NO173790B - PROCEDURE FOR AA GIVE A SUBSTANCE OF POLYESTER / COTTON ELLERNYLON / COTTON WASH RESISTANT FLAME RESISTANCE - Google Patents
PROCEDURE FOR AA GIVE A SUBSTANCE OF POLYESTER / COTTON ELLERNYLON / COTTON WASH RESISTANT FLAME RESISTANCE Download PDFInfo
- Publication number
- NO173790B NO173790B NO88882310A NO882310A NO173790B NO 173790 B NO173790 B NO 173790B NO 88882310 A NO88882310 A NO 88882310A NO 882310 A NO882310 A NO 882310A NO 173790 B NO173790 B NO 173790B
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- Prior art keywords
- cotton
- polyester
- nylon
- fabric
- flame retardant
- Prior art date
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- 229920000742 Cotton Polymers 0.000 title claims description 66
- 229920000728 polyester Polymers 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 30
- 239000000126 substance Substances 0.000 title description 17
- 239000004744 fabric Substances 0.000 claims description 45
- 229920001778 nylon Polymers 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- 239000004677 Nylon Substances 0.000 claims description 28
- 239000003063 flame retardant Substances 0.000 claims description 28
- 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 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- -1 cyclic phosphonate ester Chemical class 0.000 claims description 19
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 claims description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 14
- 239000004202 carbamide Substances 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- FAUOSXUSCVJWAY-UHFFFAOYSA-N tetrakis(hydroxymethyl)phosphanium Chemical class OC[P+](CO)(CO)CO FAUOSXUSCVJWAY-UHFFFAOYSA-N 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 claims description 5
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 150000003891 oxalate salts Chemical class 0.000 claims 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- ZGTNBBQKHJMUBI-UHFFFAOYSA-N bis[tetrakis(hydroxymethyl)-lambda5-phosphanyl] sulfate Chemical compound OCP(CO)(CO)(CO)OS(=O)(=O)OP(CO)(CO)(CO)CO ZGTNBBQKHJMUBI-UHFFFAOYSA-N 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 5
- 239000004115 Sodium Silicate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 4
- 229910052911 sodium silicate Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- AKXUUJCMWZFYMV-UHFFFAOYSA-M tetrakis(hydroxymethyl)phosphanium;chloride Chemical compound [Cl-].OC[P+](CO)(CO)CO AKXUUJCMWZFYMV-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- SHRRVNVEOIKVSG-UHFFFAOYSA-N 1,1,2,2,3,3-hexabromocyclododecane Chemical compound BrC1(Br)CCCCCCCCCC(Br)(Br)C1(Br)Br SHRRVNVEOIKVSG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical class OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- BSBSDQUZDZXGFN-UHFFFAOYSA-N cythioate Chemical compound COP(=S)(OC)OC1=CC=C(S(N)(=O)=O)C=C1 BSBSDQUZDZXGFN-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000007706 flame test Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YIEDHPBKGZGLIK-UHFFFAOYSA-L tetrakis(hydroxymethyl)phosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO YIEDHPBKGZGLIK-UHFFFAOYSA-L 0.000 description 1
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 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
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
- D06M15/43—Amino-aldehyde resins modified by phosphorus compounds
- D06M15/431—Amino-aldehyde resins modified by phosphorus compounds by phosphines or phosphine oxides; by oxides or salts of the phosphonium radical
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nonwoven Fabrics (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
Foreliggende oppfinnelse angår fremgangsmåte for å gi et stoff av polyester/bomull eller nylon/bomull vaskebestandig flammemotstandsdyktighet. Nærmere bestemt vedr.ører oppfinnelsen polyester/bomull- og nylon/bomull-blandingsstoffer som under anvendelse av to flammehemmende systemer, ett som er spesifikt for den syntetiske bestanddel og ett som er spesifikt for bomullbestanddelen, har fått en vaskebestandig flammemotstandsdyktighet som vedvarer etter flere vaskinger. The present invention relates to a method for giving a fabric of polyester/cotton or nylon/cotton wash-resistant flame resistance. More specifically, the invention relates to polyester/cotton and nylon/cotton blend fabrics which, using two flame retardant systems, one specific to the synthetic component and one specific to the cotton component, have been given a wash-resistant flame resistance that persists after several washes .
Tidligere forsøk på å oppnå akseptabelt flammemotstandsdyktige polyester/bomull- eller nylon/bomull-blandinger har ikke oppnådd kommersiell suksess. Ingen av behandlingene er praktiske ut fra forbrukerens synspunkt, ettersom de gir stoffer som er svært stive å håndtere. Dette skyldes at det for å oppnå de nødvendige flammehemmende egenskaper er på-krevet med en stor grad av kjemisk pålegging. Denne påleggin-gen gjør stoffet stivt, skjuler fargen på det underliggende stoff og gir ofte stoffet en skarp eller uakseptabel lukt. Dertil er utseendet til de flammemotstandsdyktige stoffene ofte upålitelige. Previous attempts to obtain acceptably flame resistant polyester/cotton or nylon/cotton blends have not met with commercial success. Neither treatment is practical from the consumer's point of view, as they produce fabrics that are very stiff to handle. This is because in order to achieve the necessary flame retardant properties, a large degree of chemical application is required. This application makes the fabric stiff, hides the color of the underlying fabric and often gives the fabric a sharp or unacceptable smell. In addition, the appearance of the flame-resistant materials is often unreliable.
