DE1794261A1 - Carbamoyl-phosphonic acid dialkyl ester - Google Patents
Carbamoyl-phosphonic acid dialkyl esterInfo
- Publication number
- DE1794261A1 DE1794261A1 DE19681794261 DE1794261A DE1794261A1 DE 1794261 A1 DE1794261 A1 DE 1794261A1 DE 19681794261 DE19681794261 DE 19681794261 DE 1794261 A DE1794261 A DE 1794261A DE 1794261 A1 DE1794261 A1 DE 1794261A1
- Authority
- DE
- Germany
- Prior art keywords
- carbamoyl
- phosphonic acid
- acid
- substances
- formula
- 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
- 150000002148 esters Chemical class 0.000 title claims description 12
- VNVRRNRPVIZREH-UHFFFAOYSA-N carbamoylphosphonic acid Chemical compound NC(=O)P(O)(O)=O VNVRRNRPVIZREH-UHFFFAOYSA-N 0.000 title claims description 4
- 239000004753 textile Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000003063 flame retardant Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- -1 amine salts Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 238000005470 impregnation Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 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 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- 239000006012 monoammonium phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- STZBZWOIMFISKW-UHFFFAOYSA-N 3-diethoxyphosphorylpropanamide Chemical compound CCOP(=O)(OCC)CCC(N)=O STZBZWOIMFISKW-UHFFFAOYSA-N 0.000 description 1
- XMHCHCAKHCZBHU-UHFFFAOYSA-N 3-dimethoxyphosphoryl-2-methylpropanamide Chemical compound COP(=O)(OC)CC(C(=O)N)C XMHCHCAKHCZBHU-UHFFFAOYSA-N 0.000 description 1
- LSCSYJWMZUCJDW-UHFFFAOYSA-N 3-dimethoxyphosphorylpropanamide Chemical compound COP(=O)(OC)CCC(N)=O LSCSYJWMZUCJDW-UHFFFAOYSA-N 0.000 description 1
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- MBQCHFLAVBTBMA-UHFFFAOYSA-N COCN(C(=O)C(C)P(OC)(=O)OC)COC Chemical compound COCN(C(=O)C(C)P(OC)(=O)OC)COC MBQCHFLAVBTBMA-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- FFBZKUHRIXKOSY-UHFFFAOYSA-N aziridine-1-carboxamide Chemical compound NC(=O)N1CC1 FFBZKUHRIXKOSY-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical class CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- XAVCZNYPFYJSJJ-UHFFFAOYSA-N n-(pyridin-1-ium-1-ylmethyl)octadecanamide;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(=O)NC[N+]1=CC=CC=C1 XAVCZNYPFYJSJJ-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 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
- 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
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4816—Acyclic saturated acids or derivatices 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
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous 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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Carbamoyl-phosphonsäuredialkylester Die vorliegende Erfindung betrifft die Verwendung bestimmter Carbamoyl-phosphonsäuredialkylester als Flammschutzmittel fftr Textilgut. Carbamoyl-phosphonic acid dialkyl ester The present invention relates to the use of certain dialkyl carbamoyl phosphonates as flame retardants for textile goods.
Aus der belgischen PatentschriSt 647 376 sind N-Monomethylol-und N-Monoalkoxymethylverbindungen von Carbamoylalkanphosphonsäuredialkylestern bekannt. Sie werden dort als Flammschutzmittel fUr Cellulose empfohlen. Es hat sich aber herausgestellt, daß sie einige Nachteile haben: optimale Effekte erzielt man nur, wenn man sie zusammen mit aminoplastbildenden Stoffen, wie sie für die Knitterfestausrüstung üblich sind, verwendet. Außerdem neigen sie dazu, auf dem mit ihnen behandelten Gut verhältnismäßig hohe Reißfestigkeitsverluste zu verursachen.Belgian patent 647 376 describes N-monomethylol and N-monoalkoxymethyl compounds of Carbamoylalkanphosphonsäuredialkylestern known. They are there as a flame retardant recommended for cellulose. However, it has been found that they have some disadvantages have: optimal effects can only be achieved if they are used together with aminoplast-forming Fabrics such as those customary for the anti-crease finish are used. aside from that they tend to have relatively high losses in tensile strength on the goods treated with them to cause.
