US2991296A - Method for improving foam stability of foaming detergent composition and improved stabilizers therefor - Google Patents
Method for improving foam stability of foaming detergent composition and improved stabilizers therefor Download PDFInfo
- Publication number
- US2991296A US2991296A US795608A US79560859A US2991296A US 2991296 A US2991296 A US 2991296A US 795608 A US795608 A US 795608A US 79560859 A US79560859 A US 79560859A US 2991296 A US2991296 A US 2991296A
- Authority
- US
- United States
- Prior art keywords
- foam
- grease
- mols
- ethylene oxide
- foaming
- 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
- 239000000203 mixture Substances 0.000 title claims description 38
- 239000006260 foam Substances 0.000 title description 52
- 239000003599 detergent Substances 0.000 title description 22
- 239000003381 stabilizer Substances 0.000 title description 22
- 238000005187 foaming Methods 0.000 title description 20
- 238000000034 method Methods 0.000 title description 8
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 6
- 229940102253 isopropanolamine Drugs 0.000 claims description 2
- 239000004519 grease Substances 0.000 description 32
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 229930195729 fatty acid Natural products 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 150000004665 fatty acids Chemical class 0.000 description 13
- 239000004872 foam stabilizing agent Substances 0.000 description 13
- 238000007046 ethoxylation reaction Methods 0.000 description 9
- 125000000129 anionic group Chemical group 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 235000012343 cottonseed oil Nutrition 0.000 description 5
- 239000002385 cottonseed oil Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- -1 stearic acid Chemical class 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000003925 fat Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000004851 dishwashing Methods 0.000 description 3
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical class CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000004088 foaming agent Substances 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000021360 Myristic acid Nutrition 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- MMBILEWCGWTAOV-UHFFFAOYSA-N N-(2-Hydroxypropyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCC(C)O MMBILEWCGWTAOV-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 238000004900 laundering Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZZNDQCACFUJAKJ-UHFFFAOYSA-N 1-phenyltridecan-1-one Chemical compound CCCCCCCCCCCCC(=O)C1=CC=CC=C1 ZZNDQCACFUJAKJ-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000004165 Methyl ester of fatty acids Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WCHFOOKTKZYYAE-UHFFFAOYSA-N ethoxyperoxyethane Chemical group CCOOOCC WCHFOOKTKZYYAE-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- MDYPFOFSXHBHFE-UHFFFAOYSA-N n-dodecylacetamide Chemical compound CCCCCCCCCCCCNC(C)=O MDYPFOFSXHBHFE-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical class CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 102220124522 rs746215581 Human genes 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0094—High foaming compositions
-
- 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
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
Landscapes
- 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
, 2,991,296 Patented July 4, 1961 2,991,296 METHOD FOR IMPROVING FOAM STABILITY OF FOAMING DETERGENT COMPOSITION AND HVIPROVED STABILIZERS THEREFOR Oscar L. Scherr, 4059 Perlita Ave., Los Angeles, Calif. No Drawing. Filed Feb. 26, 1959, Ser. No. 795,608 4 Claims. (Cl. 260-404) The present invention relates to novel foam stabilizers and detergents and to detergent or foaming compositions stabilized or improved by the incorporation thereof. It relates further to novel chemical compounds useful as foam stabilizers and detergents and to a method for the stabilization of foams by the incorporation of such materials into foaming detergent compositions. The invention relates further to foam stabilizers especially effective with anionic foaming agents.
Certain detergents and detergent compositions such as those containing soaps and/ or synthetic detergents or interface modifiers and particularly the anionic surface active agents, depend to a certain extent upon their ability to form at least a certain degree of foam, and the ability to maintain such foams for a sufiicient period of time to enable them to be effective in launderingcleaning and dishwashing and other dirt and grease removing applications. This is particularly important in the presence of grease since the maintenance of foam is important in facilitating the emulsification of the grease and in maintaining such emulsions in suspension. In order to improve the stability of foams, certain materials, which in themselves may or may not possess detergency, have been utilized, such as lauric monoisopropanolamide as described in U.S. Patent 2,757,143, or N-dodecyl acetamide as described in U.S. Patent 2,702,278.
