US2355823A - Polyglycol ethers of higher second - Google Patents
Polyglycol ethers of higher second Download PDFInfo
- Publication number
- US2355823A US2355823A US2355823DA US2355823A US 2355823 A US2355823 A US 2355823A US 2355823D A US2355823D A US 2355823DA US 2355823 A US2355823 A US 2355823A
- Authority
- US
- United States
- Prior art keywords
- alcohols
- polyglycol ethers
- acid
- ketones
- ethylene oxide
- 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
Links
- 229920000151 polyglycol Polymers 0.000 title description 20
- 239000010695 polyglycol Substances 0.000 title description 20
- 150000002170 ethers Chemical class 0.000 title description 18
- 229940117927 Ethylene Oxide Drugs 0.000 description 20
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000002576 ketones Chemical class 0.000 description 16
- 150000001298 alcohols Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 125000004432 carbon atoms Chemical group C* 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000009736 wetting Methods 0.000 description 12
- -1 aliphatic ketones Chemical class 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 150000003333 secondary alcohols Chemical class 0.000 description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N Nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 8
- 239000003599 detergent Substances 0.000 description 8
- 238000005187 foaming Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000003513 alkali Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N Heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000005643 Pelargonic acid Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 238000005238 degreasing Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 229960002446 octanoic acid Drugs 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N Heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 235000021360 Myristic acid Nutrition 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N Potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 235000001211 Talinum portulacifolium Nutrition 0.000 description 2
- 240000004958 Talinum portulacifolium Species 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N Undecylic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005097 cold rolling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000004900 laundering Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
Definitions
- the present invention relates to polyglycol ethers of higher fatty alcohols active in lowering surface tension and a process for the production thereof.
- n represents a whole number from 4 to 16.
- the acids mentioned thus contain no branchings in their carbon skeleton. It is known that these fatty acids can be converted into ketones of the typ CH3 (CH2) n.CO(CH2)'m.CH3
- n and m represent whole numbers from .4 to 16.
- n may also be :m; but 11. and m are generally different, when mixtures of various fatty acids are converted into ketones.
- a further object of the present invention is to convert these secondary alcohols into polyglycol ethers of the type CHa(CH2),..CH(CHz) W011i 1n represent a whole number from represents a whole number-from siderable quantities of ethyleneoxide in the presence of small quantities of caustic alkali or alkali alcoholates, forming valuable agents active in lowering surface tension, whereby, according to my invention, 6 to 20 mols ethylene oxide are used per mol alcohol.
- conversion is effected in a closed vessel, preferably an autoclave equipped with a stirring device, ata temperature of from to 200 degrees C.
- the ethylene oxide may be admitted either in gaseous form, or in liquid form by means of a measuring pump. Conversion is initiated by raising the temperature to about 100 degrees C. According to the quantity of reagents present, the reaction mixture is heated to a temperature of up to 200 degrees C. by the heat of-reaction liberated.
- the reaction products are wax-like, If necessary, more particularly when the reagents used are of commercial grade, they can be freed by distillation in vacuo from readily volatile components and any quantities of alcohol not affected by the reaction.
- the said wax-like products are soluble in water, especially in hot water, giving a clear solution. They are able to emulsify oils, fats, and tarry compounds to a remarkable degree. They further possess an excellent property of wetting textiles, metals, glass, and porcelain, more particularly in conjunction with alkaline detergents.
- the products prepared by addition of ethylene oxide to the said secondary alcohols are specially well suited for cleansing and degreasing articles soiled with oil or tar, or sheet metal and other materials treated by oil hardening, cold rolling, or other method of fabrication.
- the said wax-like products soluble in water can be successfully used in laundering and for the cleansing of very dirty cleaning cloths, workmens overalls, and textiles of a similar description used in industries'and trades.
- the detergent liquors prepared from the said products develop much less froth than do other polyglycol ethers with a neutral-reaction, which feature makes it possible to use them in washing and spraying distillation in vacuo.
- the said mixture of ketones is then converted by hydrogenation, for. example, according to the process of U. S. Patent No. 2,108,133, into a mixture came corresponding secondary alcoholsp 22.5 kilos of the said mixture of alcohols are gradually treated with 40 kilos ethylene oxide in the presence of 400 grams very finely ground caustic soda at an initial temperature of about 100 degrees C. in an autoclave equipped with an agitator, while stirring well.
