CN102698647A - PH sensitive-type gemini surface active agents and synthesis method thereof - Google Patents
PH sensitive-type gemini surface active agents and synthesis method thereof Download PDFInfo
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- CN102698647A CN102698647A CN2012101532139A CN201210153213A CN102698647A CN 102698647 A CN102698647 A CN 102698647A CN 2012101532139 A CN2012101532139 A CN 2012101532139A CN 201210153213 A CN201210153213 A CN 201210153213A CN 102698647 A CN102698647 A CN 102698647A
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- 0 *N(CCN(*)CCN(C(CC1)=O)C1=O)CCN(C(CC1)=O)C1=O Chemical compound *N(CCN(*)CCN(C(CC1)=O)C1=O)CCN(C(CC1)=O)C1=O 0.000 description 1
- REHPZUVFRQHWCP-UHFFFAOYSA-N C=[Br]CCN(C(CC1)=O)C1=O Chemical compound C=[Br]CCN(C(CC1)=O)C1=O REHPZUVFRQHWCP-UHFFFAOYSA-N 0.000 description 1
- DAUYCPHBNCTCKP-UHFFFAOYSA-N CC(CCBr)C(CC(CC1)=O)C1=O Chemical compound CC(CCBr)C(CC(CC1)=O)C1=O DAUYCPHBNCTCKP-UHFFFAOYSA-N 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N O=C(CC1)NC1=O Chemical compound O=C(CC1)NC1=O KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to gemini surface active agents with pH sensitive property. According to the invention, the head groups of the gemini surface active agents respectively contain succinimide, benzopyrrolidone or phthalimide. The three compounds are pH sensitive, and have good surface activity and viscoelasticity. The gemini surface active agents have the critical micelle concentration (CMC) within the range of 10<-7>-10<-3>mol/ L and the lowest surface tension within the range of 25-31mN/ m. As the gemini surface active agents, the compounds have excellent characteristics, and can be independently compounded with other surface active agents and then are widely applied to industrial practice such as household chemicals, pesticide preparations and oil exploitation.
Description
Technical field
The present invention relates to several types of pH responsive type gemini surfactants and synthetic method thereof, belong to field of fine chemical.
Background technology
Surfactant is to add capillary one big type of organic compound that very small amount can reduce solvent greatly.According to traditional sorting technique, surfactant can be divided into four big types of anionic, cationic, nonionic and amphoteric.Nearly two during the last ten years, and gemini type (Shuangzi) surfactant becomes the focus of research because of its excellent characteristic.Compare with traditional list surfactant, gemini type surfactant has lower surface tension, littler critical micelle concentration, higher surperficial usefulness and abundant characteristics such as solution self-assembled structures.
In addition, gemini type surfactant also has some other premium properties, such as outstanding infiltration, emulsification, dispersion, foaming capacity or the like.They also show stronger solubilising power, to the higher patience of high volence metal ion, better anti-microbial property, good ecological environment effect or the like.In addition, the production cost of some gemini type surfactant can be cheaper, and it can reach good effect under low consumption simultaneously.So when commercial production, suitably design synthesis path, can be so that gemini type surfactant to be economical and practical, its following application is estimated can be at industry, agricultural and biological field.
In recent years, various surfactants with sensitive property receive widely and paying close attention to, as: pH sensitivity, responsive to temperature and salt sensitivity etc.Several types of gemini type surfactants of the present invention all have the pH sensitive property; Can be through regulating pH; Obtain dication type, single cationic, nonionic and mixed surfactant; Thereby obtain abundant more surface nature and aggregation behavior, its potential application is also more extensive.
Summary of the invention
The technical problem that the present invention will solve provides a kind of gemini type surfactant and synthetic method thereof of pH responsive type.
For addressing the above problem, pH responsive type gemini surfactant of the present invention, it has following structural formula:
Having two hydrophobic tails couplet and two hydrophilic head bases in this structure, is typical Gemini surface active agent.Wherein, the nitrogen-atoms in the tertiary amine is quaternized easily under acid condition, has tangible pH response characteristic.