Applicant has discovered novel chemical compounds which are highly effective as foam stabilizers, in foaming detergent compositions and particularly with anionic surface active agents, and which will maintain foam stability in the presence of substantial proportions of fat and grease.
It is, therefore, an object of the present invention to provide a novel chemical compounduseful as a foam stabilizing agent for foaming detergent compositions.
It is a further object of the invention to provide a foam stabilizer which Will maintain substantial foam stability in foaming detergent compositions in the presence of substantial proportions of grease and fat.
It is still a further object of the invention to provide an improved foaming detergent composition having substantial foam stability, particularly in the presence of oils, fats and grease.
It is yet another object of the product invention to greatly improve or enhance the foaming efficiency and stability as Well as the detergency, cleaning power, laundering properties and dishwashing utility of surface active agents commonly known as wetting agents or detergents, and especially the anionic surface active agents.
It is an additional object of the invention to provide a process for improving the foam stability of foaming detergents.
The above and other objects will become more fully apparent from a consideration of the. following specification:
Applicant has discovered that improved foam stabilizing agents may be obtained by the ethoxylation of the isopropanolamides of certain aliphatic carboxylic acids including certain-fatty acids and their alkyl esters, such as the .isopropanolamides of stearic, oleic, linoleic, palmi-ticand myristic acid and their alkyl esters, such as the methyl ester. The amides may be derived from the pure fatty acids or mixtures thereo f, orcommercial impure mixtures containing them, as well as directly from the oils or fats themselves such as the vegetable oils, castor oil, hydrogenated tallow or the like.
Foam stabilizers such as are now commonly being used for household detergents, both dry powdered, or flaked, and liquid, are primarily based on lauric acid or its methyl ester. The most commonly utilized stabilizers are the lauric isopropanolamide, known as LIPA and the lauric diethanol-amides, commonly known as LDA. These are efficient foam stabilizers and have a certain degree of detergency in themselves, however, they are not as effective as is desirable in the presence of substantial amounts of grease or greasy or oily soil, and hence are not completely satisfactory in dishwashing and other compositions; furthermore, these materials are fairly expensive, and lower cost, but at least equally effective or superior raw materials, would be greatly desired by the industry. p
In obtaining the fatty acids and their methyl esters from the fatty oils, such as cocoanut oil, the. high ends, namely the C14, 16 and 18 chain length fatty acids and their methyl esters are gradually accumulated as surplus materials without great value or utility. Although the lauric acid amides are substantially Water soluble and useful in the manufacture of paint stabilizers, the amides of the higher molecular weight fatty acids, such as stearic acid, are only slightly soluble in water and have no value as foam stabilizers or detergents in themselves. They are principally used as opacifiers and pearling agents in cosmetic products.
In accordance with applicants invention the novel products described are obtained by incorporating two or more ethylene oxide groups into an aliphatic carboxylic acid derivative of isopropanolamidqor into a mixture of such derivatives to' form a compound having the following structure:
where R is any aliphatic carboxylic acid radical having 13-17 or more carbon atoms and X=any whole number from 2 or higher, preferably from 2 to 20. These compounds are prepared by first preparing the isopropanolamide from monoisopropanol-amine and the fatty acids, their methyl esters, orthe corresponding oils. This is then ethoxylated by the addition of ethylene oxide to produce the desired novel product. od of preparation of thme compounds are as follows:
EXAMPLE A 23 mole of a mixture of methyl esters of fatty acids I (6325 grams) were reacted with 25.3 mols (1897.5 grams) The fatty acid esters wereof monoisopropanolamine. the still bottoms of cocoanut oil fattyacid methyl esters which had been hydrogenated and consisted essentially of 7% myristic acid ester, 45% palrnitic acid ester and 48% stearic acid ester. These still bottoms are low priced and are available in large supply, since they, have heretofore had no particular utility asbases or intermediates for chemical syntheses. For example they have been available at prices as low as 10 per 1b., at a time when C. and poured into a stainless steel pan. 'The prod Examples of the methuct was a hard, brittle, waxy cream-colored solid found to be monoisopropanolarnides of the corresponding mixed fatty acids.
