US2469493A - Synthetic detergent composition - Google Patents
Synthetic detergent composition Download PDFInfo
- Publication number
- US2469493A US2469493A US758717A US75871747A US2469493A US 2469493 A US2469493 A US 2469493A US 758717 A US758717 A US 758717A US 75871747 A US75871747 A US 75871747A US 2469493 A US2469493 A US 2469493A
- Authority
- US
- United States
- Prior art keywords
- detergent
- detergent composition
- ester
- average
- synthetic
- 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 description 35
- 239000000271 synthetic detergent Substances 0.000 title description 13
- 150000002148 esters Chemical class 0.000 description 23
- 239000003599 detergent Substances 0.000 description 21
- -1 polyoxyethylene Polymers 0.000 description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 11
- 125000006353 oxyethylene group Chemical group 0.000 description 9
- 239000003784 tall oil Substances 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 5
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 5
- 239000003350 kerosene Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000001236 detergent effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000008233 hard water Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 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
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 101150008094 per1 gene Proteins 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
Definitions
- the present invention relates to a synthetic detergent composition.
- An object of the invention is to provide an improved synthetic detergent composition for general application.
- a specific object of the invention is to provide a synthetic detergent composition that is particularly eifective for washing cotton fabrics.
- Synthetic detergents are considered, at the present time, to include all of the non-soap products of synthetic chemistry which have valuable detergent properties. These may be broadly classified into cationic, anionic, and non-ionic detergents.
- the principal members of the anionic class are the organic sulfates or sulfonates, usually employed in the form of their alkali salts.
- the non-ionic detergents are exemplified by the polyoxyethylene derivatives of lipophilic organic materials. These synthetic detergents have the advantage over soap that they retain their activity to a greater extent in the presence of calcium and magnesium ions which are found in hard water. While the synthetic detergents as a group are all useful materials, each of the several types embraced in the class has certain disadvantages.
- alkylaryl sulfonates which are prepared by condensing an aliphatic hydrocarbon with 9 to 16 carbon atoms and benzene or naphthalene, and thereafter sulfonating the product. These compositions are generally used in the form of their alkali neutralized salts.
- One of the most readily available compositions of this type is produced by alkylatingbenzene with the mixture of hydrocarbons found in a petroleum distillate of the kerosene type, and thereafter sulfonating and neutralizing the product. While this material has certain valuable detergent characteristics, there are several properties that impose limitations on its usefulness.
- the material has limited water solubility which means that if aqueous solutions are desired, it is necessary to operate within certain concentrations. Solubility is further reduced in hard water. There is also a tendency for these alkylaryl sulfonates to separate from water on cooling and to be difflcult to redissolve. There is a further l mitation in that the detergent effect of the alkylaryl sulfonates on cotton is relatively poor.
- non-ionic synthetic detergents have the disadvantages that they are relatively more expensive and do not produce foam or suds to the extent of soap or most of the ionic type synthetic detergents. While the production of suds is not an actual criterion of detergent eiilciency, the reaction of users of synthetic detergents, particularly for household use,
- the combination of a specific group of alkylaryl sulfonates and a specific group of poiyoxyethylene esters produces a synthetic detergent which has a wider range of usefulness than either of the components, and which exhibits an unexpected improvement in detergency on cotton fabrics.
- the advantages of this combination are found within a relatively narrow range of compounds.
- the alkylaryl sulfontes, which are useful in the invention are those in which the alkyl group contains from 9 to 16 carbon atoms, and the aryl group is benzene or naphthalene.
- the alkylaryl base of the detergent is advantageously composed of the mixture produced by alkylating benzene with the hydrocarbons found in kerosene.
- the poiyoxyethylene ester useful in the combination is a polyoxyethylene ester of tall oil or rosin, wherein the esters contain an average of from 12 to 30 oxyethylene groups per earboxyl group.
- These polyoxyethylene esters are preferably produced by the reaction of ethylene oxide and tall oil or rosin in proportions to produce esters containing an average of from 12 to 30 oxyethylene groups per molecule of the carboxylic acid.
