US3715185A - Compositions for flame-proofing cellulosic materials - Google Patents
Compositions for flame-proofing cellulosic materials Download PDFInfo
- Publication number
- US3715185A US3715185A US3715185DA US3715185A US 3715185 A US3715185 A US 3715185A US 3715185D A US3715185D A US 3715185DA US 3715185 A US3715185 A US 3715185A
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- United States
- Prior art keywords
- flame
- textile
- fabric
- treated
- weight
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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
- 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
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
-
- 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
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/24—Flameproof
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/12—Wave energy treatment of textiles
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/18—Grafting textile fibers
-
- 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
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
- Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics
-
- 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
- This invention relates to a wash-durable single step aqueous bath treatment for cellulosic textiles which renders them tire and wrinkle resistant.
- the textile materials are impregnated usually with aqueous solutions containing the organic phosphorous compounds, dried and then subjected to conditions which insolubilize the flame retardant in situ. While such an impregnation materially improves the properties of the heavier fabrics, it is often diflicult to obtain the desired degree of flame resistance in the lighter weight fabrics without adversely altering other properties of the fabric. For example, it is often diflicult to impart fire resistance to fabrics of less than about 7 ounces per yard without causing an undesirable increase in the stiifness of the fabric. It is also difiicult to impart to any fabric an appreciable increase in both wrinkle resistance and flame resistance. In order to obtain both flame resistance and wrinkle resistance, the textile material was usually treated successively with a flame retardant and then with a compound capable of imparting wrinkle resistant properties. A single treatment process to impart both flame retardancy and wrinkle resistance has been long sought after in the art.
- An object of the present invention is to provide an improved method for treating textile fabrics so as to improve their flame resistance to a greater degree than prior art flame retardancy methods at equal add on" levels.
- a second object is to simultaneously impart wrinkle resistant and flame resistant properties to cellulosic textiles without materially increasing the fabric stiffness.
- Another object is to provide textile treating composition comprising a compound containing both phosphorus and nitrogen by which both the wrinkle resistance and the flame resistance of a textile can be enhanced by a single treatment.
- An additional object is to provide treated cellulosic textile materials which are both flame and wrinkle resistant at low add on levels.
- the present invention comprises treating a textile material with a solution containing N,N',N"-triallylphosphoric triamide, drying to remove excess solvent, and then either curing at elevated temperatures in the presence of a catalyst or irradiating in with a radio active source material to produce a wrinkle resistant and flame resistant textile fabric.
- Textile materials which may be modified include those derived from cellulosic materials such as cotton, linen, rayon, jute, ramie, paper and the like. Blends of these with synthetic fabrics are also very suitable.
- the N,N,N"- triallylphosphoric triamide is prepared by reacting phosphorous oxychloride with allylamine in a non-aqueous solvent in the presence of a tertiary amine to react with the liberated hydrochloric acid.
- the preferred mole ratio of both the allylamine and the tertiary amine to phosphorous oxychlorlde is 3 to 1. Higher ratios can be used although no advantage has been found to be gained.
- Suitable solvents include the ether type such as diethyl ether or dioxane and the hydrocarbon type such as hexane, benzene, toluene, etc.
- the tertiary amine functions as an HCl acceptor and can be any trialkyl, alkyl-aryl, or heterocyclic type. Examples of trialkyl amines are triethyl amine, tripropyl amine, and tributyl amine. Examples of alkyl-aryl type are diethylphenyl amine. Examples of heterocyclic type are pyridine and pyrrole.
- the reaction between the phosphorous oxychloride and allyl-amine is exothermic and generally it has been found to be desirable to control the reaction temperature below 50 C., and preferably between 5-25 C.
- the temperature control of the reaction may be conveniently carried out by utilizing a relatively slow addition rate for the reactants or by cooling the reaction mixture.
- the HCl which is liberated during reaction reacts with the tertiary amine to form the HCl salt which precipitates during reaction and is easily removed from the reaction by filtration.
