US3709658A - Method for decreasing the flammability of cellulosic fabrics - Google Patents
Method for decreasing the flammability of cellulosic fabrics Download PDFInfo
- Publication number
- US3709658A US3709658A US00201213A US3709658DA US3709658A US 3709658 A US3709658 A US 3709658A US 00201213 A US00201213 A US 00201213A US 3709658D A US3709658D A US 3709658DA US 3709658 A US3709658 A US 3709658A
- Authority
- US
- United States
- Prior art keywords
- fabric
- percent
- fabrics
- flammability
- decreasing
- 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
- 239000004744 fabric Substances 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims description 14
- 230000003247 decreasing effect Effects 0.000 title description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 16
- 229920002678 cellulose Polymers 0.000 abstract description 13
- 239000001913 cellulose Substances 0.000 abstract description 13
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 abstract description 12
- 229910001379 sodium hypophosphite Inorganic materials 0.000 abstract description 12
- -1 acrylamidomethyl Chemical group 0.000 abstract description 9
- 229910052794 bromium Inorganic materials 0.000 abstract description 8
- 230000005865 ionizing radiation Effects 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 description 12
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 10
- 229920000297 Rayon Polymers 0.000 description 9
- 239000002964 rayon Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 208000021017 Weight Gain Diseases 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002759 woven fabric Substances 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
- 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
- D06M13/322—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 nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/41—Amides derived from unsaturated carboxylic acids, e.g. acrylamide
- D06M13/412—N-methylolacrylamides
-
- 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
- D06M14/20—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 on to materials of natural origin
- D06M14/22—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 on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/18—Grafting textile fibers
Definitions
- This invention relates to the modification of cotton or cellulosic textile fabrics. In one specific aspect, it relates to a method for decreasing the flammability of such fabrics and the modified fabrics thereby produced.
- the present invention is a method for decreasing the flammability of a cellulosic fabric which comprises reacting the fabric with an aqueous solution containing sodium hypophosphite in the presence of ionizing radiation and then with an aqueous solution containing bromine.
- the invention also contemplates the modified cellulosic fabric thereby produced.
- NMA N- methylol acrylamide
- the fabric reacted with NMA containing acrylamidomethyl cellulose is padded with an aqueous solution containing sodium hypophosphite at approximately neutral pH (hypophosphorous acid brought to pH 7 by addition of sodium hydroxide or like base) to pick up the desired amount of sodium hypophosphite, at least about percent by weight based on the dry fabric.
- Exposure of the padded fabric to ionizing radiation generates free radicals and causes the hypophosphite to react with and become affixed to the unsaturated portion of the acrylamidomethyl cellulose entity in the fabric.
- the most convenient source of ionizing radiation currently available is gamma radiation from radioactive isotopes of cobalt and from various uranium fission products.
- Irradiation is easily controlled and the extent of treatment will depend on the energy of the treating source.
- the amount of radiation employed should be sufficient to cause a major portion of the hypophosphite to become affixed to the fabric; excess radiation, which would tend to degrade the fabric, should be avoided. Satisfactory results are obtained using about 2 megarads of ionizing radiation generally at room temperature.
- Rayon fabric containing about 17 percent N- methylol acrylamide and cotton fabric containing 12% NMA were padded with 30 percent and 20 percent solutions of sodium hypophosphite, respectively.
- the padded fabrics were dried and irradiated 10 hours (1.3 Mrads), washed, dried and weighed.
- the rayon increased in weight by about 15 percent and the cotton by about 6 percent based on dry weight of material.
- the process of the present invention is applicable to cellulose-containing fabrics generally.
- fabrics is meant to include textile fabrics of all kinds including woven and non-woven fabrics.
- the fabric may contain or be made from a natural cellulose material such as cotton or a regenerated cellulose material such as rayon.
- a method for decreasing the flammability of a cellulosic fabric which has been modified through reaction with an acidic solution of N-methylolacrylamide comprising reacting the fabric with an aqueous solution containing sodium hypophosphite in the presence of ionizing radiation and thereafter treating the fabric with an aqueous solution containing bromine.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Cellulosic fabrics are rendered less flammable by reaction of acrylamidomethyl cellulose with sodium hypophosphite in the presence of ionizing radiation and then with bromine.
