GB1011572A - Phosphorus-containing carboxylic acid amides - Google Patents
Phosphorus-containing carboxylic acid amidesInfo
- Publication number
- GB1011572A GB1011572A GB17563/63A GB1756363A GB1011572A GB 1011572 A GB1011572 A GB 1011572A GB 17563/63 A GB17563/63 A GB 17563/63A GB 1756363 A GB1756363 A GB 1756363A GB 1011572 A GB1011572 A GB 1011572A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- linked
- carbon atoms
- compounds
- alkylene
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- -1 polymethylene chain Polymers 0.000 abstract 14
- 125000002947 alkylene group Chemical group 0.000 abstract 10
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 6
- 229910052801 chlorine Inorganic materials 0.000 abstract 6
- 239000000460 chlorine Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- 125000001246 bromo group Chemical group Br* 0.000 abstract 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 3
- 125000004171 alkoxy aryl group Chemical group 0.000 abstract 3
- 125000005082 alkoxyalkenyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004122 cyclic group Chemical group 0.000 abstract 3
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- 229920003180 amino resin Polymers 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000000839 emulsion Substances 0.000 abstract 2
- 239000011953 free-radical catalyst Substances 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 229940080818 propionamide Drugs 0.000 abstract 2
- 239000004160 Ammonium persulphate Substances 0.000 abstract 1
- 239000004358 Butane-1, 3-diol Substances 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- UEKQGZQLUMSLNW-UHFFFAOYSA-N Propyl isome Chemical compound C1=C2C(C(=O)OCCC)C(C(=O)OCCC)C(C)CC2=CC2=C1OCO2 UEKQGZQLUMSLNW-UHFFFAOYSA-N 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 abstract 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000019395 ammonium persulphate Nutrition 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 abstract 1
- 235000019437 butane-1,3-diol Nutrition 0.000 abstract 1
- COXSXIJJRSUURN-UHFFFAOYSA-N butyl ethyl hydrogen phosphite Chemical compound CCCCOP(O)OCC COXSXIJJRSUURN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 abstract 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 abstract 1
- UFEXTSGOROFQJU-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite ethane-1,2-diol Chemical compound OP(O)OP(O)O.C(CO)O UFEXTSGOROFQJU-UHFFFAOYSA-N 0.000 abstract 1
- MRNMYEYVQAVFQZ-UHFFFAOYSA-N dimethyl 2-(diethoxyphosphorylmethyl)butanedioate Chemical compound CCOP(=O)(OCC)CC(C(=O)OC)CC(=O)OC MRNMYEYVQAVFQZ-UHFFFAOYSA-N 0.000 abstract 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical group [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
Classifications
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
- D06M15/43—Amino-aldehyde resins modified by phosphorus compounds
- D06M15/432—Amino-aldehyde resins modified by phosphorus compounds by phosphonic acids or 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
- C07F9/06—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
- C07F9/28—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
- C07F9/547—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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
Abstract
Compounds of the general formula (I): <FORM:1011572/C3/1> where R represents hydrogen, allyl, or an alkyl group of up to six carbon atoms; n is either 1, when X represents hydrogen, methyl or a -CH2CONHCH2OR group, or zero, when X represents a -CH2CONHCH2OR group; and R1 and R2 either each represent the same or different alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl, alkoxyalkenyl, aryl, alkoxyaryl or alkylene residues, which may be substituted by one or more chlorine and/or bromine atoms, the terminal valencies of such alkylene residues being linked to a group of Formula II: <FORM:1011572/C3/2> the free valency of which, if only one of R1 and R2 is alkylene, is linked to a further monovalent R1 or R2 residue, or R1 and R2 together represent a polymethylene chain containing from two to six carbon atoms, which may be linked to a second polymethylene chain containing two to six carbon atoms, via a spirocarbon, which polymethylene chains may be substituted by one or more chlorine and/or bromine atoms and/or methyl groups, the terminal valencies of the second polymethylene chain, if such be present, being linked to a group of Formula (II), and in which at least one of R, R1 or R2 is allyl may be polymerized using a free radical catalyst. The polymers may be used in flame-proofing cellulosic materials. In Example (XVII), N - hydroxymethyl - 3-(diallyloxyphosphinyl) propionamide is polymerized using ammonium persulphate as