US3764569A - Detergent composition - Google Patents
Detergent composition Download PDFInfo
- Publication number
- US3764569A US3764569A US00169505A US3764569DA US3764569A US 3764569 A US3764569 A US 3764569A US 00169505 A US00169505 A US 00169505A US 3764569D A US3764569D A US 3764569DA US 3764569 A US3764569 A US 3764569A
- Authority
- US
- United States
- Prior art keywords
- alkylsulfonate
- weight
- primary
- parts
- linear
- 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 abstract description 22
- 239000003599 detergent Substances 0.000 title abstract description 17
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 25
- 150000008052 alkyl sulfonates Chemical group 0.000 claims abstract description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000005227 alkyl sulfonate group Chemical group 0.000 claims description 5
- 239000003752 hydrotrope Substances 0.000 abstract description 13
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 abstract description 6
- 238000009472 formulation Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 12
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 3
- 101000756346 Homo sapiens RE1-silencing transcription factor Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 102100022940 RE1-silencing transcription factor Human genes 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007822 coupling agent 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
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical class CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940048842 sodium xylenesulfonate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 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
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- 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
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3409—Alkyl -, alkenyl -, cycloalkyl - or terpene sulfates or sulfonates
Definitions
- Hydrotropes are salts which effect substantially greater solubility of slightly soluble substances than does water at the same temperature. This behavior is the opposite of the common salting out effect following the addition of many electrolytes to aqueous solutions of numerous solutes.
- hydrotropes salts are the alkali or alkaline earth salts of the sulfonates of toluene, xylene.
- the most generally used hydrotrope in detergents is sodium xylenesulfonate because it is inexpensive and effective as a solvating agent.
- hydrotrope in detergents In the manufacture of heavy duty detergent powders they reduce the viscosity of the slurry before spray drying. In heavy duty liquid detergents they may act as solubilizers and coupling agents or even as cloud point depressants.
- heptyl and octyl sulfonates can act as hydrotropes in detergent compositions when from 3 to 9 weight percent thereof are incorporated in such compositions.
- the subject secondary alkyl sulfonates can be prepared by a sulfoxidation reaction disclosed and claimed in commonly assigned copending patent application Serial No. 40,740 filed on May 26, 1970.
- the primary alkylsulfonates can be prepared by a bisulfite reaction involving reacting the l-olefin or 1- olefins with aqueous bisulfite in a mutual solvent under basic conditions at relatively low temperatures in the presence of an oxygen-containing initiator. This reaction is disclosed and claimed in commonly assigned copending application Serial No. 47,485 filed June 18, 1970.
- Viscosity measurements given below show that by incorporating 5 percent C and C alkylsulfonates, the viscosity of a 25 percent dodecylbenzene sulfonate solution (Nacconol NRSF) is reduced.
- Table A The solubilizing properties were determined by (Table A) measuring the solubility of a given C -C primary alkylsulfonate sample, as well as on blends of this sample and the hydrotrope under investigation. In determining the solubility, sufficient water was added so that only little solids remained un dissolved. The carbon number distribution of the C C primary alkylsulfonate is shown in Table B. These compounds have optimum detergency.
- a suitable range of detergent constituents employing the hydrotropes of this invention comprises.
- More specific detergent formulations are the following (Na salts): (in parts by weight) A B C D Active Matter (eg LAS) 25 25 25 25 C Primary alkylsulphonate 5 C Primary 5 C, Secondary 5 C Secondary 5 A suitable method for determining whether the described hydrotropes are biodegradable is not available.
- the Soap and Detergent Association method of analysis is insensitive to C,C,. and other short chain alkylsul- A fonate. However, as the alkyl chains are linear, the compounds are probably biodegradable.
- a detergent composition consisting of about 3 to 9 weight percent of a C or C linear alkylsulfonate as a hydrotrope, from 15 to 30 weight percent of linear alkylsulfonate detergent having 11 to 19 carbon atoms in the alkyl moiety, up to 5 wt. percent of a fatty acid alkylolamide foam stabilizer and the balance water.
- composition according to claim 1 containing about 5 parts by weight of a C primary alkylsulfonate and about 25 parts by weight of a linear alkylsulfonate having a carbon content in the C C range.
- a composition according to claim 1 containing about 5 parts by weight of a C secondary alkylsulfonate and about 25 parts by weight of a linear alkylsulfonate having a carbon content in the C, C range.
- a composition according to claim 1 containing about 5 parts by weight of a C secondary alkylsulfonate and about 25 parts by weight of a linear alkylsulfonate having a carbon content in the C -C range.
- a composition according to claim 1 containing about 5 parts by weight of a C primary alkylsulfonate and about 25 parts by weight of a linear alkylsulfonate having a carbon content in the C C, range.
