US3681124A - Process for preparing durable flame-retardant synthetic-cellulosic fabric blends - Google Patents

Process for preparing durable flame-retardant synthetic-cellulosic fabric blends Download PDF

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US3681124A
US3681124A US3681124DA US3681124A US 3681124 A US3681124 A US 3681124A US 3681124D A US3681124D A US 3681124DA US 3681124 A US3681124 A US 3681124A
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fabric
polyester
percent
polyethylene glycol
flame
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Stephen B Sello
Paul H Egrie
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JP Stevens and Co Inc
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JP Stevens and Co Inc
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Assigned to BANKERS TRUST COMPANY, A NY BANKING CORP. reassignment BANKERS TRUST COMPANY, A NY BANKING CORP. SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: J.P. STEVENS & CO.
Assigned to J.P. STEVENS & CO., INC. reassignment J.P. STEVENS & CO., INC. RELEASE SECURITY INTEREST & ASSIGNMENT. Assignors: BANKERS TRUST COMPANY
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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
    • 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
    • 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
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]
    • 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
    • Y10T442/2672—Phosphorus containing
    • Y10T442/268—Phosphorus and nitrogen containing compound

Definitions

  • the fatty acid ester of polyethylene glycol serves both to soften the fabric and to carry fireproofing reaction products onto the polyester component.
  • This invention relates to an improved process for treating textile materials which are blends of cellulosic and polyester fibers so as to cause fibers of both those classifications to be flame retardant concurrently.
  • polyester-cotton blends are one of the more common types of fabrics in current use, there is a paucity in the art of conferring fire resistance to such blends.
  • blended polyester-cotton is unusual, inasmuch as fabrics solely of polyester fiber normally meet specifications for flame retardancy, such as the Vertical Test of the American Association of Textile Chemists and Colorists, AATCC 34-1966, without the addition of a fire retardant finish.
  • flame retardancy such as the Vertical Test of the American Association of Textile Chemists and Colorists, AATCC 34-1966
  • the resulting product is quite flammable and does not meet flame retardancy specifications. This is due to the fact that when 100 percent polyester fabric is exposed to a flame, the polyester melts and drips away largely unburned, while on exposure of a blended fabric of polyester and flame-resistant cotton to a flame, the cotton prevents the polyester from dripping away.
  • cellulosic-polyester blends are obtained without the necessity of applying a separate, polyester flame retardant such as tris(2,3-dibromopropyl) phos phate and without unduly deteriorating physical properties or imparting objectionable stiifness.
  • the cellulosic-polyester blended fabrics are rendered durably flame retardant by impregnating with (A) tetrakis(hydroxymethyl)phosphonium chloride and urea or a precondensate of these reactants,
  • reaction product containing melamine a fatty acid ester of polyethylene glycol and forming insoluble reaction products on said fabric. It is essential that the reaction product containing melamine be insolubilized in the presence of moisture such as by steam curing.
  • System A Tetrakis (hydroxymethyl)phosphonium chloride and urea or a precondensate of these reactants
  • System B Melamine-formaldehyde reaction product or a melamine-formaldehyde-methanol reaction product
  • System C An ester derived from polyethylene glycol and a higher aliphatic carboxylic acid
  • All of the components of Chemical Systems A, B and C can be applied and then the desired insoluble products formed simultaneously, thus, for instance, all of the chemicals can be applied from a single bath such as by padding from an aqueous dispersion, and then the desired insoluble products formed simultaneously in a single curing step.
  • the polyethylene glycol ester of System C can be added to the fabric, along with the chemicals of System B, an insoluble product formed by curing and then the chemicals of System A added and insolubilized.
  • the chemicals of System A can be added and insolubilized and then the polyethylene glycol ester of System C can be added to the fabric along with the chemicals of System B, and insoluble products formed by curing.
  • the compounds of System A form an insoluble product containing bound phosphorus and bound nitrogen.
