Butylbromid, erhält man
einen Bispolypropylenglykolester einer Hydroxyalkanätherphosphorsäure. Wenn die gleiche Reaktion
mit einem Überschuß an Alkylchlorid oder -bromid durchgeführt wird, ist das erhaltene Produkt
ein Bispolyalkylenglykolester einer Alkanphosphonsäure.
Die erfindungsgemäß hergestellten Produkte wurden in Vergleichsversuchen mit dem unter dem
Handelsnamen bekannten Fyrol
[(HOCH2CH2)2N — CH2 — P(O)(OC2Ho)2]
bei vergleichbaren Bedingungen verglichen. In der Verfahren zur Herstellung von Phosphonaten
Anmelder:
Pure Chemicals Limited,
Liverpool, Lancashire (Großbritannien)
Vertreter:
Dipl.-Chem. W. Rücker, Patentanwalt.
3000 Hannover, Am Klagesmarkt 10-11
Als Erfinder benannt:
Lester Friedman, Whitestone, N. Y. (V. St. A.)
Beanspruchte Priorität:
V. St. v. Amerika vom 17. Oktober 1961
(145 749),
vom 11. April 1962 (186 662)
sich anschließenden Tabelle 1 ist die Zubereitung der Schäume mit den zu vergleichenden Stoffen dargestellt.
Dabei zeigte es sich, daß der Schaum, der Fyrol 6 enthält, eine außerordentlich grobe Zellstruktur
aufwies. Die Zufügung von 0,15 g Zinnoktat führte zu einer geringen Verbesserung, jedoch waren
auch dann noch diese Schäume wesentlich schlechter als jene, die mit den Polyolen erhalten wurden. In
allen Fällen wurden die Schäume mehrere Stunden bei 70°C aushärten gelassen. Es ist der Tabelle zu
entnehmen, daß bei Verwendung einer höheren Konzentration ein Produkt erhalten war, das selbstverlöschende
Eigenschaften hatte. In geringerer Konzentration brannte es weiter. Der Schaum indessen
ist in jedem Fall unbefriedigend und bricht auseinander. Es sei noch daraufhingewiesen, daß Fyrol den
Nachteil hat, daß die feuerhemmende Wirkung mit der Zeit nachläßt, weil das Produkt ausgeschwitzt
wird, während die erfindungsgemäßen Verbindungen in die Molekularstruktur des Kunststoffes mit eingebaut
werden.
Aus den Tabellen, insbesondere Tabelle 2, geht hervor, daß die Schäume mit den erfindungsgemäßen
Verbindungen nicht nur eine nicht entflammbare Eigenschaft erhalten, sondern auch die Herstellung
eines qualitativ hochwertigen Schaumstoffes zulassen.
709 720/536
In der Tabelle 2 ist als schwer entflammbarer Zusatz Tris-(chloräthyl)-phosphat verwendet worden, das
die Schwerentflammbarkeit dem Schaumstoff dadurch verleiht, daß es 16,5% Chlor enthält. Aus der
Monographie »Rigid Plastics Foams«, S. 14 (F e r rigno, Reinhold), geht hervor, daß 25",U
Chlor etwa 4 bis 50Zo Phosphor äquivalent sind hinsichtlich
der Schwerentflammbarkeit. Das bedeutet, daß dadurch der Phosphorgehalt des Tris-(chloräthyl)-phosphats
praktisch auf 2,1 "/o erhöht ist.
Wenn nicht anders angegeben, beziehen sich alle Teile und Prozente auf Gewicht.
Tabelle 1 Zusammensetzung von Polyurethanschäumen
100 g
w) g Sorhilii|piil\«l l\'i:i\ LB
<>u« OUs;
76 g
67 g '< K)Og
Tris-(DPG)-phosphonat
DPG-tetroldiphosphonat
DPG-pentoltriphosphonat
DPG-hexoltetraphosphonat ...
DPG-hexoltetraphosphonat ...
Fyrol 6
Tris-(2-chloräthyl)-phosphat ...
Triäthylamin
Arcton 11 ·
Silikon L. 520 (U. C. C.)
