US2993746A - Treatment of thpc flame-resistant fabrics with strong mineral acids to improve theirtear strength and products produced thereby - Google Patents
Treatment of thpc flame-resistant fabrics with strong mineral acids to improve theirtear strength and products produced thereby Download PDFInfo
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- US2993746A US2993746A US802579A US80257959A US2993746A US 2993746 A US2993746 A US 2993746A US 802579 A US802579 A US 802579A US 80257959 A US80257959 A US 80257959A US 2993746 A US2993746 A US 2993746A
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- fabric
- thpc
- flame
- tear strength
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- 239000004744 fabric Substances 0.000 title claims description 87
- 239000002253 acid Substances 0.000 title claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 title claims description 10
- 239000011707 mineral Substances 0.000 title claims description 10
- 238000011282 treatment Methods 0.000 title description 10
- 150000007513 acids Chemical class 0.000 title description 3
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 229920000877 Melamine resin Polymers 0.000 claims description 8
- 239000004640 Melamine resin Substances 0.000 claims description 8
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 230000003472 neutralizing effect Effects 0.000 claims description 8
- 229920002678 cellulose Polymers 0.000 claims description 7
- 239000001913 cellulose Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 230000007423 decrease Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 description 1
- 101000799461 Homo sapiens Thrombopoietin Proteins 0.000 description 1
- 102100034195 Thrombopoietin Human genes 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AKXUUJCMWZFYMV-UHFFFAOYSA-M tetrakis(hydroxymethyl)phosphanium;chloride Chemical compound [Cl-].OC[P+](CO)(CO)CO AKXUUJCMWZFYMV-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
- D06M15/43—Amino-aldehyde resins modified by phosphorus compounds
- D06M15/431—Amino-aldehyde resins modified by phosphorus compounds by phosphines or phosphine oxides; by oxides or salts of the phosphonium radical
Definitions
- This invention relates to a method of improving the tear strength of cellulosic fabrics which have been rendered flame resistant by impregnation with tetrakis-hydroxymethyl phosphonium chloride (THPC).
- THPC tetrakis-hydroxymethyl phosphonium chloride
- a substantial and surprising improvement in the tear strength of THPC treated fabrics can be effected by partial hydrolysis for a short time in a dilute mineral acid, preferably hydrochloric acid, e.g. of about 110% concentration.
- This hydrolysis is performed as an aftertreatrnent, and is preferably carried out at normal fabric washing temperatures, e.g., at 75100 C., followed by substantially neutralizing the fabric.
- Partial hydrolysis was carried out, by immersing the fabric in a solution of 2% hydrochloric acid and 5% urea, at 85 C. for various lengths of time, as shown in Table I below.
- the partially hydrolyzed fabric was then neutralized by immersion in a solution of 1% sodium carbonate, at 38 C., for 5 minutes, rinsed and dried at 90 C.
- the following results were obtained in determining the tear strength of the treated fabric samples:
- EXAMPLE II Carded sateen (8.5 oz. wt.) was treated with the standard THPC formulation as described in Example I except that plant equipment was used.
- the tear strength of the THPC treated fabric was 6.6 lbs. in the warp and 5.4 lbs. in the filling. This treatment was followed by a cold Water rinse and drying at C.
- the tear strength of the partially hydrolyzed and neutralized fabric was again determined and was found to have risen to 8.9 lbs. in the warp and 8.5 lbs. in the filling, which represents a substantial improvement.
- the fabric retained its flame resistance, and was resistant to subsequent Water leaching.