Mesteparten av det tidligere arbeide som er utført på flammemotstandsdyktige polyester/bomull- eller nylon/bomull-blandinger, benyttet et enkelt kjemisk system som var rettet mot bomullbestanddelen i blandingen. Fremgangsmåten var å "lade" stoffene med et flammehemmingsmiddel som var spesifikt for bomull, f.eks. tetrakis-hydroxymethyl-fosfoniumsulfat (THPS). Det var ikke uvanlig for disse tidligere produktene å bruke fra 30 til 35 % festet kjemisk pålegning for at polyester/bomull- eller nylon/bomull-blandingsstoffet skulle kunne passere gjennom en bunnvertikal flammetest. Beklagelig-vis var imidlertid smakfullheten av de ferdige stoffene dår-lig, ettersom de var svært stive å håndtere og hadde et utseende som et belagt stoff. De pålegninger som ble brukt til disse produktene, var langt større enn de teoretisk påkrevde mengder. Most of the previous work done on flame retardant polyester/cotton or nylon/cotton blends used a single chemical system that targeted the cotton component of the blend. The procedure was to "charge" the fabrics with a flame retardant specific to cotton, e.g. tetrakis-hydroxymethyl-phosphonium sulfate (THPS). It was not unusual for these earlier products to use from 30 to 35% fixed chemical application in order for the polyester/cotton or nylon/cotton blend fabric to pass a bottom vertical flame test. Unfortunately, however, the palatability of the finished fabrics was poor, as they were very stiff to handle and had the appearance of a coated fabric. The applications used for these products were far greater than the theoretically required quantities.
Når THPS påføres en polyester/bomull- eller nylon/bomull-blanding, fås det en grad av flammemotstandsdyktighet, men stoffer forblir stivt og generelt uakseptabelt. Ettersom THPS er spesifikt for bomull, reagerer det ikke med polyester-eller nyloninnholdet i stoffet, men tildekker ganske enkelt den syntetiske bestanddel fysisk. Et resultat av dette er at det flammehemmende middel som omgir polyester- eller nylon-fiberen etter flere vaskinger, delvis går tapt. Som en følge av dette, var det ikke uvanlig å bruke så mye som 5,5 % fos-forholdig pålegning for en polyester/bomull-blanding, i det minste til å begynne med, for å komme ut med målet på 3 % av festet fosfor etter 50 vaskinger i varmt vann. When THPS is applied to a polyester/cotton or nylon/cotton blend, a degree of flame resistance is obtained, but fabrics remain stiff and generally unacceptable. As THPS is specific to cotton, it does not react with the polyester or nylon content of the fabric, but simply physically covers the synthetic component. A result of this is that the flame retardant that surrounds the polyester or nylon fiber after several washings is partially lost. As a result, it was not uncommon for a polyester/cotton blend to use as much as 5.5% phos ratio application, at least initially, to come out with the target of 3% of the fix phosphorus after 50 washes in hot water.
For tiden markedsføres det to THP-baserte flammehem-mersystemer for denne type behandling. "Pyroset TPO" er et THPS/urea-forkondensat av tetrakis-(hydroxymethyl)fosfoniumsulfat og urea, mens "Retardol AC" er et THPC/urea-prepolymer-kondensat av tetrakis-(hydroxymethyl)fosfoniumklorid og urea. Two THP-based flame retardant systems are currently marketed for this type of treatment. "Pyroset TPO" is a THPS/urea pre-condensate of tetrakis-(hydroxymethyl)phosphonium sulfate and urea, while "Retardol AC" is a THPC/urea prepolymer condensate of tetrakis-(hydroxymethyl)phosphonium chloride and urea.
Fremgangsmåten for å tilføre flammemotstandsdyktighet til 100 % bomullstoffer under anvendelse av THPC/urea ("Retardol AC") er kjent som "Proban"-prosessen. Selve THP-salt/urea-forkondensat-prosessen er beskrevet i de følgende US patentskrifter nr. 4.078.101, 4.145.463, 4.311.855 og 4.494.951. Denne fremgangsmåten anses som effektiv for å tilføre flammemotstandsdyktighet til 100 % bomullstoffer, men markedsføres ikke for polyester/bomull-blandinger eller nylon/bomull-blandinger. THP-salt/urea-forkondensat-prosessen er i seg selv ineffektiv til å gi tilstrekkelig beskyttelse av polyester/bomull-blandinger inneholdende mer enn 35-40% polyester. The process of adding flame retardancy to 100% cotton fabrics using THPC/urea ("Retardol AC") is known as the "Proban" process. The actual THP-salt/urea-precondensate process is described in the following US Patents Nos. 4,078,101, 4,145,463, 4,311,855 and 4,494,951. This process is considered effective for adding flame retardancy to 100% cotton fabrics, but is not marketed for polyester/cotton blends or nylon/cotton blends. The THP salt/urea precondensate process is itself ineffective in providing adequate protection for polyester/cotton blends containing more than 35-40% polyester.
