US3877974A - Flame retardants for blends of natural and synthetic fibers - Google Patents
Flame retardants for blends of natural and synthetic fibers Download PDFInfo
- Publication number
- US3877974A US3877974A US33073172A US3877974A US 3877974 A US3877974 A US 3877974A US 33073172 A US33073172 A US 33073172A US 3877974 A US3877974 A US 3877974A
- Authority
- US
- United States
- Prior art keywords
- polybrominated
- flame retardant
- fabric
- acrylonitrile
- flame
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- 239000003063 flame retardant Substances 0.000 title claims description 36
- 229920002994 synthetic fiber Polymers 0.000 title abstract description 7
- 239000012209 synthetic fiber Substances 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 39
- 229920000126 latex Polymers 0.000 claims abstract description 29
- 239000004816 latex Substances 0.000 claims abstract description 19
- 239000002245 particle Substances 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 238000004900 laundering Methods 0.000 claims abstract description 10
- 238000005108 dry cleaning Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 8
- 239000011230 binding agent Substances 0.000 claims abstract description 5
- 238000009877 rendering Methods 0.000 claims abstract description 3
- 239000006185 dispersion Substances 0.000 claims description 43
- 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 33
- 239000000463 material Substances 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 19
- -1 Polybrominated biphenyl Polybrominated biphenyl oxide Polybrominated benzene Polybrominated toluene Polybrominated chlorotoluene Polybrominated phenol Polybrominated aniline Polybrominated benzoic acid Tris phosphates Chemical class 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 14
- 229910044991 metal oxide Inorganic materials 0.000 claims description 14
- 239000000839 emulsion Substances 0.000 claims description 12
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- 239000004753 textile Substances 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 229910052797 bismuth Inorganic materials 0.000 claims description 5
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 4
- PLOYJEGLPVCRAJ-UHFFFAOYSA-N buta-1,3-diene;prop-2-enoic acid;styrene Chemical compound C=CC=C.OC(=O)C=C.C=CC1=CC=CC=C1 PLOYJEGLPVCRAJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- GDPZFIFONYKTID-UHFFFAOYSA-N butyl prop-2-enoate;n-(hydroxymethyl)prop-2-enamide;prop-2-enenitrile Chemical compound C=CC#N.OCNC(=O)C=C.CCCCOC(=O)C=C GDPZFIFONYKTID-UHFFFAOYSA-N 0.000 claims description 3
- 238000010345 tape casting Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 238000005470 impregnation Methods 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 25
- 239000000049 pigment Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 239000012757 flame retardant agent Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- 239000000088 plastic resin Substances 0.000 abstract 1
- 239000003223 protective agent Substances 0.000 abstract 1
- 239000000758 substrate Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- 239000000835 fiber Substances 0.000 description 9
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000005395 methacrylic acid group Chemical class 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- 239000011120 plywood Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 206010013786 Dry skin Diseases 0.000 description 3
- 239000004908 Emulsion polymer Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 230000000979 retarding effect Effects 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical class ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 2
- 229920001747 Cellulose diacetate Polymers 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000011152 fibreglass Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 235000011087 fumaric acid Nutrition 0.000 description 2
- 150000002238 fumaric acids Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002689 maleic acids Chemical class 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical group C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- AQPHBYQUCKHJLT-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4,5,6-pentabromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=C(Br)C(Br)=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br AQPHBYQUCKHJLT-UHFFFAOYSA-N 0.000 description 1
- OZHJEQVYCBTHJT-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-methylbenzene Chemical compound CC1=C(Br)C(Br)=C(Br)C(Br)=C1Br OZHJEQVYCBTHJT-UHFFFAOYSA-N 0.000 description 1
- MICWFONKQCWHSD-UHFFFAOYSA-N 2,3-dibromobicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C(Br)=C(Br)C1C2 MICWFONKQCWHSD-UHFFFAOYSA-N 0.000 description 1
- GVPODVKBTHCGFU-UHFFFAOYSA-N 2,4,6-tribromoaniline Chemical compound NC1=C(Br)C=C(Br)C=C1Br GVPODVKBTHCGFU-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GJIBIERRUICXNV-UHFFFAOYSA-N 6-phenyl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical class O1C2C=CC=CC12C1=CC=CC=C1 GJIBIERRUICXNV-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 241000870659 Crassula perfoliata var. minor Species 0.000 description 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- YHFQWCGSZDZXSX-UHFFFAOYSA-N dibromo phenyl phosphate Chemical compound BrOP(=O)(OBr)OC1=CC=CC=C1 YHFQWCGSZDZXSX-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- CAYGQBVSOZLICD-UHFFFAOYSA-N hexabromobenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1Br CAYGQBVSOZLICD-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
- D06M13/338—Organic hydrazines; Hydrazinium compounds
-
- 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
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
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- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
- D06M11/20—Halides of elements of Groups 4 or 14 of the Periodic Table, e.g. zirconyl chloride
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- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/45—Oxides or hydroxides of elements of Groups 3 or 13 of the Periodic Table; Aluminates
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- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/46—Oxides or hydroxides of elements of Groups 4 or 14 of the Periodic Table; Titanates; Zirconates; Stannates; Plumbates
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- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/47—Oxides or hydroxides of elements of Groups 5 or 15 of the Periodic Table; Vanadates; Niobates; Tantalates; Arsenates; Antimonates; Bismuthates
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- D06M11/77—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with silicon or compounds thereof
- D06M11/79—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with silicon or compounds thereof with silicon dioxide, silicic acids or their salts
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- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/152—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
- D06M13/21—Halogenated carboxylic acids; Anhydrides, halides or salts thereof
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- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
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- 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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
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- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/693—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural or synthetic rubber, or derivatives thereof
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- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
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- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/32—Polyesters
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- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/30—Flame or heat resistance, fire retardancy properties
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/92—Fire or heat protection feature
- Y10S428/921—Fire or flameproofing
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2631—Coating or impregnation provides heat or fire protection
- Y10T442/2713—Halogen containing
Definitions
- ABSTRACT A process for rendering synthetic materials, of synthetic fibers or mixtures of the same flame resistant which entails employing water insoluble flame retardant agents which are treated as colorless pigments, reduced to extremely finely divided condition, suspended in latex medium and applied as such or as part of a dispersed dye paste to the fabric, dried and set in place.
