US3068060A - Treatment of cellulose textiles with phosphoramides - Google Patents
Treatment of cellulose textiles with phosphoramides Download PDFInfo
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- US3068060A US3068060A US83106559A US3068060A US 3068060 A US3068060 A US 3068060A US 83106559 A US83106559 A US 83106559A US 3068060 A US3068060 A US 3068060A
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- fabric
- cellulose
- phosphorodiamidate
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- drying
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- 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
- 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
- Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
-
- 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
Definitions
- the compounds with which the cellulosic fabrics are treated in accordance with the present invention are phosphoroamides having the formula wherein X is selected from the group consisting of OR, -NHR and in which R is a C -C alkyl group, and R and R are the same or different C -C alkyl groups.
- Preferred compounds are those in which R, R, and/or R is or are methyl groups.
- the treated cellulosic fabrics exhibit outstanding durability to washing and dry-cleaning and retain their improvement in crease-resistance and shrinkage-reduction even after washing in the usual detergents which are commonly alkaline in character.
- the treated cellulosic products are also resistant to ordinary acid souring applied in laundries after the washing and rinsing stages.
- the cellulosic products obtained by treatment with the new compounds are also insoluble because of their cross-linked character so that the improvements in shrinkage and crease-resistance are obtained even after dry-cleaning operations.
- the treated fabrics also retain excellent hand and feel.
- the treatment of the cellulosic fabrics with the phosmetal being in a state where its valence is from 3 to 7, Y is fluorine or oxygen, and b is an integer having a value of 4 or 6.
- the metals of these salts are those of groups Ib, II, IIIb, IV, and VIII of the periodic table in T. Moeller, Inorganic Chemistry, John Wiley & Sons, New York, 1952, which have an atomic weight of at least 12. Salts of perchloric and fiuoboric acids are very efficient catalysts, particularly their zinc, lead, copper, and magnesium compounds.
- Salts of sulfuric acid such as aluminum and copper sulfate, and of fluosilicic acid, such as magnesium, zinc, and copper fluosilicates, also are active as catalysts.
- Other acidic compounds such as acetic acid, phosphoric acid, and sodium bisulfate, may also be used as catalysts.
- catalysts which are especially useful are ammonium phosphate, ammonium thiocyanate, and mixtures of 1 mole of formaldehyde with 1 mole of the hydrochloric or other acid salts of a hydroxy aliphatic amine including Z-methyl-Z-amino-l-propanol, Z-methyl- 2-amino-L3-nronandiol, tris(hydroxv)aminomethane, 2- phenyl-Z-amino-l-pronanol, 2-methyl-2-amino-l-pentanol, -2-aminobutanol, triethanolamine, 2-amino-2-ethyl-1-butano], also ammonium chloride.
- amine salts are watersoluble latent catalysts substantially neutral at ordinary temperature but dissociate into volatile components one of which is acidic at the elevated temperatures used for baking and curing, so that the catalyst after exerting its accelerating effect is automatically discharged during the heating or curing stage.
- the amount of catalvst may vary from about 0.2% to 5% and is preferably in the range of 0.5% to 1% concentration in the aqueous solution of l the phosphoroamide.
- phoroamides in accordance with the present invention may be effected most advantageously by means of aqueous solutions, dispersions, or emulsions in which the phosphoroamide is dissolved, dispersed or emulsified at a concentration which may vary from 1 to 30% by weight.
- concentration is from 5 to 15% to ob tain the maximum benefits in crease-proofing and shrinkage reduction.
- the treatment may be carried out in the presence of a catalyst.
- a catalyst there may be used metal salts of acids having the composition H (XY where H is hydrogen, a is an integer which depends on the valence of the complex ion and may have a value of 1 to 3, 'X-is a non-metal selected from the group consisting of boron, silicon, sulfur, and chlorine, -said nonp
- the catalyzed solution, dispersion, or emulsion of the 'phosphoroamide is compatible with solutions or dispersions of most of the common textile finishing agents, such as synthetic polymer latices and aminoplast resins or precondensates, so that they may be applied with the phosphoroamide to produce changes in the hand or other properties of the fabric.
- the aqueous solution, dispersion, or emulsion containing the phosphoroamide and catalyst may be applied to the fabric in any suitable manner such as by spraying or impregnation.
