US3888779A - Flame retardant composition containing tetrakis (hydroxymethyl) phosphonium oxalate - Google Patents
Flame retardant composition containing tetrakis (hydroxymethyl) phosphonium oxalate Download PDFInfo
- Publication number
- US3888779A US3888779A US317998A US31799872A US3888779A US 3888779 A US3888779 A US 3888779A US 317998 A US317998 A US 317998A US 31799872 A US31799872 A US 31799872A US 3888779 A US3888779 A US 3888779A
- Authority
- US
- United States
- Prior art keywords
- hydroxymethyl
- tetrakis
- urea
- flame retardant
- phosphonium
- 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 24
- ZYNUSOWWGMTZHH-UHFFFAOYSA-L oxalate;tetrakis(hydroxymethyl)phosphanium Chemical compound [O-]C(=O)C([O-])=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO ZYNUSOWWGMTZHH-UHFFFAOYSA-L 0.000 title claims abstract description 24
- 239000003063 flame retardant Substances 0.000 title claims description 17
- 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 title claims description 15
- 239000000463 material Substances 0.000 claims abstract description 24
- 239000004753 textile Substances 0.000 claims abstract description 23
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000004202 carbamide Substances 0.000 claims abstract description 17
- 229920002678 cellulose Polymers 0.000 claims abstract description 4
- 239000001913 cellulose Substances 0.000 claims abstract description 4
- -1 HYDROGEN ATOMS Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 239000011574 phosphorus Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 12
- 239000007864 aqueous solution Substances 0.000 abstract description 6
- 229920000877 Melamine resin Polymers 0.000 abstract description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000376 reactant Substances 0.000 abstract description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 17
- 239000004744 fabric Substances 0.000 description 17
- 235000013877 carbamide Nutrition 0.000 description 14
- 235000014786 phosphorus Nutrition 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000004900 laundering Methods 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- VELJAQNIUXJKSV-UHFFFAOYSA-M tetrakis(hydroxymethyl)phosphanium;acetate Chemical compound CC([O-])=O.OC[P+](CO)(CO)CO VELJAQNIUXJKSV-UHFFFAOYSA-M 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- ZTBDCHNXDHUMCJ-UHFFFAOYSA-K tetrakis(hydroxymethyl)phosphanium;phosphate Chemical compound [O-]P([O-])([O-])=O.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO.OC[P+](CO)(CO)CO ZTBDCHNXDHUMCJ-UHFFFAOYSA-K 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AKTDWFLTNDPLCH-UHFFFAOYSA-N 1,1,3,3-tetrakis(hydroxymethyl)urea Chemical compound OCN(CO)C(=O)N(CO)CO AKTDWFLTNDPLCH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical class OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- SUPOBRXPULIDDX-UHFFFAOYSA-N [[4-amino-6-(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound NC1=NC(NCO)=NC(NCO)=N1 SUPOBRXPULIDDX-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical class O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- RDBMUARQWLPMNW-UHFFFAOYSA-N phosphanylmethanol Chemical compound OCP RDBMUARQWLPMNW-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 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
- 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
Definitions
- Phosphonium salts of the formula (HOCH P C- H OH.X wherein X is an anion are used in flame retardant finishes.
- Tetrakis(hydroxymethyl)phosphonium chloride (THPC) is a component of some flame retardant finishes for textile materials.
- THP tris(hydroxymethyl)phosphine
- the treated textile materials have flame retardant properties which are durable to repeated laundering but the finishes impart a stiff, boardy hand and cause an objectionable and sometimes severe strength loss in the treated fabric. Textile tensile strength, tear strength and abrasion resistance are reduced.
- My invention provides a flame retardant finish for cellulosic textile materials which imparts a soft hand to the material, i.e., it does not make the material stiff; the materials treated with the finish are durable to repeated laundering; and the finish does not reduce the resistance of fabric to wear.
- U.S. Pat. No. 2,937,207 teaches a process for manufacturing tetrakis(hydroxymethyl)phosphonium oxalate.
