DE1794261B2 - USE OF CARBAMOYL-PHOSPHONIC ACID DIALKYLESTERS AS FLAME PROTECTION AGENTS FOR TEXTILE GOODS - Google Patents
USE OF CARBAMOYL-PHOSPHONIC ACID DIALKYLESTERS AS FLAME PROTECTION AGENTS FOR TEXTILE GOODSInfo
- Publication number
- DE1794261B2 DE1794261B2 DE19681794261 DE1794261A DE1794261B2 DE 1794261 B2 DE1794261 B2 DE 1794261B2 DE 19681794261 DE19681794261 DE 19681794261 DE 1794261 A DE1794261 A DE 1794261A DE 1794261 B2 DE1794261 B2 DE 1794261B2
- Authority
- DE
- Germany
- Prior art keywords
- carbamoyl
- phosphonic acid
- acid
- textile goods
- substances
- 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
- 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 title description 14
- 239000011814 protection agent Substances 0.000 title 1
- 150000002148 esters Chemical class 0.000 claims description 11
- 239000000126 substance Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 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
- 150000001875 compounds Chemical class 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 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 4
- 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
- 238000005470 impregnation Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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
- 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
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 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 group [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 group [Cl] ZAMOUSCENKQFHK-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
- 150000007513 acids Chemical class 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 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 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
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- 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
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- HZCDANOFLILNSA-UHFFFAOYSA-N Dimethyl hydrogen phosphite Chemical group COP(=O)OC HZCDANOFLILNSA-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
- 241000628997 Flos Species 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
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-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
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-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
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 150000001768 cations Chemical class 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
- 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
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 239000007788 liquid Substances 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
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax 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
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
R1-O CH2-O-R2 R 1 -O CH 2 -OR 2
in der die Reste Ri Alkylreste mit 1 bis 3 Kohlenstoffatomen, die gegebenenfalls durch Halogen substituiert sind, oder gemeinsam einen Alkylrest mit 2 oder 3 Kohlenstoffatomen, R2 Alkylreste mit 1 bis 3 Kohlenstoffatomen und A einen gegebenenfalls substituierten Alkylenrest mit ί bis 3 Kohlenstoffatomen bedeuten, als Flammschutzmittel für Textilgut.in which the radicals Ri are alkyl radicals with 1 to 3 Carbon atoms which are optionally substituted by halogen, or together one Alkyl radicals with 2 or 3 carbon atoms, R2 alkyl radicals with 1 to 3 carbon atoms and A denote an optionally substituted alkylene radical having ί to 3 carbon atoms, as a flame retardant for textile goods.
Die vorliegende Erfindung betrifft die Verwendung bestimmter Carbamoyl-Phosphonsäuredialkylester als Flammschutzmittel für Textilgut.The present invention relates to the use of certain carbamoyl phosphonic acid dialkyl esters as Flame retardants for textile goods.
Aus den belgischen Patentschriften 6 47 376 und 6 99 289 sind N-Monomethylol- und N-Monoalkoxymethylverbindungen von Carbamoylalkanphosphonsäuredialkylestern bekannt. Sie werden dott als Flammschutzmittel für Cellulose empfohlen. Es hat sich aber herausgestellt, daß sie einige Nachteile haben: optimale und vor allem auch waschpermanente Effekte erzielt man nur, wenn man sie zusammen mit .jminoplastbildenden Stoffen, wie sie für die Knitterfestausrüstung üblich sind, verwendet. Außerdem neigen sie dazu, auf dem mit ihnen behandelten Gut verhältnismäßig hohe Reißfestigkeitsverluste sowie eine Griffverhäritung zu verursachen.Belgian patents 6 47 376 and 6 99 289 disclose N-monomethylol and N-monoalkoxymethyl compounds of Carbamoylalkanphosphonsäuredialkylestern known. You will dott as Flame retardant recommended for cellulose. But it turned out that they have some disadvantages: Optimal and, above all, wash-permanent effects can only be achieved if you use them together with .jminoplast-forming materials, such as those used for anti-crease finishing are commonly used. In addition, they tend to be proportionate to the property treated with them to cause high losses of tear strength and hardening of the grip.