- n and m represent respectively a Whole number from 4 to 16, and a: a whole number from 5 to 19.
- the process of producing compounds having high wetting power and low foaming power from compounds having hydrocarbon chains of inadequate lipophilic characteristics which comprises forming ketones from fatty acids having from 6 to 9 carbon atoms, hydrogenating the ketones thereby forming secondary alcohols and reacting the alcohols with ethylene oxide in a quantity between 6 'to 20 mols to each mol of alcohol in a closed container at a temperature of 100 to 200 C. in 'the presence of caustic soda to form polyglycol ethers of said alcohols thereby imparting hydrophilic qualities to balance the lipophilic qualities of the hydrocarbon chains of the alcoholic component.
Description
Patented Aug. 15, 1944 POLYGLYCOL Erncns OF HIGHER SECOND- ABY, MONOHYDRIC ALCOHOLS Fritz Schlegel, Duesseldorf,
by mesnc assignments, to The Procter &
Gamble Company, Cincinnati, Ohio, a corporation of Ohio Germany, assignor,
No Drawing. Application December 5, 1940, Se-
rial No. 368,628. In Germany December 21,
6 Claims.
The present invention relates to polyglycol ethers of higher fatty alcohols active in lowering surface tension and a process for the production thereof.
It is well known that normal fatty acids, such as caproic acid, oenanthylic acid, caprylic acid, pelargonic acid, capric acid, n-undecylic acid, lauric acid, myristic acid, palmitic acid, margaric acid, and stearic acid, contain the carbon skeleton in the form of a straight chain. These carboxylic acids possess the general formula CH3 (CH2) 1;.COOH
whereby n represents a whole number from 4 to 16. The acids mentioned thus contain no branchings in their carbon skeleton. It is known that these fatty acids can be converted into ketones of the typ CH3 (CH2) n.CO(CH2)'m.CH3
whereby n and m represent whole numbers from .4 to 16. When pure individuals are converted into ketones, n may also be :m; but 11. and m are generally different, when mixtures of various fatty acids are converted into ketones.
It is known that these straight-chain ketones can be converted by hydrogenation into the corresponding secondary alcohols of the type CH3(CH2) 1;.CHOH. (CH2) ,m.CH3
whereby it and m have the values just described.
The conversion of the said secondary aliphatic straight-chain alcohols into neutral bodies active in lowering surface tension is one of the objects of the present invention.
A further object of the present invention is to convert these secondary alcohols into polyglycol ethers of the type CHa(CH2),..CH(CHz) W011i 1n represent a whole number from represents a whole number-from siderable quantities of ethyleneoxide in the presence of small quantities of caustic alkali or alkali alcoholates, forming valuable agents active in lowering surface tension, whereby, according to my invention, 6 to 20 mols ethylene oxide are used per mol alcohol.
According to my invention, conversion is effected in a closed vessel, preferably an autoclave equipped with a stirring device, ata temperature of from to 200 degrees C. The ethylene oxide may be admitted either in gaseous form, or in liquid form by means of a measuring pump. Conversion is initiated by raising the temperature to about 100 degrees C. According to the quantity of reagents present, the reaction mixture is heated to a temperature of up to 200 degrees C. by the heat of-reaction liberated.
Addition of ethylene oxide to the secondary alcohols takes place in the presence of an agent with an alkaline reaction, whereby the presence of 0.5 to 2 per cent of caustic potash or caustic soda, calculated on the alcohols, has proved to be the most efiective. But alkali alcoholates, such as sodium methylate, sodium ethylate, potassium ethylate, and the like, may also be used in the same proportions.
The reaction products are wax-like, If necessary, more particularly when the reagents used are of commercial grade, they can be freed by distillation in vacuo from readily volatile components and any quantities of alcohol not affected by the reaction. The said wax-like products are soluble in water, especially in hot water, giving a clear solution. They are able to emulsify oils, fats, and tarry compounds to a remarkable degree. They further possess an excellent property of wetting textiles, metals, glass, and porcelain, more particularly in conjunction with alkaline detergents. For that reason, the products prepared by addition of ethylene oxide to the said secondary alcohols are specially well suited for cleansing and degreasing articles soiled with oil or tar, or sheet metal and other materials treated by oil hardening, cold rolling, or other method of fabrication. The said wax-like products soluble in water can be successfully used in laundering and for the cleansing of very dirty cleaning cloths, workmens overalls, and textiles of a similar description used in industries'and trades. Apart from that surprisingly good property of wetting and cleansing, the detergent liquors prepared from the said products develop much less froth than do other polyglycol ethers with a neutral-reaction, which feature makes it possible to use them in washing and spraying distillation in vacuo.
rying it into practical effect, but my invention is not confined to this example.
