US3340309A - Biodegradable, liquid, water-miscible alkylene oxide condensation products - Google Patents
Biodegradable, liquid, water-miscible alkylene oxide condensation products Download PDFInfo
- Publication number
- US3340309A US3340309A US467760A US46776065A US3340309A US 3340309 A US3340309 A US 3340309A US 467760 A US467760 A US 467760A US 46776065 A US46776065 A US 46776065A US 3340309 A US3340309 A US 3340309A
- Authority
- US
- United States
- Prior art keywords
- mixture
- alcohol
- carbon atoms
- weight percent
- compounds
- 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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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
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
Definitions
- This invention relates to rinse additives for automatic dishwashing machines. More particularly, this invention relates to biodegradable, liquid, water-miscible alkylene oxide condensation products which are particularly useful as rinse additives for automatic dishwashing machines.
- R is a straight chain alkyl group having from 8 to 20 carbon atoms
- a has an average value of from 3.75 to 12.75
- b has an average value of from 1.7 to 7.0, the ratio of a tob being from 1.8:1 to 22:1, from O to 10 weight percent of said compounds in said mixture having an R containing 8 carbon atoms, from O to 50 weight percent of said compounds in said mixture having an R containing 10 carbon atoms, from 0 to 95 weight percent of said compounds in said mixture having an R containing 12 carbon atoms, from 0 to 95 weight percent of said compounds in said mixture having an R containing 14 carbon atoms, from 0 to 95 weight percent of said compounds in said mixture having an R containing 16 ice carbon atoms, from O to 50 weight percent of said compounds in said mixture having an R containing 18 carbon atoms, and from 0 to 10 weight percent of said compounds in said mixture having an R containing 20 carbon atoms, the above weight percents based on a total of weight percent.
- the third component employed in the preparation of the products of this invention is propylene oxide.
- the amount of propylene oxide is extremely critical. From about 1.70 to 7.0 moles of propylene oxide per mole of alcohol mixture is required to prepare the products of this invention. If less than 1.70 moles of propylene oxide is employed, the resulting product is too hydrophilic and generates too much foam to be an effective rinse additive, whereas if more than 7.0 moles of propylene oxide is employed the resulting product is too hydrophobic and leaves an oily film on the washed items.
- ethylene oxide to propylene oxide ratio be maintained between 1.8:1 to 2.211. It has been determined that products prepared with ratios less than 1.821, when subsequently employed as rinse additives, are ineffective in preventing streaking and filming of the items washed. Likewise, at ratios greater than 2.2:1, the products prepared are ineffective in preventing water spotting, especially on glasses and utensils.
- a Hotpoint dishwasher was loaded with five glasses, three four-inch and three six-inch Melmac plates in the Parts 7 top rack and six nine-inch chinaware plates in the bottom rack, all evenly distributed. Six knives, six forks, and six teaspoons were placed in the metal holder on the lower rack. Prior to the first wash, the dishwasher was allowed to run one or two cycles, without drying, to get the machine up to temperature. The dishwasher contained no soil, detergent, rinse air or glass during this warm-up period. The test was carried out with deionized water at 135 +5 F., although a higher temperature or hard water can be used. Fifty parts of soil was weighed out on a five-inch watch glass. Two ten-part portions of standard detergent powder were weighed out into 50 milliliter beakers. On a three-inch watch glass was weighed out 0.8 part of the candidate rinse additive.
- Examples XII and XIII demonstrate the criticality of the amounts of ethylene oxide and propylene oxide.
