US3001948A - Synthetic detergent bar - Google Patents
Synthetic detergent bar Download PDFInfo
- Publication number
- US3001948A US3001948A US700250A US70025057A US3001948A US 3001948 A US3001948 A US 3001948A US 700250 A US700250 A US 700250A US 70025057 A US70025057 A US 70025057A US 3001948 A US3001948 A US 3001948A
- Authority
- US
- United States
- Prior art keywords
- bar
- detergent
- metal
- sulfonate
- ammonium
- 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
- 239000000271 synthetic detergent Substances 0.000 title claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 238000012935 Averaging Methods 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 1
- 239000003599 detergent Substances 0.000 description 28
- 239000000463 material Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- -1 for example Inorganic materials 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 150000003871 sulfonates Chemical class 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 8
- 239000000344 soap Substances 0.000 description 7
- 150000008052 alkyl sulfonates Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 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 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000012169 petroleum derived wax Substances 0.000 description 3
- 235000019381 petroleum wax Nutrition 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- PSFDQSOCUJVVGF-UHFFFAOYSA-N harman Chemical compound C12=CC=CC=C2NC2=C1C=CN=C2C PSFDQSOCUJVVGF-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000008054 sulfonate salts Chemical class 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000003109 Karl Fischer titration Methods 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
- 229920002472 Starch Polymers 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- DIOLOCSXUMYFJN-UHFFFAOYSA-N calcium;azane Chemical compound N.[Ca+2] DIOLOCSXUMYFJN-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012956 testing procedure 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
- C11D1/02—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
Definitions
- the present invention relates to molded or shaped synthetic detergent compositions of any desired shape or form and to a process for the preparation thereof. More particularly, the invention has to do with the preparation of a detergent bar for toilet and bath use containing as the essential detergent material a special kind of synthetic surfactant, the particles of which can unexpectedly be compacted or pressed into a lastingly sturdy mass or body.
- detergent bar compositions based on normally plastic synthetic detergent material of ammonium detergent .salts of alkylsulfonic acids, and, in association therewith, a second metal detergent salt of alkylsulfonic' acids,- the valkyl groups in both instances being primary'straightchainradicals of about 8, preferably 10, to 20 carbon atoms, the detergent material having an average carbon content of 12 to 16 carbon atoms.
- the com- .position contains water in an amount bya weight, based on the detergent material, of about 1 to 10%, usually around 5 to 8%.
- ammonium n-alkylsulfonates of a broader class can satisfactorily'be solidified, milled and molded into an effective detergent bar by the incorporation with the ammonium n-alkylsulfonate mixture of a second metal n-alkylsulfonate detergent salt material, the alkyl groups again being primary straightchain radicals of 8 to 20 carbon atoms averaging'1'2 to 16 carbon atoms in the molecule.
- the metal salt sulfonates can be 'derived from a number of metals, including the alkali metals, for example, sodium and potassium; the alkaline earth metals, e.g., barium, calcium and magnesium;.an other metal material, e.g., aluminum.
- an amount of second metal n-alkylsulfonate detergent salt is selected within about the range of 10 to 15 mol percent'to mol percent and higher based on total sulfonate content.
- the amount will depend on the sulfonate selected.
- slightly higher amounts near the top limit of the range can be selected, that is, around 75 mol percent, while with the polyvalent metal sulfonates lesser amounts will be satisfactory, that is, below about 50 mol percent. In most cases, a satisfactory mixture will consist of around.50 mol percent of theammonium n alkylsulfonate.
- the inorganic sulfate e.g., ammonium or sodium sulfate
- the inorganic sulfate e.g., ammonium or sodium sulfate
- a convenient source of the olefins for preparing the sulfonates contemplated by the invention are those that can be derived from the cracking of petroleum wax to yield a mixture primarily of l-olefins having from about 8 to 20 carbon atoms in the molecule. It is the sulfonates of these olefins which can be blended, if necessary, to yield the desired alkylsulfonates having an average carbon content of 12 to 16 carbon atoms.
- the sulfonates contemplated by the invention are primarily and essentially those derived from 1- olefins of the specified carbon content, and are essentially of normal or straight-chain structure, although, as is known in the art, a small degree of branching may be permitted without substantial impairment of the detersive action of the material.
