CN105315459A - Preparation method for poly(guanidine hydrochloride adipate - Google Patents
Preparation method for poly(guanidine hydrochloride adipate Download PDFInfo
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- CN105315459A CN105315459A CN201410589775.7A CN201410589775A CN105315459A CN 105315459 A CN105315459 A CN 105315459A CN 201410589775 A CN201410589775 A CN 201410589775A CN 105315459 A CN105315459 A CN 105315459A
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- guanidine hydrochloride
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- hexanodioic acid
- adipate
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Abstract
The invention relates to a preparation method for poly(guanidine hydrochloride adipate). The preparation method includes the steps that adipic acid and guanidine hydrochloride are mixed to be even, heated and molten, wherein the heating temperature ranges from 120 DEG C to 160 DEG C; a catalyst is added; a molecular weight regulator is added; the water removing step is adopted in the whole reaction process, after the reaction is completed, the mixture is immediately added to absolute ethyl alcohol, cooled to room temperature, re-crystallized and filtered, and then poly(guanidine hydrochloride adipate) is obtained. According to poly(guanidine hydrochloride adipate), poly-guanidine disinfectant is structurally improved, electron withdrawing group acyl is introduced to enable the positive electricity of the guanidine group to be higher, and therefore the sterilization capacity of poly(guanidine hydrochloride adipate) is higher.
Description
Technical field
The present invention relates to a kind of preparation method containing guanidine polymer, specifically a kind of preparation method of poly-hexanodioic acid base guanidine hydrochloride.
Background technology
Present sterilant kind is on the market a lot, and the mechanism of action is different, and scope and the effect of sterilization are also not quite similar.But all there is the defect of self, such as, toxic side effect is large, bactericidal range is little, speed of action is slow, price is high.Have broad-spectrum containing guanidine polymer, effective concentration is low, and speed of action is fast, stable in properties, premium properties soluble in water, can use at normal temperatures, antibacterial for a long time, have no side effect, non-corrosiveness, colourless, odorless, nontoxic, not fire, not quick-fried, use safety, moderate, convenient transportation, can be described as best sterilant.Common, example hydrochloric acid polyhexamethylene guanidine (biguanides) and hydrochloric acid Polyethoxyolefin acidic group guanidine class, CN1357235A, CN101731257A etc.The sterilization mechanism containing guanidine polymer with it is that guanidine radicals has very high activity, and in positive polarity, it can rapid adsorption be on the cytolemma of the thalline of negatively charged, and the splitting function of T suppression cell virus, makes it lose reproductive performance.But what have is weak containing guanidine polymer sterilizing ability, can not meet productive life needs.
Summary of the invention
The object of this invention is to provide the preparation method containing guanidine polymer that a kind of sterilizing ability is strong,
The i.e. preparation method of poly-hexanodioic acid base guanidine hydrochloride.
The object of the present invention is achieved like this:
Hexanodioic acid, Guanidinium hydrochloride are mixed, heating and melting, Heating temperature 120-160 DEG C; Add catalyzer; Add molecular weight regulator; Whole reaction process all carries out a point water step, after reaction terminates, adds immediately in dehydrated alcohol, cooling room temperature, and recrystallization, filters and obtain poly-hexanodioic acid base guanidine hydrochloride;
The mol ratio of hexanodioic acid, Guanidinium hydrochloride, catalyzer and molecular weight regulator is 1:1:0.01-0.05:0.02-0.06;
Used catalyst is tosic acid, the vitriol oil, phosphoric acid;
Molecular weight regulator used is thiohydracrylic acid, the different monooctyl ester of 3-thiohydracrylic acid;
Heating temperature in described step 1) is 120 DEG C.
The invention has the beneficial effects as follows:
The present invention gathers hexanodioic acid base guanidine hydrochloride, structurally improves poly-guanidine class sterilizing agent, introduces electron-withdrawing group acyl group and makes the positive polarity of guanidine radicals larger, so its sterilizing ability is just stronger.
Embodiment
Hexanodioic acid, Guanidinium hydrochloride mix by the preparation method of poly-hexanodioic acid base guanidine hydrochloride in the container that temperature method, water trap and condenser are housed, heating and melting, Heating temperature 120-160 DEG C, and optimal reaction temperature is 120 DEG C; Add catalyzer, used catalyst is tosic acid, the vitriol oil, phosphoric acid; Divide water; Add molecular weight regulator, molecular weight regulator used is thiohydracrylic acid, the different monooctyl ester of 3-thiohydracrylic acid; After reaction terminates, add immediately while hot in dehydrated alcohol, cooling room temperature, recrystallization, filters and obtains poly-hexanodioic acid base guanidine hydrochloride.The mol ratio of hexanodioic acid, Guanidinium hydrochloride, catalyzer and molecular weight regulator is 1:1:0.01-0.05:0.02-0.06.