  • the insoluble product can be formed by the reaction on the fabric of tetrakis(hydroxymethyl)phosphonium chloride and urea.
  • a precondensate of tetrakis (hydroxymethyl)phosphonium chloride and urea which is subsequently further reacted.
  • Procedures for preparing such precondensates are described by Reeves et al. US. Pat. 2,812,311 and Coates U.S. Pat. 2,983,623. The following equation illustrates the formation of a suitable precondensate:
  • the component of System B is an N-methylol derivative of melamine having from two to six methylol groups or a methyl ether derived from such an N-methylol compound wherein the sum of CH OH groups and -CH OCH groups is from two to six.
  • the N-methylol compounds can be prepared by reacting melamine with two or more moles of formaldehyde according to known procedures.
  • the methyl ethers can be prepared by known procedures by reacting the N-methylol compounds with methanol or coreacting melamine, formaldehyde and methanol.
  • the components of System B cannot be insolubilized by dry heat, but rather wet fixation procedures must be used.
  • wet fixation the components of System B are formed into an insoluble product while the moisture content of said fabric is at least 20 percent based on the weight of the fabric.
  • Wet fixation is preferably accomplished by contacting the impregnated fabric with steam.
  • wet fixation can be carried out at lower temperatures by maintaining the fabric in a moist environment at a temperature and for a period of time sufiicient to form an insoluble product.
  • the fabric can be impregnated with an aqueous solution of N-methylolmelamine, the fabric wrapped in polyethylene while a substantial amount of water remains in the fabric, and the wrapped fabric stored at a temperature of at least 20 C. until the desired degree of insolubilization is reached.
  • System C represents a critical feature of the invention, and stems from the discovery that a particular type of adjunct makes it possible to impart flame retardancy simultaneously to both cellulosic and polyester fibers without causing objectionable stiffness of the treated fabric, the adjunct being a higher aliphatic carboxylic ester derived from polyethylene glycol.
  • Suitable polyethylene glycol esters have the formula A(OCH CH OA' wherein A is an acyl group derived from a saturated or unsaturated aliphatic monocarboxylic acid of 8-24 carbon atoms;
  • A is hydrogen or an acyl group derived from a saturated or unsaturated aliphatic monocarboxylic acid of 63-24 carbon atoms
  • n is an integer of from about 4 to 80.
  • Oleic acid is the preferred acid for making the esters, which include both di-esters as well as mono-esters. Particularly outstanding results are obtained with polyethylene glycol monooleate.
  • suitable acids are palmitoleic, lauric, myristic, palm'itic, stearic, and arachidic acids.
  • Useful polyethylene glycols for making the esters have the formula wherein m is 4 to 80.
  • Blends of two or more of such products as are illustrated in Table A may be used in making the ester which is to serve in System C of the process of this invention.
  • a blend of equal parts of polyethylene glycols 300 and 1540 is particularly useful.
  • Major species in that particular blend (conventionally designated as polyethylene glycol 1500) are
  • the nonreactive fatty esters of polyethylene glycol are key factors in accomplishing the following two crucial objectives:
  • incorporation of the soluble ester composition of this invention into a pad bath of one or more of the flame-retardant ingredients, and the subsequent formation of the flame-retardant finish provides an effective durable flame-retardant treatment for blends without the problem of excessive stiffness.
  • the nonreactive fatty esters of polyethylene glycol make it possible to attain desirably high add-ons of bound nitrogen (4 to 7 percent) and phosphorus (2 to 4 percent) with a balanced distribution on both cellulosic and noncellulosic components of the synthetic-cellulosic fabric blend.
  • nonreactive esters of polyethylene glycol are quite specific in bringing about the beneficial effects discussed above. Closely related derivatives, such as polyethylene glycols or their monoesters, having a methoxy group in place of a terminal hydroxy group are hardly effective in meaningful control of stiffness.
  • the present invention can be used with cellulose-polyester blended fabrics containing from to 90 percent cellulose and from about 90 to 10 percent polyester.
  • Suitable commercial blended fabrics are: polyester 20% and cotton 80%, polyester 35% and cotton 65%, polyester 50% and cotton 50%, polyester 65% and cotton 35%, polyester 80% and cotton 20%, and polyester 65% and regenerated cellulose (as viscose rayon) 35%.