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16950571A | 1971-08-05 | 1971-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3764569A true US3764569A (en) | 1973-10-09 |
Family
ID=22615980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00169505A Expired - Lifetime US3764569A (en) | 1971-08-05 | 1971-08-05 | Detergent composition |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3764569A (fr) |
| JP (1) | JPS4828505A (fr) |
| BE (1) | BE787231A (fr) |
| CA (1) | CA976449A (fr) |
| DE (1) | DE2238307A1 (fr) |
| FR (1) | FR2148120B1 (fr) |
| GB (1) | GB1352793A (fr) |
| IT (1) | IT972168B (fr) |
| NL (1) | NL7210495A (fr) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147673A (en) * | 1975-04-11 | 1979-04-03 | S.A. Texaco Belgium N.V. | Detergent composition containing sulfinyl dipropionic acids |
| US4444573A (en) * | 1982-06-21 | 1984-04-24 | Nalco Chemical Company | Hydrotropes and uses thereof |
| US4454074A (en) * | 1982-09-20 | 1984-06-12 | Texaco Inc. | Salts of dicyclopentadiene sulfonate and method of preparing |
| US5213705A (en) * | 1985-04-30 | 1993-05-25 | Ecolab Inc. | Encapsulated halogen bleaches and methods of preparation and use |
| US5478503A (en) * | 1994-02-28 | 1995-12-26 | The Procter & Gamble Company | Process for making a granular detergent composition containing succinate hydrotrope and having improved solubility in cold temperature laundering solutions |
| US5478502A (en) * | 1994-02-28 | 1995-12-26 | The Procter & Gamble Company | Granular detergent composition containing hydrotropes and optimum levels of anoionic surfactants for improved solubility in cold temperature laundering solutions |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH071124B2 (ja) * | 1988-02-02 | 1995-01-11 | 三洋電機株式会社 | 燃焼装置 |
| FR2714674B1 (fr) * | 1994-01-06 | 1996-03-15 | Stepan Europe | Agents hydrotropes et compositions les contenant. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3011977A (en) * | 1956-07-23 | 1961-12-05 | Henkel & Compagnie G M B H | Detergent composition |
| US3393154A (en) * | 1965-10-23 | 1968-07-16 | Colgate Palmolive Co | Pearlescent liquid detergent compositions |
| US3496224A (en) * | 1966-09-13 | 1970-02-17 | Union Oil Co | Purification of sulfonic acids |
-
0
- BE BE787231D patent/BE787231A/fr unknown
-
1971
- 1971-08-05 US US00169505A patent/US3764569A/en not_active Expired - Lifetime
-
1972
- 1972-07-21 GB GB3412772A patent/GB1352793A/en not_active Expired
- 1972-07-21 JP JP47072650A patent/JPS4828505A/ja active Pending
- 1972-07-31 NL NL7210495A patent/NL7210495A/xx unknown
- 1972-07-31 FR FR7227546A patent/FR2148120B1/fr not_active Expired
- 1972-08-02 IT IT27802/72A patent/IT972168B/it active
- 1972-08-03 DE DE2238307A patent/DE2238307A1/de active Pending
- 1972-08-03 CA CA148,696A patent/CA976449A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3011977A (en) * | 1956-07-23 | 1961-12-05 | Henkel & Compagnie G M B H | Detergent composition |
| US3393154A (en) * | 1965-10-23 | 1968-07-16 | Colgate Palmolive Co | Pearlescent liquid detergent compositions |
| US3496224A (en) * | 1966-09-13 | 1970-02-17 | Union Oil Co | Purification of sulfonic acids |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147673A (en) * | 1975-04-11 | 1979-04-03 | S.A. Texaco Belgium N.V. | Detergent composition containing sulfinyl dipropionic acids |
| US4444573A (en) * | 1982-06-21 | 1984-04-24 | Nalco Chemical Company | Hydrotropes and uses thereof |
| US4454074A (en) * | 1982-09-20 | 1984-06-12 | Texaco Inc. | Salts of dicyclopentadiene sulfonate and method of preparing |
| US5213705A (en) * | 1985-04-30 | 1993-05-25 | Ecolab Inc. | Encapsulated halogen bleaches and methods of preparation and use |
| US5478503A (en) * | 1994-02-28 | 1995-12-26 | The Procter & Gamble Company | Process for making a granular detergent composition containing succinate hydrotrope and having improved solubility in cold temperature laundering solutions |
| US5478502A (en) * | 1994-02-28 | 1995-12-26 | The Procter & Gamble Company | Granular detergent composition containing hydrotropes and optimum levels of anoionic surfactants for improved solubility in cold temperature laundering solutions |
Also Published As
| Publication number | Publication date |
|---|---|
| CA976449A (en) | 1975-10-21 |
| NL7210495A (fr) | 1973-02-07 |
| GB1352793A (en) | 1974-05-08 |
| IT972168B (it) | 1974-05-20 |
| JPS4828505A (fr) | 1973-04-16 |
| BE787231A (fr) | 1973-02-05 |
| FR2148120B1 (fr) | 1976-01-23 |
| DE2238307A1 (de) | 1973-02-15 |
| FR2148120A1 (fr) | 1973-03-11 |
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