EXAMPLE B 4.48 mols of the product of A (1424 grams) and 3 grams of KOH pellets were charged to a stainless steel autoclave, agitated and heated to 145 C., purged of air with nitrogen, and 8.96 mols (394 grams) of ethylene oxide added at such a rate that maximum pressure did not exceed 100 pounds. The temperature was maintained at 145 C. by means of cooling water circulated through a jacket around the autoclave and a coil internally thereof. After about 2 hours the reaction mixture was cooled to 100 C. and 6 cc. of glacial acetic acid added. The final product was a pale amber liquid which solidified to a soft paste on standing. The product was found to be the ethoxylated derivative of the fatty acid isopropanolamides from Example A, containing 2 mols of ethylene oxide per mol.
EXAMPLE C 3.23 mols (1026 grams) of the product of Example A were reacted with 19.36 mols of ethylene oxide in the presence of KOH as described in Example B. The product was the ethoxylated derivative of the fatty acid isopropanolamides from Example A containing 6 mols of ethylene oxide per mol.
EXAMPLE D 2.63 mols (835 grams) of the product of Example A, were reacted with 26.3 mols of ethylene oxide in the presence of KOH in the manner described in Example B, except that the maximum reaction temperature was 164 C.
The product was the ethoxylated derivative of the fatty acid isopropanolamides from Example A containing mols of ethylene oxide per mol.
Other ethoxylated derivatives containing other ratios of ethylene oxide were obtained in the same manner, such as the 1 mol ethoxylate, the 12 mol ethoxylate and the mol ethoxylate.
EXAMPLE E 3 mols of monoisopropanolamine lauric amide were reacted with 12 mols of ethylene oxide according to the procedure outlined in Example B. The final product was found to be the corresponding ethoxylated derivative having four mols of ethylene oxide per mol of compound.
EXAMPLE F 3 mols of monoisopanolamine stearic amide were reacted with 12 mols of ethylene oxide according to the procedure outlined in Example B. The final product was found to be the corresponding ethoxylated derivative having four mols of ethylene oxide per mol of compound.
Monoisopropanolamides of myristic acid, palmitic acid, oleic acid, and tall oil fatty acids, were prepared in the same manner as described above in Example A. The individual amides were then ethoxylated to produce ethylene oxide derivatives having from 2 to 20 mols of ethylene oxide added thereto. These were found to be superior foam stabilizers in the presence of grease as were the compounds derived from the mixed fatty acid derivatives reacted in Examples B to D inclusive, and had similar advantageous properties by comparison with LIPA or LDA.
The compounds produced in the above manner were evaluated as foam stabilizers in a series of experiments to determine effectiveness in foam stability and grease resistance by comparison with other known, commonly used eifective stabilizers heretofore utilized for these purposes. These comparisons were made by preparing standard foaming compositions, with and without known stabilizers, testing these for foam stability and grease resistance, and making the same tests after substituting the new stabilizing compound for those used in the standard compositions. The tests were carried out using a standard foam test in which 250 ml. of solution was placed in a 500 ml. cylinder and inverted 20 times to generate foam. The volume of foam was then measured and the measurement repeated at given time intervals to measure stability of the foam. Grease resistance was measured by carrying out the same procedure in the presence of successive 10 ml. additions of refined cotton seed oil, the cylinder being upended 20 times after each addition. The quantity of oil required to form a grease film on the glass was determined and this point taken as that at which the grease resistance of the foam had failed. The foaming ability and stability of the resultant foams were also measured at different time intervals. In general, if the foam volume declined substantially within 15 minutes of standing, it was considered that the foam stability in the presence of the varying amounts of grease is poor.
