US3867316A - Process for the manufacture of flowable pasty detergents capable of being pumped - Google Patents
Process for the manufacture of flowable pasty detergents capable of being pumped Download PDFInfo
- Publication number
- US3867316A US3867316A US250085A US25008572A US3867316A US 3867316 A US3867316 A US 3867316A US 250085 A US250085 A US 250085A US 25008572 A US25008572 A US 25008572A US 3867316 A US3867316 A US 3867316A
- Authority
- US
- United States
- Prior art keywords
- sulfonic acids
- continuous flow
- sulfuric acid
- esters
- flow mixer
- 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
- 239000003599 detergent Substances 0.000 title claims abstract description 16
- 230000009969 flowable effect Effects 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 235000011837 pasties Nutrition 0.000 title abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 150000003460 sulfonic acids Chemical class 0.000 claims abstract description 12
- 239000013543 active substance Substances 0.000 claims abstract description 9
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 8
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 9
- 150000002191 fatty alcohols Chemical class 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- -1 OLEFIN SULFONIC ACIDS Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 238000005406 washing Methods 0.000 abstract description 8
- 239000003513 alkali Substances 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 239000003755 preservative agent Substances 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000007872 degassing Methods 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 101100165798 Arabidopsis thaliana CYP86A1 gene Proteins 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
Images
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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
Definitions
- ABSTRACT Flowable pasty raw materials for detergents capable of being pumped and having a content of washing active substance of more than 60% are obtained by neutralizing organic sulfuric acid semi-esters or sulfonic acids with alkalies. Before neutralization the sulfuric acid semi-esters or sulfonic acids are degassed and neutralization is carried out in a continuous flow mixer. The greater proportion of the mixture is conducted in a cycle whereas a smaller proportion is withdrawn as finished product. In the continuous flow mixer the usual buffer substances and preserving agents may be added to the products.
- the present invention relates to a process for the manufacture of flowable pasty detergents capable of being pumped by neutralizing with alkalies sulfuric acid semi-esters or sulfonic acids, which pasty detergents have a high content of washing active substances, especially more than 60 of washing active substance.
- organic sulfuric acid semi-esters or sulfonic acids there are to be understood semi-esters of 5 like, are introduced through further metering devices fatty alcohols and of hydroxy-ethers of fatty alcohols and alkylarylsulfonic acids and olefin-sulfonic acids as well as the product mixtures obtained in the olefin sulfonation which are known as anionic constituents of raw materials for detergents.
- the stiff consistency of the pastes is a result of the high air and electrolyte content originating from the manufacturing conditions.
- the air content can be reduced by prolonged storage, however to a limited extent only.
- To prepare pastes having a low content of electrolyte it is necessary to neutralize the organic sulfuric acid semi-esters or sulfonic acids in small quantities with careful control. This procedure considerably increases the price of the products.
- the present invention provides a process for the manufacture of pasty detergents containing a high pro portion of washing active substance and capable of being pumped by neutralization of organic sulfuric acid semi-esters or sulfonic acids with alkalies which comprises degassing the organic sulfuric acid semi-esters or sulfonic acids before they are neutralized, mixing them with the alkali and optionally other additives in a continuous flow mixer and thereby neutralizing them, after the mixture has left the continuous flow mixer withdrawing a smaller proportion thereof as finished product and recycling the larger proportion thereof as cycle product through a cooler and into the continuous flow mixer.
- the ratio of withdrawn finished product to cycle product is in the range of from about 1 5 to about 1 30, advantageously about l 10 to about 1 z 20.
- the organic sulfuric acid semi-ester or the organic sulfonic acid used as starting product is degassed in degassing device 1.
- the degassing device is suitably a vacuum degassing machine with rapidly rotating atomization means.
- the degassing is especially important with starting products which have been produced with the use of gas mixtures containing S0 or $0
- the degassed starting product is passed over a metering device 2 into continuous flow mixer 3 into which the alkali and optionally other common additives, for example buffer substances or preserving agents and the 4 and 5 that can be regulated in dependence of the pH value of the product by means of pH measuring device (8).
- the continuous flow mixer a smaller proportion thereof is withdrawn through conduit 9 as finished product, whereas the greater proportion thereof is recycled as cycle product into continuous flow mixer 3 through circulation pump 6 and heat exchanger 7.