Es wurden nun neue Carbamoylphosphonsäuredialkylester gefunden, die die geschilderten Nahteile nicht haben. Die neuen Stoffe entsprechen aer allgemeinen Formel in der die Reste R1 Alkylreste mit 1 bis 3 Kohlenstoffatomen, die gegebenenfalls durch Halogen substituiert sind'oder gemeinsam einen Alkylenrest mit 2 - 3 Kohlenstoffatomen, R2 Alkylreste mit 1 bis 3 Kohlenstoffatomen und A einen gegebenenfalls substituierten Alkylenrest mit l bis 3 Kohlenstoffatomen bedeuten.New carbamoylphosphonic acid dialkyl esters have now been found which do not have the described near parts. The new substances correspond to the general formula in which the radicals R1 represent alkyl radicals with 1 to 3 carbon atoms, which are optionally substituted by halogen, or together an alkylene radical with 2-3 carbon atoms, R2 represents alkyl radicals with 1 to 3 carbon atoms and A is an optionally substituted alkylene radical with 1 to 3 carbon atoms.
Von den Stoffen der Formel 1 haben wegen ihrer leichten Zugänglichkeit diejenigen eine besondere Bedeutung, in denen die Reste R1 unsubstituiert oder durch Fluor, Chlor oder Brom substituiert sind, weiterhin diejenigen, in denen die Reste R2 Methylgruppen sind, und schließlich diejenigen, in denen A unsubstituiert oder durch Halogen, insbesondere Chlor oder Brom, oder Hydroxyl substituiert ist. Besonderes Interesse verdienen solche Stoffe der Formel I, in denen A ein Äthylenrest ist.From the fabrics of Formula 1 have because of their easy accessibility those of particular importance in which the radicals R1 are unsubstituted or by Fluorine, chlorine or bromine are substituted, continue those in which the radicals R2 are methyl groups, and finally those in which A is unsubstituted or is substituted by halogen, in particular chlorine or bromine, or hydroxyl. Special Substances of the formula I in which A is an ethylene radical are of interest.
Beispiele für Stoffe der Formel I sind die N,N-Dimethoxymethylverbindungen, N,N-Diäthoxymethylverbindungen und N,N-Dipropoxymethylverbindungen des 2-Carbamoyl-äthan-phosphonsäuredimethylesters (II), des 2-Carbamoyl-äthan-phosphonsäurediäthylesters (III), des 2-Carbamoyl-propan-phosphonsäuredimethylesters (IV), des 2-Carbamoy} ~l-hydroxySthan-phosphonsSuredimethylesters (V), des Carbamolymethan-phosphonsäuredi- [tribromäthylesters] (VX) und des 2-Oxo-2-carbamolyläthyl-1,3,2-dioxaphospholans (VII). Examples of substances of the formula I are the N, N-dimethoxymethyl compounds, N, N-diethoxymethyl compounds and N, N-dipropoxymethyl compounds of 2-carbamoyl-ethane-phosphonic acid dimethyl ester (II), 2-carbamoyl-ethane-phosphonic acid diethyl ester (III), des 2-carbamoyl-propane-phosphonic acid dimethyl ester (IV), of 2-carbamoy} ~ 1-hydroxy-thane-phosphonic acid dimethyl ester (V), of carbamolymethane-phosphonic acid di [tribromoethyl ester] (VX) and of 2-oxo-2-carbamolylethyl-1,3 , 2-dioxaphospholane (VII).
Die Stoffe der Formel I können beispielsweise nach Patent . ... ... (Anmeldung .. .. ....., interne Bezeichnung o.z. 25 809 eingereicht am 26.9.1968) hergestellt werden.The substances of the formula I can, for example, according to patent. ... ... (Registration .. .. ....., internal designation o.z. 25 809 filed on September 26, 1968) getting produced.
