US3156521A - Process of bleaching textiles with lower alkyl quaternary ammonium perhalides - Google Patents
Process of bleaching textiles with lower alkyl quaternary ammonium perhalides Download PDFInfo
- Publication number
- US3156521A US3156521A US146357A US14635761A US3156521A US 3156521 A US3156521 A US 3156521A US 146357 A US146357 A US 146357A US 14635761 A US14635761 A US 14635761A US 3156521 A US3156521 A US 3156521A
- Authority
- US
- United States
- Prior art keywords
- bleaching
- lower alkyl
- quaternary ammonium
- compounds
- alkyl quaternary
- 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
- 238000004061 bleaching Methods 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 7
- 239000004753 textile Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000835 fiber Substances 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229920000742 Cotton Polymers 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000007844 bleaching agent Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 4
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- IFIDXBCRSWOUSB-UHFFFAOYSA-N potassium;1,3-dichloro-1,3,5-triazinane-2,4,6-trione Chemical compound [K+].ClN1C(=O)NC(=O)N(Cl)C1=O IFIDXBCRSWOUSB-UHFFFAOYSA-N 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GPZVUOSXHJGAKW-UHFFFAOYSA-N Cl[O-].[K+].[Na+].Cl[O-] Chemical compound Cl[O-].[K+].[Na+].Cl[O-] GPZVUOSXHJGAKW-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- -1 sodium hypochlorite Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229950009390 symclosene Drugs 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/20—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which contain halogen
- D06L4/27—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which contain halogen using organic agents
-
- 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
- Y10S8/06—Resin bleach
Definitions
- Inorganic hypochlorites particularly sodium hypochlorite
- sodium hypochlorite although recognized as an effective and relatively cheap bleaching agent, has certain inherent disadvantages. Because of its instability, it can be handled only as a dilute aqueous solution requiring bulky and inconvenient containers and having a limited shelf life. Hypochlorites also have a damaging effect on fabric tensile strength.
- organic nitrogen compounds containing nitrogen-bonded chlorine atoms in their structure have been offered for bleaching use, for example, trichloroisocyanuric acid, potassium dichloroisocyanurate, dichlorodirnethylhydantoin, and related compounds.
- trichloroisocyanuric acid potassium dichloroisocyanurate
- dichlorodirnethylhydantoin and related compounds.
- these materials are not entirely suitable for the purpose, having one or more of such disadvantages as poor dry stability, insufiicient water solubility, or low bleaching efficiency.
- Chlorine-liberating bleaches such as those described above also tend to attack the structure of many textile fibers, causing yellowing and a loss of tensile strength. This elfect is particularly noticeable in fibers having nitrogen atoms associated with their structure; for example, silk, wool, synthetic polyamides, or fibers coated or impregnated with nitrogen-containing materials such as melamine resin-finished cotton.
- the perhalide compounds described above have been found to be effective and advantageous bleaching agents when applied in water dispersion to various substances having undesirable and bleachable color or stain.
- Straw, Wood pulp, paper stock, leather, various natural fibers such as cotton, silk, wool, and linen, and synthetic polyamide, polyester, and other like fibers may be treated by this process to remove natural or foreign discoloration.
- perhalides are crystalline solids which are stable while dry and they may be incorporated as bleaching components of various dry formulations for household and industrial use.
- the tetraalkyl ammonium perhalides are relatively soluble in water and, when so dissolved, readily liberate two atoms of halogen per molecule.
- Dichlorobromides liberate one atom each of chlorine and bromine while dibromochlorides and tribromides liberate two atoms of bromine.
- EXAMPLE 1 One liter portions of water in stainless steel beakers were heated to 130 F., the bleaching compounds to be tested were dissolved in the respective beakers of water, and the pH of each test solution was adjusted to 9-10 where necessary by the addition of tetrapotassium pyrophosphate. Bleaching efficiencies were measured at concentrations of 300 p.p.m. available halogen calculated as chlorine. Available halogen was determined by titration of iodine released from an acidified KI solution by a known quantity of perhalide. Three 5-inch squares of unbleached cotton sheeting were bleached for 10 minutes with agitation in each test solution, the cloths were rinsed 5 minutes in water, and they were pressed dry with a hand iron. The average reflectance of the three swatches of cotton sheeting as measured by a reflectometer was taken as a measure of bleach performance. The figures given are percentages based on a magnesium oxide block standard which is assigned a value of reflectance.
