US3884628A - N-Phosphonomethyl acrylamides as flame retarding agents for textiles - Google Patents

N-Phosphonomethyl acrylamides as flame retarding agents for textiles Download PDF

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Publication number
US3884628A
US3884628A US31104772A US3884628A US 3884628 A US3884628 A US 3884628A US 31104772 A US31104772 A US 31104772A US 3884628 A US3884628 A US 3884628A
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United States
Prior art keywords
compound
textile
formula
flame
fabric
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
Application number
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English (en)
Inventor
James J Duffy
Peter Golborn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Occidental Chemical Corp
Original Assignee
Hooker Chemicals and Plastics Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to AU39796/72A priority Critical patent/AU464305B2/en
Priority to GB1265772A priority patent/GB1379315A/en
Priority to BE781014A priority patent/BE781014A/fr
Priority to AT239972A priority patent/AT308764B/de
Priority to AT768672A priority patent/AT311918B/de
Priority to CH1259175A priority patent/CH583811B5/xx
Priority to CH1259175D priority patent/CH1259175A4/xx
Priority to CH444172A priority patent/CH573946A5/xx
Priority to FR7210711A priority patent/FR2132102B1/fr
Priority to NL7204125A priority patent/NL7204125A/xx
Priority to DE19722215434 priority patent/DE2215434A1/de
Application filed by Hooker Chemicals and Plastics Corp filed Critical Hooker Chemicals and Plastics Corp
Priority to US31104772 priority patent/US3884628A/en
Application granted granted Critical
Publication of US3884628A publication Critical patent/US3884628A/en
Assigned to OCCIDENTAL CHEMICAL CORPORATION reassignment OCCIDENTAL CHEMICAL CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE APRIL 1, 1982. Assignors: HOOKER CHEMICALS & PLASTICS CORP.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • 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
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • 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
    • 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