Dabco-Katalysator
M. D. 1. (85,5% rein)
Phosphorgehalt (%)
Rührzeit bei 1000 U/Min. (Sek.;
»Cream«-Zeit (Sek.)
Steigzeit. (Sek.)
»Tack free time« (Sek.)
Steighöhe (cm)
DPG = Dipropylenglykol.
0,9
35 0,7 0,7 127,8
30
30 225 300
18
40
0,9
35 0,7 0,7 114,7 1,15 23 25 105 120
18 40
0,7
35
0,7
0,7
105,3
1,53
30
30
180
285
18
35
0,7
0,7
105,3
1,53
30
30
180
285
18
40
0,7
35
0,7
0,5
102,1
1,64
30
30
170
255
18 ,
30
30
170
255
18 ,
0,7
35
0,7
0,5
102,6
1,59
23
25
120
150
18
35
0,7
0,5
102,6
1,59
23
25
120
150
18
0,9
33
35
,9
0."7 | 0,7 |
0,7 | 0,7 |
121,4 | 121,3 |
1,15 | 1,60 |
30 | 30 |
80 | 80 |
780 | 450 |
1020 | 720 |
16,5 | 15 |
46,2 0,9 35 0,7 0,7 128,0 1,63 30 80 295 560 21,6
Tabelle 2 Entflammbarkeit von Polyurethanschäumen
Flammenhemmender Bestandteil
Anzahl der
geprüften
Proben
Durchschnittliche Brennzeit
(Sekunden) Durchschnitt
maximale
verbrannte
Länge
(cm)
minimale
verbrannte
Länge
(cm)
Beurteilung
Kontrolle ohne Phosphit ..
Tris-DPG-Phosphonat
DPG-Tetroldiphosphonat ..
DPG-Pentoltriphosphat ...
DPG-Hexoltetraphosphonat
DPG-Pentoltriphosphat ...
DPG-Hexoltetraphosphonat
Fyrol 6 (1,15% P)
Fyrol 6 (1,6% P)
Tris-( Chloräthylphosphat) .
2 4 2 4 4
3 4
117,5 25,3 18,3 vollkommen verbrannt
6,4 | 3,8 |
3,8 | 2,5 |
3,1 | 1,9 |
2,54 | 0,9 |
10,8 | 3,1 |
3,1 | 1,6 |
1,2 | 0,6 |
brennt
verlöscht von selbst verlöscht von selbst verlöscht von selbst verlöscht von selbst *
(brennt kaum) brennt**
verlöscht von selbst brennt nicht
*) In einem Fall betrug die maximale verbrannte Länge 3,81 cm, obwohl der Schaum als »verlöscht von selbst« bezeichnet war.
**) In .einem Fall war der Schaum vollständig verbrannt und wurde deshalb als »brennt« bezeichnet.
Dipropylenglykolhydroxypropoxypropanphosphonat (Bisdipropylenglykolester der hydroxypropoxypropanphosphorigen
Säure) wurde durch Behandeln von Tris-(dipropylenglykol)-phosphit mit 5 Molprozent
n-Butylbromid 8 Stunden lang bei 125 bis 135°C hergestellt, wobei nach dieser Zeit eine Zunahme an
P = O-Bindungen durch Infrarotanalyse nicht mehr festzustellen war. Flüchtige Stoffe wurden bei 150C
und 10 mm Druck abgetrieben. Der flüssige Rest bestand im wesentlichen aus reinem Dipropylenglykolhydroxypropoxypropanphosphonat,
welches mit ungefähr 5% Dipropylenglykolbutanphosphonat
verunreinigt war. Das Bis-(dipropylenglykolphosphonat) hatte die Formel
HOC3H,, — O — C3H0 — O — P — C3H6 — O — C3H0 — OH
HO — C3H0 — O — C3H6 —
Die OH-Zahl beträgt 390, P = 7,2"/« und n?
1,4634.
Die Verbindung gemäß Beispiel 1 ist eine der bevorzugtesten der Erfindung.