- the impregnation may be carried out in open width, and the fabric may be handled in any form.
- the impregnation may be carried out in a tumble Wheel, laundry machine, or other suitable equipment.
- the impregnated fabric immediately after impregnation and without preliminary low-temperature drying is carried in open width by a tenter frame through a curing oven where it is subjected to temperatures of about 212 F. to about 450 F.
- a flash cure at 700 to 750 F. for 1 to 20 seconds may be used. Entirely satisfactory results are obtained by heatingfor tenminutes at about 300 F. This curing operation not only dries the impregnated fabric but apparently causes a reaction between ;he phosphoroamide and the hydroxyl groups of the celluose.
- Example 2 (a) A similar piece of cotton printcloth was saturated with an aqueous solution containing 10% of methyl phosphorodiamidate and 1.5% of zinc perchlorate. It was dried for five minutes at 220 F. and then heated for five minutes at 340 F. to complete the insolubilization and cross-linking of the cellulosic material in the fabric. After conditioning, the sample had a crease-recovery angle of 120. The fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
- the recovery angle was 102.
- the fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
- Example 4 An 80 x 80 cotton printcloth was saturated with an aqueous solution containing 10% of isobutyl phosphorodiamidate and 1% of acetic acid. After drying, heating, and conditioning as in Example 1, the fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
- a process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of a phosphoroamide of the formula wherein X is a member selected from the group consisting of -NHR and in which R is a C -C alkyl group, and R is a C -C alkyl group, drying, and heating the impergnated fabric at a temperature of at least about 212 F.
- a process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of N,N-dimethyl phosphotriamide, drying, and heating the impregnated fabric at a temperature of at least about 212 F.
- a process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of cellulose-cross-linking material consisting of methyl phosphorodiamidate, drying, and heating the impregnated fabric at a temperature of at least about 212 F.
- a process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of cellulosecross-linking material consisting of ethyl phosphorodiamidate, drying, and heating the impregnated fabric at a temperature of at least about 212 F.
- a process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of cellulose-cross-linking material consisting of isobutyl phosphorodiamidate, drying, and heating the impregnated fabric at a temperature of at least about 212 F.
- a fabric comprising cellulose fibers modified by reaction with a phosphoroamide of the formula wherein X is a member selected from the group consisting of NHR and in which R is a C -C alkyl group, and R is a C -C alkyl group, the modification being effected by the process of claim 1.
- a fabric comprising cellulose fibers modified by reaction with N,N-dimethyl phozphotriamide by the process of claim 2.
- a fabric comprising cellulose fibers modified by reaction with ethyl phosphcrodiamidate by the process of claim 4.
- a fabric comprising cellulose fibers modified by reaction with isobutyl phosphorodiamidate by the process of claim 5.
- a process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of cellulose-cross linking material consisting of at least one (C C )-alkyl phosphorodiamidate, drying, and heating the impregnated heating the impregnated fabric at a temperature of at least about 121 F.
- a fabric comprising cellulose fibers modified by reaction with cellulose-crosslinking material consisting of at least one (C -C alkyl phosphorodiamidate by the process of claim 11.
Description
United States atent fitice 3,068,060 Patented Dec. 11, 1962 The present invention concerns crease-proofing cellulosic fabrics by the application thereto of compounds of the class of polyamides of phosphoric acid.
The compounds with which the cellulosic fabrics are treated in accordance with the present invention are phosphoroamides having the formula wherein X is selected from the group consisting of OR, -NHR and in which R is a C -C alkyl group, and R and R are the same or different C -C alkyl groups. Preferred compounds are those in which R, R, and/or R is or are methyl groups.
Examples of these compounds include:
Methyl phosphorodiamidate, Ethyl phosphorodiamidate, n-Propyl phosphorodiamidate, Isopropyl phosphorodiamidate, ri-Butyl 'pho sphorodiamidate, Isobutyl phosphorodiamidate, N-metayl phosphotriamide, N,N-dimethyl phosphotriamide,
, N,N-diethyl phosphotriamide, and
N,N-dibutyl phosphotriamide.