- the desired N,N',N-triallylp'hosphoric triamide is recovered by removal of the solvent and excess reactants by any suitable means such as vacuum distillation.
- the N,N, "-triallylphosphoric triamide can be formulated into the desired treating composition.
- Any suitable formulation can be used, for example, an emulsion or solution, with aqueous solution being generally preferred.
- the treating solution can be applied to the fabric by dipping, spraying, rolling, padding or the like techniques, as are known to those skilled in the art.
- the excess of the formulation can be removed by squeezing, centrifuging, pressing, or other similar operations.
- the material can, if desired, be dried and is then cured by holding the treated textile material for several minutes at high temperatures or for several hours at lower temperatures, or in the presence of a radioactive source for several minutes.
- the N,N','N"-triallylphosphoric triamide is included in the erably at temperatures within the range of about 150 to 180 C. At these temperatures, curing times of from 15 to 30 minutes are typical.
- An alternative embodiment is irradiating the cellulosic textile material which has been formulation in amounts within the range of 1 to 50 per- 5 contacted with a solution or emulsion of N,N',N"tricent by weight of the composition and preferably in allylphosphoric triamide with a radioactive material such amounts within the range of to 20 percent by weight as cobalt.
- the free radical catalyst is of the total composition. Additionally, it has been found unnecessary since the radiation acts as the polymerizato be desirable to also include in the treating composition agent.
- Such i p g of Wrinkle resistance therebycatalyst is desirably contained in the composition in The following examples illustrate several embodiments amounts within the range of about 0.1 to about perof the invention, but are not to be considered limiting. cent by weight of the formulation and preferably in amounts within the range of about 0.5 to 10 percent by EXAMPLE I weight f the heating composition 171 grams (3.0 moles) of allyl amine, 309 grams 3.05 Suitable compounds which can be used as the catalyst 20 moles) of triothylamino, and 1600 of other were include hydrogen peroxide; persulfates h as ammoplaced in a Pyrex glass reaction vessel.
- the vessel was Ilium, sodium Potassium; hydroperoxides Such as flushed with nitrogen and the contents cooled to about butyl hydroperoxide, cumene hydroperoxide; diacylper- Tooroaftor 153-4 grams mole) of Phosphorous oxides such as henzoyl pcroxide, acetyi peroxide; di aikyi oxychloride were added dropwise over a two hour period.
- hydroperoxides Such as flushed with nitrogen and the contents cooled to about butyl hydroperoxide, cumene hydroperoxide
- diacylper- Tooroaftor 153-4 grams mole Phosphorous oxides such as henzoyl pcroxide, acetyi peroxide; di aikyi oxychloride were added dropwise over a two hour period.
- peroxides such as dhhhutyi peroxide and dicumyi peroih
- the temperature of the reaction mixture was not allowed ide; peresters such as t-butyl peroxyacetate, t-butyl perto go above Afior the addition of tho Phosphorous oxybenzoate; and peracids such as performic or hermetic oxychlonde the reaction mixture was stirred at ambient
- the remainder f the textile treating compositioh is temperature for 2 hours and then filtered to remove the comprised of solvent and wetting agent, the latter being P1' oo1Pit"1tocl triothylamino'Hcl Salt- Tho filtrate was optional.
- Suitable solvents include water, hexane, bensurfed about 16 hours at ambient temperature with zene ethyl alcohol methyl alcohol, and any others Which 20 grams of decolorizing charcoal and then filtered to do not react with the N,N',N' triaiiyiphosphoric remove the latter.
- the filtrate was then vacuum distilled i Wetting agents such as Triton X400 which is to remove the ether solvent and excess reactants as overan ethylene oxide aikyi Phenol adduct can he incorho head and the desired product, N,N',N-triallylphosphoric rated in the treating composition in amounts ranging up mamido Q grams), was recovered as distillation io 5 weight Pei-chm, preferably 05 to 1 Weight percehh toms.