Example A mixture of caproic acid. oenanthylic acid, caprylic acid, and pelargonic acid, produced by the oxidation of a straight-chain parafiin, is converted by ketonizing it in any familiar way into a mixture of aliphatic ketones with a chain length of from 11 to 17 carbon atoms. The said mixture of ketones is then converted by hydrogenation, for. example, according to the process of U. S. Patent No. 2,108,133, into a mixture came corresponding secondary alcoholsp 22.5 kilos of the said mixture of alcohols are gradually treated with 40 kilos ethylene oxide in the presence of 400 grams very finely ground caustic soda at an initial temperature of about 100 degrees C. in an autoclave equipped with an agitator, while stirring well. It can easily be demonstrated by measurement of the pressure that the ethylene oxide begins to be absorbed at a temperature of about 100 de rees C. The heat of reaction liberated serves to raise the temperature of the reaction mixture to from 170 to 180 degrees C., which temperature is maintained,
either by cooling or by additional application of heat, until the ethylene oxide has been completely absorbed.
After completion of the reaction, the reaction mixture is freed from unconverted alcohol by i The residue isa wax-like product which is admirably adapted for the preparation of a detergent liquor for degreasing light metals or oil-hardened iron parts. Such a detergent liquor should contain preferably a mix- Now what I claim is:
1. As a new product, compounds having the whereby n and m represent respectively a Whole number from 4 to 16, and a: a whole number from 5 to 19.
2. As a new product a wax-like mass consisting of polyglycol ethers of higher molecular, monohydric secondary, straight chain aliphatic alcohols. having at least 11 carbon atoms.
3. Compounds of waxy consistency having high wetting powers but low foaming power consisting of polyglycol ethers of monohydric secondary straight chain aliphatic alcohols having from 11 to 35 carbon atoms in the chain.
4. The process of producing polyglycol ethers having high wetting powers and low foaming power from higher molecular, monohydric secondary straight chain aliphatic alcohols derived by the hydrogenation of ketones obtained from fatty acids having from 6 to 18 carbon atoms in the molecules, which comprises heating such alcohols with from 6 to 20 mols of ethylene oxide per mol of alcohol in a closed container at a temperature of .to 200 C. in the presence of an alkalinity-imparting agent.
5. The process of producing compounds having high wetting power and low foaming power from compounds having hydrocarbon chains of inadequate lipophilic characteristics, which comprises forming ketones from fatty acids having from 6 to 9 carbon atoms, hydrogenating the ketones thereby forming secondary alcohols and reacting the alcohols with ethylene oxide in a quantity between 6 'to 20 mols to each mol of alcohol in a closed container at a temperature of 100 to 200 C. in 'the presence of caustic soda to form polyglycol ethers of said alcohols thereby imparting hydrophilic qualities to balance the lipophilic qualities of the hydrocarbon chains of the alcoholic component.