Die Stoffe der Formel I können mit hervorragendem Erfolg als Flammschutzmittel für Textilgut verwendet werden und zwar in erster Linie für Textilgut, das natürliche oder regenerierte Cellulose enthält oder daraus besteht. Sie geben dabei nicht nur einen ausgezeichneten Flammschutz, sondern bewirken auf cellulosehaltigem Textilgut außerdem eine sehr erwünschte Anhebung der Knittererholungswinkel. Für die Verwendung wird das zu behandelnde Textilgut in an sich bekannter Weise mit einem oder mehreren Stoffen der Formel 1 imprägniert und dann in Gegenwart wenigstens eines sauren und/oder potentiell sauren Katalysators mit den Stoffen der Formel 1 umgesetzt. Vorzugsweise wendet man dabei die Stoffe der Formel I in Form wässeriger Imprägnierbäder an; die Konzentration der Bäder an Stoffen der Formel I liegt im allgemeinen zwischen 250 und 500 g/l.The substances of the formula I can be used with outstanding success as flame retardants are used for textile goods, primarily for textile goods, the natural or contains or consists of regenerated cellulose. You're not just giving a excellent flame retardancy, but also have an effect on cellulosic textiles a very desirable increase in the crease recovery angle. For use will the textile material to be treated in a manner known per se with one or more Substances of formula 1 impregnated and then in the presence of at least one acidic and / or potentially acidic catalyst reacted with the substances of formula 1. Preferably if the substances of the formula I are used in the form of aqueous impregnation baths; the concentration of substances of the formula I in the baths is generally between 250 and 500 g / l.
Vorzugsweise bedient man sich für das Imprägnieren eines Foulard.A padder is preferably used for the impregnation.
Das getränkte Gut befreit man in an sich bekannter Weise durch Abquetschen von überschüssiger ImprSgnierfldssigkeit. Man kan das imprägnierte Fasergut trocknen und es dann in Gegenwart saurer oder potentiell saurer Katalysatoren auf eine Temperatur bis zu 2000C, vorzugsweise auf 130 bis 1700C, erhitzen. Im allgemeinen ist unter diesen Bedingungen die Reaktion in l bis 6 Minuten beendet.The soaked material is freed in a manner known per se by squeezing it off of excess impregnation fluid. The impregnated fiber material can be dried and then in the presence of acidic or potentially acidic catalysts to a temperature Heat up to 2000C, preferably to 130 to 1700C. Generally is under these conditions completed the reaction in 1 to 6 minutes.
Saure oder potentiell saure Katalysatoren sind für die Zwecke der Ausrüstung mit N-ÅlMoxymethylverbindungen bekannt und gebräuchlich. Als solche kommen beispielsweise in Betracht anorganische und organische Säuren, wie Schwefelsäure, Salzsäure, Phosphorsäure, Borsäure, Oxalsäure, und Salze, die sauer reagieren oder die, beispielsweise durch Hitzeeinwirkung und/oder Hydrolyse, während ihrer Verwendung Säuren bilden, z.B. Ammoniumsalze und Aminsalze, Magnesiumchlorid, Zinkchlorid und Zinknitrat. Besonders gute Flammschutzwirkungen werden bei Verwendung von Mono- und Diammoniumphosphat erreicht. Die Reaktion der Stoffe der Formel I mit dem Textilgut wird, wie erwähnt, in Gegenwart dieser Katalysatoren durchgeführt. Das kann man bewerkstelligen, indem man vor oder nach dem Imprägnieren des auszurüstenden Gutes mit den neuen Stoffen die Katalysatoren, vorzugsweise in Form wäßriger Lösungen, auf dieses aufbringt. Vorzugsweise gibt man aber die Katalysatoren unmittelbar -in das die Stoffe der Formel I enthaltende Imprägnierbad. Im allgemeinen haben sich für die Ausrüstung Katalysatorkonzentrationen zwischen 1 und 40 g/l bewährt.Acid or potentially acidic catalysts are for the purpose of Equipment with N-Ålmoxymethyl compounds known and used. Come as such for example, inorganic and organic acids, such as sulfuric acid, Hydrochloric acid, phosphoric acid, boric acid, oxalic acid, and salts that react or acidic which, for example by the action of heat and / or hydrolysis, during their use Forming acids, e.g. ammonium salts and amine salts, magnesium chloride, zinc chloride and Zinc nitrate. Particularly good ones Flame retardant effects are achieved when used achieved by mono- and diammonium phosphate. The reaction of the substances of the formula I. As mentioned, the textile material is carried out in the presence of these catalysts. This can be done by doing before or after the impregnation of the finish to be treated The catalysts, preferably in the form of aqueous solutions, are good news for the new substances, applies to this. Preferably, however, the catalysts are added directly the impregnation bath containing the substances of formula I. Generally have Tried and tested for finishing catalyst concentrations between 1 and 40 g / l.
