EP0004353A2 - Im Wasser kein Gel formendes alkylenoxysubstituiertes Rizinusöl - Google Patents
Im Wasser kein Gel formendes alkylenoxysubstituiertes Rizinusöl Download PDFInfo
- Publication number
- EP0004353A2 EP0004353A2 EP79100801A EP79100801A EP0004353A2 EP 0004353 A2 EP0004353 A2 EP 0004353A2 EP 79100801 A EP79100801 A EP 79100801A EP 79100801 A EP79100801 A EP 79100801A EP 0004353 A2 EP0004353 A2 EP 0004353A2
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- EP
- European Patent Office
- Prior art keywords
- castor oil
- alkyleneoxy
- water
- constituent
- reactor
- 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.)
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
Definitions
- This invention relates to non-water gelling alkyleneoxy substituted castor oil compositions.
- it relates to such alkyleneoxy substituted castor oil compositions wherein said alkyleneoxy moiety contains at least one C 3 or C 4 alkyleneoxy constituent.
- the invention relates to non-water gelling alkyleneoxy substituted castor oil compositions and their use as textile lubricants in textile processing operations.
- Ethoxylated castor oils have heretofore been employed as tufting lubricants for carpet backing and as a major component of producer finishes for man-made fibers. Problems have, nevertheless, been encountered in that such ethoxylated-castor oils have been difficult to dissolve or disperse in an aqueous medium because of their tendency to form gels of high viscosity when brought into contact with water. To overcome the before-mentioned gelling problems, the prior art has resorted to the use of heat and/or powerful agitation to break up and dissolve the gel to form an aqueous admixture.
- High temperature lubricants for use in textile processing operations, such a gem disubstituted alicyclic compound in which the ring portion of the compound, e.g., a cycloaliphatic hydrocarbyl containing about 5 to about 7 carbon atoms, is substituted by a polyalkyleneoxy chain to thereby render same water-soluble or water-dispersible are disclosed in U. S. Patent Number 4,044,033.
- the polyalkyleneoxy chain which is attached to a ring carbon through a functional group, such as a hydroxyl group, is stated to be an alkylene oxide, such as ethylene oxide or propylene oxide.
- an object of the present invention is to provide an improved castor oil derivative useful as a textile lubricant which does not suffer from the problem of gel formation when contacted with an aqueous medium.
- Another object of the invention is to provide an improved textile lubricant which is not reactive with the textile material and can be removed easily therefrom after processing of same.
- a substantially water-soluble or water-dispersible non-water gelling alkyleneoxy substituted castor oil composition having at least 1 alkyleneoxy moiety generally represented as ( ⁇ CH 2 CH 2 O) ⁇ x (C 3 or C 4 alkyleneoxy constituent)yH wherein x is an integer of from 0 to about 45 and the total ( ⁇ CH 2 CH 2 O) ⁇ constituent in said alkyleneoxy substituted castor oil is not more than about 90, and y is an integer of from 0.3 to about 10 and the total iC 3 or C 4 alkyleneoxy constituent) in said alkyleneoxy substituted castor oil is at least 1 and not more than about 30.
- an improved method for reducing friction of a textile material and processing equipment during a textile processing operation which comprises contacting the textile material prior to and/or during processing with an aqueous admixture containing an effective amount of a non-water gelling alkyleneoxy substituted castor oil lubricant so as to provide from about 0.5 to about 5 weight percent of the lubricant on the textile material.
- the alkyleneoxy substituted castor oil lubricant contains at least one alkyleneoxy moiety wherein the alkylene moiety is represented as ( ⁇ CH 2 CH 2 O) ⁇ x (C 3 or C 4 alkyleneoxy constituent)yH wherein x is an integer of from 0 to about 45 and the total ( ⁇ CH 2 CH 2 O) ⁇ constituent is not more than about 90, and y is an integer of from about 0.3 to about 10 and the total fC 3 or C 4 alkyleneoxy constituent) in said lubricant is at least 1 and not more than about 30.