1 Mol Tris-(dipropylenglykol)-phosphit wurde mit 5 Mol Propylenchlorhydrin( 1 - Chlor - 2 - hydroxy propan)
8 Stunden lang bei 125 bis 135 C erhitzt. Der Überschuß an Propyleiichlorhydrin und der sich
bildende Chlorpropylhydroxypropyläther wurden im Vakuum bei 10 Torr abgetrieben und das als Rückstand
verbleibende Bis-(dipropylenglykol-2-hydroxypropan) - phosphonat gewonnen; OH-Zahl 546,
P ----- 10.011M,.
Beispiel 1 wurde an Stelle von Tris-(dipropylenglykoU-phosphit
mit einem Mol Tris-(tripropylenglykoU-phosphit wiederholt, wobei sich Bis-(tripropylenglykol
- 2 - hydroxypropoxypropoxypropan) phosphonat bildet, die OH - Zahl beträgt 279 und
P ^ 5,4" i). In ähnlicher Weise erhält man, wenn Tris-(dipropylenglykol)-phosphit
im Beispiel 1 mit einem Mol Tris - (Propylenoxid -1,2,6 - Hexantrioladdukt)-phosphit
ausgetauscht wird, die Umlagerung des Phosphits zum Tris-( Propylenoxid-1,2,6-Hexantrioladdukt)-hexolphosphonat
mit der OH-Zahl ^ 148. P - 1,4% und nf = 1,4600.
Di - (propylenglykoltetrol) - diphosphit wurde mit 2,5 Molprozent Butylbromid behandelt, bis die Phosphonatbildung
vollständig zu sein schien, was bei 125 bis 135 C nach etwa 8 Stunden anzunehmen war.
Flüchtige Bestandteile wurden bei 10 Torr abgetrieben. Die leicht gefärbte, viskose Flüssigkeit war
ein Gemisch aus
HORO O
O OROH
\ | HORO | I! D D Jr K. |
!/ P |
OROH |
HORO 0 | OROH / |
|||
P- / |
/ — P \ |
|||
/ HORO |
-R —0 | \ OROH |
||
HOR \ |
0 0 ROH J I/ P—OROP |
HORO ROH
in dem R der Dipropylätherrest ist:
-C3He-O-CaH6-
Di-(propylenglykoltetrol)-diphosphonat: n!i -;: 1,4655,
OH-Zahl = 310 und P = 8,5%.
In ähnlicher Weise kann Tri-(propylenglykoltetrol)-diphosphit mit Butylbromid behandelt werden, um
ein analoges Produkt, Tri-(propylenglykoltetrol)-diphosphonat, OH-Zahl = 220, P = 6,1%, zu erhalten.
Di-(propylenglykolpentoltri)-phosphit wurde mit 2,5 Molprozent Butylbromid bei 125 bis 135 C bchandelt,
bis die Phosphonatbildung beendet war. Flüchtige Bestandteile wurden bei 10 Torr abgetrieben.
Das Produkt, welches als Rückstand verblieb, ist Di-(propylenglykolpentol)-triphosphonat
mit einem n'g = 1,4670, einer OH-Zahl 273 und
einem Phosphorgehalt von 9,1%, welches mit dem Ausgangsphosphit isomer ist. In ähnlicher Weise
kann Polypropylenglykol-tetroldiphosphit (Molgewicht 425) mit Hilfe von 2,5 Molprozent Butylbromid
zum entsprechenden Phosphonat isomerisiert werden.
nf = 1,4552, OH-Zahl = 103, P =--- 2.8»/,,.
Tris - (polypropylenglykol) - phosphit (Molgewicht 425) wurde mit 5 Molprozent n-Butylbromid
bei 125 bis 135 C erhitzt, bis keine Zunahme an P — O-Bindungen bei der Infrarotanalyse festgestellt
wurde. Flüchtige Stoffe wurden bei 150 C und 10 Torr abgetrieben. Der flüssige Rest bestand im
wesentlichen aus Bis-(polypropylenglykol-hydroxypolypropoxypropan)-phosphonat,
in welchem die Hydroxylpolypropoxypropan-Gruppe ein Molgewicht von 425 hatte. Tris-(polypropylenglykol)-phosphonat
(Molgewicht 425): n!i = 1,4528, OH-Zahl = 129, Phosphorgehalt = 2,4%.