- continuous flow mixer 3 a toothed disk mixer is suitably used. It is likewise possible, however, to use a mixer with pronounced conveying effect, such as a mixing pump. In the latter case, circulation pump 6 can be dispensed with. The finished product can also be withdrawn'through conduit 9a after the circulation pump, this being of special advantage when after withdrawal the finished product must be conveyed through a long conduit.
- heat exchanger 7 a plate cooler is preferably used in order to maintain low the pressure loss.
- the process of the invention has a number of advantages over the known processes.
- the detergent is neutralized in a continuous flow mixer instead of, for example, in a kneader, air is practically not introduced into the paste.
- the increase in temperature during the neutralization is kept within moderate limits by the high proportion of cycle product. Theremal damage of the paste which causes the formation of electrolyte is thus substantially avoided.
- Example 1 In a device as specified above, 0.66 kilogram of lauryldiglycol ether-sulfuric acid semi-ester was neutralized with 0.33 kilogram of sodium hydroxide solution of 25 strength with the addition of 0.04 kilogram of sodium citrate solution at a cycle temperature of 20C (behind the heat exchanger) and with a ratio of cycle product to finished product of 15 l. l kilogram of a paste was obtained having a content of washing active substance according to Epton of 70.1 a content of electrolyte of 1.0 and an iron content of less than 5 ppm. The paste had good flowing properties.
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- 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)
Abstract
Flowable pasty raw materials for detergents capable of being pumped and having a content of washing active substance of more than 60% are obtained by neutralizing organic sulfuric acid semiesters or sulfonic acids with alkalies. Before neutralization the sulfuric acid semi-esters or sulfonic acids are degassed and neutralization is carried out in a continuous flow mixer. The greater proportion of the mixture is conducted in a cycle whereas a smaller proportion is withdrawn as finished product. In the continuous flow mixer the usual buffer substances and preserving agents may be added to the products.
Description
United States Patent Frank et al.
PROCESS FOR THE MANUFACTURE OF FLOWABLE PASTY DETERGENTS CAPABLE OF BEING PUMPED Inventors: Rudolf Frank, Coventry, R.l.; Horst Reuner, Burghausen, Salzach; Klaus Ulm, Altotting, both of Germany Hoechst Aktiengesellschaft, Frankfurt am Main, Germany Filed: May 3, 1972 Appl. No.: 250,085
Related US. Application Data Continuation of Ser. No. 795,868, Feb. 3, 1969, abandoned.
Assignee:
Foreign Application Priority Data Feb. 17, 1968 Germany 1692009 References Cited UNITED STATES PATENTS 9/1962 Bozzetti 260/459 SULFONATION PRODUCT 1 Feb. 18, 1975 3,246,026 4/1966 Sowerby et al. 260/459 3,3l3,838 4/1967 Rozzi 260/458 3,337,601 8/1967 Whitman 260/459 3,350,428 10/1967 Brooks et al 260/400 FOREIGN PATENTS OR APPLICATIONS Great Britain Great Britain Primary Examiner-P. E. Willis, Jr. Attorney, Agent, or FirmConnolly & Hutz 57] ABSTRACT Flowable pasty raw materials for detergents capable of being pumped and having a content of washing active substance of more than 60% are obtained by neutralizing organic sulfuric acid semi-esters or sulfonic acids with alkalies. Before neutralization the sulfuric acid semi-esters or sulfonic acids are degassed and neutralization is carried out in a continuous flow mixer. The greater proportion of the mixture is conducted in a cycle whereas a smaller proportion is withdrawn as finished product. In the continuous flow mixer the usual buffer substances and preserving agents may be added to the products.
1 Claim, 1 Drawing Figure BASE ADDlTlVES DEGASSING 2 A 5 METERING DEVICE METERING DEVICE METERING DEVICE W I r l l commuous FLOW MIXER 8 6 H MEASUREMENT CIRCULATION PUMP HEAT EXCHANGER ll FINISHED PRODUCT PAIENTBJ res I8 ms SULFONATION PRODUCT METERING DEVICE METERING DEVICE ADDITIVESO METERING DEVICE I 3 1 CONTINUOUS FLOW MIXER I I I Y 8 l 6 H MEA SUREMENT CIRCULATION PUMP HEAT EXCHANGER FINISHED PRODUCT INVE NTORS RUDOLF FRANK HORST REUNER KLAUS ULM BY Q M mi ATTORNEYS PROCESS FOR THE MANUFACTURE OF FLOWABLE PASTY DETERGENTS CAPABLE OF BEING PUMPED This application is a continuation of application Ser. No. 795,868, filed Feb. 3, 1969 and now abandoned.