The synthetic method of above-mentioned pH responsive type gemini surfactant may further comprise the steps:
(1) succinimide, phthalimide or benzopyrrole alkane ketone and Bromofume are added in the polar solvent, in the presence of exogenously added alkali, in 0 ~ 150 ℃ of reaction 5 ~ 48 hours, separation and purification obtained nitrogen bromoethyl heterocyclic compound;
(2) ethylenediamine and long-chain bromoalkane being added in the polar solvent, in the presence of exogenously added alkali, is catalyst with the KI, and in 60～150 ℃ of reactions 12～96 hours, separation and purification obtained N, the two alkyl ethylenediamines of N ' synthetic; Described long-chain bromoalkane is bromination of n-butane, bromo n-hexane, n-octane bromide, bromo n-decane, bromododecane, bromotetradecane, bromohexadecane or bromo-octadecane;
(3) with nitrogen bromoethyl heterocyclic compound and N; The two alkyl ethylenediamines of N ' were with 2: 1 ~ 6: 1 mol ratio; In the presence of exogenously added alkali and organic solvent; With the KI is catalyst, in 60～150 ℃ of reactions 1 ~ 7 day, reacts the gemini type surfactant that the separation and purification that finishes obtains containing the hydrophilic head base of heterocyclic.
In step (1), (2) or (3), described alkali is one or more in sodium carbonate, potash, caustic alcohol, NaOH, the sodium hydride.
Polar solvent in step (1) or the step (2) is acetonitrile, ethanol, chloroform, N, dinethylformamide, methyl-sulfoxide or their mixture.
In the step (3), described organic solvent is ethanol, acetonitrile, chloroform, N, dinethylformamide or methyl-sulfoxide.
More specifically,
When Y was succinimide, the reaction scheme of said method was:
When Y was phthalimide, the reaction scheme of said method was:
When Y was benzopyrrole alkane ketone, the reaction scheme of said method was:
The present invention has following beneficial effect:
1, the gemini type surfactant that contains the hydrophilic head base of heterocyclic that the present invention synthesized has good pH sensitiveness.
2, the gemini type surfactant of the present invention's preparation is compared with traditional list surfactant, has better surface property.Its ratio of the CMC conventional surfactant hangs down 1 ~ 3 one magnitude, has very high surface-active under the critical micelle concentration.
3, the gemini type surfactant of the present invention preparation has good viscoplasticity, some in addition have excellent biological compatibility.
Description of drawings
The distribution curve of surfactant under condition of different pH of Fig. 1 embodiment 1 preparation.
The surface tension concentration curve of surfactant when different pH of Fig. 2 embodiment 1 preparation.
The specific embodiment
Contain the hydrophilic head base of heterocyclic, pH responsive type gemini type surfactant, general structure is following:
The present invention contains the hydrophilic head base of heterocyclic, pH responsive type gemini type surfactant is selected from following a few compounds:
(1) the head base contains two alkyl ethylenediamine gemini type surfactants of succinimide, (being called for short Di-CnPO);
(2) the head base contains two alkyl ethylenediamine gemini type surfactants of phthalimide, (being called for short Di-CnPh);
(3) the head base contains two alkyl ethylenediamine gemini type surfactants of benzopyrrole alkane ketone, (being called for short Di-CnI).
Following embodiment can make those skilled in the art better understand the present invention, but does not limit the present invention in any way.
Embodiment 1
Head base contains the synthesizing of two octyl ethylenediamines of succinimide, and chemical formula is: C
30H
54N
4O
4, structural formula is:
Step 1: in the 250ml single port flask that reflux condensing tube is housed, add 20g (0.2mol) succinimide and 74.5g Bromofume, and 14g (0.2mol) caustic alcohol, be under the condition of solvent at ethanol, 60 ℃ of stirring reaction 24h.Reaction finishes, and product removes and desolvates through revolving steaming, is eluent with ethyl acetate then, through silica gel column chromatography, can obtain 39.5g white solid nitrogen bromoethyl succinimide, productive rate 95.4%.
Step 2: in the 250ml there-necked flask that reflux condensing tube, constant pressure funnel, thermometer are housed; Add 6.0g (0.1mol) ethylenediamine, 41.0g (0.3mol) potash, 0.17g (0.001mol) KI successively; Stir; Be warming up to 120 ℃, slowly drip 43.1g (0.22mol) bromooctane, reaction 96h.After reaction finished, cooling forwarded product in the conical flask to.After the room temperature cooling, be put in the refrigerator.After treating products solidifying,, and, remove remaining moisture, obtain the thick product of alkylamine the solid oven dry through decompress filter.This thick product is eluent with the benzinum, through column chromatography for separation, can obtain the N of white, the two octyl ethylenediamine of N ' 21.6g, productive rate 76.0%.
