CN118359803A - Preparation method of low-foam block modified fatty alcohol polyether - Google Patents
Preparation method of low-foam block modified fatty alcohol polyether Download PDFInfo
- Publication number
- CN118359803A CN118359803A CN202410799583.2A CN202410799583A CN118359803A CN 118359803 A CN118359803 A CN 118359803A CN 202410799583 A CN202410799583 A CN 202410799583A CN 118359803 A CN118359803 A CN 118359803A
- Authority
- CN
- China
- Prior art keywords
- low
- polyether
- epoxy compound
- foam block
- fatty alcohol
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2648—Alkali metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2654—Aluminium or boron; Compounds thereof
-
- 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
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyethers (AREA)
Abstract
The invention relates to a preparation method of low-foam block modified fatty alcohol polyether, and belongs to the technical field of surfactants. The preparation method comprises the following steps: adding aliphatic monohydric alcohol, succinic anhydride and a first epoxy compound into a reaction kettle to connect the segmented polyester segments; then adding a second epoxy compound self-polymerizing connecting polyether segment; and stopping and discharging after the reaction is finished. According to the invention, a block of polyester is added between the aliphatic chain and the polyether chain, so that the small-molecular polyether surfactant is obtained, and the hydrophobicity of the hydrophobic end of the polyether surfactant is enhanced, so that the overall activity is enhanced, and the invention has better washing and emulsifying effects in practical application.
Description
Technical Field
The invention relates to a preparation method of low-foam block modified fatty alcohol polyether, and belongs to the technical field of surfactants.
Background
The block aliphatic polyether is a block polyether with an aliphatic structure and plays an important role in the application of the surfactant. The block aliphatic polyether can be used as a nonionic surfactant and has excellent surface activity and emulsifying property. Because of the aliphatic structure, the polyether has stronger lipophilicity at the interface between water and oil, can effectively reduce the surface tension and improve the wettability and the emulsifying property. In detergents and emulsifiers, block aliphatic polyethers are often used as important ingredients, which are effective in removing greasy stains and improving cleaning performance. In addition, they can be used as dispersants and anti-foaming agents in industrial processes, helping to control foam formation and to increase production efficiency.
Chinese patent CN117264146a discloses a low foam block polyether, which is prepared by copolymerizing polyethylene glycol (PEG) monomer with low surface tension with methyl methacrylate or dipropylmaleate, and has higher surface activity and lower foamability. However, in the preparation method, polyethylene glycol is directly copolymerized with a monomer. One of the products obtained is known to the skilled person as polymethyl methacrylate grafted with polyethylene glycol as side chain by transesterification, which is structurally similar to polycarboxylic acid type water reducing agents and is not a so-called block structure. Although the method successfully introduces the ester bond, the washing and emulsifying effects are not obvious in practical application.
Disclosure of Invention
The invention aims to solve the technical problems that: overcomes the defects of the prior art and provides a preparation method of low-foam block modified fatty alcohol polyether with low cost and high surface activity.
The technical scheme adopted for solving the technical problems is as follows: a method for preparing low-foam block modified fatty alcohol polyether, which is characterized by comprising the following steps:
1) Adding aliphatic monohydric alcohol, succinic anhydride and a first epoxy compound into a reaction kettle according to a molar ratio of 1:4-12:4-12 in an inert atmosphere, adding a supported base catalyst, controlling the reaction temperature at 50-65 ℃ and reacting for 1-2 h;
2) After the reaction is finished, adding a second epoxy compound, reducing the reaction temperature to 30-45 ℃, and continuing the reaction for 2-4 hours, wherein the molar ratio of the second epoxy compound to the aliphatic monohydric alcohol in the step 1) is 6-20:1;
3) And stopping and discharging after the reaction is finished, and removing the supported alkali catalyst.
The invention obtains the small-molecule polyether surfactant with lower preparation cost. According to the invention, a block of polyester is added between the fatty chain and the polyether chain, so that the hydrophobicity of the hydrophobic end of the polyether surfactant is enhanced, and the lengths of the hydrophobic end and the hydrophilic end are equivalent, thereby enhancing the overall activity. The present invention exhibits excellent emulsifying properties and dispersing ability. The unique molecular structure of the emulsion enables the emulsion to form a stable interface between water and oil phase, thereby being beneficial to emulsification and cleaning application in various fields.