Description
United States Patent 11 1 Walsh et al. a [451 Jan. 9, 1973 [54] METHOD FOR DECREASING THE [56] References Cited FLAMMABILITY OF CELLULOSIC UNITED STATES PATENTS FABRICS M 3,423,163 1 1969 t t l ..8 116.3 Inventors: William Kershlw Walsh; Henry 3,434,161 3/1969 I Ames Rutherford, both of Raleigh, 3,558,263 l/l97l Baitinger N.C. 3,300,273 l/l967 Kullman et a1. ..8/116.3 3,304,147 2/1967 Reinhardt et a1 ..8/116.3 Asslgnw Research Corponfiolh New York, 3,592,582 7/1971 Kullman et al. ..8/116.3 N.Y. 3,666,401 5/1972 Cahill et al. ..8/116.3 X
[22] Filed: NOV. 22, 1971 OTHER PUBLICATIONS PP N05 2011213 Walsh et al., Textile Research Journal, Vol. 35, pp.
52 us. Cl ..8/129, 8/116, 8/116 R, 'f' Emmi'fer-qemge Lesmes 8/1163, 8/120, 8/DlG. 18, 117/9331,
7 Attorney-Denms Clarke et a]. [51] Int. Cl ..D06m 13/40, @6111 15/36,
D06m 11/04 [57] ABSTRACT [58] Field of Senrch...8/l 16, 120, 116.3, 116 P, DIG. Cellulosic fabrics are rendered less flammable by reac- 18, 8/129 tion of acrylamidomethyl cellulose with sodium hypophosphite in the presence of ionizing radiation and then with bromine.
2 Claims, No Drawings METHOD FOR DECREASING THE FLAMMABILITY F CELLULOSIC FABRICS This invention relates to the modification of cotton or cellulosic textile fabrics. In one specific aspect, it relates to a method for decreasing the flammability of such fabrics and the modified fabrics thereby produced.
Cellulosic fabrics are widely used and the need for rendering such fabrics less flammable is very apparent. It is also known that the incorporation of phosphorous and/or halogen into fabrics decreases their flammability. However, prior art methods often result in other undesirable modifications of the fabric, such as making them stiff or harsh to the touch. We have discovered an improved approach to the incorporation of phosphorous and bromine into cellulosic fabrics wherein the soft hand of the fabric is not materially affected.
More specifically, the present invention is a method for decreasing the flammability of a cellulosic fabric which comprises reacting the fabric with an aqueous solution containing sodium hypophosphite in the presence of ionizing radiation and then with an aqueous solution containing bromine. The invention also contemplates the modified cellulosic fabric thereby produced.
In practicing the method of the present invention, the cellulosic fabric to be modified is treated with N- methylol acrylamide (NMA) in the presence of an acid catalyst according to the equation ll Cell-OH HOCHzNHC-CH=CH2 cellulose NMA ll Cell-OCHz--NHCCH=CH2 H2O acrylamidomethyl cellulose The procedure is described in more detail in US. Pat. No. 2,837,512 to Mantell.
The fabric reacted with NMA containing acrylamidomethyl cellulose is padded with an aqueous solution containing sodium hypophosphite at approximately neutral pH (hypophosphorous acid brought to pH 7 by addition of sodium hydroxide or like base) to pick up the desired amount of sodium hypophosphite, at least about percent by weight based on the dry fabric. Exposure of the padded fabric to ionizing radiation generates free radicals and causes the hypophosphite to react with and become affixed to the unsaturated portion of the acrylamidomethyl cellulose entity in the fabric. The most convenient source of ionizing radiation currently available is gamma radiation from radioactive isotopes of cobalt and from various uranium fission products. Irradiation is easily controlled and the extent of treatment will depend on the energy of the treating source. The amount of radiation employed should be sufficient to cause a major portion of the hypophosphite to become affixed to the fabric; excess radiation, which would tend to degrade the fabric, should be avoided. Satisfactory results are obtained using about 2 megarads of ionizing radiation generally at room temperature.