- EXAMPLE III EXAMPLE IV Example II was repeated with the use of a 2% hydrochloric acid solution, without urea, for the partial hydrolysis of the dried THPC-treated fabric. The results summerized in Table II, below, were obtained in determining the tear strength of fabric samples treated in accordance with this example:
- a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin comprising immersing the thus treated flame-resistant fabric in a dilute aqueous solution of a strong mineral acid until increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
- a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin comprising immersing the thus treated flame-resistant fabric in an aqueous solution of a strong mineral acid of about 110% concentration until the cellulose molecules of said fabric have been partially hydrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
- a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin comprising immersing the thus treated flame-resistant fabric in an aqueous solution of hydrochloric acid of about 1-10% concentration until the cellulose molecules of Said fabric 4 have been partially hydrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
- a method of improving the tearstrength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin comprising immersing the thus treated flame-resistant fabric in an aqueous solution of hydrochloric acid of about 140% concentration in the presence of urea until the cellulose molecules of said fabric have been partially hydrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
- a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin comprising immersing the thus treated flame-resistant fabric in an aqueous solution of about 2% hydrochloric acid and about 5% urea until the cellulose molecules of said fabric have been partially hpdrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
- a flame-resistant cellulosic fabric of improved tear strength produced by the method of claim 1.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
TREATMENT OF THPC FLAME-RESISTANT FAB- RICS WITH STRONG MINERAL ACIDS T IM- PROVE THEIR TEAR STRENGTH AND PROD- UCTS PRGDUCED THEREBY Thomas D. Miles, Southboro, and Francis A. Hoffman,
Millis, Mass., and Armando C. Delasanta, Woonsocket, R.I., assignors to the United States of America as represented by the Secretary of the Army No Drawing. Filed Mar. 27, 1959, Ser. No. 802,579
14 Claims. (Cl. 8116) (Granted under Title 35, U.S. Code (1952), see. 266) The invention described herein, if patented, may be manufactured and used by or for the Government for governmental purposes, without the payment to us of any royalty thereon.
This invention relates to a method of improving the tear strength of cellulosic fabrics which have been rendered flame resistant by impregnation with tetrakis-hydroxymethyl phosphonium chloride (THPC).
It is known that treatment of cotton fabrics and other cellulosic fabrics (e.g. linen fabrics), with THPC imparts a large degree of flame resistance to the treated fabrics. However, this desirable effect is largely offset by a marked decrease in tear strength, which greatly decreases the military and other utility of the flame-resistant fabrics thus produced.
We have now discovered a simple process whereby the tear strength of THPC-treated cellulosic fabrics can be greatly improved without substantially reducing their flame resistance.
More particularly, we have now found that a substantial and surprising improvement in the tear strength of THPC treated fabrics can be effected by partial hydrolysis for a short time in a dilute mineral acid, preferably hydrochloric acid, e.g. of about 110% concentration. This hydrolysis is performed as an aftertreatrnent, and is preferably carried out at normal fabric washing temperatures, e.g., at 75100 C., followed by substantially neutralizing the fabric.
The following examples illustrate the practice of our invention:
EXAMPLE I Carded sateen, cotton cloth (8.5 oz. weight) was treated with THPC as follows: a Solution A, containing 467 parts THPC, 450 parts water, and 84.5 parts triethanolamine, and Solution B, containing 267.8 parts methylol melamine resin, 278.5 parts urea, and 1265 parts water were prepared. The fabric was then passed through a solution made by combining Solution A and Solution B in a 1 to 1 ratio, using 2 dips and 2 nips to achieve a 60% wet pick-up. The treated fabric was oven dried at 85 C. for approximately 10 minutes followed by a 5-minute cure at 140 C. Partial hydrolysis was carried out, by immersing the fabric in a solution of 2% hydrochloric acid and 5% urea, at 85 C. for various lengths of time, as shown in Table I below. The partially hydrolyzed fabric was then neutralized by immersion in a solution of 1% sodium carbonate, at 38 C., for 5 minutes, rinsed and dried at 90 C. The following results were obtained in determining the tear strength of the treated fabric samples:
' atent Table I Tear Strength Fire Resistance (lbs.) Time of Hydrolysis (minutes) After After Char Warp Filling Flame Glow Length (sec (see) (in.)