catalyst. Specifications 693,742 and 695,782 are referred to.ALSO:The invention comprises compounds of the general Formula I <FORM:1011572/C2/1> where R represents hydrogen, allyl, or an alkyl group of up to six carbon atoms; n is either 1, when X represents hydrogen, methyl or a -CH2CONHCH2OR group, or zero, when X represents a -CH2CONHCH2OR group; and R1 and R2 either each represent the same or different alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl, alkoxyalkenyl, aryl, alkoxyaryl or alkylene residues, which may be substituted by one or more chlorine and/or bromine atoms, the terminal valencies of such alkylene residues being linked to a group of Formula II <FORM:1011572/C2/2> the free valency of which, if, only one of R1 and R2 is alkylene, is linked to a further monovalent R1 or R2 residue, or R1 and R2 together represent a polymethylene chain containing from two to six carbon atoms, which may be linked to a second polymethylene chain containing two to six carbon atoms, via a spiro-carbon, which polymethylene chains may be substituted by one or more chlorine and/or bromine atoms and/or methyl groups, the terminal valencies of the second polymethylene chain, if such be present, being linked to a group of Formula II. Preparative methods include: (1) reacting corresponding -CHXCONH2 compounds with formaldehyde or a source thereof to give products in which R=H; (2) etherifying compounds in which R=H by reaction with an alcohol in the presence of acid; (3) reacting compounds of type (CH2=)n-CX1=CONHCH2OR, where X1 is as X except that when n=O, X1 is =CHCONHCH2OR, with an appropriate secondary phosphite; (4) introduction of halogen, e.g. by reacting 3-(diallyloxyphosphinyl)-propionamide with a polyhalomethane (e.g. trichloro-bromo-methane) in the presence of a free radical catalyst and then hydroxymethylating. A number of starting materials of type <FORM:1011572/C2/3> including compounds illustrating the alkylene, polymethylene chain and spiro aspects of R1 and R2, are prepared by reacting (CH2=)2-CX1-CONH2 and (R1O)(R2O)P(O)H or by the action of ammonia on esters of (R1O)(R2O)P(O)(CH2)nCH(COOH)2. n-Butyl ethyl phosphite and secondary phosphites derived from butane-1,3-diol/cyclic phosphite, cyclohexanol, neopentyl glycol (cyclic phosphite) pentaerythritol (cyclic diphosphite) and ethylene glycol (diphosphite) are prepared by means of PCl3 or transesterification. Dimethyl - 2 - (diethoxyphosphinylmethyl)-succinate and di-n-propyl - 2 - (diethoxy - phosphinyl) succinate are prepared from diethyl phosphite and dimethyl itaconate and di-n-propyl maleate respectively. N - (Allyloxymethyl) acrylamide is prepared from acrylamide, paraformaldehyde and allyl alcohol. Specifications 693,742 and 695,782 are referred to.ALSO:Compounds of the general formula I <FORM:1011572/D1-D2/1> where R represents hydrogen, allyl, or an alkyl group of up to six carbon atoms; n is either 1, when X represents hydrogen, methyl or a <FORM:1011572/D1-D2/2> group, or zero, when X represents a -CH2CONCH2 or group; and R1 and R2 either each represent the same or different alkyl, alkenl, cycloalkyl, cycloalkenyl, alkoxyalkyl, alkoxyalkenyl, aryl, alkoxyaryl or alkylene residues, which may be substituted by one or more chlorine and/or bromine atoms, the terminal valencies of such alkylene residues being linked to a group of formula II: <FORM:1011572/D1-D2/3> the free valency of which, if only one of R1 and R2 is alkylene, is linked to a further monovalent R1 or R2 residue, or R1 and R2 together represent a polymethylene chain containing from two to six carbon atoms, which may be linked to a second polemethylene chain containing two to six carbon atoms, via a spiro-carbon, which polymethylene chains may be substituted by one or more chlorine and/or chromine atoms and/or methyl groups, the terminal valencies of the second polymethylene chain, if such be present, being linked to a group of formula II, or polymer of uch compounds in which at least one of R, R1 and R2 is alkyl are used in flameproofing cellulosic materials. If only one -CONHCH2OR group is present in the compound, an aminoplast is also necessary, but this is optional if there are two or more -CONHCH2Or groups. A latent acid catalyst is preferably present. Suitable aminoplast include urea-formaldehyde, ethyleneurea-formaldehyde, melamine-formaldehyde and etherified melamine-formaldehyde resins. Cellulosic materials treated in examples are cotton, viscose and paper. Other substancess present in examples are Na1CO3, MgCl2, NH4H2PO4, mer emulsion, a polyethylene wax emulsion and a wetting agent derived from ethylene oxide. Specifications 693,742 and 695,782 are referred to.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE647376D BE647376A (en) | 1963-05-03 | ||