I 1970-årene ble polyester/bomull-blandinger flam-mehemmet ved å bruke tris-2,3-dibrompropylfosfat ("Tris") i kombinasjon med THPS. "Tris" ble imidlertid funnet å være et carcinogen og ble trukket tilbake fra markedet slik at det i dag ikke selges noen blanding av polyester og bomull med over-veiende innhold av polyester som er blitt behandlet med flammehemmende kjemikalier. Et mål med foreliggende oppfinnelse er å fremstille godtagbare flammemotstandsdyktige polyester/bomull- og nylon/bomull-blandinger ved å bruke flere flammehemmende kjemikalier eller kjemiske systemer, og å anvende behandlingsbetingelser eller hjelpestoffer som gir et kommer-sielt godtagbart, tiltrekkende produkt med god farge og godtagbare håndteringsegenskaper. In the 1970s, polyester/cotton blends were flame retardant using tris-2,3-dibromopropyl phosphate ("Tris") in combination with THPS. However, "Tris" was found to be a carcinogen and was withdrawn from the market so that today no blend of polyester and cotton with a predominant content of polyester that has been treated with flame retardant chemicals is sold. An aim of the present invention is to produce acceptable flame-resistant polyester/cotton and nylon/cotton blends by using several flame-retardant chemicals or chemical systems, and to use processing conditions or auxiliaries that provide a commercially acceptable, attractive product with good color and acceptable handling characteristics.
Med foreliggende oppfinnelse tilveiebringes det såle-des en fremgangsmåte i to trinn for å gi et stoff bestående av polyester/bomull eller nylon/bomull vaskebestandig flammemotstandsdyktighet som vedvarer etter flere vaskinger. Fremgangsmåten er kjennetegnet ved at: (a) et polyester/bomull- eller et nylon/bomull-blan-dingsstoff tilføres en flammehemmende mengde av et prepolymer-kondensat av urea og en tetrakis-(hydroxymethyl)fosfoniumsalt-flammehemmer som fester seg til bomullfibrene, det prepolymer-kondensat-holdige stoff eksponeres mot en kilde for ammoniakk, hvorved det dannes en ammoniert prepolymer, deretter oxyderes den ammonierte prepolymer, hvorved det dannes et flammehemmende polymernettverk i bomullfiberstrukturen, og (b) polyester/bomull- eller nylon/bomull-blandings-stof fet tilføres en flammehemmende mengde av (1) en syklisk fosfonatester- eller (2) hexabromsyklododecan-flammehemmer som fester seg til polyester- eller nylonfibrene, og stoffet herdes ved forhøyede temperaturer slik at den tilførte sykliske fosfonatester eller hexabromsyklododecan festes til polyester-eller nylonfibrene. The present invention thus provides a two-step method for giving a fabric consisting of polyester/cotton or nylon/cotton wash-resistant flame resistance which persists after several washings. The method is characterized in that: (a) a polyester/cotton or a nylon/cotton blend fabric is supplied with a flame retardant amount of a prepolymer condensate of urea and a tetrakis-(hydroxymethyl)phosphonium salt flame retardant which adheres to the cotton fibers, exposing the prepolymer condensate-containing fabric to a source of ammonia, forming an ammoniated prepolymer, then oxidizing the ammoniated prepolymer, forming a flame-retardant polymer network in the cotton fiber structure, and (b) polyester/cotton or nylon/cotton blends -substance fat is added with a flame retardant amount of (1) a cyclic phosphonate ester or (2) hexabromocyclododecane flame retardant which attaches to the polyester or nylon fibers, and the fabric is cured at elevated temperatures so that the added cyclic phosphonate ester or hexabromocyclododecane attaches to the polyester or the nylon fibers.
Uttrykket "polyester" betegner høypolymere, hovedsakelig rettkjedede polyesterharpikser fremstilt ved omsetning mellom en dicarboxylsyre eller en dicarboxylsyreester og en diol i nærvær av en forestringskatalysator eller en ester-ut-byttingskatalysator. Egnede dicarboxylsyrer er malon-, rav-, adipin-, azelain-, malein-, fumar-, hydromucon-, isoftal-, terefthal- og syklohexan-dicarboxylsyrer. Representative dio-ler er ethylenglycol, propylenglycol, butylenglycol og 1,6-hexandiol. (Se US patentskrifter nr. 2.465.319 og 2.901.446.) Den polyester som ble anvendt i utførelses-eksemplene som følger nedenfor, var polyethylenterefthalat. The term "polyester" denotes high polymer, mainly straight chain polyester resins prepared by reaction between a dicarboxylic acid or a dicarboxylic acid ester and a diol in the presence of an esterification catalyst or an ester exchange catalyst. Suitable dicarboxylic acids are malonic, succinic, adipic, azelaic, maleic, fumaric, hydromuconic, isophthalic, terephthalic and cyclohexane dicarboxylic acids. Representative diols are ethylene glycol, propylene glycol, butylene glycol and 1,6-hexanediol. (See US Patent Nos. 2,465,319 and 2,901,446.) The polyester used in the embodiments that follow below was polyethylene terephthalate.