Step 3: in the 500ml single port flask that reflux condensing tube is housed; Add 49.4g (0.24mol) nitrogen bromoethyl succinimide, 11.4g (0.04mol) N successively; The two octyl ethylenediamines of N ', 25.2g (0.3mol) sodium carbonate, 0.07g (0.0004mol) KI; Add 200mlDMSO and make solvent, 150 ℃ of stirring reaction 48h.Reaction finishes, and filters pressure reducing and steaming DMSO; Obtain yellow thick product, this thick product is eluent through silica gel column chromatography with benzinum and ethyl acetate mixed solvent; Separate through silica gel column chromatography, can obtain the final objective product: the head base contains two octyl ethylenediamines of succinimide.Products obtained therefrom 19.4g, productive rate 90.8%.
1HNMR(CDCl
3,δ/ppm?relative?to?TMS)：0.88(t,6H),1.29~1.68(m,24H),2.42~2.68(m,20H）,3.59(t,4H)。
ESI-MS: [M+CH
30H+H]
+=567.5, [M+2CH
30H+H]
+=599.4; High resolution mass spectrum shows that the peak at 567.5 places is that target molecule combines a methanol molecules and a hydrionic peak, and the peak at 599.4 places is that target molecule combines two methanol molecules and a hydrionic peak.
The pH sensitive property: find through the pH titration, when pH value of solution less than 3 the time, surfactant molecule exists with the form of dication; When pH value of solution 6.5 between 7.5 the time, molecule exists with single cationic form; When pH value of solution greater than 10.5 the time, surfactant molecule exists with non-ionic form.As shown in Figure 1.Above result shows: this molecule has good pH response characteristic.
Surface-active: can find out that from the surface tension concentration curve of Fig. 2 this surfactant has good surface-active, also have good pH response simultaneously.
Head base contains bishexane base ethylenediamine synthetic of phthalimide, and chemical formula is: C
30H
38N
4O
4, structural formula is:
Step 1: in the 500ml single port flask that reflux condensing tube is housed, add 44g (0.3mol) phthalimide successively, 75g (0.4mol) Bromofume, and 64g (0.6mol) sodium carbonate are solvent with the chloroform, room temperature reaction 12h.Reaction finishes and boils off solvent and unnecessary Bromofume, is eluent with the benzinum, and silica gel column chromatography separates, and can obtain 74g white solid nitrogen bromoethyl phthalimide, productive rate 97%.
Step 2: in the 250ml there-necked flask that reflux condensing tube, constant pressure funnel, thermometer are housed; Add 6.0g (0.1mol) ethylenediamine, 41g (0.3mol) potash, 0.17g (0.001mol) KI successively; Stir; Be warming up to 60 ℃, slowly drip 29.9g (0.22mol) butyl bromide, reaction 24h.After reaction finished, cooling forwarded product in the conical flask to.After the room temperature cooling, be put in the refrigerator.After treating products solidifying,, and, remove remaining moisture, obtain the thick product of alkylamine the solid oven dry through decompress filter.This thick product is eluent with methyl alcohol, through column chromatography for separation, can obtain the N of white, N ' bishexane base ethylenediamine 19.0g, productive rate 83.4%.
Step 3: in the 500ml single port flask that reflux condensing tube is housed; Add 38g (0.15mol) nitrogen bromoethyl phthalimide, 6.9g (0.04mol) N successively; The two butane group ethylenediamines of N ', 16.2g (0.3mol) caustic alcohol, 0.07g (0.0004mol) KI; Add 200ml ethanol and make solvent, 70 ℃ of stirring reaction 120h.Reaction finishes, and filters, and boils off ethanol; Obtain yellow thick product, this thick product is eluent through silica gel column chromatography with benzinum and carrene mixed solvent; Separate through silica gel column chromatography, can obtain the final objective product: the head base contains the bishexane base ethylenediamine of phthalimide.Products obtained therefrom 19.4g, productive rate 93.5%.