- EXAMPLE 2 In the manner described above, samples of white melamine resin-finished cotton print cloth were treated with various bleaching compounds and rinsed with water. These samples were dried in an electric dryer and inspected visually for yellowing. Table 2 lists data obtained at bleach concentrations of 300, 500, and 700 p.p.m. available halogen as chlorine.
- these compounds are not only eflicient bleaches, but also show low redeposition of stain upon the bleached fabric.
- a further advantage of these perhalides lies in the biocidal free halogen which is liberated upon contact with water, thereby making these compounds disinfectants as well as bleaches.
- a process for bleaching natural and synthetic fibers which comprises applying to said fibers a Water dispersion having dissolved therein an effective amount of a compound having the structure R NBr Cl wherein each R is a lower alkyl radical containing about 1-6 carbon atoms and n is an integer from one to three inclusive.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
Description
United States Patent This invention relates to organic bleaching compositions having advantageous properties.
Compounds and compositions capable of releasing chlorine have long been known and used for bleaching and stain removal. Inorganic hypochlorites, particularly sodium hypochlorite, are widely used for the purpose. Sodium hypochlorite, although recognized as an effective and relatively cheap bleaching agent, has certain inherent disadvantages. Because of its instability, it can be handled only as a dilute aqueous solution requiring bulky and inconvenient containers and having a limited shelf life. Hypochlorites also have a damaging effect on fabric tensile strength. Recently, organic nitrogen compounds containing nitrogen-bonded chlorine atoms in their structure have been offered for bleaching use, for example, trichloroisocyanuric acid, potassium dichloroisocyanurate, dichlorodirnethylhydantoin, and related compounds. These have the advantage of being solids and therefore are capable of being formulated into solid bleaching compositions, bleaching cleansers, and the like. However, these materials are not entirely suitable for the purpose, having one or more of such disadvantages as poor dry stability, insufiicient water solubility, or low bleaching efficiency.
Chlorine-liberating bleaches such as those described above also tend to attack the structure of many textile fibers, causing yellowing and a loss of tensile strength. This elfect is particularly noticeable in fibers having nitrogen atoms associated with their structure; for example, silk, wool, synthetic polyamides, or fibers coated or impregnated with nitrogen-containing materials such as melamine resin-finished cotton.
It has now been found that many of the above-mentioned disadvantages are largely overcome or avoided by the use as bleaches of certain tetraalkyl ammonium perhalides. Most effective for the purpose are the perhalides having the structure R NBr Cl( wherein each R is a lower alkyl radical containing 1-6 carbon atoms and n is an integer from one to three inclusive. The compounds included are therefore the tetraalkyl ammonium dichlorobromides, dibromochlorides, and tribromides. Most preferred, particularly on economic grounds, are the dichlorobromides. Compounds wherein at least three Rs are methyl are advantageous because of their relatively higher water solubility.
The perhalide compounds described above have been found to be effective and advantageous bleaching agents when applied in water dispersion to various substances having undesirable and bleachable color or stain. Straw, Wood pulp, paper stock, leather, various natural fibers such as cotton, silk, wool, and linen, and synthetic polyamide, polyester, and other like fibers may be treated by this process to remove natural or foreign discoloration.
These perhalides are crystalline solids which are stable while dry and they may be incorporated as bleaching components of various dry formulations for household and industrial use. The tetraalkyl ammonium perhalides are relatively soluble in water and, when so dissolved, readily liberate two atoms of halogen per molecule. Dichlorobromides liberate one atom each of chlorine and bromine while dibromochlorides and tribromides liberate two atoms of bromine.
These compounds have been found to have particular advantage in the bleaching of fabrics which have been treated with nitrogen-containing resins for crease resistance. Specifically, melamine resin-treated cotton may be bleached by these compounds with less yellowing and weakening of the fabric than is possible with the commonly used chlorine bleaches. These results are obtained along with bleaching efliciencies at least as high as those shown by chorine-liberating bleaches when used in equivalent halogen concentrations.