Uttrykket "nylon" betegner en fabrikert fiber hvor de fiberdannende stoffer er langkjedede, syntetiske polyamider med gjentatte polyamidgrupper (-CONH-) i polymerkjeden. Disse polyamidene dannes fra forskjellige kombinasjoner av disyrer, diaminer og aminosyrer. (Se generelt Kirk-Otmer Encyclopedia of Chemical Technology, vol. 16, 1968, Interscience, New York, s. 1-105. The term "nylon" denotes a manufactured fiber where the fiber-forming substances are long-chain, synthetic polyamides with repeated polyamide groups (-CONH-) in the polymer chain. These polyamides are formed from different combinations of diacids, diamines and amino acids. (See generally Kirk-Otmer Encyclopedia of Chemical Technology, vol. 16, 1968, Interscience, New York, pp. 1-105.
Polyester/bomull- og nylon/bomull-fibermaterialene som behandles ved fremgangsmåten ifølge oppfinnelsen, kan være på et hvilket som helst ønsket trinn av bearbeiding, dvs. at de kan behandles som vevde eller strikkede stoffer, farget eller ufarget, eller som tekstiler som allerede er blitt viderebehandlet. The polyester/cotton and nylon/cotton fiber materials treated by the process according to the invention can be at any desired stage of processing, i.e. they can be treated as woven or knitted fabrics, dyed or undyed, or as textiles which have already has been further processed.
Polyester/bomull-blandingene behandlet i henhold til foreliggende fremgangsmåte, inneholder mellom 35 og 80 % polyester, idet resten er bomull. Nylon/bomull-blandingene inneholder mellom 10 og 65 % nylon eller fortrinnsvis fra 35 til 55 % nylon. The polyester/cotton mixtures treated according to the present method contain between 35 and 80% polyester, the remainder being cotton. The nylon/cotton blends contain between 10 and 65% nylon or preferably from 35 to 55% nylon.
Flammehemmende egenskaper tilføres stoffet i to forskjellige trinn, ett for bomullbestanddelen og det andre for den syntetiske bestanddel (polyester eller nylon). Den rekke-følge som disse trinnene utføres i, er ikke av avgjørende be-tydning; gode resultater kan oppnås selv om bomullbestanddelen i blandingen behandles enten først eller sist. Flame retardant properties are added to the fabric in two different stages, one for the cotton component and the other for the synthetic component (polyester or nylon). The order in which these steps are carried out is not of decisive importance; good results can be obtained even if the cotton component of the mixture is treated either first or last.
I. Behandling av bomullbestanddelen i syntetisk fiber/- I. Treatment of the cotton component in synthetic fiber/-
bomull-blandingen. the cotton blend.
Flammemotstand tilføres bomullbestanddelen i blandingen av syntetisk fiber og bomull ved å impregnere stoffet med en vandig oppløsning som inneholder et forkondensat av en nøyak-tig utmålt mengde av urea (NH2-CONH2) og et tetrakis-(hydroxymethyl)-fosfoniumsalt (THP), betegnet som THPS når saltet er sulfatet [ (HOCH2)4P+]2S04=, og THPC når saltet er kloridet; oxa-latet og fosfatsaltene er også kjent. THP-salt/ureaforkonden-satet påføres stoffet og tørkes til et bestemt fuktighetsnivå. Deretter omsettes det med ammoniakk på stoffet, vanligvis ammoniakkgass, under kontrollerte betingelser, hvorved det dannes en ammoniert flammehemmer som i sin tur oxyderes, vanligvis med hydrogenperoxyd, hvorved det dannes et tredimensjo-nalt flammehemmerpolymernettverk i bomullfiberstrukturen. Denne prosessen resulterer i et stoff som er mykere å håndtere enn etter andre behandlinger, slik som THPS/urea som er til-bøyelig til å forbli på utsiden av fibrene og gjøre fibrene stive, og som lettere fjernes ved gjentatt vasking. Flame resistance is imparted to the cotton component of the synthetic fiber/cotton blend by impregnating the fabric with an aqueous solution containing a pre-condensate of a precisely measured amount of urea (NH2-CONH2) and a tetrakis-(hydroxymethyl)-phosphonium salt (THP), designated as THPS when the salt is the sulfate [ (HOCH2)4P+]2S04=, and THPC when the salt is the chloride; the oxalate and the phosphate salts are also known. The THP salt/urea condensate is applied to the fabric and dried to a specific moisture level. The substance is then reacted with ammonia, usually ammonia gas, under controlled conditions, whereby an ammoniated flame retardant is formed which in turn is oxidized, usually with hydrogen peroxide, whereby a three-dimensional flame retardant polymer network is formed in the cotton fiber structure. This process results in a fabric that is softer to handle than after other treatments, such as THPS/urea, which tends to remain on the outside of the fibers and stiffen the fibers, and is more easily removed by repeated washing.