- the subject invention relates to a substantially water-soluble or water-dispersible non-water gelling alkyleneoxy substituted castor oil composition and to a method for using same wherein the alkyleneoxy moiety of such composition contains at least one alkyleneoxy moiety represented generally by the formula ( ⁇ CH 2 CH 2 O) ⁇ x (C 3 or C 4 alkyleneoxy constituent) y H wherein x is an integer of from 0 to about 45 and the total ( ⁇ CH 2 CH 2 0) ⁇ constituent in said alkyleneoxy substituted castor oil is not more than about 90, and y is an integer of from 0.3 to about 10 and the total ( ⁇ C 3 or C 4 alkyleneoxy constituent) in said alkyleneoxy substituted castor oil is at least 1 and not more than about 30.
- the alkyleneoxy moiety of such composition contains at least one alkyleneoxy moiety represented generally by the formula ( ⁇ CH 2 CH 2 O) ⁇ x (C 3 or C 4 alkyleneoxy constituent) y H wherein x is an integer of from
- the alkyleneoxy moiety must contain at least one mole of the C 3 or C 4 alkyleneoxy constituent.
- C 3 or C 4 alkyleneoxy constituent is to be understood to be propylene oxide, butylene oxide, including 1-butylene oxide as well as 2-butylene oxide. While the presence of either the C 3 or C 4 alkyleneoxy constituent in the alkyleneoxy moiety of the alkyleneoxy substituted castor oil composition will provide the desired non-water gelling properties to such composition, especially desirable results have been obtained wherein such C 3 or C 4 alkyleneoxy constituent is propylene oxide.
- non-water gelling as used in the subject disclosure is to be understood to mean that upon admixing the alkyleneoxy substituted castor oil composition into an aqueous medium, a resulting admixture is formed which may either be an aqueous solution or an aqueous emulsion containing the desired composition. However, when an emulsion is formed, it is a very finely divided emulsion and thus, would be considered water-dispersible.
- the term “castor oil” is to be understood to be a generic term for a pale amber viscous liquid derived from the seed of the plants "Ricinus Cummunis" of the family "Eurphorbiaceae”.
- Castor oil is one of the few naturally occurring glycerides that approaches being a pure compound since the fatty acid portion is nearly 90 % richinoleic.
- the average fatty acid composition of castor oil is 86% richinoleic, 8.5% oleic, 3.5% linoleic, 0.5 - 2% stearic, and 1-2% dihydroxy stearic acid.
- castor oil can generally be represented by the formula Of course, as previously indicated, castor oil is understood to contain minor amounts of other components.
- the term "castor oil” as meant herein is well understood in the industry and can be readily obtained by those wishing to obtain such.
- the substantially water-soluble or water-dispersible non-water gelling alkyleneoxy substituted castor oil composition for use in textile processing in accordance with the present invention contains at least one alkyleneoxy moiety which can be generally represented by the formula ( ⁇ CH 2 CH 2 O) ⁇ x (C 3 or C 4 alkyleneoxy constituent) H wherein x and y are as previously defined.
- each alkyleneoxy moiety of the alkyleneoxy substituted castor oil composition contains from about 0 to about 15 moles of ethylene oxide, e.g. x is from 0 to about 15, and the total moles of such ethylene oxide in the molecule is not more than about 45 and when each alkyleneoxy moiety further contains from about 0.3 to about 10 moles of the C 3 or C 4 alkyleneoxy constituent, e.g., y is from about 0.3 to about 10, and the total number of moles of the C 3 or C 4 alkyleneoxy constituent in the alkyleneoxy substituted castor oil composition is from at least 1 to about 30.
- the alkyleneoxy substituted castor oil composition can be typically illustrated by the following formula wherein x and y are as previously defined and z is an integer of 0 to 1. wherein x and y are as previously defined and z is an integer of 0 or 1.
- x and y are as previously defined and z is an integer of 0 or 1.
- the alkyleneoxy constituent of the alkyleneox y moiety is a C 3 alkyleneoxy constituent, e.g., propylene oxide
- z such represents the alkyleneoxy constituent being a butylene oxide.
