US2073464A - Detergent - Google Patents
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- US2073464A US2073464A US2073464DA US2073464A US 2073464 A US2073464 A US 2073464A US 2073464D A US2073464D A US 2073464DA US 2073464 A US2073464 A US 2073464A
- Authority
- US
- United States
- Prior art keywords
- terpineol
- ingredients
- water
- detergent
- amount
- 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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- 239000003599 detergent Substances 0.000 title description 26
- 239000000203 mixture Substances 0.000 description 56
- 239000004615 ingredient Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- WUOACPNHFRMFPN-UHFFFAOYSA-N Terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 30
- 229940116411 Terpineol Drugs 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- -1 penetrant Substances 0.000 description 22
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 20
- 230000000149 penetrating Effects 0.000 description 20
- 238000009736 wetting Methods 0.000 description 20
- 239000000344 soap Substances 0.000 description 18
- 239000010665 pine oil Substances 0.000 description 16
- 235000007586 terpenes Nutrition 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 239000000194 fatty acid Substances 0.000 description 14
- 150000004665 fatty acids Chemical class 0.000 description 14
- WUOACPNHFRMFPN-VIFPVBQESA-N (R)-(+)-α-terpineol Chemical compound CC1=CC[C@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-VIFPVBQESA-N 0.000 description 12
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 12
- WUOACPNHFRMFPN-SECBINFHSA-N alpha-Terpineol Natural products CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 12
- 229940088601 alpha-terpineol Drugs 0.000 description 12
- 238000009991 scouring Methods 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000003509 tertiary alcohols Chemical class 0.000 description 12
- 239000004753 textile Substances 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 239000003995 emulsifying agent Substances 0.000 description 10
- 239000005642 Oleic acid Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 4
- 235000011613 Pinus brutia Nutrition 0.000 description 4
- 241000018646 Pinus brutia Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 150000002194 fatty esters Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000008149 soap solution Substances 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical class CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 4
- 150000003505 terpenes Chemical class 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- RUJPNZNXGCHGID-UHFFFAOYSA-N (Z)-beta-Terpineol Natural products CC(=C)C1CCC(C)(O)CC1 RUJPNZNXGCHGID-UHFFFAOYSA-N 0.000 description 2
- 239000001074 1-methoxy-4-[(E)-prop-1-enyl]benzene Substances 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N Anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- QJVXKWHHAMZTBY-GCPOEHJPSA-N Syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 2
- 101700065062 andA Proteins 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000001804 emulsifying Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 150000002193 fatty amides Chemical class 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- NNRLDGQZIVUQTE-UHFFFAOYSA-N γ-Terpineol Chemical compound CC(C)=C1CCC(C)(O)CC1 NNRLDGQZIVUQTE-UHFFFAOYSA-N 0.000 description 2
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
-
- 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
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
Definitions
- This invention relates to Van improved detergent, penetrant, and wetting agent for use in. the wet-scouring processes of the textile and laundry industries.
- pine oil has detergent, penetrant, and wetting properties, and it has been used as such in the textile and laundry industries in conjunction with an emulsifying agent such as a soap.
- pineoil has not proved entirely satisfactory for use in scouring in the textile industry due to the fact that when it is used under the high temperature conditions customary in scouring textiles, a penetrating pine odor is given off, which is obnoxious to some persons; and due to the fact that in many instancesmaterial scoured with use of pine oil carries the odor thereof.
- pine wood for example, by the steam distillation of pine wood, or a mixture Aof terpineols, provides an excellent detergent, penetrant and wettingr agent for use in the wet-scouring' of textiles, either alone 5 or Where dissolved or emulsied in water through the medium of an emulsifying agent, and one free from the objections heretofore noted with reference to pine oil.
- Alpha-terpineol has a pleasant higher initial boiling point than pine oil. Also, it is more readily dissolved or emulsed in water than is pine oil and does not produce any objectionable odor under high temperature conditions, nor leave any objectionable odor traceable to it in scoured material.
- inventions may be pure alpha-terpineol, or it may be of the commercial grade comprising a mixture of terpineols, such, for example, as is obtained by fractionation of pine oil.
- terpineols such as beta-terpineol, gamma-terpineol, and traces of anethol and terpene hydrocarbons.
- the terpneol will desirably contain not less than about 90% tertiary terpene alcohols.
- compositions in accordance with this invention may contain pure alpha-terpineol or commercial terpineol in amount within about the range 50%-?0% and water, containing an emulsifying agent, as a fatty acid soap, in suitable amount, in amount within about the range 50%10%.
- an emulsifying agent as a fatty acid soap
- the various ingredients should be present in such relative -proportions as to be completely miscible, or as to form a clear solution,
- the terpineol for use in accordance ⁇ with this ⁇ which when added to water or to a water-soap solution, will immediately emulsify and form an emulsion of such stability that it will not break in the wet-scouring of textiles.
