CN114736342A - Preparation method of high-temperature-resistant efficient sulfonated phenolic resin - Google Patents
Preparation method of high-temperature-resistant efficient sulfonated phenolic resin Download PDFInfo
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- CN114736342A CN114736342A CN202210593364.XA CN202210593364A CN114736342A CN 114736342 A CN114736342 A CN 114736342A CN 202210593364 A CN202210593364 A CN 202210593364A CN 114736342 A CN114736342 A CN 114736342A
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- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
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- 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
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/03—Specific additives for general use in well-drilling compositions
- C09K8/035—Organic additives
Abstract
The invention discloses a preparation method of high-temperature-resistant efficient sulfonated phenolic resin, and relates to the technical field of phenolic resin processing. The method comprises the steps of reacting phenol, p-hydroxyphenyloxyacetic acid and an alkaline sulfonic acid agent, then dropwise adding formaldehyde, heating to react until the viscosity of a reaction solution is 60-80mPa.s, diluting with water, then adding sodium p-hydroxybenzenesulfonate to react, then adding an oxidant to react, and finally adding a crosslinking agent to react to obtain the high-temperature-resistant and salt-resistant sulfonated phenolic resin. The preparation method is simple, easy to operate and less in side reaction of products. The sulfonated phenolic resin of the invention also has the characteristic of small usage amount.
Description
Technical Field
The invention belongs to the technical field of phenolic resin processing, and particularly relates to a preparation method of high-temperature-resistant high-efficiency sulfonated phenolic resin.
Background
The drilling fluid loss additive is an important oil field treating agent, has an important position in petroleum drilling, is an important drilling fluid treating agent for maintaining the stable performance of the drilling fluid, improving the rheological property of the drilling fluid, reducing the filtration loss of harmful liquid to a stratum, stabilizing a well wall, ensuring the well diameter regulation and protecting an oil-gas layer, and has important functions of safely and efficiently drilling and preventing drilling accidents. The phenolic resin fluid loss additives are one of the most important branches. The phenolic resin fluid loss additive is prepared by using phenolic resin as a main body and sulfonating or introducing other functional groups. The phenolic resin fluid loss additive is used as a temperature-resistant salt-resistant drilling fluid loss additive, can effectively reduce the high-temperature high-pressure water loss of the drilling fluid, can be prepared with the sulfonated lignite and the sulfonated tannin extract into a three-sulfur drilling fluid system, and is a high-temperature-resistant salt-resistant drilling fluid system commonly used on site at present.
At present, the common phenolic resin fluid loss additives on site are sulfomethyl phenolic resin SMP-I and SMP-II, and the dosage is large, and sulfonated lignite and sulfonated tannin extract are required to be added in a matching way, so that the problem of foaming of the drilling fluid is easily caused; the sulfonated lignite contains chromium element, so that the environmental pollution is serious, and the use of the traditional sulfomethyl phenolic resin is limited; in addition, the temperature resistance of SMP-I and SMP-II is still limited, and the SMP-I and SMP-II can only resist the temperature of 180 ℃ and can not meet the requirement of the ultrahigh temperature well on the filtration loss of the drilling fluid. Therefore, a sulfonated phenolic resin product which is small in addition amount, strong in temperature resistance and salt resistance and still has a good effect when being used alone needs to be researched.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of high-temperature-resistant high-efficiency sulfonated phenolic resin, and the sulfonated phenolic resin prepared by the method has the excellent characteristics of high temperature resistance and salt resistance, can be used independently and has good use effect.
The preparation method of the high-temperature-resistant high-efficiency sulfonated phenolic resin comprises the following steps:
(1) adding 50-70 parts by weight of phenol and 5-10 parts by weight of p-hydroxyphenyloxyacetic acid into a reactor, adding 25-35 parts by weight of alkaline sulfonating agent into the reactor, mixing and stirring, heating to 75 +/-5 ℃, and reacting for 0.5 h;
(2) dropping 120-140 parts by weight of formaldehyde into the reactor while stirring, and keeping the temperature in the reactor at 75 +/-5 ℃;
(3) after the formaldehyde is dripped, heating to 90 ℃ for reaction;
(4) when the viscosity of the reaction solution is 60-80mPa.s, adding 50 parts by weight of water to dilute the reaction solution;
(5) adding 4-12 parts by weight of sodium p-hydroxybenzenesulfonate into the reaction kettle, and reacting for 1 hour;
(6) adding 6-12 parts by weight of oxidant into the reactor, heating to above 95 ℃, and reacting for 2 hours;
(7) finally, adding 0.5-1.5 parts by weight of cross-linking agent into the reactor, adding 100 parts by weight of water for dilution when the reaction temperature is 95 ℃ and the viscosity of the reaction system is 80-100mPa.s, and reacting for 1 hour; after the reaction is finished, the temperature of the reactor is reduced to 50 ℃ by using circulating water, and then the reaction liquid is transferred into a storage tank and is spray-dried into powder in a spray drying tower.