- Esters of similar type can be produced by esterifying polyethylene glycols, having an average of 12 to 30 oxyethylene groups with tall oil or rosin in proportions to produce preponderantly mono-esters.
- composition of the invention may be prepared in any one of several ways depending upon the characteristics, other than detergency, desired.
- an aqueous solution may be prepared which contains the non-ionic detergent and the alkylaryl sulfonate in the desired proportions
- the nonionic detergent and alkylaryl sulfonate may be mixed with inorganic salt or alkali in the proportions best suited to the particular application.
- the two detergents' may be dissolved in water and spray dried or drum dried, or the two detergents may be mixed dry.
- aqueous solutions were prepared by a ding the necessary quantityof water to the det rgent components and warming the mixture on a steam bath and stirring occasionally until dissolved.
- the non-aqueous preparations 3 were made by dry mixing the several ingredents.
- Percent detergent mix ture refers to the relation of parts of the ionic or non-ionic detergent to the total parts in the preparations, automobile wa's'hing L lnpounds,
- compositions of the invention can be made from single alkylaryl sulfonates of the class defined and single polyoxyethylene esters of the class defined.
- the compositions can be, and preferably are, made with mixed alkylaryl sulfonates and mixed polyoxyethylene esters of the classes defined.
- Additives of various types in addition to those listed in the examples can be included in the compositions or used with them to obtain some particular property, as is well understood in the detergent art. Thus, thickeners, coloring agents, perfumes, builders, solvents, etc., can be employed if desired for their known effects.
- compositions of the invention are useful as laundry and household detergents, shampoo mixture of the two, the relation being expressed 5 concentration.
- a detergent composition comprising a mixsalts, etc. ture consisting of from 5 to 95% by weight of a,
- a detergent composition as defined in claim 1 wherein the said alkyl substituted aromatic hydrocarbon is a mixture of alkyl benzenes wherein the alkyl groups have the carbon chain lengths of the mixed hydrocarbons of kerosene.
- a detergent composition comprising a mixture consisting of from 60 to 85% by weight of a sodium sulfonate of a mixture of alkyl benzenes wherein the alkyl groups have the carbon chain lengths of the mixed hydrocarbons of kerosene, and 40 to 15% of a-polyoxyethylene ester of tall oil containing an average of 12 to 30 oxyethylene groups per carboxyl group. 5 g
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
Patented May 10, 1949 SYNTHETIC DETERGENT COMPOSITION George E. Barker, Pleasant Hills, Del., minor to Atlas Powder Company, Wilmington, Del., a
corporation of Delaware No Drawing. Application July 2, 1947, Serial No. 758,717
Claims. (Cl. 252-461) The present invention relates to a synthetic detergent composition.
An object of the invention is to provide an improved synthetic detergent composition for general application.
A specific object of the invention is to provide a synthetic detergent composition that is particularly eifective for washing cotton fabrics.
The above and other objects will become apparent in the course of the following description.
Synthetic detergents are considered, at the present time, to include all of the non-soap products of synthetic chemistry which have valuable detergent properties. These may be broadly classified into cationic, anionic, and non-ionic detergents. The principal members of the anionic class are the organic sulfates or sulfonates, usually employed in the form of their alkali salts. The non-ionic detergents are exemplified by the polyoxyethylene derivatives of lipophilic organic materials. These synthetic detergents have the advantage over soap that they retain their activity to a greater extent in the presence of calcium and magnesium ions which are found in hard water. While the synthetic detergents as a group are all useful materials, each of the several types embraced in the class has certain disadvantages. One of the most useful and cheapest types of the anionic group of synthetic detergents is the series of alkylaryl sulfonates which are prepared by condensing an aliphatic hydrocarbon with 9 to 16 carbon atoms and benzene or naphthalene, and thereafter sulfonating the product. These compositions are generally used in the form of their alkali neutralized salts. One of the most readily available compositions of this type is produced by alkylatingbenzene with the mixture of hydrocarbons found in a petroleum distillate of the kerosene type, and thereafter sulfonating and neutralizing the product. While this material has certain valuable detergent characteristics, there are several properties that impose limitations on its usefulness. The material has limited water solubility which means that if aqueous solutions are desired, it is necessary to operate within certain concentrations. Solubility is further reduced in hard water. There is also a tendency for these alkylaryl sulfonates to separate from water on cooling and to be difflcult to redissolve. There is a further l mitation in that the detergent effect of the alkylaryl sulfonates on cotton is relatively poor.
