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( 12 ) United States Patent ( 10 ) Patent No.: US 10,640,893 B2 Sarzotti Et Al

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( 12 ) United States Patent ( 10 ) Patent No.: US 10,640,893 B2 Sarzotti Et Al US010640893B2 ( 12 ) United States Patent ( 10 ) Patent No.: US 10,640,893 B2 Sarzotti et al. (45 ) Date of Patent : May 5 , 2020 ( 54 ) FLAME RETARDANT FIBERS, YARNS, AND (58 ) Field of Classification Search FABRICS MADE THEREFROM CPC Y10T 442/696 ; Y10T 442/68 ; D02G 3/44 ( 75 ) Inventors: Deborah M. Sarzotti, Kingston (CA ) ; (Continued ) Thomas E. Schmitt, Concord , NC (US ) ; Andrew W. Briggs, Kingston (56 ) References Cited (CA ) U.S. PATENT DOCUMENTS ( 73 ) Assignee : INVISTA North America S.a.r.l. , 4,970,255 A 11/1990 Reimann et al. Wilmington , DE (US ) 5,356,700 A * 10/1994 Tanaka DO2G 3/047 ( * ) Notice : Subject to any disclaimer , the term of this 139/420 R patent is extended or adjusted under 35 (Continued ) U.S.C. 154 ( b ) by 823 days. FOREIGN PATENT DOCUMENTS (21 ) Appl. No .: 13 /825,209 CA 2078626 C 4/1999 CN 1201474 A 12/1998 ( 22 ) PCT Filed : Sep. 21, 2011 ( Continued ) ( 86 ) PCT No.: PCT/ US2011 / 052557 OTHER PUBLICATIONS $ 371 ( c ) ( 1 ) , (2 ), ( 4 ) Date : May 22 , 2013 Deopura , B.L., Alagirusamy, R., Joshi, M. and Gupta , B., Polyesters and Polyamides , 2008 , p . 320 , Woodhead Publishing Limited , (87 ) PCT Pub . No .: WO2012/ 040332 Cambridge. PCT Pub . Date :Mar. 29 , 2012 ( Continued ) (65 ) Prior Publication Data Primary Examiner Peter Y Choi US 2013/0244527 A1 Sep. 19 , 2013 (74 ) Attorney , Agent, or Firm — Invista North America Related U.S. Application Data S.a.r.1 . (60 ) Provisional application No. 61/ 385,614 , filed on Sep. 23 , 2010 . ( 57 ) ABSTRACT Disclosed are technical fibers and yarns made with partially ( 51 ) Int . Ci. aromatic polyamides and non -halogenated flame retardant DO2G 3/44 ( 2006.01 ) additives. Fabrics made from such fibers and yarns demon DOIF 6/60 ( 2006.01 ) strate superior flame retardancy over traditional flame retar ( Continued ) dant nylon 6,6 fabrics . Further , the disclosed fibers and ( 52 ) U.S. CI. yarns , when blended with other flame retardant fibers, do not CPC D02G 3/443 ( 2013.01) ; DOIF 1/07 demonstrate the dangerous “ scaffolding effect common ( 2013.01 ) ; DO1F 67605 ( 2013.01 ) ; D04H 1/42 with flame retardant nylon 6,6 blended fabrics . ( 2013.01 ) ; (Continued ) 13 Claims, 5 Drawing Sheets Nylon / FR Rayon Fabric FR Outgases Polymei Melt Flow Zone + Combustion Zone ResidualChar US 10,640,893 B2 Page 2 (51 ) Int. Ci. FOREIGN PATENT DOCUMENTS DOIF 1/07 ( 2006.01 ) CN 1950455 A 4/2007 D04H 1/4342 ( 2012.01 ) CN 101166852 A 4/2008 D04H 1/4382 (2012.01 ) CN 101611182 A 12/2009 D04H 1/42 ( 2012.01 ) CN 101754998 A 6/2010 EP 0559128 9/1993 (52 ) U.S. CI. EP 2096199 9/2009 ??? D04H 1/4342 ( 2013.01 ) ; D04H 1/4382 JP H02-127466 A 5/1990 JP 2703390 B2 1/1998 ( 2013.01 ); DIOB 2331/021 ( 2013.01 ) ; YIOT JP H10-280230 A 10/1998 428/249921 ( 2015.04 ) ; Y10T 428/2904 JP 2000303257 10/2000 ( 2015.01) ; YIOT 442/68 (2015.04 ) ; YIOT JP 2000-328363 A 11/2000 442/681 ( 2015.04 ) ; Y10T 4427696 ( 2015.04 ) JP 2001234066 A 8/2001 JP 2003-105659 A 4/2003 (58 ) Field of Classification Search JP 2007-500803 A 1/2007 USPC 442/302 , 414 , 301 KR 93-9831 B1 10/1993 See application file for complete search history . TW 200538499 A 12/2005 TW 200613448 A 5/2006 TW 200617097 A 6/2006 WO 2005095685 Al 10/2005 ( 56 ) References Cited WO 2009/101930 A1 8/2009 U.S. PATENT DOCUMENTS OTHER PUBLICATIONS 6,184,282 B1 2/2001 Gareiss et al. 6,225,383 B1 * 5/2001 Hirono CO8K 5/34928 Horrocks, Richard A., Price , Dennis . Fire Retardant Materials , 148 524/100 $ 4.5.2 , 2001 , CRC Press , Boca Raton . 6,255,371 B1 * 7/2001 Schlosser CO8K 5/34928 “ Fabric Flame Retardant Treatment” , Cotton , Incorporated . Cary , 252/609 NC ( 2003 ) . 6,342,548 B2 * 1/2002 Flippo CO8K 5/3492 International Preliminary Report on Patentability received for PCT 524/100 Patent Application No. PCT/US2011 /052557 dated Apr. 4 , 2013 , 6 2004/0076824 A1 * 4/2004 Urabe DO1F 1/07 pages . 428/375 International Search Report received for PCT Patent Application 2006/0266986 Al * 11/2006 Day DO1F 1/07 No. PCT/ US2011 / 052557 dated May 2 , 2012 , 3 pages . 252/608 Written Opinion received for PCT Patent Application No. PCT / 2007/0148455 A1 6/2007 Ke US2011/ 052557 dated May 2 , 2012 , 4 pages . 2008/0057807 A1 * 3/2008 Tutterow A41D 31/0022 442/1 * cited by examiner U.S. Patent May 5 , 2020 Sheet 1 of 5 US 10,640,893 B2 FIG 1a FIG 1b 2961-190-15 CONTROL 300S - 166-15 w / SCRIM PA - MXD6 , W /SCRIM FIG 1c FIG 1d 3005-15-7 300S- 16-13 10 % MC IN PA66 / 70 % MC W / SERUM PA - MXD w / scen U.S. Patent May 5 , 2020 Sheet 2 of 5 US 10,640,893 B2 FIG 1e FIG 1f 3005-153 10 % MPP IN PA 66 3005. 166-9 wl Super 10 % MPP in PA - MXDU1 , W / SCRIM FIG 19 FIG 1h 3005-16 -27 3005 - 7 - 26 10 % DEPZN » PAU 10 % DEPZN IN Serim PAMXDO /SCRIM U.S. Patent May 5 , 2020 Sheet 3 of 5 US 10,640,893 B2 FIG . 2 Nylon / FR Rayon Fabric FR Outgases Polymer Melt flow zone H combustion Zone Residual Char U.S. Patent May 5 , 2020 Sheet 4 of 5 US 10,640,893 B2 FIG . 3a FIG . 3b 50/50 10 % MPP in nylon - 6,6 / FR rayon 50/50 10 % MPP in MXDO / FR rayon FIG . 3c FIG . 3d 50/50 10 % DEPAI in nylon -6,6 /FR rayon 50/50 10 % DEPAI in MXD6 / FR rayon U.S. Patent May 5 , 2020 Sheet 5 of 5 US 10,640,893 B2 FIG . 4 200 DEPAL in PA66 180 XMPP in PA66 A MC in PA66 160 DEPZN in PA66 SITA in PA66 140 PA66 DEPAL in PA -MXD6 120 X MPP in PA -MXD6 after-flametime(s) MC in PA -MXD6 100 O DEPZN in PA -MXD6 SITA in PA -MXD6 80 O PA -MXD6 60 40 20 0 0 2 4 6 8 10 12 14 16 18 20 additive loading (wt % ) DEPZn : Diethyl phosphinate , zinc salt DEPAI: Diethyl phosphinate , aluminum salt MC : Melamine cyanurate SITA : Silicotungstic acid US 10,640,893 B2 1 2 FLAME RETARDANT FIBERS , YARNS, AND and Alagirusamy state in their recent book Polyesters and FABRICS MADE THEREFROM Polyamides ( The Textile Institute 2008 at page 320 ) that “ [ i] t seems unlikely that there will be any major breakthroughs FIELD OF THE INVENTION with regard to new and / or improved reactive flame- retardant 5 comonomers or conventional ... flame retardant additives The invention relates to technical fibers , yarns , and fabrics for use in ... nylon fibers . " in general, and in particular , to flame retardant fibers , yarns, and fabrics made therefrom comprising partially aromatic SUMMARY OF THE INVENTION polyamides and non -halogenated flame retardant additives . 