Es wurde nun gefunden, daß die geschilderten Nachteile nicht aultreten, wenn man Carbamoylphosphonsäuredialkylester der allgemeinen FormelIt has now been found that the disadvantages outlined do not occur when dialkyl carbamoylphosphonate the general formula
R1-O O 0R 1 -OO 0
Ml Il /Ml Il /
Ρ—A—C-NΡ — A — C-N
R1-OR 1 -O
CH5-O-R,CH 5 -OR,
(D(D
CH2-O-R2 CH 2 -OR 2
In der die Reste Ri 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 1 bis 3 Kohlenstoffatomen bedeuten, zum Flammfestmachen von Textilgut verwendet.In which the radicals Ri are 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 alkyl radicals with 1 to 3 carbon atoms and A is an optionally substituted alkylene radical having 1 to 3 carbon atoms, for Flame-proofing of textile goods used.
Von den Stoffen der Formel I haben wegen ihrer leichten Zugänglichkeit diejenigen eine besondere Bedeutung, in denen die Reste Ri 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.Of the substances of the formula I, some have a special one because of their easy accessibility Meaning in which the radicals Ri are unsubstituted or substituted by fluorine, chlorine or bromine, furthermore those in which the radicals R2 are methyl groups are, and finally those in which A is unsubstituted or by halogen, especially chlorine or bromine, or hydroxyl is substituted. Substances of the formula I in which A is an ethylene radical.
Beispiele für Stoffe der Formel 1 sind die
Ν,Ν-Dimethoxymethylverbindungen,
N,N-Diäthoxymethylverbindungenund
N1N- Dipropoxymethylverbindungen
des2-Carbamoyl-äthan-phosphonsäuredimethyl-Examples of substances of formula 1 are
Ν, Ν-dimethoxymethyl compounds,
N, N-diethoxymethyl compounds and
N 1 N-dipropoxymethyl compounds
des2-carbamoylethane phosphonic acid dimethyl
esters(H),
des2-Carbamoyl-äthan-phosphonsäure-esters (H),
des2-carbamoyl-ethane-phosphonic acid-
diäthylesters(HI),diethyl ester (HI),
des2-Carbamoyl-propan-phosphonsäuredi-des2-carbamoyl-propane-phosphonic acid-
methylesters(IV),methyl ester (IV),
des 2-Carbamoyl-1 -hydroxyäthan-phosphon-des 2-carbamoyl-1-hydroxyethane-phosphon-
säuredimethylesters (V),acid dimethyl ester (V),
desCarbamoylmethan-phosphonsäuredi-descarbamoylmethane phosphonic acid
[tribromäthylesters] (VI) und[tribromoethyl ester] (VI) and
des 2-Oxo-2-carbamcyläthyl-1,3,2-dioxa-des 2-oxo-2-carbamcylethyl-1,3,2-dioxa-
phospholans (VII).phospholans (VII).