On the other hand, the non-ionic synthetic detergents have the disadvantages that they are relatively more expensive and do not produce foam or suds to the extent of soap or most of the ionic type synthetic detergents. While the production of suds is not an actual criterion of detergent eiilciency, the reaction of users of synthetic detergents, particularly for household use,
is unfavorable toward materials that do not produce suds.
In accordance with the present invention, it has been found that the combination of a specific group of alkylaryl sulfonates and a specific group of poiyoxyethylene esters produces a synthetic detergent which has a wider range of usefulness than either of the components, and which exhibits an unexpected improvement in detergency on cotton fabrics. The advantages of this combination are found within a relatively narrow range of compounds. The alkylaryl sulfontes, which are useful in the invention, are those in which the alkyl group contains from 9 to 16 carbon atoms, and the aryl group is benzene or naphthalene. The alkylaryl base of the detergentis advantageously composed of the mixture produced by alkylating benzene with the hydrocarbons found in kerosene. The poiyoxyethylene ester useful in the combination is a polyoxyethylene ester of tall oil or rosin, wherein the esters contain an average of from 12 to 30 oxyethylene groups per earboxyl group. These polyoxyethylene esters are preferably produced by the reaction of ethylene oxide and tall oil or rosin in proportions to produce esters containing an average of from 12 to 30 oxyethylene groups per molecule of the carboxylic acid. Esters of similar type can be produced by esterifying polyethylene glycols, having an average of 12 to 30 oxyethylene groups with tall oil or rosin in proportions to produce preponderantly mono-esters.
Many of the advantages of the invention can be realized in mixtures containin from 5 to 95 g per cent of the alkylaryl sulfonate and 95 to 5 per cent of the polyoxyethylene ester. The prepercent of the alkylaryl sulfonate, and 40 to 15 per cent of the poiyoxyethylene ester.
The composition of the invention may be prepared in any one of several ways depending upon the characteristics, other than detergency, desired. For example, an aqueous solution may be prepared which contains the non-ionic detergent and the alkylaryl sulfonate in the desired proportions, If a powder is desired, the nonionic detergent and alkylaryl sulfonate may be mixed with inorganic salt or alkali in the proportions best suited to the particular application. In preparing the latter type of mixture, the two detergents' may be dissolved in water and spray dried or drum dried, or the two detergents may be mixed dry.
The following examples illustrate several specific compositions made in accordance with the inventirm. The aqueous solutions were prepared by a ding the necessary quantityof water to the det rgent components and warming the mixture on a steam bath and stirring occasionally until dissolved. The non-aqueous preparations 3 were made by dry mixing the several ingredents. In the table; the heading "Percent detergent mix ture refers to the relation of parts of the ionic or non-ionic detergent to the total parts in the preparations, automobile wa's'hing L lnpounds,
,dry mixtures, or
positions can be prepared for use in the form of aqueous solutions 7 or suitable By way of example of the improved detergency of the compositions oiv the invention, the following results were obtained in a launderometer, using a standard soiled cotton in which the soil was an aqueous emulsion of mineral oil and carbon black. In reporting Relative detergency,.the results with the sodium alkylaryl sulfonate alone were taken as standards at 100%.
