DE2029294A1 - Neue Halogen-substituierte Phosphorsäureester-isocyanate, ein Verfahren zu ihrer Herstellung sowie ihrer Verwendung als reaktive Flammschutzmittel - Google Patents
Neue Halogen-substituierte Phosphorsäureester-isocyanate, ein Verfahren zu ihrer Herstellung sowie ihrer Verwendung als reaktive FlammschutzmittelInfo
- Publication number
- DE2029294A1 DE2029294A1 DE19702029294 DE2029294A DE2029294A1 DE 2029294 A1 DE2029294 A1 DE 2029294A1 DE 19702029294 DE19702029294 DE 19702029294 DE 2029294 A DE2029294 A DE 2029294A DE 2029294 A1 DE2029294 A1 DE 2029294A1
- Authority
- DE
- Germany
- Prior art keywords
- acid ester
- phosphoric acid
- isocyanates
- reaction
- flame retardants
- 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
- 239000012948 isocyanate Substances 0.000 title claims description 21
- -1 phosphoric acid ester isocyanates Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 14
- 239000003063 flame retardant Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000004744 fabric Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 150000002924 oxiranes Chemical class 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229950011008 tetrachloroethylene Drugs 0.000 description 3
- 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 2
- TZGJFPLIKGCMJB-UHFFFAOYSA-N 2-isocyanato-1,3,2-dioxaphospholane Chemical class O=C=NP1OCCO1 TZGJFPLIKGCMJB-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- UFKLREPTLFKDST-UHFFFAOYSA-N isocyanic acid;hydrobromide Chemical compound Br.N=C=O UFKLREPTLFKDST-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- FZRJLBJACDITKM-UHFFFAOYSA-N 1,3,2-dioxaphospholane Chemical compound C1COPO1 FZRJLBJACDITKM-UHFFFAOYSA-N 0.000 description 1
- QVOOVJHSIPCFPD-UHFFFAOYSA-N 2,3-dichloropropyl dihydrogen phosphate Chemical compound OP(O)(=O)OCC(Cl)CCl QVOOVJHSIPCFPD-UHFFFAOYSA-N 0.000 description 1
- CBJNWWDLRGZXAE-UHFFFAOYSA-N 2-bromopropyl dihydrogen phosphate Chemical compound CC(Br)COP(O)(O)=O CBJNWWDLRGZXAE-UHFFFAOYSA-N 0.000 description 1
- LLUIQISTLAXOHC-UHFFFAOYSA-N 2-chloropropyl dihydrogen phosphate Chemical compound CC(Cl)COP(O)(O)=O LLUIQISTLAXOHC-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 101150018711 AASS gene Proteins 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
- 150000003015 phosphoric acid halides Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-AHCXROLUSA-N titanium-44 Chemical compound [44Ti] RTAQQCXQSZGOHL-AHCXROLUSA-N 0.000 description 1
- 210000002268 wool Anatomy 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
- C07F9/657154—Cyclic esteramides 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/226—Amides of acids of phosphorus containing the structure P-isocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- 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
- C08K5/5399—Phosphorus bound to nitrogen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Fireproofing Substances (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702029294 DE2029294A1 (de) | 1970-06-13 | 1970-06-13 | Neue Halogen-substituierte Phosphorsäureester-isocyanate, ein Verfahren zu ihrer Herstellung sowie ihrer Verwendung als reaktive Flammschutzmittel |
| GB1965471A GB1305851A (enExample) | 1970-06-13 | 1971-06-09 | |
| BE768400A BE768400A (fr) | 1970-06-13 | 1971-06-11 | Nouveaux isocyanato-phosphates de bis (halogenoalkyle) utiles comme agents ignifugeants reactifs et leur procede de preparation |
| FR7121362A FR2096265A5 (enExample) | 1970-06-13 | 1971-06-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702029294 DE2029294A1 (de) | 1970-06-13 | 1970-06-13 | Neue Halogen-substituierte Phosphorsäureester-isocyanate, ein Verfahren zu ihrer Herstellung sowie ihrer Verwendung als reaktive Flammschutzmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2029294A1 true DE2029294A1 (de) | 1971-12-30 |
