EP0000024A1 - Produits oligomères phosphorés et leur utilisation comme apprêts textiles ignifugeants - Google Patents
Produits oligomères phosphorés et leur utilisation comme apprêts textiles ignifugeants Download PDFInfo
- Publication number
- EP0000024A1 EP0000024A1 EP78100036A EP78100036A EP0000024A1 EP 0000024 A1 EP0000024 A1 EP 0000024A1 EP 78100036 A EP78100036 A EP 78100036A EP 78100036 A EP78100036 A EP 78100036A EP 0000024 A1 EP0000024 A1 EP 0000024A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- iii
- acid
- anhydrides
- anhydride
- 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.)
- Granted
Links
- 239000004753 textile Substances 0.000 title claims abstract description 26
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 37
- 239000011574 phosphorus Substances 0.000 title claims description 36
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 21
- 239000000463 material Substances 0.000 title claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 144
- -1 alkylene carbonates Chemical class 0.000 claims abstract description 122
- 239000003063 flame retardant Substances 0.000 claims abstract description 56
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 42
- 230000002378 acidificating effect Effects 0.000 claims abstract description 26
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 21
- 150000003018 phosphorus compounds Chemical class 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 59
- 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 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 49
- 150000002148 esters Chemical class 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 41
- 239000007795 chemical reaction product Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 230000007935 neutral effect Effects 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 230000008034 disappearance Effects 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract description 4
- 150000005846 sugar alcohols Polymers 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 239000002243 precursor Substances 0.000 abstract description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 46
- 238000012360 testing method Methods 0.000 description 40
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 39
- 150000001298 alcohols Chemical class 0.000 description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
- 239000004744 fabric Substances 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- 229920001577 copolymer Polymers 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 16
- 239000000835 fiber Substances 0.000 description 16
- 229910052731 fluorine Inorganic materials 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000004952 Polyamide Substances 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 238000005470 impregnation Methods 0.000 description 15
- 229920002647 polyamide Polymers 0.000 description 15
- 229920000728 polyester Polymers 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 12
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000004743 Polypropylene Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 229920001155 polypropylene Polymers 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 235000020357 syrup Nutrition 0.000 description 8
- 241001136792 Alle Species 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 7
- 239000002453 shampoo Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- 0 C(C1)C2C1*CC2 Chemical compound C(C1)C2C1*CC2 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 239000003365 glass fiber Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 238000009732 tufting Methods 0.000 description 6
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical class OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 230000010354 integration Effects 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
- 125000004437 phosphorous atom Chemical group 0.000 description 4
- 229920002689 polyvinyl acetate Polymers 0.000 description 4
- 239000011118 polyvinyl acetate Substances 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- JHLVEBNWCCKSGY-UHFFFAOYSA-N tert-butyl n-methylcarbamate Chemical compound CNC(=O)OC(C)(C)C JHLVEBNWCCKSGY-UHFFFAOYSA-N 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- DGLXNOJGOHKWTN-UHFFFAOYSA-N CCCP(O)=O Chemical compound CCCP(O)=O DGLXNOJGOHKWTN-UHFFFAOYSA-N 0.000 description 3
- LKQYXBXRMPIGKC-UHFFFAOYSA-N CP(=O)OP(C)=O Chemical compound CP(=O)OP(C)=O LKQYXBXRMPIGKC-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 3
- 150000001733 carboxylic acid esters Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 3
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- OIPVVIVEDHZKCJ-UHFFFAOYSA-N 1-amino-2-methyltetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)(O)CN OIPVVIVEDHZKCJ-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 description 2
- NKFNBVMJTSYZDV-UHFFFAOYSA-N 2-[dodecyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCCCCCCCCCN(CCO)CCO NKFNBVMJTSYZDV-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 2
- JQALNNOQTGZTJZ-UHFFFAOYSA-N [[4,6-bis[bis(methoxymethyl)amino]-1,3,5-triazin-2-yl]-(methoxymethyl)amino]methanol Chemical compound COCN(CO)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 JQALNNOQTGZTJZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- OZCRKDNRAAKDAN-UHFFFAOYSA-N but-1-ene-1,4-diol Chemical compound O[CH][CH]CCO OZCRKDNRAAKDAN-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- KSHDLNQYVGBYHZ-UHFFFAOYSA-N dibutylphosphinic acid Chemical compound CCCCP(O)(=O)CCCC KSHDLNQYVGBYHZ-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- GOJNABIZVJCYFL-UHFFFAOYSA-N dimethylphosphinic acid Chemical compound CP(C)(O)=O GOJNABIZVJCYFL-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- RLDXWNAZJDJGCX-UHFFFAOYSA-N methoxy(propyl)phosphinic acid Chemical compound CCCP(O)(=O)OC RLDXWNAZJDJGCX-UHFFFAOYSA-N 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- SZTJCIYEOQYVED-UHFFFAOYSA-N methyl(propyl)phosphinic acid Chemical compound CCCP(C)(O)=O SZTJCIYEOQYVED-UHFFFAOYSA-N 0.000 description 2
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 2
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940005657 pyrophosphoric acid Drugs 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005406 washing Methods 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
- PMZIUAOBHNJYQT-UHFFFAOYSA-N (1-hydroxy-2-methylpropan-2-yl)azanium;chloride Chemical compound Cl.CC(C)(N)CO PMZIUAOBHNJYQT-UHFFFAOYSA-N 0.000 description 1
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- JHDJUJAFXNIIIW-UHFFFAOYSA-N (4-phosphonophenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=C(P(O)(O)=O)C=C1 JHDJUJAFXNIIIW-UHFFFAOYSA-N 0.000 description 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- YYZHSSQTEZXNGC-UHFFFAOYSA-N 1,2-bis(dimethoxyphosphoryl)ethane Chemical compound COP(=O)(OC)CCP(=O)(OC)OC YYZHSSQTEZXNGC-UHFFFAOYSA-N 0.000 description 1
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BJARHAPTVNQGJR-UHFFFAOYSA-N 1,4-bis(dimethoxyphosphoryl)butane Chemical compound COP(=O)(OC)CCCCP(=O)(OC)OC BJARHAPTVNQGJR-UHFFFAOYSA-N 0.000 description 1
- WGLYLHNRGWWZMW-UHFFFAOYSA-N 1-(2-hydroxypropylsulfanyl)propan-2-ol Chemical compound CC(O)CSCC(C)O WGLYLHNRGWWZMW-UHFFFAOYSA-N 0.000 description 1
- SBRBXWIDHBSVPD-UHFFFAOYSA-N 1-[butoxy(ethyl)phosphoryl]oxybutane Chemical compound CCCCOP(=O)(CC)OCCCC SBRBXWIDHBSVPD-UHFFFAOYSA-N 0.000 description 1
- NDOVQOUOLUHROS-UHFFFAOYSA-N 1-[butyl(dibutylphosphoryloxy)phosphoryl]butane Chemical compound CCCCP(=O)(CCCC)OP(=O)(CCCC)CCCC NDOVQOUOLUHROS-UHFFFAOYSA-N 0.000 description 1