In ähnlicher Weise kann unter Verwendung des Verfahrens gemäß Beispiel 6 Tris-(glyzerin-propylenoxidaddukt)-phosphit
mit 5 Molprozent n-Butylbromid zum entsprechenden Hexolphosphonat isomerisiert
werden, welches ein Molgewicht von ungefähr 3000 hat. Die OH-Zahl ist 112, und der Phosphorgehalt
beträgt 1,0%.
In entsprechender Weise wird ein Hexolphosphonat mit dem Molgewicht von 2100 erhalten, wenn Tris-(propylenoxid-l,2,6-hexantrioladdukt)-phosphit gemäß Beispiel 6 isomerisiert wird. Auch Tris-(pentaerythritpropylenoxidaddukt)-phosphit mit dem Molgewicht 450 des Adduktes kann gemäß Beispiel 6 zum entsprechenden Nonylphosphonat mit dem Molgewicht von ungefähr 1230 isomerisiert werden.
OH-Zahl = 410, Phosphorgehalt = 2,5%.
Gemäß Beispiel 6 kann der Ester aus 3 Mol l,l,3-Tris-p-(2-hydroxypropoxy)-phenylpropan mit 1 Mol phosphoriger Säure zum entsprechenden Hexolphosphonat isomerisiert werden. Diese Phosphonate sind zur Herstellung farbfähiger, fester Polyurethanschäume geeignet.
In entsprechender Weise wird ein Hexolphosphonat mit dem Molgewicht von 2100 erhalten, wenn Tris-(propylenoxid-l,2,6-hexantrioladdukt)-phosphit gemäß Beispiel 6 isomerisiert wird. Auch Tris-(pentaerythritpropylenoxidaddukt)-phosphit mit dem Molgewicht 450 des Adduktes kann gemäß Beispiel 6 zum entsprechenden Nonylphosphonat mit dem Molgewicht von ungefähr 1230 isomerisiert werden.
OH-Zahl = 410, Phosphorgehalt = 2,5%.
Gemäß Beispiel 6 kann der Ester aus 3 Mol l,l,3-Tris-p-(2-hydroxypropoxy)-phenylpropan mit 1 Mol phosphoriger Säure zum entsprechenden Hexolphosphonat isomerisiert werden. Diese Phosphonate sind zur Herstellung farbfähiger, fester Polyurethanschäume geeignet.
Claims (1)
- Patentanspruch:Verfahren zur Herstellung von Phosphonaten, dadurch gekennzeichnet, daß man ein Tris-(polypropylenglykol)-phosphit mit einer oder mehreren Phosphitgruppierungen in an sich bekannter Weise a) mit einer katalytischen Menge oder b) mit einem Überschuß eines Alkv'halogenids bei erhöhter Temperatur umsetzt.In Betracht gezogene Druckschriften:USA.-Patentschrift Nr. 2 753 368;Journal of the Chemical Society, 1953, S. 2224 bis 2234;Journal of the American Chemical Society, 75 (1953), S. 1500 bis 1501;Z. obst. Chim., 1961, Nr. 6, S. 2052 bis 2057;Kosolapoff, Organophosphorus Compounds, 1950, S. 121 bis 123.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US129529A US3081331A (en) | 1961-08-07 | 1961-08-07 | Poly phosphorus ester condensates and their preparation |
US135751A US3142650A (en) | 1961-05-15 | 1961-09-05 | Polyurethanes from tris-polypropylene glycol phosphites |
US145749A US3142651A (en) | 1961-08-07 | 1961-10-17 | Polyurethanes from polyphosphorus phosphites and phosphonates |
US186662A US3092651A (en) | 1961-08-07 | 1962-04-11 | 2-hydroxyalkane phosphonate and polyphosphonate hydroxyalkyl esters |
US201240A US3139450A (en) | 1961-08-07 | 1962-06-11 | Alkaneetherpolyol phosphonate esters |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1259338B true DE1259338B (de) | 1968-01-25 |
Family
ID=27537835
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP29865A Pending DE1236184B (de) | 1961-08-07 | Verfahren zur Herstellung von gegebenenfalls verschaeumten Polyurethanen | |