Preferably, the mixing and stirring speed in the step (1) is 60 r/min.
Preferably, the alkaline sulfonating agent in the step (1) is one or more of sodium sulfite, sodium bisulfite, sodium metabisulfite and sodium persulfate.
Preferably, the dropping time of the formaldehyde in the step (3) is 1 h.
Preferably, the reaction temperature in step (5) is 90 ℃.
Preferably, the oxidant in step (6) is one or more of potassium permanganate and potassium ferrate.
Preferably, the cross-linking agent in the step (7) is one or more of triethanolamine, trimethylamine, triethylene tetramine and ethylene diamine tetraacetic acid.
The invention also aims to provide the high-temperature-resistant high-efficiency sulfonated phenolic resin prepared by the method.
Compared with the prior art, the invention has the following beneficial effects:
according to the preparation method of the sulfonated phenolic resin, besides phenol, formaldehyde and a sulfonating agent, p-hydroxyphenyloxyacetic acid and p-hydroxyphenylsodium sulfonate are introduced, namely carboxyl and benzenesulfonic acid groups are introduced, so that the obtained product can be better adsorbed on the surface of clay to form a space grid structure, and the product has a good fluid loss reduction effect;
in the later stage of the synthesis process, a strong oxidant is also added, and the oxidant can continuously oxidize non-temperature-resistant groups such as ether bonds and the like generated by side reactions in the synthesis process to form temperature-resistant groups such as carboxyl and the like, so that the temperature resistance of the treating agent is enhanced, and the fluid loss reducing effect of the treating agent is further improved;
in the invention, a proper amount of cross-linking agent is introduced in the synthesis process, so that the cross-linking degree of the resin material is improved, the prepared sulfonated phenolic resin material can be independently used, and the sulfonated phenolic resin material also has an excellent fluid loss reduction effect.
The preparation method is simple, easy to operate and less in side reaction of products. The sulfonated phenolic resin of the invention also has the characteristic of small usage amount.
Detailed Description
In order to make the technical solutions of the present invention better understood by those skilled in the art, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. This invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein, but rather should be construed as set forth in a manner that provides a thorough understanding of the present disclosure. All other embodiments, which can be obtained by a person skilled in the art without inventive step based on the embodiments of the present invention, are within the scope of protection of the present invention. It is explicitly and implicitly understood by one skilled in the art that the embodiments described herein can be combined with other embodiments.
The advantages of the invention will be further illustrated by the following examples, which are not to be construed as limiting the invention.
Example 1
A preparation method of high-temperature-resistant high-efficiency sulfonated phenolic resin comprises the following steps:
1) adding 50g of phenol and 10g of p-hydroxyphenyloxyacetic acid into a reactor, adding 35g of sodium sulfite and sodium bisulfite into the reactor, mixing and stirring, heating to 75 +/-5 ℃, and reacting for 0.5 h;
2) dropwise adding 140g of formaldehyde into the reactor while stirring (completely dropwise adding for 1 h), and keeping the temperature in the reactor at 75 +/-5 ℃;
3) after the formaldehyde is added dropwise, heating to 90 ℃ to react until the viscosity of the reaction solution is 70mPa.s, adding 50g of water to dilute the reaction solution, then adding 12g of sodium p-hydroxybenzenesulfonate into the reaction kettle, and reacting for 1 h;
4) step 3), after the reaction is finished, adding 12g of potassium permanganate into the reactor, heating to 95-100 ℃, and reacting for 2 h;
5) and 4) after the reaction is finished, adding 1g of triethanolamine into the reactor, controlling the reaction temperature to be 95 ℃, reacting until the system viscosity is 90mPa.s, adding 100g of water for dilution, reacting for 1h again, reducing the temperature of the reactor to 50 ℃ by circulating water, transferring the reaction liquid into a storage tank, and performing spray drying in a spray drying tower to obtain powder.