| GB17563/63A GB1011572A (en) | 1963-05-03 | 1963-05-03 | Phosphorus-containing carboxylic acid amides |
| CH553564A CH474540A (en) | 1963-05-03 | 1964-04-28 | Process for the preparation of phosphonamides |
| CH297667A CH474605A (en) | 1963-05-03 | 1964-04-28 | Use of phosphonamides to make cellulose-containing textile material flame-resistant |
| FR972541A FR1395178A (en) | 1963-05-03 | 1964-04-28 | New compounds containing phosphorus |
| DE1469281A DE1469281C3 (en) | 1963-05-03 | 1964-04-30 | Phosphonocarboxamides, processes for their preparation and their use for flame retardancy |
| US649396A US3381063A (en) | 1963-05-03 | 1967-05-11 | Cyclic phosphono-carboxylic amides |
| US649395A US3381062A (en) | 1963-05-03 | 1967-05-11 | Cyclic diphosphono-carboxylic amides |
| US646119A US3374292A (en) | 1963-05-03 | 1967-06-14 | Phosphono carboxamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17563/63A GB1011572A (en) | 1963-05-03 | 1963-05-03 | Phosphorus-containing carboxylic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1011572A true GB1011572A (en) | 1965-12-01 |
Family
ID=10097384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17563/63A Expired GB1011572A (en) | 1963-05-03 | 1963-05-03 | Phosphorus-containing carboxylic acid amides |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3374292A (en) |
| BE (1) | BE647376A (en) |
| CH (2) | CH474605A (en) |
| DE (1) | DE1469281C3 (en) |
| GB (1) | GB1011572A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0256191A1 (en) * | 1986-08-20 | 1988-02-24 | Dainippon Ink And Chemicals, Inc. | Fire retardant for woody materials |
| US4839099A (en) * | 1985-02-27 | 1989-06-13 | Dainippon Ink And Chemicals, Inc. | Fire-retardant for woody materials |
| AU642465B2 (en) * | 1990-03-01 | 1993-10-21 | Albright & Wilson Uk Limited | Flame retardant composition and method of use |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH625070A4 (en) * | 1970-04-27 | 1971-12-15 | ||
| US3699192A (en) * | 1970-10-20 | 1972-10-17 | U S Oil Co Inc | Phosphonium compounds |
| US3765837A (en) * | 1971-09-03 | 1973-10-16 | Burlington Industries Inc | Flame retardant finish for polyester/cotton blends |
| DE2253663A1 (en) * | 1972-11-02 | 1974-05-16 | Hoechst Ag | PHOSPHORUS COMPOUNDS CONTAINING AMIDE GROUPS AND THEIR USE AS FLAME PROTECTION AGENTS |
| US3903337A (en) * | 1974-04-04 | 1975-09-02 | Mitsui Toatsu Chemicals | Method for processing cellulose containing material to impart flame resistance |
| US4017462A (en) * | 1974-08-22 | 1977-04-12 | The United States Of America As Represented By The Secretary Of Agriculture | Treatment of organic textiles with adduct polymers and phenols |
| US4007318A (en) * | 1975-05-21 | 1977-02-08 | General Electric Company | Phosphorylated polystyrene and method for forming same |
| US4162279A (en) * | 1977-09-28 | 1979-07-24 | Stauffer Chemical Company | Phosphonoxycarboxamides |
| US4577013A (en) * | 1983-12-22 | 1986-03-18 | Ciba-Geigy Corporation | Ionically modified cellulose material, its preparation and its use |
| IL98728A0 (en) * | 1990-08-03 | 1992-07-15 | Pfersee Chem Fab | Flameproofing compositions containing phosphono compounds and organic acids |
| EP1935935A1 (en) * | 2006-12-20 | 2008-06-25 | Huntsman Textile Effects (Germany) GmbH | Compound for treating fibre materials |
| EP2133461A1 (en) | 2008-06-12 | 2009-12-16 | Huntsman Textile Effects (Germany) GmbH | Compound for treating fibrous material, in particular by the method of extraction |
-
0
- BE BE647376D patent/BE647376A/xx unknown
-
1963
- 1963-05-03 GB GB17563/63A patent/GB1011572A/en not_active Expired
-
1964
- 1964-04-28 CH CH297667A patent/CH474605A/en not_active IP Right Cessation
- 1964-04-28 CH CH553564A patent/CH474540A/en not_active IP Right Cessation
- 1964-04-30 DE DE1469281A patent/DE1469281C3/en not_active Expired
-
1967
- 1967-06-14 US US646119A patent/US3374292A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4839099A (en) * | 1985-02-27 | 1989-06-13 | Dainippon Ink And Chemicals, Inc. | Fire-retardant for woody materials |
| EP0256191A1 (en) * | 1986-08-20 | 1988-02-24 | Dainippon Ink And Chemicals, Inc. | Fire retardant for woody materials |
| AU642465B2 (en) * | 1990-03-01 | 1993-10-21 | Albright & Wilson Uk Limited | Flame retardant composition and method of use |
Also Published As
| Publication number | Publication date |
|---|---|
| US3374292A (en) | 1968-03-19 |
| CH474540A (en) | 1969-06-30 |
| CH474605A (en) | 1969-08-15 |
| CH297667A4 (en) | 1969-03-14 |
| BE647376A (en) | |
| DE1469281A1 (en) | 1969-05-08 |
| DE1469281B2 (en) | 1973-04-26 |
| DE1469281C3 (en) | 1973-11-22 |
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