US2712530A - Sulfonate detergent blend - Google Patents
Sulfonate detergent blend Download PDFInfo
- Publication number
- US2712530A US2712530A US153309A US15330950A US2712530A US 2712530 A US2712530 A US 2712530A US 153309 A US153309 A US 153309A US 15330950 A US15330950 A US 15330950A US 2712530 A US2712530 A US 2712530A
- Authority
- US
- United States
- Prior art keywords
- sulfonate
- blend
- detergent
- straight
- chain
- 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 36
- 239000003599 detergent Substances 0.000 title claims description 22
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title description 25
- -1 SULFONATE COMPOUND Chemical class 0.000 claims description 6
- 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 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000002689 soil Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- PGVOXXHNGYYHHB-UHFFFAOYSA-N dodecan-3-ylbenzene Chemical compound CCCCCCCCCC(CC)C1=CC=CC=C1 PGVOXXHNGYYHHB-UHFFFAOYSA-N 0.000 description 4
- 239000008233 hard water Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- VRPRIAVYSREHAN-UHFFFAOYSA-N dodecan-2-ylbenzene Chemical compound CCCCCCCCCCC(C)C1=CC=CC=C1 VRPRIAVYSREHAN-UHFFFAOYSA-N 0.000 description 2
- RHDHXBLZBVAPTL-UHFFFAOYSA-N dodecan-4-ylbenzene Chemical compound CCCCCCCCC(CCC)C1=CC=CC=C1 RHDHXBLZBVAPTL-UHFFFAOYSA-N 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- VZZMNLVGDGMQQV-UHFFFAOYSA-N tridecan-3-ylbenzene Chemical compound CCCCCCCCCCC(CC)C1=CC=CC=C1 VZZMNLVGDGMQQV-UHFFFAOYSA-N 0.000 description 2
- NVHBFHMWJJMQTG-UHFFFAOYSA-N undecan-3-ylbenzene Chemical compound CCCCCCCCC(CC)C1=CC=CC=C1 NVHBFHMWJJMQTG-UHFFFAOYSA-N 0.000 description 2
- NSQAXMRLBNXEHK-UHFFFAOYSA-N undecan-4-ylbenzene Chemical compound CCCCCCCC(CCC)C1=CC=CC=C1 NSQAXMRLBNXEHK-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- XBEADGFTLHRJRB-UHFFFAOYSA-N undecylbenzene Chemical compound CCCCCCCCCCCC1=CC=CC=C1 XBEADGFTLHRJRB-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type 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
- 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 invention relates to a novel detergent composition. More particularly the invention is concerned with a detergent comprising as active ingredients a blend of alkyl aryl sulfonates.
- Alkyl aryl sulfonates prepared by the alkylation of an aromatic nucleus with branched-chain olefins (such as obtained by polymerizing low molecular weight olefins, e. g. propylene) and subsequent sultonation of the alkylate are now established as good detergents for general purposes.
- these compounds possess only mediocre detersivc properties at low concentrations (less than 0.25%
- R is a branched-chain alkyl radical of 9 to 18 carbon atoms and M is an alkali metal with 2.5 to 50 weight per cent or preferably, 5 to 50 Weight per cent, based on the total sulfonate blend, of a straight-chain secondary alkyl aryl sulfonate of the formula:
- R is a straight-chain alkyl radical of l5 carbon atoms
- R" is a straight-chain alkyl radical of 8-14 carbon atoms Where the sum of R and R" is 9-15
- M is an alkali metal.
- the straight-chain secondary alkyl benzenes are prepared according to well-known chemical reactions.
- the sulfonates are prepared by reaction of the alkyl aryl hydrocarbons with S03, mixtures ofSOs and S02, chlorosulfonic acid, fuming sulfuric acid, etc. followed by neutralization'with the alkali whose sulfonate .is desired.
- a detergent composition consisting essentially of a sulfonate compound (A) of the formula:
- R is a branched-chain alkyl radical of 9-18 carbon atoms and M is an alkali metal, and 2.5 to 50 wt. based on the total sulfonate blend, of asulfonate compound (B) of the formula:
- a detergent composition consisting essentially sodium ciz-polypropylbenzene sulfonate and 2.5 to weight per cent, based on the total sulfonate blend, the sodium sulfonate' of Z-phenyldodecane.