In each of the following examples comparisons were made using the following compounds:
LlPA Lauric isopropanolamide LDA Lauric diethanolamide Sl=-Ethoxylation product of Example A with 1 mol ethylene oxide S2=Ethoxylation product of Example B with 2 mols ethylene oxide S-4=Ethoxylation product of Example A with 4 mols ethylene oxide S-6:Ethoxylation product of Example C with 6 mols ethylene oxide S10=Etho-xylation product of Example D with 10 mols ethylene oxide S-12==Eth0xylati0n product of Example A with 12 mols ethylene oxide S-20=Ethoxylation product of Example A with 20 mols ethylene oxide L-4=Pr0duct of ethoxylation of Example E with 4 mols ethylene oxide S-4A=Product of ethoxylation of Example F with 4 mols ethylene oxide EXAMPLE I Formulation:
Foaming composition-Dodecyl benzene sulfonate Stabilizer concentration 2.5% Concentration of formulation in water 0.1%
Table 1 Foam stability Grease resistanceML refined cotton seed oil ML oil Foam to form stabigrease lizer Ini 5 15 film on tial min min. 10 20 30 40 glass ML ML ML N o rim-The asterisked figures in this and succeeding tables indicates that the foam remained stable for a longer period than 15 minutes. whereas the absence of the asterisk indicates that the foam stability declined or disappeared after 15 minutes.
The above comparisons clearly demonstrate that the initial foam formation and stability at 5 and 15 minute intervals using the new compounds is at least as good, and in some cases better, than using LIPA and LDA. In addition, grease resistance was definitely superior.
H I EXAMPLE II Table 4 Formulation:
Foaming composition20% dodcyl benzene S111- Foam stability Grease resistance'-MLrefi.ned
fonate cotton seed 011 ML oil I Foam to form Stabilizer concentration 2.5% 5 t It 5 15 g e Concentration of formulations 0.25 m i mm 2Q 30 40 50 ig ML ML ML Table 2 None-.- 255 235 210 10 10 LIP 270 270 260 40 LDA 250 240 230 30 Foam stability Grease resistanceML refined g:i"" comm Seed 011 ML 5-6:: 250 260 250 50 33%? 51-10.... 250 250 255 40 v grease s-1 240 235 215 10 met mm $42.... 275 275 270 50 11? 10 20 30 40 50 glass 15 240 240 235 50 235 225 210 250 250 250 Asm the previous example, thel mol ethoxylat e was $28 3 28 practically ineffective as a stabihzer, with or without 250 280 275 50 20 the presence of grease. On the other hand, all of the 2 28 mol and higher ethoxylates showed greatly superior foam stability and grease resistance even by comparison with LIPA and LDA.
EXAMPLE V The above data lndicate superior foam forming and 5 g q com ositio Built formula 9? dodec l foam stabilizing ability at the higher concentration of oammg p n 0 y the formulation as well as greatly superior resistance to benzene Sultanate 45% Sodmm mpoly'phosphate grease 5% SOdllll'Il slhcate, salt cake 37%, foam stabilizer 4% EXAMPLE H1 30 Concentration 0.1% Formulation: Table 5 Foaming composition-20% dodecyl benzene sul- Pa Foam stability Grease resistanee-ML refined Stabilizer concentration 5% cottonseed oil 1 oil Concentration of formulation 0.1% 2 221 llzer Ini- 5 15 film on ltiaall 10 20 30 glass Table 3 Foam stability Grease resistance-ML refined cotton seed oil ML oil 170 170 165 "-55 30 gag 175 110 100 75 30 lizer Ini- 5 15 film on 35 25 85 e tial min min. 10 20 30 40 50 glass ML ML ML 45 The above data demonstrates that in a built formula- ;8 tion, the foam forming ability and stability both with and LDA.-.1 210 210 200 20 Without grease is superior to LIPA.
28 The built formula used represents a commercial formus-oIIIII 150 50 lation. The actual detergent concentration is quite low gj fig 50 and foams normally produced do not stand up well with- S-li::: 185 180 40 out the use of a stabilizer. These formulations are used 185 40 as heavy duty detergents in laundering and cleaning.
