CN1066448A - The manufacture method of sulphonated acetone formaldehyde polycondensates - Google Patents
The manufacture method of sulphonated acetone formaldehyde polycondensates Download PDFInfo
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- CN1066448A CN1066448A CN 91102863 CN91102863A CN1066448A CN 1066448 A CN1066448 A CN 1066448A CN 91102863 CN91102863 CN 91102863 CN 91102863 A CN91102863 A CN 91102863A CN 1066448 A CN1066448 A CN 1066448A
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- formaldehyde
- acetone
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- wat
- mixed solution
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- YIBPLYRWHCQZEB-UHFFFAOYSA-N formaldehyde;propan-2-one Chemical class O=C.CC(C)=O YIBPLYRWHCQZEB-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 28
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011259 mixed solution Substances 0.000 claims abstract description 12
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims abstract description 11
- 235000010262 sodium metabisulphite Nutrition 0.000 claims abstract description 11
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 7
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 235000010265 sodium sulphite Nutrition 0.000 claims abstract description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 26
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 17
- 235000019253 formic acid Nutrition 0.000 claims description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 2
- 238000007086 side reaction Methods 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- 239000004568 cement Substances 0.000 abstract description 10
- 239000003513 alkali Substances 0.000 abstract description 7
- 239000003638 chemical reducing agent Substances 0.000 abstract description 6
- 238000005516 engineering process Methods 0.000 abstract description 6
- 239000003129 oil well Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000036632 reaction speed Effects 0.000 abstract description 2
- 239000011440 grout Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 5
- 101000957351 Homo sapiens Myc-associated zinc finger protein Proteins 0.000 description 3
- 101000863884 Homo sapiens Sialic acid-binding Ig-like lectin 8 Proteins 0.000 description 3
- 102100038750 Myc-associated zinc finger protein Human genes 0.000 description 3
- 102100029964 Sialic acid-binding Ig-like lectin 8 Human genes 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 235000018927 edible plant Nutrition 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Landscapes
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates in oil, the gas drilled hole, the preparation method of oil well cement water reducer sulphonated acetone formaldehyde polycondensates, formaldehyde, acetone, S-WAT and water are prepared burden by a certain percentage, earlier add the mixed solution of formaldehyde, acetone and Sodium Pyrosulfite in the sodium sulfite aqueous solution S-WAT hydrolysis more in batches, by the adding speed of control mixed solution to sodium sulfite aqueous solution, come controls reaction speed, react wayward to solve in the past in the technology, volatility of raw material is serious, problems such as unstable product quality.The alkali that this method utilizes the S-WAT hydrolysis to produce is made the catalyzer of polycondensation, has removed from adding highly basic and making catalyzer, reduces production costs, and is easy to suitability for industrialized production.
Description
The invention provides a kind of organic high molecular compound, the manufacture method of sulphonated acetone formaldehyde polycondensates relates to the grout water reducer technical field in oil, the Sweet natural gas probing well cementation process.
Water reducer is called the flow improver dispersion agent again, is important oil well cement additive, and it can improve the flowability of grout effectively, improves pumping efficiency, and the assurance well cementing operation is carried out smoothly.Usually the oil well cement water reducer of usefulness is sulfonated lignin and bitter edible plant sulfonic acid and formaldehyde polycondensate, these water reducer limitation are big, it is serious to bubble as the lignosulfonic acid salt, high temperature resistance not, though bitter edible plant sulfonic acid and formaldehyde polycondensate has better than the drag-reduction effect of sulfonated lignin, but still exist the problem of heat-resisting property difference, and self is poisonous, easy care not, contaminate environment.Development along with petroleum industry, middle-deep well, the ultra deep well increase is very fast, the bottom temperature height, the conditions down-hole complexity, make the difficulty of well cementation work increasing, the starting material of well cementing operation and technology are proposed higher requirement, thereby also should satisfy its requirement simultaneously temperature resistance and other performances of the water reducer of oil well cement.Carried out number of research projects for the flow improver of seeking a kind of high temperature resistance both at home and abroad in recent years, all having introduced sulphonated acetone formaldehyde polycondensates as EP0163459 and DE3429068 and " oilfield chemistry " 1990.7.No2. 129-133 page or leaf etc. is the good well cement tolerance blocking of a kind of heat-resisting property, but all there are certain problem in this polycondensate manufacture method and cost aspect.