- STJWVOQLJPNAQL-UHFFFAOYSA-N 1-[diethoxyphosphorylmethyl(ethoxy)phosphoryl]oxyethane Chemical compound CCOP(=O)(OCC)CP(=O)(OCC)OCC STJWVOQLJPNAQL-UHFFFAOYSA-N 0.000 description 1
- AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 description 1
- MBDJXHDBQNHQFE-UHFFFAOYSA-N 1-amino-2-methylhexan-2-ol Chemical compound CCCCC(C)(O)CN MBDJXHDBQNHQFE-UHFFFAOYSA-N 0.000 description 1
- LHHMNJZNWUJFOC-UHFFFAOYSA-N 1-chloro-2-[2-chloroethoxy(ethenyl)phosphoryl]oxyethane Chemical compound ClCCOP(=O)(C=C)OCCCl LHHMNJZNWUJFOC-UHFFFAOYSA-N 0.000 description 1
- CNGZUJQPNVPPCJ-UHFFFAOYSA-N 1-chloroethylphosphonic acid Chemical compound CC(Cl)P(O)(O)=O CNGZUJQPNVPPCJ-UHFFFAOYSA-N 0.000 description 1
- SBRSYHLTLPSIEC-UHFFFAOYSA-N 1-di(propan-2-yloxy)phosphoryl-2-methylpropane Chemical compound CC(C)CP(=O)(OC(C)C)OC(C)C SBRSYHLTLPSIEC-UHFFFAOYSA-N 0.000 description 1
- KEOJOAVYGLGAIM-UHFFFAOYSA-N 1-diethoxyphosphorylbutane Chemical compound CCCCP(=O)(OCC)OCC KEOJOAVYGLGAIM-UHFFFAOYSA-N 0.000 description 1
- RUIKOPXSCCGLOM-UHFFFAOYSA-N 1-diethoxyphosphorylpropane Chemical compound CCCP(=O)(OCC)OCC RUIKOPXSCCGLOM-UHFFFAOYSA-N 0.000 description 1
- YWDFOLFVOVCBIU-UHFFFAOYSA-N 1-dimethoxyphosphorylpropane Chemical compound CCCP(=O)(OC)OC YWDFOLFVOVCBIU-UHFFFAOYSA-N 0.000 description 1
- 150000005003 1-naphthylamines Chemical class 0.000 description 1
- BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
- QVKJYNWFUWKXFA-UHFFFAOYSA-N 2,3-dibromopropylphosphonic acid Chemical compound OP(O)(=O)CC(Br)CBr QVKJYNWFUWKXFA-UHFFFAOYSA-N 0.000 description 1
- OHJYHAOODFPJOD-UHFFFAOYSA-N 2-(2-ethylhexoxy)ethanol Chemical compound CCCCC(CC)COCCO OHJYHAOODFPJOD-UHFFFAOYSA-N 0.000 description 1
- QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical compound OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical compound CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- KLEJBTFNQBCCHP-UHFFFAOYSA-N 2-[2,3-dibromopropyl(2-hydroxyethoxy)phosphoryl]oxyethanol Chemical compound OCCOP(=O)(CC(Br)CBr)OCCO KLEJBTFNQBCCHP-UHFFFAOYSA-N 0.000 description 1
- ZJXLQVFSQIDDGT-UHFFFAOYSA-N 2-[2-(2-aminoethylamino)ethylamino]ethane-1,1,1,2,2-pentol Chemical compound NCCNCCNC(O)(O)C(O)(O)O ZJXLQVFSQIDDGT-UHFFFAOYSA-N 0.000 description 1
- BYACHAOCSIPLCM-UHFFFAOYSA-N 2-[2-[bis(2-hydroxyethyl)amino]ethyl-(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CCN(CCO)CCO BYACHAOCSIPLCM-UHFFFAOYSA-N 0.000 description 1
- PSDFYYGWUDGDCJ-UHFFFAOYSA-N 2-[ethoxy(methyl)phosphoryl]ethanol Chemical compound CCOP(C)(=O)CCO PSDFYYGWUDGDCJ-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- KXXHZVHYFQSELL-UHFFFAOYSA-N 2-diethoxyphosphorylethanol Chemical compound CCOP(=O)(CCO)OCC KXXHZVHYFQSELL-UHFFFAOYSA-N 0.000 description 1
- QZVZISMKIPIGBT-UHFFFAOYSA-N 2-dimethylphosphorylethanol Chemical compound CP(C)(=O)CCO QZVZISMKIPIGBT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- SKJLIATVTKHMNL-UHFFFAOYSA-N 2-methoxyethyl n,n-bis(hydroxymethyl)carbamate Chemical compound COCCOC(=O)N(CO)CO SKJLIATVTKHMNL-UHFFFAOYSA-N 0.000 description 1
- DDOAOFQKHIPFFJ-UHFFFAOYSA-N 2-methyl-1-methylphosphonoyloxypropane Chemical compound CC(C)COP(C)=O DDOAOFQKHIPFFJ-UHFFFAOYSA-N 0.000 description 1
- LFMAOMQWCSTELR-UHFFFAOYSA-N 2-methyl-2-oxo-1,2$l^{5}-oxaphospholan-5-one Chemical compound CP1(=O)CCC(=O)O1 LFMAOMQWCSTELR-UHFFFAOYSA-N 0.000 description 1
- HAEFDDOAYBQRGK-UHFFFAOYSA-N 2-methylpropylphosphonic acid Chemical compound CC(C)CP(O)(O)=O HAEFDDOAYBQRGK-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 150000005004 2-naphthylamines Chemical class 0.000 description 1
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 1
- XYJLPCAKKYOLGU-UHFFFAOYSA-N 2-phosphonoethylphosphonic acid Chemical compound OP(O)(=O)CCP(O)(O)=O XYJLPCAKKYOLGU-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 1
- RAVZRUBLUBGQNY-UHFFFAOYSA-N 3-dimethoxyphosphorylpropanenitrile Chemical compound COP(=O)(OC)CCC#N RAVZRUBLUBGQNY-UHFFFAOYSA-N 0.000 description 1
- AMKPQMFZCBTTAT-UHFFFAOYSA-N 3-ethylaniline Chemical compound CCC1=CC=CC(N)=C1 AMKPQMFZCBTTAT-UHFFFAOYSA-N 0.000 description 1
- OPWLEHJVKNPIRV-UHFFFAOYSA-N 3-hydroxypropyl(methyl)phosphinic acid Chemical compound CP(O)(=O)CCCO OPWLEHJVKNPIRV-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- SKIQWMHMYCHHOY-UHFFFAOYSA-N BrC(COP(OCC(CBr)Br)=O)CBr.OCC Chemical compound BrC(COP(OCC(CBr)Br)=O)CBr.OCC SKIQWMHMYCHHOY-UHFFFAOYSA-N 0.000 description 1
- FMFDHZZJAQDPEW-UHFFFAOYSA-N C(COP(=O)(C=CCl)OCCO)O Chemical compound C(COP(=O)(C=CCl)OCCO)O FMFDHZZJAQDPEW-UHFFFAOYSA-N 0.000 description 1
- WGDMNXBMFDAIKU-UHFFFAOYSA-N C.CP(=O)OP(C)=O Chemical compound C.CP(=O)OP(C)=O WGDMNXBMFDAIKU-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 101100476962 Drosophila melanogaster Sirup gene Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical class NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
- XUTKHJBIOLQTIN-UHFFFAOYSA-N [4-[hydroxy(methyl)phosphoryl]phenyl]-methylphosphinic acid Chemical compound CP(O)(=O)C1=CC=C(P(C)(O)=O)C=C1 XUTKHJBIOLQTIN-UHFFFAOYSA-N 0.000 description 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 1
- ULEMBJLJSDLKAF-UHFFFAOYSA-N [methoxy(methyl)phosphoryl]methanol Chemical compound COP(C)(=O)CO ULEMBJLJSDLKAF-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 150000005415 aminobenzoic acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AJGPQPPJQDDCDA-UHFFFAOYSA-N azanium;hydron;oxalate Chemical compound N.OC(=O)C(O)=O AJGPQPPJQDDCDA-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- PHIBEYMUALDAQI-UHFFFAOYSA-N benzylphosphinic acid Chemical compound OP(=O)CC1=CC=CC=C1 PHIBEYMUALDAQI-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- IAHMGMRQIFMUJX-UHFFFAOYSA-N bis(2,3-dibromopropoxy)-oxophosphanium Chemical compound BrCC(Br)CO[P+](=O)OCC(Br)CBr IAHMGMRQIFMUJX-UHFFFAOYSA-N 0.000 description 1
- NBXHFXZAURXGFL-UHFFFAOYSA-N bis(2-hydroxyethyl) 2,3-dibromobutanedioate Chemical compound OCCOC(=O)C(Br)C(Br)C(=O)OCCO NBXHFXZAURXGFL-UHFFFAOYSA-N 0.000 description 1
- XAVFZUKFLWOSOS-UHFFFAOYSA-N bis(dimethoxyphosphoryl)methane Chemical compound COP(=O)(OC)CP(=O)(OC)OC XAVFZUKFLWOSOS-UHFFFAOYSA-N 0.000 description 1
- CORRWSLEWBGTFG-UHFFFAOYSA-N butyl(methyl)phosphinic acid Chemical compound CCCCP(C)(O)=O CORRWSLEWBGTFG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- OHFQALRFLNKBNL-UHFFFAOYSA-N carbonic acid;ethanol Chemical compound CCO.OC(O)=O OHFQALRFLNKBNL-UHFFFAOYSA-N 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KTLIMPGQZDZPSB-UHFFFAOYSA-N diethylphosphinic acid Chemical compound CCP(O)(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- OIERWUPLBOKSRB-UHFFFAOYSA-N dimethoxyphosphorylmethanol Chemical compound COP(=O)(CO)OC OIERWUPLBOKSRB-UHFFFAOYSA-N 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- RQOKIVVUNQCMJS-UHFFFAOYSA-N dimethylphosphorylmethanol Chemical compound CP(C)(=O)CO RQOKIVVUNQCMJS-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- PATIESKUYYXOQY-UHFFFAOYSA-N dodecyl(methyl)phosphinic acid Chemical compound CCCCCCCCCCCCP(C)(O)=O PATIESKUYYXOQY-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- MEKDPHXPVMKCON-UHFFFAOYSA-N ethane;methane Chemical compound C.CC MEKDPHXPVMKCON-UHFFFAOYSA-N 0.000 description 1
- ZNBYZIRVKBMNRF-UHFFFAOYSA-N ethenyl(methyl)phosphinic acid Chemical compound CP(O)(=O)C=C ZNBYZIRVKBMNRF-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- YJCXKNNURGCXFQ-UHFFFAOYSA-N ethoxy(ethyl)phosphinic acid Chemical compound CCOP(O)(=O)CC YJCXKNNURGCXFQ-UHFFFAOYSA-N 0.000 description 1