- the patent suggests that the products obtained according to the process of the invention can be used as flame-proofing agents for textiles and woods.
- my Example 4 below, when tetrakis(hydroxymethyl)phosphonium oxalate is used alone on fabric, the fabric burns even before laundering.
- the invention is a process for imparting durable flame retardant properties and a soft hand to cellulosic textile materials by applying an aqueous finish solution of tetrakis(hydroxymethyl)phosphonium oxalate and at least 1 organic nitrogenous compound having a trivalent nitrogen bearing at least 2 members comprised of hydrogen atoms and methylol groups, for example, urea, a melamine or a water soluble methylolated nitrogenous celluose reactant or mixtures thereof to the textile material and heating the textile material to effect a cure of the finish thereon; the finish compositions and the cel-lulosic textile material produced by my pro- DETAILED DESCRIPTION I have discovered that when an aqueous solution containing tetrakis(hydroxymethyl)phosphonium oxalate (TKS) and a nitrogenous compound having trivalent nitrogen bearing at least 2 hydrogen atoms or methylol groups is applied to cellulosic textile materials, the materials become flame
- aqueous solutions of tetrakis(hydroxymethyl)- phosphonium oxalate can be prepared by reacting in aqueous medium 1 mol of tris(hydroxymethyl)- phosphine with at least 1 mole of formaldehyde and essentially one-half mole of oxalic acid.
- Sufficient oxalic acid is used to provide between 0.3 and 1.0 moles, preferably between 0.4 and 0.6 moles, of real oxalic acid per mole of THP.
- the formaldehyde should be used in an amount sufficient to provide one mole of formaldehyde per mole of THP.
- the formaldehyde can be in the form of an aqueous solution or as paraformaldehyde.
- the temperature of the mixture is held at about 30C. for about 4 hours.
- the reaction temperature should be between 20C. and C., preferably between 25C. and 50C.
- the product is an aqueous solution which can be used in preparing the flame retardant finishes.
- the finish may contain free formaldehyde and oxalic acid.
- the amount of TKS'present in the product depends on the amount of TH? used initially. Each mole of the THP requiries by theory 0.5 moles ,of oxalic acid and one mole of formaldehyde. For each mole of TKS formed, the amount of THF in the product is reduced by two moles.
- the application-solutions are prepared by diluting the aqueous solution of TKS in water to a given concentration of solids and adding urea or a urea formaldehyde condensate in sufficient amount to provide about 1.25 moles prescribed above of urea and/or ureaformaldehyde condensate per mole of phosphonium salts.
- concentration phosphorus and urea in the application solutions will depend, in general, on the method of application, the amount of phosphorus and urea to be applied to the textile material, and on the weight, structure and fiber composition of the textile material.
- the nitrogenous compounds of use in this invention include the organic amido compounds which are conventionally employed in the form of their methylol derivatives as thermosetting aminoplast textile finishes. They include the melamines, urea, cyclic ureas, carbamates, triazinones, etc., and their methylol and alkylated methylol derivatives.
- the preferred nitrogenous compound is urea.
- Representative methylol compounds include monomethylol urea, dimethylol urea, tetramethylol urea, dimethylol melamine, partially methylated trimethylol melamine, and the like. Combinations of'two or more nitrogenous compounds may be employed.
- Sufficient flame retardant finish should be applied to cellulosic textile-material to provide between about 1% and 6%, preferably between about 2% and 4% of phosphorus based on the weight of the textilematerial.
- Sufficient nitrogenous compound is used to provide between about 1% and preferablybetween about 2% and 6% of nitrogen based on the weight of the textile material.
- the ratio of nitro derived phosphorus on a parts by weight basis is between 0.5 and 5.0 preferably between 0.7 and 2.0.
- the cellulose textile material ishould contain at least 20% cellulosic fibers.
- cellulosic fibers it is meant such fibers as cotton, regenerated cellulose (rayon), linen, jute, etc.
- the components of the flame retardant compositions temperaturebetween about i67-350F. or higher.
