GB2166152A - Mixtures of sulphonated fatty acid esters and other organic compounds - Google Patents
Mixtures of sulphonated fatty acid esters and other organic compounds Download PDFInfo
- Publication number
- GB2166152A GB2166152A GB08525637A GB8525637A GB2166152A GB 2166152 A GB2166152 A GB 2166152A GB 08525637 A GB08525637 A GB 08525637A GB 8525637 A GB8525637 A GB 8525637A GB 2166152 A GB2166152 A GB 2166152A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fatty acid
- acid ester
- sulphur trioxide
- organic compound
- process according
- 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.)
- Granted
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 41
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 41
- 239000000194 fatty acid Substances 0.000 title claims abstract description 41
- -1 fatty acid esters Chemical class 0.000 title claims abstract description 34
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 230000032683 aging Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002191 fatty alcohols Chemical class 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- NNYBQONXHNTVIJ-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940063718 lodine Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000005233 alkylalcohol group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940013317 fish oils Drugs 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 235000014643 Orbignya martiana Nutrition 0.000 description 1
- 244000021150 Orbignya martiana Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000010480 babassu oil Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- 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
- C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the manufacture of sulphonated mixtures of fatty acid esters and organic compounds, the sulphonation product whereof are detergent-active, comprises preparing the sulphonated fatty acid ester with an excess amount of sulphur trioxide, adding the organic compound in a quantity which is less than 80 mole % of the excess sulphur trioxide, and neutralizing the reaction mixture. High degrees of sulphonation are achieved.
Description
SPECIFICATION
Process for the manufacture of detergent active mixtures
The present invention relates to a process for the manufacture of detergent-active mixtures.
More in particular, it relates to a cosulphonation process for the manufacture of sulphonated mixtures of fatty acid esters and organic compounds the sulphonation products whereof are detergent-active.
Detergent-active mixtures of this type are of value in detergent products without restriction to the product form and may be used in association with other types of detergent-actives and conventional detergent additives.
Fatty acid ester sulphonates are manufactured by reacting the corresponding fatty acid ester with strong sulphonation agents, in particular, sulphur trioxide in admixture with inert gas. In order to achieve high degrees of sulphonation, amounts of sulphur trioxide in excess of 1:1 stoechiometry with the fatty acid ester are used.
In the German Patent Specification No. 1.418.887 a process is described wherein the molar excess of sulphur trioxide over the fatty acid ester is used for the cosulphation of hydroxyl groups containing compounds such as fatty alcohols, fatty alkylolamides, alkylphenols, etc. The hydroxyl group containing compound is added to the sulphonated fatty acid ester reaction mixture in a molar quantity wich is equal to or exceeds the molar excess of sulphur trioxide over the fatty acid ester. In this process the hydroxylgroup containing compound is sulphated to degrees of up to 90%.
The presence of quantities of unreacted organic compounds, such as for instance unreacted fatty alcohols, is undesirable since they do not contribute to detergency, and therefore negatively influence the manufacturing economy of the product. They often have impairing effects on product characteristics, such as on foaming properties, rheology etc. It is therefore important to achieve a degree of sulphonation as high as possible.
It has now been found that in mixtures of sulphonated fatty ester and excess amount of sulphur trioxide, only part of the remaining SO3 is in a form which is instantly available as sulphonation agent and can be suitably used in a further sulphonation step.
Accordingly, the present invention provides a process for the manufacture of sulphonated mixtures of fatty acid ester and an organic compound the sulphonation product whereof is detergent-active, comprising the steps of:
(1) reacting the fatty acid ester with a molar excess of sulphur trioxide over 1:1 stoechiometry with the fatty acid ester;
(2) adding the organic compound, optionally in admixture with the sulphonation product thereof, to the reaction mixture produced in step (1); and
(3) neutralizing the reaction mixture produced in step (2); the organic compound being added in a quantity which is less than about 80 mole % of the excess of sulphur trioxide.