- flame retardance or flame resistance of a fabric is a highly desirable characteristic.
- the principal ones being the inability of the flame retardant material, or treatment, to last through laundering or dry cleaning operations.
- Another principal disadvantage of treatments of fabrics to develop this characteristic of flame retardance is the loss of hand in the substrate. The problem is greatly aggravated in some areas of handling, particularly where it is necessary to meet statutory requirements for flame retardance in garments.
- Their physical condition being in the form of a bundle of fine fibers invites and encourages the sustenance of a flame if one gets started in the fabric. That is, a large area of oxidation is presented to any flame which gets started.
- the present invention relates to a new method of flame retarding textile and related materials using a commonly employed method in pigment printing and dyeng, that is, through the use of a primary binder which serves as an adhesive to fasten the flame retardant to a given substrate.
- this technique can also be employed to flame retard the said binders, which normally are emulsions of synthetic polymeric materials which are highly flammable and contribute to the flammability of flame retarded substrates.
- the subject of the present invention consists of two basic elements, the flame retardant element and a binding element.
- the flame retarding element is a colorless highly halobrominated, organic compound, solid at room temperature, possessing high melting and decomposition points, which is easily reduced to an extremely small particle size by conventional means of grinding.
- the solid flame retardant material is reduced to a submicron or micron particle size and suspended in water in a fashion similar to the preparation of pigment disper sions.
- a synergist which will contribute to render the halobrominated solids more heat unstable must be-employed.
- This synergist must possess similar characteristics to the halobrominated flame retardant, that is, it is a micropulverized solid possessing good heat stability, finely dispersed in water.
- it must react with the halobrominated flame retarder at combustion temperatures to form a gaseous non-flammable gas which will prevent oxygen from reaching the flaming substrate, thus impeding the oxidation process.
- the second element used in this invention is an emulsion of a high molecular weight polymer, commonly referred to as latex.
- the polymer employed can be the result of polymerizing acrylic acid, methacrylic acid, acrylamide, methacrylamide, acrylonitrile, esters of acrylic and methacrylicacids, vinyl chloride, vinylidene chloride, styrene, butadiene, maleic or fumaric acids and esters of same and the like.
- the polymer can be homopolymers or copolymers of the above described monomers.
- These emulsion polymers are commercially available in differing grades depending on the ultimate properties desired. They have in common the fact that they form films at room or elevated temperatures, alone or in the presence of plasticizers. The properties of the film depend on the chemical composition of the same.
- the latexes possess extremely good adhesive properties, they are normally used for bonding purposes. They are used for bonding of pigments to hard to dye substrates, to bond fibers with fibers to obtain non woven fabrics, to bond fibers to fabrics to produce flocked fabrics and to bond fabrics to fabrics, fabrics to foams, fabrics to films, to non wovens, etc., to obtain laminated fabrics. They are also used for fabric backcoating to achieve various effects such as dimensional stability, to prevent ravelling, to give fabrics non-slipping characteristics, with a filler, to impart opacity to the same, etc., and for finishing to achieve dimensional stability, to increase strength, decreasae air permeability, impart waste repellency, etc.
- This invention relates to two uses of these materials:
- the solid flame retardant is the predominant ingredient and the latex is the minor ingredient.
- micropulverized solid flame retardant is first dispersed in water containing a wetting agent by adding it slowly to the aqueous phase under strong agitation, with a high speed, high shear mixer. After addition of the solid has been completed, the resulting dispersion is stabilized by adding small quantities of a protective colloid (commonly called thickener) such as carboxy methyl cellulose, methoxy or ethoxycellulose of selected molecular weight to achieve an optimum viscosity and prevent the particles from settling.
- a protective colloid commonly called thickener
- the FR flame retardant
- the FR flame retardant
- This solution is now applied to the substrate by dipping it into this solution and removing the excess by squeezing between two rollers.
- the w'et substrate is now air dried at any convenient temperature and baked at C. to C. for to 90 seconds.
- the resulting material is flame retardant when tested by commonly used flammabililty tests and the flame retardant is not lost after multiple launderings and/or dry cleanings.
- the feel or hand of the flame retarded material is unchanged, but can be made stiff, if desirable, by selecting a harder latex.
- the FR dispersion prepared as described above, is diluted in water, the latex is added and the viscosity adjusted by the use of a thickener.
- This treating batch is now applied by different techniques depending on the final effect desired. It can be padded, knife coated, roller coated, sprayed, roller printed, screen printed, applied by saturation and the like.
- the substrates are now air dried at any convenient temperature, and baked as above.
- This technique is usually employed when the substrate to which the latex is applied is either intrinsically flame retardant or has been flame proofed in a separate operation. It can be used to flame retard latices, which will be employed as flocking adhesives, for fabric backcoating, pigment dyeing or printing, bonding or non woven fabric lamination and the like.