- FJDJZPWIPLUDIZ-UHFFFAOYSA-N ethoxy(propyl)phosphinic acid Chemical compound CCCP(O)(=O)OCC FJDJZPWIPLUDIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- NXHKQBCTZHECQF-UHFFFAOYSA-N ethyl(methyl)phosphinic acid Chemical compound CCP(C)(O)=O NXHKQBCTZHECQF-UHFFFAOYSA-N 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000005165 hydroxybenzoic acids Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- 239000001282 iso-butane Substances 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
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- DWHMMGGJCLDORC-UHFFFAOYSA-N methoxy(methyl)phosphinic acid Chemical compound COP(C)(O)=O DWHMMGGJCLDORC-UHFFFAOYSA-N 0.000 description 1
- GSJFXBNYJCXDGI-UHFFFAOYSA-N methyl 2-hydroxyacetate Chemical compound COC(=O)CO GSJFXBNYJCXDGI-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- SXVDZIOMWSPFCO-UHFFFAOYSA-N methyl n,n-bis(hydroxymethyl)carbamate Chemical compound COC(=O)N(CO)CO SXVDZIOMWSPFCO-UHFFFAOYSA-N 0.000 description 1
- GKAMSGCCXBMNBH-UHFFFAOYSA-N methyl(octyl)phosphinic acid Chemical compound CCCCCCCCP(C)(O)=O GKAMSGCCXBMNBH-UHFFFAOYSA-N 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical compound CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ILCQYORZHHFLNL-UHFFFAOYSA-N n-bromoaniline Chemical class BrNC1=CC=CC=C1 ILCQYORZHHFLNL-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000005526 organic bromine compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical group C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 150000004995 p-toluidines Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 1
- CKVICYBZYGZLLP-UHFFFAOYSA-N pentylphosphonic acid Chemical compound CCCCCP(O)(O)=O CKVICYBZYGZLLP-UHFFFAOYSA-N 0.000 description 1
- NFBAXHOPROOJAW-UHFFFAOYSA-N phenindione Chemical class O=C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 NFBAXHOPROOJAW-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
- 150000004850 phospholanes Chemical class 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000008031 plastic plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- YOKDQEBPBYOXHX-UHFFFAOYSA-N prop-1-en-2-ylphosphonic acid Chemical compound CC(=C)P(O)(O)=O YOKDQEBPBYOXHX-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002023 somite Anatomy 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 208000006379 syphilis Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BVQJQTMSTANITJ-UHFFFAOYSA-N tetradecylphosphonic acid Chemical compound CCCCCCCCCCCCCCP(O)(O)=O BVQJQTMSTANITJ-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000008096 xylene 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
-
- 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
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl compounds
-
- 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
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
Definitions
- dialkyl phosphonic esters have already been converted into oligomeric phosphonic acid esters by the action of di-haloalkanes at temperatures around 180 ° C., which were optionally post-alkylated (US Pat. No. 3,956,431). This procedure usually results in methyl chloride or methyl bromide as undesirable by-products. Both are highly volatile toxic compounds that have to be absorbed - relatively cumbersome - for environmental reasons and thus make production considerably more difficult.
- the invention relates to mixtures (I) with a very wide range of variation with regard to their composition and their physical, chemical and flame-retardant properties, consisting of oligomeric phosphorus compounds of the general formulas I Z , I A , I K and I bo .
- B means "start” in terms of time
- E is “end” in terms of time
- A is "outside remainder”
- S is "pages” -Rest "and K is” Kern-Rest ".
- formula from only core anhydrides (K) and the oxyalkylating agents (IV) can be reheated to 100 ° to 200 ° C, preferably 130 ° to 170 ° C - optionally, for example in the presence of alkaline catalysts, preferably soda and / or aftertreatment with alkaline catalysts such as, for example preferably sodium methylate at temperatures from 0 ° to 100 ° C., preferably 20 ° to 60 ° C., largely destroyed and converted into substances of the types I Z , I A , I K and / or I bo .
- the moles of the compounds I Z are generally formulated for 1 to 6-valent alcohols.
- Z 1 -OH monohydric alcohols
- n 1
- b 1
- n 1
- II alcohols
- the 'process according to the invention is, if b> 0, is generally carried out in such a way that the phosphorus anhydrides of the formula III and additionally, if appropriate, volatile alkylene oxides (IV) or alkylene carbonates (IV 1 ), if used, are introduced at room temperature and slowly add the alcohol (II) at a temperature above the dissolving temperature. You can usually also add the alcohols (II).
- the reaction rates are significantly increased and side reactions suppressed.
- the reaction times are generally between about 1 and 120 hours, preferably 1 and 20 hours. They are naturally higher with increasing m, especially for m> 3 than for lower m.
- the chain can grow even further with other molecules of III and IV. If 1 + m is the total number of IV molecules used per growing chain, acids 1,2,3 4 etc. (generally 1 + m + q) are always formed when III q or one mole more than IV (generally 1 + m + q moles of III) to implement.
- Unsaturated alcohols are e.g. called: n-butene-2-ol-1, 1,4-butene diol and allyl alcohol, 1,4-butene diol being preferred as the dihydric alcohol.
- reaction products of ethylene oxide and / or ethylene carbonate with mono- or polyhydric alcohols there are also reaction products from mono- and polyhydric alcohols with other 1,2-alkylene oxides and / or 1,2-alkylene carbonates, such as especially 1,2-propylene oxide, 1, 2-propylene carbonate or epichlorohydrin, as well as the reaction products of ethylene oxide and / or ethylene carbonate with poly-1,2-propylene glycols which - as is known - are prepared as surface-active compounds in a wide range of variations.
- Corresponding poly-1,2-propylene glycols and corresponding adducts of ethylene oxide and / or ethylene carbonate with (poly) -1,2-propylene oxides are particularly worth mentioning.
- the hydrocarbon chain of aliphatic hydroxyl compounds can also be replaced by other heteroatoms, e.g. be interrupted by the elements N, S and / or P or carboxylic ester groups.
- These connections can e.g. particularly easily by reacting one or more molecules of 1,2-alkylene oxides and / or 1,2-alkylene carbonates with ammonia, primary or secondary amines, hydrogen sulfide, mercaptans and with oxygen acids of phosphorus, (C2-C6) carboxylic acids or dicarboxylic acids be preserved.
- n-butane isobutane, 2-ethyl-hexane, n-octane, decane, dodecane, tetradecane-phosphonic acid, but especially on methane, ethane, propane and vinylphosphonic acid and 1,2-ethane - or 1,4-butane-diphosphonic acid, furthermore to mono- or polyvalent dialkylphosphinic acids, such as Methyl-butyl-phosphinic acid, methyl-n-octyl-phosphinic acid, methyl-n-dodecyl-phosphinic acid and especially dimethyl-, ethyl-methyl-, methyl-propyl- and 1,10-decane-bis- (methyl-phosphinic acid) -, Methyl-vinyl-phosphinic acid, ethane-1,2-bis (methyl-phosphinic acid) and also reaction products of 1 to 7 moles of alkylene oxide or
- hydroxyl compounds with heteroatoms N, S and P which are very easily accessible through oxyalkylation reactions
- numerous other compounds with hydroxyl groups and optionally these heteroatoms and / or carboxylic ester groups in the hydrocarbon chain are suitable, of which only those are mentioned, for example oligo condensates which are formed by reaction of dicarboxylic acids or dicarboxylic acid anhydrides with polyhydric alcohols, also glycolic acid methyl ester, 2- ' hydroxyethane-carbonate, ethyl ester etc.