  • the invention is applicable likewise to other ratios, and to blends having fiber types in addition to cellulosic and polyester types, such as the blend consisting of polyester 37%, cotton 35%, and spandex 28%.
  • Cellulose fibers include those made from (a) seed hairs, e.g., cotton, (b) bast fibers such as flax (linen), and (c) rayon and modified rayons.
  • Examples 1-3 illustrate the ability of the polyethylene glycol esters employed in the present invention to prevent undue stiffening of the treated cellulosepolyester blended fabrics, while the remaining examples illustrate the methods of the present invention for rendering such blended fabrics flame retardant. In the examples percents and parts are by weight unless otherwise specified.
  • Bound Phosphorus, P Determined by Kjeldahl digestion followed by colorimetric analysis employing acetonewasher, 5-pound load, full cycle, 60 C., synthetic detergent; tumble drying.
  • PEG Polyethylene glycol
  • THPC Tetrakis(hydroxymethyl)phosphonium chloride
  • TMM Trimethylolmelamine, (s-triazine 2,4,6 triyltriimino trimethanol.
  • EXAMPLE 1 This example provides a comparison of the extents to which various additives derived from polyethylene glycols aflFect stiffness of a polyester-cellulose blend on which trimethylolmelamine is insolubilized by steaming.
  • the substrate fabric was -50 polyester-cotton poplin suiting weighing 6.24 ounces per square yard, and having a thread count (warp by filling) of 129 by 49 per inch. Its stiffness was 550 milligram-centimeters in the warp direction. Samples were padded with an aqueous solution of trimethylolmelamine (28% hydrogen peroxide (0.3%), and an additive (polyethylene glycol derivative) present in the percentage shown in the accompanying table. (For the control sample, only the additive Was omitted.) The wet pickup was 72-81%. Then the samples were dried at room temperature (approximately 21 C.) to a moisture content of 20%. While on a frame, samples were steamed for 8 minutes. They were then washed in warm water, framed to original dimensions, dried in an oven at 105 C., and reweighed. Results of observations and calculations are shown in the accompanying table.
  • EXAMPLE 2 This is a variation of Example 1 using less trimethylolmelamine.
  • Example 1 The procedure of Example 1 was repeated, but trimethylolmelamine was applied from a 20% solution (instead of 28%). Results of measurements are shown in the accompanying table.
  • the pressure of the pad rolls was adjusted to give a wet pickup of 71 to 74%
  • the padded fabric was partially dried in air to a moisture content of (25 i5 Then it was wrapped in polyethylene foil to prevent loss of moisture, and stored at 41 C. for 72 hours to effect wet fixation. Next, the fabric was rinsed in hot water, then in cold water, and dried in a forced-air oven at 105 C. Results are in the accompanying table.
  • the fabric used was 50-50 polyester cotton suiting in a plain weave, weighing 6.71 ounces per square yard, and having a thread count (warp by filling) of 74 by 37 per inch. It was padded (to a wet pickup of 78%) using an aqueous pad bath having respectively 14.4%, 7.0%, and 28.9% of each of the following components: trimethylolmelamine, polyethylene glycol 1500 monoleate, and (ureylenedimethylene)bis[tris(hydroxymethyl)phosphonium] dichloride. The latter compound had been made by a condensation reaction involving tetrakis(hydroxymethyl)phosphonium chloride (2 moles) and urea (1 mole). Prior to padding, the pH of the pad bath had been raised to 6 by the addition of a relatively small quantity of N,N',N"-nitrilotriethanol.
  • the fabric was dried at approximately 71 C. on a pin frame. Then the pin frame with the fabric on it was placed horizontally in a chamber designed for steaming. Steam at approximately 102 C. was introduced, and the fabric was exposed to it for 30 seconds. Next, the fabric was rinsed according to the rinsing procedure described in Example 4. Then the treated fa-bric blend was dried on a frame at 105 C. Data in the accompanying table demonstrate that this suiting fabric had durable flame retardance. Note that the fabric had been impregnated with (ureylenedimethylene)bis[tris(hydroxymethyl)phosphoniu-m] dichloride, trimethylolmelamine, and polyethylene glycol monooleate in the relative amounts by weight of approximately 4, 2, and '1, respectively.
  • EXAMPLE 6 This example consists of a variation of Example 4.
  • Example 4 The steps of Example 4 were applied to 50-50 polyester-cotton sheeting in a plain weave and Weighing 3.67 ounces per square yard. The warp-by-filling count was 101 by 81 threads per inch.
  • a sample was padded with an aqueous solution of tn'methylolmelamine (20%), hydrogen peroxide (0.3%), and polyethylene glycol 1500 monooleate (8.0%), and processed by wet fixation as in Example 4.