Zusammen mit den Stoffen der Formel I können auch die bisher benutzten Hochveredlungsmittel, beispielsweise die stickstoffhaltigen und auch stickstofffreien Hydroxymethyl- oder Alkoxymethylverbindungen von Harnstoff, Thioharnstoff, cyclischen Harnstoffen, wie Äthylenharnstoff, Propylenharnstoff, Glyoxalmonourein, Triazinonen und Uronen, Melamin und anderen Aminotriazinen, Mono- und Dicarbamidsäureestern sowie Polyäthylenglykolformale und Epoxygruppen enthaltende Verbindungen, wie z.B. Glykoldiglycidäther, angewendet werden. Ferner ist es möglich, noch die üblichen Hydrophobier=, Weichmachungs-, Egalisier-, Netz- und Appreturmittel sowie Kunststofflösungen oder -dispersionen mitzuverwenden. Hydrophobiermittel sind z. B. die bekannten aluminium- oder zirkonhaltigen Paraffin-Wachs-Emulsionen sowie siliconhaltige Zubereitungen und perfluorierte aliphatische Verbindungen. Als Weichmachungsmittel seien z. B. OxSthylierungsprodukte von höhermolekularen Fettsäuren, Fettalkoholen oder Fettsäureamiden, höhermolekulare Polyglykoläther und deren Ester, höermolekulare Fettsäuren, Fettalkohlosulfonate, Stearyl-N,N-äthylenharnstoff und Stearylamidomethylpyridiniumchlorid genannt.Together with the substances of the formula I, those previously used can also be used Refinement agents, for example the nitrogen-containing and nitrogen-free ones Hydroxymethyl or alkoxymethyl compounds of urea, thiourea, cyclic Urea, such as ethylene urea, propylene urea, glyoxalmonourein, triazinones and urones, melamine and other aminotriazines, mono- and dicarbamic acid esters as well as polyethylene glycol formals and compounds containing epoxy groups, e.g. Glycol diglycid ether. It is also possible to use the usual Hydrophobic, softening, leveling, wetting and finishing agents as well as plastic solutions or dispersions to be used. Water repellants are z. B. the well-known aluminum or paraffin wax emulsions containing zirconia and preparations containing silicone and perfluorinated aliphatic compounds. As a plasticizer are z. B. Oxylation products of higher molecular weight fatty acids, fatty alcohols or fatty acid amides, higher molecular weight polyglycol ethers and their esters, higher molecular Fatty acids, fatty alcohol sulfonates, stearyl-N, N-ethylene urea and stearylamidomethylpyridinium chloride called.
Als Egalisiermittel können beispielsweise wasserldsliche Salze von sauren Estern mehrbasischer Säuren mit Äthylenoxid- oder Propylenoxidadukten längerkettiger oxalkylierbarer Grundstoffe verwendet werden. Netzmittel sind beispielsweise Salze der Alkylnaphthalinsulfonsäuren, die Alkalisalze des sulfonierten Bernsteinsäuredioctylesters und die Anlagerungsprodukte von Alkylenoxiden an Fettalkohole, Alkylphenole, Fettamine und dergleichen.Water-soluble salts of, for example, can be used as leveling agents acidic esters of polybasic acids with ethylene oxide or propylene oxide adducts longer-chain Alkoxylable base materials are used. Examples of wetting agents are salts the alkylnaphthalenesulfonic acids, the alkali salts of the sulfonated dioctyl succinate and the addition products of alkylene oxides with fatty alcohols, alkylphenols, fatty amines and the same.