The small molecular polyether type surfactant has the advantage of flexible molecular design and has lower requirement on the alkyl length of aliphatic monohydric alcohol. Preferably, the aliphatic monohydric alcohol is hexanol, heptanol or octanol. The aliphatic monohydric alcohol with a certain alkyl length can reduce the overall comprehensive cost.
Preferably, in the preparation method of the low-foam block modified fatty alcohol polyether, the supported alkali catalyst is gamma-Al 2O3 -KOH-K or/and gamma-Al 2O3 -KOH-Cs.
The catalyst used in the present invention is required to catalyze not only polyether reactions but also polyester reactions. The supported base catalyst is selected to ensure the progress of both polymerizations. The polyether is liquid when the preparation and the discharging of the polyether are completed, the catalyst can be separated out through simple filtration after the reaction of the selected supported alkali catalyst, the catalyst is reused, and the solvent is not required to be consumed for washing the product.
More preferably, the supported alkali catalyst is a catalyst formed by compounding gamma-Al 2O3 -KOH-K and gamma-Al 2O3 -KOH-Cs according to a molar ratio of 12-25:1.
The preparation method of the supported alkali catalyst is common in the field, the process is mature, and reference can be made to: duck-shape, catalyst, 1990:32 (4): 198. In the invention, potassium and cesium are mainly selected as compound active groups, gamma-alumina is used as a carrier, and the potassium and cesium are solidified on the alumina carrier, so that the loss of alkali and the pollution to products in the using process are reduced or avoided. The invention provides the preferable proportion of the two, and can simultaneously better ensure the reactivity and the selectivity of polyester reaction and polyether reaction.
The invention does not need to add extra solvent when the reaction is carried out, and the epoxy compound can play a role of the solvent.
Preferably, in the preparation method of the low-foam block modified aliphatic alcohol polyether, the molar ratio of the aliphatic monohydric alcohol, the succinic anhydride and the first epoxy compound is 1:4-6:4-6.
Preferably, in the preparation method of the low-foam block modified aliphatic alcohol polyether, the molar ratio of the second epoxy compound to the aliphatic monohydric alcohol is 12-16:1.
Preferably, in the preparation method of the low-foam block modified fatty alcohol polyether, the molar ratio of the first epoxy compound to the second epoxy compound is 1:3-4.
The polyether obtained at the preferred formulation exhibits better surface activity.
Preferably, in the preparation method of the low-foam block modified aliphatic alcohol polyether, the first epoxy compound in the step 1) is cyclohexane oxide or cyclopentane oxide; the reaction temperature is 55-60 ℃. The preferred first epoxy compound can better enhance the hydrophobicity of the polyester segment.
Preferably, in the preparation method of the low-foam block modified aliphatic alcohol polyether, the second epoxy compound in the step 2) is ethylene oxide or epichlorohydrin; the reaction temperature is 35-40 ℃. The preferred second epoxy compound can better enhance the hydrophilicity of the polyether segment.
At the preferred reaction temperature, the reaction rate is relatively moderate, so that the reaction rate is ensured, and the yield of the reaction is also ensured.
Compared with the prior art, the preparation method of the low-foam block modified fatty alcohol polyether has the following beneficial effects: the preparation method uses the composite supported alkali catalyst, can simultaneously ensure high reaction activity and selectivity of two polymerization reactions of polyester and polyether, and can simply separate and reuse the catalyst without consuming solvents to wash the product. The invention adds a block of polyester between the aliphatic chain and the polyether chain to obtain the small-molecule polyether surfactant, and the preparation cost is lower. The length of the hydrophobic section and the hydrophilic end of the active agent are equivalent, and the hydrophobicity of the hydrophobic end of the polyether surfactant is enhanced, so that the overall activity is enhanced, and the active agent has better washing and emulsifying effects in practical application.
Detailed Description
The present invention will be specifically described below by way of examples. All materials are commercially available, unless otherwise indicated.
Example 1
The supported base catalyst is a catalyst formed by compounding gamma-Al 2O3 -KOH-K and gamma-Al 2O3 -KOH-Cs according to a molar ratio of 18:1.