- the process of this invention is applicable to textile materials, in staple, tow, yarn, fiber, woven fabrics, non-woven fabrics, circular and flat knits, carpets and the like, to paper, to films, to foams, etc.
- the substrate can be of natural origin such as cotton, linen, jute, coco fiber, wool, silk and the like, man made such as regenerated cellulose, cellulose diand triacetates, fiberglass and the like or synthetic polymeric materials such as nylon, polyester, acrylics, polypropylene and the like.
- the present invention utilizes brominated aromatic compounds, preferably brominated as flame retarding materials.
- the preferred aromatic compounds employed are derivatives of Benzene Where A through N are the same can be H, Br, CH C I'I Ca 7,
- X, Y, Z can be the same or different and can be H, CH C H C 1, s s
- a to F are the same or different and may be H, Br, with at least one Br present on the benzene ring.
- R may be alkyl, preferably of 1-5 carbons such as methyl, ethyl, propyl, butyl, pentyl, isopropyl, tertbutyl; unsaturated alkyls, haloalkyl or polyhaloalkyl wherein the moiety may include up to four bromine atoms where the halogens are chlorine and/or bromine and A, B, C, D, E, are as above.
- R, and R are the same or different and are similar to R in (2).
- R and R are the same or different and can be H, alkyl preferably of 1-5 carbon atoms, bromoalkyl, polybromoalkyl and the like; aryl, phenyl, bromoaryl, bromophenyl, polybromoaryl, polybromopenyl, NH NH Na, K, Li, Ca, Ba, Sb, Ti and the like;
- a to J are the same or different and can be H, Br, lower alkyl C to C aryl,
- X being OH, NH,, ONH Na, K and the like.
- a to E are the same as in 5, and X and Y are H, lower alkyl C to C aryl, bromoalkyl, polybromoalkyl, bromoaryl, polybromoaryl, phenyl bromophenyl, polybromophenyl and the like.
- the synergists are normally metallic oxides of the general formula:
- Me can be Al, Ga, Si, Ge, As, Sb, Bi, Ti, Zr, and the like and n is the valence of the metal in its oxidized state. Especially are the oxides of aluminum, germanium, antimony and titanium useful.
- These oxides must also be present in a fine particle state of the same size as the halobrominated compound or smaller.
- the synergist is blended with the halobrominated compound during the preparation of the FR dispersion, the ratio of halobrominated compound to synergist depending on the stability of the halobrominated material and the reactivity of the particular metallic oxide employed. It was found that normally 3 to 7 parts halobrominated flame retarder for each part of metallic oxide, preferably 4-6 parts to 1 part, give the best results.
- the emulsion polymers commonly referred to as synthetic latices, are commercially available materials, obtained by emulsion homoor co-polymerization of monomers of the general class:
- the preferred monomers are alkyl esters of acrylic and methacrylic acids, acryland methacryl amides, acrylonitrile, acrylic and methacrylic acids, maleic or fumaric acids and alkyl esters of the same vinyl and vinylidene chlorides, styrene and butadiene.
- Acrylic latices mainly homoor co-polymers of alkyl esters of acrylic or methacrylic acids which can also contain acrylic or methacrylic acid, acrylonitrile, acrylamide, n-methylol acrylamide, vinyl and vinylidiene chlorides and the like.
- the alkyl group of the esters can also contain hydroxyl groups.
- reactive groups such as HO, CONH COOH,
- cross-linking self-cross linking 0r thermosetting latices.
- ABS acrylonitrile butadiene styrene
- SBR styrene butadiene rubber
- emulsion polymers obtained by the reaction of a polyisocyanate and an aliphatic polyol which can be a polyether, a polyester, or a polycaprolactone, the preferred polyisocyanate being a mixture of isomers of toluene diisocyanate and the preferred polyol being a polyethylene glycol condensate having a molecular weight in excess of 3,000, commonly referred to as a polyurethane latex.
- T.G. glass transition temperature
- T temperature at which the torsional modulus of an air dried film is 300 Kg/CM Both are measured in C and can range from l00C to +100C. As a general rule, the lower the T6 or T the softer the film, the film becoming harder with increasing temperatures.
- the strength of the film is also improved by increasaing the molecular weight of the polymer through the introduction of crosslinkable sites which are made to react by heat and/or catalysts.
- organic compound of a metallic oxide is slowly added. After addition is complete the dispersion is stabilized by adding 0.1 to 0.5%, preferably 0.2 to 0.3%, on the weight of the dispersion of a protective colloid such as ethoxy cellulose.
- FR dispersion 0.5 to 1.5 parts, preferably 0.8 to 1.2 parts, of FR dispersion are dissolved in 1 part of water with mild agitation.
- 0.05 to 0.4 preferably 0.1 to 0.3 part of a latex containing 35 to preferably 45 to 55%, of a polymer is added.
- 0.5.to 1.5%, preferably 0.8 to 1.2% of a wetting agent is added.
- The'substrate to be treated is dipped in this solution and the excess removed by squeezing between two rollers.
- the wet material is air dried in an oven at C to C, preferably 100C to 1 10C, and baked at C 9 to 18C, preferably 150C to 170C for /2 to minutes,
- the treating solution is prepared as follows: To 1 part of water 0.5 to 1.5 parts, preferably 0.8 to 1.2 parts, of latex is added, and the solution is mixed until uniform. 0.05 to 0.2 part, preferably 0.1 to 0.15 part, based on the weight of the latex of FR dispersion is added and mixed to uniformity. At this point any other needed auxiliaries, such as pigments, thickeners, fillers, plasticizers, wetting agents, catalysts, and the like, are incorporated in any required proportion and the solution mixed.