EXAMPLE 1 One liter portions of water in stainless steel beakers were heated to 130 F., the bleaching compounds to be tested were dissolved in the respective beakers of water, and the pH of each test solution was adjusted to 9-10 where necessary by the addition of tetrapotassium pyrophosphate. Bleaching efficiencies were measured at concentrations of 300 p.p.m. available halogen calculated as chlorine. Available halogen was determined by titration of iodine released from an acidified KI solution by a known quantity of perhalide. Three 5-inch squares of unbleached cotton sheeting were bleached for 10 minutes with agitation in each test solution, the cloths were rinsed 5 minutes in water, and they were pressed dry with a hand iron. The average reflectance of the three swatches of cotton sheeting as measured by a reflectometer was taken as a measure of bleach performance. The figures given are percentages based on a magnesium oxide block standard which is assigned a value of reflectance.
Table I Bleaching compound: Average reflectance Sodium hypochlorite 84.5 (CH C H NBrCl 84.3 (CH3)3C2H5NC1BI2 (CH C H NBrCl 84.2 (CH NBrCl 84.3
EXAMPLE 2 In the manner described above, samples of white melamine resin-finished cotton print cloth were treated with various bleaching compounds and rinsed with water. These samples were dried in an electric dryer and inspected visually for yellowing. Table 2 lists data obtained at bleach concentrations of 300, 500, and 700 p.p.m. available halogen as chlorine.
Table II Relative Yellowing Bleaching Compounds 300 p.p.m. 500 p.p.m.
700 p.p.m. C1 C1 C12 Moderatedo..
Sodium hypochlorite Potassium dichloroisocya Heavy. Moderate.
Very slight. Do.
Do. Do.
Very slight" Very slight d do do do EXAMPLE 3 Table III Tensile Strength, lbs.
Bleaching Compound Regular Resin- Cotton finished Cotton Sodium hypochlorite 40.3 27 6 Potassium dichloroisocyanurate 34.3 28 1 (CH3) C2H5NBIC12 38. 3 31. 6 (CI-Ia)aO H NClBr 41. 2 34. 9 (CH3) 3C4H9NBIC1; 37.5 33. 5 (C1I3)4NBIO]2 40.8 33 0 Blank 51. 3 33 8 The tetraalkyl ammonium perhalides are also advantageous in that they are effective bleaching agents in acidic solutions although best results are obtained at high pH levels, a pH of about 911 being preferred. Additionally, at both high and low pH, these compounds are not only eflicient bleaches, but also show low redeposition of stain upon the bleached fabric. A further advantage of these perhalides lies in the biocidal free halogen which is liberated upon contact with water, thereby making these compounds disinfectants as well as bleaches.
I claim:
1. A process for bleaching natural and synthetic fibers which comprises applying to said fibers a Water dispersion having dissolved therein an effective amount of a compound having the structure R NBr Cl wherein each R is a lower alkyl radical containing about 1-6 carbon atoms and n is an integer from one to three inclusive.
2. The process of claim 1 where in n is one.
3. The process of claim 2 wherein at least three of the Rs are methyl radicals.
4. The process of claim 2 wherein the fiber bleached is melamine resin-finished cotton.
References Cited in the file of this patent UNITED STATES PATENTS 2,256,958 Muskat Sept. 23, 1941 2,430,233 Magill Nov. 4, 1947 2,913,460 Brown Nov. 17, 1959 2,929,816 Chamberlain May 22, 1960 2,945,061 Habernickel July 12, 1960 2,972,620 Simmons Feb. 21, 1961 2,980,488 Kokorudz Apr. 18, 1961 S- PATENT OFFICE OF CORRECTION November l0 UNITED STATE CERTIFICATE Patent No Jack mbered pat- T1; is hereby c on and that the said Le ent requiring correcti (1 below.
lowing:
correc'te after line 23, insert the fol Column l,
OTHER REFERENCES Chattaway et al, q Jo Chem. Soc; (London) l23 Pages (1923) through l1 Ghemo Abstr. 1949 (1923). n.
y of April 1965.