6. Compounds of waxy consistency having high wetting powers but low foaming power consisting of polyglycol ethers of .monohydric secondary straight chain aliphatic alcohols having from 11-17 carbon atoms in the chain.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2355823A true US2355823A (en) | 1944-08-15 |
Family
ID=3433957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2355823D Expired - Lifetime US2355823A (en) | Polyglycol ethers of higher second |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2355823A (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2508036A (en) * | 1950-05-16 | Compounds having high wetting | ||
| US2508035A (en) * | 1950-05-16 | Compounds having surface activity | ||
| US2516685A (en) * | 1944-04-19 | 1950-07-25 | American Chem Paint Co | Process of preparing iron and aluminum surfaces to receive organic coatings and solution therefor |
| US2520733A (en) * | 1946-08-26 | 1950-08-29 | Shell Dev | Polymers of trimethylene glycol |
| US2527970A (en) * | 1950-10-31 | Hydroxy ethers and process for | ||
| US2617830A (en) * | 1950-06-30 | 1952-11-11 | Monsanto Chemicals | Polyglycol ethers of 7-ethyl-2-methyl-undecanol-4 |
| US2620360A (en) * | 1952-12-02 | Manufacture of glycol ethers | ||
| US2624766A (en) * | 1949-10-15 | 1953-01-06 | Monsanto Chemicals | Tridecenyl alcohols |
| US2671115A (en) * | 1954-03-02 | Ethers of z-butyloc | ||
| US2671116A (en) * | 1954-03-02 | Polyglycol ethers of z | ||
| US2782240A (en) * | 1952-11-21 | 1957-02-19 | Dow Chemical Co | Ethers of polyoxyalkylene glycols |
| US2846348A (en) * | 1954-10-26 | 1958-08-05 | Owens Corning Fiberglass Corp | Glass fiber sizing |
| US2870220A (en) * | 1953-08-11 | 1959-01-20 | Union Carbide Corp | Production of nonionic surface active agents |
| US2950818A (en) * | 1955-03-05 | 1960-08-30 | Hoechst Ag | Flotation process |
| US2965678A (en) * | 1951-12-28 | 1960-12-20 | Gen Aniline & Film Corp | Polyoxyethylene ethers of branched chain alcohols |
| US3350462A (en) * | 1964-11-24 | 1967-10-31 | Gen Aniline & Film Corp | Preparation of nonionic surface active agents of high wetting power |
| US3372201A (en) * | 1966-06-17 | 1968-03-05 | Gen Aniline & Film Corp | Alkoxylation of secondary alcohols |
| US4967017A (en) * | 1988-04-02 | 1990-10-30 | Henkel Kommanditgesellschaft Auf Aktien | Alcohol ethoxylates of reduced EO content or residual PO content |
-
0
- US US2355823D patent/US2355823A/en not_active Expired - Lifetime
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2671115A (en) * | 1954-03-02 | Ethers of z-butyloc | ||
| US2671116A (en) * | 1954-03-02 | Polyglycol ethers of z | ||
| US2508036A (en) * | 1950-05-16 | Compounds having high wetting | ||
| US2527970A (en) * | 1950-10-31 | Hydroxy ethers and process for | ||
| US2508035A (en) * | 1950-05-16 | Compounds having surface activity | ||
| US2620360A (en) * | 1952-12-02 | Manufacture of glycol ethers | ||
| US2516685A (en) * | 1944-04-19 | 1950-07-25 | American Chem Paint Co | Process of preparing iron and aluminum surfaces to receive organic coatings and solution therefor |
| US2520733A (en) * | 1946-08-26 | 1950-08-29 | Shell Dev | Polymers of trimethylene glycol |
| US2624766A (en) * | 1949-10-15 | 1953-01-06 | Monsanto Chemicals | Tridecenyl alcohols |
| US2617830A (en) * | 1950-06-30 | 1952-11-11 | Monsanto Chemicals | Polyglycol ethers of 7-ethyl-2-methyl-undecanol-4 |
| US2965678A (en) * | 1951-12-28 | 1960-12-20 | Gen Aniline & Film Corp | Polyoxyethylene ethers of branched chain alcohols |
| US2782240A (en) * | 1952-11-21 | 1957-02-19 | Dow Chemical Co | Ethers of polyoxyalkylene glycols |
| US2870220A (en) * | 1953-08-11 | 1959-01-20 | Union Carbide Corp | Production of nonionic surface active agents |
| US2846348A (en) * | 1954-10-26 | 1958-08-05 | Owens Corning Fiberglass Corp | Glass fiber sizing |
| US2950818A (en) * | 1955-03-05 | 1960-08-30 | Hoechst Ag | Flotation process |
| US3350462A (en) * | 1964-11-24 | 1967-10-31 | Gen Aniline & Film Corp | Preparation of nonionic surface active agents of high wetting power |
| US3372201A (en) * | 1966-06-17 | 1968-03-05 | Gen Aniline & Film Corp | Alkoxylation of secondary alcohols |
| US4967017A (en) * | 1988-04-02 | 1990-10-30 | Henkel Kommanditgesellschaft Auf Aktien | Alcohol ethoxylates of reduced EO content or residual PO content |
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