CH3-O 0CH 3 -O 0
CH3-OCH 3 -O
25 P-CH2-CH2-C-NH2 25 P-CH 2 -CH 2 -C-NH 2
0 00 0
Jl IlJl Il
P-CH2-CH2-C-NH2 (ΠΙ)P-CH 2 -CH 2 -C-NH 2 (ΠΙ)
CH3-CH2-OCH 3 -CH 2 -O
CH3-O 0 CH3 OCH 3 -O 0 CH 3 O
CH3-OCH 3 -O
3535
40 P-CH2-CH-C-NH2 40 P-CH 2 -CH-C-NH 2
(IVi(IVi
CH3-O O OHCH 3 -OO OH
Ml I IiMl I Ii
P-CH-CH2-C-NH2 P-CH-CH 2 -C -NH 2
45 CH3-O
CBr3-CH2-O O 45 CH 3 -O
CBr 3 -CH 2 -OO
CBr3-CH2-OCBr 3 -CH 2 -O
CH2-O OCH 2 -OO
! \ll! \ ll
P-CH2-C-NH2 P-CH 2 -C-NH 2
(Vl)(Vl)
P-CH2-CH2-C-NH2 P-CH 2 -CH 2 -C-NH 2
(VII)(VII)
CH1-OCH 1 -O
Die Stoffe der Formel I können beispielsweise nach der DT-OS 17 93 514 hergestellt werden.The substances of the formula I can be prepared according to DT-OS 17 93 514, for example.
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 cellulosehaltigen! Textilgut außerdem eine sehr erwünschte Anhebung der Knittererholungswinkel. Für die Verwendung wird da« 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 bzw. oder potentiell sauren Kata'ysators mit den Stoffen derThe substances of the formula I can be used with outstanding success as flame retardants for textiles primarily for textiles that contain natural or regenerated cellulose or consists of it. They not only provide excellent flame retardancy, they also give up cellulosic! Textile goods also have a very desirable increase in the crease recovery angle. For the textile material to be treated is used 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 with the substances of the
Formel Ϊ umgesetzt Vorzugsweise wendet man dabei die Stoffe der Formel I in Form wäßriger Imprägnierbäder an; die Konzentration der Bäder an Stoffen der Formel I liegt im allgemeinen zwischen 250 und 500 g/l.Formula Ϊ implemented The substances of the formula I are preferably 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 Foulards. Das getränkte Gut befreit man in an sich bekannter Weise durch Abquetschen von überschüssiger Imprägnierflüssigkeit Man kann das imprägnierte Fasergut trocknen und es dann in Gegenwart saurer oder potentiell saurer Katalysatoren auf eine Temperatür bis zu 2000C, vorzugsweise auf 130 bis 170" C. erhitzen. Im allgemeinen ist unter diesen Bedingungen die Reaktion in 1 bis 6 Minuten beendetA padder is preferably used for the impregnation. The impregnated material is freed in a known manner by squeezing off excess impregnating liquid. The impregnated fiber material can be dried and then heated to a temperature of up to 200 ° C., preferably 130 to 170 ° C., in the presence of acidic or potentially acidic catalysts. In general, the reaction is complete in 1 to 6 minutes under these conditions
Saure oder potentiell saure Katalysatoren sind für die Zwecke der Ausrüstung mit N-Alkoxymethylverbindungen 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 bzw. 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 1 enthaltende Irnprägnierbad. 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 equipping with N-alkoxymethyl compounds known and used. Inorganic and organic ones, for example, come into consideration as such Acids such as sulfuric acid, hydrochloric acid, phosphoric acid, boric acid, oxalic acid, and salts that react or acidic the. for example by the action of heat and / or hydrolysis, acids during their use form, e.g. B. ammonium salts and amine salts, magnesium chloride, zinc chloride and zinc nitrate. Particularly good ones Flame retardant effects are achieved when using mono- and diammonium phosphate. The reaction the substances of the formula I with the textile material is, as mentioned, carried out in the presence of these catalysts This can be done by doing before or after the impregnation of the item to be treated with the new substances, the catalysts, preferably in the form of aqueous solutions, are applied to this. Preferably, however, the catalysts are added directly to the one containing the substances of the formula 1 Impregnation bath. In general, catalyst concentrations between 1 and 40 g / l proven.