- the treating solution is now applied to the flame resistant substrate by any convenient way, such as padding, coating, printing, saturation and the like and the wet goods are dried and baked as above.
- EXAMPLE I 70 parts of finely divided decabromo biphenyl possessing an average particle size between 1 and 2 microns was slowly added to 50 parts water containing 0.2% anionic wetting agent of the alkyl-aryl sulfonate type, under strong agitation with a high speed, high shear mixer. After completing the addition of the brominated compound 12 parts of finely divided antimony-trioxide possessing an average particle size between 1 and 2 microns were slowly added while agitation was continued. After all the antimony trioxide was added the resulting milky white dispersion was stabilized by addition of 5 parts of a 4% aqueous solution, having a viscosity of 300,000 centipoise, of ethoxycellulose. This dispersion, thus obtained, remained uniform after prolonged storage at room temperature and was designated dispersion I.
- dispersion I 50 parts were now dissolved in 40 parts of water and parts of a 50% aqueous emulsion of a copolymer of ethyl acrylate and acrylamide having a T of -47C were added.
- a woven fabric weighing 4 ozs. per square yard composed of 50% cotton 50% polyester was now treated with this solution by immersing it in the same and removing the excess by squeezing between two rollers. The wet pick-up was 90%.
- the fabric was now dried at 1 10C and baked at 150C for 3 minutes.
- the fabric thus obtained was quite soft to the feel was further softened by padding it through a 10% emulsion of polyethylene softener in water.
- the flame resistance of the fabric thus treated was evaluated by testing according to test method given in Standard for the Flammability of Childrens Sleepwear" DOC FF3-71 giving an initial average char length of 1 V2 inches and 2 inches after 50 launderings and tumble dryings.
- EXAMPLE [1 70 parts of finely divided hexabromo benzene having an average particle size between 1 and 2 microns were dispersed in 50 parts of water in a similar fashion to dispersion l. parts of aluminum oxide were added to the dispersed brominated compound and this dispersion was stabilized as dispersion I. This material was designated dispersion ll.
- a piece of cotton circular knit weighing 8 02s- /yd was immersed in this solution and the excess removed by squeezing between two rollers. The wet pickup was and the fabric was dried at 110C and baked at C for 3 minutes. The fabric was softened by padding through a 10% emulsion of a polyethylene softener and dried.
- the fabric was judged flame retardant by using method outlined in DDC FF3-7 l giving an initial average char length of 1 inch and 2 /2 inches after 50 launderings and tumble dryings.
- EXAMPLE III 70 parts of finely divided pentabromo toluene and 20 parts of titanium dioxide having an average particle size of between 1 and 2 microns were dispersed in 50 parts of water as in Example I. This dispersion was designated dispersion Ill.
- dispersion III 50 parts of dispersion III were dissolved in 40 parts of water and 10 parts of a 50% acrylonitrile-styrenebutadiene latex having a glass transition temperature of 60C were added to this solution.
- the resulting mixture was padded onto a woven fabric composed of 80% rayon and 20% cellulose diacetate in a similar fashion as in Examples I and II.
- the fabric was dried at 1 10C, baked at 150C, top softened with a 10% emulsion of a polyethylene softener and redried.
- the treated fabric gave an average char length of 3 inches initially, when treated according to AATCC Flammability Test 34-1967, an average char length of 4 inches after 5 launderings and tumble dryings and an average char length of 5 inches after 5 commercial dry cleanings.
- EXAMPLE IV 70 parts of Tris dibromophenyl phosphate and 10 parts of antimony trioxide having an average particle size between 1 and 2 microns were dispersed in 40 parts of water as in Example 1. This dispersion was designated dispersion IV.
- a 100% woven fiberglass drapery fabric was immersed in this solution, the excess removed by squeezing between two rollers to obtain a wet pick-up of 50%, dried at 1 10C and baked at 150C for 3 minutes.
- This fabric gave an average char length of 3 inches when tested using AATCC flammability test 34-1967 initially, after 5 launderings and tumble drying and 5 commercial dry cleanings.
- EXAMPLE V 70 parts of finely divided tribromoaniline and 15 parts of micropulverized aluminum trioxide having a particle size of between 1 and 2 microns were dispersed in 50 parts of water following procedure given in Example I. This dispersion was designated as dispersion V.
- a piece of the 80% rayon 20% cellulose diacetate fabric treated in Example III was coated on one side with dispersion V-A using a doctor blade to a loading of 70% on the weight of the fiber.
- the fabric was dried at 125C and cured at 160C for 2 minutes.
- the fabric thus treated gave a char length of 3 inches when tested according to AATCC method 34-1967, initially after 5 launderings and 5 dry cleanings.
- the same fabric coated with the same composition, but without dispersion V was consumed entirely when tested by this flammability method.
- EXAMPLE VI Parts By Weight Vl-A Vl-B Water 300 300 Anionic Dispersing Agent l l Hydroxyethyl Cellulose Thickener 5 5 Talc I25 125 Rutile Titanium Dioxide 225 225 50% Solids Vinylacetateethylacrylute copolymer 400 400 Dispersion VI 45 The dispersion were prepared by predissolving the ingredients in the given order in a tank equipped with a high-speed high-shear mixer and then transferring the resulting dispersion into the pebble mill and milling for 5 hours.
- EXAMPLE VII 70 parts of finely divided hexachlorocyclopentadienodibromocyclooctane and 10 parts of micropulverized antimony trioxide having a particle size between 1 and 2 microns were dispersed in 40 parts of water following procedure given in Example I. This dispersion was designated dispersion Ill.