- a detergent composition consisting essentially of sodium cia-polypropylbenzene sulfonate and 2.5 to 50 weight per cent, based on the total sulfonate blend, of the sodium sulfonate of 4-phenylundecane.
- a detergent composition consisting essentially sodium Ciz-polypropylbenzene sulfonate and 2.5 to weight per cent, based on the total sulfonate blend, the sodium sulfonate of 3-phenylundecane.
- a detergent composition consisting essentially sodium Crz-polypropylbenzene sulfonate and 2.5 to weight per cent, based on thetotal sulfonate .blend, the sodium sulfonate of 3-phenyldodecane.
- a detergent composition consisting essentially sodium Ciz-polypropylbenzene sulfonate and 2.5 to weight per cent, based on the total sulfonate blend, the sodium sulfonate of 3-phenyltridecane.
- a detergent composition consisting essentially a mixture of a sulfonate compound of the formula of 50 of of 50 of of 50 of alkali metal salt of a sulfonated 2-phenyl 'alkane, in
- the alkane portion is a straight chain normal alkane containing from 10 to 16 carbon atoms, the sulfonatedphenyl alkane being present in an amount from about 5% to about 50% by Weight of said mixture.
- An aqueous solution of a detergent mixture consisting essentially of a detergent sulfonate (A) of the SOzM where R is a branched-chain alkyl radical of 9-18 carbon atoms, R" is a straight-chain alkyl radical of 8-14 carbon atoms and M is an alkali metal, and 2.5 to 50 weight atoms, where the sum of carbon atoms in R and R is per cent, based on the total detergent sulfonate, of a de- 915, and M is an alkali metal, the detergent mixture tergent sulfonate (B) of the formula: being present in the aqueous solution in a detersive 5 amount of up to about 0.25 gm. per 100 ml.
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
United States Patent SULFONATE DETERGENT. BLEND Frederick Neil Bauingaitner, (Iranfor-d, N. 3., assignor to Essa Research and Engineering (Iernpany, a corporation of Delaware No Drawing. Application March 31, 195%), Serial No. 153,309
8 Claims. (Ci. 2521o1) The invention relates to a novel detergent composition. More particularly the invention is concerned with a detergent comprising as active ingredients a blend of alkyl aryl sulfonates.
Alkyl aryl sulfonates prepared by the alkylation of an aromatic nucleus with branched-chain olefins (such as obtained by polymerizing low molecular weight olefins, e. g. propylene) and subsequent sultonation of the alkylate are now established as good detergents for general purposes. However, these compounds possess only mediocre detersivc properties at low concentrations (less than 0.25%
It is the purpose of this invention to prepare a detergent having good detersive properties at low concentrations.
It is also an object of this invention to modify the detersive activity of a branched-chain alkyl aryl sulfonate to confer upon it good detersive properties at low concentrations.
It has been found that a superior detergent is prepared by blendin a detergent sulfonate of the type:
where R is a branched-chain alkyl radical of 9 to 18 carbon atoms and M is an alkali metal with 2.5 to 50 weight per cent or preferably, 5 to 50 Weight per cent, based on the total sulfonate blend, of a straight-chain secondary alkyl aryl sulfonate of the formula:
where R is a straight-chain alkyl radical of l5 carbon atoms, R" is a straight-chain alkyl radical of 8-14 carbon atoms Where the sum of R and R" is 9-15, and M is an alkali metal. The detersive power of the resulting blend of sulfonates is substantially superior at low concentrations (up to 0.25 grn./ 100 ml.) to that of the branchedchain detergent or the straight-chain detergent alone, and greater than the additive effect of both compounds.
Launder-Oineter data on the synergistic effect of typical blends are given in Table I. in the table data are given for a typical dodecylbenzene suifonate prepared by alkylating benzene with a Gig-branched olefin (prepared by polymerizing propylene) and thereafter sulronating the alkylate and neutralizing, as indicated by compound D. The presence of weight per cent of a straight-chain secondary alkyl aryl sulfonate, compositions E, F, G, H, etc., in a blend with 75 weight per cent of D produces an unexpectedly large rise in detergency over that of D at concentrations below 3.2 gm./ 100 ml. At the same time the presence of these substances does not materially alter the detersive power of D at higher concentrations. It is also to be noted that blends of D with a branched-chain secondary alkyl aryl sulfonate possess no advantage over D alone and are exceedingly poor in hard waters (Blend N, Table I).