In the first step of the process the fatty acid ester is sulphonated with a molar excess of sulphur trioxide. The molar excess of sulphur trioxide which must be used to achieve substantially complete sulphonation of the fatty acid ester is dependent of the reactivity of the ester starting material and the temperature. Preferably the mole ratio of sulphur trioxide to fatty acid ester is within the range up to 2.5:1, such as within the range of from 1.5:1 to 2.5:1. Reaction temperatures lie within the range of 0 to 150"C and preferably 30 to 130"C.
Preferably the fatty acid ester/sulphur trioxide reaction mixture is subjected to an ageing step during which the sulphonation of the fatty acid ester to alpha sulphonated material proceeds substantially to completion. The period of the ageing step will reduce with the use of higher molar levels of the sulphur trioxide in the sulphonation mixture. For example when the sulphonation of methyl laurate is performed at 60"C with a mole ratio of 2:1 for sulphur trioxide:ester the ageing period is almost zero, whereas for sulphonation at 70"C with a mole ratio of 1.3:1 it is about 30-45 minutes.
The organic compound is added to the reaction mixture of step (1) after substantially complete sulphonation of the ester. It is added in a quantity which is less than 80 mole %, in particular from 30 to 80 mole % of the excess of sulphur trioxide over 1:1 stoechiometry with the ester.
Best results are achieved when the organic compound is added in a quantity which lies within the range of 40 to 60 mole % of the excess of sulphur trioxide over 1:1 stoechiometry with the ester.
The organic compound reacts with the instantly reactive part of the sulphur trioxide without the need of further heating or ageing, but there is no bar to such further heating.
After addition of the organic compound the reaction mixture may be immediately neutralized with suitable alkali.
The fatty acid esters will usually be derived from naturally occurring fatty acids, but petroleum derived, synthetic, fatty acids can also be used. Suitable are fatty acids having 8 to 22 carbon atoms in the alkyl chain, which are esterified with C1-C6 alcohols, such as methanol or ethanol.
Examples of the sources of glycerides from which suitable fatty acids can be obtained are coconut oil, tallow, palm oil, palm kernel oil, fish oils, soya, babassu and tall oils. The fatty acids will usually be hardened to an lodine Value of 1 or below to reduce the formation of coloured species during sulphonation. Some oils, e.g. tallow, soya and some fish oils, will require hydrogenation to provide suitable fatty acids.
The sulphonation in step (1) is performed using sulphur trioxide in liquid or in gaseous form.
Gaseous sulphur trioxide will be admixed with a diluent gas. The diluent gas, which is normally air, is required to be inert in the sulphonation reaction; nitrogen or carbon dioxide are other suitable diluent gases.
The organic compound should be sulphonatable to yield a detergent-active material. Suitable examples thereof are primary and secondary (C1o-C28) alcohols, (Cro-C20) olefins, alkylphenols and alkylbenzenes having 10 to 16 carbon atoms in the alkyl chain. Preferred are primary fatty alcohols.
When detergent-active mixtures are required having a high ratio of sulphonated organic compound to sulphonated product of the fatty acid ester, it is of advantage to add the organic compound in admixture with the sulphonation product thereof to the reaction mixture produced in step 1. In particular for organic compounds the sulphonation product whereof is not stable in pure form, the use of partially converted material in step 2 of the process, is a preferred way to achieve complete sulphonation of the organic compound in the resulting detergent-active mixture.
Since primary alcohol sulphates are only stable as such, i.e. in their acidic form, to degrees of sulphation below about 90%, they are preferably added in step (2) of the process in up to 90% sulphated form yielding detergent-active mixtures with a high ratio of primary alcohol sulphate to sulphonated product of the fatty acid ester.
The process of the invention will now be further illustrated by way of examples.
Laboratory scale sulphonation experiments were designed to simulate a batch process in a stirred tank reactor. The reaction vessel was a Pyrex 3-necked flask fitted with stirrer, a reflux condenser and a gas inlet tube for introduction of SO3/nitrogen below the surface of the liquid being sulphonated. Gaseous SO,3 (about 10% v/v in nitrogen) was produced by adding liquid SO3 from a burette to a vapouriser, consisting of a Pyrex flask heated at 100" and connected to a supply of dry nitrogen and to the reaction vessel. Mole ratios of SO3 to ester or S03 to alcohol were calculated from the amount of liquid S03 fed to the vapouriser and the weight of ester used. NMR analysis was with the Bruker 360 MHz instrument in all cases.