- the non-water gelling alkyleneoxy substituted castor oil composition of the present invention can be prepared by employing ethoxylation and propoxylation or butoxylation procedures which are well known in the art. To illustrate such preparation the following is set forth. However, it is to be understood that many other methods of preparation can be envisioned and thus the subject invention is to not be limited only to the method of pre p a-ration as set forth hereinafter.
- the resulting product e.g., the ethoxylated castor oil is then propoxylated and/or butoxylated with an effective amount of propylene oxide or butylene oxide to insure that at least one mole of propylene oxide or butylene oxide per mole of castor oil is reacted therewith.
- propoxylated and/or butoxylated with an effective amount of propylene oxide or butylene oxide to insure that at least one mole of propylene oxide or butylene oxide per mole of castor oil is reacted therewith.
- the reactor In carrying out the desired ethoxylation it is important to insure that the reactor is in a clean and dry condition. Thereafter, the castor oil is charged into the reactor along with a minor amount of sodium hydroxide flake. Agitation is then commenced within the reactor and vacuum stripping in the magnitude of 25 to 28 inches is likewise commenced. Thereafter, the reactor and contents therein is heated to a temperature of from about 100°C to about 150°C while maintaining a vacuum on the reactor for a period of time after the reactants within the reactor have reached the desired temperature. Thereafter, the vacuum on the reactor is broken with nitrogen and the reactor is purged, preferably about two times, followed by venting. However, the pressure on the reactor should be maintained up to about 150 psi.
- the temperature of the reactants is then increased to about 145-150°C at which time the desired amount of ethylene oxide is introduced into the reactor.
- the reactor is maintained at such reaction conditions for a period of time to allow substantially complete reaction of the ethylene oxide with the castor oil. Thereafter, the reactor is vacuum stripped to remove any unreactive ethylene oxide and then repressured with an inert gas, such as with nitrogen, for the subsequent propoxylation or butoxylation of the ethoxylated castor oil.
- the temperature of the reactor is preferably reduced to a temperature of from about 110 to 140 and the propylene oxide or butylene oxide is added to the reactor in a predetermined amount.
- the pressure on the reactor should gradually increase upon the addition of the propylene oxide or butylene oxide. Generally a pressure of less than about 60 psi is maintained in the reactor during the propoxylation or butoxylation step.
- the reaction of propylene oxide or butylene oxide will generally be somewhat more sluggish than that of the ethylene oxide particularly where the concentration of propylene oxide or butylene oxide is low.
- the reaction is held at reaction temperature for about one hour after all the propylene oxide or butylene oxide has been added to the reactor. Thereafter, the product is vacuum stripped to remove any unreacted constituents from the reactor. It is advisable at this time to submit a sample of the resulting product for analysis to see if the desired amount of propoxylation or butoxylation has occurred. If additional propoxylation or butoxylation is determined to be necessary, such can be readily obtained by the addition of a propylene oxide or butylene oxide charge to the reactor and the maintaining of the reactor in the before-mentioned reaction conditions.
- the product is again stripped well to remove any residual propylene oxide or butylene oxide. Thereafter, the resulting ethoxylated-propoxylated or butyoxylated castor oil composition is then cooled under nitrogen to a temperature of less than about 100°C. If required, the product can be bleached to the color specification using any suitable bleaching agent, such as 30% hydrogen peroxide. The product can then be recovered from the reactor and be pH adjusted if desired.
- compositions so prepared e.g., the non-water gelling alkyleneoxy substituted castor oil composition of the present invention in which the total amount of the C 3 or C 4 alkyleneoxy constituent is present in the molecule in at least one mole can thereafter be employed as a lubricant in the textile processing operations, such as tufting, texturing, spinning, or the like, such operations being well known in the textile processing art.
- a lubricant in the textile processing operations, such as tufting, texturing, spinning, or the like, such operations being well known in the textile processing art.
- an aqueous admixture containing an effective amount of the substantially water-soluble or water-dispersible non-water gelling alkyleneoxy substituted castor oil composition as described hereinbefore, one can substantially reduce the friction of a textile material and processing equipment during the textile processing operations.