Example 2
A preparation method of high-temperature-resistant high-efficiency sulfonated phenolic resin comprises the following steps:
1) adding 60g of phenol and 7.5g of p-hydroxyphenyloxyacetic acid into a reactor, adding 30g of sodium hydrosulfite into the reactor, mixing and stirring, heating to 75 +/-5 ℃, and reacting for 0.5 h;
2) dropwise adding 130g of formaldehyde into the reactor while stirring (completely dropwise adding for 1 h), and keeping the temperature in the reactor at 75 +/-5 ℃;
3) after the formaldehyde is added dropwise, heating to 90 ℃ to react until the viscosity of the reaction solution is 70mPa.s, adding 50g of water to dilute the reaction solution, then adding 8g of sodium p-hydroxybenzenesulfonate into the reaction kettle, and reacting for 1 h;
4) step 3) after the reaction is finished, adding 6g of potassium ferrate into the reactor, heating to 95-100 ℃, and reacting for 2 h;
5) and 4) after the reaction is finished, adding 1.5g of trimethylamine into the reactor, keeping the reaction temperature at 95 ℃, adding 100g of water for dilution when the system viscosity is 90mPa.s, reacting for 1h, reducing the temperature of the reactor to 50 ℃ by circulating water, transferring the reaction liquid into a storage tank, and performing spray drying in a spray drying tower to obtain powder.
Example 3
A preparation method of high-temperature-resistant high-efficiency sulfonated phenolic resin comprises the following steps:
1) adding 70g of phenol and 5g of p-hydroxyphenyloxyacetic acid into a reactor, adding 25g of sodium hydrosulfite and sodium persulfate into the reactor, mixing and stirring, heating to 75 +/-5 ℃, and reacting for 0.5 h;
2) dropping 120g of formaldehyde into the reactor while stirring (dropping is complete within 1 hour), and keeping the temperature in the reactor at 75 +/-5 ℃;
3) after the formaldehyde is added dropwise, heating to 90 ℃ to react until the viscosity of the reaction solution is 80mPa.s, adding 50g of water to dilute the reaction solution, then adding 4g of sodium p-hydroxybenzenesulfonate into the reaction kettle, and reacting for 1 h;
4) step 3), after the reaction is finished, adding 9g of potassium permanganate into the reactor, heating to 95-100 ℃, and reacting for 2 h;
5) and 4) after the reaction is finished, adding 0.5g of triethylene tetramine into the reactor, controlling the reaction temperature to be 95 ℃, adding 100g of water for dilution when the system viscosity is 100mPa.s, reacting for 1h, reducing the temperature of the reactor to 50 ℃ by circulating water, transferring the reaction liquid into a storage tank, and performing spray drying in a spray drying tower to obtain powder.
Example 4
A preparation method of high-temperature-resistant high-efficiency sulfonated phenolic resin comprises the following steps:
1) adding 60g of phenol and 5g of p-hydroxyphenyloxyacetic acid into a reactor, adding 25g of sodium sulfite and sodium bisulfite into the reactor, mixing and stirring, heating to 75 +/-5 ℃, and reacting for 0.5 h;
2) dropping 130g of formaldehyde into the reactor while stirring (dropping is complete for 1 h), and keeping the temperature in the reactor at 75 +/-5 ℃;
3) after the formaldehyde is dripped, heating to 90 ℃ to react until the viscosity of the reaction solution is 60mPa.s, adding 50g of water to dilute the reaction solution, then adding 12g of sodium p-hydroxybenzenesulfonate into the reaction kettle, and reacting for 1 h;
4) step 3), after the reaction is finished, adding 9g of potassium ferrate into the reactor, heating to 95-100 ℃, and reacting for 2 h;
5) and 4) after the reaction is finished, adding 1.0g of ethylenediamine tetraacetic acid into the reactor, keeping the reaction temperature at 95 ℃, adding 100g of water for dilution when the system viscosity reaches 80mPa.s, reacting for 1h, reducing the temperature of the reactor to 50 ℃ by circulating water, transferring the reaction liquid into a storage tank, and performing spray drying in a spray drying tower to obtain powder.
Example 5
A preparation method of high-temperature-resistant high-efficiency sulfonated phenolic resin comprises the following steps:
1) adding 70g of phenol and 10g of p-hydroxyphenyloxyacetic acid into a reactor, adding 35g of sodium hydrosulfite into the reactor, mixing and stirring, heating to 75 +/-5 ℃, and reacting for 0.5 h;
2) dropping 120g of formaldehyde into the reactor while stirring (dropping is complete within 1 hour), and keeping the temperature in the reactor at 75 +/-5 ℃;
3) after the formaldehyde is dripped, heating to 90 ℃ to react until the viscosity of the reaction solution is 60mPa.s, adding 50g of water to dilute the reaction solution, then adding 4g of sodium p-hydroxybenzenesulfonate into the reaction kettle, and reacting for 1 hour;
4) step 3) after the reaction is finished, adding 6g of potassium ferrate into the reactor, heating to 95-100 ℃, and reacting for 2 h;
5) and 4) after the reaction is finished, adding 0.5g of triethylene tetramine into the reactor, keeping the reaction temperature at 95 ℃, adding 100g of water for dilution when the system viscosity is 90mPa.s, reacting for 1h, reducing the temperature of the reactor to 50 ℃ by circulating water, transferring the reaction liquid into a storage tank, and performing spray drying in a spray drying tower to obtain powder.