The present invention relates to a process for the manufacture of flowable pasty detergents capable of being pumped by neutralizing with alkalies sulfuric acid semi-esters or sulfonic acids, which pasty detergents have a high content of washing active substances, especially more than 60 of washing active substance.
By the term organic sulfuric acid semi-esters or sulfonic acids there are to be understood semi-esters of 5 like, are introduced through further metering devices fatty alcohols and of hydroxy-ethers of fatty alcohols and alkylarylsulfonic acids and olefin-sulfonic acids as well as the product mixtures obtained in the olefin sulfonation which are known as anionic constituents of raw materials for detergents. There are mentioned by way of example semi-esters of fatty alcohols having a chain length of 12 to 18 carbon atoms, oxyethylation products thereof containing 1 to 5 moles of ethylene oxide per mole of fatty alcohol, fatty acid and fatty acid amine oxyethylation products having the same chain length and the same content of ethylene oxide as well as mixtures thereof, aryl and alkylarylsulfonic acids having straightchain or branched alkyl radicals with up to 12 carbon atoms and olefin-sulfonates having a chain length of to 22 carbon atoms, or mixtures of the aforesaid classes of compounds. All these raw materials may be of natural or synthetic origin.
Commercial raw materials for detergents capable of being pumped contain a relatively low proportion of washing active substance. Concentrated detergents having a content of washing active substance of up to about 60 are rather stiff pastes which cannot be pumped with tolerable expense. It is, therefore, impossible to store them in tanks or to transport them in tank cars without considerable costs.
The stiff consistency of the pastes is a result of the high air and electrolyte content originating from the manufacturing conditions. The air content can be reduced by prolonged storage, however to a limited extent only. To prepare pastes having a low content of electrolyte it is necessary to neutralize the organic sulfuric acid semi-esters or sulfonic acids in small quantities with careful control. This procedure considerably increases the price of the products.
The present invention provides a process for the manufacture of pasty detergents containing a high pro portion of washing active substance and capable of being pumped by neutralization of organic sulfuric acid semi-esters or sulfonic acids with alkalies which comprises degassing the organic sulfuric acid semi-esters or sulfonic acids before they are neutralized, mixing them with the alkali and optionally other additives in a continuous flow mixer and thereby neutralizing them, after the mixture has left the continuous flow mixer withdrawing a smaller proportion thereof as finished product and recycling the larger proportion thereof as cycle product through a cooler and into the continuous flow mixer.
The ratio of withdrawn finished product to cycle product is in the range of from about 1 5 to about 1 30, advantageously about l 10 to about 1 z 20.
The process of the invention is now described in greater detail with reference to the accompanying drawing.
The organic sulfuric acid semi-ester or the organic sulfonic acid used as starting product is degassed in degassing device 1. The degassing device is suitably a vacuum degassing machine with rapidly rotating atomization means. The degassing is especially important with starting products which have been produced with the use of gas mixtures containing S0 or $0 The degassed starting product is passed over a metering device 2 into continuous flow mixer 3 into which the alkali and optionally other common additives, for example buffer substances or preserving agents and the 4 and 5 that can be regulated in dependence of the pH value of the product by means of pH measuring device (8). After the product has left the continuous flow mixer a smaller proportion thereof is withdrawn through conduit 9 as finished product, whereas the greater proportion thereof is recycled as cycle product into continuous flow mixer 3 through circulation pump 6 and heat exchanger 7.
As continuous flow mixer 3 a toothed disk mixer is suitably used. It is likewise possible, however, to use a mixer with pronounced conveying effect, such as a mixing pump. In the latter case, circulation pump 6 can be dispensed with. The finished product can also be withdrawn'through conduit 9a after the circulation pump, this being of special advantage when after withdrawal the finished product must be conveyed through a long conduit.
As heat exchanger 7 a plate cooler is preferably used in order to maintain low the pressure loss.
The process of the invention has a number of advantages over the known processes. When the detergent is neutralized in a continuous flow mixer instead of, for example, in a kneader, air is practically not introduced into the paste. The increase in temperature during the neutralization is kept within moderate limits by the high proportion of cycle product. Theremal damage of the paste which causes the formation of electrolyte is thus substantially avoided.
The following example serves to illustrate the invention but it is not intended to limit it thereto.
