US3340309A - Biodegradable, liquid, water-miscible alkylene oxide condensation products - Google Patents

Biodegradable, liquid, water-miscible alkylene oxide condensation products Download PDF

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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
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US
United States
Prior art keywords
mixture
alcohol
carbon atoms
weight percent
compounds
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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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US467760A
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English (en)
Inventor
Eugene A Weipert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyandotte Chemicals Corp
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Wyandotte Chemicals Corp
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Publication date
Priority to NL134504D priority Critical patent/NL134504C/xx
Application filed by Wyandotte Chemicals Corp filed Critical Wyandotte Chemicals Corp
Priority to US467760A priority patent/US3340309A/en
Priority to NL6608854A priority patent/NL6608854A/xx
Priority to DE19661593043 priority patent/DE1593043A1/de
Priority to FR67088A priority patent/FR1484951A/fr
Priority to GB28813/66A priority patent/GB1131333A/en
Priority to BE683227D priority patent/BE683227A/xx
Application granted granted Critical
Publication of US3340309A publication Critical patent/US3340309A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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)
US467760A 1965-06-28 1965-06-28 Biodegradable, liquid, water-miscible alkylene oxide condensation products Expired - Lifetime US3340309A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
NL134504D NL134504C (en)) 1965-06-28
US467760A US3340309A (en) 1965-06-28 1965-06-28 Biodegradable, liquid, water-miscible alkylene oxide condensation products
NL6608854A NL6608854A (en)) 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
FR67088A FR1484951A (fr) 1965-06-28 1966-06-27 Produits de condensation d'oxyde d'alcoylène liquides, miscibles à l'eau et biodégradables
GB28813/66A GB1131333A (en) 1965-06-28 1966-06-27 Biodegradable, liquid, water-miscible alkylene oxide condensation products
BE683227D BE683227A (en)) 1965-06-28 1966-06-27

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

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US467760A Expired - Lifetime US3340309A (en) 1965-06-28 1965-06-28 Biodegradable, liquid, water-miscible alkylene oxide condensation products

Country Status (5)

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US (1) US3340309A (en))
BE (1) BE683227A (en))
DE (1) DE1593043A1 (en))
GB (1) GB1131333A (en))
NL (2) NL6608854A (en))

Cited By (24)

* Cited by examiner, † Cited by third party
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
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
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
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 (30)

* Cited by examiner, † Cited by third party
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
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
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
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
US5540665A (en) * 1994-01-31 1996-07-30 Alza Corporation Gas driven dispensing device and gas generating engine therefor
US5488071A (en) * 1995-04-24 1996-01-30 Basf Corporation Polyoxyalkylene polyether monool polyurethane foam additive
US5484817A (en) * 1995-04-24 1996-01-16 Basf Corporation Polyoxyalkylene polyether monool polyurethane foam additive
US5464562A (en) * 1995-04-24 1995-11-07 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
NL134504C (en))
NL6608854A (en)) 1966-12-29
GB1131333A (en) 1968-10-23
BE683227A (en)) 1966-12-01
DE1593043A1 (de) 1970-07-23

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