Preparation of polyethers
1) Adding n-heptanol, succinic anhydride, cyclohexene oxide and the obtained supported base catalyst into a reaction kettle according to a molar ratio of 1:5:5:0.01 under an inert atmosphere, and controlling the reaction temperature at 56 ℃ to react for 1.5h;
2) After the reaction is finished, adding epichlorohydrin, reducing the reaction temperature to 40 ℃, and continuing the reaction for 3 hours, wherein the molar ratio of the epichlorohydrin to the n-heptanol in the step 1) is 15:1;
3) And stopping and discharging after the reaction is finished, and removing the supported alkali catalyst.
Example 2
The supported base catalyst is a catalyst formed by compounding gamma-Al 2O3 -KOH-K and gamma-Al 2O3 -KOH-Cs according to a molar ratio of 12:1.
The polyether preparation process is the same as in example 1.
Example 3
The supported base catalyst is a catalyst formed by compounding gamma-Al 2O3 -KOH-K and gamma-Al 2O3 -KOH-Cs according to a molar ratio of 25:1.
The polyether preparation process is the same as in example 1.
Example 4
Preparation of polyethers
1) Adding n-hexanol, succinic anhydride, cyclopentane epoxide and the supported alkali catalyst obtained in example 1 into a reaction kettle according to a molar ratio of 1:4:4:0.01 under inert atmosphere, and controlling the reaction temperature at 55 ℃ to react for 1h;
2) After the reaction is finished, adding epichlorohydrin, reducing the reaction temperature to 40 ℃, and continuing the reaction for 4 hours, wherein the molar ratio of the epichlorohydrin to the n-hexanol in the step 1) is 16:1;
3) And stopping and discharging after the reaction is finished, and removing the supported alkali catalyst.
Example 5
Preparation of polyethers
1) Adding 2-heptanol, succinic anhydride, cyclohexene oxide and the supported alkali catalyst obtained in example 1 into a reaction kettle according to a molar ratio of 1:6:6:0.01 under an inert atmosphere, and controlling the reaction temperature at 60 ℃ to react for 1.5h;
2) After the reaction is completed, adding ethylene oxide, reducing the reaction temperature to 35 ℃, and continuing the reaction for 3 hours, wherein the molar ratio of the ethylene oxide to the 2-heptanol in the step 1) is 12:1;
3) And stopping and discharging after the reaction is finished, and removing the supported alkali catalyst.
Example 6
Preparation of polyethers
1) Adding n-propanol, succinic anhydride, cyclohexene oxide and the supported alkali catalyst obtained in example 1 into a reaction kettle according to a molar ratio of 1:12:12:0.04 under an inert atmosphere, and controlling the reaction temperature at 60 ℃ to react for 1.5h;
2) After the reaction is completed, adding ethylene oxide, reducing the reaction temperature to 35 ℃, and continuing the reaction for 3 hours, wherein the molar ratio of the ethylene oxide to the n-propanol in the step 1) is 20:1;
3) And stopping and discharging after the reaction is finished, and removing the supported alkali catalyst.
Example 7
The preparation process of the supported alkali catalyst and polyether is the same as in example 1, except that the supported alkali catalyst is composed of gamma-Al 2O3 -KOH-K and gamma-Al 2O3 -KOH-Cs according to a molar ratio of 1:1.
Example 8
The preparation process of the supported base catalyst and polyether is the same as in example 1, except that the supported base catalyst is gamma-Al 2O3 -KOH-K alone.
Example 9
The preparation process of the supported base catalyst and polyether is the same as in example 1, except that the supported base catalyst is gamma-Al 2O3 -KOH-Cs alone.
Example 10
The preparation process of the supported base catalyst and polyether is the same as in example 1, except that in the preparation of the polyether, the cyclohexane oxide is replaced by an equimolar amount of propylene oxide in step 1).
Example 11
The preparation process of the supported base catalyst and polyether is the same as in example 1, except that in the preparation of the polyether, equal molar amounts of cyclohexene oxide are used instead of epichlorohydrin in step 2).
Comparative example 1
The polyether was prepared as in example 1, except that the same amount of sodium methoxide was used instead of the supported base catalyst.