1HNMR(CDCl
3,δ/ppm?relative?to?TMS)：0.88(t,6H),1.29~1.68(m,8H),2.43(t,4H),2.52(s,4H),2.70(t,4H),3.76(t,4H),7.70~7.84(m,8H).
ESI-MS: [M+1]
+=519.5, high resolution mass spectrum shows that the peak at 519.5 places is target molecule (Di-C
4Ph) combine a hydrionic peak.
Embodiment 3
Head base contains the synthesizing of two dodecyl ethylenediamines of benzopyrrole alkane ketone, and chemical formula is: C
46H
74N
4O
2, structural formula is:
Step 1: in the 500ml single port flask that reflux condensing tube is housed, add 44g (0.3mol) phthalimide successively, 75g (0.4mol) Bromofume, and 64g (0.6mol) sodium carbonate are solvent with the chloroform, room temperature reaction 12h.Reaction finishes and boils off solvent and unnecessary Bromofume, is eluent with the mixed solvent of benzinum and ethyl acetate, and the silica gel column chromatography separation can obtain 74g white solid nitrogen bromoethyl phthalimide, productive rate 97%.Then, in two mouthfuls of flasks of the 500ml that reflux condensing tube is housed, add 50.8g (0.2mol) nitrogen bromoethyl phthalimide, 200ml acetic acid and 13g (0.2mol) zinc powder successively, 120 ℃ of reaction 5h.Reaction finishes, and removes unnecessary reactant liquor, extracts three times through chloroform and water; Organic facies is removed and is desolvated through anhydrous magnesium sulfate drying, filtration, is eluent with ethyl acetate; Through silica gel column chromatography, can obtain the nitrogen bromo ethyl phenenyl pyrrolizine ketone of 42g white, productive rate 87.5%.
Step 2: in the 250ml there-necked flask that reflux condensing tube, constant pressure funnel, thermometer are housed; Add 6.0g (0.1mol) ethylenediamine, 7.2g (0.3mol) sodium hydride, 0.17g (0.001mol) KI successively; Stir; Be warming up to 80 ℃, slowly Dropwise 5 4.8g (0.22mol) bromododecane reacts 48h.After reaction finished, cooling forwarded product in the conical flask to.After the room temperature cooling, be put in the refrigerator.After treating products solidifying,, and, remove remaining moisture, obtain the thick product of alkylamine the solid oven dry through decompress filter.This thick product is eluent with ethyl acetate, through column chromatography for separation, can obtain the N of white, the two dodecyl ethylenediamine of N ' 27.6g, productive rate 69.6%.
Step 3: in the 500ml single port flask that reflux condensing tube is housed; Add 24g (0.1mol) nitrogen bromo ethyl phenenyl pyrrolizine ketone, 15.9g (0.04mol) N successively; The two dodecyl ethylenediamines of N ', 7.2g (0.3mol) sodium hydride, 0.07g (0.0004mol) KI; Add the 200ml acetonitrile and make solvent, 80 ℃ of stirring reactions 7 days.Reaction finishes, and filters the pressure reducing and steaming acetonitrile; Obtain yellow thick product, this thick product is eluent through silica gel column chromatography with benzinum and ethyl acetate mixed solvent; Separate through silica gel column chromatography, can obtain the final objective product: the head base contains two dodecyl ethylenediamines of benzopyrrole alkane ketone.Products obtained therefrom 26.7g, productive rate 93.3%.
1HNMR(CDCl
3,δ/ppm?relative?to?TMS)：0.88(t,6H),1.29~1.68(m,40H),2.43(t,4H),2.52(s,4H),2.70(t,4H),3.64(t,4H),4.45(s,4H),7.42~7.84(m,8H).
ESI-MS: [M+1]
+=715.6, [2M+23]
+=1452.2; High resolution mass spectrum shows that the peak at 715.6 places is that target molecule combines a hydrionic peak, and the peak at 1452.2 places is the peak that the dliploid of target molecule combines a sodium ion.