DE19621520502 Pending DE1520502A1 (de) | 1961-08-07 | 1962-07-27 | Organische Ester von Phosphiten,Phosphaten und Thiophosphaten sowie Verfahren zu deren Herstellung |
DE19621520503 Pending DE1520503A1 (de) | 1961-08-07 | 1962-08-04 | Verfahren zur Herstellung von organischen Phosphorverbindungen |
DEP30370A Pending DE1259338B (de) | 1961-08-07 | 1962-10-16 | Verfahren zur Herstellung von Phosphonaten |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP29865A Pending DE1236184B (de) | 1961-08-07 | Verfahren zur Herstellung von gegebenenfalls verschaeumten Polyurethanen | |
DE19621520502 Pending DE1520502A1 (de) | 1961-08-07 | 1962-07-27 | Organische Ester von Phosphiten,Phosphaten und Thiophosphaten sowie Verfahren zu deren Herstellung |
DE19621520503 Pending DE1520503A1 (de) | 1961-08-07 | 1962-08-04 | Verfahren zur Herstellung von organischen Phosphorverbindungen |
Country Status (4)
Country | Link |
---|---|
US (3) | US3142651A (de) |
DE (4) | DE1520502A1 (de) |
FR (3) | FR1338387A (de) |
GB (6) | GB990186A (de) |
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US3246051A (en) * | 1964-05-28 | 1966-04-12 | Weston Chemical Corp | Phosphite esters having free hydroxyl groups |
GB973578A (en) * | 1961-12-12 | 1964-10-28 | Albright & Wilson Mfg Ltd | Polyurethane materials |
US3406153A (en) * | 1962-05-16 | 1968-10-15 | Du Pont | Process of producing polyethylene terephthalate |
US3261814A (en) * | 1962-09-07 | 1966-07-19 | Union Carbide Corp | Hydroxylated sugar phosphite based polyurethanes |
NL298956A (de) * | 1962-10-08 | |||
NL299732A (de) * | 1962-11-01 | |||
US3284386A (en) * | 1963-01-30 | 1966-11-08 | Synthetic Products Co | Vinyl halide resins stabilized with metallo-phosphorous compounds |
US3282873A (en) * | 1963-04-22 | 1966-11-01 | George H Slack | Composition comprising the reaction product of a resinous polyester, hexionic acid, water and ammonium hydroxide |
US3314957A (en) * | 1963-05-21 | 1967-04-18 | Union Carbide Corp | Aminomethyl-phosphonates |
US3310609A (en) * | 1963-07-16 | 1967-03-21 | Hooker Chemical Corp | Pentaerythritol phosphites |
US3287299A (en) * | 1963-07-29 | 1966-11-22 | Tenneco Chem | Vinyl halide resin stabilizers comprising phosphites prepared from polyols, secondary phosphites and tertiary phosphites |
US3179629A (en) * | 1963-10-14 | 1965-04-20 | Weston Chemical Corp | Chlorine and phosphorus containing polyurethanes |
US3341343A (en) * | 1963-11-12 | 1967-09-12 | Gen Anilline & Film Corp | Hydrophobic polymeric resin containing phosphate ester antistatic agent and process for producing antistatic properties |
US3538196A (en) * | 1963-12-11 | 1970-11-03 | Hooker Chemical Corp | Bis(oxypropylated pentaerythritol) oxypropylated pentaerythritol phosphonate |
US3515776A (en) * | 1964-02-28 | 1970-06-02 | Hooker Chemical Corp | Mixed esters of phosphonic acid and preparation |
US3385801A (en) * | 1964-05-05 | 1968-05-28 | Monsanto Co | Flame-resistant polyurethanes |
US3220961A (en) * | 1964-05-28 | 1965-11-30 | Weston Chemical Corp | Phosphate and thiophosphate urethanes |
US3332893A (en) * | 1964-06-11 | 1967-07-25 | Monsanto Co | Flame-resistant polyurethanes |