The resistance to burning of both cotton and rayon fabric were greatly improved by treatment with sodium hypophosphite. However, treatment with hypophosphite alone was not sufficient to completely inhibit combustion. It was found that reaction of residual double bonds in the phosphated acrylamidomethyl cellulose with bromine (aqueous bromine-bromide solution) made flame resistance virtually complete without adversely affecting the hand of the treated fabric. It was also found that the brominated fabrics had the added advantage of being somewhat anti-bacterial as determined by inhibition tests after incubation with nutrient media inoculated with staphylococcus. While this antibacterial effect diminished on repeated washing, it remained greater than that of untreated fabric.
Our invention is further described by means of the following illustrative examples:
1. Preparation of acrylamidomethyl cellulose Cotton fabric was padded with a solution containing 25 percent N-methylol acrylamide, 1 percent zinc nitrate, 1 percent hydroquinone and 0.1 percent surfactant to percent wet pickup, dried at 60 C., cured for 10 minutes at C. and then washed and dried. More conveniently, the fabric was padded with 25 percent NMA, 0.37 percent hydrochloric acid, and 0.1 percent surfactant, and then heated for 10 minutes at 70 C. without prior drying. The first method gave about a 12 percent increase in weight of cotton fabric and an 18 percent increase in weight of rayon treated. The second method gave about a 10 percent increase in weight for cotton and a 16 percent increase in weight for rayon.
2. Addition of sodium hypophosphite to acrylamidomethyl cellulose Acrylamidomethyl cellulose, cotton fabric with 11.1 percent weight gain from reaction with N-methylol acrylamide, was padded with an aqueous solution of sodium hypophosphite at pH 7. The padded fabric was dried, weighed, and irradiated with radioactive cobalt for 21 hours to a dose of 2.7 Mrads, washed and reweighed. The fabric containing 6.4 percent by weight of sodium hypophosphite after padding retained 5.1 percent of that salt after irradiation and washing.
Rayon fabric containing about 17 percent N- methylol acrylamide and cotton fabric containing 12% NMA were padded with 30 percent and 20 percent solutions of sodium hypophosphite, respectively. The padded fabrics were dried and irradiated 10 hours (1.3 Mrads), washed, dried and weighed. The rayon increased in weight by about 15 percent and the cotton by about 6 percent based on dry weight of material.
3. Addition of bromine to sodium hypophosphite containing acrylamidomethyl cellulose Cotton and rayon fabric treated according to the previous example were each immersed for 10 minutes in an aqueous solution containing 10 percent bromine and 15 percent potassium bromide. After rinsing and drying, additional weight gains of 3 percent and 7 percent for the rayon and cotton, respectively, were observed. The brominated fabrics had a soft hand.
When the brominated fabrics were subjected to the AATCC No. 344966 flammability test, the rayon showed zero afterflame and zero afterglow for both 12 and 2 second ignition times. The char lengths were 1.5
inches and less than 0.25 inches for the 12 second and 2 second ignition times, respectively. The cotton fabric, after twenty home launderings, had zero and 5 second afterflame times, zero afterglow, and 2.7 and 1.8 inch char lengths for the 12 second and 2 second ignition times. Untreated fabrics of the same type were virtually completely consumed in this test.
The process of the present invention is applicable to cellulose-containing fabrics generally. As used herein, the term fabrics" is meant to include textile fabrics of all kinds including woven and non-woven fabrics. The fabric may contain or be made from a natural cellulose material such as cotton or a regenerated cellulose material such as rayon.
Other variations in approach falling within the scope of the invention herein described will suggest themselves to those skilled in the art and our invention is as claimed.
We claim:
1. A method for decreasing the flammability of a cellulosic fabric which has been modified through reaction with an acidic solution of N-methylolacrylamide comprising reacting the fabric with an aqueous solution containing sodium hypophosphite in the presence of ionizing radiation and thereafter treating the fabric with an aqueous solution containing bromine.