TABLE 1 Components for preparing high temperature resistant highly effective sulfonated phenolic resins
| The content of each component | Example 1 | Example 2 | Example 3 | Example 4 | Example 5 |
| Phenol/g | 50 | 60 | 70 | 60 | 70 |
| P-hydroxyphenyloxyacetic acid/g | 10 | 7.5 | 5 | 5 | 10 |
| Sodium p-hydroxybenzenesulfonate/g | 12 | 8 | 4 | 12 | 4 |
| Formaldehyde/g | 140 | 130 | 120 | 130 | 120 |
| Basic catalyst/g | 35 | 30 | 25 | 25 | 35 |
| Oxidant/g | 12 | 6 | 9 | 9 | 6 |
| Crosslinking agent/g | 1 | 1.5 | 0.5 | 1 | 0.5 |
The performances of the high temperature resistant highly effective sulfonated phenolic resins prepared in examples 1-5 of the present invention, as well as SMP-I (products meeting the medium petroleum standard from Jingzhou chemical industry Co., Ltd.) and SMP-II (products meeting the medium petroleum standard from Jingzhou chemical industry Co., Ltd.) were evaluated indoors by comparing using the petroleum standard Q/SYTZ 0335-2018, and the specific results are shown in Table 2.
TABLE 2
Preparing an experimental slurry according to a medium petroleum standard Q/SYTZ 0335-2018, and detecting and calculating the apparent viscosity of the sample slurry after aging for 16 hours at 180 ℃; preparing test slurry according to the medium petroleum standard Q/SYTZ 0335-2018, loading the prepared test slurry into an aging tank, and respectively putting the aging tank into a roller furnace to roll and age for 16h at constant temperature of 180 ℃, 200 ℃ and 220 ℃. Taking out and cooling to room temperature, pouring out the test slurry, stirring at high speed for 5min, and detecting the high-temperature high-pressure filtration loss under the conditions of 150 ℃, 180 ℃, 200 ℃ and 3.45MPa respectively according to 3.3 in GB/T16783-1997.
As can be seen from Table 2, when the addition amount of SMP-I and SMP-II is 2.5%, the water loss at high temperature and high pressure at 150 ℃ far exceeds 28mL required by the medium petroleum standard Q/SYTZ 0335-2018 standard, and the corresponding water loss at high temperature and high pressure is larger along with the increase of the temperature; the water loss at 150 ℃ and high pressure of the synthesized high-temperature-resistant high-efficiency sulfonated phenolic resin III is less than 28mL, the viscosity is low, the requirements of the medium petroleum standard Q/SYTZ 0335-2018 are met, the effect of the embodiment 5 in five formulas is the best, the temperature resistance is the strongest, the water loss at 220 ℃ and 200 ℃ is only 23mL, the high-temperature-resistant high-pressure sulfonated phenolic resin III shows good high-temperature-resistant salt-resistant capability, and the temperature resistance reaches 220 ℃.
Those not described in detail in this specification are within the skill of the art. Although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments described in the foregoing detailed description, or equivalent changes may be made in some of the features of the embodiments. All equivalents that can be substituted by the contents of the specification of the present invention and applied directly or indirectly to other related technical fields are within the scope of the present invention.