The preparation sulphonated acetone formaldehyde polycondensates was to take acetone, formaldehyde and sodium bisulfite by following proportioning in the past: acetone: formaldehyde: sodium bisulfite=add in reaction flask at 6: 3: 1, under alkaline effects such as KOH and NaOH, polycondensation takes place, and controls the carrying out of reaction by the adding speed of control alkali lye.Aforesaid method is in adding the alkali process, because the concentration of alkali is low in the beginning reaction mixture, reaction is carried out slower, and when alkali concn surpasses certain value, generally be the component of NaOH when surpassing 0.15 mole, reaction is promptly accelerated rapidly, and reaction heat is difficult in time distribute, temperature sharply rises in the reaction object, make volatility of raw material serious, be easy to the portion's of appearance material phenomenon, be difficult for grasping and control, the quality of the wayward product of industrial production, and be unsuitable for suitability for industrialized production.
The objective of the invention is to improve in the past production method, more be applicable to industrial production to reach by change to make the feed way in the sulphonated acetone formaldehyde polycondensates production process and add suitable catalyzer.
The present invention realizes like this; Press formaldehyde 0.8-1.10 mole, acetone 0.35-0.60 mole, S-WAT 0.10-0.15 mole, the batching of the water of Sodium Pyrosulfite 0.085-0.15 mole and 2-4 mole.Earlier S-WAT hydrolysis and stirring are warming up to 50-60 ℃, again the mixed solution of formaldehyde, acetone and Sodium Pyrosulfite is joined in batches and heated up in 50-60 ℃ the sodium sulfite aqueous solution, formaldehyde, acetone and Sodium Pyrosulfite have begun pre-reaction before carrying out polycondensation, promptly existing part formaldehyde and Sodium Pyrosulfite reaction are converted into sodium hydroxymethane sulfonate, discharge the part heat simultaneously, make entire reaction steady.In carrying out reaction process, want the adding speed of strict control formaldehyde, acetone and Sodium Pyrosulfite mixed solution, be as the criterion, for reaction heat energy is in time distributed, also can use water quench simultaneously so that the temperature of whole reaction system is not more than 70 ℃.Mixed solution adds 20-70 minute the time that needs, after mixed solution adds 50-70 ℃ of down reaction 0.5-3 hour, subsequently again 80-120 ℃ of reaction 1-3 hour down, reduce to 25-30 ℃ after, formic acid (HCOOH) by oxidation of formaldehyde generates is neutralized to P with whole reaction system
HValue is 7-9, descends with 0-300 ℃ of oven for drying also with the levigate sulphonated acetone formaldehyde polycondensates finished product that just makes of mortar at 100-150 ℃ then.Generate formic acid and with in the formic acid and all will to produce sodium formiate be a kind of effective ingredient by the side reaction oxidation of formaldehyde.
Characteristics of the present invention are: above-mentioned prepared in reaction sulphonated acetone formaldehyde polycondensates, and grout in the petroleum drilling well shaft fixing technology had fall dehydration and dissemination preferably, be qualified grout flow improver.Principal feature is that this polycondensate is in manufacturing processed, make the catalyzer of polycondensation by the alkali of S-WAT hydrolysis generation, thereby remove from and add highly basic KOH and NaOH makes catalyzer, the secondth, entire reaction steadily is the basicity by the consumption control of adjusting S-WAT and adjustment whole reaction system, thus the degree of control polycondensation.
Technology provided by the present invention is compared following advantage with technology in the past: 1, reaction comes controls reaction speed by the mixed solution that adds formaldehyde, acetone and Sodium Pyrosulfite in the regular hour scope step by step, make the catalyzer of polycondensation by the alkali of S-WAT hydrolysis generation, reacting balance not only, and be easy to control; 2, the highly basic that need not to add NaOH and KOH and so on is made catalyzer, and in the reaction process, the starting material volatilization is less, thereby has reduced production cost, is suitable for industrialized production simultaneously; 3, this product is through lab investigation and test in place, is cement additive preferably.
The invention will be further described now to lift the example of two groups of five laboratory experiments:
Embodiment 1
S-WAT Na with 0.15 mole
2SO
3Water H with 2.5 moles
2O puts into and has thermometer, reflux cooler, in the 250ml reaction flask of dropping funnel and agitator, constantly stirs and makes Na
2SO
3Hydrolysis, heating simultaneously, when rising to 50 ℃, temperature stops heating, it is 1.06 moles in formaldehyde that formaldehyde, acetone and Sodium Pyrosulfite are mixed with mixed solution in following ratio, 0.41 mole in acetone, 0.086 mole of Sodium Pyrosulfite, in 45 minutes, add in the reaction flask in batches, add the back and reacted 0.5 hour down, and then reacted 1.5 hours down, be cooled to room temperature and be neutralized to P with formic acid at 95 ℃ in 70 ℃
H8, oven dry is levigate under 120 ℃ temperature then, gets product called after SAF-1.