Composition, Per Cent Conceiitraw Poiyoxyethylene Relatn e g i ester of tall oil, g fi ggg Deter- Water 8 a g average 20 (300 gency g g oxyethyiene groups per 1) carboxyl Par cent Per1 6(8)"! 86 14 25 97. 0 2. 5 0. 108 83. 5 14 2. 5 0. 25 138 83. 5 l6. 5 0 0. 25 100 83. 5 0 16. 5 0. 25 120 In this tabulation it is to be noted that the addition of 14 parts-0f the alkylaryl sulfonate and 2.5 parts of the polyoxyethylene ester gives a detergent effect which is outstandingly superior to that obtained with either component alone.
The compositions of the invention can be made from single alkylaryl sulfonates of the class defined and single polyoxyethylene esters of the class defined. The compositions can be, and preferably are, made with mixed alkylaryl sulfonates and mixed polyoxyethylene esters of the classes defined. Additives of various types in addition to those listed in the examples can be included in the compositions or used with them to obtain some particular property, as is well understood in the detergent art. Thus, thickeners, coloring agents, perfumes, builders, solvents, etc., can be employed if desired for their known effects.
The compositions of the invention are useful as laundry and household detergents, shampoo mixture of the two, the relation being expressed 5 concentration.
as parts of one detergent per 100 parts of the What is claimed is:
mixture and ignoring additives such as wate -1. A detergent composition comprising a mixsalts, etc. ture consisting of from 5 to 95% by weight of a,
- Percent 1 1 Percent Example Ionic Parts detergent Non-Ionic Iarts deter ent Otheringredients Parts mixture mix 1 Sodium alkyl benzene 16 80 Poiyoxyethylene. ester of 4 20 Water an sulionates, elk 1 tall oil, average 16 oxygroups have cha ethylene groups. per lengthsgf kerosene carboxyl group.
drocar ons.
2 .310... 14 84.9 Polyoxyethylene ester of 2.5 15,1 (In tall oil, average 20 oxyethylene groups per carboxyi group. v
3 d 14 84.9 Polyoxyethy ene ester of 2.5 15.1 do 33 5 rosin, average 20 oxyethylene groups per carboxyl group. i 75 83% Poiyoxyethylene ester of 15 16% Sodium s lfat 10 tail oil, average 10 oxyethylene groups per carboxyl group. 1 75 .do 10 25 do 60 10 33% Polyoxyethylene ester of 20 66% Sodium Sulfate and 10 tall oil, average 20 oxy- Soda Ash. 1 60 ethylene groups per earboxyl group. 7 do 10 33% 0 20 66% SodiumCai-boxymethy] 1 Cellglose i atcr 'get- 9 raso ium yrop osphate. 65
V sulfonate of alkyl substituted aromatic hydrocarbon selected from the class consisting of benzene and naphthalene, and wherein the alkyl group has from 9 to 16 carbon'atoms; and from 95 to 5% of polyoxyethylene ester of organic acid -material selected from the class consisting of rosin and tall oil, said ester containing an average of from 12 to 30 oxyethylene groups per carboxyl group.
' 2. A detergent composition as defined in claim 1 wherein the mixture consists of from 60 to by weight of said sulfonate and from 40 to 15% of said polyoxyethylene ester.
3. A detergent composition as defined in claim 1 wherein the said alkyl substituted aromatic hydrocarbon is a mixture of alkyl benzenes wherein the alkyl groups have the carbon chain lengths of the mixed hydrocarbons of kerosene.
4. A detergent composition comprising a mixture consisting of from 60 to 85% by weight of a sodium sulfonate of a mixture of alkyl benzenes wherein the alkyl groups have the carbon chain lengths of the mixed hydrocarbons of kerosene, and 40 to 15% of a-polyoxyethylene ester of tall oil containing an average of 12 to 30 oxyethylene groups per carboxyl group. 5 g
5. A detergent composition as defined in claim 4 wherein the said polyoxyethylene ester contains an average of about 20 oxyethylene groups per carboxyl group.