- characterization of the anionic portion of the sulfonate as being a primary straight-chain radical means that the sulfonate is derived essentially from normal l-olefins in which a scattering of unsaturation in the molecule and a tolerable degree of chain branching may exist in the mixture of compounds 3 bar are subjective or organoleptic in nature and are based largely on experience derived from the properties possessed by the conventional soap bar.
- the over-all nature of the bar such as waxy appearance and color
- the hardness of a bar can satisfactorily be determined by As an example of the invention, calcium-ammonium the use of the conventional grease testing procedure as alkylsulfonates are prepared from a mixture of alphadescribed in ASTM method D-217.
- the hardness of a olefins of about 8 to 20 carbon atoms and obtained by bar can thus be measured by the depth that a standard the cracking of petroleum wax, the average carbon concone penetrates the sample, set at a temperature of 77 tent of the olefins being around 15. In the preparation ;F., expressed in tenths of a millimeter.
- non-soap detergent bars are Alkylsulfonate (calcium alkylsulfonate to ammoni superior to soap in the respect that solubllity and rates um alkylsmfonate mol ratio 10.90) 821 of solution are better in both hard and salt water.
- a convenient way of measuring the solubility oh Water, wt. percent 6.9 aractenstics of detergent bar is by determining its loss Hardness 6.0 in weight in grams per hand-wash employing ordinary Wear rate Awash 12 tap water having a hardness of 50 p.p.m.
- the alkylsulfonate salts are now in condition for molding. If desired, at this stage there may be incorporated into the detergent material other ingredients for the purposes of improving the composition in such properties as odor, color and the like. Accordingly, known fillers, perfumes, dyes and the like can be incorporated With the A bar is formed from ammonium and potassium primary n-alkylsulfonates derived from C -C cracked wax olefins. It analyzes as follows:
- Alkylsulfonate (ammonium alkylsulfonate to potassium sulfonates, mol ratio 15:85) 78 Sulfate content 15 Water, wt. percent 5.0 Hardness 7.0 Wear rate, g./wash 1.5
- a satisfactory bar is prepared from ammonium and magnesium sulfonate, with the following characteristics:
- N-alkylsulfonate (ammonium n-alkylsulfonate to magnesium n-alkylsulfonate, mol ratio 2:1) 74 Sulfate content 15 Water, wt percent 8 Wear rate, g./wash 1.1
- .ondary sulfonates are unsatisfactory and cannot be formed into a bar.
- other synthetic detergent materials such as those which form the great bulk of .commercialdetergent compositions, namely, the alkylaryl sulfonates and the alkyl sulfates cannot satisfactorily be formed into bars in accordance with the present invenassists 5 tion.
- the alkyl sulfates are chemically unstable and hydrolyze readily in the presence of water, while the alkylaryl sulfonates on the other hand are too soluble and give a sticky feeling when employed in the form of a bar.
- a synthetic detergent bar consisting essentially of (l) ammonium n-alkyl sulfonate; (2) a second metal nalkyl sulfonate to enable milling and molding in an amount of 10 to 75 weight percent based on (1) and (2); and (3) 1% to 10% water, by weight, based on 1) and (2); the alkyl groups in each of (1) and (2) being primary straight-chain radicals of about 8 to 20 carbon atoms and averaging 12 to 16 carbon atoms, the metal of said second metal n-alkyl sulfonate being selected from the group consisting of alkali and alkaline earth metals.