In the utilization of the compounds of Formula I for the modification of cellulosic fabrics for crease-proofing, crush-proofing, reduction of shrinkage and stabilization against dimensional changes on washing, the treated cellulosic fabrics exhibit outstanding durability to washing and dry-cleaning and retain their improvement in crease-resistance and shrinkage-reduction even after washing in the usual detergents which are commonly alkaline in character. The treated cellulosic products are also resistant to ordinary acid souring applied in laundries after the washing and rinsing stages. The cellulosic products obtained by treatment with the new compounds are also insoluble because of their cross-linked character so that the improvements in shrinkage and crease-resistance are obtained even after dry-cleaning operations. The treated fabrics also retain excellent hand and feel.
The treatment of the cellulosic fabrics with the phosmetal being in a state where its valence is from 3 to 7, Y is fluorine or oxygen, and b is an integer having a value of 4 or 6. The metals of these salts are those of groups Ib, II, IIIb, IV, and VIII of the periodic table in T. Moeller, Inorganic Chemistry, John Wiley & Sons, New York, 1952, which have an atomic weight of at least 12. Salts of perchloric and fiuoboric acids are very efficient catalysts, particularly their zinc, lead, copper, and magnesium compounds. Salts of sulfuric acid, such as aluminum and copper sulfate, and of fluosilicic acid, such as magnesium, zinc, and copper fluosilicates, also are active as catalysts. Other acidic compounds, such as acetic acid, phosphoric acid, and sodium bisulfate, may also be used as catalysts. Other catalysts which are especially useful are ammonium phosphate, ammonium thiocyanate, and mixtures of 1 mole of formaldehyde with 1 mole of the hydrochloric or other acid salts of a hydroxy aliphatic amine including Z-methyl-Z-amino-l-propanol, Z-methyl- 2-amino-L3-nronandiol, tris(hydroxv)aminomethane, 2- phenyl-Z-amino-l-pronanol, 2-methyl-2-amino-l-pentanol, -2-aminobutanol, triethanolamine, 2-amino-2-ethyl-1-butano], also ammonium chloride. pyridine h drochloride, benzvldimethylamine oxalate. The amine salts are watersoluble latent catalysts substantially neutral at ordinary temperature but dissociate into volatile components one of which is acidic at the elevated temperatures used for baking and curing, so that the catalyst after exerting its accelerating effect is automatically discharged during the heating or curing stage.
Conveniently, the amount of catalvst may vary from about 0.2% to 5% and is preferably in the range of 0.5% to 1% concentration in the aqueous solution of l the phosphoroamide.
phoroamides in accordance with the present invention may be effected most advantageously by means of aqueous solutions, dispersions, or emulsions in which the phosphoroamide is dissolved, dispersed or emulsified at a concentration which may vary from 1 to 30% by weight. Preferably, the concentration is from 5 to 15% to ob tain the maximum benefits in crease-proofing and shrinkage reduction. The treatment may be carried out in the presence of a catalyst. As a catalyst there may be used metal salts of acids having the composition H (XY where H is hydrogen, a is an integer which depends on the valence of the complex ion and may have a value of 1 to 3, 'X-is a non-metal selected from the group consisting of boron, silicon, sulfur, and chlorine, -said nonp The catalyzed solution, dispersion, or emulsion of the 'phosphoroamide is compatible with solutions or dispersions of most of the common textile finishing agents, such as synthetic polymer latices and aminoplast resins or precondensates, so that they may be applied with the phosphoroamide to produce changes in the hand or other properties of the fabric.
The aqueous solution, dispersion, or emulsion containing the phosphoroamide and catalyst may be applied to the fabric in any suitable manner such as by spraying or impregnation. In general, it is preferable to use some method of impregnation. With piece goods, this is conveniently carried out with the various machines used for treating fabrics in open width, such as pads or jigs. However, it is not required that the impregnation be carried out in open width, and the fabric may be handled in any form. In treating garments or other articles made from cellulosic fabrics, the impregnation may be carried out in a tumble Wheel, laundry machine, or other suitable equipment. After application of the solution, dispersion, or emulsion, it is desirable to remove any excess by squeezing the fabric between rollers, or by shaking or centrifuging it, in order to insure a more even treatment. The treated fabric may then be dried, such as by air-drying at normal room temperature or by heating in a drying oven at temperatures of F. and up. The drying and curing operations are preferably done with the fabric open and flat, so that it will have a smooth and even appearance when finished. In a preferred embodiment, the impregnated fabric, immediately after impregnation and without preliminary low-temperature drying is carried in open width by a tenter frame through a curing oven where it is subjected to temperatures of about 212 F. to about 450 F. or higher for a period of time ranging from about one minute to about one-half hour or more, the shorter period being employed at the higher tempera ture and vice versa. A flash cure at 700 to 750 F. for 1 to 20 seconds may be used. Entirely satisfactory results are obtained by heatingfor tenminutes at about 300 F. This curing operation not only dries the impregnated fabric but apparently causes a reaction between ;he phosphoroamide and the hydroxyl groups of the celluose.