Example In a device as specified above, 0.66 kilogram of lauryldiglycol ether-sulfuric acid semi-ester was neutralized with 0.33 kilogram of sodium hydroxide solution of 25 strength with the addition of 0.04 kilogram of sodium citrate solution at a cycle temperature of 20C (behind the heat exchanger) and with a ratio of cycle product to finished product of 15 l. l kilogram of a paste was obtained having a content of washing active substance according to Epton of 70.1 a content of electrolyte of 1.0 and an iron content of less than 5 ppm. The paste had good flowing properties.
Commercial pasty detergents generally have a content of electrolyte of 4 to 5 and a content of specific detergent of 60 They constitute stiff pastes that are hardly flowable.
What is claimed is:
1. In a process for the manufacture of flowable pasty detergents capable of being pumped by neutralization of organic sulfuric acid semi-esters or organic sulfonic acids selected from the group consisting of sulfuric acid semi-esters of fatty alcohols having a chain length of 12 3 to 18 carbon atoms, oxyethylation products thereof containing 1 to 5 moles of ethylene oxide per mole of fatty alcohol, fatty acid and fatty acid amide oxyethylation products having a chain length of 12 to 18 carbons and containing 1 to 5 moles of ethylene oxide per mole of said fatty acid or fatty acid amide as well as mixtures thereof, aryl and alkylaryl-sulfonic acids having straight-chain or branched alkyl radicals with up to 12 carbon atoms, olefin sulfonic acids having a chain length of to 22 carbon atoms, and mixtures of the aforesaid classes of compounds, the improvement which comprises removing gases by application of vacactive substance content of 60 to percent.
Claims (1)
1. IN A PROCESS FOR THE MANUFACTURE OF FLOWABLE PASTY DETERGENTS CAPABLE OF BEING PUMPED BY NEUTRALIZATION OF ORGANIC SULFURIC ACID SEMI-ESTERS OR ORGANIC SULFONIC ACIDS SELECTED FROM THE GROUP CONSISTING OF SULFURIC ACID SEMI-ESTERS OF FATTY ALCOHOLS HAVING A CHAIN LENGTH OF 12 TO 18 CARBON ATOMS, OXYETHYLATION PRODUCTS THEREOF CONTAINING 1 TO 5 MOLES OF ETHYLENE OXIDE PER MOLE OF FATTY ALCOHOL, FATTY ACID AND FATTY ACID AMIDE OXYETHYLATION PRODUCTS HAVING A CHAIN LENGTH OF 12 TO 18 CARBONS AND CONTAINING 1 TO 5 MOLES OF ETHYLENE OXIDE PER MOLE OF SAID FATTY ACID OR FATTY ACID AMIDE AS WELL AS MIXTURES THEREOF, ARYL AND ALKYLARYL-SULFONIC ACIDS HAVING STRAIGHTCHAIN OR BRANCHED ALKYL RADICALS WITH UP TO 12 CARBON ATOMS, OLEFIN SULFONIC ACIDS HAVING A CHAIN LENGTH OF 15 TO 22 CARBON ATOMS, AND MIXTURES OF THE AFORESAID CLASSES OF COMPOUNDS, THE IMPROVEMENT WHICH COMPRISES REMOVING GASES BY APPLICATION OF VACUUM FROM THE ORGANIC SULFURIC ACID SEMI-ESTERS OR SULFONIC ACIDS BEFORE THEY ARE NEUTRALIZED, NEUTRALIZING THEM WITH AN ALKALI IN A CONTINUOUS FLOW MIXER, WITHDRAWING A SMALLER PROPORTION OF THE MIXTURE AS FINISHED PRODUCT AFTER IT HAS LEFT THE CONTINUOUS FLOW MIXER, AND RECYCLING THE LARGER PROPORTION OF THE MIXTURES AS CYCLE PRODUCT INTO THE CONTINUOUS FLOW MIXER THROUGH A COOLER, THE RATIO OF SAID WITHDRAWN FINISHED PRODUCT TO SAID CYCLE PRODUCT BEING IN THE RANGE OF FROM ABOUT 1:5 TO 1:30, THE RESULTING FINISHED PRODUCT HAVING A WASHING ACTIVE SUBSTANCE CONTENT OF 60 TO 70 PERCENT.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681692009 DE1692009B2 (en) | 1968-02-17 | 1968-02-17 | PROCESS FOR MANUFACTURING PUMPABLE, FLOWABLE DETERGENT PASTE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3867316A true US3867316A (en) | 1975-02-18 |
Family
ID=5687661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US250085A Expired - Lifetime US3867316A (en) | 1968-02-17 | 1972-05-03 | Process for the manufacture of flowable pasty detergents capable of being pumped |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3867316A (en) |