Als Appreturmittel kommen beispielsweise Celluloseäther oder -ester und Alginate in Betracht, außerdem Lösungen oder Dispersionen synthetischer Polymerisate, z.B. von Polyäthylen, Polyamiden, oxäthylierten Polyamiden, Polyvinyläthern, Polyvinylalkoholen, Polyacrylsäure oder deren Estern und Amiden sowie von entsprechenden Polymethacrylverbindungen, Polyvinylpropionat, Polyvinylpyrrolidon, von Mischpolymerisaten, z.B. von solchen aus Acryl{- odpr Methacrylsäureestern und wenigstens 20 Gewichtsprozent Ac;rYl und/oder Methacrylsäure, aus Vinylchlorid und Acrylsäureest,ern' aus Butadien und Styrol bzw. Acrylnitril oder aus @-Dichoräthylen, ß-Chloralkylacrylsäureestern oder Vinyl-ß-äthyläther und Acrylsäureamid oder den Amiden der Crotonsäure oder Maleinsäure oder aus N-Methylolmethacrylsäureamid und anderen polymerisierbsren Verbindungen.Cellulose ethers or esters, for example, can be used as finishing agents and alginates into consideration, as well as solutions or dispersions of synthetic polymers, e.g. of polyethylene, polyamides, oxyethylated polyamides, polyvinyl ethers, polyvinyl alcohols, Polyacrylic acid or its esters and amides and of corresponding polymethacrylic compounds, Polyvinyl propionate, polyvinyl pyrrolidone, of copolymers, e.g. of such of acrylic or methacrylic acid esters and at least 20 percent by weight of Ac; rYl and / or Methacrylic acid, made from vinyl chloride and acrylic acid residue, made from butadiene and styrene or acrylonitrile or from @ -dichoroethylene, ß-chloroalkylacrylic acid esters or vinyl ß-ethyl ether and acrylic acid amide or the amides of crotonic acid or maleic acid or of N-methylol methacrylic acid amide and other polymerizable compounds.
Nach der Reaktion der in den Stoffen der Formel 1 erhaltenen Gruppen hat das Textilgut einen ausgezeichneten urd. sehr wertbeständigen Flammschutz; außerdem hat das Fasergut auch ohne Mitverwendung der bisher üblichen hochveredlungsmittel eine hohe-Troeken-und Naßknitterfreiheit. Das behandelte Gut kann in üblicher Weise gewaschen, gespUlt und getrocknet werden.After the reaction of the groups obtained in the substances of formula 1 the textile goods have an excellent urd. flame retardant of very high value; aside from that the fiber material also has without the use of the previously customary high-quality finishing agents one high dryness and freedom from wet creases. The treated goods can be washed in the usual way, rinsed and dried.
Die in den Beispielen genannten Teile und Prozente sind Gewichtseinheiten. Die Gewichtsteile verhalten sich zu Raumteilen wie das Kilogramm zum Liter.The parts and percentages given in the examples are weight units. The parts by weight are related to parts of space as the kilogram is to the liter.
Beispiel 1 Ein Baumwollköper mit einem m2-Gewicht von 170 g wird in einer wäßrigen Flotte, die 375 g N,N-Dimethoxymethyl-carbamoyl-äthanphosphonsäuredimethylester und 20 g Monoammonphosphat im Liter Lösung enthält, am Foulard so behandelt, daß eine Fottenaufnahme von ca. 100 % bezogen auf das Textilgewicht resultiert. Das Gewebe wird bei 80 bis 1000C getrocknet und 5 Minuten bei 160 bis 1650C kondensiert. Zur Entfernung geringer Mengen nicht umgesetzter Reaktionsprodukte wäscht man anschließend mit 2 g Soda pro Liter Wasser bei 95 0C ca. 3 Minuten. Anschließend wird gespült und getrocknet. Das so ausgerüstete Gewebe zeigt einen hohen Flammschutz, der auch nach mehreren Kochwäschen erhalten bleibt. Die Prüfungen nach DIN 53 906 ergeben folgende Daten: Nach der Nach 10x Nach 20x Nach 30x Applikation Koch- + Koch- + Kochwäschen wäschen wäschen Prüfzeit (sec) 6 6 6 6 Brennzeit (sec) O 0 0 0 Glimmzeit (sec) O 0 0 0 Einreißlänge(mm) 60 60 68 70 Belastung (g) 50 50 50 50 + 15 Minuten bei 950C; 1,5 g/L eines handelsüblichen Vollwaschmittels Beispiel 2 375 Teile N,N-Dimethoxymetyl-carbamoyl-äthan-phosphonsäuredi methylester, 30 Teile einer 45 algen, wäßrigen Lösung von N, N'-Dimethylol-4, 5-dihydroxyäthylenharnstoff, 20 Teile Monoammoniumphosphat und 1 Teil Ammoniumchlorid werden mit Wasser auf 1000 Raumteile verdünnt. Mit dieser Lösung behandelt man Baumwollköper am Foulard so, daß eine Flottenaufnahme von ca. Example 1 A cotton twill with a m2 weight of 170 g is in an aqueous liquor containing 375 g of N, N-dimethoxymethyl-carbamoyl-ethanophosphonic acid dimethyl ester and contains 20 g of monoammon phosphate per liter of solution, treated on a padder so that the result is a photo uptake of approx. 