The following examples illustrate the present invention, the parts and percentages therein being by weight unless otherwise noted. The crease-recovery values given below are those determined by the Shirley Institute Procedure (British Standard Notebook No. 11, 1949 Edition, page 128) and are the average of warp and filling values Example 1 (a) A piece of 80 x 80 cotton printcloth was saturated with an aqueous solution containing of N,N-dimethyl phosphotriamide and 1.0% of a 1:1 mole ratio mixture of formaldehyde and the hydrochloride of 2-amino-2- methyl-propanol-l. It was dried for five minutes at 220 F. and then heated for five minutes at 340 to complete the insolubilization and cross-linking of the cellulosic material in the fabric. After conditioning, the sample had a crease-recovery angle of 110. The fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
(b) By carrying out the same treatment but with 1.0% of acetic acid as the catalyst and a cure at 315 F. for minutes, a crease-recovery angle of 113 was reached. The fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
Example 2 (a) A similar piece of cotton printcloth was saturated with an aqueous solution containing 10% of methyl phosphorodiamidate and 1.5% of zinc perchlorate. It was dried for five minutes at 220 F. and then heated for five minutes at 340 F. to complete the insolubilization and cross-linking of the cellulosic material in the fabric. After conditioning, the sample had a crease-recovery angle of 120. The fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
(b) The crease-resistance of rayon was improved in similar fashion when the process of part (a) was repeated replacing the cotton fabric with regenerated cellulose fabrics of spun rayon and filament rayon yarns. The fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
Example 3 acid used as the catalyst. The recovery angle was 102.
The fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
Example 4 An 80 x 80 cotton printcloth was saturated with an aqueous solution containing 10% of isobutyl phosphorodiamidate and 1% of acetic acid. After drying, heating, and conditioning as in Example 1, the fabric was resistant to wrinkling and showed no discoloration on washing and ironing.
It is to be understood that changes and variations may be made without departing from the spirit and scope of the invention as defined by the appended claims.
We claim:
1. A process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of a phosphoroamide of the formula wherein X is a member selected from the group consisting of -NHR and in which R is a C -C alkyl group, and R is a C -C alkyl group, drying, and heating the impergnated fabric at a temperature of at least about 212 F.
2. A process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of N,N-dimethyl phosphotriamide, drying, and heating the impregnated fabric at a temperature of at least about 212 F.
3. A process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of cellulose-cross-linking material consisting of methyl phosphorodiamidate, drying, and heating the impregnated fabric at a temperature of at least about 212 F.
4. A process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of cellulosecross-linking material consisting of ethyl phosphorodiamidate, drying, and heating the impregnated fabric at a temperature of at least about 212 F.
5. A process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of cellulose-cross-linking material consisting of isobutyl phosphorodiamidate, drying, and heating the impregnated fabric at a temperature of at least about 212 F.
6. As an article of manufacture, a fabric comprising cellulose fibers modified by reaction with a phosphoroamide of the formula wherein X is a member selected from the group consisting of NHR and in which R is a C -C alkyl group, and R is a C -C alkyl group, the modification being effected by the process of claim 1.
7. As an article of manufacture, a fabric comprising cellulose fibers modified by reaction with N,N-dimethyl phozphotriamide by the process of claim 2.
8. As an article of manufacture, a fabric comprising cellulose fibers modified by reaction with methyl phosphorodiamidate by the process of claim 3.
9. As an article of manufacture, a fabric comprising cellulose fibers modified by reaction with ethyl phosphcrodiamidate by the process of claim 4.