Zusammen mit den Stoffen der Formel 1 können auch die bisher benutzten Hochveredelungsmittel, 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 Appretur-Mittel sowie Kunststofflösungen oder Kunststoffdispersionen rnitzuverwenden. Hydrophobiermittel sind z. B. die bekannten aluminium- oder zirkonhaltigen Paraffin-Wachs-Emulsionen sowie siliconhaltige Zubereitungen und perfluorierte aliphatische Verbindungen. Als Weichmachungsmittel seien z. B. Oxäthylierungsprodukte von höhermolekularen Fettsäuren, Fettalkoholen oder Fettsäureamiden, höhermolekulare Polyglykoläther und deren Ester, höhermolekulare Fettsäuren, Fettalkoholsulfonate, Stearyl-N,N-äthylenharnstoff und Stearylamidomethylpyridiniumchlorid genannt. Als Egalisiermittel können beispielsweise wasserlösliche Salze von sauren Estern mehrbasischer Säuren mit Äthylenoxid- oder Propylenoxidaddukten längerkettiger oxalkylierbarer Grundstoffe verwendet werden. Netzmittel sind beispielsweise Salze der Alkylnaphthalinsulfonsäuren, die Alkalisalze des sulfonierten Bernsteinsäuredioctylesters und die Anlagerungsprodukte von Alkylenoxiden an Fettalko-Alkvlühenole und Fettamine. Als Appreturmittel kommen beispielsweise Celluloseether oder Celluloseester und Alginate in Betracht außerdem Lösungen oder Dispersionen synthetischer Polymerisate, z. B. von Polyäthylen, Polyamiden, oxäihylierten Polyamiden, Polyvinyläthern, Polyvinylalkohole^ Polyacrylsäure oder deren Estern und Amiden sowie von entsprechenden Polymethacrylverbindungen, Polyvinylpropionat, Polyvinylpyrrolidon von Mischpolymerisaten, z. B. von solchen aus Acryl- oder NJethacrylsäureestern und wenigstens 20 Gewichtsprozent Acryl- und bzw. oder Methacrylsäure, aus Vinylchlorid und Acrylsäureester^ aus Butadien und Styrol bzw. Acrylnitril oder aus α-Dichlorethylen, /J-Chloralkylacrylsäureestern oder Vinyl-0-äthyläther und Acrylsäureamid oder den Amiden der Crotonsäure oder Maleinsäure oder aus N-Methylolmethacrylsäureamid und anderen polymerisierbaren Verbindungen.Together with the substances of Formula 1, the high-refinement agents previously used, for example the nitrogen-containing and also nitrogen-free hydroxymethyl or alkoxymethyl compounds of Urea, thiourea, cyclic ureas, such as ethylene urea, propylene urea, glyoxal monourein, Triazinones and urons, melamine and other aminotriazines, mono- and dicarbamic acid esters and polyethylene glycol formals and compounds containing epoxy groups, such as. B. Glycoldiglycidäther, be applied. It is also possible to use the customary hydrophobizing, softening, leveling, Use wetting agents and finishing agents as well as plastic solutions or plastic dispersions. Water repellants are z. B. the well-known aluminum or zirconium-containing paraffin wax emulsions as well preparations containing silicone and perfluorinated aliphatic compounds. As plasticizers are z. B. Oxäthylierungsprodukte of higher molecular fatty acids, fatty alcohols or fatty acid amides, higher molecular weight polyglycol ethers and their esters, higher molecular weight fatty acids, fatty alcohol sulfonates, Stearyl-N, N-ethyleneurea and stearylamidomethylpyridinium chloride called. Can be used as a leveling agent for example water-soluble salts of acidic esters of polybasic acids with ethylene oxide or propylene oxide adducts Longer-chain alkoxylatable base materials are used. Wetting agents are for example Salts of alkylnaphthalene sulfonic acids, the alkali metal salts of sulfonated dioctyl succinate and the Addition products of alkylene oxides with fatty alcohol alcohols and fatty amines. Cellulose ethers or cellulose esters, for example, can be used as finishing agents and alginates also consider solutions or dispersions of synthetic polymers, e.g. B. from Polyethylene, polyamides, oxyethylated polyamides, Polyvinyl ethers, polyvinyl alcohols ^ polyacrylic acid or their esters and amides as well as of corresponding polymethacrylic compounds, polyvinyl propionate, Polyvinylpyrrolidone of copolymers, z. B. of those made of acrylic or methacrylic acid esters and at least 20 percent by weight acrylic and / or methacrylic acid, from vinyl chloride and acrylic acid ester ^ from butadiene and styrene or acrylonitrile or from α-dichloroethylene, / J-chloroalkylacrylic acid esters or Vinyl-0-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 Links.