- any fatty acid soap or equivalent thereof as, for example, sodium or potassium oleates, stearates, etc., etc., ethanolamine oleates, stearates, etc., etc., may be used, it being understood that potassium, sodium and ethanolamine soaps will be equivalents. It will also be understood that the soap may be produced in the production of the compositions by utilizing a fatty acid and an alkali as ingredients.
- the sulfonic acidsof fatty esters or acids, or their alkali metal salts In place of a fatty acid soap, the sulfonic acidsof fatty esters or acids, or their alkali metal salts; the acid sulfuric ester of fatty esters, fatty alcohols, or hydroxy fatty acids, or their alkali metal salts; the sulfonic acids of fatty amides, or
- compositions in accordance with this invention may be determined for any given emulsifying agent as follows, with reference to the accompanying drawing inwhich'the single iigure is a graph with reference to the use of sodium oleate by way of example:
- a satisfactory composition in accordance w'th this Vinvention may be made up with terpineol not less than about 50%, sodium oleate not in excess of about 37%, and water not in excess of about 40% the ingredients being relatively proportioned to form a clear solution.
- compositions may be made up on the following formulae:
- a satisfactory composition in accordance with this in vention, may be produced by mixing 14.0 parts of oleic acid with 70. parts of terpineol, and then adding a solution of 1.88 parts of sodium hydroxide in 14.12 parts of water and agitating until the alkali solution is dispersed throughout the terpineol solution and has reacted with the oleic acid. The action will be complete when the emulsion of alkali solution in the alpha-terpineololeic acid solution becomes clear. Heating above ordinary temperatures will be unnecessary.
- the above composition may be prepared by dissolving 1.88 parts of sodium hydroxide in 14.12 parts of water, adding '70 parts of terpineol, and while agitating, adding 14.0 parts of oleic acid, continuing the agitation until the mix clears.
- the above composition may be prepared by mixing with 'l0 parts of terpineol, a sodium oleate soap solution consisting of 15 parts of sodium oleate and 15 parts of water, agitating until the mix clears.
- composition may be prepared in any suitable form of apparatus, as, for example, a vessel provided with a stirring device.
- composition in accordance with this invention in wet-scouring processes, the composition will be added to water or to a watersoap mixture or solution in desired quantity and will promptly emulsify therein and form a substantially stable emulsion.
- the terpineol of the composition will then act in the process as an effective detergent. penetrant and wetting agent.
- a detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than 90% tertiary alcohols and containing no more than traces of any terpene hydrocarbon, in amount not substantially less than 50% of the composition, a fatty acid soap and water, the ingredients being relatively proportioned so as to give a clear solution.
- a detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than 90% tertiary -alcohols and containing no more than traces of any terpene hydrocarbon, in'amount within about the range 50-90%, and an aqueous solution of a fatty acid soap in amount within about the range 50-10%, the ingredients being relatively proportioned so as to give a clear solution.
- a detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than 90% tertiary alcohols and containing no more than traces of any terpene.
- hydrocarbon in amount not substantially less than 50%, sodium oleate in amount not substantially in excess of 37% and water in amount not substantially in excess of 40%, the ingredients being relatively proportioned so as to give a clear solution.
- a detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than 90% tertiary alcohols and containing no more than traces of any terpene hydrocarbon, about sodium oleate about 25% and water about 15%.
- a detergent, penetrating andA wetting composition including as ingredients terpineol, comprising not less than 90% tertiary alcohols and containing no more thanA traces ,of any terpene hydocarbon, about sodium oleate about 15% and watenabout 15%.
- a detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than tertiary alcohols and containing no more than traces of any terpene hydrocarbon, 'about 80%, sodium oleate about 10% and ⁇ water about 10%.
- a detergent, penetrating and wetting composition including as ingredients substantially pure alpha-terpineol in amount not substantially less than 50% of the composition, a soap and water, the ingredients being relatively proportioned so as to give a clear solution.
- a detergent, penetrating and wetting composition including as ingredients substantially pure alpha-terpineol in amount not substantially less than 50%, sodium oleate in amount not substantially in excess of 37%. and water in amount not substantially in excess of 40%, the ingredients being relatively proportioned so as to give a clear solution.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Description
Patented Mar. 9, 1937 UNITED j STATES PATENT OFFICE DETEBGENT, PENETRATING, AND WETTING COM10SITION Wheeler Ylhllavey, State College, Pa.,
Hercules Powder Company, Wilmin assignor to gton, Del.,
'somma This invention relates to Van improved detergent, penetrant, and wetting agent for use in. the wet-scouring processes of the textile and laundry industries.