GEORGE E. BARKER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US758717A US2469493A (en) | 1947-07-02 | 1947-07-02 | Synthetic detergent composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US758717A US2469493A (en) | 1947-07-02 | 1947-07-02 | Synthetic detergent composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2469493A true US2469493A (en) | 1949-05-10 |
Family
ID=25052803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US758717A Expired - Lifetime US2469493A (en) | 1947-07-02 | 1947-07-02 | Synthetic detergent composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2469493A (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2572805A (en) * | 1951-10-23 | Detergent composition | ||
| US2586767A (en) * | 1948-01-31 | 1952-02-19 | Monsanto Chemicals | Method for producing alkylene oxide condensation products |
| US2588318A (en) * | 1949-02-07 | 1952-03-04 | Monsanto Chemicals | Water emulsifiable soil-poison concentrate |
| US2588970A (en) * | 1949-10-17 | 1952-03-11 | Hollingshead Corp | Hydraulic fluid composition |
| US2610966A (en) * | 1949-10-17 | 1952-09-16 | Hollingshead Corp | Process for treating tall oil with alkylene oxides |
| US2662898A (en) * | 1949-09-20 | 1953-12-15 | Colgate Palmolive Peet Co | Alkanol-ether-imides of long-chain aliphatic dicarboxylic compounds |
| US2666017A (en) * | 1950-07-14 | 1954-01-12 | Monsanto Chemicals | Nutrient media containing antifoaming agents |
| US2712994A (en) * | 1949-01-27 | 1955-07-12 | Monsanto Chemicals | Process for improving paper and product |
| DE931768C (en) * | 1950-12-23 | 1955-08-16 | Basf Ag | Process for the production of detergents and wetting agents through the action of ethylene oxide on non-uniform technical mixtures of oxaethylatable substances |
| US2744888A (en) * | 1950-08-04 | 1956-05-08 | American Cyanamid Co | Ethenoxy n-monoethanolamides of tall oil |
| US2751358A (en) * | 1949-11-28 | 1956-06-19 | Shell Dev | Non-foaming detergents |
| US2778814A (en) * | 1957-01-22 | Alkyl aryl sulfonic acid amine salt | ||
| US2816924A (en) * | 1955-11-15 | 1957-12-17 | American Cyanamid Co | Process for arylamides |
| US2855367A (en) * | 1954-09-07 | 1958-10-07 | Colgate Palmolive Co | Detergent composition |
| US3029205A (en) * | 1958-05-05 | 1962-04-10 | Lever Brothers Ltd | Light duty liquid detergent |
| US3166444A (en) * | 1962-04-26 | 1965-01-19 | Lubrizol Corp | Method for cleaning metal articles |
| US3351559A (en) * | 1963-11-13 | 1967-11-07 | Henkel & Cie Gmbh | Pourable and free-flowing detergent, wetting, and emulsifying compositions |
| US4492646A (en) * | 1980-02-05 | 1985-01-08 | The Procter & Gamble Company | Liquid dishwashing detergent containing anionic surfactant, suds stabilizer and highly ethoxylated nonionic drainage promotor |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
| US2085706A (en) * | 1930-11-29 | 1937-06-29 | Ig Farbenindustrie Ag | Derivatives of carboxylic acid amides |
| US2283199A (en) * | 1936-07-30 | 1942-05-19 | Allied Chem & Dye Corp | Detergent |
| US2307058A (en) * | 1937-06-08 | 1943-01-05 | Moeller August | Breaking agent for emulsions |
-
1947
- 1947-07-02 US US758717A patent/US2469493A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
| US2085706A (en) * | 1930-11-29 | 1937-06-29 | Ig Farbenindustrie Ag | Derivatives of carboxylic acid amides |
| US2283199A (en) * | 1936-07-30 | 1942-05-19 | Allied Chem & Dye Corp | Detergent |
| US2307058A (en) * | 1937-06-08 | 1943-01-05 | Moeller August | Breaking agent for emulsions |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2778814A (en) * | 1957-01-22 | Alkyl aryl sulfonic acid amine salt | ||