  • ABSTRACT A process for imparting flame resistance to textile materials which comprises combining a flame retardant amount of a compound of the formula II II (R0) PCH 4
  • : C( ; CH
  • R is aryl or alkyl
  • Y is -H or lower alkyl
  • Z is --I-I or C1-I with a textile selected from the group consisting of a cellulosic material, a proteinaceous material, polyethylene terephthalate and blends thereof.
  • One process which involves the use of a single processing bath consists of padding a dispersion of achlorinated hydrocarbon and finely divided antimony oxide on the cellulosic fabric. The fabric is then heated to render the finish wash-proof. Near the combustion temperature, antimony oxide will react with hydrogen chloride, generated by degradation of the chlorinated hydrocarbon, to form antimony oxychloride which suppresses flame.
  • the combination of a chlorinated hydrocarbon and finely divided antimony oxide are not acceptable finishes for closely woven fabrics because they deleteriously effect the hand of the finished product.
  • Flame resistance has been imparted to cellulosic materials by esterification of the cellulose with diammonium hydrogen orthophosphate. Products so treated are subject to metathesis reactions with cations in aqueous solution during washing, the ammonium cation being displaced by calcium, sodium or magnesium. The flame resistance properties of the diammonium orthophosphate ester of the cellulosic material is then regenerated by reacting the washed product with an ammonium chloride solution.
  • R is a univalent hydrocarbon radical independently selected from the group consisting of phenyl and lower alkyl radicals of l to 8 carbon atoms:
  • Y is selected from the group consisting of -H and lower alkyl radicals of 1 to 8 carbon atoms;
  • Z is selected from the group consisting of H and CH
  • This invention also includes methods for imparting flame resistance to textile materials by incorpo' rating into the textile a flame retardant amount of one or more of the compounds of this invention. Furthermore, the flame retardant textile composition forms a third aspect of this invention.
  • the compounds of this invention are prepared by conventional methods by the reaction of a tertiary phosphite and an N-hydroxymethyl acrylamide or N- hydroxymethyl methacrylamide and their N-alkylated analogs.
  • the latter compounds being produced by the reaction of formaldehyde with acrylamide, methacrylamide or their N-alkylated derivatives.
  • the compounds of this invention may be applied to textile materials by conventional finishing techniques such as by thermal or radiation induced pad curing.
  • the finished textile product whether subjected to additional finishing treatments or not, exhibits durable, flame resistant properties.
  • durable applicants mean the flame retardant is fast to plural laundering or dry cleaning treatments.
  • the flame retarding agents of this invention may be applied to various textiles such as cellulosic materials, proteinaceous materials, polyethylene terephthalate, and analogous man-made fibers.
  • cellulosic materials applicants intend to embrace cotton, rayon, regenerated cellulose and cellulose derivatives which retain the cellulose backbone and at least one hydroxyl substituent per repeating glucose unit.
  • proteinaceous material applicants intend to embrace those textile materials which present the functional groups of protein, such as wool.
  • the reaction of amides with formaldehyde is well known to form N-hydroxymethyl derivatives.
  • the second step of this sequence may be described as a transesterification reaction of the unsaturated alcohol with the tertiary phosphite ester and a subsequent rearbe in the order of N-hydroxymethylamide/phosphite from about 1/1 to about l/lO.
  • a mole of alcohol corresponding to the phosphite used is formed and removed during the reaction.
  • excess phosphite is removed by distillation under reduced pressure to yield the product which can be used as such without additional purification.
  • the products of this invention have advantages over the flame retardant agents of the prior art in that they may be used on a variety of textile materials ofdifferent chemical compositions and they may be applied by a variety of methods. They may be applied to materials in either the fiber or fabric form to give durable, flame resistant materials with minimum detectable physical changes in the quality of the textile material.
  • Cellulosic textile materials may be made flame retardant via a variety of methods.
  • Cellulose may be treated with aqueous NaOH solutions to produce an ionic form which will add to the flame retardants of this invention.
  • the reaction is by addition of the cellulose alkoxide to the (1,3 unsaturated carbonyl compound of this invention.
  • applicants do not wish to be bound by this theory and intend to protect the claimed invention in whatever form or by whatever mechanism it takes. For example,
  • Samples of cellulosic material are immersed in a -30 percent by weight NaOH solution for l-2O minutes and squeezed to a wet pick up of 60-80% based upon the weight of cellulosic material using a two roll laboratory padder at 60 pounds per square inch gauge pressure. The samples are then dried at 200275F. from l-5 minutes in a circulating air oven. These samples are then immersed in an aqueous solution of the flame retardant of this invention (-70% by weight) for l-2O minutes and squeezed to 6080% wet weight pick up based upon the weight of textile on a laboratory padder. The materials are then cured in a circulating air oven at 200-275F. for l1O minutes to promote reaction. The samples are then washed in hot water to remove residual unreacted material and dried.
  • the products may also be grafted to cellulose via a free radical source generated on the cellulose backbone via electron beam irradiation.
  • a free radical source generated on the cellulose backbone via electron beam irradiation.
  • Cellulose is known to form stable free radicals under the influence of this type of irradiation.
  • the materials to be grafted are immersed in a solution of the phosphorus acrylamide and squeezed in a two roll laboratory padder at 60 pounds per square inch gauge pressure to about 70% wet weight pick up. The materials are then passed under an electron beam two times to give an average dose of 1.66 megarads to induce grafting. The samples are then boiled for one half hour in water to remove any homopolymer of the acrylamide which may have formed and dried.
  • the products of this invention may also be applied to ccllulosic materials in combination with other materials to give a cross-linking insoluble polymer.
  • ccllulosic materials in combination with other materials to give a cross-linking insoluble polymer.
  • the sample of textile material is immersed in an aqueous solution of phosphorus-acrylamide, formaldehyde, trimethylolmelamine, and ZnNO .6H O and squeezed on a two roll padder to 90% wet weight pick up.
  • the material is dried at 200-270F for 1-3 minutes and cured at 300370F for l-6 minutes in a circulating air oven.
  • the samples are then washed in hot water and dried.