0 untreated (no THPC)... 9. 6 11.7 0 treated (THPC) 4.1 3. 7 0 1. 6 3. 3 ltreated (THPC) 7.1 7.1 O 0 3.5 2 treated (THPC) 6. 4 6. 8 0 0.7 3. 7 3 treated (THPC). 5. 8 5. 4 0 0.7 3. 2 4 treated (THPO) 6.8 7.5 0 1.2 3.8 5 treated (THPC) 6.0 7. 7 0 0.3 6.5
EXAMPLE II Carded sateen (8.5 oz. wt.) was treated with the standard THPC formulation as described in Example I except that plant equipment was used. The tear strength of the THPC treated fabric was 6.6 lbs. in the warp and 5.4 lbs. in the filling. This treatment was followed by a cold Water rinse and drying at C. The tear strength of the partially hydrolyzed and neutralized fabric was again determined and was found to have risen to 8.9 lbs. in the warp and 8.5 lbs. in the filling, which represents a substantial improvement. The fabric retained its flame resistance, and was resistant to subsequent Water leaching.
EXAMPLE III EXAMPLE IV Example II was repeated with the use of a 2% hydrochloric acid solution, without urea, for the partial hydrolysis of the dried THPC-treated fabric. The results summerized in Table II, below, were obtained in determining the tear strength of fabric samples treated in accordance with this example:
Table II Tear Strength (lbs) Time of Hydrolysis (minutes) Warp Filling Untreated (no THPC) 11.6 i 12. 5 0 treated (THPC) 5. 3 5. 5 2 treated (THPC) 7. 3 7. 3 4 treated (THPOL. 7. 0 7. 8
' Laundering tests of the treated samples showed that fire resistance of the treated samples was retained through up to 9 launderingcyeles.
g It will'thus be seen that by the use of our method. of
after-treating a THPC-impregnated flame-resistant fabric with a strong mineral acid such as hydrochloric acid to effect a partial hydrolysis of the fabric,its tear strength is materially improved. Prior to our invention, it was not possible to use a THPC treated cellulosic fabric for I any purpose for which tear strength is important. While our invention does not completely restore the tear strength of the THPC treated fabric to the equivalent of that of the untreated (i.e. not flameproofed) fabric, it does improve the tear strength characteristics of the THPC- treated fabric to such an extent that it can be used as a tent fabric, tarpaulin, or other similar military or civilian textile item, for purposes where both flame strength and a degree of tear resistance are required. Thus, we have effected an acceptable and practical compromise between the high tear strength of a non-flameproofed cellulosic fabric, and the desirable flame resistance characteristics of a cellulosic fabric whose tear strength has been substantially reduced, however, by a fiame-resistance-imparting THPC treatment.
We are of course aware that we are not the first to treat cellulosic fabrics, such as cotton fabrics, with hydrochloric or other mineral acids. However, such treatments of the prior art are for an entirely different purpose, namely tomodify the appearance and feel of a nonflameproofed cotton fabric (parchmentizing) and such treatments have no effect on the tear strength of a chemically untreated cotton fabric. On the other hand, we believe ourselves to be the first to have discovered the beneficial effect of a hydrochloric acid or other mineral acid after-treatment of a THPC-impregnated flame-resistant fabric, so as to restore a large part of the loss of tear strength sufiered by the fabric by reason of the THPC treatment.
Without confining ourselves to any particular theory on which to base the efficiency of our invention, we postulate that the partial hydrolysis of the cellulose molecules effected by the hydrochloric acid (or other mineral acid) treatment counteracts the adverse eifect on the tear strength of the cellulosic fibers exerted by the bonding of the flameresistance-imparting impregnant.
It will of course be apparent to those skilled in the art that the operating conditions described in our foregoing specification and examples may be varied in a number of details without departing from the spirit of our invention. We thus intend to include any such changes and modifications within the scope of our invention, and to that end define our invention by the appended claims.