Example 1
Sulphur trioxide (52.39., 0.654 mole) was added, as a gaseous mixture with nitrogen, to methyl laurate (70.or., 0.327 mole) at 50"C, with stirring, over a period of 1 hour. The resulting sulphonation product was stored at 50 for 90 min, whilst lauryl alcohol (1009., 0.538 mole) was partially sulphated to a nominal 76% conversion by addition of sulphur trioxide (32.79., .409 mole), as a gaseous mixture with nitrogen, at 50".
The sulphonated methyl laurate and the partially sulphated lauryl alcohol were then mixed, and the mixture was kept at 50". Samples were neutralised after 5 min and 2 hr, and a further sample was neutralised after the mixture had been stored at room temperature for 5 days. The neutralised samples were analysed by 'H NMR, using a Bruker 360 MHz instrument, to give the composition data shown in the table I.
Example II
Sulphur trioxide (74.79., .934 mole) was added to methyl laurate (100 g., 467 mole) at 60 , over a period of 1 hr. After storage of the resulting sulphonation product for 3 hr., a sample (10g.) was added to a molten lauryl alcohol (2.49). The resulting mixture was stored in an open beaker at 60 for 5 min, then methanol (0.6 ml) was added and the mixture was neutralised. 'H
NMR analysis gave the composition data shown in the table I.
Example 111
Sulphur trioxide (74.79., .934 mole) was added to methyl laurate (1009., .467 mole) at 600, over a period of 1 hr. The resulting sulphonation product was stored at 400.
Sulphur trioxide (ca. 309., .38 mole) was added to lauryl alcohol (100 g., 0.537 mole) at 40 , over a period of 1 hr. The resulting sulphonation product was examined by 'H NMR after 1 hr, 2 1/2 hr and 21 hr. In all these cases the composition was found to be 71-72 mole % C12H2sSO4H and 28-29 mole % C12H250H, no other species being detected.
Samples (209.) of the lauryl alcohol partial sulphation product when it was 1 hr and 21 hrs old were mixed at 40 , by manual swirling in an open beaker, with samples (21.69) of the methyl laurate sulphonation product. The resulting products were neutralised after 5 min and analysed by 'H NMR, which gase the data shown in the table I.
Example IV
Lauryl alcohol (1509., 0.806 mole) was partly sulphated at 40 by addition of sulphur trioxide (58.09., 0.725 mole), as in the previous examples. 'H NMR gave the conversion of C,2H250H to C,2H250SO3H as 84.5% (immediately after completion of SO3 addition) and 83% (after storage at 40 overnight).
Methyl laurate (709., 0.327 mole) was sulphonated at 60 with sulphur trioxide (52.39, 0.654 mole), as in the previous examples.
5.0g of the resulting mixture was added to 10g of the one-day old lauryl alcohol partial sulphation product described in the preceding paragraph, at 400, in an open beaker. NMR analysis on the product obtained after neutralisation (5 minutes after mixing) gave the data shown in the table I.
Table I Example No. I II III IV conversion of alkylalcohol 70% 0% 71 - 72% 83% to alkylsulphste before step (2) Imbile ratio between aIkylalochol 40% 48% 40 - 41% 49% land unreacted sulphurtrioxide in Istep (2) loomposition of final sulphonation Product in nole % based on total a) b) active: alkyl sulphate 63% 28% 55% 54% 72%
I fatty acid ester sulphonate 11% 44% 24% 26% 12.2%
I fatty acid sulphonate 25% 27% 20% 20% 12.5%
others 1% 1% 1% - 3.3% conversion: alkylalchol to aItylsulphate 100% 100% 100% 100% 96% Ifatty acid ester to fatty acid 98% 98.5% 98% 100% 99%
I (ester) sulphonate a) alkylalcohol partial-sulphonation product wax mixed with fatty acid ester sulphonation product
after 1 hour.
b) alkylalcohol partial-sulphonation product wax mixed with fatty acid ester sulphonation product
after 21 hour.