Below by specific embodiment, the present invention will be described, should be understood that in order to illustrate be only to explain the present invention, not limit its content.
In the three-necked bottle (500ml) that thermometer, water trap and condenser are housed, add hexanodioic acid (142.12g), Guanidinium hydrochloride (95.53g), heat 128 DEG C, after melting, stir, add 1.72g to this methylsulfonic acid, stir 2.5 hours, add 2.12g thiohydracrylic acid, after point water terminates, being joined by mixed solution is while hot equipped with in 450ml dehydrated alcohol, stirs, after dissolving completely, cooling room temperature, spend the night, filter, obtain poly-hexanodioic acid guanidine hydrochloride.
In the three-necked bottle (500ml) that thermometer, water trap and condenser are housed, add hexanodioic acid (142.12g), Guanidinium hydrochloride (95.53g), heat 125 DEG C, after melting, stir, add the 1.5g vitriol oil, stir 2.3 hours, add the different monooctyl ester of 2.3g thiohydracrylic acid, after point water terminates, being joined by mixed solution is while hot equipped with in 500ml dehydrated alcohol, stirs, after dissolving completely, cooling room temperature, left undisturbed overnight, filters, obtains poly-hexanodioic acid base guanidine hydrochloride.
In the three-necked bottle (500ml) that thermometer, water trap and condenser are housed, add hexanodioic acid (142.12g), Guanidinium hydrochloride (95.53g), heat 126 DEG C, after melting, stir, add 1.8g strong phosphoric acid, stir 2 hours, add the different monooctyl ester of 2.3g thiohydracrylic acid, after point water terminates, being joined by mixed solution is while hot equipped with in 550ml dehydrated alcohol, stirs, after dissolving completely, cooling room temperature, left undisturbed overnight, filters, obtains poly-hexanodioic acid base guanidine hydrochloride.
In the three-necked bottle (500ml) that thermometer, water trap and condenser are housed, add hexanodioic acid (142.12g), Guanidinium hydrochloride (95.53g), heat 142 DEG C, after melting, stir, add 2.58g to this methylsulfonic acid, stir 2 hours, add the different monooctyl ester of 3.4g thiohydracrylic acid, after point water terminates, being joined by mixed solution is while hot equipped with in 500ml dehydrated alcohol, stirs, after dissolving completely, cooling room temperature, spend the night, filter, obtain poly-hexanodioic acid guanidine hydrochloride.
In the three-necked bottle (500ml) that thermometer, water trap and condenser are housed, add hexanodioic acid (142.12g), Guanidinium hydrochloride (95.53g), heat 150 DEG C, after melting, stir, add 2.2g strong phosphoric acid, stir 2.5 hours, add 2.54g thiohydracrylic acid, after point water terminates, being joined by mixed solution is while hot equipped with in 500ml dehydrated alcohol, stirs, after dissolving completely, cooling room temperature, spend the night, filter, obtain poly-hexanodioic acid guanidine hydrochloride.
Claims (5)
1. a preparation method for poly-hexanodioic acid base guanidine hydrochloride, is characterized in that: hexanodioic acid, Guanidinium hydrochloride are mixed, heating and melting, Heating temperature 120-160 DEG C; Add catalyzer; Add molecular weight regulator; Whole reaction process all carries out a point water step, after reaction terminates, adds immediately in dehydrated alcohol, cooling room temperature, and recrystallization, filters and obtain poly-hexanodioic acid base guanidine hydrochloride.
2. the preparation method of a kind of poly-hexanodioic acid base guanidine hydrochloride according to claim 1, is characterized in that: the mol ratio of hexanodioic acid, Guanidinium hydrochloride, catalyzer and molecular weight regulator is 1:1:0.01-0.05:0.02-0.06.
3. the preparation method of a kind of poly-hexanodioic acid base guanidine hydrochloride according to claim 1, is characterized in that: used catalyst is tosic acid, the vitriol oil, phosphoric acid.
4. the preparation method of a kind of poly-hexanodioic acid base guanidine hydrochloride according to claim 1, is characterized in that: molecular weight regulator used is thiohydracrylic acid, the different monooctyl ester of 3-thiohydracrylic acid.
5. the preparation method of a kind of poly-hexanodioic acid base guanidine hydrochloride according to claim 1, is characterized in that: the Heating temperature in described step is 120 DEG C.