- hydroxymethane-phosphonic acid dimethyl ester 2-hydroxyethane-phosphonic acid diethyl ester, 3-hydroxypropane phosphonic acid di-n-butyl ester etc. and analogous compounds from the phosphinic acid series, such as, for example, methyl hydroxymethyl-methylphosphinate, ethyl 2-hydroxyethyl-methylphosphinate, 2'-ethylhexyl 3-hydroxypropyl-methylphosphinate, hydroxymethyl -dimethyl-phosphine oxide, 2-hydroxyethyl-dimethyl-phosphine oxide.
- a preferred position among the aromatic compounds is taken by all aromatic compounds with alcoholic hydroxyl groups, such as, for example, benzyl alcohol and all 2-hydroxyalkyl ethers or esters, which by oxalkylations of phenolic hydroxyl groups or of aromatic compounds which contain carboxylic acid, phosphonic acid or phosphinic acid residues , arise with compounds of formula IV or IV 1 .
- alcoholic hydroxyl groups such as, for example, benzyl alcohol and all 2-hydroxyalkyl ethers or esters, which by oxalkylations of phenolic hydroxyl groups or of aromatic compounds which contain carboxylic acid, phosphonic acid or phosphinic acid residues , arise with compounds of formula IV or IV 1 .
- aromatic mono- and Dicarboxylic acids such as benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, 1-naphthalene carboxylic acid, 2-naphthalene carboxylic acid, the carboxylic acids such as B. the three different hydroxy-benzoic acids, the different naphthol-carboxylic acids, 4,4'-diphenyl-dicarboxylic acid etc. into consideration.
- aromatic chlorine and especially bromohydroxy compounds can be of special interest, e.g. the oxyalkylation products of 2,4,6-iribromophenol, pentabromophenol, 2,4,6-irichlorophenol or pentachlorophenol and 2,2-bis (4-hydroxy-3,5-dibromophenyl) -propane.
- Aromatic phosphonic or phosphinic acids such as, for example, benzenephosphonic acid, 1,3- or 1,4-phenylene-diphosphonic acid, phenylmethylphosphinic acid, 1,3- or 1,4-phenylene-bis- (methyl- phosphinic acid) etc. previously converted into the corresponding 2-hydroxyalkyl esters by reaction with the 1,2-alkylene oxides (IV o ) and / or 1,2-alkylene carbonates (IV 1 ).
- Aromatic phosphonic or phosphinic acids such as, for example, benzenephosphonic acid, 1,3- or 1,4-phenylene-diphosphonic acid, phenylmethylphosphinic acid, 1,3- or 1,4-phenylene-bis- (methyl- phosphinic acid) etc. previously converted into the corresponding 2-hydroxyalkyl esters by reaction with the 1,2-alkylene oxides (IV o ) and / or 1,2-alkylene carbonates (IV 1 ).
- Suitable aromatic compounds with alcoholic hydroxyl groups can also be obtained by previous reactions of aromatic amines or mercapto compounds with 1,2-alkylene oxides and / or 1,2-alkylene carbonates.
- the suitable organic phosphoric anhydrides with the general formula III can have, depending on the special meanings R AB1 , R AB2 , r 1 , r 2 , A B , K , h , c K , c A and also R SB , R K , R 12 , f, g, s and i , be very diverse.
- the possibly additionally suitable compounds III CY therefore include, for example, the clearly cyclic phosphine-carboxylic acid anhydrides of the "phospholane type" (III PL ) such as 2-methyl, 2-ethyl, 2-n-propyl, 2-isobutyl, 2-vinyl, 2-chloromethyl, 2-phenyl, 2,3-dimethyl, 2-methyl 3-ethyl, 2-methyl-3-butyl, 2,4-dimethyl, 2-methyl-4-ethyl, 2-phenyl-4-methyl, 2,3,4-trimethyl, 2, 3,4-triethyl, and especially because of the easy accessibility 2-methyl-2,5-dioxo-1,2-oxa-phospholane.
- III PL the clearly cyclic phosphine-carboxylic acid anhydrides of the "phospholane type"
- the phospholanes (III PL ) must never be used as the sole core groups. At least one remainder K P must always be present. In order to be able to characterize the different types of real organic phosphoric anhydrides in a meaningful way, it is advisable to state the values of h, g and i as a subscript. The same applies to the connections from which they arise.
- the phosphonic anhydrides which are also suitable have the general formula and the characteristic III ho , g o , io .
- x here and in the following formulas represents the degree of polymerization which is unknown in the above formula. It is believed that these compounds are at room temperature partly as open (III OF ) and partly as cyclic anhydrides (III CY ).
- methane-phosphonic acid anhydride propane-phosphonic acid anhydride, n-butane-phosphonic acid anhydride, isobutane-phosphonic acid anhydride, n-pentane-phosphonic acid anhydride, chloromethane-phosphonic acid anhydride, 1- chloroethane-phosphonic acid anhydride, 2 - Chloroethane-phosphonic acid anhydride, 2,3-dibromo-propane-phosphonic acid anhydride, vinyl-phosphonic acid anhydride, propene-2-phosphonic acid anhydride, preferably methane-ethane, propane-phosphonic acid anhydride.
- R K can be either R AF1 , R SF or R AF2 .
- the metaphosphoric acid esters (III ho, go, i1 ) also contain cyclic structures (III CY ) in addition to open (III OF ). They are thermal, especially if R K is not CH3, far less stable than the phosphonic acid anhydrides. The higher esters decompose above 80 ° - 100 ° C with elimination of olefins. (See US 2 402 703 p. 1, column 1, line 14). The reaction with alcohols (II) and then with alkylene oxides (IV o ), however, proceeds smoothly, for example at 60-90 ° C.
- metaphosphoric acid isoamyl ester metaphosphoric acid n-butyl ester, metaphosphoric acid n-propyl ester, metaphosphoric acid ethyl ester and metaphosphoric acid methyl ester are suitable as compounds III EC from the corresponding trialkyl phosphates (KED fo, r1, s1 ) and phosphorus pentoxide.
- Such true mixed anhydrides are thermally as unstable as the metaphosphoric esters because of the ester residues they contain - especially when R is not CH 3 - above 80 ° C. Nevertheless, they are made from 1 mol of phosphorus pentoxide and from, for example, 1 mol of n-butane-phosphonic acid diethyl ester, isobutane-phosphonic acid di-isopropyl ester, n-propane-phosphonic acid diethyl ester, n-propane-phosphonic acid bis- (2-chloroethyl ester) ), dimethyl n-propane-phosphonate, di-n-butyl ethane-phosphonate, diethyl ethane-phosphonate, dimethyl 2-cyano-ethane-phosphonate, bis- (2,3-dibromopropyl) -phosphonate ), Methanephosphonic acid dimethylester etc.
- suitable 1,10-decane-bis- (methyl-phosphinic acid) anhydride 1,6-hexa-n-bis- (ethyl-phosphinic acid) anhydride, 1,4-butane bis- (methyl-phosphinic acid) anhydride , 1,2-ethane bis (methyl phosphinic acid) anhydride and methane bis (methyl phosphinic acid) anhydride.
- Suitable Off g angsester type KED f1, r1, s1 are for example 1,6-Hexandi-phosphonic tetraäthylester, 1,4-butane-di-phosphonic acid tetramethylester, 1,2-ethane-di-phosphonic acid tetraäthylester, 1, 2-ethane-di-phosphonic acid tetramethyl ester etc. and preferably methane-di-phosphonic acid tetra-ethyl ester and methane-di-phosphonic acid tetramethyl ester.
- 1,6-hexane-bis- methyl-phosphinic acid-isobutyl ester
- 1,2-ethane-bis-methyl-phosphinic acid-n-butyl ester 1,2-ethane-bis- (methyl ethyl phosphinate), ethyl methanephosphate) etc.
- AD H proton-containing outer group donors
- EC is the equivalent number of anhydride equivalents of real anhydrides used (III EC )
- HAZ ADH the hydrogen equivalent number of proton-containing outer group donors (AD H )
- HAZ ADH 1 to c K
- EC hydrogen equivalents of proton-containing outer group donors (AD H ) are added to the real anhydrides III EC .
- AD F proton-free outer group donors
- the phosphorus pentoxide dissolves more and more poorly in the core ester donors (KED F ) the closer the molar ratio approaches the limit value 1.0, since the viscosity also increases significantly.
- the MV range preferred in practice is therefore not 1.0, but beica. 1.05 to 1.50, or at c K values from 60 to 6.
- such mixtures of P 2 0 5 and the core ester donors (KED F ) should be heated to about 60-90 ° C.
- III AG, F proton-free closed organic phosphoric anhydrides
- reaction of compounds II, III and IV can be carried out at relatively low temperatures (approx. ⁇ 100 ° C) primary if necessary partly the hydroxyl g rupp free undesirable cyclic diesterartigen reaction products of type (K IV) formed.