- dispersion Vll were dispersed in 40 parts of water and 40 parts of a 50% aqueous emulsion of a 5 polymer obtained by reaction of a mixture of isomers of toluene diisocyanate and a condensation product of ethylene glycol having a molecular weight of approximately 4,000.
- a piece of 100% nylon upholstery fabric was immersed in this solution and excess removed by squeezing between two rollers to achieve a 70% wet pickup and then dried at 125C.
- the fabric thus treated was judged flame retardant when it gave a 3 inches char length when listed according to AATCC method 34-1969, whereas the untreated fabric burned the entire length when tested according to the same method.
- said high molecular weight polymeric binder being present in amount sufficient to secure said brominated organic compound and metallic oxide flame retardant composition to said material, and drying and curing said treated material, wherein the total amount of flame retardant deposited on said material is effective to reduce the flammability of the textile and is durable to laundering and dry clean- 2.
- brominated solid organic material is selected from the group consisting of:
- a textile material inherently flammable, rendered and, N,N -ethyl-bis (dibromo-norbornenedicarboximide the metallic oxide is selected from the group consisting of:
- the latex is selected from the group consisting of:
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fireproofing Substances (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33073172 US3877974A (en) | 1972-10-25 | 1972-10-25 | Flame retardants for blends of natural and synthetic fibers |
CH1480573A CH614337GA3 (sv) | 1972-10-25 | 1973-10-19 | |
LU68656A LU68656A1 (sv) | 1972-10-25 | 1973-10-22 | |
BE136927A BE806353A (fr) | 1972-10-25 | 1973-10-22 | Methode d'ignifugation de materiaux synthetiques |
DE2352923A DE2352923C2 (de) | 1972-10-25 | 1973-10-22 | Verfahren und Mittel zur flammhemmenden Ausrüstung von brennbaren Materialien |
NL7314508A NL172169C (nl) | 1972-10-25 | 1973-10-23 | Werkwijze voor het brandwerend maken van een materiaal. |
SE7314388A SE405742B (sv) | 1972-10-25 | 1973-10-23 | Forfarande och medel att gora brennbara textilmaterial eldbestendiga |
AU61707/73A AU465965B2 (en) | 1972-10-25 | 1973-10-23 | Flame retardants for blends of natural and synthetic fibres |
GB4953073A GB1451335A (en) | 1972-10-25 | 1973-10-24 | Flame retardants |
CA184,142A CA987855A (en) | 1972-10-25 | 1973-10-24 | Flame retardants for synthetic materials (ii) |
FR7338995A FR2204675B1 (sv) | 1972-10-25 | 1973-10-24 | |
JP11977473A JPS49134772A (sv) | 1972-10-25 | 1973-10-24 | |
US05/415,667 US3955032A (en) | 1972-10-25 | 1973-11-14 | Flame retardants for natural and synthetic materials |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US30073172A | 1972-10-25 | 1972-10-25 | |
US33073172 US3877974A (en) | 1972-10-25 | 1972-10-25 | Flame retardants for blends of natural and synthetic fibers |
Publications (1)
Publication Number | Publication Date |
---|---|
US3877974A true US3877974A (en) | 1975-04-15 |
Family
ID=26971946
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US33073172 Expired - Lifetime US3877974A (en) | 1972-10-25 | 1972-10-25 | Flame retardants for blends of natural and synthetic fibers |
Country Status (11)
Country | Link |
---|---|
US (1) | US3877974A (sv) |
JP (1) | JPS49134772A (sv) |
AU (1) | AU465965B2 (sv) |
BE (1) | BE806353A (sv) |
CA (1) | CA987855A (sv) |
CH (1) | CH614337GA3 (sv) |
DE (1) | DE2352923C2 (sv) |
FR (1) | FR2204675B1 (sv) |
LU (1) | LU68656A1 (sv) |
NL (1) | NL172169C (sv) |
SE (1) | SE405742B (sv) |
Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3955032A (en) * | 1972-10-25 | 1976-05-04 | White Chemical Corporation | Flame retardants for natural and synthetic materials |
US3974310A (en) * | 1972-10-25 | 1976-08-10 | White Chemical Corporation | Flame retardants for synthetic materials (I) |
US4046701A (en) * | 1976-02-23 | 1977-09-06 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
US4054715A (en) * | 1975-09-11 | 1977-10-18 | Dixie Yarns, Inc. | Sewing thread containing a flame retardant lubricant |
US4087364A (en) * | 1973-01-26 | 1978-05-02 | American Cyanamid Company | Liquid slurry of submicron particles of hexabromobenzene, and process of manufacture |
US4113902A (en) * | 1975-05-22 | 1978-09-12 | White Chemical Corporation | Flame retardants for natural and synthetic materials |
US4116702A (en) * | 1974-12-13 | 1978-09-26 | Ciba-Geigy Corporation | Agent for flame proofing synthetic fibrous material |
US4151316A (en) * | 1977-11-09 | 1979-04-24 | Chas. S. Tanner Co. | Flameproofing of polyester fabrics using brominated cycloalkanes |
US4154692A (en) * | 1976-04-15 | 1979-05-15 | Mcelveen John B | Flame retardant process, solution and structures |
US4167603A (en) * | 1976-12-13 | 1979-09-11 | Ethyl Corporation | Flame resistant cotton/polyester blend substrates |