Claims (8)
1. The preparation method of the high-temperature-resistant high-efficiency sulfonated phenolic resin is characterized by comprising the following steps of:
(1) adding 50-70 parts by weight of phenol and 5-10 parts by weight of p-hydroxyphenyloxyacetic acid into a reactor, adding 25-35 parts by weight of an alkaline sulfonating agent into the reactor, mixing and stirring, heating to 75 +/-5 ℃, and reacting for 0.5 h;
(2) dropping 120-140 parts by weight of formaldehyde into the reactor while stirring, and keeping the temperature in the reactor at 75 +/-5 ℃;
(3) after the formaldehyde is dripped, heating to 90 ℃ for reaction;
(4) when the viscosity of the reaction solution is 60-80mPa.s, adding 50 parts by weight of diluted reaction solution;
(5) adding 4-12 parts by weight of p-hydroxy benzene sodium sulfonate into the reaction kettle, and reacting for 1 hour;
(6) adding 6-12 parts by weight of oxidant into the reactor, heating to above 95 ℃, and reacting for 2 hours;
(7) finally, adding 0.5-1.5 parts by weight of cross-linking agent into the reactor, adding 100 parts by weight of water for dilution when the reaction temperature is 95 ℃ and the viscosity of the reaction system is 80-100mPa.s, and reacting for 1 hour; after the reaction is finished, the temperature of the reactor is reduced to 50 ℃ by using circulating water, and then the reaction liquid is transferred into a storage tank and is spray-dried into powder in a spray drying tower.
2. The method for preparing the high temperature resistant and high efficiency sulfonated phenolic resin according to claim 1, wherein the mixing and stirring speed in step (1) is 60 r/min.
3. The method for preparing the high temperature resistant and high efficiency sulfonated phenolic resin according to claim 1, wherein the alkali sulfonating agent in step (1) is one or more of sodium sulfite, sodium bisulfite, sodium metabisulfite and sodium persulfate.
4. The method for preparing the high temperature resistant and high efficiency sulfonated phenolic resin according to claim 1, wherein the dropping time of the formaldehyde in the step (3) is 1 h.
5. The method for preparing the high temperature resistant and high efficiency sulfonated phenolic resin according to claim 1, wherein the reaction temperature in step (5) is 90 ℃.
6. The method for preparing the high temperature resistant and high efficiency sulfonated phenolic resin according to claim 1, wherein the oxidizing agent in step (6) is one or more of potassium permanganate and potassium ferrate.
7. The method for preparing the high temperature resistant and high efficiency sulfonated phenolic resin according to claim 1, wherein the cross-linking agent in step (7) is one or more of triethanolamine, trimethylamine, triethylene tetramine, and ethylene diamine tetraacetic acid.
8. A high temperature resistant highly effective sulfonated phenolic resin, characterized in that it is prepared by the method of any one of claims 1 to 7.
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| CN202311765320.1A CN117757009A (en) | 2022-05-27 | 2022-05-27 | Preparation method of high-temperature-resistant high-efficiency sulfonated phenolic resin |
| CN202210593364.XA CN114736342A (en) | 2022-05-27 | 2022-05-27 | Preparation method of high-temperature-resistant efficient sulfonated phenolic resin |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653835A1 (en) * | 1976-11-26 | 1978-06-01 | Vnii Sintetischeskich Smol | Liq. acidic phenolic resin condensn. prods. - useful as curing agents for thermosetting resins, made by reacting a sulphonated phenol aldehyde resin, urea and formaldehyde |
| CN101798914A (en) * | 2010-04-08 | 2010-08-11 | 中国石油大学(华东) | Method for improving high-temperature stability of sulfonated drilling fluid |
| CN110560161A (en) * | 2019-08-21 | 2019-12-13 | 浙江大学 | Preparation method of sulfonated phenolic resin type solid acid catalyst and application of sulfonated phenolic resin type solid acid catalyst in glycerol esterification reaction |
| CN114085343A (en) * | 2020-08-24 | 2022-02-25 | 中石化石油工程技术服务有限公司 | Modified sulfonated phenolic resin filtrate reducer for drilling fluid and preparation method thereof |
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- 2022-05-27 CN CN202210593364.XA patent/CN114736342A/en active Pending
- 2022-05-27 CN CN202311765320.1A patent/CN117757009A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2653835A1 (en) * | 1976-11-26 | 1978-06-01 | Vnii Sintetischeskich Smol | Liq. acidic phenolic resin condensn. prods. - useful as curing agents for thermosetting resins, made by reacting a sulphonated phenol aldehyde resin, urea and formaldehyde |
| CN101798914A (en) * | 2010-04-08 | 2010-08-11 | 中国石油大学(华东) | Method for improving high-temperature stability of sulfonated drilling fluid |
| CN110560161A (en) * | 2019-08-21 | 2019-12-13 | 浙江大学 | Preparation method of sulfonated phenolic resin type solid acid catalyst and application of sulfonated phenolic resin type solid acid catalyst in glycerol esterification reaction |
| CN114085343A (en) * | 2020-08-24 | 2022-02-25 | 中石化石油工程技术服务有限公司 | Modified sulfonated phenolic resin filtrate reducer for drilling fluid and preparation method thereof |
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