- the corresponding desired reaction compounds (I) result from the ring opening, chain extension and increase in the m-value - recognizable by the disappearance of the corresponding bands, reduction in water sensitivity and increase in viscosity. But even minor residues of cyclic diesters (K IV )) still present in the end product (I) practically do not impair the usability of the end reaction mixtures (I), since anyway for fixing the end compounds (I) to textile material with the aid of, for example, aminoplast precondensates acidic pH values must be available. The aftertreatment can therefore, but does not have to be carried out in all cases.
- the organic phosphoric anhydrides (III) and the intermediate and final reaction products available from them have different thermal resistance. Whenever the indices r, s and above all s are 1 and R AB and R SB are not hydrogen, at higher temperatures Side reactions occur. Therefore, the use of alkylene oxides (IV 0 ) is recommended in such cases, since these generally react at lower temperatures than the alkylene carbonates (IV 1 ). Alkylene carbonates (IV 1 ) are advantageously used above all when high-melting or higher molecular weight alcohols (II) are used, for safety reasons, for example with ethylene oxide trolls (CO 2 development) is desired.
- inert solvents or diluents are not necessary. However, e.g. Acetone, methyl ethyl ketone, acetonitrile, 1,2-dichloroethane, benzene, toluene, xylene, chlorobenzene, but especially dioxane if necessary - added without damage as a diluent or solubilizer and still e.g. be removed by distillation before the complete reaction with the oxyalkylating agents (IV) or only at the end of the reaction.
- the reaction temperatures between the compounds II (b> 0) and .III are between 0 ° and 180 ° C or higher, for example up to 250 ° C, preferably between 20 ° and 150 ° C, in particular 80 ° to 150 ° C.
- the alkylene oxides (IV 0 ) react between 20 ° and 240 ° C, preferably 60-180 ° C.
- the reaction can be carried out in stages in such a way that if b> 0 is, initially b moles of alcohols.
- (II) with n alcoholic groups with b ⁇ n + e anhydride equivalents of the phosphorus anhydrides (III) and then initially at e 0 only b ⁇ n, at e 7 0 at least b ⁇ n + e moles of the oxyalkylating agent (IV) act until the acid number has dropped to practically 0.
- alkylene carbonates (IV 1 ) the compounds IV can be added to the mixtures of II and III from the start.
- low-volatile alkylene oxides (IV 0 ) such as epichlorohydrin.
- Volatile alkylene oxides (IV 0 ) such as propylene oxide or ethylene oxide, on the other hand, are dropped or gassed at the reaction temperatures.
- b 0 and e> 0, that is to say proton-containing closed phosphoric anhydrides (III AG, H ) but no alcohols (II) are used. However, the implementation of II and III is then omitted.
- the end products (I) are colorless or more or less yellowish in color and of different consistency.
- the compounds with long alkyl groups (up to 18 carbon atoms) can also be considered as surfactants because of their surface-active properties.
- the alcohols (II) were added to the anhydrides (III) at room temperature (25 ° C.) or at the liquefaction temperatures of any solid anhydrides (III), if appropriate with cooling, within 1 ' to 30 minutes.
- the specified different reaction conditions therefore always relate only to the reaction in the second stage with the oxyalkylating agents (IV).
- Examples 1-9, 10b, 15, 19 describe the direct method (DV), 20 the multi-stage process (MSV).
- the manufacturing examples 10a, 11-14, 16-18, in which b 0 and e> 0, respectively, explain the one-step process (EV).
- the phosphorus-containing polyadducts according to the invention which are distinguished by a very good water solubility or by a good emulsifiability and have a high phosphorus content, can be fixed on textile material with a wide variety of reactive crosslinking agents.
- the equipment obtained in this way has very good flame-retardant and permanent properties.
- Polyfunctional N-methylol compounds are suitable as crosslinking agents, e.g. Derivatives of amino-1,3,5-triazines, such as trimethylolmelamine, hexamethylolmelamine, trimethylolmelamine trimethyl ether, hexamethylolmelamine pentamethyl ether, trimethylolmelamine triisobutyl ether, dimethylol-aceto-guanamine, furthermore derivatives of ureas such as dimethylol urea, dimethyl methyl urethane, dimethyl methyl urethane, dimethyl methyl urethane, dimethyl methyl urethane 4-methoxy-5-dimethylpropyleneurea, dimethylol-5-hydroxypropyleneurea, 1,3-dimethylol-4,5-dihydroxy-imidazolidone- (2), 1,3-dimethylol-5-hydroxy-ethylhexahydrotriazine (2), dimethyloluron and Dimethylol carb
- melamine derivatives e.g. Trimethylolmelamine trimethyl ether or hexamethylol melamine pentamethyl ether.
- inorganic or organic acids or their salts which are added as catalysts which show their action in the acidic pH range Hydrolysis or by heat treatment release acid, such as sulfuric acid, hydrochloric acid, phosphoric acid, trichloroacetic acid, maleic acid, tartaric acid, citric acid, acetic acid or its salts with ammonia, amines or polyvalent metals, preferably salts of strong or medium strength acids, such as ammonium sulfate, ammonium chloride , Mono- and diammonium oxalate, ammonium nitrate, magnesium chloride, aluminum chloride, zinc chloride, zinc nitrate, zinc fluoroborate, 2-amino-2-methyl-propanol hydrochloride
- the crosslinking catalysts can be used alone or in mixtures with one another.
- the textile material on which the flame-retardant and permanent finishes are possible can be varied. Excellent flame retardant effects are achieved on cellulose fiber fabrics, polyester and polyamide fabrics, plastic-bonded or reinforced glass fiber fabrics, on textile wallpapers or textile blinds made of cellulose fibers, polyester or polyamide fibers, glass fibers or their mixtures.
- Particularly suitable as synthetic or mixed fiber goods are non-woven fabrics, e.g. Needle felts for wall and floor coverings, textile wallpapers, insulation materials and air filters of various types, such as. e.g.
- the process according to the invention for flame-retardant finishing of the textile goods described above is carried out under application conditions which are known and customary in the textile industry. An additional operation which rbeitsab- the A changed course of the finishing of the said textile material, is not necessary.
- the fabrics or needle felts are treated with the aqueous finishing liquors on a two-roll or three-roll pad, squeezed off and subjected to a drying or a condensation process.
- the heat is preferably applied in two stages. Initially is dried above about 50 ° C, preferably at about 100 0 to 120 0 C, to the water to a residual value of about 4-8% to be removed, and then leaves the Kon densation at about 140 ° to 180 0 C for about 7 to 3 minutes.
- the flame-retardant finishing of needle felt covers can also be carried out according to the two-stage process.
- the crosslinking is preferably carried out here in a one-stage drying or condensation process at approximately 120 ° to approximately 180 ° C., predominantly at 135 ° to 160 ° C.
- the heat treatment takes on average approximately 7 to approximately 60, preferably 10 to 30 minutes.
- the heat is applied in drying chambers, on tenter frames, yard lues or condensation frames.
- finishing agents such as textile softeners, water repellent products, oleophobicizing products or even antimicrobial finishing products can be added to the finishing liquors.
- the very good flame retardant effects of the claimed organophosphorus compounds allow pile rugs - woven or tufted rugs - to be applied over the back of the carpet or over the primer.
- the carpet backing equipment for woven carpets is known to be responsible for the dimensional stability and the primer for the integration of the pile threads in the tufting base fabric.
- Anchoring the organophosphorus compounds in the carpet backing or in the primer makes a full bath impregnation unnecessary.
- the pile threads are also brought into contact with the flame retardants, crosslinkers, catalysts and binders based on plastic dispersions.
- the flame retardants and the other finishing products of the impregnation liquor then lie on or between the pile threads and lead to adhesions.
- the individual thread of the pile should remain flexible.
- gluing the pile can lead to increased dirt absorption.
- the flame retardant products can also be stepped out gradually when walking on the carpets.
- the pile carpets finished in this way are also characterized by their very good flame-retardant properties, e.g. for shampooing treatments and carpet washing.
- the basic fabric of the tufted carpets can consist of cotton, jute, cellulose, wool, or synthetic fibers based on polyamide or polyester, polypropylene or in a mixture, or of glass fibers. Needled nonwovens made of polyester or polypropylene fiber are also suitable, excellent as a base fabric for the process according to the invention.
- fiber material made of wool, polyamide, polyester as well as polyacrylonitrile or their mixtures e.g. Polyacrylonitrile / polyester 80/20.
- Fiber material made of wool, polyamide or polyester threads with the usual cutting height of 4 to 12 mm is preferred.