Nach der Reaktion der in den Stoffen der Formel I erhaltenen Gruppen hat das Textilgut einen ausgezeichneten und sehr wertbeständigen Flammschutz; außerdem hat das Fasergut auch ohne Mitverwendung der bisher üblichen Hochveredelungsmittel eine hohe Trocken- 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 the formula I, the textile material has an excellent one and flame retardant of very high value; in addition, the fiber material has also without the use of the hitherto customary high-quality finishing agents have a high freedom from dry and wet creases. The treated good can be washed, rinsed and dried in the usual way.
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 restrained to parts of space like the kilogram to the liter.
Ein Baumwollköper mit einem m2-Gewicht von 170 g wird in einer wäßrigen Flotte, die 375 g N,N-Dimethoxymethyl-carbamoyl-äthan-phosphonsäuredimethylester 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 bei 80 bis 100° C getrocknet und 5 Minuten bei 160 bis 165° C kondensiert. Zur Entfernung geringer Mengen nicht umgesetzter Reaktionsprodukte wäscht man anschließend mit einer wäßrigen Lösung, die 2 g Soda pro Liter enthält, bei 95°C 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 DlN 53 906 ergeben folgende Daten:A cotton twill with a m 2 weight of 170 g is treated in an aqueous liquor containing 375 g of N, N-dimethoxymethyl-carbamoyl-ethane-phosphonic acid dimethyl ester and 20 g of monoammon phosphate per liter of solution on a padder so that a liquor pick-up of approx. The result is 100% based on the weight of the textile. The fabric is dried at 80 to 100 ° C. and condensed at 160 to 165 ° C. for 5 minutes. To remove small amounts of unreacted reaction products, washing is then carried out with an aqueous solution containing 2 g of soda per liter 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 protection, which is retained even after several boil washes. The tests according to DIN 53 906 result in the following data:
Nach der Nach 10 Nach 20 Nach 30
Appli- Koch- Koch- Kochkation wäschen*)wäschen*)wäschen*)After After 10 After 20 After 30
Appli- Koch- Koch- Kochkation wash *) wash *) wash *)
*) 15 Minuten Waschen bei 950C in einer Flotte, die 1,5 g/l eines handelsüblichen Vollwaschmittels enthält.*) Wash for 15 minutes at 95 ° C. in a liquor which contains 1.5 g / l of a commercially available heavy-duty detergent.
375 Teile Ν,Ν-Dimethoxymethyl-carbamoyl-äthanphosphonsäuredimethylester, 30 Teile einer 45%igen, 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 behandelt375 parts of Ν, Ν-dimethoxymethyl-carbamoyl-ethanephosphonic acid dimethyl ester, 30 parts of a 45% aqueous solution of N, N'-dimethylol-4,5-dihydroxyethylene urea, 20 parts of monoammonium phosphate and 1 part of ammonium chloride are diluted to 1000 parts by volume with water. Treated with this solution
man Baumwollköper am Foulard so, daß eine Rottenaufnahme von ca. 100%, bezogen auf das Warengewicht resultiert Man trocknet bei 80 bis 1000C und kondensiert anschließend 5 Minuten bei 160 bis 165° C. Anschließend wird mit einer wäßrigen Lösung die 2 g/l Soda enthält, bei 95° C 3 Minuten lang gespült und 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: one cotton twill at the padder so that a gang pickup of about 100%, based on weight of resulting is dried at 80 to 100 0 C. and then condensed for 5 minutes at 160 to 165 ° C. Subsequently, with an aqueous solution containing 2 g / l contains soda, rinsed at 95 ° C for 3 minutes and dried again. The finished textile material shows excellent flame retardancy, which remains without loss of effectiveness even after numerous boil washes. If the finished fabric is tested in accordance with DIN 53 906, the following values are obtained:
Nach der Nach 10
Applikation Kochwäschen*) After the after 10
Application of hot washes *)
*) Bedingungen wie im Beispiel 1.*) Conditions as in example 1.