Tetrakis-(hydroxymethyl)fosfoniumklorid/urea-for-polymerkondensat/(THPC/urea) er tilgjengelig under navnet "Retardol AC". Et beslektet kjemikalium, THPS/urea-for-polymerkondensat, er tilgjengelig under navnet "Pyroset TPO". II. Behandling av polyester- og nylonbestanddelen i blandingen. Tetrakis-(hydroxymethyl)phosphonium chloride/urea for polymer condensate/(THPC/urea) is available under the name "Retardol AC". A related chemical, THPS/urea-for-polymer condensate, is available under the name "Pyroset TPO". II. Treatment of the polyester and nylon component in the mixture.
En av de følgende omtalte flammehemmere kan anvendes til polyester- eller nylonbestanddelen i blandingen. One of the flame retardants mentioned below can be used for the polyester or nylon component in the mixture.
Hexabromsyklododecan smelter ved ca. 182 °C, og når det påføres som en dispersjon på et polyester/bomull- eller nylon/bomull-stoff ved temperaturer over smeltepunktet og deretter avkjøles, smelter hexabromsyklododecanet til fiberen og gir den flammemotstandsegenskaper. Hexabromocyclododecane melts at approx. 182 °C, and when applied as a dispersion to a polyester/cotton or nylon/cotton fabric at temperatures above the melting point and then cooled, the hexabromocyclododecane fuses to the fiber and imparts flame retardant properties.
Hexabromsyklododecan er et syklisk alkylbromid med empirisk formel C12H18Br6, CAS-registreringsnummer 25637-99-4, sammensatt av hexabromsyklododecan og beslektede bromsyklo-alkaner. Det er et luktfritt, vannuoppløselig, grå-hvitt pulver med et smeltepunktområde på 142-182 °C, og anvendes fortrinnsvis ved fremgangsmåten ifølge oppfinnelsen som en dispersjon i vann eller i et vandig påføringsbad. Hexabromocyclododecane is a cyclic alkyl bromide with empirical formula C12H18Br6, CAS registry number 25637-99-4, composed of hexabromocyclododecane and related bromocycloalkanes. It is an odorless, water-insoluble, grey-white powder with a melting point range of 142-182 °C, and is preferably used in the method according to the invention as a dispersion in water or in an aqueous application bath.
Hexabromsyklododecan er tilgjengelig som CD-75 og som "Saytex HBCD". Det anvendes primært som en flammehemmer for plast, delvis på grunn av dens dårlige oppløselighet i oppløs-ningsmidler som vanligvis brukes til tekstilbéarbeiding. Hexabromocyclododecane is available as CD-75 and as "Saytex HBCD". It is used primarily as a flame retardant for plastics, partly due to its poor solubility in solvents that are usually used for textile processing.
Et annet flammehemmende materiale som anvendes i henhold til foreliggende oppfinnelse, er en varmestabil, ringfor-met fosfonatester fremstilt ved å omsette alkylhalogenfrie estere med et bisyklisk fosfitt. Som klasse er disse sykliske fosfonatesterne representert ved en av formlene: hvor a er 0 eller 1, b er 0, 1 eller 2, c er 1, 2 eller 3, og a+b+c er 3, R og R' er like eller forskjellige og er alkylCCi.g), fenyl, halogenfenyl, hydroxyfenyl, tolyl, xylyl, benzyl, fenethyl, hydroxyethyl, fenoxyethyl eller dibromfenoxymethyl, R2er alkyl(C1.4), og R3 er lavere alkylCC,^) eller hydroxyalkyl(C^), eller Another flame retardant material used in accordance with the present invention is a heat-stable, ring-shaped phosphonate ester produced by reacting alkyl halogen-free esters with a bicyclic phosphite. As a class, these cyclic phosphonate esters are represented by one of the formulas: where a is 0 or 1, b is 0, 1 or 2, c is 1, 2 or 3, and a+b+c is 3, R and R' are equal or different and are alkylCCi.g), phenyl, halophenyl, hydroxyphenyl, tolyl, xylyl, benzyl, phenethyl, hydroxyethyl, phenoxyethyl or dibromophenoxymethyl, R2 is alkyl(C1.4), and R3 is lower alkylCC,^) or hydroxyalkyl(C^ ), or
hvor d er 0, 1 eller 2, e er 1, 2 eller 3, R<2>er alkylCC^), R<3>er lavere alkylCC^) eller hydroxyalkyl (), R4 er alkyl () fenyl, halogenfenyl, hydroxyfenyl, hydroxyethyl, fenoxyethyl, dibromfenoxymethyl, tolyl, xylyl, benzyl eller fenethyl, og R<5>er monovalent alky1(Cj.g) , klorfeny1, bromfeny1, dibromfenyl, tribromfenyl, hydroxyfenyl, nafthyl, tolyl, xylyl, benzyl eller fenethyl, divalent alkylen(Cx_6), vinylen, o-fenyl, m-fenylen, p-fenylen, tetraklorfenylen (o,m,p) eller tetrabromfenylen (o, m eller p) eller trivalent fenyl. where d is 0, 1 or 2, e is 1, 2 or 3, R<2> is alkylCC^), R<3> is lower alkylCC^) or hydroxyalkyl (), R4 is alkyl () phenyl, halophenyl, hydroxyphenyl , hydroxyethyl, phenoxyethyl, dibromophenoxymethyl, tolyl, xylyl, benzyl or phenethyl, and R<5>is monovalent alkyl1(Cj.g) , chlorophenyl1, bromophenyl1, dibromophenyl, tribromophenyl, hydroxyphenyl, naphthyl, tolyl, xylyl, benzyl or phenethyl, divalent alkylene(Cx_6), vinylene, o-phenylene, m-phenylene, p-phenylene, tetrachlorophenylene (o,m,p) or tetrabromophenylene (o,m or p) or trivalent phenyl.