- plastic dispersions polyvinyl acetate are suitable polyvinyl acetate, with plastic plasticizers such as dibutyl phthalate, copolymers of vinyl acetate with dibutyl maleate, copolymers of butyl acrylate with N-methylol acrylamide, copolymers of acrylic acid butyl ester, N-Methylolacylamid and acrylic acid, copolymers of butyl acrylate, N-methylolacrylamide and / or N- Methylol methacrylamide and acrylic acid, copolymers of butyl acrylate, methyl methacrylate and methylol methacrylamide, copolymers of butyl acrylate, acrylonitrile, N-methylol acrylamide and methacrylic acid, copolymers of butyl acrylate, ethyl acrylate.
- plastic plasticizers such as dibutyl phthalate, copolymers of vinyl acetate with dibutyl male
- Preferred polymer dispersions are polyvinyl acetate dispersions (50%), copolymers of vinyl acetate with maleic acid dibutyl ester, e.g. in the ratio 77/23 (approx. 50%), copolymers of styrene / butyl acrylate / acrylonitrile / methacrylic acid / acrylamide e.g.
- the impregnation liquors for both the primer and the back coating for woven carpets also contain thickeners, which are intended to prevent the finishing solution from penetrating into the pile and sticking together.
- thickeners are water-soluble hydroxyethyl celluloses, methyl celluloses, carboxymethyl celluloses, water-soluble starch products, partially etherified or etherified starch products, polyvinyl alcohols, the sodium or ammonium salts of alginic acid.
- the primer or the carpet backing for woven carpets can also be filled with chalk as usual.
- metal oxides can also be used as fillers, such as aluminum oxide, aluminum hydroxide, aluminum oxide hydrate.
- the method according to the invention for the flame-retardant finishing of pile carpets or woven carpets by means of a back coating is likewise carried out under application conditions as are customary in the textile industry.
- the primer for tufted carpets or the back finish for woven carpets which contains the flame-retardant compound, the crosslinker, the plastic dispersion and the catalyst, is applied with the help of an air knife, a rubber squeegee or cylinder squeegee. Then, on a tenter, dried or in gelling or 'dry channels or cylinder dryers at 125 ° to 150 ° C cured.
- the dwell time depends on the thickness of the carpets and is between 5 to 20 minutes, primarily 7 to 10 minutes.
- tufted carpets there is generally a back coating with natural latex, synthetic latex dispersion, e.g. based on butadiene styrene 40:60 or 60:40.
- the flame-retardant primer forms a barrier layer against the latex back so that it does not catch fire.
- the flame retardant process according to the invention is also distinguished by the fact that no aggressive vapors can form in the form of hydrogen halide when exposed to flame, as is the case to a great extent when flame retardant components based on chlorinated paraffin, PVC, inorganic or organic bromine compounds are used.
- the described flame-retardant systems on the various textile materials are characterized by very good durability.
- the flame-retardant equipment is easy to grasp when subjected to mechanical stress, such as rolling in the needle felt, the tufted carpets, the woven carpets or even sharp ones Kinks do not break or powder the finish.
- This elastic behavior of the equipment which also shows no or only very slight swelling in wet treatments, should be partly responsible for the very good wash resistance on the textile goods described and for the excellent integration of the pile threads in the tufting base fabric.
- the equipment generally also shows good antistatic behavior and in many cases makes it unnecessary to add antistatic agents or carbon black dispersions.
- the incorporation of antistatic products, textile softeners and oleophobicizing agents is generally not difficult.
- a coarse-thread needle felt fabric which consists of a polyester fiber core and a polyamide tread in a mixing ratio of 65:35 and has a weight per square meter of approx. 800 g / m 2 , is treated on a two-roll pad with an aqueous solution consisting of the following individual components:
- the needle felt shows a very good flame retardant effect that lasts several shampoos and washes at 40 - 50 ° C.
- the flame retardant test is carried out in accordance with DIN 54 333, determination of the flame propagation speed of textiles, or in accordance with motor vehicle safety standard No. 302 (U.S. MVSS 302).
- the needle felt material equipped according to the invention does not continue to burn after the test flame has been removed. Outside the test section, only an afterglow of 10-15 seconds could be determined. After three fine washes with 2 g / 1 of a commercially available mild detergent (the washing time is 15 minutes at 40 ° C), the needle felt also does not burn.
- the afterflame time had only increased to 40-60 seconds. After 5 shampoos, the needle felt also does not burn. The afterflame time is 50 seconds.
- the needle felted goods are equipped with 200 g / 1 of the plastic dispersion listed in the example, the needle felt burns in 3 minutes and 45 seconds after removal in a broad direction.
- the flame-retardant needle felt is elastic and dimensionally stable.
- the reaction product of propanephosphonic anhydride, pentaerythritol and ethylene oxide described in Example 1 is used as a flame-retardant component of a primer finish for a tufted article.
- the primer is applied using a rubber squeegee and dried at 145 ° C for 10 minutes.
- the order must be controlled so that the dry run is approximately 800 g / m 2 .
- the treated tufted carpet shows a flexible grip and excellent dimensional stability.
- the impregnation solution has not penetrated the pile threads.
- the polyamide pile shows its original mobility.
- the pile threads are excellently consolidated in the base fabric.
- a carpet back coating is then applied to a rubber squeegee using the foam process.
- a section of the tufted described above ware provided with a primer, which contains no flammhemmenden Kompo- n ducks.
- the pile threads are integrated with a 50% butadiene-styrene dispersion (60:40), chalk and methylol hydroxyethyl cellulose as a thickener. After drying, the smooth foam described above is applied.
- the flame retardant test according to the Nordtest method No. 7 gives the following finding: The section of carpet that does not contain a flame-retardant primer shows no. 7 no flame protection. After the pile of wood goes out, the section of carpet continues to burn across the dimensional mark of 60 cm. The flame-retardant section of the carpet goes out after the wood pile has burned off and shows a burn-in length of 30 cm, a burn-in width of 12 cm and an after-burn of 10 seconds.
- the flame-retardant smooth foam back is not affected by the action of the flame.
- the excellent flame retardant effect is retained even after 6 shampoos or after several wet treatments.
- the tufted carpet described in Example 2 is treated with a primer impregnation, which has the following composition:
- the primer is applied again using a rubber squeegee and dried for 12 minutes at 140 ° C.
- the dry edition is 780 g / m 2 .
- the tufted carpet equipped in this way has an elastic handle.
- the carpet pile is not glued because the primer has not penetrated the base fabric.
- the tufted carpet treated in this way burns after the flame protection test according to the Nordtest method No. 7 for floor coverings after burning the pile of wood no further.
- the burn-in length is 30 cm, the burn-in width 16 cm. After 3 minutes, afterburn is no longer observed.
- the flame retardant effect is excellent shampoo resistant and lasts for several wet treatments.
- a needle felted fabric (700 g / m 2 ), which consists of a fine-thread polypropylene core and a coarse thread tread made of polypropylene threads, is treated on a two-roll pad with an aqueous impregnation solution, which has the following composition:
- the flame-retardant effect of the very elastic and dimensionally stable needle felt is excellent and lasts for several shampooing treatments.
- the flame retardant effect is tested in accordance with DIN 54 333 "Determination of the Flame Spread Rate". After the test flame has been removed, the needle felt burns out for 30 seconds outside the test zone. After 3 shampoos the needle felt burns for 60 seconds. The flame does not reach the test zone.
- the needle felt is only equipped with 200 g / 1 of the plastic dispersion mentioned in the example, this needle felt continues to burn after the test flame has been removed. The flame traverses 10 cm of the test section in 2 minutes and 30 seconds.
- the squeezing effect is 95%. Drying takes place at 135 ° C for 25 minutes.
- Example 2 The tufted described in Example 2 is provided mit.einem V orstrich, which consists of the following components:
- the primer is applied using a rubber squeegee and dried or condensed at 140 ° C for 15 minutes.
- the dry edition is approx. 780 g / m 2 .
- the tufted carpet treated in this way shows a flexible grip.
- the integration of the individual threads in the basic fabric is sufficient draws.
- the applied finish does not break.
- the impregnation liquor has not penetrated the pile threads.
- the same tufting goods are only equipped with the butadiene-styrene dispersion and the 3.0% methylhydroxyethyl cellulose solution.
- test object of the flame-retardant tufted goods only continues to burn for 15 seconds after the test flame has been removed (the flame does not reach the test section), the test object continues to burn without flame-retardant equipment.
- the flame traverses a test section of 10 cm in 2 minutes and 50 seconds.
- the squeezing effect is 95%.
- the mixture is then dried at 135 ° C for 20 minutes.