TABLE I Launder-Ometer data [Runs made on active mixtures using United States Testing Co. cloth] Soil Removal 1 240 p. p. in. Hard Water, Conc. I 1 .15 2 .35 .5
1 A B O A B C A B O A A D, 0 2 polypropyl benzene sulfonate 1O 40 85 130 110 Blend Composition75% of D and 25% Sodium Sulronate of:
E, 2-Phenyldodecane 75 10 65 115 25 90 105 90 105 F, S-Phenyhmdecme..- 60 5 85 25 90 60 95 90 G, 3-Phenyldodecane 80 10 70 110 30 E0 125 100 110 H, 3-Phenyltridecane 25 45 110 50 60 110 100 I. 4'Phenylundecane 4D 5 35 80 2O 60 45 115 J 4Phenyldodecane 25 10 15 65 25 40 100 50 K 4-Phenyltr1decane 35 10 25 55 35 20 8O 60 100 85 L, 5-Phenyldodecaue... 2O 5 15 50 15 35 80 40 95 95 M, fi-Phenyldodecane 50 5 45 80 15 65 40 110 95 N, 2-Methyl-5-phenylundecane 0 15 S5 110 115 O, Dodecylbenzene 3 35 25 10 95 50 45 100 90 110 90 P, Tetradecylbenzene 4 40 5 35 65 15 F 75 4O 95 100 A, Measured soil removal-Launder-Ometer Method.
B, Expected soil removal-Oa1culated from soil removal values for the individual components. 0, DifterenceMeasured soil removal minus expected soil removal.
1 Soil removal relative to Dreit at 0.5% in 240 p. p. in. hard water as 100.
Concentration expressed as g/100 nil-40% active ingredients.
5* Prepared by alkylating benzene with l-dodecene (mixture of isomers).
4 Prepared by alkylating benzene with 1-tetradecene (nurture of isomers).
'3 Thesame synergistic eifect is also noted when as little as 2.5% of the straight-chain secondary alkyl aryl sulfonate is used as shown in the following Table II.
TABLE H Lazmder-Ometer data where R is a straight-chain alkyl radical of 15 carbon atoms, R" is a straight-chain alkyl radical of 8-14 carbon [Runs made on 40% active mixtures using United States Testing 00. cloth] Soil Removal 1 240 P. P. M. Hard Water, Cone Blend GompositionActive Ingredients .1 .15 2 .35 5
- Percent Ci; Percent 2- Polypropylben- Phenyldodeo- A B C. A B O A B C A A zene Sulfonate ane Sultanate 100 l0 40 85 130 110 97. 2. 5 50 40 75 40 35 105 80 100 90 95 5 70 10 60 125 90 120 70 110 100 90 10 5 60 120 35 85 120 50 115 95 85 15 80 5 7 110 30 80 115 65 50 110 105 25 75 10 65 115 25 90 105 50 55 90 105 65 35 90 p 10 100 15 3O 60 85 85 50 50 80 10 70 85 5 80 105 25 80 85 80 A, Measured soil rerimval-Launder-Ometer Method.
l Soil removal relative to drett at 0.5% in 240 Concentration expressed as g./100 ml.-40% active ingredients.
The straight-chain secondary alkyl benzenes are prepared according to well-known chemical reactions. One
' Friedel-Crafts type catalyst.
The sulfonates are prepared by reaction of the alkyl aryl hydrocarbons with S03, mixtures ofSOs and S02, chlorosulfonic acid, fuming sulfuric acid, etc. followed by neutralization'with the alkali whose sulfonate .is desired.
The reactions by which the components of the synergistic mixtures of this invention are prepared are well known in the art and form no part of this invention. It will also be understood that the recital of consisting essentially of leaves the appended claims open for the inclusion of unspecified ingredients which do not materially afiect the basic and novel characteristics of the claimed compositions. V V
Having described the invention in a manner such that it may be followed by one skilled in the art, what is claimed is:
. 1. A detergent composition consisting essentially of a sulfonate compound (A) of the formula:
soar/1 where R is a branched-chain alkyl radical of 9-18 carbon atoms and M is an alkali metal, and 2.5 to 50 wt. based on the total sulfonate blend, of asulfonate compound (B) of the formula:
SOaM
p. p. m. hard water as 100.
atoms, where the sum of the carbon atoms in R and R is 915, and M-is an alkali metal.