US4178399A (en) * | 1978-02-14 | 1979-12-11 | Chemonic Industries, Inc. | Flame retardant and process |
US4219605A (en) * | 1976-09-29 | 1980-08-26 | Ciba-Geigy Corporation | Process for flameproofing synthetic fibre material and product |
US4237157A (en) * | 1978-05-05 | 1980-12-02 | Henry Hancock | Process for making fire retardant polypropylene |
US4279652A (en) * | 1976-09-15 | 1981-07-21 | Sniaviscosa Societa Nazionale Industria Applicazioni Viscosa, S.P.A. | Self-extinguishing polymers |
US4298509A (en) * | 1977-10-05 | 1981-11-03 | Antonio Fochesato | Noninflammable olefin fibers and method of producing same |
EP0038899A1 (en) * | 1980-04-30 | 1981-11-04 | National Aeronautics And Space Administration | Flame retardant elastomeric compositions, heat sealable, flame and abrasion resistant fabrics coated therewith, and process for making same |
US4343854A (en) * | 1981-03-12 | 1982-08-10 | Witco Chemical Corporation | Flame retardant composition |
US4394413A (en) * | 1981-02-09 | 1983-07-19 | Scapa Dryers, Inc. | Flame retardant dryer fabrics |
US4522872A (en) * | 1982-04-12 | 1985-06-11 | Milliken Research Corporation | Industrial fabrics |
US4524170A (en) * | 1983-04-25 | 1985-06-18 | Milliken Research Corporation | Flame retardant finishing composition for synthetic textiles |
US4695507A (en) * | 1985-05-06 | 1987-09-22 | Burlington Industries, Inc. | Low toxic ceiling board facing |
US4719256A (en) * | 1984-07-23 | 1988-01-12 | Occidental Chemical Corporation | Fire retardant thermoplastic polyester and polyesterether compositions |
US4732789A (en) * | 1986-10-28 | 1988-03-22 | Burlington Industries, Inc. | Flame-resistant cotton blend fabrics |
US4750911A (en) * | 1986-09-26 | 1988-06-14 | Burlington Industries, Inc. | Flame-resistant nylon/cotton fabrics |
US4842609A (en) * | 1986-06-05 | 1989-06-27 | Burlington Industries, Inc. | Flame retardant treatments for polyester/cotton fabrics |
US4892769A (en) * | 1988-04-29 | 1990-01-09 | Weyerhaeuser Company | Fire resistant thermoplastic material containing absorbent article |
US4900377A (en) * | 1988-04-29 | 1990-02-13 | Weyerhaeuser Company | Method of making a limited life pad |
US4961930A (en) * | 1988-04-29 | 1990-10-09 | Weyerhaeuser Company | Pet pad of thermoplastic containing materials with insecticide |
US5290636A (en) * | 1990-09-06 | 1994-03-01 | Great Lakes Chemical Corp. | Flame retardant brominated styrene-based coatings |
US5296306A (en) * | 1992-11-18 | 1994-03-22 | Great Lakes Chemical Corp. | Flame retardant brominated styrene graft latex coatings |
USRE34951E (en) * | 1986-08-29 | 1995-05-23 | Interface, Inc. | Flame retardant tufted carpet tile and method of preparing same |
US5438096A (en) * | 1990-09-06 | 1995-08-01 | Great Lakes Chemical Corporation | Flame retardant brominated styrene-based latices |
US5484839A (en) * | 1992-11-18 | 1996-01-16 | Great Lakes Chemical Corp. | Flame retardant brominated styrene graft latex compositions |
US5858159A (en) * | 1995-04-25 | 1999-01-12 | Hoover Universal, Inc. | Method for manufacturing automotive seat assemblies using pre-bonded adhesives |
US8209785B2 (en) | 2010-02-09 | 2012-07-03 | International Textile Group, Inc. | Flame resistant fabric made from a fiber blend |
US20140076587A1 (en) * | 2012-09-18 | 2014-03-20 | Osmose Holdings, Inc. | Fire retardant device for protecting wooden structures from fire |
US8793814B1 (en) | 2010-02-09 | 2014-08-05 | International Textile Group, Inc. | Flame resistant fabric made from a fiber blend |
US10252200B2 (en) | 2016-02-17 | 2019-04-09 | Hollingsworth & Vose Company | Filter media including a filtration layer comprising synthetic fibers |
US10433593B1 (en) | 2009-08-21 | 2019-10-08 | Elevate Textiles, Inc. | Flame resistant fabric and garment |
US10626289B2 (en) | 2013-09-12 | 2020-04-21 | Bromine Compounds Ltd. | Brominated epoxy polymers as wood coating flame retardant formulations |
US11014030B2 (en) | 2016-02-17 | 2021-05-25 | Hollingsworth & Vose Company | Filter media including flame retardant fibers |
US11434068B2 (en) * | 2008-09-24 | 2022-09-06 | Restaurant Technologies, Inc. | Flame resistant filter apparatus and method |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5418996A (en) * | 1977-07-13 | 1979-02-13 | Ciba Geigy Ag | Stabilized aqueous suspension of bromine containing organic compound containing water insoluble inorganic thickener and application of said suspension to fiber substance to impart fireproofness |
ATE6949T1 (de) * | 1980-04-03 | 1984-04-15 | Geiser A.G. Tenta-Werke | Mittel und verfahren fuer die flammhemmende ausruestung von polyacrylnitrilfasern enthaltendem textilmaterial. |
US7772140B2 (en) * | 2006-03-20 | 2010-08-10 | E.I. du Pont de Nemours and Company Dystar | Ceramic fabrics and methods for making them |
