US3172861A - Hypochlorite bleaching compositions - Google Patents
Hypochlorite bleaching compositions Download PDFInfo
- Publication number
- US3172861A US3172861A US3172861DA US3172861A US 3172861 A US3172861 A US 3172861A US 3172861D A US3172861D A US 3172861DA US 3172861 A US3172861 A US 3172861A
- Authority
- US
- United States
- Prior art keywords
- sodium
- oxide
- diphenyl oxide
- hypochlorite
- bleaching
- 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
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- WQYVRQLZKVEZGA-UHFFFAOYSA-N Hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 title description 26
- 238000004061 bleaching Methods 0.000 title description 16
- 239000000203 mixture Substances 0.000 title description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N Diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 10
- 239000007844 bleaching agent Substances 0.000 claims description 10
- XSAHYEQPUFJGKW-UHFFFAOYSA-N 1-dodecyl-4-phenoxybenzene Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1OC1=CC=CC=C1 XSAHYEQPUFJGKW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000009898 sodium hypochlorite bleaching Methods 0.000 claims description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000000243 solution Substances 0.000 description 40
- 239000011734 sodium Substances 0.000 description 32
- 239000004094 surface-active agent Substances 0.000 description 20
- 239000006260 foam Substances 0.000 description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- -1 alkali metal salt Chemical class 0.000 description 12
- SUKJFIGYRHOWBL-UHFFFAOYSA-N Sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 8
- 235000019589 hardness Nutrition 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000005708 Sodium hypochlorite Substances 0.000 description 4
- FPKOPBFLPLFWAD-UHFFFAOYSA-N Trinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O FPKOPBFLPLFWAD-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 125000004432 carbon atoms Chemical group C* 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- PGPNJCAMHOJTEF-UHFFFAOYSA-N 1-chloro-4-phenoxybenzene Chemical compound C1=CC(Cl)=CC=C1OC1=CC=CC=C1 PGPNJCAMHOJTEF-UHFFFAOYSA-N 0.000 description 2
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 2
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005282 brightening Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NHYCGSASNAIGLD-UHFFFAOYSA-N chlorine monoxide Inorganic materials Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 2
- 230000002708 enhancing Effects 0.000 description 2
- YZQBYALVHAANGI-UHFFFAOYSA-N magnesium;dihypochlorite Chemical compound [Mg+2].Cl[O-].Cl[O-] YZQBYALVHAANGI-UHFFFAOYSA-N 0.000 description 2
- URXNVXOMQQCBHS-UHFFFAOYSA-N naphthalene;sodium Chemical compound [Na].C1=CC=CC2=CC=CC=C21 URXNVXOMQQCBHS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- DGSDBJMBHCQYGN-UHFFFAOYSA-M sodium;2-ethylhexyl sulfate Chemical compound [Na+].CCCCC(CC)COS([O-])(=O)=O DGSDBJMBHCQYGN-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
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
- D06L4/22—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which contain halogen using inorganic agents
- D06L4/23—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which contain halogen using inorganic agents using hypohalogenites
Definitions
- the present invention relates to novel and useful improved bleaching solutions. More particularly the present invention concerns the use of a novel surfactant in hypochlorite bleaching solutions to impart foaming and additional cleaning and bleaching power to such solutions.
- an alkali metal salt of an alkylated diphenyl oxide sulfonic acid when added in amounts of from about 1 to 100% by weight based on the active bleaching agent of a bleaching composition, will enhance bleaching, cleaning and brightening power of compositions of both household and industrial strengths.
- the desirability of adding a surfactant is increased since the foaming attendant with the use is an indication of the amount of bleaching solution added.
- alkylated diphenyl oxide sulfonic acid alkali metal salts and their nuclearly mono and dichlorinated derivatives, suitable for use in accordance with the present invention are those having from 8 to 22 carbon atoms in the alkyl chain and an average of from 1.8 to 2.3 sulfonate moieties per diphenyl oxide moiety.
- Triton X100 manufactured by Rohm & Haas Co.
- EXAMPLE 2 The surface tension of various concentrations of alkylated diphenyl oxide disulfonic acid, sodium salt, in aqueous 5% sodium hypochlorite solutions is reported in Table II below.
- the test solution was prepared from 27 ml. of aqueous 5% hypochlorite solution containing 0.2% or 0.4% by weight of a surfactant and 973 ml. of tap water having 70 ppm. hardness at 25 C.
- EXAMPLE 3 Two grams of one of several surfactants, e.g., sodium pentadecyldiphenyl oxide sulfonate, was added to 1000 grams of aqueous 5% hypochlorite solution (Clorox). Twenty-seven ml. of the above solution was added to 973 ml. water having a hardness of 70 ppm. as CaCO The above solution was then tested on the Ross-Miles Foam Tower. The test is carried out in the following manner.
