GB819035A - Improvements in process for preparing mixed nonionic-anionic emulsifiers - Google Patents
Improvements in process for preparing mixed nonionic-anionic emulsifiersInfo
- Publication number
- GB819035A GB819035A GB3036/56A GB303656A GB819035A GB 819035 A GB819035 A GB 819035A GB 3036/56 A GB3036/56 A GB 3036/56A GB 303656 A GB303656 A GB 303656A GB 819035 A GB819035 A GB 819035A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyoxyethylene
- carbon atoms
- oxyethylene
- fatty acid
- ethers
- 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
Links
- 239000003995 emulsifying agent Substances 0.000 title abstract 7
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkyl aryl sulphonic acid Chemical compound 0.000 abstract 35
- 125000004432 carbon atom Chemical group C* 0.000 abstract 14
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 13
- 150000002148 esters Chemical class 0.000 abstract 12
- 229920000056 polyoxyethylene ether Polymers 0.000 abstract 10
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 9
- 239000000194 fatty acid Substances 0.000 abstract 9
- 229930195729 fatty acid Natural products 0.000 abstract 9
- 238000000034 method Methods 0.000 abstract 8
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 abstract 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- 125000006353 oxyethylene group Chemical group 0.000 abstract 6
- 239000004094 surface-active agent Substances 0.000 abstract 6
- 239000004359 castor oil Substances 0.000 abstract 5
- 235000019438 castor oil Nutrition 0.000 abstract 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 5
- 229940051841 polyoxyethylene ether Drugs 0.000 abstract 5
- 239000003784 tall oil Substances 0.000 abstract 5
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 abstract 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 4
- 150000004665 fatty acids Chemical class 0.000 abstract 4
- 150000002334 glycols Chemical class 0.000 abstract 4
- 239000000600 sorbitol Substances 0.000 abstract 4
- 150000005846 sugar alcohols Polymers 0.000 abstract 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 abstract 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 3
- BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical compound C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 abstract 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 abstract 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 3
- 125000000129 anionic group Chemical group 0.000 abstract 3
- 229910052791 calcium Inorganic materials 0.000 abstract 3
- 239000011575 calcium Substances 0.000 abstract 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 abstract 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 abstract 2
- 235000011941 Tilia x europaea Nutrition 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 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 abstract 2
- BVEGNPSFKQMTQZ-UHFFFAOYSA-N calcium;1,2-di(nonyl)naphthalene Chemical compound [Ca].C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 BVEGNPSFKQMTQZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 229940100242 glycol stearate Drugs 0.000 abstract 2
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 2
- 150000007529 inorganic bases Chemical class 0.000 abstract 2
- 229940070765 laurate Drugs 0.000 abstract 2
- 239000004571 lime Substances 0.000 abstract 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 abstract 2
- 239000000347 magnesium hydroxide Substances 0.000 abstract 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 abstract 2
- 159000000003 magnesium salts Chemical class 0.000 abstract 2
- 238000006386 neutralization reaction Methods 0.000 abstract 2
- 230000003472 neutralizing effect Effects 0.000 abstract 2
- MXXDSLLVYZMTFA-UHFFFAOYSA-N octadecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 MXXDSLLVYZMTFA-UHFFFAOYSA-N 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 2
- 229920000059 polyethylene glycol stearate Polymers 0.000 abstract 2
- 229920000151 polyglycol Polymers 0.000 abstract 2
- 239000010695 polyglycol Substances 0.000 abstract 2
- ONQDVAFWWYYXHM-UHFFFAOYSA-M potassium lauryl sulfate Chemical compound [K+].CCCCCCCCCCCCOS([O-])(=O)=O ONQDVAFWWYYXHM-UHFFFAOYSA-M 0.000 abstract 2
- 239000002002 slurry Substances 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- RAADJDWNEAXLBL-UHFFFAOYSA-N 1,2-di(nonyl)naphthalene Chemical compound C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 RAADJDWNEAXLBL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005909 Kieselgur Substances 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 239000012874 anionic emulsifier Substances 0.000 abstract 1