Comparative example 2
Preparation of polyethers
1) Adding n-heptanol, epichlorohydrin and the supported alkali catalyst obtained in example 1 into a reaction kettle according to a molar ratio of 1:15:0.01 under inert atmosphere, controlling the reaction temperature at 40 ℃ and reacting for 4 hours;
2) And stopping and discharging after the reaction is finished, and removing the supported alkali catalyst.
Washing effect experiment, cutting dyed cotton cloth into square cloth pieces with 15cm and 15cm, respectively dripping 5.0g soybean oil on each square cloth piece, standing for 10min, and accurately weighing the quality of the polluted square cloth pieces. The contaminated square cloths were placed in aqueous solutions (0.5 wt%) of the polyethers obtained in the respective examples and comparative examples, respectively, and stirred slowly (1 r/s) for 10min. And (5) weighing the mass again after drying each square cloth piece. The difference between the two masses was calculated, the greater the difference, the better the washing effect was considered. The calculation results are shown in Table 1.
The initial foam height of the polyethers obtained in the respective examples and comparative examples was determined by the Ross-Miles foam height method. The test results are shown in Table 1.
Table 1 test results
。
As can be seen from the test results in Table 1, the polyether prepared according to the present invention has a small initial foam height. The washing effect is obvious.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the invention in any way, and any person skilled in the art may make modifications or alterations to the disclosed technical content to the equivalent embodiments. However, any simple modification, equivalent variation and variation of the above embodiments according to the technical substance of the present invention still fall within the protection scope of the technical solution of the present invention.
Claims (9)
1. A method for preparing low-foam block modified fatty alcohol polyether, which is characterized by comprising the following steps:
1) Adding aliphatic monohydric alcohol, succinic anhydride and a first epoxy compound into a reaction kettle according to a molar ratio of 1:4-12:4-12 in an inert atmosphere, adding a supported base catalyst, controlling the reaction temperature at 50-65 ℃ and reacting for 1-2 h; the first epoxy compound is epoxycyclohexane or epoxycyclopentane;
2) After the reaction is finished, adding a second epoxy compound, reducing the reaction temperature to 30-45 ℃, and continuing the reaction for 2-4 hours, wherein the molar ratio of the second epoxy compound to the aliphatic monohydric alcohol in the step 1) is 6-20:1; the second epoxy compound is ethylene oxide or epichlorohydrin;
3) And stopping and discharging after the reaction is finished, and removing the supported alkali catalyst.
2. The method for preparing the low-foam block modified fatty alcohol polyether according to claim 1, wherein the method comprises the following steps: the aliphatic monohydric alcohol is hexanol, heptanol or octanol.
3. The method for preparing the low-foam block modified fatty alcohol polyether according to claim 1, wherein the method comprises the following steps: the supported base catalyst is gamma-Al 2O3 -KOH-K or/and gamma-Al 2O3 -KOH-Cs.
4. A process for preparing a low foam block modified fatty alcohol polyether as claimed in claim 3, wherein: the supported base catalyst is a catalyst formed by compounding gamma-Al 2O3 -KOH-K and gamma-Al 2O3 -KOH-Cs according to a molar ratio of 12-25:1.
5. The method for preparing the low-foam block modified fatty alcohol polyether according to claim 1, wherein the method comprises the following steps: the molar ratio of the aliphatic monohydric alcohol, the succinic anhydride and the first epoxy compound is 1:4-6:4-6.
6. The method for preparing the low-foam block modified fatty alcohol polyether according to claim 1, wherein the method comprises the following steps: the molar ratio of the second epoxy compound to the aliphatic monohydric alcohol is 12-16:1.
7. The method for preparing the low-foam block modified fatty alcohol polyether according to claim 1, wherein the method comprises the following steps: the molar ratio of the first epoxy compound to the second epoxy compound is 1:3-4.
8. The method for preparing the low-foam block modified fatty alcohol polyether according to claim 1, wherein the method comprises the following steps: the reaction temperature in the step 1) is 55-60 ℃.