De foretrukne forbindelser har formelen: The preferred compounds have the formula:
hvor X er 0 eller 1, og er vanligvis en 50:50 blanding av mono- og diesterne. Fremstillingen av disse sykliske fos-fonatestere og deres anvendelse som flammehemmere er beskrevet i US patentskrifter nr. 3.789.091 og 3.849.368. where X is 0 or 1, and is usually a 50:50 mixture of the mono- and diesters. The preparation of these cyclic phosphonate esters and their use as flame retardants is described in US Patent Nos. 3,789,091 and 3,849,368.
En syklisk fosfonatester som er tilgjengelig som en luktfri, viskøs væske (viskositet 250 Pa.s) med et flammepunkt på 171 °C (ASTM D-93), er "Antiblaze 19T". A cyclic phosphonate ester available as an odorless, viscous liquid (viscosity 250 Pa.s) with a flash point of 171°C (ASTM D-93) is "Antiblaze 19T".
Håndfølelsen av de behandlede stoffer kan forbedres enda mer ved å utføre herdeoperasjonen i et fuktig miljø med høy luktfuktighet. The hand feel of the treated fabrics can be improved even more by carrying out the curing operation in a humid environment with a high odor humidity.
Testmetoder for flammemotstandsdyktighet. Test methods for flame resistance.
Følgende fremgangsmåte for testing ble brukt: The following procedure for testing was used:
FR Federal Test Method 5903 er ment for anvendelse ved bestemmelse av klærs motstandsdyktighet overfor flamme- og glødespredning og tilbøyelighet til forkulling. Et rektangu-lært prøvestykke av tøy (70 mm x 120 mm) med lengderetningen parallelt med rennings- eller appreteringsretningen, plasseres i en holder og henges vertikalt opp i et skap med den nedre ende 1,9 cm over toppen av en Fisher gassbrenner. En syntetisk gassblanding bestående hovedsakelig av hydrogen og methan, tilføres brenneren. Etter at prøven er oppmontert i skapet og døren lukket, påsettes brennerflammen vertikalt midt på den nedre kant av prøven i 12 sekunder. Prøven fortsetter å brenne etter at brenneren er slukket. Den tid i sekunder som prøven fortsetter å gløde etter at prøven har sluttet å brenne, rap-porteres som etterglødningstid; dersom prøven gløder i mer enn 30 sekunder, fjernes den fra testskapet, idet man passer på å ikke få gloen til å flamme opp, og henges opp i et trekkfritt område i den samme vertikale stilling som i testskapet. For-kullingslengde, avstanden (i centimeter) fra enden av prøven som ble eksponert mot flammen, til enden av en langsgående flenge gjennom midten av det forkullede område til det høyeste punkt i det forkullede område, måles også. Fem eksemplarer fra hver prøve måles vanligvis, og gjennomsnittet av resultatene regnes ut. FR Federal Test Method 5903 is intended for use in determining clothing's resistance to flame and glow spread and charring tendency. A rectangular leather test piece of fabric (70 mm x 120 mm) with the longitudinal direction parallel to the warp or finishing direction is placed in a holder and suspended vertically in a cabinet with the lower end 1.9 cm above the top of a Fisher gas burner. A synthetic gas mixture consisting mainly of hydrogen and methane is fed to the burner. After the sample has been mounted in the cabinet and the door closed, the burner flame is applied vertically in the middle of the lower edge of the sample for 12 seconds. The sample continues to burn after the burner is extinguished. The time in seconds that the sample continues to glow after the sample has stopped burning is reported as the afterglow time; if the sample glows for more than 30 seconds, it is removed from the test cabinet, taking care not to cause the glow to flare up, and suspended in a draft-free area in the same vertical position as in the test cabinet. Charring length, the distance (in centimeters) from the end of the sample exposed to the flame, to the end of a longitudinal slit through the center of the charred area to the highest point of the charred area, is also measured. Five specimens from each sample are usually measured and the results averaged.