We claim:
1. In a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin, the improvement which comprises immersing the thus treated flame-resistant fabric in a dilute aqueous solution of a strong mineral acid until increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
2. In a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin, the improvement which comprises immersing the thus treated flame-resistant fabric in an aqueous solution of a strong mineral acid of about 110% concentration until the cellulose molecules of said fabric have been partially hydrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
3. In a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin, the improvement which comprises immersing the thus treated flame-resistant fabric in an aqueous solution of hydrochloric acid of about 1-10% concentration until the cellulose molecules of Said fabric 4 have been partially hydrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
4. In a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin, the improvement which comprises immersing the thus treater flame-resistant fabric in an aqueous solution of hydrochloric acid of about 2% concentration until the cellulose molecules of said fabric have been partially hydrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
5. In a method of improving the tearstrength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin, the improvement which comprises immersing the thus treated flame-resistant fabric in an aqueous solution of hydrochloric acid of about 140% concentration in the presence of urea until the cellulose molecules of said fabric have been partially hydrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
6. In a method of improving the tear strength of a cellulosic fabric which has been rendered flame-resistant with tetrakis-hydroxy-methyl phosphonium chloride and a methylol melamine resin, the improvement which comprises immersing the thus treated flame-resistant fabric in an aqueous solution of about 2% hydrochloric acid and about 5% urea until the cellulose molecules of said fabric have been partially hpdrolyzed and the tear strength of said fabric has been increased, then removing said fabric from said aqueous solution, substantially neutralizing said fabric, and rinsing and drying said fabric.
7. Method according to claim 1, wherein said fabric is neutralized in a dilute aqueous solution of sodium carbonate.
8. Method according to claim 3, wherein said fabric is neutralized in a dilute aqueous solution of sodium carbonate.
9. The method according to claim 1, wherein said aqueous solution has a temperature of about -100 C.
10. The method according to claim 3, wherein said aqueous solution has a temperature of about 75-100 C.
11. The method according to claim 5, wherein said aqueous solution has a temperature of about 75 -100 C.
12. The method according to claim 11, wherein said fabric is immersed in said aqueous solution for about one to five minutes.
13. The method according to' claim 1, wherein said fabric is immersed in said aqueous solution for about one to five. minutes. 7
14. A flame-resistant cellulosic fabric of improved tear strength produced by the method of claim 1.
References Cited in the file of this patent V UNITED STATES PATENTS 2,264,229 Wallach Nov. 25, 1941 2,648,597 Nielsen Aug. 11, 1953 2,668,096 Reeves Feb. 2, 1954 OTHER REFERENCES Campbell: Abstract 95,86 9, April 29, 1952 (657 O.G.
Ind. and Engineering Chem, December 1943, pp.
Claims (1)
1. IN A METHOD OF IMPROVING THE TEAR STRENGTH OF A CELLULOSIC FABRIC WHICH HAS BEEN RENDERED FLAME-RESISTANT WITH TETRAKIS-HYDROXY-METHYL PHOSPHONIUM CHLORIDE AND A METHYLOL MELAMINE RESIN, THE IMPROVEMENT WHICH COMPRISES IMMERSING THE THUS TREATED FLAME-RESISTANT FABRIC IN A DILUTE AQUEOUS SOLUTION OF A STRONG MINERAL ACID UNTIL THE CELLULOSE MOLECULES OF SAID FABRIC HAVE BEEN PARTIALLY HYDROLYZED AND THE TEAR STRENGTH OF SAID FABRIC HAS BEEN INCREASED, THEN REMOVING SAID FABRIC FROM SAID AQUEOUS SOLUTION, SUBSTANTIALLY NEUTRALIZING SAID FABRIC, AND RINSING AND DRYING SAID FABRIC.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US802579A US2993746A (en) | 1959-03-27 | 1959-03-27 | Treatment of thpc flame-resistant fabrics with strong mineral acids to improve theirtear strength and products produced thereby |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US802579A US2993746A (en) | 1959-03-27 | 1959-03-27 | Treatment of thpc flame-resistant fabrics with strong mineral acids to improve theirtear strength and products produced thereby |