2. A detergent composition consisting essentially sodium ciz-polypropylbenzene sulfonate and 2.5 to weight per cent, based on the total sulfonate blend, the sodium sulfonate' of Z-phenyldodecane.
3. A detergent composition consisting essentially of sodium cia-polypropylbenzene sulfonate and 2.5 to 50 weight per cent, based on the total sulfonate blend, of the sodium sulfonate of 4-phenylundecane.
4. A detergent composition consisting essentially sodium Ciz-polypropylbenzene sulfonate and 2.5 to weight per cent, based on the total sulfonate blend, the sodium sulfonate of 3-phenylundecane.
5. A detergent composition consisting essentially sodium Crz-polypropylbenzene sulfonate and 2.5 to weight per cent, based on thetotal sulfonate .blend, the sodium sulfonate of 3-phenyldodecane.
6. A detergent composition consisting essentially sodium Ciz-polypropylbenzene sulfonate and 2.5 to weight per cent, based on the total sulfonate blend, the sodium sulfonate of 3-phenyltridecane.
7. A detergent composition consisting essentially a mixture of a sulfonate compound of the formula of 50 of of 50 of of 50 of alkali metal salt of a sulfonated 2-phenyl 'alkane, in
which the alkane portion is a straight chain normal alkane containing from 10 to 16 carbon atoms, the sulfonatedphenyl alkane being present in an amount from about 5% to about 50% by Weight of said mixture.
8. An aqueous solution of a detergent mixture consisting essentially of a detergent sulfonate (A) of the SOzM where R is a branched-chain alkyl radical of 9-18 carbon atoms, R" is a straight-chain alkyl radical of 8-14 carbon atoms and M is an alkali metal, and 2.5 to 50 weight atoms, where the sum of carbon atoms in R and R is per cent, based on the total detergent sulfonate, of a de- 915, and M is an alkali metal, the detergent mixture tergent sulfonate (B) of the formula: being present in the aqueous solution in a detersive 5 amount of up to about 0.25 gm. per 100 ml.
References Cited in the file of this patent 803M UNITED STATES PATENTS 10 2,232,118 Kyrides Feb. 18, 1941 a a Where R is a straight-chain alkyl radical of 1-5 carbon 477 383 Lewls July 26 1949
Claims (1)
1. A DETERGENT COMPOSITION CONSISTING ESSENTIALLY OF A SULFONATE COMPOUND (A) OF THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US153309A US2712530A (en) | 1950-03-31 | 1950-03-31 | Sulfonate detergent blend |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US153309A US2712530A (en) | 1950-03-31 | 1950-03-31 | Sulfonate detergent blend |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2712530A true US2712530A (en) | 1955-07-05 |
Family
ID=22546649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US153309A Expired - Lifetime US2712530A (en) | 1950-03-31 | 1950-03-31 | Sulfonate detergent blend |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2712530A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2944028A (en) * | 1956-09-12 | 1960-07-05 | California Research Corp | Sulfonate detergent compositions |
| US2956025A (en) * | 1955-03-22 | 1960-10-11 | California Research Corp | Sulfonate detergent compositions with improved foam characteristics |
| US3248443A (en) * | 1963-01-31 | 1966-04-26 | Monsanto Co | Process for alkylating aromatic hydrocarbons |
| US3320174A (en) * | 1964-04-20 | 1967-05-16 | Colgate Palmolive Co | Detergent composition |
| US3370100A (en) * | 1963-06-19 | 1968-02-20 | Monsanto Co | Detergent alkylate compositions |
| US3440171A (en) * | 1964-06-29 | 1969-04-22 | Union Carbide Corp | Surface active compositions |
| US3655572A (en) * | 1970-01-21 | 1972-04-11 | Chevron Res | Water-containing dry cleaning compositions |
| US3926862A (en) * | 1973-04-16 | 1975-12-16 | Allied Chem | Detergent solvent compositions |
| DE2803420A1 (en) * | 1977-01-28 | 1978-08-31 | Exxon Research Engineering Co | IMPROVED ALKYLATES AND SULPHONIC ACIDS, AND SULPHONATES MANUFACTURED THEREFORE |
| US4235810A (en) * | 1978-08-03 | 1980-11-25 | Exxon Research & Engineering Co. | Alkylates and sulphonic acids and sulphonates produced therefrom |