- - drying time'can range from several minutes at the lower temperature to asbriefly as seconds atthe higher tem- I perature. .
- the finish is then cured at a temperature of between about248--392F. preferably between about 300-350F.
- the time required for curing the finish is between I and'5 minutes, depending on the tempera ture and the weight and structure of the textilemate rial.
- compositions and. processes of the present invention are further described and compared with related compositions and process by the following examples. These examplesare not tobe taken'as being limitative of the present invention. In each case, percentages are by weight unless otherwise indicated.
- EXAMPLE 1 EXAMPLE 2 Four pad baths were prepared. Pad Baths A and B contained the product of Example 1, and pad baths C and D contained a 60/40 molar mixture of tetrakis(hydroxymethyl )phosphonium acetate/tetrakis(hydroxy- I treatment.
- each pad bath also contained urea and 0.56% by weight of a surfactant.
- the padbaths were applied to cotton flannelette and the treated fabrics were dried-at 225F. for 3.0miriutesand then heated at 350F. for 3.0 minutes. After curing all fabrics were washed in a solution con-- taining 5% real hydrogen peroxide based on the dry weight of the treated fabric using sufficient sodium silicate to maintain apI-I in the range of-9.0 to 9.5 duringthe washing cycle.
- the compositions of the pad baths and treated fabrics are shown in Table II.
- the TKS-treated fabrics had a softer hand then those treated with TKP.
- the hand of the TKS-treated fabric at the 3.58% phosphorus level (pad bath E) was as soft as the TKP-treated fabric at the 3.04% phosphorus level (pad bath B).
- the durability of the TKS treatment is about the same as that of the TKP treatment at any level of addon under the same washing conditions.
- EXAMPLE 4 A pad bath was prepared containing the product of Example 1 at 32.5% TKS on the weight of the pad bath, the pad bath had a pH of 4.2. The pad bath was applied to 5.5oz/-yd bleached, mercerized cotton at 100% expression, and the treated fabric was dried 4 minutes at 225F. and heated 4 minutes at 325F. to obtain a phos phorus content of 3.5% onthe weight of the fabric. The treated fabric, before process washing, burned completely when subjected to the Dept. of Commerce Test PFF-3-7O using a 3 second flame.
- An aqueous flame retardant finish composition solution for cellulosic textile materials comprising:
- a finish composition according to claim 2 comprising 0.3 to 1.0 mole of tetrakis(hydroxymethyl)- phosphonium oxalate and from 0.5 to 2 moles of urea per liter of solution.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US317998A US3888779A (en) | 1972-12-26 | 1972-12-26 | Flame retardant composition containing tetrakis (hydroxymethyl) phosphonium oxalate |
| CA186,460A CA1013507A (en) | 1972-12-26 | 1973-11-22 | Flame retardant composition and process for textiles |
| AU63635/73A AU491655B2 (en) | 1972-12-26 | 1973-12-14 | Flame retardant composition and process for textiles |
| GB5862873A GB1402670A (en) | 1972-12-26 | 1973-12-18 | Flame retardant process for textiles and composition useful therein |
| FR7345934A FR2211558B1 (ru) | 1972-12-26 | 1973-12-21 | |
| IT54520/73A IT1000762B (it) | 1972-12-26 | 1973-12-21 | Procedimento per la produzione di materiali tessili cellulosici non auto combustibili prodotto ottenu to e composizione di finitura non auto combustibile impiegata |
| BE139243A BE809057A (fr) | 1972-12-26 | 1973-12-21 | Composition ignifuge et procede de son application aux textiles |
| DE2364589A DE2364589A1 (de) | 1972-12-26 | 1973-12-24 | Flammhemmende zubereitung und verfahren zur flammhemmenden ausruestung von textilien |
| JP48144195A JPS4987898A (ru) | 1972-12-26 | 1973-12-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US317998A US3888779A (en) | 1972-12-26 | 1972-12-26 | Flame retardant composition containing tetrakis (hydroxymethyl) phosphonium oxalate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3888779A true US3888779A (en) | 1975-06-10 |