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| Publication Number | Publication Date |
|---|---|
| US2993746A true US2993746A (en) | 1961-07-25 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US802579A Expired - Lifetime US2993746A (en) | 1959-03-27 | 1959-03-27 | Treatment of thpc flame-resistant fabrics with strong mineral acids to improve theirtear strength and products produced thereby |
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| Country | Link |
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| US (1) | US2993746A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3101279A (en) * | 1960-11-21 | 1963-08-20 | Hooker Chemical Corp | Flame proofing of cellulosic materials |
| US3101278A (en) * | 1960-11-21 | 1963-08-20 | Hooker Chemical Corp | Flame proofing of cellulosic materials |
| US3219407A (en) * | 1960-06-01 | 1965-11-23 | Hoechst Ag | Vinyl phosphonic acid polymers and derivatives thereof as acidic catalysts in a process of creaseproofing cellulose textiles |
| DE1285442B (en) * | 1963-04-16 | 1968-12-19 | Hooker Chemical Corp | Process for flame retardant finishing of cellulose textiles |
| US3473948A (en) * | 1966-09-29 | 1969-10-21 | Burlington Industries Inc | Method of improving resin finished textiles |
| US3488139A (en) * | 1966-04-18 | 1970-01-06 | Hooker Chemical Corp | Textile treating process |
| USB328205I5 (en) * | 1972-01-04 | 1975-01-28 | ||
| US3864076A (en) * | 1971-09-10 | 1975-02-04 | Ciba Geigy Ag | Process for flameproofing organic fibers with phosphorus-containing condensation products and the products produced |
| US3887553A (en) * | 1972-01-14 | 1975-06-03 | Ciba Geigy Ag | Process for the manufacture of phosphorus-containing condensation products |
| US4026889A (en) * | 1972-01-14 | 1977-05-31 | Ciba-Geigy Corporation | Phosphorus-containing condensation products |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2264229A (en) * | 1937-11-02 | 1941-11-25 | Sylvania Ind Corp | Process for treating fibers and the products produced |
| US2648597A (en) * | 1951-03-24 | 1953-08-11 | Monsanto Chemicals | Chemical process |
| US2668096A (en) * | 1952-04-22 | 1954-02-02 | Wilson A Reeves | Flameproof fibrous aminoethylated cellulose derivatives |
-
1959
- 1959-03-27 US US802579A patent/US2993746A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2264229A (en) * | 1937-11-02 | 1941-11-25 | Sylvania Ind Corp | Process for treating fibers and the products produced |
| US2648597A (en) * | 1951-03-24 | 1953-08-11 | Monsanto Chemicals | Chemical process |
| US2668096A (en) * | 1952-04-22 | 1954-02-02 | Wilson A Reeves | Flameproof fibrous aminoethylated cellulose derivatives |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3219407A (en) * | 1960-06-01 | 1965-11-23 | Hoechst Ag | Vinyl phosphonic acid polymers and derivatives thereof as acidic catalysts in a process of creaseproofing cellulose textiles |
| US3101279A (en) * | 1960-11-21 | 1963-08-20 | Hooker Chemical Corp | Flame proofing of cellulosic materials |
| US3101278A (en) * | 1960-11-21 | 1963-08-20 | Hooker Chemical Corp | Flame proofing of cellulosic materials |
| DE1285442B (en) * | 1963-04-16 | 1968-12-19 | Hooker Chemical Corp | Process for flame retardant finishing of cellulose textiles |
| US3488139A (en) * | 1966-04-18 | 1970-01-06 | Hooker Chemical Corp | Textile treating process |
| US3473948A (en) * | 1966-09-29 | 1969-10-21 | Burlington Industries Inc | Method of improving resin finished textiles |
| US3864076A (en) * | 1971-09-10 | 1975-02-04 | Ciba Geigy Ag | Process for flameproofing organic fibers with phosphorus-containing condensation products and the products produced |
| USB328205I5 (en) * | 1972-01-04 | 1975-01-28 | ||
| US3914106A (en) * | 1972-01-04 | 1975-10-21 | Us Agriculture | Process for treating organic textiles with flame retardant polymers made from hydroxymethylphosphorus compounds and guanazoles |
| US3887553A (en) * | 1972-01-14 | 1975-06-03 | Ciba Geigy Ag | Process for the manufacture of phosphorus-containing condensation products |
| US4026889A (en) * | 1972-01-14 | 1977-05-31 | Ciba-Geigy Corporation | Phosphorus-containing condensation products |
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