- Triton X400 which is to remove the ether solvent and excess reactants as overan ethylene oxide aikyi Phenol adduct can he incorho head and the desired product, N,N',N-triallylphosphoric rated in the treating composition in amounts ranging up mamido Q grams
- the Isolated product was found to be greater than
- the textile treating formulations are applied so as to 95 Percent Pure by elemental and NMR analysesprovide in the textile material an add-on desirably within EXAMPLE II the range of about 1 to 20 percent by weight of the textile material and preferably within the range of about 5 40
- a texfllentreiiltmg bath was.mad.e y combmmg 20 Parts to 15 percent by weight after the treated fabric has been of tnallylphosphonc mamlde Prepared in cured
- the term refers to the flame retardant ample I a d two parts of tertiary butyl hydroperoxide as Which has reacted with the textile material; that is, the a free radical catalyshwith sufficient water to make atotal modifying agent which remains as an integral chemical of 00 parts treatmg Solution Swatches of bleached Part of the material after curing and washing to remove desized, mercerrzed cotton print cloth weighing 4 ounces any ume
- the amount of adchon is given in per yard were then padded through this solution and a wet percent by weight based on the original dry weight of the i' on the fabnc of 100 Percent was obtained After textile materialdry1ng, the treated fabrics were then cured for 15 minutes The curing of the treated textile material is carried at 165 and then Washed under hot water to remove unreacted compound. out in one embodiment by holdmg the material at tem- S peratures between about room temperature, i.e., about i at treats were made In whlch he textlle ireatmg 25 C., and about 250 C.
- the curing is carried out at temperaare standard tests used by th: t tit t i o inc lust r I l t tures within the range of about to 250 C, and prefare given in Table 1.
- y. e resu 8 TABLE 1 Cure conditions
- Weight Vertical Wrinkl Temp. dpyerggiiti telsghchhr recoverly Treating solution l Time C.) on i h z' w l fi? giigggeilghtton--. l Bel 190 A 6.0 165 6.5 165 7.6 165 8.3 165 8.3 165 8.5 165 9.1 ii? iii Not heat treated 16 hours..- 125 12. 3
- the add-ons obtained by the nonheat treated solution ranged from 6 to 7.5 percent by weight of the untreated fabric.
- the fabrics containing 6.5 and 7.5 weight percent add-ons passed the vertical flame test as the char lengths obtained were 4.5 inches. A char length of 5.5 inches is allowable by the test for cotton of this weight. Untreated cotton is consumed in the vertical flame test. Slightly higher add-ons were obtained in the range of 8.5 to 10.5 weight percent when the treating solution was heat treated prior to impregnation of the fabrics. All of the treated fabric in this add-on range passed the vertical flame test.
- Example III The procedure of Example II was repeated with the exception that longer curing times were used. In one case the treated fabric was cured for 1 hour at 165 C. and this resulted in an add-on of 14.2 weight percent (Table 1). The treated fabric passed the vertical flame test and had a wrinkle recovery angle of 271 Curing at longer times (18 hours) at lower temperatures (125) resulted in an add-on of 12.3 weight percent. The treated fabric passed the vertical flame test and had a wrinkle recovery value of 276.
- a textile treating bath was made by combining 20 parts of N,N',N-triallylphosphoric triamide prepared in Example I With sufficient water to make a total of 100 parts of treating solution. Swatches of untreated cotton fabric used in Example II were padded through this solution and a wet pick-up on the fabric of 100% was obtained. After drying the fabrics were then cured at room temperature by being exposed to a cobalt 60 radiation source with an effective exposure dose rate of 250,000 roentgens per hour. After irradiation the fabrics were washed under hot water to remove unreacted N,N',N"-triallylphosphoric triamide.
- Textile fabrics treated to impart flame resistant prop erties normally require high add-ons (15 percent or higher) which usually increase the stiffness of the fabric with no improvement in the wrinkle resistant properties of the fabric.