GB1020254A (en) * | 1964-06-29 | 1966-02-16 | Shell Int Research | Improvements in or relating to polyurethanes |
US3305526A (en) * | 1964-07-07 | 1967-02-21 | Weston Chemical Corp | Phenoxy phosphite polymers |
US3458457A (en) * | 1964-08-06 | 1969-07-29 | Albright & Wilson Mfg Ltd | Phosphorus-containing flame retardant polyurethanes |
US3437607A (en) * | 1965-03-31 | 1969-04-08 | Upjohn Co | Polyurethane pre-mixes containing dihydroxy nitrogen containing phosphonates |
US3422037A (en) * | 1965-07-03 | 1969-01-14 | Mitsui Chem Ind Co Ltd | Process for the production of flame resistant polyurethane foams |
US3382236A (en) * | 1965-07-23 | 1968-05-07 | Weston Chemical Corp | Oxypropylated sucrose phosphites |
US3317510A (en) * | 1965-10-20 | 1967-05-02 | Monsanto Co | Method of preparing polyphosphoruspolyol esters |
US3382191A (en) * | 1965-12-07 | 1968-05-07 | Weston Chemical Corp | Fire-retardant phosphorouscontaining additives |
US3326939A (en) * | 1966-04-21 | 1967-06-20 | Weston Chemical Corp | Aeh phosphites |
DE1293766B (de) * | 1966-06-29 | 1969-04-30 | Kalk Chemische Fabrik Gmbh | Phosphor und Hydroxylgruppen enthaltende AEther, Polyaether und Verfahren zu deren Herstellung |
DE2236037C3 (de) * | 1972-07-22 | 1975-04-17 | Farbwerke Hoechst Ag Vormals Meister Lucius & Bruening, 6000 Frankfurt | Schwer entflammbare Fäden und Fasern aus Polyester |
JPS53127552A (en) * | 1977-03-14 | 1978-11-07 | Daicel Chem Ind Ltd | Cellulose organic acid ester resin composition |
US4616044A (en) * | 1985-01-25 | 1986-10-07 | Stauffer Chemical Company | Heat laminatable polyether urethane foam |
US4654105A (en) * | 1985-01-25 | 1987-03-31 | Stauffer Chemical Company | Process for producing laminated polyether urethane foam |
US4652485A (en) * | 1985-01-25 | 1987-03-24 | Stauffer Chemical Company | Laminated heat-sealed polyether urethane foam |
DE4342973A1 (de) * | 1993-12-16 | 1995-06-22 | Hoechst Ag | Flammwidrige Polyurethane |
MX9604872A (es) | 1995-10-27 | 1997-04-30 | Basf Corp | Composiciones de poliol que proporcionan resistencia mejorada a las llamas y factores k curados a las espumas de poliuretano. |
ES2154111B1 (es) * | 1996-09-25 | 2001-10-16 | Witco Vinyl Additives Gmbh | Bisfosfitos monomeros y oligomeros como estabilizadores del poli(cloruro de vinilo). |
US7208554B2 (en) * | 2004-04-07 | 2007-04-24 | Rhodia Inc. | Polyoxyalkylene phosphonates and improved process for their synthesis |
WO2008073872A1 (en) * | 2006-12-11 | 2008-06-19 | Albemarle Corporation | Organophosphonate oligomers, mixtures thereof, and processes for producing organophosphonate oligomers and mixtures thereof |
RU2468051C2 (ru) * | 2008-07-03 | 2012-11-27 | Рико Компани, Лтд. | Огнестойкая композиция смолы |
TW201022335A (en) * | 2008-10-21 | 2010-06-16 | Albemarle Corp | Mixed glycol polyphosphonate compounds |
DE102009029089A1 (de) | 2009-09-02 | 2011-03-03 | Evonik Goldschmidt Gmbh | Phosphorarme Laminieradditive mit geringer Emission, verbesserter Anfangshaftung und verbesserter Hydrolysestabilität |
CN117327251B (zh) * | 2023-12-01 | 2024-04-12 | 山东一诺威聚氨酯股份有限公司 | 高强度阻燃聚氨酯硬泡及其制备方法 |
Citations (1)