  • Electron beam irradiation may also be used to pro mote stable free radicals on polyester fibers made from a dibasic acid and a diol, such as polyethylene terephthalate, and wool in addition to cellulose. Fibers or fabrics of polyester and wool may be made to react with the products of this invention at a dose of 1.66 megarads and greater to produce permanantly grafted materials by the procedure described for cotton above. In addition blends of cotton and polyester may be treated in the same manner to produce uniformly treated fire retardant fiber or fabric blends.
  • Examples l-4 illustrate the production of the flame retarding agents of this invention while examples 513 illustrate the application and flame retardant effect of the application of the agents of this invention to various textile materials.
  • the process steps were performed as follows except where a specific method is otherwise indicated. Padding was done on a standard two roll laboratory padder at a gauge pressure of 60 pounds per square inch in all cases. Drying and curing during processing were done with a standard laboratory textile circulating air oven. Washing and drying were done in standard home top loading automatic washer and a tumble dryer. Flammability testing was done in accordance with (American Association of Textile Chemists and Colorists) Test Method 34-1966, the standard vertical char method.
  • the finished samples for testing have a flame retardant add on of from 5-40% by weight and preferably from 1025% by weight of substrate.
  • the material was characterized by infrared spectroscopy, and nuclear magnetic resonance spectroscopy. Molecular weight determination showed a molecular weight of 197, an unsaturation of 93% and elemental analyses of the isolated product as 36.4% C; 6.4% H; 6.9% N; and 16.3% P.
  • N-methylol methacrylamide (57 g 0.5 mole) was added over 45 minutes to triethyl phosphite (83 g 0.5 mole) held at l 10C. in a three necked round bottomed flask fitted with a distillation head with a water condenser, thermometer, addition funnel, mechanical stirrer, and heating mantle.
  • Ethyl alcohol was distilled from the reaction mixture during the addition. After the addition the mixture was held minutes at 100C. and then stripped at 70C. for one hour under vacuum on a rotary evaporator.
  • N-methyl acrylamide 1.0 mole
  • paraformaldehyde 1.0 mole
  • ethylene dichloride 250 ml.
  • N-hydroxymethyl N- methyl acrylamide 1.0 mole
  • the reaction temperature is kept in the range 95 to C. and methanol is removed by distillation as it is formed.
  • the reaction mixture is held at 100 for 10 minutes, then cooled and stripped on a rotary evaporator to give N-dimethylphosphonomethyl N-methyl acrylamide.
  • EXAMPLE 7 A sample of cotton sheeting, 5.0 ounces per square yard, was impregnated with an aqueous solution containing 15 g of NaOH per 100 g of solution and squeezed to about 80 percent wet pick up. The impregnated fabric was then dried at 250F for two minutes. The resulting fabric was then impregnated with an aqueous solution containing about 50 g of N-dimethylphosphonomethyl acrylamide per 100 g of solution and squeezed to about 80 percent wet weight pick up. This impregnated fabric was then dried for 2.0 minutes at 250F. and cured for 2.5 minutes at 330F. The material was then washed in hot water and dried. The
  • treated fabric had an initial char length of 5.0 inches and a char length of 4.1 inches after washes as measured by AATCC Method 344966.
  • EXAMPLE 8 A sample of 5.0 ounces per square yard cotton sheeting was treated with an aqueous solution of N-diethylphosphonomethyl methaerylamide of about 50 g per 100 g of solution as in Example 1. A char length of 5.7 inches was obtained initially and 5.7 after 5 washes.
  • EXAMPLE 9 A sample of 5.0 ounces per square yard cotton sheeting was treated with an aqueous solution of N- dibutylphosphonomethyl acrylamide of about 65 g per 100 g of solution as in Example 1. An initial char length of 6.3 inches was obtained which was changed to 7.9 inches after five washes.
  • EXAMPLE 10 A sample of 5.0 ounces per square yard cotton sheeting was impregnated with an aqueous solution containing N-dimethylphosphonomethyl acrylamide, 75 parts; 37% formal in solution, parts; trimethylolmelamine, 37.5 parts; ZnN0 .6H O, 20 parts; and water; 92.5 parts. The fabric was squeezed to about 65% wet pick 4 minutes. The fabric was then given a hot water wash. An initial char of 5.9 inches was obtained and a 5.6 inch char was obtained after five washes as measured by AATCC Method 34-1966.
  • EXAMPLE 11 A sample of rayon staple fiber was immersed in an aqueous solution containing 10 g of NaOH per 100 g of solution for 10 minutes and then squeezed to about 60% wet pick up and dried at 250F for 3 minutes. The sample was then immersed in an aqueous solution containing 35 g of N-dimethylphosphonomethyl acrylamide per 100 g of solution for 10 minutes and squeezed to remove excess solution. The sample was then held for 6 minutes at 330F and rinsed in hot water and dried. The fiber was then twisted tightly and held in a bunsen flame. Upon removal the material was selfextinguishing. A sample not treated by the procedure described was completely consumed by the bunsen flame.
  • EXAMPLE 12 A sample of 5.0 ounces per square yard cotton sheeting was impregnated with an aqueous solution of I up, dried for 2 minutes at 250F and cured at 350F for 8 Ndimethylphosphonomethyl acrylamide containing 40 g of the amide per 100 g of solution. The fabric was squeezed to about 70% wet pick up and irradiated at a dose of 1.66 megarads of ionizing radiation. The fabric was boiled 0.5 hours in water and then dried to give about 17% weight add on. An initial char of 4.1 inches and a char of 5.0 inches'was obtained after 50 home washes.
  • EXAMPLE 13 A sample of 4.5 ounces per square yard of polyester fabric was impregnated with an aqueous solution containing g of N-dimethylphosphonomethyl acrylamide per 100 g of solution. The fabric was squeezed to about wet pick up and irradiated at 1.66 megarads of ionizing radiation. The fabric was boiled 0.5 hours in water and dried. An initial char of 6.0 inches was obtained and after 25 washes a char length of 715 inches was obtained.
  • EXAMPLE 14 A sample of about 4.5 ounces per square yard fabric of a 65/35 blend of polyethylene terephthalate to cotton was impregnated with an aqueous solution containing 60 g of N-dimethylphosphonomethyl acrylamide per 100 g of solution. The fabric was squeezed to about wet pick up and irradiated at a dose of 1.66 megarads with ionizing radiation. The fabric was boiled 0.5 hours in water and dried. The resulting fabric showed an initial char of 4.5 inches and 6.5 inches after 15 home washes.
  • a process for imparting flame resistance to textile materials which comprises combining a flame retardant amount of a compound of the formula in which R is aryl or alkyl; Y -H or lower alkyl; and Z is H or CH;, with a textile selected from the group consisting of a cellulosic material, a proteinaceous material, polyethylene terephthalate and blends thereof.
  • the process of claim 1 wherein the compound is of the formula II I 2 2 2m2 2 2 10.
  • a composition of matter comprising a textile material selected from the group consisting of a cellulosic material, a proteinaceous material, polyethylene tere- 7.
  • the compound is phthalate and blends thereof and a flame retarding of the formula amount of a compound of the formula 0 o 0 0 n n II II CH 2 c 0 NE on P(ocu 2Q (R0) PCH t lC( Z-CH cs y Y z 8.
  • the compound is of the formula in which R is aryl or alkyl; Y IS H or lower alkyl; and