- Tesoro et al., supra, at p. 182 required a 17.1% add-on of NMPA to achieve a degree of fire retardancy (6.8 inch char length) which does not even pass the AATCC vertical flame test which only allows 5.5 inches of char length for 4 ounces per yard fabric.
- Our flame retardant passed this test with only 6.5 weight percent add-on (Table 1) and so appears to be mankedly superior than NMPA in flame retardancy.
- a two step process consisting of treatment of the fabric with a flame retardant and then with a compound capable of imparting wrinlkle resistance is usually required when a fabric containing both properties is desired.
- a textile fabric is treated with one compound in a single step to produce a treated fabric having improved wrinkle resistant and fire resistant properties with no increase in stiffness of the fabric.
- the addon required to impart these properties is also exceptionally low.
- a textile treating composition comprising from 1 to 50 weight percent N,N',N"-triallylphosphoric triamide, 0.1 to 20 weight percent free radical catalyst, 0 to 5 weight percent wetting agent, and the remainder solvent.
- the textile treating composition of claim 1 wherein the solvent is selected from the group consistng of water, hexane, benzene, ethyl alcohol and methyl alcohol.
- composition comprises from 10 to 20 weight percent N,N',N"-trially1phosphoric triamide, 0.5 to 10 weight percent free radical catalyst, 0.5 to 1 Weight percent wetting agent, and 89 to 69 weight percent water.
- composition of claim 1 wherein the free radical catalyst is t-butyl hydroperoxide.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Description
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8581570A | 1970-10-30 | 1970-10-30 | |
US21445771A | 1971-12-30 | 1971-12-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3715185A true US3715185A (en) | 1973-02-06 |
Family
ID=26773120
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US3666402D Expired - Lifetime US3666402A (en) | 1970-10-30 | 1970-10-30 | Compositions and method for flame-proofing cellulosic materials while simultaneously imparting wrinkle resistance,and articles thereby produced |
US3715185D Expired - Lifetime US3715185A (en) | 1970-10-30 | 1971-12-30 | Compositions for flame-proofing cellulosic materials |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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US3666402D Expired - Lifetime US3666402A (en) | 1970-10-30 | 1970-10-30 | Compositions and method for flame-proofing cellulosic materials while simultaneously imparting wrinkle resistance,and articles thereby produced |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3932123A (en) * | 1973-03-16 | 1976-01-13 | The United States Of America As Represented By The Secretary Of Agriculture | Flameproofing of cotton cellulose with hexamethyl phosphorous triamide |
US3936267A (en) * | 1975-02-27 | 1976-02-03 | The United States Of America As Represented By The Secretary Of Agriculture | Flameproofing wool textiles |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3906136A (en) * | 1971-04-30 | 1975-09-16 | Stauffer Chemical Co | Process of flame retarding substrates by applying hexahydratriazine phosphonate derivatives |
SE7407376L (en) * | 1973-06-22 | 1974-12-23 | Ciba Geigy Ag | |
SE7407374L (en) * | 1973-06-22 | 1974-12-23 | Ciba Geigy Ag | |
AR205092A1 (en) * | 1973-06-22 | 1976-04-05 | Ciba Geigy Ag | PROCEDURE FOR IGNIFUGATION BY THE ORGANIC FIBER MATERIAL TRANSFER METHOD |
SE7407377L (en) * | 1973-06-22 | 1974-12-23 | Ciba Geigy Ag |
-
1970
- 1970-10-30 US US3666402D patent/US3666402A/en not_active Expired - Lifetime
-
1971
- 1971-12-30 US US3715185D patent/US3715185A/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3932123A (en) * | 1973-03-16 | 1976-01-13 | The United States Of America As Represented By The Secretary Of Agriculture | Flameproofing of cotton cellulose with hexamethyl phosphorous triamide |
US3936267A (en) * | 1975-02-27 | 1976-02-03 | The United States Of America As Represented By The Secretary Of Agriculture | Flameproofing wool textiles |
Also Published As
Publication number | Publication date |
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US3666402A (en) | 1972-05-30 |
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