55 EXAMPLE VI Formulation:
These data demonstrate that although the initial foam formation at the higher stabilizer concentration is somewhat lower than with LIPA and LDA, the products of the invention imparted excellent foam stability. In ad- Foaming composition. Built formula of Example V.' Concentration 0.25%.
Table 6 di-tion, the ease resistance remained superior. It is 60 significant flit the 1 mol ethoxylated product was no Foam Stablhty Grease gjtigi gj g gf refined M11011 better than, and in fact slightly poorer as a stabilizer by g 232 comparison with the use of no stabilizer, and little or lizer Ini- 5 1 5 film on no better with respect to stability in the presence of the 65 50 glass oil. Compared with the 2 mol and higher ethoxylates this material was unsatisfactory for the purpose, whereas 240 220 20 the 2 mol and higher ethoxylates were definitely superior. 23 240 225 135 3 Formulation: EXAMPLE IV 138 Foaming composition20% dodecyl benzene sulfonate Stabilizer concentration 5% The above data shows a superiority over LIPA in initial foam forming ability and stability, plus equal Formulation concentration 0.25% grease resistance at the higher concentration.
These data demonstrate that the monoisopropanolamine lauric amide ethoxylate is definitely inferior to the corresponding stearic compound and therefore that the C12 fatty acid compound is no better than no Stabilizer and poorer than LIPA or LDA as a foam stabilizer, comparing with the data in Tables 3 and 4.
EXAMPLE VIII Foam stability and resistance to grease with sodium lauryl sulfate as foaming agent.
Basic formula:
20.0% sodium lauryl sulfate 2.5% foam stabilizer 77.5% inerts in lauryl sulfate plus soft water Concentration 0.25%
Table 8 Foam stability Grease resistance-ML refined cotton seed oil ML oil Foam to form stabigrease lizer Ini film on tial min min. 10 glass ML ML ML The above data show that in a foaming composition using a concentrated solution of sodium lauryl sulfate as the detergent, the compounds of the invention were effective as foam stabilizers and in resistance to grease.
It is significant that in all of the comparisons given above, in every case except with the built formulations, in the presence of grease the foam stability with applicants novel composition continued a greater period than 15 minutes, even at high concentrations of oils, whereas with LIPA and LDA, there was no test in which this was attained.
Comparable results are obtainable using other Cl4'-C18 aliphatic carboxylic acids, such as those formed by the oxo process, however, the fatty acids are generally preferred due to their low cost and availability.
The improved foam stabilizers may be used in any desired proportions which may be effective for the purpose, depending on the foaming agent used, water hardness, and other factors. In general, from 0.1 to 20 parts of the ethoxylate may be used with from 5 to 60 parts of the anionic surface active agent in the formulation. The concentration of the formulation itself which is used will vary a great deal depending on the end use of the product.
The foregoing tests clearly demonstrate that a new series of compounds has been developed which have unusual foam stabilizing properties in the presence or absence of grease or oil and which impart improved detergency to anionic detergents. These compounds have excellent emulsifying properties as well. They may be used in cosmetic formulations such as shampoos, hair creams, and vanishing creams. They may also be used in solvent cleaners, dry cleaning and oil well drilling fluids. The solubility may be varied from 0ils0lublc using oleic acid amides, for example, to water-soluble by increasing the length of the ethoxy ether chain.
I claim:
1. As a new composition of matter an ethoxylated aliphatic carboxylic acid amide of isopropanolamine having the following structural formula where R=any aliphatic carboxylic acid radical having 13 or more carbon atoms in the chain and X=2 to 20 inclusive.
2. A foam stabilizer for anionic foaming detergent compositions comprising a Cl4-Cl8 aliphatic carboxylic acid isopropanolamide ethoxylate containing at least 2 111015 of ethylene oxide.
3. A foam stabilizer for anionic foaming detergent compositions which comprises a Cl4-Cl8 fatty acid isopropanolamide ethoxylate containing from 2 to 20 mols of ethylene oxide.
4. A foam stabilizer according to claim 2 wherein the fatty acid is selected from the class consisting of olcic, stearic, palmitic, myristic, linoleic and tall oil.