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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)
- Biological Depolymerization Polymers (AREA)
- Fats And Perfumes (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL134504D NL134504C (es) | 1965-06-28 | ||
US467760A US3340309A (en) | 1965-06-28 | 1965-06-28 | Biodegradable, liquid, water-miscible alkylene oxide condensation products |
NL6608854A NL6608854A (es) | 1965-06-28 | 1966-06-24 | |
DE19661593043 DE1593043A1 (de) | 1965-06-28 | 1966-06-25 | Verfahren zur Herstellung von biologisch abbaufaehigen fuessigen Spuelzusaetzen fuer Geschirrspuelautomaten |
GB28813/66A GB1131333A (en) | 1965-06-28 | 1966-06-27 | Biodegradable, liquid, water-miscible alkylene oxide condensation products |
BE683227D BE683227A (es) | 1965-06-28 | 1966-06-27 | |
FR67088A FR1484951A (fr) | 1965-06-28 | 1966-06-27 | Produits de condensation d'oxyde d'alcoylène liquides, miscibles à l'eau et biodégradables |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US467760A US3340309A (en) | 1965-06-28 | 1965-06-28 | Biodegradable, liquid, water-miscible alkylene oxide condensation products |
Publications (1)
Publication Number | Publication Date |
---|---|
US3340309A true US3340309A (en) | 1967-09-05 |
Family
ID=23857062
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US467760A Expired - Lifetime US3340309A (en) | 1965-06-28 | 1965-06-28 | Biodegradable, liquid, water-miscible alkylene oxide condensation products |
Country Status (5)
Country | Link |
---|---|
US (1) | US3340309A (es) |
BE (1) | BE683227A (es) |
DE (1) | DE1593043A1 (es) |
GB (1) | GB1131333A (es) |
NL (2) | NL6608854A (es) |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3504041A (en) * | 1966-02-14 | 1970-03-31 | Wyandotte Chemicals Corp | Nonionic condensation products having enhanced activity |
US3539519A (en) * | 1968-02-23 | 1970-11-10 | Continental Oil Co | Low foaming nonionic detergents |
US3625901A (en) * | 1969-12-02 | 1971-12-07 | Economics Lab | Surface active dishwashing rinse aids |
US3862243A (en) * | 1972-02-17 | 1975-01-21 | Int Flavors & Fragrances Inc | Mixed oxyalkylates employed as antifoamers |
US4070298A (en) * | 1976-07-26 | 1978-01-24 | Olin Corporation | Defoaming detergent additive |
US4115457A (en) * | 1976-07-07 | 1978-09-19 | Sandoz Ltd. | Polyglycol ether derivatives |
US4134854A (en) * | 1973-05-05 | 1979-01-16 | Texaco Development Corp. | Nonionic surfactant with low pour point |
US4179544A (en) * | 1977-12-05 | 1979-12-18 | Basf Wyandotte Corporation | Fiber finish compositions |
US4280919A (en) * | 1979-05-10 | 1981-07-28 | Basf Aktiengesellschaft | Detergents and cleansers containing oxyalkylated alcohols as biodegradable, low-foam surfactants |
US4302349A (en) * | 1979-06-26 | 1981-11-24 | Chemische Werke Huls, A.G. | Adducts of alcohols and olefin oxides, suitable for reducing the interfacial surface tension of oily phases with respect to water |
US4303544A (en) * | 1979-05-04 | 1981-12-01 | Chemische Werke Huels, A.G. | Adducts of alcohols and olefin oxides as biodegradable and low-foaming tensides useful in detergents |
US4361035A (en) * | 1979-08-15 | 1982-11-30 | Rockwell International Corporation | Nonstaining leak tracer solution and method employing same |
US4469606A (en) * | 1982-07-26 | 1984-09-04 | Ciba-Geigy Corporation | Stabilization systems for fiber finishes |