- the needle felt is a very good flame retardant effect, several shampoos' and fine washes at 40 ° C survived.
- the flame retardant test is carried out in accordance with DIN 54 333.
- the needle felt test piece does not continue to burn after the test flame has been removed. Only an afterburn of 1.0 seconds outside the test zone could be determined.
- the needle felt which was washed three times with 2 g / 1 of a commercially available mild detergent, also did not burn after the test flame was removed.
- the afterburn time is 55 seconds outside the test zone.
- the flame-retardant needle felt is elastic, lightly filled and dimensionally stable.
- the needle felt is very well permanently flame retardant.
- the handle is elastic, slightly filled, but not hardened.
- a tufted carpet fabric with a square weight of 650 g / m 2 which consists of a 6 mm high polyester pile, tufted on a carrier material made of needled polypropylene nonwoven (100 g / m 2 ) is equipped with a primer of the following composition:
- the primer is applied using a hand knife and dried at 145 ° C for 10 minutes.
- the dry edition is approx. 750 g / m 2 .
- the tufted carpet treated in this way shows a flexible grip and very good dimensional stability.
- the pile threads are very well consolidated in the base fabric.
- the tufted carpet treated in this way meets the test standard DIN 54333. After the test flame has been removed, the carpet burns for only 20 seconds. The flame does not reach the test section.
- a needle felt made of polypropylene fibers, as described in Example 4, is treated with an impregnation solution of the following composition:
- the needle felt is treated on a 2-roll pad and squeezed off. 100% wet pad.
- the mixture is then dried at 135 ° C for 25 minutes.
- the needle felt shows an excellent flame retardant effect according to the US safety standard for motor vehicles No. 302. (U.S. MVSS 302). After the test flame was removed, the needle felt only burned for 5 seconds.
- the needle felt is elastic and dimensionally stable.
- Example 1 The needle felt described in Example 1, which consists of a polyester fiber core and a polyamide tread, is treated with an impregnation solution which has the following composition:
- the needle felt is squeezed off on a two-roll pad.
- the mixture is then dried or condensed at 140 ° C. for 25 minutes.
- the needle felt is lightly filled and elastic.
- the needle felt also shows a very good flame retardant effect that survives several shampooings.
- the flame retardancy test is carried out in accordance with D IN 54 333 "Determination of the flame propagation speed of textiles". After flame treatment, the needle felt burns for 45 seconds after / without reaching the test section. After 3 shampoos, the needle felt burns 60 seconds after the test flame is removed.
- Example 2 The tufting carpet described in Example 2 is treated with the following primer impregnation solution using a rubber squeegee:
- the knife application is controlled so that the dry coating is approximately 750 g / m 2 .
- the tufted carpet provided with the primer described above shows a flexible handle and very good shape stability after drying.
- the impregnation solution has not penetrated the pile threads.
- the pile threads have retained their full mobility and are not glued to the walk-in side.
- the tufted carpet thus equipped is very well permanently flame retardant.
- the flame retardant test is carried out in accordance with DIN 54 333, "Determination of the Flame Spread Rate". After the test flame has been removed, the tufting carpet burns for 50 seconds. After three wet treatments with 2 g / 1 of a commercially available mild detergent for 10 minutes at 40 ° C, the tufted carpet burns for 55 seconds after the test flame has been removed without reaching the test section.
- the tufting carpet described in Example 2 with a square meter weight of 650 g, consisting of a polyamide pile of 6 mm, tufted on polypropylene fleece (approx. 100 g / m 2 ) is provided with a primer with the aid of a laboratory rake.
- the application must be controlled so that the dry laydown is approx. 780 - 800 g / m 2 . After the doctor blade treatment, it is dried at 145 ° C. for 12-15 minutes.
- the primer impregnation solution is constructed similarly to that described in Example 2: "burns after" means that the flames of DIN 54 333 do not reach the 1st mark on the test track. (Very good values!
- test object burns e.g. 10 ", 1 'etc. and then goes out.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Fireproofing Substances (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyethers (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2726478 | 1977-06-11 | ||
DE19772726478 DE2726478A1 (de) | 1977-06-11 | 1977-06-11 | Phosphor enthaltende polyaddukte und verfahren zu deren herstellung |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000024A1 true EP0000024A1 (fr) | 1978-12-20 |
EP0000024B1 EP0000024B1 (en) | 1982-06-02 |
Family
ID=6011358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100036A Expired EP0000024B1 (en) | 1977-06-11 | 1978-06-01 | Polyadducts containing phosphorus and their application in the flameproofing of textile materials |
Country Status (6)
Country | Link |
---|---|
US (1) | US4244893A (fr) |
EP (1) | EP0000024B1 (fr) |
JP (1) | JPS545000A (fr) |
CA (1) | CA1113953A (fr) |
DE (2) | DE2726478A1 (fr) |
IT (1) | IT1096712B (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0002733A2 (fr) * | 1977-12-29 | 1979-07-11 | Hoechst Aktiengesellschaft | Procédé de préparation d'anhydrides d'acides phosphiniques et phosphoniques |
EP0004323A1 (fr) * | 1978-03-17 | 1979-10-03 | Hoechst Aktiengesellschaft | Procédé de préparation d'anhydrides d'acides alcanephosphoniques et alcane-bis-alcoylphosphiniques |
EP0005329A1 (fr) * | 1978-04-20 | 1979-11-14 | Stauffer Chemical Company | Procédé de préparation de produits du type poly(oxyorganophosphate/phosphonate), produits obtenus, utilisation de certains de ces produits comme retardateurs de combustion et matériaux traités avec ces produits |
EP0009706A1 (fr) * | 1978-09-27 | 1980-04-16 | Hoechst Aktiengesellschaft | Composés organiques du phosphore contenant des groupes ester d'acides hydroxy-3 alkylphosphiniques, leur préparation et utilisation |
WO2008129559A2 (fr) | 2007-04-23 | 2008-10-30 | Serum Institute Of India Ltd | Polysaccharides antigéniques et procédé pour leur préparation |
WO2011148382A1 (fr) | 2010-05-28 | 2011-12-01 | Biological E Limited | Procédé amélioré de purification de polysaccharides capsulaires de haemophilus influenza - b, neisseria meningitides tels que les sérotypes a, c, y et w-135, et d'autres polysaccharides capsulaires apparentés produits à partir de microorganismes à la fois à gram négatif et à gram positif en utilisant un phosphate d'aluminium avec un alcool. |
WO2013087178A1 (fr) * | 2011-12-16 | 2013-06-20 | Clariant International Ltd | Mélanges d'acides diphosphiniques et d'acides alkylphosphoniques, procédé pour leur préparation et leur utilisation |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4335178A (en) * | 1979-09-10 | 1982-06-15 | Stauffer Chemical Company | Textiles containing a poly(oxyorganophosphate/phosphonate) flame retardant |
DE3007714A1 (de) * | 1980-02-29 | 1981-10-08 | Hoechst Ag, 6000 Frankfurt | Oligomere phophonsaeureester und deren verwendung als flammhemmitelle |
US5756638A (en) * | 1993-03-15 | 1998-05-26 | Hoechst Ag | Phosphorus-modified epoxy resins, process for the preparation thereof and use thereof |
DE19635489C2 (de) * | 1996-09-02 | 1998-11-26 | Clariant Gmbh | Flammwidrige, ungesättigte Polyesterharze, Verfahren zu deren Herstellung und ihre Verwendung zur Herstellung von Formkörpern, Laminaten oder Beschichtungen |
JP4695279B2 (ja) * | 2001-03-21 | 2011-06-08 | 日華化学株式会社 | 難燃加工剤、難燃加工方法、及び難燃加工繊維 |
AU2003215331A1 (en) * | 2002-02-22 | 2003-09-09 | University Of Georgia Research Foundation | Catalyst system andmethod for preparing flame resistant materials |