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| CN201410589775.7A CN105315459B (en) | 2014-10-29 | 2014-10-29 | A kind of preparation method of polyadipate base guanidine hydrochloride |
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| CN201410589775.7A CN105315459B (en) | 2014-10-29 | 2014-10-29 | A kind of preparation method of polyadipate base guanidine hydrochloride |
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| CN105315459B CN105315459B (en) | 2017-09-26 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110746595A (en) * | 2019-11-01 | 2020-02-04 | 吉林师范大学 | Preparation method of poly (propylene glycol) guanidine hydrochloride |
| CN110777442A (en) * | 2019-11-06 | 2020-02-11 | 吉林师范大学 | Preparation method of itaconic acid guanidyl styrene copolymerized disinfection fiber |
| WO2020073784A1 (en) * | 2018-10-10 | 2020-04-16 | 桂林新先立抗菌材料有限公司 | Antibacterial polymer and preparation method therefor |
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| SU1641847A1 (en) * | 1988-12-12 | 1991-04-15 | Войсковая часть 75360 | Compound for tentative protection against corrosion |
| SU1728256A1 (en) * | 1988-12-27 | 1992-04-23 | Московский научно-исследовательский и проектно-изыскательский институт "МосводоканалНИИпроект" | Copolymer of alkyleneguanidine salts as a biocide flocculating agent |
| CN1259846A (en) * | 1997-06-13 | 2000-07-12 | 艾夫西亚有限公司 | Biocide organic acid salts of polymeric biguanide |
| CN101173041A (en) * | 2007-10-19 | 2008-05-07 | 华南理工大学 | High molecular weight guanidine salt and polyamine antimicrobial polymeric compounds, producing method and application of the same |
| US20110015304A1 (en) * | 2008-03-28 | 2011-01-20 | Polyrise | Modification of the Surface Chemistry of Macromolecular Species in the Presence of a Conjugated Guanidine |
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2014
- 2014-10-29 CN CN201410589775.7A patent/CN105315459B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1641847A1 (en) * | 1988-12-12 | 1991-04-15 | Войсковая часть 75360 | Compound for tentative protection against corrosion |
| SU1728256A1 (en) * | 1988-12-27 | 1992-04-23 | Московский научно-исследовательский и проектно-изыскательский институт "МосводоканалНИИпроект" | Copolymer of alkyleneguanidine salts as a biocide flocculating agent |
| CN1259846A (en) * | 1997-06-13 | 2000-07-12 | 艾夫西亚有限公司 | Biocide organic acid salts of polymeric biguanide |
| CN101173041A (en) * | 2007-10-19 | 2008-05-07 | 华南理工大学 | High molecular weight guanidine salt and polyamine antimicrobial polymeric compounds, producing method and application of the same |
| US20110015304A1 (en) * | 2008-03-28 | 2011-01-20 | Polyrise | Modification of the Surface Chemistry of Macromolecular Species in the Presence of a Conjugated Guanidine |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020073784A1 (en) * | 2018-10-10 | 2020-04-16 | 桂林新先立抗菌材料有限公司 | Antibacterial polymer and preparation method therefor |
| US11773220B2 (en) | 2018-10-10 | 2023-10-03 | Guilin Zheqi Technology Co., Ltd | Antibacterial polymer and preparation method thereof |
| CN110746595A (en) * | 2019-11-01 | 2020-02-04 | 吉林师范大学 | Preparation method of poly (propylene glycol) guanidine hydrochloride |
| CN110746595B (en) * | 2019-11-01 | 2023-12-22 | 吉林师范大学 | Preparation method of poly (propylene glycol) guanidine hydrochloride |
| CN110777442A (en) * | 2019-11-06 | 2020-02-11 | 吉林师范大学 | Preparation method of itaconic acid guanidyl styrene copolymerized disinfection fiber |
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| CN105315459B (en) | 2017-09-26 |
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Inventor after: Li Chuanbi Inventor after: Liu Chunling Inventor after: Zhang Shoucai Inventor after: Li Fubiao Inventor before: Bai Yunfei |
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Address after: 136100 No. 8, Hongyuan Street, Lingdong Industrial Concentration Zone, Gongzhuling, Siping, Jilin Patentee after: Yunfei Biopharmaceutical (Jilin) Co.,Ltd. Address before: 136001 Office Building of Lingdong Industrial Concentration Area Management Committee, North 1st Street, Lingdong Industrial Concentration Area, Gongzhuling City, Siping City, Jilin Province Patentee before: JILIN YUNFEI PHARMACEUTICAL Co.,Ltd. |
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