Head base contains the synthesizing of two octadecyl ethylenediamines of benzopyrrole alkane ketone, and chemical formula is: C
58H
98N
4O
2, structural formula is:
Step 1: in two mouthfuls of flasks of the 500ml that reflux condensing tube is housed, add 29.4g (0.2mol) phthalimide, 4: 1 mixed liquor of 200ml acetate and hydrochloride, 13g (0.2mol) zinc powder successively, 120 ℃ of reaction 5h.Reaction finishes, and revolves to steam to remove unnecessary reactant liquor, extracts three times through chloroform and water; Organic facies is removed and is desolvated through anhydrous magnesium sulfate drying, filtration, is eluent with ethyl acetate; Through silica gel column chromatography, can obtain the benzopyrrole alkane ketone of 23.3g white, productive rate 87.5%.Then, under nitrogen protection, 14.7g (0.1mol) benzopyrrole alkane ketone is diluted with 50mlDMF, add in two mouthfuls of flasks of 250ml, stir; Get 3.26g content and be 70% sodium hydride, with the 50mlDMF dissolving, disperse, add in the 100ml dropping funel; Under the ice bath, slowly drip the DMF solution of sodium hydride, dropwised in about one hour.After then reacting two hours, this reactant liquor through conduit, is added drop-wise in the there-necked flask that fills 94g (0.5mol) Bromofume, 42g potash (0.3mol); Behind the stirring at room 6h, stop reaction.Reactant liquor revolves to steam through the extraction of chloroform and water or oil pump removes DMF, and the thick product of gained is a white solid.This thick product is crossed post through carrene, can obtain to have a little the target product nitrogen bromo ethyl phenenyl pyrrolizine ketone 11.4g of white, productive rate 47.4%.
Step 2: in the 250ml there-necked flask that reflux condensing tube, constant pressure funnel, thermometer are housed; Add 6.0g (0.1mol) ethylenediamine, 7.2g (0.3mol) sodium hydride, 0.17g (0.001mol) KI successively; Stir; Be warming up to 150 ℃, slowly drip 124.3g (0.22mol) bromo-octadecane, reaction 48h.After reaction finished, cooling forwarded product in the conical flask to.After the room temperature cooling, be put in the refrigerator.After treating products solidifying,, and, remove remaining moisture, obtain the thick product of alkylamine the solid oven dry through decompress filter.This thick product is eluent with ethyl acetate, through column chromatography for separation, can obtain the N of white, the two octadecyl ethylenediamine of N ' 31.6g, productive rate 55.9%.
Step 3: in the 500ml single port flask that reflux condensing tube is housed; Add 24g (0.1mol) nitrogen bromo ethyl phenenyl pyrrolizine ketone, 22.6g (0.04mol) N successively; The two octadecyl ethylenediamines of N ', 7.2g (0.3mol) sodium hydride, 0.07g (0.0004mol) KI; Add the 200ml acetonitrile and make solvent, 80 ℃ of stirring reactions 7 days.Reaction finishes, and filters the pressure reducing and steaming acetonitrile; Obtain yellow thick product, this thick product is eluent through silica gel column chromatography with benzinum and ethyl acetate mixed solvent; Separate through silica gel column chromatography, can obtain the final objective product: the head base contains two octadecyl ethylenediamines of benzopyrrole alkane ketone.Products obtained therefrom 27.7g, productive rate 83.1%.
1HNMR(CDCl
3,δ/ppm?relative?to?TMS)：0.88(t,6H),1.29~1.68(m,64H),2.43(t,4H),2.52(s,4H),2.70(t,4H),3.64(t,4H),4.45(s,4H),7.42~7.84(m,8H).
ESI-MS: [M+1]
+=883.8, [2M+23]
+=1786.8; High resolution mass spectrum shows that the peak at 883.8 places is that target molecule combines a hydrionic peak, and the peak at 1786.6 places is the peak that the dliploid of target molecule combines a sodium ion.
Claims (5)
1.pH responsive type gemini surfactant, its structural formula is:
2. the synthetic method of the said pH responsive type of claim 1 gemini surfactant is characterized in that, comprises the steps:
(1) succinimide, phthalimide or benzopyrrole alkane ketone and Bromofume are added in the polar solvent, in the presence of exogenously added alkali, in 0 ~ 150 ℃ of reaction 5 ~ 48 hours, separation and purification obtained nitrogen bromoethyl heterocyclic compound;
(2) ethylenediamine and long-chain bromoalkane being added in the polar solvent, in the presence of exogenously added alkali, is catalyst with the KI, and in 60～150 ℃ of reactions 12～96 hours, separation and purification obtained N, the two alkyl ethylenediamines of N ' synthetic; Described long-chain bromoalkane is bromination of n-butane, bromo n-hexane, n-octane bromide, bromo n-decane, bromododecane, bromotetradecane, bromohexadecane or bromo-octadecane;
(3) with nitrogen bromoethyl heterocyclic compound and N; The two alkyl ethylenediamines of N ' were with 2: 1 ~ 6: 1 mol ratio; In the presence of exogenously added alkali and organic solvent; With the KI is catalyst, in 60～150 ℃ of reactions 1 ~ 7 day, reacts the gemini type surfactant that the separation and purification that finishes obtains containing the hydrophilic head base of heterocyclic.