5 Heretofore it has been known that pine oil has detergent, penetrant, and wetting properties, and it has been used as such in the textile and laundry industries in conjunction with an emulsifying agent such as a soap. However, pineoil has not proved entirely satisfactory for use in scouring in the textile industry due to the fact that when it is used under the high temperature conditions customary in scouring textiles, a penetrating pine odor is given off, which is obnoxious to some persons; and due to the fact that in many instancesmaterial scoured with use of pine oil carries the odor thereof.
Now, in accordance with this invention it has been found that a terpineolm, such as, for example,
2o alpha-terpineol, a constituent of pine oil obtained,
. for example, by the steam distillation of pine wood, or a mixture Aof terpineols, provides an excellent detergent, penetrant and wettingr agent for use in the wet-scouring' of textiles, either alone 5 or Where dissolved or emulsied in water through the medium of an emulsifying agent, and one free from the objections heretofore noted with reference to pine oil.
Alpha-terpineol has a pleasant higher initial boiling point than pine oil. Also, it is more readily dissolved or emulsed in water than is pine oil and does not produce any objectionable odor under high temperature conditions, nor leave any objectionable odor traceable to it in scoured material.
invention may be pure alpha-terpineol, or it may be of the commercial grade comprising a mixture of terpineols, such, for example, as is obtained by fractionation of pine oil. The presence of small amounts of impurities such as beta-terpineol, gamma-terpineol, and traces of anethol and terpene hydrocarbons, will not be objectionable. However, the terpneol will desirably contain not less than about 90% tertiary terpene alcohols.
Generally speaking, compositions in accordance with this invention may contain pure alpha-terpineol or commercial terpineol in amount within about the range 50%-?0% and water, containing an emulsifying agent, as a fatty acid soap, in suitable amount, in amount within about the range 50%10%. The various ingredients should be present in such relative -proportions as to be completely miscible, or as to form a clear solution,
odor and a' gels, and the points y, h,
The terpineol for use in accordance `with this` which when added to water or to a water-soap solution, will immediately emulsify and form an emulsion of such stability that it will not break in the wet-scouring of textiles.
In preparing compositions in acordance with 5 this invention any fatty acid soap or equivalent thereof, as, for example, sodium or potassium oleates, stearates, etc., etc., ethanolamine oleates, stearates, etc., etc., may be used, it being understood that potassium, sodium and ethanolamine soaps will be equivalents. It will also be understood that the soap may be produced in the production of the compositions by utilizing a fatty acid and an alkali as ingredients.
In place of a fatty acid soap, the sulfonic acidsof fatty esters or acids, or their alkali metal salts; the acid sulfuric ester of fatty esters, fatty alcohols, or hydroxy fatty acids, or their alkali metal salts; the sulfonic acids of fatty amides, or
their alkali metal salts, ing agents. Y
The relative proportions of the components, i. e. terpineol, emulsifying agent and water, for the production of compositions in accordance with this invention may be determined for any given emulsifying agent as follows, with reference to the accompanying drawing inwhich'the single iigure is a graph with reference to the use of sodium oleate by way of example:
In the drawing the lines L, L', derived from reference to points a, b, c, d, indicating proportions of ingredients providing clear solutions at ordinary temperatures, the points e, f, providing' providing opaque emula sions, define the ranges of proportions of ingredients with which clear solutions will be formed using sodium oleate.
l When a diierent emulsifying similar though not identical ranges may determined by those skilled in the art.
As illustrative, for example, a satisfactory composition in accordance w'th this Vinvention may be made up with terpineol not less than about 50%, sodium oleate not in excess of about 37%, and water not in excess of about 40% the ingredients being relatively proportioned to form a clear solution.
More specifically, satisfactory compositions may be made up on the following formulae:
may be used as emulsifyagent is used, be readily As further illustrative, for example, a satisfactory composition, in accordance with this in vention, may be produced by mixing 14.0 parts of oleic acid with 70. parts of terpineol, and then adding a solution of 1.88 parts of sodium hydroxide in 14.12 parts of water and agitating until the alkali solution is dispersed throughout the terpineol solution and has reacted with the oleic acid. The action will be complete when the emulsion of alkali solution in the alpha-terpineololeic acid solution becomes clear. Heating above ordinary temperatures will be unnecessary. Alternatively, the above composition may be prepared by dissolving 1.88 parts of sodium hydroxide in 14.12 parts of water, adding '70 parts of terpineol, and while agitating, adding 14.0 parts of oleic acid, continuing the agitation until the mix clears. Again, the above composition may be prepared by mixing with 'l0 parts of terpineol, a sodium oleate soap solution consisting of 15 parts of sodium oleate and 15 parts of water, agitating until the mix clears.
As will be appreciated, the composition may be prepared in any suitable form of apparatus, as, for example, a vessel provided with a stirring device.