100% based on the weight of the textile. That Tissue is dried at 80 to 1000C and condensed for 5 minutes at 160 to 1650C. The product is then washed to remove small amounts of unreacted reaction products with 2 g soda per liter of water at 95 ° C. for about 3 minutes. It is then rinsed and dried. The fabric finished in this way shows a high level of flame retardancy, too remains after several washes. The tests according to DIN 53 906 result following data: After After 10x After 20x After 30x application Boiling + boiling + boiling wash washing test time (sec) 6 6 6 6 burning time (sec) O 0 0 0 glow time (sec) O 0 0 0 tear length (mm) 60 60 68 70 load (g) 50 50 50 50 + 15 minutes at 950C; 1.5 g / L of a commercially available heavy-duty detergent example 2,375 parts of N, N-dimethoxymethyl-carbamoyl-ethane-phosphonic acid dimethyl ester, 30 parts a 45 algae, aqueous solution of N, N'-dimethylol-4, 5-dihydroxyethylene urea, 20 parts of monoammonium phosphate and 1 part of ammonium chloride are made up to 1000 with water Diluted parts of the room. This solution is used to treat cotton twill on the foulard so that that a fleet pick-up of approx.
100 % bezogen auf das Warengewicht resultiert. Man trocknet bei 80 bis 1000C und kondensiert anschließend 5 Minuten bei 160 bis 1650C. Nach einer Naßbehandlung (3 Minuten mit 2 g/l Soda bei 950C, spülen) wird erneut getrocknet. Das ausgerüstete Textilmaterial zeigt einen ausgezeichneten Flammschutz, der selbst nach zahlreichen Kochwäschen ohne Wirkungsverlust verbleibt. Prüft man das ausgerüstete Gewebe nach DIN 53 906, so erhält man folgende Werte Nach der Nach 10 Applikation Kochwäschen Prüfzeit (sec) 6 6 Brennzeit (sec) O 0 Glimmzeit (sec) O 0 Einreißlänge (mm) 88 94 Belastung (g) 50 50 + Bedingungen wie im Beispiel 1 Beispiel 3 Ein Baumwollkörper mit einem m2-Gewicht von 170 g wird in einer wäßrigen Flotte, die 450 N,N-Diisopropoxymethyl-carbamoyl-äthanphosphonsäurediisopropylester und 20 g Monoammonphosphat im Liter Lösung enthält, am Foulard so behandelt, daß eine Flottenaufnahme von ca. 100 % bezogen auf das Textilgewicht, resultiert. Das Gewebe wird 6 Minute n bei 90 bis 1000C getrocknet und 5 Minuten bei 1650C kondensiert. Anschließend wird das Gewebe 3 Minuten mit einer Lösung, die 2 g Soda pro Liter Wasser enthält, bei 950C gewaschen. Nach Spülen und Trocknen zeigt das Gewebe einen hohen Flammschutz, der auch nach mehreren Kochwäschen erhalten bleibt.100% based on the weight of the goods results. Dry at 80 up to 1000C and then condenses for 5 minutes at 160 to 1650C. After a wet treatment (3 minutes with 2 g / l soda at 950C, rinse) is dried again. The equipped Textile material shows excellent flame retardancy, which even after numerous Cooked washes remain without loss of effectiveness. The finished tissue is checked DIN 53 906, the following values are obtained After the after 10 application Hot washes test time (sec) 6 6 burning time (sec) O 0 glow time (sec) O 0 tear length (mm) 88 94 Load (g) 50 50 + conditions as in Example 1 Example 3 A cotton body with a m2 weight of 170 g is in an aqueous liquor, the 450 N, N-diisopropoxymethyl-carbamoyl-ethanophosphonic acid diisopropyl ester and contains 20 g of monoammon phosphate per liter of solution, treated on a padder so that a liquor pick-up of approx. 100% based on the textile weight results. That Tissue is dried for 6 minutes at 90 to 1000C and condensed for 5 minutes at 1650C. Then the tissue is 3 minutes with a solution containing 2 g of soda per liter Contains water, washed at 950C. After rinsing and drying, the fabric shows one high flame protection, which is retained even after several washes.