Eksempel IA Example IA
Stofftypen 9886 (50/50 nylon/bomull) ble tilført et våtopptak på 61 % med "Pyroset TPO" (THPS-urea-forkondensat, se badformel) og varmet opp ved 54 °C i 48 sekunder. Vann-innholdet ble funnet å være 15,5-16 % målt med et Mahlo-meter. Stoffet ble ekvilibrert i en plastpose i 1-2 timer. Stoffet ble så eksponert mot ammoniakkgass ved et molforhold på 6:1 ammoniakk:fosfor. Oxydasjon av stoffet ved hjelp av en hydrogenperoxyd/natriumsilikatoppløsning fulgte. Mengden av peroxyd som ble brukt, var 5 % basert på vekten av stoffet. Natrium-silikatet ble brukt for å opprettholde en pH på 9-9,5. Stoffet ble skyllet og trommeltørket. Fabric type 9886 (50/50 nylon/cotton) was added to a wet absorption of 61% with "Pyroset TPO" (THPS urea pre-condensate, see bath formula) and heated at 54°C for 48 seconds. The water content was found to be 15.5-16% measured with a Mahlo meter. The substance was equilibrated in a plastic bag for 1-2 hours. The material was then exposed to ammonia gas at a molar ratio of 6:1 ammonia:phosphorus. Oxidation of the substance using a hydrogen peroxide/sodium silicate solution followed. The amount of peroxide used was 5% based on the weight of the fabric. The sodium silicate was used to maintain a pH of 9-9.5. The fabric was rinsed and tumble dried.
Badformel: Bath formula:
Det TPO/ammoniakk-behandlede stoff av type 9886 ble deretter tilført en 15 % "Antiblaze 19" oppløsning, varmet opp i en ovn ved 193 °C i 45 sekunder og testet med hensyn på flammemotstandsdyktighet i ferdigbehandlet form og etter 25 vaskinger. The Type 9886 TPO/ammonia treated fabric was then added to a 15% "Antiblaze 19" solution, heated in an oven at 193°C for 45 seconds and tested for flame retardancy in finished form and after 25 washes.
Eksempel IB Example IB
Det TPO/ammoniakk-behandlede stoff av type 9886 ifølge eksempel IA ble også deretter tilført en 15 % dispersjon av hexabromsyklododecan (HBCD), varmet opp ved 182 °C i 45 sekunder og testet med hensyn på flammemotstandsdyktighet i ferdigbehandlet form og etter 25 vaskinger. The TPO/ammonia-treated fabric of type 9886 according to Example IA was also then added to a 15% dispersion of hexabromocyclododecane (HBCD), heated at 182°C for 45 seconds and tested for flame resistance in finished form and after 25 washes.
Ingen av de behandlede stoffer ifølge eksempel IA eller IB oppviste hverken etterflamming eller ettergløding. Resultatene viser et høyt nivå av flammemotstandsdyktighet, og de behandlede stoffene hadde tilfredsstilende egenskaper med hensyn til utseende. None of the treated substances according to example IA or IB showed either afterflame or afterglow. The results show a high level of flame resistance and the treated fabrics had satisfactory properties in terms of appearance.
Eksempel 2 Example 2
I lignende forsøk som eksempel 1, ble 65/35 polyester/bomull-stoff, type 9798, og 40/60 polyester/bomull-stoff, type 9496, tilført "Pyroset TPO", se badformel. Stoffene ble tørket til 16-16,5 % vanninnhold målt med et Mahlo-meter. Stoffene ble så eksponert mot ammoniakkgass ved et molforhold >6:1 ammoniakk:fosfor. Oxydasjon av stoffet ved hjelp av en hydrogenperoxyd/natriumsilikat-oppløsning fulgte. Mengden av peroxyd som ble brukt, var 5 % basert på vekten av stoff.Natriumsilikatet ble brukt til å opprettholde en pH på 9-9,5. Stoffet ble skyllet og trommeltørket. In similar experiments to example 1, 65/35 polyester/cotton fabric, type 9798, and 40/60 polyester/cotton fabric, type 9496, were added "Pyroset TPO", see bath formula. The materials were dried to 16-16.5% water content measured with a Mahlo meter. The substances were then exposed to ammonia gas at a molar ratio of >6:1 ammonia:phosphorus. Oxidation of the substance using a hydrogen peroxide/sodium silicate solution followed. The amount of peroxide used was 5% based on the weight of fabric. The sodium silicate was used to maintain a pH of 9-9.5. The fabric was rinsed and tumble dried.
"Aerotex H" er et kationisk produkt med ikke-ioniske og anioniske rester, og er inkludert i påførings-badblandingen "Aerotex H" is a cationic product with non-ionic and anionic residues, and is included in the application bath mixture
som mykner. which softens.
Badformel: Bath formula:
Begge TPO/ammoniakk-behandlede stoffer ble deretter tilført en 15 % dispersjon av hexabromsyklododecan (HBCD), varmet opp ved 182 °C i 45 sekunder og testet med hensyn på flammemotstandsdyktighet i ferdigbehandlet form og etter 25 vaskinger. Both TPO/ammonia treated fabrics were then added to a 15% dispersion of hexabromocyclododecane (HBCD), heated at 182°C for 45 seconds and tested for flame retardancy in finished form and after 25 washes.