| US2572805A (en) * | 1951-10-23 | Detergent composition | ||
| US2586767A (en) * | 1948-01-31 | 1952-02-19 | Monsanto Chemicals | Method for producing alkylene oxide condensation products |
| US2712994A (en) * | 1949-01-27 | 1955-07-12 | Monsanto Chemicals | Process for improving paper and product |
| US2588318A (en) * | 1949-02-07 | 1952-03-04 | Monsanto Chemicals | Water emulsifiable soil-poison concentrate |
| US2662898A (en) * | 1949-09-20 | 1953-12-15 | Colgate Palmolive Peet Co | Alkanol-ether-imides of long-chain aliphatic dicarboxylic compounds |
| US2588970A (en) * | 1949-10-17 | 1952-03-11 | Hollingshead Corp | Hydraulic fluid composition |
| US2610966A (en) * | 1949-10-17 | 1952-09-16 | Hollingshead Corp | Process for treating tall oil with alkylene oxides |
| US2751358A (en) * | 1949-11-28 | 1956-06-19 | Shell Dev | Non-foaming detergents |
| US2666017A (en) * | 1950-07-14 | 1954-01-12 | Monsanto Chemicals | Nutrient media containing antifoaming agents |
| US2744888A (en) * | 1950-08-04 | 1956-05-08 | American Cyanamid Co | Ethenoxy n-monoethanolamides of tall oil |
| DE931768C (en) * | 1950-12-23 | 1955-08-16 | Basf Ag | Process for the production of detergents and wetting agents through the action of ethylene oxide on non-uniform technical mixtures of oxaethylatable substances |
| US2855367A (en) * | 1954-09-07 | 1958-10-07 | Colgate Palmolive Co | Detergent composition |
| US2816924A (en) * | 1955-11-15 | 1957-12-17 | American Cyanamid Co | Process for arylamides |
| US3029205A (en) * | 1958-05-05 | 1962-04-10 | Lever Brothers Ltd | Light duty liquid detergent |
| US3166444A (en) * | 1962-04-26 | 1965-01-19 | Lubrizol Corp | Method for cleaning metal articles |
| US3351559A (en) * | 1963-11-13 | 1967-11-07 | Henkel & Cie Gmbh | Pourable and free-flowing detergent, wetting, and emulsifying compositions |
| US4492646A (en) * | 1980-02-05 | 1985-01-08 | The Procter & Gamble Company | Liquid dishwashing detergent containing anionic surfactant, suds stabilizer and highly ethoxylated nonionic drainage promotor |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2469493A (en) | Synthetic detergent composition | |
| US3709838A (en) | Liquid detergent compositions | |
| USRE22548E (en) | Preparation of aliphatic-aromatic | |
| US2679482A (en) | Synthetic detergent compositions | |
| US2383738A (en) | Detergent composition | |
| US2908651A (en) | Liquid detergent composition | |
| US3506580A (en) | Heat-treatment of sulfonated olefin products | |
| US3344174A (en) | Vicinal acylamido sulfonate compounds | |
| US2809937A (en) | Germicidal detergent composition | |
| US2653913A (en) | Synthetic detergent cakes | |
| US2383740A (en) | Detergent composition | |
| US2746932A (en) | Synthetic detergent compositions | |
| US2712530A (en) | Sulfonate detergent blend | |
| US3766254A (en) | Linear alkylphenol disulfonate phosphate free detergent actives | |
| US3836484A (en) | Phosphate-free detergent concentrates containing sulfated and sulfonated linear alkylphenols | |
| US2390295A (en) | Soap composition | |
| US2746931A (en) | Synthetic detergent compositions | |
| EP0011715B1 (en) | Liquid, cold-stable two-component washing agent and washing process | |
| US2642400A (en) | Surface-active composition | |
| US2347336A (en) | Detergent composition | |
| US2294075A (en) | Detergent composition | |
| US3980588A (en) | Detergents containing olefin sulfonate | |
| US3023168A (en) | Heavy duty liquid detergent | |
| US2738365A (en) | Process of producing a synthetic detergent of good color | |
| US3005777A (en) | Manufacture of surface-active compositions |