Family
ID=23236190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US317998A Expired - Lifetime US3888779A (en) | 1972-12-26 | 1972-12-26 | Flame retardant composition containing tetrakis (hydroxymethyl) phosphonium oxalate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3888779A (ru) |
| JP (1) | JPS4987898A (ru) |
| BE (1) | BE809057A (ru) |
| CA (1) | CA1013507A (ru) |
| DE (1) | DE2364589A1 (ru) |
| FR (1) | FR2211558B1 (ru) |
| GB (1) | GB1402670A (ru) |
| IT (1) | IT1000762B (ru) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046701A (en) * | 1976-02-23 | 1977-09-06 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
| US4088592A (en) * | 1976-02-23 | 1978-05-09 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
| US4092251A (en) * | 1976-02-23 | 1978-05-30 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
| US4104172A (en) * | 1976-02-23 | 1978-08-01 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
| US20050054553A1 (en) * | 2003-06-27 | 2005-03-10 | The Procter & Gamble Company | Liquid fabric softening compositions comprising flame retardant |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4748705A (en) * | 1986-06-05 | 1988-06-07 | Burlington Industries, Inc. | Flame resistant polyester/cotton fabric and process for its production |
| GB9008421D0 (en) * | 1990-04-12 | 1990-06-13 | Albright & Wilson | Fabric treatment process |
| GB9008420D0 (en) * | 1990-04-12 | 1990-06-13 | Albright & Wilson | Fabric treatment |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3619113A (en) * | 1969-09-26 | 1971-11-09 | American Cyanamid Co | Flame-retardant finish for cellulosic textile materials |
| US3698854A (en) * | 1970-06-24 | 1972-10-17 | Us Agriculture | Process for producing flame resistant organic textiles |
| US3799738A (en) * | 1972-02-17 | 1974-03-26 | Hooker Chemical Corp | Flame retardant process for cellulosics |
-
1972
- 1972-12-26 US US317998A patent/US3888779A/en not_active Expired - Lifetime
-
1973
- 1973-11-22 CA CA186,460A patent/CA1013507A/en not_active Expired
- 1973-12-18 GB GB5862873A patent/GB1402670A/en not_active Expired
- 1973-12-21 IT IT54520/73A patent/IT1000762B/it active
- 1973-12-21 FR FR7345934A patent/FR2211558B1/fr not_active Expired
- 1973-12-21 BE BE139243A patent/BE809057A/xx unknown
- 1973-12-24 DE DE2364589A patent/DE2364589A1/de active Pending
- 1973-12-26 JP JP48144195A patent/JPS4987898A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3619113A (en) * | 1969-09-26 | 1971-11-09 | American Cyanamid Co | Flame-retardant finish for cellulosic textile materials |
| US3698854A (en) * | 1970-06-24 | 1972-10-17 | Us Agriculture | Process for producing flame resistant organic textiles |
| US3799738A (en) * | 1972-02-17 | 1974-03-26 | Hooker Chemical Corp | Flame retardant process for cellulosics |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046701A (en) * | 1976-02-23 | 1977-09-06 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
| US4088592A (en) * | 1976-02-23 | 1978-05-09 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
| US4092251A (en) * | 1976-02-23 | 1978-05-30 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
| US4104172A (en) * | 1976-02-23 | 1978-08-01 | Velsicol Chemical Corporation | Durable flame retardant finishes for textile materials |
| US20050054553A1 (en) * | 2003-06-27 | 2005-03-10 | The Procter & Gamble Company | Liquid fabric softening compositions comprising flame retardant |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1013507A (en) | 1977-07-12 |
| GB1402670A (en) | 1975-08-13 |
| JPS4987898A (ru) | 1974-08-22 |
| FR2211558B1 (ru) | 1977-09-09 |
| BE809057A (fr) | 1974-06-21 |
| FR2211558A1 (ru) | 1974-07-19 |
| AU6363573A (en) | 1975-06-19 |
| DE2364589A1 (de) | 1974-06-27 |
| IT1000762B (it) | 1976-04-10 |
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