3. synthetic method according to claim 2 is characterized in that, the alkali described in step (1), (2) or (3) is one or more in sodium carbonate, potash, caustic alcohol, NaOH, the sodium hydride.
4. according to claim 2 or 3 described synthetic methods, it is characterized in that the polar solvent in step (1) or the step (2) is acetonitrile, ethanol, chloroform, N, dinethylformamide, methyl-sulfoxide or their mixture.
5. according to claim 2 or 3 described synthetic methods, it is characterized in that the organic solvent described in the step (3) is ethanol, acetonitrile, chloroform, N, dinethylformamide or methyl-sulfoxide.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103341338A (en) * | 2013-07-22 | 2013-10-09 | 武汉大学 | PH sensitive-type single-chain surfactants as well as synthetic method thereof |
| CN105655551A (en) * | 2016-01-05 | 2016-06-08 | 扬州大学 | Method for rapidly and separating inorganic nanoparticles |
| CN110467912A (en) * | 2019-09-10 | 2019-11-19 | 肯特催化材料股份有限公司 | A kind of high temperature triggering reverse wetting agent and the preparation method and application thereof |
| CN113774392A (en) * | 2021-08-12 | 2021-12-10 | 上海新阳半导体材料股份有限公司 | Cleaning solution used after chemical mechanical polishing and preparation method thereof |
| CN113789519A (en) * | 2021-08-12 | 2021-12-14 | 上海新阳半导体材料股份有限公司 | Application of post-chemical mechanical polishing cleaning solution |
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| US4174443A (en) * | 1977-12-30 | 1979-11-13 | Gaf Corporation | Aza-bis-lactams |
| EP0183478B1 (en) * | 1984-11-21 | 1990-01-31 | Chevron Research Company | Glycidol modified succinimides |
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| Title |
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| JIANG.Z ET AL: "pH-Responsive Surface Activity and Solubilization with Novel Pyrrolidone-Based Gemini Surfactants", 《LANGMUIR》, vol. 28, no. 18, 8 May 2012 (2012-05-08), pages 7174 - 7181 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103341338A (en) * | 2013-07-22 | 2013-10-09 | 武汉大学 | PH sensitive-type single-chain surfactants as well as synthetic method thereof |
| CN105655551A (en) * | 2016-01-05 | 2016-06-08 | 扬州大学 | Method for rapidly and separating inorganic nanoparticles |
| CN105655551B (en) * | 2016-01-05 | 2017-11-21 | 扬州大学 | A kind of quick method for preparing and separating inorganic nanoparticles |
| CN110467912A (en) * | 2019-09-10 | 2019-11-19 | 肯特催化材料股份有限公司 | A kind of high temperature triggering reverse wetting agent and the preparation method and application thereof |
| CN110467912B (en) * | 2019-09-10 | 2021-06-25 | 肯特催化材料股份有限公司 | High-temperature triggered wetting reversal agent and preparation method and application thereof |
| CN113774392A (en) * | 2021-08-12 | 2021-12-10 | 上海新阳半导体材料股份有限公司 | Cleaning solution used after chemical mechanical polishing and preparation method thereof |
| CN113789519A (en) * | 2021-08-12 | 2021-12-14 | 上海新阳半导体材料股份有限公司 | Application of post-chemical mechanical polishing cleaning solution |
| CN113774392B (en) * | 2021-08-12 | 2023-12-01 | 上海新阳半导体材料股份有限公司 | Cleaning liquid for chemical mechanical polishing and preparation method thereof |
| CN113789519B (en) * | 2021-08-12 | 2024-02-02 | 上海新阳半导体材料股份有限公司 | Application of cleaning liquid after chemical mechanical polishing |
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Application publication date: 20121003 |