| JP (1) | JPS4817526B1 (en) |
| DE (1) | DE1692009B2 (en) |
| GB (1) | GB1219384A (en) |
| NL (1) | NL6902119A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993018123A1 (en) * | 1992-03-10 | 1993-09-16 | The Procter & Gamble Company | High active detergent pastes |
| US5529722A (en) * | 1992-03-10 | 1996-06-25 | The Procter & Gamble Company | High active detergent pastes |
| US5543072A (en) * | 1992-10-05 | 1996-08-06 | Mona Industries, Inc. | Synthetic detergent bars and method of making the same |
| US5574005A (en) * | 1995-03-07 | 1996-11-12 | The Procter & Gamble Company | Process for producing detergent agglomerates from high active surfactant pastes having non-linear viscoelastic properties |
| US5665692A (en) * | 1995-02-13 | 1997-09-09 | The Procter & Gamble Company | Process for producing detergent agglomerates in which particle size is controlled |
| US20070049513A1 (en) * | 2003-10-04 | 2007-03-01 | Deruijter Michel J | Process for making a detergent composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055929A (en) * | 1958-06-14 | 1962-09-25 | Bozzetto Giuseppe | Continuous sulphonation of organic substances |
| US3246026A (en) * | 1964-01-14 | 1966-04-12 | Marchon Products Ltd | Manufacturing of sulphated and sulphonated prouducts |
| US3313838A (en) * | 1963-07-01 | 1967-04-11 | Gen Aniline & Film Corp | Reaction of chlorosulfonic acid with alkoxylated alkyl phenols |
| US3337601A (en) * | 1964-03-03 | 1967-08-22 | Process for the production of alcohol sulfates | |
| US3350428A (en) * | 1962-12-12 | 1967-10-31 | Chemithon Corp | Continuous sulfonation process |
-
1968
- 1968-02-17 DE DE19681692009 patent/DE1692009B2/en not_active Ceased
-
1969
- 1969-02-07 GB GB6735/69A patent/GB1219384A/en not_active Expired
- 1969-02-11 NL NL6902119A patent/NL6902119A/xx not_active Application Discontinuation
- 1969-02-17 JP JP44011141A patent/JPS4817526B1/ja active Pending
-
1972
- 1972-05-03 US US250085A patent/US3867316A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055929A (en) * | 1958-06-14 | 1962-09-25 | Bozzetto Giuseppe | Continuous sulphonation of organic substances |
| US3350428A (en) * | 1962-12-12 | 1967-10-31 | Chemithon Corp | Continuous sulfonation process |
| US3313838A (en) * | 1963-07-01 | 1967-04-11 | Gen Aniline & Film Corp | Reaction of chlorosulfonic acid with alkoxylated alkyl phenols |
| US3246026A (en) * | 1964-01-14 | 1966-04-12 | Marchon Products Ltd | Manufacturing of sulphated and sulphonated prouducts |
| US3337601A (en) * | 1964-03-03 | 1967-08-22 | Process for the production of alcohol sulfates |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993018123A1 (en) * | 1992-03-10 | 1993-09-16 | The Procter & Gamble Company | High active detergent pastes |
| US5529722A (en) * | 1992-03-10 | 1996-06-25 | The Procter & Gamble Company | High active detergent pastes |
| US5543072A (en) * | 1992-10-05 | 1996-08-06 | Mona Industries, Inc. | Synthetic detergent bars and method of making the same |
| US5665692A (en) * | 1995-02-13 | 1997-09-09 | The Procter & Gamble Company | Process for producing detergent agglomerates in which particle size is controlled |
| US5574005A (en) * | 1995-03-07 | 1996-11-12 | The Procter & Gamble Company | Process for producing detergent agglomerates from high active surfactant pastes having non-linear viscoelastic properties |
| US20070049513A1 (en) * | 2003-10-04 | 2007-03-01 | Deruijter Michel J | Process for making a detergent composition |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1219384A (en) | 1971-01-13 |
| JPS4817526B1 (en) | 1973-05-30 |
| DE1692009A1 (en) | 1972-07-27 |
| DE1692009B2 (en) | 1973-02-15 |
| NL6902119A (en) | 1969-08-19 |
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