Embodiment 2
The water input of 0.11 mole S-WAT and 3 moles is had in the reaction flask of 250ml of thermometer, reflux cooler dropping funnel and agitator, under agitation be warming up to 60 ℃ and stop heating, formaldehyde with 0.957 mole, 0.44 the acetone of mole, 0.135 the Sodium Pyrosulfite of mole is formed mixed solution, joins in 40 minutes in the reaction flask in batches, mixed solution adds the back and reacted 0.5 hour down at 70 ℃, reacted 2 hours down in 95 ℃ then, reduce to room temperature and be neutralized to P with formic acid again
H8 dry the levigate finished product SAF-2 of getting under 120 ℃.
More than two embodiment can be regarded as one group, record the grout of admixture SAF-1 and SAF-2 by API standard 10, (Jiaxing G class g cement pigment content ω/c=0.44) stable performance, as each data of table 1, visible SAF-1 and SAF-2 all have good drag reduction effect to cement.
Second group of embodiment gets three experiments, device as top two experiments, and method is also close, and just slightly some changes and also draws qualified product and result preferably for prescription and base case, and embodiment 3,4,5 sees Table 2 and compares:
The API standard is pressed in second group of experiment, records and is mixed with SAF-3, SAF-4 and SAF-5 grout, and the G class g cement is produced in Jiaxing, water cement ratio 0.44, and the performance of its grout is as shown in table 3.
By two groups of experiments and the sulphonated acetone formaldehyde polycondensates that generated carry out performance analysis and simulated experiment draws as drawing a conclusion:
1, this production method is feasible, can industrially produce, and reduces cost simultaneously.
2, can significantly improve the flowability of grout, improve pumping efficiency, reduce pump pressure.
3, reduce watering quantity, improved stabilized current characteristic, reduce denseness.
4, be widely used in drilling well shaft fixing technology, the sulphonated acetone formaldehyde polycondensates of producing with this kind method is good grout flow improver.
Claims (2)
1, a kind of manufacture method of sulphonated acetone formaldehyde polycondensates drops into acetone, formaldehyde, sulphite and water in the reaction flask by a certain percentage, reacts under catalyst action, dries levigately then, it is characterized in that S-WAT (Na
2SO
3) proportioning of 0.10-0.15 mole and water 2-4 mole, drop in the reaction flask, constantly stir and make its hydrolysis and generate sodium bisulfite, produce the catalyzer of highly basic (NaOH) simultaneously as polycondensation, heat temperature raising is to 50-60 ℃, again with formaldehyde 0.8-1.10 mole, the mixed solution of acetone 0.35-0.60 mole and Sodium Pyrosulfite 0.085-0.15 mole proportioning, join in the above-mentioned sodium sulfite aqueous solution in batches, after mixed solution adds, under 50-70 ℃ temperature, reacted 0.5-3 hour, and then reacted 1-3 hour under being warming up to 80-120 ℃, after temperature is reduced to 25-30 ℃, use the formic acid (HCOOH) that generates by oxidation of formaldehyde with the system neutralization, to P
HWhen value is 7-9, dry levigate making.