- OGOBUJSXNMFAEE-UHFFFAOYSA-N azanium;3,6-di(nonyl)naphthalene-1-sulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C1=CC(CCCCCCCCC)=CC2=CC(CCCCCCCCC)=CC=C21 OGOBUJSXNMFAEE-UHFFFAOYSA-N 0.000 abstract 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 abstract 1
- 229910001863 barium hydroxide Inorganic materials 0.000 abstract 1
- BBCDCWSBHCIZJI-UHFFFAOYSA-L barium(2+);2-dodecylbenzenesulfonate Chemical compound [Ba+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O BBCDCWSBHCIZJI-UHFFFAOYSA-L 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 1
- 239000000920 calcium hydroxide Substances 0.000 abstract 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000003760 tallow Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(1) A process of preparing a mixed non-ionic anionic emulsifier comprises neutralizing an alkyl aryl sulphonic acid containing from 8 to 18 carbon atoms in the alkyl radical or a sulphated hydroxy compound containing at least one hydrocarbon chain having from 8 to 18 carbon atoms with an inorganic base, usually an alkaline earth or alkali metal base including lithium and magnesium, in the presence of a non-ionic surface-active agent which is a partial fatty acid ester, which fatty acid contains at least 12 carbon atoms, of a polyhydric alcohol or a polyoxyethylene ether of a compound containing a hydrophobe hydrocarbon radical. (2) Non-ionic surface-active agents mentioned include fatty acid partial esters of polyhydric alcohols such as the lauric, palmitic, oleic, stearic and tall oil partial esters of glycerol, the hexitols or anhydrides thereof and the products obtained by etherifying such partial esters with ethylene oxide, the fatty acid esters of polyoxyethylene glycols and of hexitol polyoxyethylene ethers, e.g. polyoxyethylene glycol stearate and laurate and the hexaoleate of sorbitol polyoxyethylene esters containing 40 to 50 oxyethylene groups per mol., alcohol ethers of polyoxyethylene glycols derived from alcohols containing at least 12 carbon atoms, e.g. polyoxyethylene lauryl alcohol, alkyl phenol of nonyl phenol polyglycol ethers, polyoxyethylene ethers of higher alkyl mercaptans, polyoxyethylene derivatives of aliphatic amines having at least 12 carbon atoms and polyoxyethylene derivatives of aliphatic amines having at least 12 carbon atoms. (3) The anionic components of the emulsifiers produced by the process are sodium octadecyl benzene sulphonate, calcium dinonyl naphthalene sulphonate, the sodium salt of sulphated castor oil and potassium lauryl sulphate, alkaline earth metal salts of alkyl aryl sulphonic acids containing from 12 to 16 carbon atoms in the alkyl group and calcium and magnesium salts of dodecyl benzene sulphonic acid.ALSO:A process of preparing a mixed nonionicanionic emulsifier comprises neutralizing an alkyl aryl sulphonic acid containing from 8 to 18 carbon atoms in the alkyl radical or a sulphated hydroxy compound containing at least one hydrocarbon chain having from 8 to 18 carbon atoms with an inorganic base in the presence of a nonionic surface active agent which is a partial fatty acid ester, which fatty acid contains at least 12 carbon atoms, of a polyhydric alcohol or a polyoxyethylene ether of a compound containing a hydrophobe hydrocarbon radical. Nonionic surface-active agents mentioned include fatty acid partial esters of polyhydric alcohols such as the lauric, palmitic, oleic, stearic and tall oil partial esters of glycerol, the hexitols or anhydrides thereof and the products obtained by etherifying such partial esters with ethylene oxide, the fatty acid esters of polyoxyethylene glycols and the fatty acid esters of hexitol polyoxyethylene ethers, e.g. polyoxyethylene glycol stearate and laurate and the hexaoleate of sorbitol polyoxyethylene ethers containing 40 to 50 oxyethylene groups per mol., alcohol ethers of polyoxyethylene glycols derived from alcohols containing at least 12 carbon atoms, e.g. polyoxyethylene lauryl alcohol, alkyl phenol polyglycol ethers, polyoxyethylene ethers of higher alkyl mercaptans, polyoxyethylene derivatives of aliphatic amines having at least 12 carbon atoms and polyoxyethylene derivatives of aliphatic amines having at least 12 carbon atoms. Among the anionic components of the emulsifier produced by the process are sodium octadecyl benzene sulphonate, calcium dinonyl naphthalene sulphonate, calcium polydecyl benzene sulphonate, barium dodecyl benzene sulphonate, ammonium dinonyl naphthalene sulphonate, the sodium salt of sulphated castor oil and potassium lauryl sulphate, alkaline earth metal salts of alkyl aryl sulphonic acids containing from 12 to 16 carbon atoms in the alkyl group and calcium and magnesium salts of dodecyl benzene sulphonic acid. Emulsifying agents are obtained in examples when dodecyl benzene is sulphonated