10. As an article of manufacture, a fabric comprising cellulose fibers modified by reaction with isobutyl phosphorodiamidate by the process of claim 5.
11. A process comprising impregnating a cellulose textile with an aqueous medium containing an acid catalyst and 1 to 30% by weight of cellulose-cross linking material consisting of at least one (C C )-alkyl phosphorodiamidate, drying, and heating the impregnated heating the impregnated fabric at a temperature of at least about 121 F.
12. As an article of manufacture, a fabric comprising cellulose fibers modified by reaction with cellulose-crosslinking material consisting of at least one (C -C alkyl phosphorodiamidate by the process of claim 11.
Hechenbleikner Apr. 29, 1958 Baker Oct. 18, 1960
Claims (1)
1. A PROCESS COMPRISING IMPREGNATING A CELLULOSE TEXTILE WITH AN AQUEOUS MEDIUM CONTAINING AN ACID CATALYST AND 1 TO 30% BY WEIGHT OF A PHOSPHOROAMIDE OF THE FORMULA
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US83106559 US3068060A (en) | 1959-08-03 | 1959-08-03 | Treatment of cellulose textiles with phosphoramides |
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US83106559 US3068060A (en) | 1959-08-03 | 1959-08-03 | Treatment of cellulose textiles with phosphoramides |
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US83106559 Expired - Lifetime US3068060A (en) | 1959-08-03 | 1959-08-03 | Treatment of cellulose textiles with phosphoramides |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3527564A (en) * | 1968-04-15 | 1970-09-08 | Stevens & Co Inc J P | Process for carbonizing fibrous materials |
US3632297A (en) * | 1970-03-12 | 1972-01-04 | Stevens & Co Inc J P | Process for rendering cellulose-containing fabrics durably flame-retardant by wet-curing a melamine resin and a phosphoric acid amide on the fabric |
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 |
JPH0284562A (en) * | 1988-01-29 | 1990-03-26 | Nitto Boseki Co Ltd | Processing agent for cellulosic material and method for processing |
US5108459A (en) * | 1988-01-29 | 1992-04-28 | Nitto Boseki Co., Ltd. | Finishing agent for cellulosic materials and method for treating cellulosic materials with aqueous solution of aged phosphoric acid amide for aged amidophosphazene |
US5135542A (en) * | 1989-03-29 | 1992-08-04 | Nitto Boseki Co., Ltd. | Method for finishing a cellulosic fabric: treatment with phosporus amide compound |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2832745A (en) * | 1956-08-31 | 1958-04-29 | Shea Chemical Corp | Aqueous flameproofing compositions and cellulosic materials treated therewith |
US2957018A (en) * | 1957-10-24 | 1960-10-18 | Monsanto Chemicals | Cyanoethyl esters of phosphoroamidic acids |
-
1959
- 1959-08-03 US US83106559 patent/US3068060A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2832745A (en) * | 1956-08-31 | 1958-04-29 | Shea Chemical Corp | Aqueous flameproofing compositions and cellulosic materials treated therewith |
US2957018A (en) * | 1957-10-24 | 1960-10-18 | Monsanto Chemicals | Cyanoethyl esters of phosphoroamidic acids |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3527564A (en) * | 1968-04-15 | 1970-09-08 | Stevens & Co Inc J P | Process for carbonizing fibrous materials |
US3632297A (en) * | 1970-03-12 | 1972-01-04 | Stevens & Co Inc J P | Process for rendering cellulose-containing fabrics durably flame-retardant by wet-curing a melamine resin and a phosphoric acid amide on the fabric |
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 |
JPH0284562A (en) * | 1988-01-29 | 1990-03-26 | Nitto Boseki Co Ltd | Processing agent for cellulosic material and method for processing |
JPH0372752B2 (en) * | 1988-01-29 | 1991-11-19 | Nitto Boseki Co Ltd | |
US5108459A (en) * | 1988-01-29 | 1992-04-28 | Nitto Boseki Co., Ltd. | Finishing agent for cellulosic materials and method for treating cellulosic materials with aqueous solution of aged phosphoric acid amide for aged amidophosphazene |
US5135542A (en) * | 1989-03-29 | 1992-08-04 | Nitto Boseki Co., Ltd. | Method for finishing a cellulosic fabric: treatment with phosporus amide compound |
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