- surfactants e.g., sodium pentadecyldiphenyl oxide sulfonate
- EXAMPLE 4 The following example illustrates the effectiveness of the surfactants in water of various hardnesses.
- the Ross Miles Foam Tower test was conducted in the manner of Example 2 using a solution prepared from 27 ml. of an aqueous 5% hypochlorite solution containing 0.2% by weight of sodium pentadecyldiphenyl oxide disulfonate and 973 ml. of water of various hardnesses. The results of such tests are indicated in Table IV.
- bleaching agents other than sodium hypochlorite can beenhanced in the foregoing manner.
- Some of such agents are the hypochlorites, i.e., sodium, potassium, calcium or magnesium hypochlorite, as well as chloride of lime (CaCl-Ca(ClO)).
- An aqueous 5 percent by weight sodium hypochlorite bleaching solution containing from about 1 to 100% by weight based on the active bleaching agent of a compound selected from the group consisting of alkali metal salts of an alkylated diphenyl oxide sulfonic acid and their nuclearly mono and dichlorinated derivatives having from 8 to 22 carbon atoms in the alkyl moiety and an average of from 1.8 to 2.3 sulfonate moieties per diphenyl oxide moiety.
- An aqueous 5 percent by weight sodium hypochlorite bleaching solution containing from 1 to 100% by weight based on the active bleaching agent of a sodium dodecyl diphenyl oxide sulfonate having an average of about 2 sulfonate radicals per diphenyl oxide moiety.
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- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
Description
United States Patent 3,172,861 HYPOCHLORITE BLEACHING COMPOSITIONS Alfred F. Steinhauer and Joseph C. Valenta, Midland, Mich., assignors to The Dow Chemical Company, Midland, Mich, a corporation of Delaware No Drawing. Filed May 25, 1961, Ser. No. 112,512 2 Claims. (Cl. 252-187) The present invention relates to novel and useful improved bleaching solutions. More particularly the present invention concerns the use of a novel surfactant in hypochlorite bleaching solutions to impart foaming and additional cleaning and bleaching power to such solutions.
It has now been found that an alkali metal salt of an alkylated diphenyl oxide sulfonic acid, when added in amounts of from about 1 to 100% by weight based on the active bleaching agent of a bleaching composition, will enhance bleaching, cleaning and brightening power of compositions of both household and industrial strengths. The desirability of adding a surfactant is increased since the foaming attendant with the use is an indication of the amount of bleaching solution added.
The alkylated diphenyl oxide sulfonic acid alkali metal salts and their nuclearly mono and dichlorinated derivatives, suitable for use in accordance with the present invention are those having from 8 to 22 carbon atoms in the alkyl chain and an average of from 1.8 to 2.3 sulfonate moieties per diphenyl oxide moiety.
The following examples illustrate the present invention but are not to be construed as limiting:
EXAMPLE 1 The solubility of 0.1% by weight of surfactant in aqueous sodium hypochlorate solutions at 25 C. for varioiis surfactants is recorded in Table I.
3,172,851 Patented Mar. 9, 1965 "ice Sodium pentadecyldiphenyl oxide disulfonate SC S: soluble, I:inso1uble, C: clear solution.
1 Ultrawet K, manufactured by Atlantic Refining Co.
3 lgiuponol ME, manufactured by E. I. du Pont de Nemours an o.
EDCUDOIIOI C, manufactured by E. I. du Pont de Nemours an 0.
* Stepan LDA, manufactured by Stepan Chemical Co.
5 Triton X100, manufactured by Rohm & Haas Co.
6 Tergitol O8, manufactured by Union Carbide Co.
Became cloudy with precipitate after 6 weeks shelf storage.
* Clear after 4 months shelf storage.
EXAMPLE 2 The surface tension of various concentrations of alkylated diphenyl oxide disulfonic acid, sodium salt, in aqueous 5% sodium hypochlorite solutions is reported in Table II below. The test solution was prepared from 27 ml. of aqueous 5% hypochlorite solution containing 0.2% or 0.4% by weight of a surfactant and 973 ml. of tap water having 70 ppm. hardness at 25 C.
Tabl II Concentration of Surfactant Surface Surfactant in Test Solu- Tension tion (Percent dynes by Weight) Sodium dodecyldiphenyl oxide disulfonate. 0. 0054 43. 0 D0 0. 0108 41. 1 Sodium pentadecyldiphenyl oxide disulfonate 0. 0054 46. 5 D 0 0. 0108 45. 5 No Surfactant 55.2
Table III 0 ompound Foam Height in mm. for Solutions After Standing 6 Weeks Before Foam Height in mm.