References Cited in the file of this patent UNITED STATES PATENTS 2,085,706 Schoeller et al. June 29, 1937 2,520,381 Carnes Aug. 29, 1950 2,677,700 Jackson et al. May 4, 1954 2,702,279 Funderburk et a1 Feb. 15, 1955 2,757,143 K-atzman July 31, 1956 2,881,204 Kirkpatrick Apr. 7, 1959
Claims (1)
1. AS A NEW COMPOSITION OF MATTER AN ETHOXYLATED ALIPHATIC CARBOXYLIC ACID AMIDE OF ISOPROPANOLAMINE HAVING THE FOLLOWING STRUCTURAL FORMULA
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US795608A US2991296A (en) | 1959-02-26 | 1959-02-26 | Method for improving foam stability of foaming detergent composition and improved stabilizers therefor |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US795608A US2991296A (en) | 1959-02-26 | 1959-02-26 | Method for improving foam stability of foaming detergent composition and improved stabilizers therefor |
Publications (1)
Publication Number | Publication Date |
---|---|
US2991296A true US2991296A (en) | 1961-07-04 |
Family
ID=25165989
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US795608A Expired - Lifetime US2991296A (en) | 1959-02-26 | 1959-02-26 | Method for improving foam stability of foaming detergent composition and improved stabilizers therefor |
Country Status (1)
Country | Link |
---|---|
US (1) | US2991296A (en) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3210286A (en) * | 1960-06-27 | 1965-10-05 | Colgate Palmolive Co | Liquid abrasive cleanser |
US4044033A (en) * | 1975-04-14 | 1977-08-23 | Milliken Research Corporation | High temperature lubricant |
FR2363324A1 (en) * | 1976-09-01 | 1978-03-31 | Henkel Kgaa | AQUEOUS OR HYDROALCOOLIC STABLE SOLUTIONS OF PERFUMED ESSENCES OR OIL SOLUBLE MEDICINAL PRODUCTS |
US5174927A (en) * | 1990-09-28 | 1992-12-29 | The Procter & Gamble Company | Process for preparing brightener-containing liquid detergent compositions with polyhydroxy fatty acid amines |
US5194639A (en) * | 1990-09-28 | 1993-03-16 | The Procter & Gamble Company | Preparation of polyhydroxy fatty acid amides in the presence of solvents |
US5223179A (en) * | 1992-03-26 | 1993-06-29 | The Procter & Gamble Company | Cleaning compositions with glycerol amides |
US5254281A (en) * | 1991-01-29 | 1993-10-19 | The Procter & Gamble Company | Soap bars with polyhydroxy fatty acid amides |
US5332528A (en) * | 1990-09-28 | 1994-07-26 | The Procter & Gamble Company | Polyhydroxy fatty acid amides in soil release agent-containing detergent compositions |
US5338487A (en) * | 1990-09-28 | 1994-08-16 | The Procter & Gamble Company | Catalyzed process for glucamide detergents |
US5338486A (en) * | 1990-09-28 | 1994-08-16 | The Procter & Gamble Company | High catalyst process for glucamide detergents |
US5354425A (en) * | 1993-12-13 | 1994-10-11 | The Procter & Gamble Company | Tissue paper treated with polyhydroxy fatty acid amide softener systems that are biodegradable |
US5380891A (en) * | 1990-09-28 | 1995-01-10 | The Procter & Gamble Company | Phase transfer assisted process for glucamide detergents |
US5449770A (en) * | 1992-01-14 | 1995-09-12 | The Procter & Gamble Company | Process for making N-alkylamino polyols |
US5454982A (en) * | 1990-09-28 | 1995-10-03 | The Procter & Gamble Company | Detergent composition containing polyhydroxy fatty acid amide and alkyl ester sulfonate surfactants |
US5625098A (en) * | 1991-07-26 | 1997-04-29 | The Procter & Gamble Company | Process for preparing N-alkyl polyhydroxyalkyl amines in aqueous/hydroxy solvents |