US4518459A (en) * | 1979-11-13 | 1985-05-21 | Economics Laboratory, Inc. | Methods of deinking secondary fibers |
US4545917A (en) * | 1984-02-09 | 1985-10-08 | Creative Products Resource Associates Ltd. | Automatic dishwasher product in solid form |
US4647314A (en) * | 1985-03-05 | 1987-03-03 | Drew Chemical Corporation | Rinse water additive |
EP0423230A1 (en) * | 1988-07-05 | 1991-04-24 | Olin Corp | ANIONIC SURFACTANTS RESULTING FROM AN ADDITION REACTION BETWEEN MALEIC OR FUMARIC ACID AND A POLY (ETHOXYL) ALCOHOL. |
US5151093A (en) * | 1990-10-29 | 1992-09-29 | Alza Corporation | Osmotically driven syringe with programmable agent delivery |
WO1994011330A1 (en) * | 1992-11-19 | 1994-05-26 | Berol Nobel Ab | Alkoxylate of 2-propyl heptanol and use thereof |
US5417808A (en) * | 1991-08-30 | 1995-05-23 | Lion Corporation | Deinking composition for flotation and deinking method |
US5464562A (en) * | 1995-04-24 | 1995-11-07 | Basf Corporation | Polyoxyalkylene polyether monool polyurethane foam additive |
US5540665A (en) * | 1994-01-31 | 1996-07-30 | Alza Corporation | Gas driven dispensing device and gas generating engine therefor |
US6242389B1 (en) * | 1997-04-14 | 2001-06-05 | Bp Chemicals Limited | Ethers |
CN102094321A (zh) * | 2009-12-08 | 2011-06-15 | 花王株式会社 | 对棉布赋予水扩散促进功能的棉布处理方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4668423A (en) * | 1985-04-19 | 1987-05-26 | Sherex Chemical Company | Liquid biodegradable surfactant and use thereof |
DE4421576A1 (de) * | 1994-06-21 | 1996-01-04 | Hoechst Ag | Alkoxylierungsprodukt-Mischungen mit enger Alkoxylverteilung |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3030426A (en) * | 1957-12-23 | 1962-04-17 | Shell Oil Co | Low ash polyoxyalkylene compounds and their preparation |
GB950844A (en) * | 1959-07-31 | 1964-02-26 | Boehme Fettchemie Gmbh | Alkylene oxide addition products |
-
0
- NL NL134504D patent/NL134504C/xx active
-
1965
- 1965-06-28 US US467760A patent/US3340309A/en not_active Expired - Lifetime
-
1966
- 1966-06-24 NL NL6608854A patent/NL6608854A/xx unknown
- 1966-06-25 DE DE19661593043 patent/DE1593043A1/de active Pending
- 1966-06-27 GB GB28813/66A patent/GB1131333A/en not_active Expired
- 1966-06-27 BE BE683227D patent/BE683227A/xx not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3030426A (en) * | 1957-12-23 | 1962-04-17 | Shell Oil Co | Low ash polyoxyalkylene compounds and their preparation |
GB950844A (en) * | 1959-07-31 | 1964-02-26 | Boehme Fettchemie Gmbh | Alkylene oxide addition products |
Cited By (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3504041A (en) * | 1966-02-14 | 1970-03-31 | Wyandotte Chemicals Corp | Nonionic condensation products having enhanced activity |
US3539519A (en) * | 1968-02-23 | 1970-11-10 | Continental Oil Co | Low foaming nonionic detergents |
US3625901A (en) * | 1969-12-02 | 1971-12-07 | Economics Lab | Surface active dishwashing rinse aids |
US3862243A (en) * | 1972-02-17 | 1975-01-21 | Int Flavors & Fragrances Inc | Mixed oxyalkylates employed as antifoamers |
US4134854A (en) * | 1973-05-05 | 1979-01-16 | Texaco Development Corp. | Nonionic surfactant with low pour point |
US4115457A (en) * | 1976-07-07 | 1978-09-19 | Sandoz Ltd. | Polyglycol ether derivatives |
US4070298A (en) * | 1976-07-26 | 1978-01-24 | Olin Corporation | Defoaming detergent additive |