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US2668294A (en) * | 1951-04-02 | 1954-02-09 | Phyllis B Gilpin | Disposable hospital gown |
US2912392A (en) * | 1956-06-27 | 1959-11-10 | Dow Chemical Co | Intumescent coating composition and articles coated therewith |
US3047425A (en) * | 1959-07-16 | 1962-07-31 | Monsanto Chemicals | Method for producing flame and soil resistant acrylic polymer fibers containing carpet fabric |
US3093599A (en) * | 1959-08-22 | 1963-06-11 | Basf Ag | Flameproofed synthetic thermoplastic polymer containing an organic polybromine compound and method of making same |
US3658634A (en) * | 1970-08-20 | 1972-04-25 | Toray Industries | Fire-retardant sheath and core type conjugate fiber |
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US3305431A (en) * | 1960-02-15 | 1967-02-21 | Swift & Co | Flameproofing compositon, method and article containing same |
BE639973A (sv) * | 1962-11-15 | |||
GB1054877A (sv) * | 1963-05-11 | |||
DE1594962A1 (de) * | 1966-11-09 | 1970-03-12 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung nicht entflammbarer gebundener Faservliese |
DE1769913A1 (de) * | 1968-08-05 | 1971-07-15 | Bayer Ag | Flammfeste Textilien |
DE2001125C3 (de) * | 1969-01-13 | 1979-03-22 | Eastman Kodak Co., Rochester, N.Y. (V.St.A.) | Verfahren zur FiammschutzausrUstung von Polyesterfasern |
US3729434A (en) * | 1971-06-28 | 1973-04-24 | Michigan Chem Corp | Method of producing fire retardant emulsions |
-
1972
- 1972-10-25 US US33073172 patent/US3877974A/en not_active Expired - Lifetime
-
1973
- 1973-10-19 CH CH1480573A patent/CH614337GA3/xx unknown
- 1973-10-22 BE BE136927A patent/BE806353A/xx not_active IP Right Cessation
- 1973-10-22 LU LU68656A patent/LU68656A1/xx unknown
- 1973-10-22 DE DE2352923A patent/DE2352923C2/de not_active Expired
- 1973-10-23 AU AU61707/73A patent/AU465965B2/en not_active Expired
- 1973-10-23 SE SE7314388A patent/SE405742B/sv unknown
- 1973-10-23 NL NL7314508A patent/NL172169C/xx not_active IP Right Cessation
- 1973-10-24 CA CA184,142A patent/CA987855A/en not_active Expired
- 1973-10-24 FR FR7338995A patent/FR2204675B1/fr not_active Expired
- 1973-10-24 JP JP11977473A patent/JPS49134772A/ja active Pending
Patent Citations (8)
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US2668294A (en) * | 1951-04-02 | 1954-02-09 | Phyllis B Gilpin | Disposable hospital gown |
US2912392A (en) * | 1956-06-27 | 1959-11-10 | Dow Chemical Co | Intumescent coating composition and articles coated therewith |
US3047425A (en) * | 1959-07-16 | 1962-07-31 | Monsanto Chemicals | Method for producing flame and soil resistant acrylic polymer fibers containing carpet fabric |
US3093599A (en) * | 1959-08-22 | 1963-06-11 | Basf Ag | Flameproofed synthetic thermoplastic polymer containing an organic polybromine compound and method of making same |
US3668155A (en) * | 1968-06-27 | 1972-06-06 | Dow Chemical Co | Self-extinguishing ethylene copolymer foams comprising a ternary mixture of an antimony compound, a halogen-containing compound and a bromine compound |
US3715310A (en) * | 1968-07-17 | 1973-02-06 | Bakelite Xylonite Ltd | Fire-retardant compositions |
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Cited By (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3974310A (en) * | 1972-10-25 | 1976-08-10 | White Chemical Corporation | Flame retardants for synthetic materials (I) |
US3955032A (en) * | 1972-10-25 | 1976-05-04 | White Chemical Corporation | Flame retardants for natural and synthetic materials |
US4087364A (en) * | 1973-01-26 | 1978-05-02 | American Cyanamid Company | Liquid slurry of submicron particles of hexabromobenzene, and process of manufacture |
US4116702A (en) * | 1974-12-13 | 1978-09-26 | Ciba-Geigy Corporation | Agent for flame proofing synthetic fibrous material |
US4113902A (en) * | 1975-05-22 | 1978-09-12 | White Chemical Corporation | Flame retardants for natural and synthetic materials |
US4054715A (en) * | 1975-09-11 | 1977-10-18 | Dixie Yarns, Inc. | Sewing thread containing a flame retardant lubricant |
US4046701A (en) * | 1976-02-23 | 1977-09-06 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
US4154692A (en) * | 1976-04-15 | 1979-05-15 | Mcelveen John B | Flame retardant process, solution and structures |
US4279652A (en) * | 1976-09-15 | 1981-07-21 | Sniaviscosa Societa Nazionale Industria Applicazioni Viscosa, S.P.A. | Self-extinguishing polymers |
US4219605A (en) * | 1976-09-29 | 1980-08-26 | Ciba-Geigy Corporation | Process for flameproofing synthetic fibre material and product |
US4167603A (en) * | 1976-12-13 | 1979-09-11 | Ethyl Corporation | Flame resistant cotton/polyester blend substrates |
US4298509A (en) * | 1977-10-05 | 1981-11-03 | Antonio Fochesato | Noninflammable olefin fibers and method of producing same |
US4151316A (en) * | 1977-11-09 | 1979-04-24 | Chas. S. Tanner Co. | Flameproofing of polyester fabrics using brominated cycloalkanes |