US5700771A (en) * | 1990-09-28 | 1997-12-23 | The Procter & Gamble Company | Polyhydroxy fatty acid amide surfactants in percarbonate bleach-containing compositions |
US5723673A (en) * | 1995-06-07 | 1998-03-03 | The Procter & Gamble Company | Process for preparing amides of N-alkyl polyhydroxyalkyls |
US5777165A (en) * | 1995-06-07 | 1998-07-07 | The Procter & Gamble Company | Process for preparing amides of N-alkyl polyhydroxyalkyl amines |
WO2002092740A1 (en) * | 2001-05-15 | 2002-11-21 | Ici Americas, Inc. | Mixed polyalkylene glycol hydroxyalkyl isostearamides as rheology adjuvants |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2085706A (en) * | 1930-11-29 | 1937-06-29 | Ig Farbenindustrie Ag | Derivatives of carboxylic acid amides |
US2520381A (en) * | 1946-06-18 | 1950-08-29 | American Cyanamid Co | Condensation of ethylene oxide with carboxylic acid amides |
US2677700A (en) * | 1951-05-31 | 1954-05-04 | Wyandotte Chemicals Corp | Polyoxyalkylene surface active agents |
US2702279A (en) * | 1955-02-15 | Detergent compositions having | ||
US2757143A (en) * | 1956-07-31 | Detergent composition | ||
US2881204A (en) * | 1953-02-13 | 1959-04-07 | Visco Products Co | Oxyalkylated hydroxy compounds |
-
1959
- 1959-02-26 US US795608A patent/US2991296A/en not_active Expired - Lifetime
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2702279A (en) * | 1955-02-15 | Detergent compositions having | ||
US2757143A (en) * | 1956-07-31 | Detergent composition | ||
US2085706A (en) * | 1930-11-29 | 1937-06-29 | Ig Farbenindustrie Ag | Derivatives of carboxylic acid amides |
US2520381A (en) * | 1946-06-18 | 1950-08-29 | American Cyanamid Co | Condensation of ethylene oxide with carboxylic acid amides |
US2677700A (en) * | 1951-05-31 | 1954-05-04 | Wyandotte Chemicals Corp | Polyoxyalkylene surface active agents |
US2881204A (en) * | 1953-02-13 | 1959-04-07 | Visco Products Co | Oxyalkylated hydroxy compounds |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3210286A (en) * | 1960-06-27 | 1965-10-05 | Colgate Palmolive Co | Liquid abrasive cleanser |
US4044033A (en) * | 1975-04-14 | 1977-08-23 | Milliken Research Corporation | High temperature lubricant |
FR2363324A1 (en) * | 1976-09-01 | 1978-03-31 | Henkel Kgaa | AQUEOUS OR HYDROALCOOLIC STABLE SOLUTIONS OF PERFUMED ESSENCES OR OIL SOLUBLE MEDICINAL PRODUCTS |
US5338486A (en) * | 1990-09-28 | 1994-08-16 | The Procter & Gamble Company | High catalyst process for glucamide detergents |
US5194639A (en) * | 1990-09-28 | 1993-03-16 | The Procter & Gamble Company | Preparation of polyhydroxy fatty acid amides in the presence of solvents |
US5174927A (en) * | 1990-09-28 | 1992-12-29 | The Procter & Gamble Company | Process for preparing brightener-containing liquid detergent compositions with polyhydroxy fatty acid amines |
US5332528A (en) * | 1990-09-28 | 1994-07-26 | The Procter & Gamble Company | Polyhydroxy fatty acid amides in soil release agent-containing detergent compositions |
US5338487A (en) * | 1990-09-28 | 1994-08-16 | The Procter & Gamble Company | Catalyzed process for glucamide detergents |
US5700771A (en) * | 1990-09-28 | 1997-12-23 | The Procter & Gamble Company | Polyhydroxy fatty acid amide surfactants in percarbonate bleach-containing compositions |
US5380891A (en) * | 1990-09-28 | 1995-01-10 | The Procter & Gamble Company | Phase transfer assisted process for glucamide detergents |
US5454982A (en) * | 1990-09-28 | 1995-10-03 | The Procter & Gamble Company | Detergent composition containing polyhydroxy fatty acid amide and alkyl ester sulfonate surfactants |