Testing Measurement Time, Minutes Measurement Time, Minutes Alkyl naphthalene sodium sulfonate 1 5 5 0 Sodium sulfate derivative of 2-ethyl-1-hexano1 30 0 Na dodecyldiphenyl oxide disullonate. 110 90 63 48 Na pentadecyldiphenyl oxide disulionate 135 118 115 110 Isooetylphenyl polyethoxyetha-ne 55 55 50 Na nonyl diphenyl oxide disulfonat 40 28 25 Na octyl diphenyl oxide disulionate 70 30 22 12 Na dodecyl monochlorodiphenyl oxide disul a 100 67 58 Na a-methylheptadecyldiphenyl oxide disulfonate. 85 78 72 65 Na monolauryldiphenyl oxide disulfonate 125 100 80 INCREASE SURFAOTANT CONC. TO 108 Sodium sulfate derivative of Z-ethyl-l-hexanol Na dodecyldiphenyl oxidedisulfonate Na pentadecyldiphenyl oxide (lisulfonate 1 Petro AA manufactured by Petrochemicals Co. 2 Tergitol 08.
3 Triton X100.
4 Sample was cloudy with precipitate.
Sample was shaken to disperse precipitate before test.
3 EXAMPLE 3 Two grams of one of several surfactants, e.g., sodium pentadecyldiphenyl oxide sulfonate, was added to 1000 grams of aqueous 5% hypochlorite solution (Clorox). Twenty-seven ml. of the above solution was added to 973 ml. water having a hardness of 70 ppm. as CaCO The above solution was then tested on the Ross-Miles Foam Tower. The test is carried out in the following manner.
One hundred cubic centimeters of a solution prepared in the above manner was pipetted into the Foam Tower directing the flow in such a way that it flows down the side Walls of the tower so as not to produce any foam. The same solution was placed in a dropping funnel, the stopcock opened, and the 200 cc. of solution allowed to fall into the 100 cc. of solution in the bottom of the tower. The height of the foam, in millimeters, was measured immediately and each minute of standing for a total of five minutes and the measurements recorded in Table III.
A second series of tests was carried out to determine the stability of the class of compounds of the present invention after standing for 6 weeks. The Ross-Miles Foam Tower test was carried out in the above manner and the results recorded in table III.
EXAMPLE 4 The following example illustrates the effectiveness of the surfactants in water of various hardnesses. The Ross Miles Foam Tower test was conducted in the manner of Example 2 using a solution prepared from 27 ml. of an aqueous 5% hypochlorite solution containing 0.2% by weight of sodium pentadecyldiphenyl oxide disulfonate and 973 ml. of water of various hardnesses. The results of such tests are indicated in Table IV.
It is to be understood that bleaching agents other than sodium hypochlorite can beenhanced in the foregoing manner. Some of such agents are the hypochlorites, i.e., sodium, potassium, calcium or magnesium hypochlorite, as well as chloride of lime (CaCl-Ca(ClO)).
We claim:
1. An aqueous 5 percent by weight sodium hypochlorite bleaching solution containing from about 1 to 100% by weight based on the active bleaching agent of a compound selected from the group consisting of alkali metal salts of an alkylated diphenyl oxide sulfonic acid and their nuclearly mono and dichlorinated derivatives having from 8 to 22 carbon atoms in the alkyl moiety and an average of from 1.8 to 2.3 sulfonate moieties per diphenyl oxide moiety.
2. An aqueous 5 percent by weight sodium hypochlorite bleaching solution containing from 1 to 100% by weight based on the active bleaching agent of a sodium dodecyl diphenyl oxide sulfonate having an average of about 2 sulfonate radicals per diphenyl oxide moiety.