US4179544A (en) * | 1977-12-05 | 1979-12-18 | Basf Wyandotte Corporation | Fiber finish compositions |
US4303544A (en) * | 1979-05-04 | 1981-12-01 | Chemische Werke Huels, A.G. | Adducts of alcohols and olefin oxides as biodegradable and low-foaming tensides useful in detergents |
US4280919A (en) * | 1979-05-10 | 1981-07-28 | Basf Aktiengesellschaft | Detergents and cleansers containing oxyalkylated alcohols as biodegradable, low-foam surfactants |
US4302349A (en) * | 1979-06-26 | 1981-11-24 | Chemische Werke Huls, A.G. | Adducts of alcohols and olefin oxides, suitable for reducing the interfacial surface tension of oily phases with respect to water |
US4361035A (en) * | 1979-08-15 | 1982-11-30 | Rockwell International Corporation | Nonstaining leak tracer solution and method employing same |
US4518459A (en) * | 1979-11-13 | 1985-05-21 | Economics Laboratory, Inc. | Methods of deinking secondary fibers |
US4469606A (en) * | 1982-07-26 | 1984-09-04 | Ciba-Geigy Corporation | Stabilization systems for fiber finishes |
US4545917A (en) * | 1984-02-09 | 1985-10-08 | Creative Products Resource Associates Ltd. | Automatic dishwasher product in solid form |
US4647314A (en) * | 1985-03-05 | 1987-03-03 | Drew Chemical Corporation | Rinse water additive |
EP0423230A1 (en) * | 1988-07-05 | 1991-04-24 | Olin Corp | ANIONIC SURFACTANTS RESULTING FROM AN ADDITION REACTION BETWEEN MALEIC OR FUMARIC ACID AND A POLY (ETHOXYL) ALCOHOL. |
EP0423230A4 (en) * | 1988-07-05 | 1991-07-24 | Olin Corporation | Anionic surfactant addition products of maleic or fumaric acid and a poly(ethoxylated) alcohol |
US5151093A (en) * | 1990-10-29 | 1992-09-29 | Alza Corporation | Osmotically driven syringe with programmable agent delivery |
US5312389A (en) * | 1990-10-29 | 1994-05-17 | Felix Theeuwes | Osmotically driven syringe with programmable agent delivery |
US5417808A (en) * | 1991-08-30 | 1995-05-23 | Lion Corporation | Deinking composition for flotation and deinking method |
EP0669907B1 (en) * | 1992-11-19 | 1997-05-21 | Berol Nobel AB | Use of alkoxylate of 2-propyl heptanol |
US5608118A (en) * | 1992-11-19 | 1997-03-04 | Berol Nobel Ab | Alkoxylate of 2-propyl heptanol and detergent containing same |
WO1994011330A1 (en) * | 1992-11-19 | 1994-05-26 | Berol Nobel Ab | Alkoxylate of 2-propyl heptanol and use thereof |
US5661121A (en) * | 1992-11-19 | 1997-08-26 | Berol Nobel Ab | 2-propyl heptanol alkoxylates and process of cleaning hard surfaces therewith |
US5540665A (en) * | 1994-01-31 | 1996-07-30 | Alza Corporation | Gas driven dispensing device and gas generating engine therefor |
US5464562A (en) * | 1995-04-24 | 1995-11-07 | Basf Corporation | Polyoxyalkylene polyether monool polyurethane foam additive |
US5484817A (en) * | 1995-04-24 | 1996-01-16 | Basf Corporation | Polyoxyalkylene polyether monool polyurethane foam additive |
US5488071A (en) * | 1995-04-24 | 1996-01-30 | Basf Corporation | Polyoxyalkylene polyether monool polyurethane foam additive |
US6242389B1 (en) * | 1997-04-14 | 2001-06-05 | Bp Chemicals Limited | Ethers |
CN102094321A (zh) * | 2009-12-08 | 2011-06-15 | 花王株式会社 | 对棉布赋予水扩散促进功能的棉布处理方法 |
Also Published As
Publication number | Publication date |
---|---|
DE1593043A1 (de) | 1970-07-23 |
GB1131333A (en) | 1968-10-23 |
NL134504C (es) | |
NL6608854A (es) | 1966-12-29 |
BE683227A (es) | 1966-12-01 |
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