2, the manufacture method of sulphonated acetone formaldehyde polycondensates according to claim 1 is characterized in that the side reaction oxidation of formaldehyde generates in formic acid and the formic acid and the sodium formiate that all produces is a kind of effective ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 91102863 CN1066448A (en) | 1991-05-08 | 1991-05-08 | The manufacture method of sulphonated acetone formaldehyde polycondensates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 91102863 CN1066448A (en) | 1991-05-08 | 1991-05-08 | The manufacture method of sulphonated acetone formaldehyde polycondensates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1066448A true CN1066448A (en) | 1992-11-25 |
Family
ID=4905784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 91102863 Pending CN1066448A (en) | 1991-05-08 | 1991-05-08 | The manufacture method of sulphonated acetone formaldehyde polycondensates |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1066448A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1315977C (en) * | 2003-05-16 | 2007-05-16 | 韩文峰 | Oil layer protecting drilling fluid without clay |
| CN100355854C (en) * | 2005-11-22 | 2007-12-19 | 刘伟 | Dispersion dehydration-reducing agent for oil field well cementation and its preparing method |
| CN100383169C (en) * | 2006-04-21 | 2008-04-23 | 华南理工大学 | The preparation method of cyclohexanone-formaldehyde resin |
| CN100415675C (en) * | 2003-12-31 | 2008-09-03 | 吴霖秀 | High efficiency aliphatic sulfonate water reducing agent and method for preparing same |
| CN100430331C (en) * | 2007-06-05 | 2008-11-05 | 江苏海润化工有限公司 | Continuous production process of efficient aliphatic concrete water reducing agent |
| CN101845131A (en) * | 2010-05-21 | 2010-09-29 | 焦作建工集团有限公司 | Preparation method of high-efficiency water reducing agent |
| CN102060463A (en) * | 2010-12-03 | 2011-05-18 | 山东宏艺科技股份有限公司 | Low-cost concrete antifreezing pumping aid and preparation method thereof |
| CN102515610A (en) * | 2011-12-05 | 2012-06-27 | 马鞍山中海新材料有限公司 | Aliphatic series high efficiency slushing agent and preparation method thereof |
| CN103570268A (en) * | 2012-07-25 | 2014-02-12 | 天津滨海新区庚海精细化工有限公司 | Preparation technology for concrete water reducer |
| CN105990526A (en) * | 2016-02-23 | 2016-10-05 | 华南理工大学 | Lignin sulfonated formaldehyde-acetone condensation compound dispersed poly(3,4-ethylenedioxythiophene) conductive compound and preparation and application thereof |
| CN108503745A (en) * | 2017-02-25 | 2018-09-07 | 北京丰乐宝科技有限公司 | A kind of preparation method of polymerization carbonylation hydramine |
| CN111004514A (en) * | 2019-11-29 | 2020-04-14 | 东莞泰和沥青产品有限公司 | an asphalt modifier |
-
1991
- 1991-05-08 CN CN 91102863 patent/CN1066448A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1315977C (en) * | 2003-05-16 | 2007-05-16 | 韩文峰 | Oil layer protecting drilling fluid without clay |
| CN100415675C (en) * | 2003-12-31 | 2008-09-03 | 吴霖秀 | High efficiency aliphatic sulfonate water reducing agent and method for preparing same |
| CN100355854C (en) * | 2005-11-22 | 2007-12-19 | 刘伟 | Dispersion dehydration-reducing agent for oil field well cementation and its preparing method |
| CN100383169C (en) * | 2006-04-21 | 2008-04-23 | 华南理工大学 | The preparation method of cyclohexanone-formaldehyde resin |
| CN100430331C (en) * | 2007-06-05 | 2008-11-05 | 江苏海润化工有限公司 | Continuous production process of efficient aliphatic concrete water reducing agent |
| CN101845131A (en) * | 2010-05-21 | 2010-09-29 | 焦作建工集团有限公司 | Preparation method of high-efficiency water reducing agent |
| CN101845131B (en) * | 2010-05-21 | 2012-10-03 | 焦作建工集团有限公司 | Preparation method of high-efficiency water reducing agent |
| CN102060463B (en) * | 2010-12-03 | 2012-07-25 | 山东宏艺科技股份有限公司 | Low-cost concrete antifreezing pumping aid and preparation method thereof |
| CN102060463A (en) * | 2010-12-03 | 2011-05-18 | 山东宏艺科技股份有限公司 | Low-cost concrete antifreezing pumping aid and preparation method thereof |
| CN102515610A (en) * | 2011-12-05 | 2012-06-27 | 马鞍山中海新材料有限公司 | Aliphatic series high efficiency slushing agent and preparation method thereof |
| CN102515610B (en) * | 2011-12-05 | 2013-08-07 | 马鞍山中海新材料有限公司 | Aliphatic series high efficiency water reducing agent and preparation method thereof |
| CN103570268A (en) * | 2012-07-25 | 2014-02-12 | 天津滨海新区庚海精细化工有限公司 | Preparation technology for concrete water reducer |
| CN105990526A (en) * | 2016-02-23 | 2016-10-05 | 华南理工大学 | Lignin sulfonated formaldehyde-acetone condensation compound dispersed poly(3,4-ethylenedioxythiophene) conductive compound and preparation and application thereof |
| CN105990526B (en) * | 2016-02-23 | 2018-04-13 | 华南理工大学 | A kind of Sulphonation of Lignin acetonformaldehyde condensation product disperses poly- 3,4 ethylenedioxy thiophene electrically conductive composite and preparation and application |
| CN108503745A (en) * | 2017-02-25 | 2018-09-07 | 北京丰乐宝科技有限公司 | A kind of preparation method of polymerization carbonylation hydramine |
| CN111004514A (en) * | 2019-11-29 | 2020-04-14 | 东莞泰和沥青产品有限公司 | an asphalt modifier |
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