  • the same precondensate as in Example 4 was used (the pad bath having been adjusted to pH 6 by a relatively small quantity of N,N',N-nitrilotriethanol). The sample was processed as in Example 4. Results are in the accompanying table.
  • Step 1 consisted of padding on the precondensate of Example 4 (after the pad bath had been adjusted to pH 6 by addition of N,N, N"-nitrilotriethanol), followed by curing as in Example 4.
  • Step 2 consisted of padding with an aqueous solution of trimethylolmelamine (20%), hydrogen peroxide (0.3%), and polyethylene glycol 1500 monooleate (8.0% and processing by wet fixation as in Example 4. Results are in the accompanying table.
  • EXAMPLE 8 TABLE FOR EXAMPLE 8 N, percent from TMM pretreatment 5.2 2:125 THPC:urea precondensate, percent OWF 23.6 Weight gain, percent, after curing, washing and drying 13.9 Char length, inches (Vertical Flame Test):
  • EXAMPLE 9 This example provides a comparison of the relative effectiveness of polyethylene glycol monooleate and tris- (2,3-dibromopropyl)phosphate in the single-step process involving brief steaming to impart durable flame retardance on a synthetic cellulosic blend.
  • the single-step padding process was applied to the 50-50 polyester-cotton suiting described in Example 5.
  • the compositions of the pad baths (and other variables) are shown in the accompanying table. Tris(2,3-dibromopropyl)phosphate was in emulsified form. Prior to padding, the pH of each pad bath was raised to 5 by the addition of a relatively small quantity of N,N',N"-nitrilotriethanol. The wet pickup of the ingredients was 70 to 73%.
  • the padded samples were dried at approximately 71 C. on a pin frame and then the pin frame with the fabric on it was placed horizontally in a chamber designed for steaming. Steam at approximately 102 C. was introduced, and the fabric was exposed to it for 4 minutes. Next, the fabric was rinsed according to the rinsing procedure described in Example 4 and then dried on a frame at 105 C. Data in the accompanying table demonstrate that this suiting fabric had durable flame retardance.
  • polyethylene glycol monooleate Based on char lengths in the vertical flame tests, particularly after numerous launderings, polyethylene glycol monooleate is comparable in effectiveness with tris(2,3- dibromopropyl) phosphate, a commonly used brominated additive to augment the flame retardancy of such blends. Moreover, when polyethylene glycol 1500 monooleate was used, the weight gain (after rinsing and drying) was 18.8%, definitely less than the weight gain of 23.0% when tris(2,3-dibromopropyl) phosphate was used. Inasmuch as polyethylene glycol 1500 monooleate is a nonreactive additive, it is not insolubilized on the fibers.
  • a process for treating cellulose-p0 yester blended EXAMPLE fabric to render said fabric flame retardant said process This example illustrates wet fixation of bound nitrogen in the pretreatment step, and insolubilization of bound 10 (a) ilepregnatmg, said fabnc with componel, A phosphorus-nitrogen by ammonia in the next step.
  • the pad bath was at pH 2.2.
  • the sample was 1 ester of h formula A( CH CH QA' partially dried and then exposed to ammonia vapor for h i 10 minutes at PP y NeXt, the Sample was A is an acyl group derived from an aliphatic monorinsed by the multiple IlIlSlIlg PIOCfidllI described ill carboxylic acid of from 8 24 carbon atoms; Example 4. Results are in the accompanying table.
  • A is hydrogen or an acyl group derived from an TABLE FOR EXAMP 1 aliphatic monocarboxylic acid of from 8-24 carbon atoms, and m is an integer of from 4 to 80, percent from TMM
  • Pretreatment said polyethylene glycol ester being impregnated into said 2:1.THPQmma precondsnsate Percent E fabric prior to the insolubilization of said melamine WFIght Percent after.was.hlng and drymg 109 derivative, in an amount sufficient to reduce the stiffness stlflness 'f (warp ,ilrectlon) 890 of the treated fabric and said fabric being dried after the Char length Inches (Vemcal Flama Test): insolubilization of the melamine derivative in the presence Before laundering 4.4 40 of moisture After 10 laundemfgs 2.
  • a pr s d clam r sald Example 5 is epeatgd with the exception that trimethamine der vative is insolubilized on said fabric in the pres ylolmelamine is replaced by a melamine-formaldehyde @Ilce Q saldpolyethylene glycol P to lmpregnat' reaction product made from substantially 6 moles of form- 3 Sald fabrlc Wlth Q P Q aldehyde and 3 moles of methanol per mole of melamine.
  • THPC Urea TMM, PEG 1500 Percent Oharlength Polyester-cotton precondensate, percent monooleate, Weight sheeting percent OWF OWF percent OWF gain Orig. 10L 25L After rinsing and drying.
  • a flame retardant cellulose-polyester blended fabric produced by the process of claim 1.