DE10309570B3 (de) * | 2003-03-04 | 2004-09-02 | Clariant Gmbh | Modifizierte Polyethylenphosphinsäuren und deren Salze |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1156563B (de) * | 1959-02-24 | 1963-10-31 | Hoechst Ag | Verfahren zur Herstellung von Polykondensationsprodukten mit oberflaechenaktiven Eigenschaften auf der Basis von Alkylenglykolen |
GB1080938A (en) * | 1964-08-13 | 1967-08-31 | Kuhlmann Ets | Method of preparing phosphorylated polyols,and their application |
US3657145A (en) * | 1967-12-01 | 1972-04-18 | Petrolite Corp | Demulsification with linear polymeric phosphorus-containing esters |
US3764640A (en) * | 1970-07-23 | 1973-10-09 | Knapsack Ag | A process of making phosphorus and halogen containing polyols |
US4012463A (en) * | 1974-05-28 | 1977-03-15 | Stauffer Chemical Company | Method of preparing stable condensation products using a Lewis acid catalyst and products thereof |
FR2325658A1 (fr) * | 1975-12-16 | 1977-04-22 | Hoechst Ag | Procede de preparation de produits de polyaddition renfermant du phosphore |
-
1977
- 1977-06-11 DE DE19772726478 patent/DE2726478A1/de not_active Withdrawn
-
1978
- 1978-06-01 DE DE7878100036T patent/DE2861871D1/de not_active Expired
- 1978-06-01 EP EP78100036A patent/EP0000024B1/de not_active Expired
- 1978-06-06 US US05/913,083 patent/US4244893A/en not_active Expired - Lifetime
- 1978-06-09 IT IT24422/78A patent/IT1096712B/it active
- 1978-06-09 CA CA305,092A patent/CA1113953A/fr not_active Expired
- 1978-06-10 JP JP6940178A patent/JPS545000A/ja active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1156563B (de) * | 1959-02-24 | 1963-10-31 | Hoechst Ag | Verfahren zur Herstellung von Polykondensationsprodukten mit oberflaechenaktiven Eigenschaften auf der Basis von Alkylenglykolen |
GB1080938A (en) * | 1964-08-13 | 1967-08-31 | Kuhlmann Ets | Method of preparing phosphorylated polyols,and their application |
US3657145A (en) * | 1967-12-01 | 1972-04-18 | Petrolite Corp | Demulsification with linear polymeric phosphorus-containing esters |
US3764640A (en) * | 1970-07-23 | 1973-10-09 | Knapsack Ag | A process of making phosphorus and halogen containing polyols |
US4012463A (en) * | 1974-05-28 | 1977-03-15 | Stauffer Chemical Company | Method of preparing stable condensation products using a Lewis acid catalyst and products thereof |
FR2325658A1 (fr) * | 1975-12-16 | 1977-04-22 | Hoechst Ag | Procede de preparation de produits de polyaddition renfermant du phosphore |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0002733A2 (fr) * | 1977-12-29 | 1979-07-11 | Hoechst Aktiengesellschaft | Procédé de préparation d'anhydrides d'acides phosphiniques et phosphoniques |
EP0002733A3 (fr) * | 1977-12-29 | 1979-07-25 | Hoechst Aktiengesellschaft | Procédé de préparation d'anhydrides d'acides phosphiniques et phosphoniques |
EP0004323A1 (fr) * | 1978-03-17 | 1979-10-03 | Hoechst Aktiengesellschaft | Procédé de préparation d'anhydrides d'acides alcanephosphoniques et alcane-bis-alcoylphosphiniques |
EP0005329A1 (fr) * | 1978-04-20 | 1979-11-14 | Stauffer Chemical Company | Procédé de préparation de produits du type poly(oxyorganophosphate/phosphonate), produits obtenus, utilisation de certains de ces produits comme retardateurs de combustion et matériaux traités avec ces produits |
EP0009706A1 (fr) * | 1978-09-27 | 1980-04-16 | Hoechst Aktiengesellschaft | Composés organiques du phosphore contenant des groupes ester d'acides hydroxy-3 alkylphosphiniques, leur préparation et utilisation |
WO2008129559A2 (fr) | 2007-04-23 | 2008-10-30 | Serum Institute Of India Ltd | Polysaccharides antigéniques et procédé pour leur préparation |
WO2011148382A1 (fr) | 2010-05-28 | 2011-12-01 | Biological E Limited | Procédé amélioré de purification de polysaccharides capsulaires de haemophilus influenza - b, neisseria meningitides tels que les sérotypes a, c, y et w-135, et d'autres polysaccharides capsulaires apparentés produits à partir de microorganismes à la fois à gram négatif et à gram positif en utilisant un phosphate d'aluminium avec un alcool. |
WO2013087178A1 (fr) * | 2011-12-16 | 2013-06-20 | Clariant International Ltd | Mélanges d'acides diphosphiniques et d'acides alkylphosphoniques, procédé pour leur préparation et leur utilisation |
Also Published As
Publication number | Publication date |
---|---|
US4244893A (en) | 1981-01-13 |
DE2726478A1 (de) | 1978-12-14 |
JPS545000A (en) | 1979-01-16 |
DE2861871D1 (en) | 1982-07-22 |
EP0000024B1 (en) | 1982-06-02 |
IT7824422A0 (it) | 1978-06-09 |
IT1096712B (it) | 1985-08-26 |
CA1113953A (fr) | 1981-12-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0000024A1 (fr) | Produits oligomères phosphorés et leur utilisation comme apprêts textiles ignifugeants | |
DE2131040A1 (de) | Triazinylaminoalkyl-phosphonate und deren Verwendung zum Flammfestmachen | |
DE2146988C3 (de) | Verfahren zur Herstellung von organischen Phosphorverbindungen | |
DE2401221A1 (de) | Antistatisches textil- und bodenbelagsprodukt | |
EP0057668A2 (fr) | Sels d'acides phosphoniques, leur obtention et leur utilisation pour ignifuger des fibres organiques | |
DE2225934A1 (de) | Mittel zum flammfestmachen von textilien und deren verwendung | |
US4096208A (en) | Polyphosphinites and a process for their preparation | |
EP0003599A1 (fr) | Composés de phosphore organique avec des groupes d'acide 2-hydroxyalkyl phosphoriques, procédé pour leur préparation et leur application comme adjuvant retardant l'inflammation | |
DE2556482A1 (de) | Verfahren zur herstellung von phosphor enthaltenden polyaddukten | |
WO2021204571A1 (fr) | Surfaces textiles dotées d'un apprêt ignifuge à l'aide de produits de polycondensation | |
DE1594947C3 (de) | Phosphorhaltige, härtbare und wasserlösliche Aminoplaste, sowie deren Verwendung zum Flammfestmachen von Textilmaterial | |
EP0009706A1 (fr) | Composés organiques du phosphore contenant des groupes ester d'acides hydroxy-3 alkylphosphiniques, leur préparation et utilisation | |
DE2707560C3 (de) | Mittel zum Flammfestmachen von Polyester/Baumwolle-Mischgeweben | |
EP0035162A2 (fr) | Esters d'acides phosphoniques oligomères et leur utilisation comme retardateurs de combustion | |
DE2825818A1 (de) | Verfahren zur flammhemmausruestung von florteppichen | |
DE4101539A1 (de) | Zusammensetzung zur flammfestausruestung von fasermaterialien | |
DE2918568A1 (de) | Organische phosphor-verbindungen mit 3-hydroxyalkylphosphonsaeureestergruppen | |
DE2449465A1 (de) | Flammschutzausruestung von textilien | |
JP3040842B2 (ja) | ポリエステル系難燃性スパンボンド不織布 | |
DE2837314A1 (de) | Koagulierungsmittel fuer binderdispersionen zum verkleben von fasern in vliesstoffen | |
DE2610180C3 (de) | Verfahren zur flammfesten Ausrüstung von Textilien | |
DE1768630A1 (de) | alpha-,ss-,oder gamma-funktionelle Fluoralkylsiliziumverbindungen,ihre Herstellung und Verwendung als Tenside mit oleophober Impraegnierwirkung | |
EP0561223A2 (fr) | Composition contenant des produits de réaction de phosphites, quinones et isocyanates | |
EP1674471A1 (fr) | Composés organosiliques contenant des fractions de l'azote | |
DE2118953B2 (de) | Verfahren zum Flammfestmachen von Fasermischungen aus Polyester und Cellulose |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): BE CH DE FR GB NL Kind code of ref document: A1 Designated state(s): BE CH DE FR GB NL |
|
17P | Request for examination filed | ||
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): BE CH DE FR GB NL Designated state(s): BE CH DE FR GB NL |
|
18W | Application withdrawn |
Withdrawal date: 19820407 |
|
PUAC | Information related to the publication of a b1 document modified or deleted |
Free format text: ORIGINAL CODE: 0009299EPPU |
|
REF | Corresponds to: |
Ref document number: 2861871 Country of ref document: DE Date of ref document: 19820722 |
|
DB1 | Publication of patent cancelled | ||
GBPC | Gb: european patent ceased through non-payment of renewal fee | ||
BERE | Be: lapsed |
Owner name: DEMANDE RETIREE Effective date: 19860630 |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: LINKE, FRITZ, DR. Inventor name: KLEINER, HANS-JERG, DR. Inventor name: DUERSCH, WALTER, DR. |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R137 Ref document number: 2861871 Country of ref document: DE |