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US2753368A (en) * | 1950-11-13 | 1956-07-03 | Shell Dev | Higher alkyl esters of phosphonic acids |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2177984A (en) * | 1937-02-11 | 1939-10-31 | Benjamin R Harris | Phosphoric acid esters and method of producing them |
US2176080A (en) * | 1938-01-08 | 1939-10-17 | Emulsol Corp | Egg composition |
US2196755A (en) * | 1938-12-21 | 1940-04-09 | Eastman Kodak Co | Yarn conditioning process |
US2372244A (en) * | 1941-09-24 | 1945-03-27 | Standard Oil Co | Esters of acids of phosphorus |
US2683168A (en) * | 1950-12-22 | 1954-07-06 | California Research Corp | Preparation of organo phosphonyl chlorides |
US2693482A (en) * | 1950-12-30 | 1954-11-02 | California Research Corp | Preparation of alkene phosphonous acids |
US2795609A (en) * | 1954-07-06 | 1957-06-11 | California Research Corp | Halogenated phenylalkane phosphonyl chlorides |
US2950262A (en) * | 1955-08-03 | 1960-08-23 | Pittsburgh Plate Glass Co | Preparation of foamed polyurethane using salt of mannich base as catalyst |
US3007884A (en) * | 1959-06-10 | 1961-11-07 | Allied Chem | Cellular polyurethane resin containing primary-2-hydroxyethylphosphate and method ofpreparing same |
NL254779A (de) * | 1959-08-11 | |||
US3047608A (en) * | 1960-09-15 | 1962-07-31 | Weston Chemical Corp | Phosphites |
US3053878A (en) * | 1961-05-23 | 1962-09-11 | Weston Chemical Corp | Pentaerythritol phosphite esters |
-
0
- DE DEP29865A patent/DE1236184B/de active Pending
-
1961
- 1961-10-17 US US145749A patent/US3142651A/en not_active Expired - Lifetime
-
1962
- 1962-04-11 US US186662A patent/US3092651A/en not_active Expired - Lifetime
- 1962-04-12 GB GB14136/62A patent/GB990186A/en not_active Expired
- 1962-06-11 US US201240A patent/US3139450A/en not_active Expired - Lifetime
- 1962-07-04 FR FR902905A patent/FR1338387A/fr not_active Expired
- 1962-07-13 GB GB26970/62A patent/GB1011117A/en not_active Expired
- 1962-07-19 GB GB27746/62A patent/GB1011118A/en not_active Expired
- 1962-07-24 GB GB28478/62D patent/GB1011119A/en not_active Expired
- 1962-07-24 GB GB10035/65A patent/GB1018320A/en not_active Expired
- 1962-07-27 DE DE19621520502 patent/DE1520502A1/de active Pending
- 1962-08-04 DE DE19621520503 patent/DE1520503A1/de active Pending
- 1962-08-07 FR FR906323A patent/FR1359075A/fr not_active Expired
- 1962-08-07 FR FR906321A patent/FR1356931A/fr not_active Expired
- 1962-10-12 GB GB38674/62A patent/GB1024814A/en not_active Expired
- 1962-10-16 DE DEP30370A patent/DE1259338B/de active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2753368A (en) * | 1950-11-13 | 1956-07-03 | Shell Dev | Higher alkyl esters of phosphonic acids |
Also Published As
Publication number | Publication date |
---|---|
FR1356931A (fr) | 1964-04-03 |
US3139450A (en) | 1964-06-30 |
GB1018320A (en) | 1966-01-26 |
GB1024814A (en) | 1966-04-06 |
DE1520503A1 (de) | 1969-04-10 |
GB1011118A (en) | 1965-11-24 |
US3092651A (en) | 1963-06-04 |
GB1011117A (en) | 1965-11-24 |
GB1011119A (en) | 1965-11-24 |
GB990186A (en) | 1965-04-28 |
DE1236184B (de) | 1967-03-09 |
US3142651A (en) | 1964-07-28 |
FR1338387A (fr) | 1963-09-27 |
FR1359075A (fr) | 1964-04-24 |
DE1520502A1 (de) | 1969-04-10 |
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