DE2047195A1 - Mittel zum Flammfestmachen von Kunststoffen und Verfahren zu deren Herstellung - Google Patents
Mittel zum Flammfestmachen von Kunststoffen und Verfahren zu deren HerstellungInfo
- Publication number
- DE2047195A1 DE2047195A1 DE19702047195 DE2047195A DE2047195A1 DE 2047195 A1 DE2047195 A1 DE 2047195A1 DE 19702047195 DE19702047195 DE 19702047195 DE 2047195 A DE2047195 A DE 2047195A DE 2047195 A1 DE2047195 A1 DE 2047195A1
- Authority
- DE
- Germany
- Prior art keywords
- phosphate
- bis
- dibromopropyl
- composition according
- agent
- 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
- 229920003023 plastic Polymers 0.000 title claims description 17
- 239000004033 plastic Substances 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 9
- 239000003063 flame retardant Substances 0.000 title description 18
- 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 title description 12
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- -1 dibromopropyl bis (1-chloro-2-hydroxypropyl) phosphate Chemical compound 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- UJSSNDKVUQJEGE-UHFFFAOYSA-N dichloro propyl phosphate Chemical compound CCCOP(=O)(OCl)OCl UJSSNDKVUQJEGE-UHFFFAOYSA-N 0.000 claims description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000003016 phosphoric acids Chemical class 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- JUZVWHAYFZNKCC-UHFFFAOYSA-N bis(2-hydroxyethyl) hydrogen phosphate Chemical compound OCCOP(O)(=O)OCCO JUZVWHAYFZNKCC-UHFFFAOYSA-N 0.000 claims 1
- PCIBVZXUNDZWRL-UHFFFAOYSA-N ethylene glycol monophosphate Chemical compound OCCOP(O)(O)=O PCIBVZXUNDZWRL-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QQWVXAYFWMTVMD-UHFFFAOYSA-N bis(3,3-dibromopropyl) hydrogen phosphate Chemical compound BrC(Br)CCOP(=O)(O)OCCC(Br)Br QQWVXAYFWMTVMD-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- NMDGMYNXRRCPGM-UHFFFAOYSA-N dibromo propyl phosphate Chemical compound P(=O)(OBr)(OBr)OCCC NMDGMYNXRRCPGM-UHFFFAOYSA-N 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000320 mechanical mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Classifications
-
- 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/3885—Phosphate compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702047195 DE2047195A1 (de) | 1970-09-25 | 1970-09-25 | Mittel zum Flammfestmachen von Kunststoffen und Verfahren zu deren Herstellung |
| FR7129422A FR2105859A5 (https=) | 1970-09-25 | 1971-08-11 | |
| BE771473A BE771473A (fr) | 1970-09-25 | 1971-08-18 | Agent d'ignifugation de matieres synthetiques et procede pour sa preparation |
| NL7111994A NL7111994A (https=) | 1970-09-25 | 1971-08-31 | |
| IT12934/71A IT943557B (it) | 1970-09-25 | 1971-09-18 | Sostanze per rendere ininfiammabi li le materie plastiche sintetiche e processo per la loro fabbricazio ne |
| US00182543A US3781388A (en) | 1970-09-25 | 1971-09-21 | Phosphates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702047195 DE2047195A1 (de) | 1970-09-25 | 1970-09-25 | Mittel zum Flammfestmachen von Kunststoffen und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2047195A1 true DE2047195A1 (de) | 1972-03-30 |
Family
ID=5783352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702047195 Pending DE2047195A1 (de) | 1970-09-25 | 1970-09-25 | Mittel zum Flammfestmachen von Kunststoffen und Verfahren zu deren Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3781388A (https=) |
| BE (1) | BE771473A (https=) |
| DE (1) | DE2047195A1 (https=) |
| FR (1) | FR2105859A5 (https=) |
| IT (1) | IT943557B (https=) |
| NL (1) | NL7111994A (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1317468A (en) * | 1969-09-30 | 1973-05-16 | Cotton Producers Inst | Process for rendering cellulosic textile material flame retardant |
| US3893970A (en) * | 1971-10-01 | 1975-07-08 | Cities Service Co | Fire retardant polypropylene compositions containing a halogenated flame retardant and a phosphite adjuvant |
| AT329511B (de) * | 1972-05-25 | 1976-05-10 | Schill & Seilacher | Verfahren zur wasch- und chemischreinigungsbestandigen flammfestausrustung von textilmaterialien |
| US4098759A (en) * | 1973-08-07 | 1978-07-04 | Hoechst Aktiengesellschaft | Bromine-containing cyclic phosphonic acid esters |
| US4049617A (en) * | 1976-01-19 | 1977-09-20 | Velsicol Chemical Corporation | Reactive flame retardants |
| DE2708790C2 (de) * | 1977-03-01 | 1982-02-25 | Akzo Gmbh, 5600 Wuppertal | Lineare Homo- oder Copolyester, Verfahren zur Herstellung der Polyester und ihre Verwendung |
| JPS53122817A (en) * | 1977-03-30 | 1978-10-26 | Teijin Ltd | Wholly aromatic polyamide fibers having improved flame resistance |
| US4179483A (en) * | 1977-09-09 | 1979-12-18 | Monsanto Company | 2-Chloroethyl phosphonates |
| US4179482A (en) * | 1977-09-09 | 1979-12-18 | Monsanto Company | 2-Chloroethyl phosphonate compositions |
| US4193914A (en) * | 1977-09-09 | 1980-03-18 | Monsanto Company | Phosphorus-containing propionates |
| US4178281A (en) * | 1978-05-30 | 1979-12-11 | Borg-Warner Corporation | Flame-retardant polycarbonate compositions |
| US4234696A (en) * | 1979-04-06 | 1980-11-18 | Monsanto Company | 2-Chloroethyl phosphonate compositions |
| FR2567127B1 (fr) * | 1984-07-05 | 1988-05-20 | Charbonnages Ste Chimique | Composes organophosphores, leur procede de fabrication et leur application a l'ignifugation de polymeres |
| US4696963A (en) * | 1985-10-10 | 1987-09-29 | Great Lakes Chemical Corporation | Halogenated alkyl phosphate esters and polymer systems incorporating them |
| US5082867A (en) * | 1989-09-28 | 1992-01-21 | Great Lakes Chemical Corporation | Flame retardant flexible polyurethane foam compositions |
-
1970
- 1970-09-25 DE DE19702047195 patent/DE2047195A1/de active Pending
-
1971
- 1971-08-11 FR FR7129422A patent/FR2105859A5/fr not_active Expired
- 1971-08-18 BE BE771473A patent/BE771473A/xx unknown
- 1971-08-31 NL NL7111994A patent/NL7111994A/xx unknown
- 1971-09-18 IT IT12934/71A patent/IT943557B/it active
- 1971-09-21 US US00182543A patent/US3781388A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT943557B (it) | 1973-04-10 |
| BE771473A (fr) | 1971-12-31 |
| FR2105859A5 (https=) | 1972-04-28 |
| NL7111994A (https=) | 1972-03-28 |
| US3781388A (en) | 1973-12-25 |
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