2. A cellulosic fabric produced by the process of claim 1.
Claims (1)
- 2. A cellulosic fabric produced by the process of claim 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20121371A | 1971-11-22 | 1971-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3709658A true US3709658A (en) | 1973-01-09 |
Family
ID=22744936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00201213A Expired - Lifetime US3709658A (en) | 1971-11-22 | 1971-11-22 | Method for decreasing the flammability of cellulosic fabrics |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3709658A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4108748A (en) * | 1975-03-28 | 1978-08-22 | The United States Of America As Represented By The Secretary Of Agriculture | Photofinishing of cotton textiles |
| WO2000022222A1 (en) * | 1998-10-14 | 2000-04-20 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| WO2000029662A1 (en) * | 1998-11-13 | 2000-05-25 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| US6491727B1 (en) | 1999-06-09 | 2002-12-10 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| US20220161170A1 (en) * | 2019-03-26 | 2022-05-26 | Resolute Fp Canada, Inc. | Filter media, filters, and methods for making the same |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300273A (en) * | 1963-06-24 | 1967-01-24 | Russell M H Kullman | Production of cellulosic materials with oxidizing power |
| US3304147A (en) * | 1963-06-24 | 1967-02-14 | Robert M Reinhardt | Method of making cellulosic materials with oxidizing power |
| US3423163A (en) * | 1966-07-19 | 1969-01-21 | Du Pont | Cellulosic textile fibers bearing grafted n-methylol amide |
| US3434161A (en) * | 1965-10-05 | 1969-03-25 | Research Corp | Textile fabric treatment |
| US3558263A (en) * | 1968-10-01 | 1971-01-26 | American Cyanamid Co | Potassium iodide cross-linking inhibitor for n-methylolacrylamide |
| US3592582A (en) * | 1968-07-10 | 1971-07-13 | Us Agriculture | Process for production of cellulosic materials with increased oxidizing capacity |
| US3666401A (en) * | 1970-12-11 | 1972-05-30 | Atlantic Richfield Co | Treatment of textiles to impart wrinkle-resistant and fire-resistant properties |
-
1971
- 1971-11-22 US US00201213A patent/US3709658A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300273A (en) * | 1963-06-24 | 1967-01-24 | Russell M H Kullman | Production of cellulosic materials with oxidizing power |
| US3304147A (en) * | 1963-06-24 | 1967-02-14 | Robert M Reinhardt | Method of making cellulosic materials with oxidizing power |
| US3434161A (en) * | 1965-10-05 | 1969-03-25 | Research Corp | Textile fabric treatment |
| US3423163A (en) * | 1966-07-19 | 1969-01-21 | Du Pont | Cellulosic textile fibers bearing grafted n-methylol amide |
| US3592582A (en) * | 1968-07-10 | 1971-07-13 | Us Agriculture | Process for production of cellulosic materials with increased oxidizing capacity |
| US3558263A (en) * | 1968-10-01 | 1971-01-26 | American Cyanamid Co | Potassium iodide cross-linking inhibitor for n-methylolacrylamide |
| US3666401A (en) * | 1970-12-11 | 1972-05-30 | Atlantic Richfield Co | Treatment of textiles to impart wrinkle-resistant and fire-resistant properties |
Non-Patent Citations (1)
| Title |
|---|
| Walsh et al., Textile Research Journal, Vol. 35, pp. 648 654 (1965). * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4108748A (en) * | 1975-03-28 | 1978-08-22 | The United States Of America As Represented By The Secretary Of Agriculture | Photofinishing of cotton textiles |
| WO2000022222A1 (en) * | 1998-10-14 | 2000-04-20 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| WO2000029662A1 (en) * | 1998-11-13 | 2000-05-25 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| US6488718B1 (en) | 1998-11-13 | 2002-12-03 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| US6491727B1 (en) | 1999-06-09 | 2002-12-10 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| US20220161170A1 (en) * | 2019-03-26 | 2022-05-26 | Resolute Fp Canada, Inc. | Filter media, filters, and methods for making the same |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: UNIVERSITY OF NORTH CAROLINA, THE, (NORTH CAROLINA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:RESEARCH CORPORATION TECHNOLOGIES, INC., A NON-PROFIT CORP. OF DE.;REEL/FRAME:005437/0839 Effective date: 19891221 Owner name: RESEARCH CORPORATION TECHNOLOGIES, INC., 6840 EAST Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:RESEARCH CORPORATION, A NOT-FOR-PROFIT CORP. OF NY.;REEL/FRAME:005437/0829 Effective date: 19891221 |