Family
ID=5773916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702029294 Pending DE2029294A1 (de) | 1970-06-13 | 1970-06-13 | Neue Halogen-substituierte Phosphorsäureester-isocyanate, ein Verfahren zu ihrer Herstellung sowie ihrer Verwendung als reaktive Flammschutzmittel |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE768400A (enExample) |
| DE (1) | DE2029294A1 (enExample) |
| FR (1) | FR2096265A5 (enExample) |
| GB (1) | GB1305851A (enExample) |
-
1970
- 1970-06-13 DE DE19702029294 patent/DE2029294A1/de active Pending
-
1971
- 1971-06-09 GB GB1965471A patent/GB1305851A/en not_active Expired
- 1971-06-11 BE BE768400A patent/BE768400A/xx unknown
- 1971-06-11 FR FR7121362A patent/FR2096265A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2096265A5 (enExample) | 1972-02-11 |
| BE768400A (fr) | 1971-11-03 |
| GB1305851A (enExample) | 1973-02-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2502260C3 (de) | Verfahren zur Herstellung eines zelligen Polymeren, dessen hauptsächlich wiederkehrende Polymereneinheit aus einer Isocyanurateinheit besteht | |
| DE2701856C3 (de) | Dioxaphosphorinane und sie enthaltende Polyurethane, Polyester oder Polystyrole | |
| DE4026097A1 (de) | Waessrige dispersionen von fluorhaltigen polymeren | |
| DE1087109B (de) | Verfahren zur Flammschutz-Ausruestung | |
| DE2342888A1 (de) | Fluor und schwefel enthaltende stoffzusammensetzungen | |
| DE2029294A1 (de) | Neue Halogen-substituierte Phosphorsäureester-isocyanate, ein Verfahren zu ihrer Herstellung sowie ihrer Verwendung als reaktive Flammschutzmittel | |
| DE2448649C3 (de) | Verfahren zur Herstellung von aliphatischen oder cycloaliphatischen Diol-Polycarbonaten | |
| DE1132130B (de) | Verfahren zur Herstellung von flammfesten Phosphorverbindungen | |
| DE2901097B2 (de) | Den [5,5-Bis (methyl und/oder halogenmethyl) -2oxo-(oder -2- thio)-13,2-dioxaphosphorinanyloxymethyl] -Rest enthaltende substituierte Ester | |
| DE2507882A1 (de) | Verfahren zum herstellen von bis(trimethylsilyl-) harnstoff | |
| DE1643064A1 (de) | Verfahren zur Herstellung von halogensubstituierten und nichtsubstituierten Hydroxypolyalkoxyaminomethylphophinaten | |
| DE1795262A1 (de) | Waschfeste oelabweisende Ausruestung von Textilien | |
| DE1907402C3 (de) | Verfahren zur Herstellung phos phorhaltiger Polyepoxyde und deren Verwendung zur Textilveredlung | |
| DE2301789B2 (de) | Siloxan-polyoxyalkylen-blockmischpolymere, verfahren zu deren herstellung und verwendung | |
| DE2427879B2 (de) | Verfahren zur Herstellung von Phosphornitrilpolymerisaten und ihre Verwendung als feuerhemmende Mittel | |
| DE1745191B2 (de) | Verfahren zur herstellung von phosphorhaltigen polyolen | |
| DE2522693C2 (de) | Verfahren zur Herstellung von Bromarylphosphaten | |
| DE2559127A1 (de) | Bromierte carbamoylderivate, die zur flammfestigkeitsausruestung von verbrennbaren substraten nuetzlich sind | |
| DE2559128A1 (de) | Bromierte carbamoylderivate | |
| DE2013547C3 (de) | Verwendung von organischen Phosphorsiliciumverbindungen als flammhemmende Mittel | |
| DE2356034A1 (de) | Phosphor- und halogenhaltige polyole sowie verfahren zu deren herstellung | |
| DE2506599A1 (de) | Flammschutzmittel fuer polyurethan- schaumstoffe | |
| DE3643684A1 (de) | Verfahren zur herstellung von halogenierten phosphono-phosphorsaeureestern und ihre verwendung | |
| DE1745213C3 (de) | Verfahren zur Herstellung von chlorierten Polyhydroxypolyäthern und ihre Verwendung | |
| DE2233723A1 (de) | Polyalkylenglykol-alkylpolyphosphite |