9. The method for preparing the low-foam block modified fatty alcohol polyether according to claim 1, wherein the method comprises the following steps: the reaction temperature in the step 2) is 35-40 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410799583.2A CN118359803A (en) | 2024-06-20 | 2024-06-20 | Preparation method of low-foam block modified fatty alcohol polyether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410799583.2A CN118359803A (en) | 2024-06-20 | 2024-06-20 | Preparation method of low-foam block modified fatty alcohol polyether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN118359803A true CN118359803A (en) | 2024-07-19 |
Family
ID=91882567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202410799583.2A Pending CN118359803A (en) | 2024-06-20 | 2024-06-20 | Preparation method of low-foam block modified fatty alcohol polyether |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN118359803A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120172537A1 (en) * | 2009-09-17 | 2012-07-05 | Asahi Glass Company, Limited | Process for producing polyether |
| CN104151535A (en) * | 2014-08-09 | 2014-11-19 | 河北工业大学 | A kind of polyester block copolymer and preparation method thereof |
| CN110498916A (en) * | 2019-05-30 | 2019-11-26 | 华南理工大学 | A kind of method of cyclic ester and the copolymerization of epoxy monomer sequence controlled block |
| CN115181258A (en) * | 2022-06-13 | 2022-10-14 | 福州大学 | Rosin-terminated polyether block copolymer surfactant and preparation method thereof |
| CN116903843A (en) * | 2023-08-24 | 2023-10-20 | 中国科学院长春应用化学研究所 | Polyether-polyester block polyol and preparation method thereof |
-
2024
- 2024-06-20 CN CN202410799583.2A patent/CN118359803A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120172537A1 (en) * | 2009-09-17 | 2012-07-05 | Asahi Glass Company, Limited | Process for producing polyether |
| CN104151535A (en) * | 2014-08-09 | 2014-11-19 | 河北工业大学 | A kind of polyester block copolymer and preparation method thereof |
| CN110498916A (en) * | 2019-05-30 | 2019-11-26 | 华南理工大学 | A kind of method of cyclic ester and the copolymerization of epoxy monomer sequence controlled block |
| CN115181258A (en) * | 2022-06-13 | 2022-10-14 | 福州大学 | Rosin-terminated polyether block copolymer surfactant and preparation method thereof |
| CN116903843A (en) * | 2023-08-24 | 2023-10-20 | 中国科学院长春应用化学研究所 | Polyether-polyester block polyol and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101057048B1 (en) | Surfactant Mixtures Including Short and Long Chain Components | |
| EP1861354B1 (en) | Esterified alkyl alkoxylates used as low-foam surfactants | |
| US6204238B1 (en) | Fatty acid derivatives and their use as surfactants in detergents and cleaners | |
| US9732308B2 (en) | Polyesters | |
| CA2697720C (en) | Esterified alkyl alkoxylates as solid low-foam wetters | |
| CA2077349C (en) | Castable fluid tenside concentrate | |
| EP2880076A1 (en) | Polyesters | |
| EP2663626B1 (en) | Use of optionally oxidized thioethers of polyalkylene glycols in detergents and cleaning agents | |
| US7807615B2 (en) | Production of (co)surfactants by reacting polyols with olefins | |
| CN118359803A (en) | Preparation method of low-foam block modified fatty alcohol polyether | |
| CN1049003C (en) | Concentrated aqueous liquid detergent compositions comprising polyviny lpyrrolidone and a terephthalate-based soil release polymer | |
| ES2380189T3 (en) | Reaction products of 2-propylheptanol with 1-halo-2,3-epoxypropane and 1-hydroxy-2,3-epoxypropane | |
| KR20140040085A (en) | Use of optionally oxidized thioethers of alcohol alkoxylates in detergents and cleaning agents | |
| US8951955B2 (en) | Use of optionally oxidized thioethers of alcohol alkoxylates in washing and cleaning compositions | |
| CN111253278A (en) | Ultrahigh-content alkylolamide, and synthesis process and application thereof | |
| KR102351930B1 (en) | Method for producing fatty acid aklyl ester alkoxylate | |
| KR20050053728A (en) | Alkyl glycidol carbonates used as co-surfactants | |
| US20120184478A1 (en) | Use of optionally oxidized thioethers of polyalkylene oxides in washing and cleaning compositions | |
| Hama | Narrow alcohol ethoxylates | |
| JP2010047656A (en) | Liquid detergent composition | |
| CN117209745A (en) | Synthesis method of fatty acid methyl ester polyoxyethylene ether with low cost and high conversion rate | |
| KR20070036028A (en) | Compositions containing alcohol alkoxylates and uses thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |