IL40241A - The manufacture of phosphorus-containing condensation products,the products and their use as flameproofing agents - Google Patents
The manufacture of phosphorus-containing condensation products,the products and their use as flameproofing agentsInfo
- Publication number
- IL40241A IL40241A IL40241A IL4024172A IL40241A IL 40241 A IL40241 A IL 40241A IL 40241 A IL40241 A IL 40241A IL 4024172 A IL4024172 A IL 4024172A IL 40241 A IL40241 A IL 40241A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- tetrakis
- hydroxymethyl
- component
- phosphonium
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 14
- 239000007859 condensation product Substances 0.000 title claims 6
- 239000003795 chemical substances by application Substances 0.000 title claims 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 239000000047 product Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims 38
- -1 bicyclic dienes Chemical class 0.000 claims 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 239000000463 material Substances 0.000 claims 7
- 238000009833 condensation Methods 0.000 claims 6
- 230000005494 condensation Effects 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- 239000000835 fiber Substances 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- FAUOSXUSCVJWAY-UHFFFAOYSA-N tetrakis(hydroxymethyl)phosphanium Chemical class OC[P+](CO)(CO)CO FAUOSXUSCVJWAY-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 229920000728 polyester Polymers 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 229920003180 amino resin Polymers 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000001913 cellulose Substances 0.000 claims 2
- 229920002678 cellulose Polymers 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- 239000004744 fabric Substances 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 239000001117 sulphuric acid Substances 0.000 claims 2
- 235000011149 sulphuric acid Nutrition 0.000 claims 2
- IOIHFHNPXJFODN-UHFFFAOYSA-M tetrakis(hydroxymethyl)phosphanium;hydroxide Chemical compound [OH-].OC[P+](CO)(CO)CO IOIHFHNPXJFODN-UHFFFAOYSA-M 0.000 claims 2
- 239000008096 xylene Substances 0.000 claims 2
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- RDBMUARQWLPMNW-UHFFFAOYSA-N phosphanylmethanol Chemical class OCP RDBMUARQWLPMNW-UHFFFAOYSA-N 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 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
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
- D06M15/673—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain containing phosphorus and nitrogen in the main chain
-
- 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
- C07F9/54—Quaternary phosphonium 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
- C08G12/36—Ureas; Thioureas
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
-
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
- C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
- C08G16/0243—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/32—Modified amine-aldehyde condensates
-
- 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
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2240/00—Purpose of the treatment
- B27K2240/30—Fireproofing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Claims (9)
1. WHAT WE CLAIM IS: 1. Process for the manufacture of water-soluble condensation products of hydroxymethyl-phosphonium compounds and bicyclic dienes, characterised in that 1 raol of a tetrakis-(hydroxymethyl)-phosphonium compound is condensed with 0.02 to 1 mol of a 2 ,4 , 6 ,8 ,9-pentaazo-bicyclo- [3.3.1 ]-nona-2 , 6-diene of the formula HN - CH - N I I I I m HC NH CH J- ' i t I I N - CH - N - R or its salt; wherein R represents hydrogen or an optionally substituted aliphatic, cycloaliphatic , aromatic or heterocycl radical; at 40 to 120°C, optionally in the presence of formaldehyde or a formaldehyde-releasing agent and optionally in the presence of an inert organic solvent, the condensation then optionally continued at temperatures of 100 to 150°C and, if appropriate, free hydroxyl groups are etherified at least partially v/ith at least one alkanol with 1 to 4 carbon atoms.
2. Process according to Claim 1, characterised in that the condensation is carried out at 70 to 110°C.
3. Process according to Claim 1 or 2 , characterised in that the condensation is carried out in the presence of at least one inert aromatic hydrocarbon as the solvent.
4. Process according to Claim 3, characterised in that at least one xylene is used as the solvent.
5. Process according to one of Claims 1 to 4. characterised in that the two starting materials are condensed with one another in a molar ratio of 1:0.1 to 1:0.5. 6. Process according to one of Claims 1 to 5, characterised in that a tetrakis-(hydroxy-methyl)-phosphonium salt or tetrakis-(hydroxy-methyl)-phosphonium hydroxide is used. 7. Process according to Claim 6, characterised in that a tetrakis-(hydroxymethyl)-phosphonium salt is used. 8. Process according to Claim 7, characterised in that a tetrakis-(hydroxymethyl)-phosphonium halide is used. 9. Process according to Claim 8, characterised in that tetrakis-(hydroxymethyl)-phosphonium chloride is used. 10. Process according to one of Claims 1 to 9, characterised in that a bicyclic diene of the formula HN - CH - N (2) HC NH - CH tl I I N - CH - N - R is used, wherein denotes hydrogen, hydroxyl , alkyl , alkenyl, cycloalkyl, hydroxyalkyl, dialkylaminoalkyl , phenyl, hydroxy-phenyl, N-morpholyl-alkyl, pyridyl, pyrimidyl or piperazine-alkyl. 11. Process according to Claim 10, characterised in that a bicyclic diene of the formula HN - CH - N I It (4) HC NH CH II - CH - N - R is used, wherein R denotes alkyl with 1 or 2 carbon atoms or hydroxyalkyl with 1 or 2 carbon atoms or above all hydrogen, 12. Process according to one of Claims 1, 10 or 11, characterised in that the bicyclic diene is used as the salt of an allcylcarboxylic acid with 1 to 3 carbon atoms or as the salt of an inorganic acid. 13. Process according to Claim 12, characterised in that the bicyclic diene is employed as the salt of phosphoric acid, sulphuric acid or especially hydrochloric acid. 1 -Process according to one of Claims 1 to 13, characterised in that after completion of the reaction the salts of the condensation products are converted into the corresponding h3rdroxides. 15. The condensation products obtainable according to the process of one of Claims 1 to 1.4. 1.
6. Process for flameproofing organic fibre materials, characterised in that an aqueous preparation is applied to these materials which contains at least 1) a water-soluble condensation product of a hydroxymethyl-phosphonium compound and a bicyclic diene, which is obtained by condensing 1 mol of 'a tetrakis-(hydroxymethyl)-phosphonium compound with 0.02 to 0.1 mol of a 2 ,4,6,8,9-pentaazo-bicyclo-3.3.1 - nona-2,6-diene of the formula HN - Cll - H (1) ( 1 1 HC i CH II 1 II N - CH - N - R - - 40241/2 or its salt, wherein R represents hydrogen or an. optionally substituted aliphatic, cycloaliphatic , aromatic or heterocycli radical; at 40 to 120°C, optionally in the presence of formaldehyde or a formaldehyde-releasing agent and optionally in the presence of an inert organic solvent, optionally subsequently continuing the condensation at temperatures of 100 to 150°C and, if appropriate, etherifying free hydroxyl groups at least partially with at least one alkanol with 1 to 4 carbon atoms, and 2) a polyfunctional epoxide having- at least two epoxide groups which are derived from poly- hydric phenols or a polyalkylenepolyamine , an aminoplast- forming agent or an aminoplast precondensate , and the materials treated in this way are finished in accordance with the wet batch, moist batch, ammonia or thermofixing process . 1
7. Process according to Claim 16, characterised in that the treated materials are dried and subjected to a heat treatment. 1
8. Process' according to Claim 17, characterised in that when manufacturing the component (1) the condensation is carried out at 70 to 110°C. 1
9. Process according to Claim 17 or 18, characterised in that when manufacturing the component (1) the condensation is carried out in the presence of at least one inert aromatic hydrocarbon as the solvent. 20. Process according to Claim 19, characterised in that when manufacturing the component (1) at least one xylene is the two starting materials are condensed with one another in a molar ratio of 1:0.1 to 1:0.5. 22. Process according to one of Claims.17 to 21, characterised in that in the manufacturing process a tetrakis-(hydroxymethyl)-phosphonium salt or tetrakis-(hydroxymethyl)-phosphonium hydroxide is used. 23. Process according to Claim 22, characterised in that in the manufacturing process a tetrakis-(hydroxymethyl)-phosphonium salt is used. 24. Process according to Claim 23, characterised in that when manufacturing the component (1) a tetrakis-(hydroxymethyl)-phosphonium halide is used. 25. Process according to Claim 24, characterised in that when manufacturing the component (l) tetrakis-(hydroxymethyl).-phosphonium chloride is used. · . 26. Process according to one of Claims 17 to 25, characterised in that when manufacturing the component (1) a cyclic diene of the formula H - CH - N I l II (2) HC H CH II I I N - CH - N - RL is used, wherein R-j^ denotes hydrogen, hydroxyl, alkyl, alkenyl, cycloalkyl, hydroxyalkyl, dialkylaminoalkyl^ phenyl, hydroxy- phenyl, N-morpholyl-alkyl, pyridyl, pyrimidyl or piperazine- alkyl . 27. Process according to Claim 26, characterised in that when manufacturing the component (l) a bicyclic diene. of the formula TIN - Cll - N I I jl HC NH CH (A) II l I N - CH-N - R2 is used, wherein denotes alk l with 1 or 2 carbon atoms or hydroxyalkyl with 1 or 2 carbon atoms or above all hydrogen. 28. Process according to one of Claims 17, 26 or 27» characterised in that when manufacturing the component (1) the bicyclic diene is used as the salt of an alkylcarboxylic acid with 1 to 3 carbon atoms or as the salt of an inorganic acid. 29· Process according to Claim 28, characterised in that when manufacturing the component (1) the bicyclic diene is employed as the salt of phosphoric acid, sulphuric acid, or .especially of hydrochloric acid. 30. Process according to one of Claims 17 to 29, characterised in that when manufacturing the component (1), after completion of the reaction, the salts of. the condensation products are converted into the corresponding hydroxides. '31* Process according to Claim 17, characterised in that a polyfunctional nitrogen. compound is used as the component (2), 32. Process according to Claim 31, characterised in that an aminoplast-forming agent or an aminoplast precondensate is used as the component (2). 33. Process according to Claim 32, characterised in that a methylolurea or a methylolmelamine is used as the component (2). - 1 - 40241/2 34. Process according to one of Claims 17 to 33, characterised in that the fibre material of polyamides, cellulose, cellulose-polyester or polyester is flameproofed 35. Process according to Claim 34, characterised in that fabrics or mixed fabrics of polyester and cellulose are flameproofed . 36. Process according to one of Claims 16 to 35, characterised in that the fibre material is dried at tempera tures of up to 100°C and subjected to a heat treatment at'" above i00°C. 37. The organic fibre materials provided with a flameproof finish by the process according to one of Claims 16 to 36. 38. The aqueous preparations used for carrying out the process according to one of Claims 16 to 36.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH51972A CH547904B (en) | 1972-01-14 | 1972-01-14 | USE OF WATER-SOLUBLE, PHOSPHORUS CONTAINING CONDENSATION PRODUCTS TOGETHER WITH POLYFUNCTIONAL COMPOUNDS FOR FLAME RETAINING TEXTILE MATERIALS. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40241A0 IL40241A0 (en) | 1972-10-29 |
| IL40241A true IL40241A (en) | 1976-06-30 |
Family
ID=4188854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40241A IL40241A (en) | 1972-01-14 | 1972-08-29 | The manufacture of phosphorus-containing condensation products,the products and their use as flameproofing agents |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS4880894A (en) |
| AR (1) | AR195974A1 (en) |
| AT (1) | AT317835B (en) |
| AU (1) | AU470268B2 (en) |
| BE (1) | BE788593A (en) |
| CA (1) | CA997347A (en) |
| CH (2) | CH547904B (en) |
| CS (1) | CS161666B2 (en) |
| DE (1) | DE2242676A1 (en) |
| FR (1) | FR2167496B1 (en) |
| GB (1) | GB1402582A (en) |
| IL (1) | IL40241A (en) |
| IT (1) | IT965270B (en) |
| NL (1) | NL7212265A (en) |
| SU (1) | SU526296A3 (en) |
| ZA (1) | ZA725952B (en) |
-
0
- BE BE788593D patent/BE788593A/en unknown
-
1972
- 1972-01-14 CH CH51972A patent/CH547904B/en not_active IP Right Cessation
- 1972-01-14 CH CH51972D patent/CH51972A4/xx unknown
- 1972-08-29 IL IL40241A patent/IL40241A/en unknown
- 1972-08-30 DE DE2242676A patent/DE2242676A1/en active Pending
- 1972-08-30 ZA ZA725952A patent/ZA725952B/en unknown
- 1972-08-31 AU AU46192/72A patent/AU470268B2/en not_active Expired
- 1972-08-31 CA CA150,645A patent/CA997347A/en not_active Expired
- 1972-09-05 GB GB4110272A patent/GB1402582A/en not_active Expired
- 1972-09-06 SU SU1825121A patent/SU526296A3/en active
- 1972-09-07 FR FR7231665A patent/FR2167496B1/fr not_active Expired
- 1972-09-08 IT IT52624/72A patent/IT965270B/en active
- 1972-09-08 NL NL7212265A patent/NL7212265A/xx unknown
- 1972-09-08 AT AT772272A patent/AT317835B/en not_active IP Right Cessation
- 1972-09-08 CS CS6180A patent/CS161666B2/cs unknown
- 1972-09-08 AR AR243984A patent/AR195974A1/en active
- 1972-09-09 JP JP47090050A patent/JPS4880894A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU4619272A (en) | 1974-03-07 |
| CH51972A4 (en) | 1973-08-15 |
| FR2167496A1 (en) | 1973-08-24 |
| BE788593A (en) | 1973-03-08 |
| AU470268B2 (en) | 1976-03-11 |
| CH547904B (en) | 1974-04-11 |
| SU526296A3 (en) | 1976-08-25 |
| IT965270B (en) | 1974-01-31 |
| GB1402582A (en) | 1975-08-13 |
| CA997347A (en) | 1976-09-21 |
| ZA725952B (en) | 1973-06-27 |
| IL40241A0 (en) | 1972-10-29 |
| CS161666B2 (en) | 1975-06-10 |
| JPS4880894A (en) | 1973-10-29 |
| DE2242676A1 (en) | 1973-07-19 |
| AR195974A1 (en) | 1973-11-23 |
| AT317835B (en) | 1974-09-10 |
| FR2167496B1 (en) | 1974-12-06 |
| NL7212265A (en) | 1973-07-17 |
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