10 The problem with using blends of thermoplastic fibers BACKGROUND OF THE TECHNOLOGY with non -melting flame resistant fibers (e.g. aliphatic poly amides and FR treated cotton ) is the so - called “ scaffolding Flame retardant (FR ) fabrics are crucial in both military effect .” (See Horrocks et al. , Fire Retardant Materials at anders, nonand - military petro - chemical environments workers . Firefighters are just , arace few car of driv the 15 148, 8 4.5.2 ( 2001) ) . In general, thermoplastic fibers, includ non -military groups that benefit from the added protection of ing those treated or modified with FR agents , self -extinguish flame retardant fabrics. However, the true benefit of flame by shrinking away from the flame source or when molten retardant fabrics lies with the military. In addition to the polymer drips away from the flame source and extinguishes. unforgiving surroundings that our military troops must oper FR polyester fiber is a fiber with such behavior . When FR ate in , the advent of unconventional modern warfare creates 20 polyester fiber is blended with a non -melting flame retardant an even more hostile environment . Specifically , the use of fiber, such as FR - treated cotton , the non -melting fiber forms improvised explosive devices (“ IEDs” ) to immobilize large a carbonaceous scaffold ( the “ scaffolding effect ” ) and the convoys of soldiers makes individual troop protection criti thermoplastic FR polyester fiber is constrained in the flame cally important. and will continue to burn . In essence, during vertical flam In addition to ballistic fabrics and body armor, flame 25 mability testing, the thermoplastic fiber polymer melts and retardant fabrics serve a crucial role in protecting soldiers runs down the non - thermoplastic scrim and feeds the flame from IEDs. IEDs are constructed of numerous materials (e.g. and the fabric burns completely . Additionally , in clothing, high -explosive charges , flammable liquids, shrapnel, etc.) , the molten polymer can drip and stick to human skin and some acting as projectiles and others acting as incendiaries results in additional injuries to the wearer. upon detonation . Thus, military fabrics must be of varied 30 What is needed is improved flame retardant nylon blends construction to handle the multitude of threats from an IED . that eliminate the “ scaffolding effect " , provide good flame There are basically two types of flame retardant fabrics retardancy, prevent dripping and sticking , and are wear used in protective clothing : ( 1 ) Fabrics made from flame resistant . Therefore , it is desirable to find a combination of retardant organic fibers ( e.g. aramid , flame retardant rayon , melt - processed polymer that can be blended with flame polybenzimidazole , modacrylic , etc. ) ; and (2 ) Flame retar- 35 retardant additives into a fiber that can be knit or woven or dant fabrics made from conventional materials ( e.g.
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