with oleum, trimethyl benzene and water are added to the reacted mixture, the trimethyl benzene solution of the sulphonic acid is separated, mixed with a polyoxyethylene ether of sorbitan monotall oil ester containing 16 oxyethylene groups per mol., a lime slurry is added to the mixture, diatomaceous earth is added and the mixture filtered, and the filtrate is stripped to remove water and part of the trimethyl benzene; optionally part of the lime slurry is added to the sulphonated product before the anionic surface active agent (1); in a similar process the hexaoleate of sorbitol polyoxyethylene ether containing 50 oxyethylene groups per mol. is employed as surface active agent (2); in a similar process to (1) dinonyl naphthalene is employed as starting material (3); in a similar process castor oil is sulphated in the first step (4) and in a similar process lauryl alcohol is sulphated with sulphur trioxide vapour at a concentration of 10 per cent in air, in the first stage. Additional examples relate to the neutralization of dodecyl benzene sulphonic acid with calcium hydroxide in the presence of oxyethylene lauryl alcohol (6); oxyethylene nonyl phenol (7); oxyethylene castor oil (8); the oxyethylene ether of sorbitan mono tall oil ester (9); glycerol monooleate (14); oxyethylene tallow fatty amine (15); the hexaoleate of sorbitol polyoxyethylene ether (16); with lithium hydroxide 10), magnesium hydroxide (11), ammonium hydroxide (12) and barium hydroxide (13) in the presence of oxyethylene ether of sorbitan mono tall oil ester and in the neutralization of castor oil sulphate with magnesium hydroxide in the presence of an oxyethylene ether of sorbitan mono tall oil ester (17). The proportions of ethylene oxide in the non-ionic emulsifiers in Examples (6)-(17) are stated and range from 4 to 40 mols. per mol. of emulsifier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US819035XA | 1955-02-01 | 1955-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB819035A true GB819035A (en) | 1959-08-26 |
Family
ID=22167153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3036/56A Expired GB819035A (en) | 1955-02-01 | 1956-01-31 | Improvements in process for preparing mixed nonionic-anionic emulsifiers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB819035A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2357300A1 (en) * | 1976-07-06 | 1978-02-03 | Exxon Research Engineering Co | COMPOSITION AND PROCESS FOR INHIBITIONING THE EVAPORATION OF STORED HYDROCARBONS |
| EP0062475A3 (en) * | 1981-03-30 | 1983-09-21 | Monsanto Company | Surfactant compositions, preparation and stabilization of coal in oil mixtures |
| WO2006111563A1 (en) * | 2005-04-21 | 2006-10-26 | Akzo Nobel N.V. | Agrochemical compositions containing naphthalene sulfonate derivatives and nitrogen-containing surfactants |
| CN101545217B (en) * | 2009-04-30 | 2011-01-05 | 浙江华晟化学制品有限公司 | Terylene discharge printing synergistic agent and production method thereof, processing tin and discharge printing primary stock |
| CN101690877B (en) * | 2009-08-10 | 2012-05-09 | 常熟耐素生物材料科技有限公司 | Pentadecylphenol polyoxyethylene ether strong biodegradable surfactant |
| CN111807996A (en) * | 2020-07-31 | 2020-10-23 | 湖南丽臣奥威实业有限公司 | Sulfonation method of fatty alcohol-polyoxyethylene ether |
-
1956
- 1956-01-31 GB GB3036/56A patent/GB819035A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2357300A1 (en) * | 1976-07-06 | 1978-02-03 | Exxon Research Engineering Co | COMPOSITION AND PROCESS FOR INHIBITIONING THE EVAPORATION OF STORED HYDROCARBONS |
| EP0062475A3 (en) * | 1981-03-30 | 1983-09-21 | Monsanto Company | Surfactant compositions, preparation and stabilization of coal in oil mixtures |
| WO2006111563A1 (en) * | 2005-04-21 | 2006-10-26 | Akzo Nobel N.V. | Agrochemical compositions containing naphthalene sulfonate derivatives and nitrogen-containing surfactants |
| US8283292B2 (en) | 2005-04-21 | 2012-10-09 | Akzo Nobel N V | Agrochemical compositions containing naphthalene sulfonate derivatives and nitrogen-containing surfactants |
| US8629085B2 (en) | 2005-04-21 | 2014-01-14 | Akzo Nobel N.V. | Agrochemical compositions containing naphthalene sulfonate derivatives and nitrogen-containing surfactants |
| CN101545217B (en) * | 2009-04-30 | 2011-01-05 | 浙江华晟化学制品有限公司 | Terylene discharge printing synergistic agent and production method thereof, processing tin and discharge printing primary stock |
| CN101690877B (en) * | 2009-08-10 | 2012-05-09 | 常熟耐素生物材料科技有限公司 | Pentadecylphenol polyoxyethylene ether strong biodegradable surfactant |
| CN111807996A (en) * | 2020-07-31 | 2020-10-23 | 湖南丽臣奥威实业有限公司 | Sulfonation method of fatty alcohol-polyoxyethylene ether |
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