Ein Baumwollköper mit einem m2-Gewicht von 170 g wird in einer wäßrigen Flotte, die 450 N,N'-Diisoprop oxymethyl-earbamoyl-äthanphosphonsäurediisopropylester und 20 g Monoammonphosphat im Liter Lösung enthält, am Foulard so behandelt, daß eine Flüttenaufnahme von ca. 100%, bezogen auf das Textilgewicht, resultiert. Das Gewebe wird 6 Minuten bei 90 bis 100cC 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 95°C gewaschen. Nach Spülen und Trocknen zeigt das Gewebe einen hohen Flammschutz, der auch nach mehreren Kochwäschen erhalten bleibt. Die Prüfungen nach DIN 53 906 ergeben folgende Daten:A cotton twill with a m 2 weight of 170 g is treated on a padder in an aqueous liquor containing 450 N, N'-diisoprop oxymethyl-earbamoyl-ethanophosphonic acid diisopropyl ester and 20 g monoammon phosphate per liter of solution, so that a floss absorption of approx. 100%, based on the textile weight, results. The tissue is c 6 minutes at 90 to 100 C dried and condensed for 5 minutes at 165 0 C. The fabric is then washed at 95 ° C. for 3 minutes with a solution containing 2 g of soda per liter of water. After rinsing and drying, the fabric shows a high level of flame retardancy, which is retained even after several boil washes. The tests according to DIN 53 906 result in the following data:
Nach der
ApplikationAfter
application
Nach 10 Nach 20 Koch- KochAfter 10 After 20 Koch-Koch
wäschen*) waschen*)wash *) wash *)
450 Teile N.N-Dimethoxymethyl-carbamoyl-methan-phosphonsäure-di-[tribromäthylester] und 25 Teile Monoammonphosphat werden mit Wasser auf 1000· Raumteile verdünnt. Mit dieser Lösung behandelt man einen Baumwollköper am Foulard in der Weise, daß eine Flottenaufnahme von ca. 100%, bezogen auf das Textilgut, resultiert. Man trocknet bei 80 bis 100 C und kondensiert anschließend 5 Minuten bei 160 — 165 C. Das Gewebe wird mit einer wäßrigen Lösung, die 2 Teile Soda pro Liter enthält bei 95 C ca. 3 Minuten gewaschen und anschließend gespült und getrocknet. Die Flammschutzprüfung nach DlN 53 906 ergibt folgende Daten:450 parts of NN-dimethoxymethyl-carbamoyl-methane-phosphonic acid di- [tribromoethyl ester] and 25 parts of monoammonophosphate are diluted to 1000 parts by volume with water. A cotton twill is treated with this solution on a padder in such a way that a liquor pick-up of approx. 100%, based on the textile material, results. It is dried at 80 to 100 ° C. and then condensed for 5 minutes at 160-165 ° C. The fabric is washed with an aqueous solution containing 2 parts of soda per liter at 95 ° C. for about 3 minutes and then rinsed and dried. The flame protection test according to DIN 53 906 results in the following data:
Nach der Nach 10 Nach 20 Appli- Koch- KochAfter the After 10 After 20 Appli- Koch- Koch
kation waschen*) waschen*wash cation *) wash *
*) Bedingungen wie in Beispiel 1.*) Conditions as in example 1.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19681794261 DE1794261B2 (en) | 1968-09-28 | 1968-09-28 | USE OF CARBAMOYL-PHOSPHONIC ACID DIALKYLESTERS AS FLAME PROTECTION AGENTS FOR TEXTILE GOODS |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19681794261 DE1794261B2 (en) | 1968-09-28 | 1968-09-28 | USE OF CARBAMOYL-PHOSPHONIC ACID DIALKYLESTERS AS FLAME PROTECTION AGENTS FOR TEXTILE GOODS |