| US4259193A (en) * | 1977-08-04 | 1981-03-31 | Exxon Research & Engineering Co. | Overbased sulphonates |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2232118A (en) * | 1939-06-05 | 1941-02-18 | Monsanto Chemicals | Alkyl substituted benzene sulphonic acids and salts |
| US2477383A (en) * | 1946-12-26 | 1949-07-26 | California Research Corp | Sulfonated detergent and its method of preparation |
-
1950
- 1950-03-31 US US153309A patent/US2712530A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2232118A (en) * | 1939-06-05 | 1941-02-18 | Monsanto Chemicals | Alkyl substituted benzene sulphonic acids and salts |
| US2477383A (en) * | 1946-12-26 | 1949-07-26 | California Research Corp | Sulfonated detergent and its method of preparation |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956025A (en) * | 1955-03-22 | 1960-10-11 | California Research Corp | Sulfonate detergent compositions with improved foam characteristics |
| US2944028A (en) * | 1956-09-12 | 1960-07-05 | California Research Corp | Sulfonate detergent compositions |
| US3248443A (en) * | 1963-01-31 | 1966-04-26 | Monsanto Co | Process for alkylating aromatic hydrocarbons |
| US3370100A (en) * | 1963-06-19 | 1968-02-20 | Monsanto Co | Detergent alkylate compositions |
| US3320174A (en) * | 1964-04-20 | 1967-05-16 | Colgate Palmolive Co | Detergent composition |
| US3440171A (en) * | 1964-06-29 | 1969-04-22 | Union Carbide Corp | Surface active compositions |
| US3655572A (en) * | 1970-01-21 | 1972-04-11 | Chevron Res | Water-containing dry cleaning compositions |
| US3926862A (en) * | 1973-04-16 | 1975-12-16 | Allied Chem | Detergent solvent compositions |
| DE2803420A1 (en) * | 1977-01-28 | 1978-08-31 | Exxon Research Engineering Co | IMPROVED ALKYLATES AND SULPHONIC ACIDS, AND SULPHONATES MANUFACTURED THEREFORE |
| US4259193A (en) * | 1977-08-04 | 1981-03-31 | Exxon Research & Engineering Co. | Overbased sulphonates |
| US4235810A (en) * | 1978-08-03 | 1980-11-25 | Exxon Research & Engineering Co. | Alkylates and sulphonic acids and sulphonates produced therefrom |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| USRE27096E (en) | Best available copy | |
| US4052342A (en) | Secondary alkyl sulfate: alcohol ethoxylate mixtures | |
| US2712530A (en) | Sulfonate detergent blend | |
| CA1110517A (en) | Liquid detergent composition | |
| US2469493A (en) | Synthetic detergent composition | |
| US3487023A (en) | Detergent compositions of sulfonated secondary phenyl-substituted n-alkanes | |
| US8158819B2 (en) | Process to obtain a highly soluble linear alkylbenzene sulfonate | |
| US3769243A (en) | Linear alkylbenzene sulfonate detergent compositions | |
| US3766254A (en) | Linear alkylphenol disulfonate phosphate free detergent actives | |
| US4129526A (en) | Granular detergent compositions and a process for producing same | |
| US2768956A (en) | Detergent compositions | |
| US3836484A (en) | Phosphate-free detergent concentrates containing sulfated and sulfonated linear alkylphenols | |
| US2978416A (en) | Concentrated aqueous detergent composition | |
| US4067818A (en) | Dust laying | |
| US3544475A (en) | Detergent compositions based on mixtures of alpha-olefin sulfonates and dimer olefin sulfonates | |
| US3980588A (en) | Detergents containing olefin sulfonate | |
| US2738365A (en) | Process of producing a synthetic detergent of good color | |
| US3867317A (en) | Synthetic detergent bars containing calcium olefin sulfonates | |
| US2630411A (en) | Surface active alkyl benzene sulfonate composition | |
| US2694086A (en) | Sulfonation of poly-alkyl substituted aromatic hydrocarbons | |
| US3042713A (en) | Alkyl aromatic sulfonic acid | |
| US3296146A (en) | Alkylbenzene sulfonate detergent compositions containing 2-hydroxy-1-amino alkanes | |
| US2832743A (en) | Free flowing alkyl aryl sulfonate detergent compositions | |
| US3442811A (en) | Heavy duty detergent compositions | |
| US2709686A (en) | Non-caking detergent compositions |