Ingen av de testede prøver oppviste hverken etterflamming eller ettergløding, og de korte forkullingslengder indikerer en høy grad av flammemotstandsdyktighet. De behandlede stoffer var tilfredsstillende å ta på og hadde et tilfredsstillende utseende. None of the tested samples showed either afterflame or afterburning, and the short charring lengths indicate a high degree of flame resistance. The treated fabrics were satisfactory to the touch and had a satisfactory appearance.
Claims (15)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/911,720 US4750911A (en) | 1986-09-26 | 1986-09-26 | Flame-resistant nylon/cotton fabrics |
| US06/923,965 US4732789A (en) | 1986-10-28 | 1986-10-28 | Flame-resistant cotton blend fabrics |
| PCT/US1987/002432 WO1988002283A1 (en) | 1986-09-26 | 1987-09-25 | Flame-resistant cotton blend fabrics |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO882310D0 NO882310D0 (en) | 1988-05-25 |
| NO882310L NO882310L (en) | 1988-07-25 |
| NO173790B true NO173790B (en) | 1993-10-25 |
| NO173790C NO173790C (en) | 1994-02-02 |
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ID=27129582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO882310A NO173790C (en) | 1986-09-26 | 1988-05-25 | Procedure for Providing a Fabric of Polyester / Cotton Wash Resistant Flame Resistance |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0325610B1 (en) |
| JP (1) | JPH02500454A (en) |
| AU (1) | AU603391B2 (en) |
| DE (1) | DE3789553D1 (en) |
| DK (1) | DK289288D0 (en) |
| NO (1) | NO173790C (en) |
| WO (1) | WO1988002283A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8900060D0 (en) * | 1989-01-04 | 1989-03-01 | Albright & Wilson | Flame retardant composition |
| US5074994A (en) * | 1990-10-18 | 1991-12-24 | The Doe Run Company | Sequential and selective flotation of sulfide ores |
| JP3948620B2 (en) * | 2003-06-20 | 2007-07-25 | 三洋化成工業株式会社 | Flame retardant for polyester synthetic fiber |
| EP3786349B1 (en) | 2019-08-29 | 2022-06-01 | Ecoatech GmbH | Flame retardant treatment of absorbent substrates |
| EP3892772A1 (en) | 2020-04-06 | 2021-10-13 | Ecoatech GmbH | Flame retardant finishing of textile fabrics with polycondensation products |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1317468A (en) * | 1969-09-30 | 1973-05-16 | Cotton Producers Inst | Process for rendering cellulosic textile material flame retardant |
| US3974310A (en) * | 1972-10-25 | 1976-08-10 | White Chemical Corporation | Flame retardants for synthetic materials (I) |
| JPS51116299A (en) * | 1975-04-03 | 1976-10-13 | Teijin Ltd | Flame proofing of polyester and cellulose blended cloth |
| JPS5218800A (en) * | 1975-08-05 | 1977-02-12 | Toyobo Co Ltd | Process for preparing condensation products containing phosphorus |
| IT1080551B (en) * | 1976-02-23 | 1985-05-16 | Velsicol Chemical Corp | LONG-LASTING FLAME RETARDERS FOR TEXTILE MATERIALS |
| JPS54106693A (en) * | 1978-02-06 | 1979-08-21 | Meisei Chemical Works Ltd | Flame proofing and water repellent finish of synthetic fiber product |
| US4448817A (en) * | 1981-01-06 | 1984-05-15 | Wool Development International Limited | Textile finishing of keratinous articles |
| ZA826861B (en) * | 1981-09-28 | 1983-07-27 | Albright & Wilson | Flameproofing textiles |
| JPH0657912B2 (en) * | 1984-03-16 | 1994-08-03 | 東レ株式会社 | Flame retardant fiber composite |
| JPS60259674A (en) * | 1984-06-07 | 1985-12-21 | 帝人株式会社 | Polyester fiber product and its production |
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1987
- 1987-09-25 JP JP62506118A patent/JPH02500454A/en active Pending
- 1987-09-25 WO PCT/US1987/002432 patent/WO1988002283A1/en active IP Right Grant
- 1987-09-25 DE DE87906715T patent/DE3789553D1/en not_active Expired - Lifetime
- 1987-09-25 AU AU80716/87A patent/AU603391B2/en not_active Ceased
- 1987-09-25 EP EP87906715A patent/EP0325610B1/en not_active Expired - Lifetime
-
1988
- 1988-05-25 NO NO882310A patent/NO173790C/en unknown
- 1988-05-26 DK DK289288A patent/DK289288D0/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0325610B1 (en) | 1994-04-06 |
| DE3789553D1 (en) | 1994-05-11 |
| NO882310L (en) | 1988-07-25 |
| DK289288A (en) | 1988-05-26 |
| EP0325610A4 (en) | 1991-04-10 |
| NO882310D0 (en) | 1988-05-25 |
| AU8071687A (en) | 1988-04-21 |
| AU603391B2 (en) | 1990-11-15 |
| EP0325610A1 (en) | 1989-08-02 |
| DK289288D0 (en) | 1988-05-26 |
| JPH02500454A (en) | 1990-02-15 |
| WO1988002283A1 (en) | 1988-04-07 |
| NO173790C (en) | 1994-02-02 |
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