Publications (2)
Publication Number | Publication Date |
---|---|
DE1794261A1 DE1794261A1 (en) | 1971-10-07 |
DE1794261B2 true DE1794261B2 (en) | 1976-11-11 |
Family
ID=5707928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19681794261 Pending DE1794261B2 (en) | 1968-09-28 | 1968-09-28 | USE OF CARBAMOYL-PHOSPHONIC ACID DIALKYLESTERS AS FLAME PROTECTION AGENTS FOR TEXTILE GOODS |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE1794261B2 (en) |
-
1968
- 1968-09-28 DE DE19681794261 patent/DE1794261B2/en active Pending
Also Published As
Publication number | Publication date |
---|---|
DE1794261A1 (en) | 1971-10-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE2639754C3 (en) | Process for the production of curable condensation products and their use | |
EP0033115A2 (en) | Process for finishing textiles | |
DE1794261B2 (en) | USE OF CARBAMOYL-PHOSPHONIC ACID DIALKYLESTERS AS FLAME PROTECTION AGENTS FOR TEXTILE GOODS | |
DE1469269A1 (en) | Equipment for textile goods | |
DE3029537A1 (en) | COMPOSITION AND METHOD FOR PRODUCING A CROSS-SOLID FABRIC USING THIS COMPOSITION | |
EP0359039A2 (en) | Process for the wash-and-wear finishing of textiles | |
DE3041580C2 (en) | Water-soluble, oligomeric condensation product of glyoxal and cyclic urea and its use for the production of crease-resistant textiles | |
DE2312090A1 (en) | POLY-DIALKYLPHOSPHONOALKYLCARBONATES AND THEIR USE FOR FLAME PROTECTION EQUIPMENT OF CELLULOSIC TEXTILES | |
DE1469267C3 (en) | Use of hexahydropyrimidones as finishing agents for textiles | |
DE2707561C3 (en) | Agent for making polyester / cotton blended fabrics flame-retardant | |
DE2559126A1 (en) | BROMENED PHOSPHORAMIDATES | |
DE2114610A1 (en) | Derivatives of polyhydric alcohols | |
DE2808453A1 (en) | METHOD OF FLAME RETAINING FIBER CELLULOSIC MATERIAL | |
DE1938101A1 (en) | Process for the flame retardancy of cellulose-containing fabrics | |
DE1594954B1 (en) | Means and methods for making textiles crease-proof | |
DE2433372A1 (en) | Aminoplasts contg. dialkylphosphono-propylhexahydro-triazine - useful as flame retardants for textiles, esp. cellulosics | |
DE1594929C3 (en) | Process for refining fiber material containing or consisting of cellulose | |
DE1469269C (en) | Finishing agents for textile goods | |
DE1419364C (en) | ||
AT213834B (en) | Process for finishing textile fabrics | |
DE2024280A1 (en) | Anti-flame agent for textile material - com prising dialkoxyphos - phonoalkyl-carbamates | |
DE1469262A1 (en) | Process for refining fiber material containing or consisting of cellulose | |
DE1594941B1 (en) | Process for refining fiber material containing or consisting of cellulose | |
CH625070A5 (en) | High-speed printer with pneumatically actuated print head. | |
DE2331102A1 (en) | N- (DIALKYLPHOSPHONOALKYL) -CARBAMIC ACID ALKYLESTER |