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  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US3681124D 1970-02-02 1970-02-02 Process for preparing durable flame-retardant synthetic-cellulosic fabric blends Expired - Lifetime US3681124A (en)

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CA (1) CA931437A (enrdf_load_stackoverflow)
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DE (1) DE2104823A1 (enrdf_load_stackoverflow)
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3855349A (en) * 1971-03-22 1974-12-17 Toyo Boseki Method and composition for imparting fire-proofness to synthetic shaped articles
US3874911A (en) * 1972-01-14 1975-04-01 Ciba Geigy Ag Process for the manufacture of phosphorus-containing condensation products, the products and their use as flameproofing agents
US3901985A (en) * 1971-09-10 1975-08-26 Ciba Geigy Ag Process for the manufacture of condensation products containing phosphorus, the products and their use as flameproofing agents
US4162275A (en) * 1973-07-26 1979-07-24 E. I. Du Pont De Nemours And Company Flame-resistant fiber
US4935286A (en) * 1985-11-01 1990-06-19 Armstrong World Industries, Inc. Stain and scratch resistant resilient surface coverings
US20060178064A1 (en) * 2001-11-07 2006-08-10 Balthes Garry E Fire retardant panel composition and methods of making the same
US20060182940A1 (en) * 2005-02-14 2006-08-17 Hni Technologies Inc. Fire-resistant fiber-containing article and method of manufacture
US20070116991A1 (en) * 2004-12-17 2007-05-24 Balthes Garry E Fire retardant panel composition and methods of making same
US20100136334A1 (en) * 2008-12-02 2010-06-03 Israeli Processing Co., Ltd. Fire Retardant Thread and Method of Manufacture
WO2024054489A3 (en) * 2022-09-06 2024-04-18 Natural Alternatives, Llc Fire retardant formulations and methods of use
WO2024089696A1 (en) * 2022-10-27 2024-05-02 Bromine Compounds Ltd. Flame retardant system for cellulose-based textiles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0284200B1 (en) * 1987-03-24 1992-12-02 Komatsu Seiren Co., Ltd. Method for treatment of fibrous materials

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3855349A (en) * 1971-03-22 1974-12-17 Toyo Boseki Method and composition for imparting fire-proofness to synthetic shaped articles
US3901985A (en) * 1971-09-10 1975-08-26 Ciba Geigy Ag Process for the manufacture of condensation products containing phosphorus, the products and their use as flameproofing agents
US3874911A (en) * 1972-01-14 1975-04-01 Ciba Geigy Ag Process for the manufacture of phosphorus-containing condensation products, the products and their use as flameproofing agents
US4162275A (en) * 1973-07-26 1979-07-24 E. I. Du Pont De Nemours And Company Flame-resistant fiber
US4935286A (en) * 1985-11-01 1990-06-19 Armstrong World Industries, Inc. Stain and scratch resistant resilient surface coverings
US20060178064A1 (en) * 2001-11-07 2006-08-10 Balthes Garry E Fire retardant panel composition and methods of making the same
US8012889B2 (en) 2001-11-07 2011-09-06 Flexform Technologies, Llc Fire retardant panel composition and methods of making the same
US7906176B2 (en) 2004-12-17 2011-03-15 Flexform Technologies, Llc Methods of manufacturing a fire retardant structural board
US20070116991A1 (en) * 2004-12-17 2007-05-24 Balthes Garry E Fire retardant panel composition and methods of making same
US20060182940A1 (en) * 2005-02-14 2006-08-17 Hni Technologies Inc. Fire-resistant fiber-containing article and method of manufacture
US20060252323A1 (en) * 2005-02-14 2006-11-09 Hni Technologies Inc. Fiber-containing article and method of manufacture
US20100136334A1 (en) * 2008-12-02 2010-06-03 Israeli Processing Co., Ltd. Fire Retardant Thread and Method of Manufacture
WO2024054489A3 (en) * 2022-09-06 2024-04-18 Natural Alternatives, Llc Fire retardant formulations and methods of use
WO2024089696A1 (en) * 2022-10-27 2024-05-02 Bromine Compounds Ltd. Flame retardant system for cellulose-based textiles

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CH546854A (enrdf_load_stackoverflow) 1974-03-15
GB1326288A (en) 1973-08-08
DE2104823A1 (de) 1971-08-26
CH149271A4 (enrdf_load_stackoverflow) 1973-08-31
CA931437A (en) 1973-08-07

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