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
US31104772 1971-03-29 1972-11-30 N-Phosphonomethyl acrylamides as flame retarding agents for textiles Expired - Lifetime US3884628A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
AU39796/72A AU464305B2 (en) 1971-03-29 1972-03-08 N-phosphonomethyl acrylamides
GB1265772A GB1379315A (en) 1971-03-29 1972-03-17 N-phosphonomethyl acrylamides
AT768672A AT311918B (de) 1971-03-29 1972-03-21 Verfahren zum Flammfestmachen von Textilien
BE781014A BE781014A (fr) 1971-03-29 1972-03-21 Acrylamides n-phosphono-methyliques
AT239972A AT308764B (de) 1971-03-29 1972-03-21 Verfahren zur Herstellung von neuen N-Phosphonomethyl-acrylamiden
CH1259175D CH1259175A4 (fr) 1971-03-29 1972-03-24
CH1259175A CH583811B5 (fr) 1971-03-29 1972-03-24
CH444172A CH573946A5 (fr) 1971-03-29 1972-03-24
FR7210711A FR2132102B1 (fr) 1971-03-29 1972-03-27
NL7204125A NL7204125A (fr) 1971-03-29 1972-03-28
DE19722215434 DE2215434A1 (de) 1971-03-29 1972-03-29 N Phosphonomethyl acrylamide
US31104772 US3884628A (en) 1971-03-29 1972-11-30 N-Phosphonomethyl acrylamides as flame retarding agents for textiles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12913871A 1971-03-29 1971-03-29
US31104772 US3884628A (en) 1971-03-29 1972-11-30 N-Phosphonomethyl acrylamides as flame retarding agents for textiles