US5254281A (en) * | 1991-01-29 | 1993-10-19 | The Procter & Gamble Company | Soap bars with polyhydroxy fatty acid amides |
US5625098A (en) * | 1991-07-26 | 1997-04-29 | The Procter & Gamble Company | Process for preparing N-alkyl polyhydroxyalkyl amines in aqueous/hydroxy solvents |
US5449770A (en) * | 1992-01-14 | 1995-09-12 | The Procter & Gamble Company | Process for making N-alkylamino polyols |
US5223179A (en) * | 1992-03-26 | 1993-06-29 | The Procter & Gamble Company | Cleaning compositions with glycerol amides |
US5354425A (en) * | 1993-12-13 | 1994-10-11 | The Procter & Gamble Company | Tissue paper treated with polyhydroxy fatty acid amide softener systems that are biodegradable |
US5723673A (en) * | 1995-06-07 | 1998-03-03 | The Procter & Gamble Company | Process for preparing amides of N-alkyl polyhydroxyalkyls |
US5777165A (en) * | 1995-06-07 | 1998-07-07 | The Procter & Gamble Company | Process for preparing amides of N-alkyl polyhydroxyalkyl amines |
WO2002092740A1 (en) * | 2001-05-15 | 2002-11-21 | Ici Americas, Inc. | Mixed polyalkylene glycol hydroxyalkyl isostearamides as rheology adjuvants |
US6635607B2 (en) | 2001-05-15 | 2003-10-21 | Ici Americas Inc. | Mixed polyalkylene glycol hydroxyalkyl isostearamides as rheology adjuvants |
KR100887861B1 (en) * | 2001-05-15 | 2009-03-06 | 크로다 유니케마 아이엔씨. | Mixed polyalkylene glycol hydroxyalkyl isostearamides as rheology adjuvants |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2991296A (en) | Method for improving foam stability of foaming detergent composition and improved stabilizers therefor | |
US5656586A (en) | Amphoteric surfactants having multiple hydrophobic and hydrophilic groups | |
US3280179A (en) | Processes for producing acyclic surfactant sulfobetaines | |
US5972875A (en) | Low-foaming amine oxide surfactant concentrate and method of manufacture | |
JP4823430B2 (en) | Surfactant composition | |
JPH05507073A (en) | Quaternized esters obtained from alkanolamines and fatty acids and their use as recovery agents | |
JPH0635595B2 (en) | Light detergent composition | |
US3663459A (en) | Detergent bar | |
JPH07509740A (en) | foaming detergent mixture | |
JPH0640846A (en) | Lactobionic acid amide composition, detergent, cleaning agent and/or cleaner and additive consisting of them for adjusting agent for making-up and preparation of said composition | |
MX2008013369A (en) | Composition which contains a mixture of mono-, di-, and triglycerides and glycerine. | |
Lif et al. | Nonionic surfactants containing an amide group | |
US5922659A (en) | Cleanser composition | |
EP0038862A1 (en) | Compositions containing amido amine salts, and their use as fabric softeners | |
US6531443B2 (en) | Alkanolamides | |
US2704280A (en) | Long-chain aliphatic ether-amides in detergent compositions | |
US6207629B1 (en) | Concentrated aqueous betaine-type surfactant compositions and process for their preparation | |
JP5576121B2 (en) | Compound | |
EP1062310B1 (en) | Improved alkanolamides | |
EP0386826B2 (en) | Amidated fatty acid mixtures and use thereof as thickeners | |
US3723356A (en) | Combinations of hydroxyalkyl-n-methyltaurines and anionic sufactants as synergistic emulsifiers | |
JPH0333197A (en) | Detergent compound | |
CA2129937C (en) | Process for the preparation of highly concentrated free-flowing aqueous solutions of betaines | |
US4528128A (en) | Detergent compositions | |
US4057506A (en) | Heavy-duty liquid detergent |