- any suitable means can be employed to apply the alkyleneoxy substituted castor oil composition to the textile material, such as by passing the textile material, e.g., fibers, yarns, and the like, through a bath containing effective amounts of alkyleneoxy substituted castor oil composition, or by passing the textile material over a saturated roll containing the aqueous admixture of such castor oil constituent, or by direct spraying of the textile material with same.
- the amount of the non-water gelling alkyleneoxy substituted castor oil lubricant which is applied to the textile material, e.g., the fibers, yarns, and the like can vary widely but will generally be from about 0.5 to about 5 weight percent.
- the amount of the alkyleneoxy substituted castor oil composition present in the aqueous admixture can vary widely, such being due to a large extent upon the particular make-up of the textile material, as well as its wet pick-up characteristics. Generally, however, we have found that when the aqueous admixture contains from about 0.5 percent to about 30 weight percent of the alkyleneoxy substituted castor oil composition that the desired amount of such lubricant, e.g., from about 0.5 to about 5 weight percent, can be applied to substantially any textile material.
- the aqueous admixture containing the alkyleneoxy substituted castor oil lubricant can be applied prior to and/or during such processing steps, the particular mode of application being left to the prerogative of those skilled in the art and their particular processing techniques.
- Product No. 1 The product so produced and removed from the reactor is hereinafter referred to as Product No. 1 and contained about 43 moles of ethylene oxide per mole of castor oil and about 1 mole of propylene oxide per mole of castor oil.
- Example II To the remaining product in the reactor from Example II was charged an additional 1.4 kg of propylene oxide which was allowed to react as in Example I. The product was then vacuum stripped, cooled, and discharged from the reactor. The product so produced and removed from the reactor is hereinafter referred to as Product No. 3 and contained about 43 moles of ethylene oxide per mole of castor oil and about 6 moles of propylene oxide per mole of castor oil.
- a 10 gallon stainless steel reactor was charged with 10.5 kg of castor oil and 80 grams of flaked potassium hydroxide. This charge was reacted with first 13.0 kg ethylene oxide and then 0.7 kg propylene oxide using the procedure described in Example I except that no ethoxylate was discarded. A 3.6 kg portion of the product was removed from the reactor leaving the remainder for subsequent reactions.
- the product so produced and removed from the reactor is hereinafter referred to as Product No. 4 and contained about 26 moles of ethylene oxide per mole of castor oil and about 1 mole of propylene oxide per mole of castor oil.
- Example IV To the reaction mass remaining in the reactor of Example IV was added 1.1 kg of propylene oxide. After reaction as in Example II, 3.6 kg of product was removed and the remaining material was retained for subsequent reactions.
- the product so produced and removed from the reactor is hereinafter referred to as Product No. 5 and contained about 26 moles of ethylene oxide per mole of castor oil and about 3 moles of propylene oxide per mole of castor oil.
- Product No. 6 contained about 26 moles of ethylene oxide per mole of castor oil and about 6 moles of propylene oxide per mole of castor oil.
- Example VI To the reaction mass remaining in the reaction at the end of Example VI was added 2.3 kg of propylene oxide. After reaction as in Example II, 17.7 kg of product was collected. The product so produced and removed from the reactor is hereinafter referred to as Product No. 7 and contained about 26 moles of ethylene oxide per mole of castor oil and about 12 moles of propylene oxide per mole of castor oil.
- Example I To the 10 gallon reactor of Example I was charged 15.9 kg of castor oil and 0.5 kg of flaked potassium hydroxide. This charge was reacted with first 4.5 kg of ethylene oxide and then 10 kg of propylene oxide using the procedure of Example IV. A 7.3 kg portion of the product was removed from the reactor and the remainder was retained for subsequent reactions.
- the product so produced is hereinafter referred to as Product No. 8 and contained about 6 moles of ethylene oxide per mole of castor oil and about 10 moles of propylene oxide per mole of castor oil.