Claims (10)
1. A process for preparation of sulphonated mixture of fatty acid ester and an organic compound the sulphonation product whereof is detergent-active comprising the steps of:
(1) reacting the fatty acid ester with a molar excess of sulphur trioxide over 1:1 stoechiometry with the fatty acid ester;
(2) adding the organic compound, optionally in admixture with the sulphonation product thereof, to the reaction mixture produced in step (1); and
(3) neutralizing the reaction mixture produced in step (2); the organic compound being added in a quantity which is less than about 80 mole % of the excess of sulphur trioxide.
2. A process according to claim 1 wherein the mole ratio of sulphur trioxide to fatty acid ester in step (1) is within the range of from 1.5:1 to 2.5:1.
3. A process according to claim 1 or 2 wherein the reaction temperature in step (1) is within the range of from 30 C to 130"C.
4. A process according to anyone of the preceding claims wherein the reaction mixture of step (1) is subjected to an ageing step.
5. A process according to anyone of the preceding claims wherein the organic compound is added in a quantity which is of from 30 to 80 mole % of the excess of sulphur trioxide over 1:1 stoechiometry with the fatty acid ester.
6. A process according to claim 5 wherein the organic compound is added in a quantity which is of from 40 to 60 mole % of the excess of sulphur trioxide over 1:1 stoechiometry with the fatty acid ester.
7. A process according to any one of the preceding claims wherein the fatty acid ester is derived from fatty acids having 8 to 22 carbon atoms in the alkyl chain, which are esterified with C,-C6 alcohols.
8. A process according to claim 7 wherein the fatty acid is hardened to an lodine Value of 1 or less.
9. A process according to any one of the preceding claims wherein the organic compound is a primary fatty alcohol having from 10 to 28 carbon atoms.
10. A process according to any one of the preceding claims wherein the organic compound is added in admixture with the sulphonation product thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN283/BOM/85A IN163971B (en) | 1984-10-19 | 1985-10-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848426552A GB8426552D0 (en) | 1984-10-19 | 1984-10-19 | Detergent active mixtures |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8525637D0 GB8525637D0 (en) | 1985-11-20 |
| GB2166152A true GB2166152A (en) | 1986-04-30 |
| GB2166152B GB2166152B (en) | 1988-03-23 |
Family
ID=10568469
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB848426552A Pending GB8426552D0 (en) | 1984-10-19 | 1984-10-19 | Detergent active mixtures |
| GB08525637A Expired GB2166152B (en) | 1984-10-19 | 1985-10-17 | Mixtures of sulphonated fatty acid esters and other organic compounds |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB848426552A Pending GB8426552D0 (en) | 1984-10-19 | 1984-10-19 | Detergent active mixtures |
Country Status (2)
| Country | Link |
|---|---|
| GB (2) | GB8426552D0 (en) |
| PH (1) | PH21179A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111138322A (en) * | 2019-12-27 | 2020-05-12 | 赞宇科技集团股份有限公司 | Production process of high-quality alkyl benzene sulfonic acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB720195A (en) * | 1951-04-20 | 1954-12-15 | Colgate Palmolive Peet Co | Synthetic detergent compositions |
-
1984
- 1984-10-19 GB GB848426552A patent/GB8426552D0/en active Pending
-
1985
- 1985-10-16 PH PH32935A patent/PH21179A/en unknown
- 1985-10-17 GB GB08525637A patent/GB2166152B/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB720195A (en) * | 1951-04-20 | 1954-12-15 | Colgate Palmolive Peet Co | Synthetic detergent compositions |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111138322A (en) * | 2019-12-27 | 2020-05-12 | 赞宇科技集团股份有限公司 | Production process of high-quality alkyl benzene sulfonic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8426552D0 (en) | 1984-11-28 |
| GB2166152B (en) | 1988-03-23 |
| GB8525637D0 (en) | 1985-11-20 |
| PH21179A (en) | 1987-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20031017 |