References Cited in the file of this patent,
UNITED STATES PATENTS 2,415,657 Riggs et a1. Feb. 11, 1947 2,854,477 Steinhauer Sept. 30, 1958 2,992,999 Smith et al. July 18, 1961
Claims (1)
1. AN AQUEOUS 5 PERCENT BY WEIGHT SODIUM HYPOCHLORITE BLEACHING SOLUTION CONTAINING FROM ABOUT 1 TO 100% BY WEIGHT BASED ON THE ACTIVE BLEACHING AGENT OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF ALKALI METAL SALTS OF AN ALKYLATED DIPHENYL OXIDE SULFONIC ACID AND THEIR NUCLEARLY MONO AND DICHLORINATED DERIVATIVES HAVING FROM 8 TO 22 CARBON ATOMS IN THE ALKYL MOIETY AND AN AVERAGE OF FROM 1.8 TO 2.3 SULFONATE MOIETIES PER DIPHENYL OXIDE MOIETY.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3172861A true US3172861A (en) | 1965-03-09 |
Family
ID=3457208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US3172861D Expired - Lifetime US3172861A (en) | Hypochlorite bleaching compositions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3172861A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2042037A1 (en) * | 1969-08-29 | 1971-03-04 | Unilever Nv | Bleach |
| US4071463A (en) * | 1975-09-11 | 1978-01-31 | The Dow Chemical Company | Stable cleaning agents of hypochlorite bleach and detergent |
| US4235732A (en) * | 1978-02-08 | 1980-11-25 | The Procter & Gamble Company | Liquid bleaching compositions |
| US4390448A (en) * | 1981-10-22 | 1983-06-28 | International Flavors & Fragrances Inc. | Perfumed stable aqueous hypochlorite bleach compositions containing 2-methyl-2-octanol and thickened variation thereof |
| US4444563A (en) * | 1981-09-07 | 1984-04-24 | Ciba-Geigy Corporation | Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials |
| US4627936A (en) * | 1984-10-05 | 1986-12-09 | Gould Paper Corp. | Towel premoistened with antistatic solution for cleaning cathode-ray tubes and the like |
| US4661279A (en) * | 1985-11-22 | 1987-04-28 | Basf Corporation | Detergent composition |
| US4772414A (en) * | 1986-07-24 | 1988-09-20 | Ppg Industries, Inc. | Bleaching composition |
| US4878951A (en) * | 1989-01-17 | 1989-11-07 | A & L Laboratories, Inc. | Low-foaming alkaline, hypochlorite cleaner |
| US5885954A (en) * | 1997-09-22 | 1999-03-23 | Tpc Enterprise, Inc. | Stain remover for textured walls and ceilings |
| US6756352B2 (en) * | 2002-04-01 | 2004-06-29 | Fiber Engineering, Inc. | Removing stubborn mildew stain |
| US20110180619A1 (en) * | 2010-01-25 | 2011-07-28 | The Dial Corporation | Foaming hypochlorite cleaning system |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415657A (en) * | 1942-11-04 | 1947-02-11 | Pennsylvania Salt Mfg Co | Stable hypochlorite composition |
| US2854477A (en) * | 1956-11-20 | 1958-09-30 | Dow Chemical Co | Method of making alkyl diphenyl ether sulfonates |
| US2992999A (en) * | 1958-06-23 | 1961-07-18 | Dow Chemical Co | Dry cleaning solvent containing haloalkyldiphenyl oxide sulfonates |
-
0
- US US3172861D patent/US3172861A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415657A (en) * | 1942-11-04 | 1947-02-11 | Pennsylvania Salt Mfg Co | Stable hypochlorite composition |
| US2854477A (en) * | 1956-11-20 | 1958-09-30 | Dow Chemical Co | Method of making alkyl diphenyl ether sulfonates |
| US2992999A (en) * | 1958-06-23 | 1961-07-18 | Dow Chemical Co | Dry cleaning solvent containing haloalkyldiphenyl oxide sulfonates |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2042037A1 (en) * | 1969-08-29 | 1971-03-04 | Unilever Nv | Bleach |
| US4071463A (en) * | 1975-09-11 | 1978-01-31 | The Dow Chemical Company | Stable cleaning agents of hypochlorite bleach and detergent |
| US4235732A (en) * | 1978-02-08 | 1980-11-25 | The Procter & Gamble Company | Liquid bleaching compositions |
| US4444563A (en) * | 1981-09-07 | 1984-04-24 | Ciba-Geigy Corporation | Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials |
| US4390448A (en) * | 1981-10-22 | 1983-06-28 | International Flavors & Fragrances Inc. | Perfumed stable aqueous hypochlorite bleach compositions containing 2-methyl-2-octanol and thickened variation thereof |
| US4627936A (en) * | 1984-10-05 | 1986-12-09 | Gould Paper Corp. | Towel premoistened with antistatic solution for cleaning cathode-ray tubes and the like |
| US4661279A (en) * | 1985-11-22 | 1987-04-28 | Basf Corporation | Detergent composition |
| US4772414A (en) * | 1986-07-24 | 1988-09-20 | Ppg Industries, Inc. | Bleaching composition |
| US4878951A (en) * | 1989-01-17 | 1989-11-07 | A & L Laboratories, Inc. | Low-foaming alkaline, hypochlorite cleaner |
| US5885954A (en) * | 1997-09-22 | 1999-03-23 | Tpc Enterprise, Inc. | Stain remover for textured walls and ceilings |
| US6756352B2 (en) * | 2002-04-01 | 2004-06-29 | Fiber Engineering, Inc. | Removing stubborn mildew stain |
| US20110180619A1 (en) * | 2010-01-25 | 2011-07-28 | The Dial Corporation | Foaming hypochlorite cleaning system |
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