- Example VIII The reaction mass remaining in Example VIII was reacted with 7.7 kg of propylene oxide using the procedure described in Example II. A 7.3 kg portion of the product was removed from the reactor and the remaining product was used for a subsequent reaction.
- the product so produced and recovered from the reactor is hereinafter referred to as Product No. 9 and contained about 6 moles of ethylene oxide per mole of castor oil and about 20 moles of propylene oxide per mole of castor oil.
- Example II The reaction mass remaining at the end of Example IX was reacted with 5.9 kg of propylene oxide as using the procedure described in Example II.
- the product so produced and recovered from the reactor is hereinafter referred to as Product No. 10 and contained about 6 moles of ethylene oxide per mole of castor oil and about 30 moles of propylene oxide per mole of castor oil.
- Example I The reactor of Example I was charged with 18.1 kg of castor oil and 0.5 kg of flaked potassium hydroxide. Propylene oxide, 11.4 kg was combined with the castor oil as described in Example IV. Seven and three tenths kilograms of product was removed from the reactor for characterization and the remainder of the reaction mass was retained in the reactor for further reaction.
- the product so produced and recovered from the reactor is hereinafter referred to as Product No. 11 and contained about 10 moles of propylene oxide per mole of castor oil.
- Example XI To the reaction mass remaining in the reactor of Example XI was added an additional 8.6 kg of propylene oxide. After reaction as described in Example II, 3.6 kg of product was removed for characterization and the remaining material was retained in the reactor for further reaction.
- the product so produced and recovered from the reactor is hereinafter referred to as Product No. 12 and contained about 20 moles of propylene oxide per mole of castor oil.
- Example XII To the reaction mass remaining in the reactor of Example XII was charged an additional 6.8 kg of propoylene oxide. The reaction was executed as in Example II. Thirty-one and one tenth kilograms of product were collected after the reaction was complete. The product so produced and recovered from the reactor is hereinafter referred to as Product No. 13 and contained about 30 moles of propylene oxide per mole of castor oil.
- Example I The procedure of Example I was carried out using charges of 6.8 kg of castor oil, 0.2 kg potassium hydroxide, 36.4 kg ethylene oxide. Before addition of 0.5 kg of propylene oxide, 10.5 kg of the ethoxylate was removed from the reactor and discarded. A sample of the product, 3.6 kg, was removed for characterization and the remainder was retained in the reactor for further reaction.
- Product No. 14 The product so produced and recovered from the reactor is hereinafter referred to as Product No. 14 and contained about 128 moles of ethylene oxide per mole of castor oil and about 2 moles of propylene oxide per mole of castor oil.
- Example XIV To the reaction mass retained in the reactor of Example XIV, was added 0.5 kg propylene oxide which was allowed to react as in Example II. A 3.6 kg sample od this product was removed and the remainder was retained in the reactor for subsequent reaction.
- the product so produced and recovered from the reactor is hereinafter referred to as Product No. 15 and contained about 128 moles of ethylene oxide per mole of castor oil and about 4 moles of propylene oxide per mole of castor oil.
- Example XV To the reaction mass retained in the reactor of Example XV was added 2.7 kg of propylene oxide which was reacted according to the procedure of Example II. A 3.6 kg portion of the resulting product was removed from characterization and the bulk of the material was retained in the reactor for further reaction.
- the product so produced and recovered from the reactor is hereinafter referred to as Product No. 16 and contained about 128 moles of ethylene oxide per mole of castor oil and about 18 moles of propylene oxide per mole of castor oil.
- Example XVI To the reaction mass retained in the reactor of Example XVI was added 2.3 kg of propylene oxide which was reacted according to the procedure of Example II. A 3.6 kg portion of the resulting product was removed and the bulk of the material was retained in the reactor for further reaction.
- the product so produced and recovered from the reactor is hereinafter referred to as Product No. 17 and contained about 128 moles of ethylene oxide per mole of castor oil and about 31 moles of propylene oxide per mole of castor oil.
- Example XVII To the reaction mass retained in the reactor of Example XVII was added an additional 4.1 kg of propylene oxide which was reacted according to the procedure of Example II. There was obtained.19.3 kg of product.