Die Prüfungen nach DIN 53 906 ergeben folgende Daten: Nach der Nach 10 x @ Nch 20 x @ Applikation Kochwäschen Kochwäschen Prüfzeit (sec) 6 6 6 Brennzeit (sec) O 0 0 Glimmzeit (sec) O 0 0 Einreißlänge (mm) 70 69 72 Belastung (g) 50 50 50 Bedingungen wie im Beispiel l Beispiel 4 450 Teile N,N-Dimethoxymethyl-carbamoyl-methan-phosphonsäure-di-[tribromäthylester] und 25 Teile Monoammonphosphat werden mit Wasser auf 1 000 Raumteile verdünnt. Mit dieser Lösung behandelt man einen Baumwollkörper am Foulard 10, daß eine Flottenaufnahme von ca. 100 %, bezogen auf das Textilgut, resultiert. Man trocknet bei 80 bis 1000C und kondensiert anschließend 5 Minuten bei 160 -1650C. Das Gewebe wird mit 2 Teilen Soda pro Liter Wasser bei 95 0C ca. 3 Minuten gewaschen und anschließend gespült und getrocknet. Die Flammschutzprüfung nach DIN 53 906 ergibt folgende Daten: Nach der Nach 10 x + Nach 20 x + Applikation Kochwäschen Kochwäschen Prüfzeit (sec) 6 6 6 Brennzeit (sec) O 0 0 Glimmzeit (sec) O 0 0 Einreißlänge (mm) 78 76 75 Belastung (g) 50 50 50 + Bedingungen wie in Beispiel 1The tests according to DIN 53 906 result in the following data: After the after 10 x @ after 20 x @ application hot washes hot washes test time (sec) 6 6 6 burning time (sec) O 0 0 glow time (sec) O 0 0 tear length (mm) 70 69 72 load (g) 50 50 50 conditions as in example 1 Example 4 450 parts of N, N-dimethoxymethyl-carbamoyl-methane-phosphonic acid di- [tribromoethyl ester] and 25 parts of monoammonophosphate are diluted to 1,000 parts by volume with water. With this solution is treated a cotton body on the padder 10 that a liquor pick-up of approx. 100%, based on the textile material, results. It is dried at 80 to 1000C and then condensed for 5 minutes at 160-1650C. The fabric comes with 2 parts Soda was washed per liter of water at 95 ° C. for about 3 minutes and then rinsed and dried. The flame retardancy test according to DIN 53 906 results in the following data: After der After 10 x + After 20 x + application boiling washes boiling washes test time (sec) 6 6 6 Burning time (sec) O 0 0 Smoldering time (sec) O 0 0 Tear length (mm) 78 76 75 Load (g) 50 50 50 + conditions as in Example 1
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DE19681794261 DE1794261B2 (en) | 1968-09-28 | 1968-09-28 | USE OF CARBAMOYL-PHOSPHONIC ACID DIALKYLESTERS AS FLAME PROTECTION AGENTS FOR TEXTILE GOODS |
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DE19681794261 DE1794261B2 (en) | 1968-09-28 | 1968-09-28 | USE OF CARBAMOYL-PHOSPHONIC ACID DIALKYLESTERS AS FLAME PROTECTION AGENTS FOR TEXTILE GOODS |
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DE1794261B2 DE1794261B2 (en) | 1976-11-11 |
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