In the use of a composition in accordance with this invention in wet-scouring processes, the composition will be added to water or to a watersoap mixture or solution in desired quantity and will promptly emulsify therein and form a substantially stable emulsion.
The terpineol of the composition will then act in the process as an effective detergent. penetrant and wetting agent.
It will be understood that it is not contemplated that this invention shall be limited to the details given herein for full disclosure and exemplication of this invention.
What I claim and desire to protect by Letters Patent is:
1. A detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than 90% tertiary alcohols and containing no more than traces of any terpene hydrocarbon, in amount not substantially less than 50% of the composition, a fatty acid soap and water, the ingredients being relatively proportioned so as to give a clear solution.
2. A detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than 90% tertiary -alcohols and containing no more than traces of any terpene hydrocarbon, in'amount within about the range 50-90%, and an aqueous solution of a fatty acid soap in amount within about the range 50-10%, the ingredients being relatively proportioned so as to give a clear solution.
3. A detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than 90% tertiary alcohols and containing no more than traces of any terpene.
hydrocarbon, in amount not substantially less than 50%, sodium oleate in amount not substantially in excess of 37% and water in amount not substantially in excess of 40%, the ingredients being relatively proportioned so as to give a clear solution.
4. A detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than 90% tertiary alcohols and containing no more than traces of any terpene hydrocarbon, about sodium oleate about 25% and water about 15%.
5. A detergent, penetrating andA wetting composition including as ingredients terpineol, comprising not less than 90% tertiary alcohols and containing no more thanA traces ,of any terpene hydocarbon, about sodium oleate about 15% and watenabout 15%.
6. A detergent, penetrating and wetting composition including as ingredients terpineol, comprising not less than tertiary alcohols and containing no more than traces of any terpene hydrocarbon, 'about 80%, sodium oleate about 10% and` water about 10%.
7. A detergent, penetrating and wetting composition including as ingredients substantially pure alpha-terpineol in amount not substantially less than 50% of the composition, a soap and water, the ingredients being relatively proportioned so as to give a clear solution.
8. A detergent, penetrating and wetting composition including as ingredients substantially pure alpha-terpineol in amount not substantially less than 50%, sodium oleate in amount not substantially in excess of 37%. and water in amount not substantially in excess of 40%, the ingredients being relatively proportioned so as to give a clear solution.
WHEELER P. DAVEY.
Publications (1)
Publication Number | Publication Date |
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US2073464A true US2073464A (en) | 1937-03-09 |
Family
ID=3428555
Family Applications (1)
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US2073464D Expired - Lifetime US2073464A (en) | Detergent |
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US (1) | US2073464A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3360471A (en) * | 1963-04-18 | 1967-12-26 | Sterling Drug Inc | Biodegradable cleaning compound |
US3900407A (en) * | 1972-12-14 | 1975-08-19 | Colgate Palmolive Co | Composition for cleaning and glazing furs |
US4414128A (en) * | 1981-06-08 | 1983-11-08 | The Procter & Gamble Company | Liquid detergent compositions |
US4561991A (en) * | 1984-08-06 | 1985-12-31 | The Procter & Gamble Company | Fabric cleaning compositions for clay-based stains |
US5597792A (en) * | 1993-04-02 | 1997-01-28 | The Dow Chemical Company | High water content, low viscosity, oil continuous microemulsions and emulsions, and their use in cleaning applications |
WO2004001504A1 (en) * | 2002-05-15 | 2003-12-31 | Dianne Iverglynne | A biodegradable developing solution and method of use |
-
0
- US US2073464D patent/US2073464A/en not_active Expired - Lifetime
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3360471A (en) * | 1963-04-18 | 1967-12-26 | Sterling Drug Inc | Biodegradable cleaning compound |
US3900407A (en) * | 1972-12-14 | 1975-08-19 | Colgate Palmolive Co | Composition for cleaning and glazing furs |
US4414128A (en) * | 1981-06-08 | 1983-11-08 | The Procter & Gamble Company | Liquid detergent compositions |
US4561991A (en) * | 1984-08-06 | 1985-12-31 | The Procter & Gamble Company | Fabric cleaning compositions for clay-based stains |
US5597792A (en) * | 1993-04-02 | 1997-01-28 | The Dow Chemical Company | High water content, low viscosity, oil continuous microemulsions and emulsions, and their use in cleaning applications |
US5811383A (en) * | 1993-04-02 | 1998-09-22 | The Dow Chemical Company | High water content, low viscosity, oil continuous microemulsions and emulsions, and their use in cleaning applications |
WO2004001504A1 (en) * | 2002-05-15 | 2003-12-31 | Dianne Iverglynne | A biodegradable developing solution and method of use |
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