US4178399A (en) * | 1978-02-14 | 1979-12-11 | Chemonic Industries, Inc. | Flame retardant and process |
US4237157A (en) * | 1978-05-05 | 1980-12-02 | Henry Hancock | Process for making fire retardant polypropylene |
EP0038899A1 (en) * | 1980-04-30 | 1981-11-04 | National Aeronautics And Space Administration | Flame retardant elastomeric compositions, heat sealable, flame and abrasion resistant fabrics coated therewith, and process for making same |
US4394413A (en) * | 1981-02-09 | 1983-07-19 | Scapa Dryers, Inc. | Flame retardant dryer fabrics |
US4343854A (en) * | 1981-03-12 | 1982-08-10 | Witco Chemical Corporation | Flame retardant composition |
US4522872A (en) * | 1982-04-12 | 1985-06-11 | Milliken Research Corporation | Industrial fabrics |
US4524170A (en) * | 1983-04-25 | 1985-06-18 | Milliken Research Corporation | Flame retardant finishing composition for synthetic textiles |
US4719256A (en) * | 1984-07-23 | 1988-01-12 | Occidental Chemical Corporation | Fire retardant thermoplastic polyester and polyesterether compositions |
US4695507A (en) * | 1985-05-06 | 1987-09-22 | Burlington Industries, Inc. | Low toxic ceiling board facing |
US4842609A (en) * | 1986-06-05 | 1989-06-27 | Burlington Industries, Inc. | Flame retardant treatments for polyester/cotton fabrics |
USRE34951E (en) * | 1986-08-29 | 1995-05-23 | Interface, Inc. | Flame retardant tufted carpet tile and method of preparing same |
US4750911A (en) * | 1986-09-26 | 1988-06-14 | Burlington Industries, Inc. | Flame-resistant nylon/cotton fabrics |
US4732789A (en) * | 1986-10-28 | 1988-03-22 | Burlington Industries, Inc. | Flame-resistant cotton blend fabrics |
US4961930A (en) * | 1988-04-29 | 1990-10-09 | Weyerhaeuser Company | Pet pad of thermoplastic containing materials with insecticide |
US4900377A (en) * | 1988-04-29 | 1990-02-13 | Weyerhaeuser Company | Method of making a limited life pad |
US4892769A (en) * | 1988-04-29 | 1990-01-09 | Weyerhaeuser Company | Fire resistant thermoplastic material containing absorbent article |
US5438096A (en) * | 1990-09-06 | 1995-08-01 | Great Lakes Chemical Corporation | Flame retardant brominated styrene-based latices |
US5290636A (en) * | 1990-09-06 | 1994-03-01 | Great Lakes Chemical Corp. | Flame retardant brominated styrene-based coatings |
US5484839A (en) * | 1992-11-18 | 1996-01-16 | Great Lakes Chemical Corp. | Flame retardant brominated styrene graft latex compositions |
US5296306A (en) * | 1992-11-18 | 1994-03-22 | Great Lakes Chemical Corp. | Flame retardant brominated styrene graft latex coatings |
US5858159A (en) * | 1995-04-25 | 1999-01-12 | Hoover Universal, Inc. | Method for manufacturing automotive seat assemblies using pre-bonded adhesives |
US11434068B2 (en) * | 2008-09-24 | 2022-09-06 | Restaurant Technologies, Inc. | Flame resistant filter apparatus and method |
US10433593B1 (en) | 2009-08-21 | 2019-10-08 | Elevate Textiles, Inc. | Flame resistant fabric and garment |
US8209785B2 (en) | 2010-02-09 | 2012-07-03 | International Textile Group, Inc. | Flame resistant fabric made from a fiber blend |
US8528120B2 (en) | 2010-02-09 | 2013-09-10 | International Textile Group, Inc. | Flame resistant fabric made from a fiber blend |
US8793814B1 (en) | 2010-02-09 | 2014-08-05 | International Textile Group, Inc. | Flame resistant fabric made from a fiber blend |
US20140076587A1 (en) * | 2012-09-18 | 2014-03-20 | Osmose Holdings, Inc. | Fire retardant device for protecting wooden structures from fire |
US10626289B2 (en) | 2013-09-12 | 2020-04-21 | Bromine Compounds Ltd. | Brominated epoxy polymers as wood coating flame retardant formulations |
US11118084B2 (en) | 2013-09-12 | 2021-09-14 | Bromine Compounds Ltd. | Brominated epoxy polymers as wood coating flame retardant formulations |
US11014030B2 (en) | 2016-02-17 | 2021-05-25 | Hollingsworth & Vose Company | Filter media including flame retardant fibers |
US11123668B2 (en) | 2016-02-17 | 2021-09-21 | Hollingsworth & Vose Company | Filter media including a filtration layer comprising synthetic fibers |
US10252200B2 (en) | 2016-02-17 | 2019-04-09 | Hollingsworth & Vose Company | Filter media including a filtration layer comprising synthetic fibers |
US11738295B2 (en) | 2016-02-17 | 2023-08-29 | Hollingsworth & Vose Company | Filter media including flame retardant fibers |
Also Published As
Publication number | Publication date |
---|---|
NL172169C (nl) | 1988-03-16 |
DE2352923A1 (de) | 1974-05-02 |
AU465965B2 (en) | 1975-10-09 |
JPS49134772A (sv) | 1974-12-25 |
DE2352923C2 (de) | 1987-08-20 |
SE405742B (sv) | 1978-12-27 |
CA987855A (en) | 1976-04-27 |
NL172169B (nl) | 1983-02-16 |
NL7314508A (sv) | 1974-04-29 |
FR2204675A1 (sv) | 1974-05-24 |
FR2204675B1 (sv) | 1979-06-22 |
LU68656A1 (sv) | 1975-06-24 |
BE806353A (fr) | 1974-04-22 |
AU6170773A (en) | 1975-04-24 |
CH614337GA3 (sv) | 1979-11-30 |
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