(SEAL) Commissioner of Patents ERNEST W. SWlDER Attest'mg Officer
Claims (1)
1. A PROCESS FOR BLEACHING NATURAL AND SYNTHETIC FIBERS WHICH COMPRISES APPLYING TO SAID FIBERS A WATER DISPERSION HAVING DISSOLVED THEREIN AN EFFECTIVE AMOUNT OF A COMPOUND HAVING THE STRUCTURE R4NBRNCL(3-N) WHEREIN EACH R IS A LOWER ALKYL RADICAL CONTAINING ABOUT 1-6 CARBON ATOMS AND N IS AN INTEGER FROM ONE TO THREE INCLUSIVE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US146357A US3156521A (en) | 1961-10-19 | 1961-10-19 | Process of bleaching textiles with lower alkyl quaternary ammonium perhalides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US146357A US3156521A (en) | 1961-10-19 | 1961-10-19 | Process of bleaching textiles with lower alkyl quaternary ammonium perhalides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3156521A true US3156521A (en) | 1964-11-10 |
Family
ID=22517015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US146357A Expired - Lifetime US3156521A (en) | 1961-10-19 | 1961-10-19 | Process of bleaching textiles with lower alkyl quaternary ammonium perhalides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3156521A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3475493A (en) * | 1964-05-08 | 1969-10-28 | Fmc Corp | Quaternary ammonium peroxysulfates |
| US4353866A (en) * | 1980-11-05 | 1982-10-12 | The Procter & Gamble Company | Activation of hypochlorite bleaching of dyes |
| US4384869A (en) * | 1980-11-05 | 1983-05-24 | The Procter & Gamble Company | Activation of hypochlorite bleaching of dyes |
| US4420412A (en) * | 1980-11-05 | 1983-12-13 | The Procter & Gamble Company | Activation of hypochlorite bleaching of dyes |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2256958A (en) * | 1939-05-13 | 1941-09-23 | Pittsburgh Plate Glass Co | Quaternary ammonium hypohalites and method of making same |
| US2430233A (en) * | 1944-06-05 | 1947-11-04 | Du Pont | Halogen-yielding compositions |
| US2913460A (en) * | 1956-09-10 | 1959-11-17 | Procter & Gamble | Composition having bleaching, sterilizing and disinfecting properties, and method of preparation thereof |
| US2929816A (en) * | 1960-03-22 | Cinci | ||
| US2945061A (en) * | 1954-01-07 | 1960-07-12 | Henkel & Compagnie G M B H | Process for the production of biguanide derivatives containing active chlorine |
| US2972620A (en) * | 1959-06-29 | 1961-02-21 | Du Pont | 2-haloimino-1, 3-dioxolanes and method of production |
| US2980488A (en) * | 1958-06-23 | 1961-04-18 | Wyandotte Chemicals Corp | Method of bleaching cotton fabrics with tetrachloromalonamides |
-
1961
- 1961-10-19 US US146357A patent/US3156521A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2929816A (en) * | 1960-03-22 | Cinci | ||
| US2256958A (en) * | 1939-05-13 | 1941-09-23 | Pittsburgh Plate Glass Co | Quaternary ammonium hypohalites and method of making same |
| US2430233A (en) * | 1944-06-05 | 1947-11-04 | Du Pont | Halogen-yielding compositions |
| US2945061A (en) * | 1954-01-07 | 1960-07-12 | Henkel & Compagnie G M B H | Process for the production of biguanide derivatives containing active chlorine |
| US2913460A (en) * | 1956-09-10 | 1959-11-17 | Procter & Gamble | Composition having bleaching, sterilizing and disinfecting properties, and method of preparation thereof |
| US2980488A (en) * | 1958-06-23 | 1961-04-18 | Wyandotte Chemicals Corp | Method of bleaching cotton fabrics with tetrachloromalonamides |
| US2972620A (en) * | 1959-06-29 | 1961-02-21 | Du Pont | 2-haloimino-1, 3-dioxolanes and method of production |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3475493A (en) * | 1964-05-08 | 1969-10-28 | Fmc Corp | Quaternary ammonium peroxysulfates |
| US4353866A (en) * | 1980-11-05 | 1982-10-12 | The Procter & Gamble Company | Activation of hypochlorite bleaching of dyes |
| US4384869A (en) * | 1980-11-05 | 1983-05-24 | The Procter & Gamble Company | Activation of hypochlorite bleaching of dyes |
| US4420412A (en) * | 1980-11-05 | 1983-12-13 | The Procter & Gamble Company | Activation of hypochlorite bleaching of dyes |
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