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE573302D BE573302A (zh) | 1957-11-26 | ||
| US700250A US3001948A (en) | 1957-11-26 | 1957-11-26 | Synthetic detergent bar |
| FR779428A FR1215339A (fr) | 1957-11-26 | 1958-11-18 | Compositions détergentes synthétiques moulables |
| GB37762/58A GB861052A (en) | 1957-11-26 | 1958-11-24 | Moulded synthetic detergent compositions |
| GB27139/60A GB890696A (en) | 1957-11-26 | 1958-11-24 | Moulded synthetic detergent compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US700250A US3001948A (en) | 1957-11-26 | 1957-11-26 | Synthetic detergent bar |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3001948A true US3001948A (en) | 1961-09-26 |
Family
ID=24812778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US700250A Expired - Lifetime US3001948A (en) | 1957-11-26 | 1957-11-26 | Synthetic detergent bar |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3001948A (zh) |
| BE (1) | BE573302A (zh) |
| FR (1) | FR1215339A (zh) |
| GB (2) | GB890696A (zh) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3172859A (en) * | 1965-03-09 | Betergent briquette | ||
| US3175978A (en) * | 1962-06-01 | 1965-03-30 | California Research Corp | Light duty liquid detergent |
| US3175977A (en) * | 1965-03-30 | Liquid eetekgent compositions | ||
| US3186948A (en) * | 1961-02-27 | 1965-06-01 | California Research Corp | Detergent toilet bars |
| US3291744A (en) * | 1959-10-26 | 1966-12-13 | Colgate Palmolive Co | Detergent bar |
| US3622517A (en) * | 1968-03-06 | 1971-11-23 | Marathon Oil Co | Synthetic detergent compositions |
| US3989647A (en) * | 1973-04-26 | 1976-11-02 | Lever Brothers Company | Quick lathering toilet bars and method of making same |
| US4007125A (en) * | 1973-12-26 | 1977-02-08 | Lever Brothers Company | Synthetic detergent bar |
| US4092260A (en) * | 1973-11-28 | 1978-05-30 | Lever Bros. Co. | Quick lathering toilet bars and method of making same |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE611781A (zh) * | 1960-12-23 | |||
| US4058487A (en) | 1973-11-28 | 1977-11-15 | Lever Brothers Co. | Quick lathering toilet bars and method of making same |
| US4058490A (en) | 1973-11-28 | 1977-11-15 | Lever Brothers Company | Quick lathering toilet bars and method of making same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2374187A (en) * | 1945-04-24 | Detergent composition | ||
| US2504411A (en) * | 1948-03-19 | 1950-04-18 | Shell Dev | Preparation of alkyl sulfonates |
| GB682207A (en) * | 1949-03-21 | 1952-11-05 | Bataafsche Petroleum | Process for producing sulphonates from bisulphites and olefins and the sulphonates so produced |
| US2813078A (en) * | 1954-09-10 | 1957-11-12 | American Cyanamid Co | Cake detergent and method for its production |
-
0
- BE BE573302D patent/BE573302A/xx unknown
-
1957
- 1957-11-26 US US700250A patent/US3001948A/en not_active Expired - Lifetime
-
1958
- 1958-11-18 FR FR779428A patent/FR1215339A/fr not_active Expired
- 1958-11-24 GB GB27139/60A patent/GB890696A/en not_active Expired
- 1958-11-24 GB GB37762/58A patent/GB861052A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2374187A (en) * | 1945-04-24 | Detergent composition | ||
| US2504411A (en) * | 1948-03-19 | 1950-04-18 | Shell Dev | Preparation of alkyl sulfonates |
| GB682207A (en) * | 1949-03-21 | 1952-11-05 | Bataafsche Petroleum | Process for producing sulphonates from bisulphites and olefins and the sulphonates so produced |
| US2813078A (en) * | 1954-09-10 | 1957-11-12 | American Cyanamid Co | Cake detergent and method for its production |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3172859A (en) * | 1965-03-09 | Betergent briquette | ||
| US3175977A (en) * | 1965-03-30 | Liquid eetekgent compositions | ||
| US3291744A (en) * | 1959-10-26 | 1966-12-13 | Colgate Palmolive Co | Detergent bar |
| US3186948A (en) * | 1961-02-27 | 1965-06-01 | California Research Corp | Detergent toilet bars |
| US3175978A (en) * | 1962-06-01 | 1965-03-30 | California Research Corp | Light duty liquid detergent |
| US3622517A (en) * | 1968-03-06 | 1971-11-23 | Marathon Oil Co | Synthetic detergent compositions |
| US3989647A (en) * | 1973-04-26 | 1976-11-02 | Lever Brothers Company | Quick lathering toilet bars and method of making same |
| US4092260A (en) * | 1973-11-28 | 1978-05-30 | Lever Bros. Co. | Quick lathering toilet bars and method of making same |
| US4096082A (en) * | 1973-11-28 | 1978-06-20 | Lever Brothers Company | Quick lathering toilet bars and method of making same |
| US4110239A (en) * | 1973-11-28 | 1978-08-29 | Lever Bros. Co. | Quick lathering toilet bars and method of making same |
| US4007125A (en) * | 1973-12-26 | 1977-02-08 | Lever Brothers Company | Synthetic detergent bar |
Also Published As
| Publication number | Publication date |
|---|---|
| GB861052A (en) | 1961-02-15 |
| FR1215339A (fr) | 1960-04-15 |
| GB890696A (en) | 1962-03-07 |
| BE573302A (zh) |
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