Publications (1)

Publication Number Publication Date
US3884628A true US3884628A (en) 1975-05-20

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Application Number Title Priority Date Filing Date
US31104772 Expired - Lifetime US3884628A (en) 1971-03-29 1972-11-30 N-Phosphonomethyl acrylamides as flame retarding agents for textiles

Country Status (9)

Country Link
US (1) US3884628A (fr)
AT (2) AT311918B (fr)
AU (1) AU464305B2 (fr)
BE (1) BE781014A (fr)
CH (3) CH573946A5 (fr)
DE (1) DE2215434A1 (fr)
FR (1) FR2132102B1 (fr)
GB (1) GB1379315A (fr)
NL (1) NL7204125A (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4020271A (en) * 1975-01-13 1977-04-26 Personal Products Company Crosslinked phosphonoalkyl cellulose and absorbent devices incorporating same
US4026808A (en) * 1972-03-30 1977-05-31 Hooker Chemicals & Plastics Corporation Flame retardant textile finishes
US4066597A (en) * 1974-12-20 1978-01-03 Ciba-Geigy Corporation Method of finishing synthetic organic fibrous material, in particular of providing it with an antistatic finish
US4774349A (en) * 1985-11-13 1988-09-27 Rohm Gmbh Chemische Fabrik Method of preparing N-methylphosphonic acid diesters of acrylic and methacrylic acid amines from methylol
US4794037A (en) * 1984-03-16 1988-12-27 Toray Industries Incorporated Flame-proof fiber product
US20070028805A1 (en) * 2005-07-08 2007-02-08 Liliana Craciun (Meth)acrylamide phosphorus monomer compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2217746A1 (de) * 1972-04-13 1973-10-25 Bayer Ag N-acylamino-methyl-phosphonate
DE2829046A1 (de) * 1978-07-01 1980-01-10 Benckiser Knapsack Gmbh Verfahren zur herstellung von acylamino-methanphosphonsaeuren
DE3540216C2 (de) * 1985-11-13 1994-06-16 Roehm Gmbh Verfahren zur Herstellung von N-Methylphosphonsäurediestern von Acryl- bzw. Methacrylsäureamiden aus Methylolverbindungen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3639532A (en) * 1967-04-25 1972-02-01 Bayer Ag Esters and/or amides of acids of phosphorus containing a group having the formula roch2nhco-
US3650670A (en) * 1968-03-27 1972-03-21 Stevens & Co Inc J P N-(oxymethyl) derivatives of phosphonopolyamino-s-triazines used as flame retardants for cellulosic materials
US3700403A (en) * 1967-04-11 1972-10-24 Ciba Geigy Ag Process for flameproofing cellulose-containing fibrous materials

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3700403A (en) * 1967-04-11 1972-10-24 Ciba Geigy Ag Process for flameproofing cellulose-containing fibrous materials
US3639532A (en) * 1967-04-25 1972-02-01 Bayer Ag Esters and/or amides of acids of phosphorus containing a group having the formula roch2nhco-
US3650670A (en) * 1968-03-27 1972-03-21 Stevens & Co Inc J P N-(oxymethyl) derivatives of phosphonopolyamino-s-triazines used as flame retardants for cellulosic materials

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4026808A (en) * 1972-03-30 1977-05-31 Hooker Chemicals & Plastics Corporation Flame retardant textile finishes
US4066597A (en) * 1974-12-20 1978-01-03 Ciba-Geigy Corporation Method of finishing synthetic organic fibrous material, in particular of providing it with an antistatic finish
US4020271A (en) * 1975-01-13 1977-04-26 Personal Products Company Crosslinked phosphonoalkyl cellulose and absorbent devices incorporating same
US4794037A (en) * 1984-03-16 1988-12-27 Toray Industries Incorporated Flame-proof fiber product
US4774349A (en) * 1985-11-13 1988-09-27 Rohm Gmbh Chemische Fabrik Method of preparing N-methylphosphonic acid diesters of acrylic and methacrylic acid amines from methylol
US20070028805A1 (en) * 2005-07-08 2007-02-08 Liliana Craciun (Meth)acrylamide phosphorus monomer compositions
US8105689B2 (en) 2005-07-08 2012-01-31 Basf Se Adhesive, coating or film composition applied to a surface

Also Published As

Publication number Publication date
FR2132102B1 (fr) 1977-07-22
BE781014A (fr) 1972-09-21
CH583811B5 (fr) 1977-01-14
CH573946A5 (fr) 1976-03-31
AT311918B (de) 1973-12-10
CH1259175A4 (fr) 1976-06-30
AU3979672A (en) 1973-09-13
AT308764B (de) 1973-07-25
DE2215434A1 (de) 1972-10-12
NL7204125A (fr) 1972-10-03
FR2132102A1 (fr) 1972-11-17
AU464305B2 (en) 1975-08-05
GB1379315A (en) 1975-01-02

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