- The.product so produced is hereinafter referred to as Product No. 18 and contained about 128 moles of ethylene oxide per mole of castor oil and about 60 moles of propylene oxide per mole of castor oil.
- Control Product A was an ethoxylated castor oil containing about 26.5 moles of ethylene oxide and no propylene oxide.
- Control Product B was an ethoxylated castor oil containing about 33 moles of ethylene oxide and no propylene oxide.
- Each of the Control Products A and B are prepared similar to the procedure of Example I except that no propylene oxide is added.
- Friction measurements were made using a RochschildF-Meter by passing a continuous filament manmade fiber with 1% applied lubricant over a 3/8" round stainless steel pin. Both 70 denier 34 filament nylon 66 and polyester fibers, which had been extracted to remove all producer finish, were used. Samples and controls were preconditioned at 70°F and 65% R.H. for 24 hours prior to running.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Lubricants (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88741078A | 1978-03-16 | 1978-03-16 | |
| US887410 | 1978-03-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0004353A2 true EP0004353A2 (de) | 1979-10-03 |
| EP0004353A3 EP0004353A3 (de) | 1979-10-31 |
Family
ID=25391076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP79100801A Withdrawn EP0004353A3 (de) | 1978-03-16 | 1979-03-15 | Im Wasser kein Gel formendes alkylenoxysubstituiertes Rizinusöl |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0004353A3 (de) |
| JP (1) | JPS54163905A (de) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3323880C1 (de) * | 1983-07-02 | 1984-08-16 | Th. Goldschmidt Ag, 4300 Essen | Polyoxyalkylenether des Rizinusoeles und deren Verwendung zur Herstellung von Polyurethanen |
| WO1993024603A3 (en) * | 1992-06-02 | 1994-03-17 | Unilever Plc | Liquid cleaning products |
| EP0969078A3 (de) * | 1992-07-08 | 2000-02-23 | Henkel Corporation | Verfahren zur Behandlung von geformten Metalloberflächen |
| US6849581B1 (en) | 1999-03-30 | 2005-02-01 | Bj Services Company | Gelled hydrocarbon compositions and methods for use thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6080331B1 (ja) * | 2016-06-28 | 2017-02-15 | 竹本油脂株式会社 | 合成短繊維用処理剤、ポリエステル系短繊維及びその製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2971965A (en) * | 1958-08-26 | 1961-02-14 | Visco Products Co | Oil adducts |
| GB1047253A (de) * | 1963-05-13 | 1966-11-02 |
-
1979
- 1979-03-15 EP EP79100801A patent/EP0004353A3/de not_active Withdrawn
- 1979-03-16 JP JP3098179A patent/JPS54163905A/ja active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3323880C1 (de) * | 1983-07-02 | 1984-08-16 | Th. Goldschmidt Ag, 4300 Essen | Polyoxyalkylenether des Rizinusoeles und deren Verwendung zur Herstellung von Polyurethanen |
| EP0130458A3 (en) * | 1983-07-02 | 1986-04-30 | Th. Goldschmidt Ag | Polyoxyalkylene ethers of castor oil and their use in the production of polyurethanes |
| WO1993024603A3 (en) * | 1992-06-02 | 1994-03-17 | Unilever Plc | Liquid cleaning products |
| US5378387A (en) * | 1992-06-02 | 1995-01-03 | Lever Brothers Company, Division Of Conopco, Inc. | Non-aqueous liquid cleaning products comprising polyalkoxylated derivatives of castor oil ricinoleic acid and analogous fatty alcohols |
| EP0969078A3 (de) * | 1992-07-08 | 2000-02-23 | Henkel Corporation | Verfahren zur Behandlung von geformten Metalloberflächen |
| US6849581B1 (en) | 1999-03-30 | 2005-02-01 | Bj Services Company | Gelled hydrocarbon compositions and methods for use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0004353A3 (de) | 1979-10-31 |
| JPS54163905A (en) | 1979-12-27 |
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Inventor name: STADALSKY, JOHN FRANK Inventor name: MILEY, JOHN WULBERN |