CN110746595B - Preparation method of poly (propylene glycol) guanidine hydrochloride - Google Patents
Preparation method of poly (propylene glycol) guanidine hydrochloride Download PDFInfo
- Publication number
- CN110746595B CN110746595B CN201911059343.4A CN201911059343A CN110746595B CN 110746595 B CN110746595 B CN 110746595B CN 201911059343 A CN201911059343 A CN 201911059343A CN 110746595 B CN110746595 B CN 110746595B
- Authority
- CN
- China
- Prior art keywords
- guanidine
- poly
- hydrochloride
- guanidine hydrochloride
- propylene glycol
- 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.)
- Active
Links
- 229960000789 guanidine hydrochloride Drugs 0.000 title claims abstract description 22
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 229920001451 polypropylene glycol Polymers 0.000 title claims abstract description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 9
- UOIDVBITUXAYQD-UHFFFAOYSA-N n,n'-bis(diaminomethylidene)oxamide Chemical compound NC(N)=NC(=O)C(=O)N=C(N)N UOIDVBITUXAYQD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000002844 melting Methods 0.000 claims abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- ZHUWXKIPGGZNJW-UHFFFAOYSA-N 6-methylheptyl 3-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)CCS ZHUWXKIPGGZNJW-UHFFFAOYSA-N 0.000 claims description 6
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical group OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract description 36
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract description 16
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract description 16
- 229960004198 guanidine Drugs 0.000 abstract description 16
- 230000001954 sterilising effect Effects 0.000 abstract description 12
- 239000000645 desinfectant Substances 0.000 abstract description 7
- 125000002252 acyl group Chemical group 0.000 abstract description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 abstract description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 8
- NNDJUNPQOJVCJV-UHFFFAOYSA-N guanidine;hexanedioic acid Chemical compound NC(N)=N.OC(=O)CCCCC(O)=O NNDJUNPQOJVCJV-UHFFFAOYSA-N 0.000 description 7
- 239000003899 bactericide agent Substances 0.000 description 6
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- -1 guanidine compound Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 206010003497 Asphyxia Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- CCVYRYQPQWOOLB-UHFFFAOYSA-N Cl.NC(=N)N.C(=C)C(=O)O Chemical compound Cl.NC(=N)N.C(=C)C(=O)O CCVYRYQPQWOOLB-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920005586 poly(adipic acid) Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention relates to a preparation method of poly (propylene glycol) guanidine hydrochloride. The preparation method comprises the following steps: mixing malonic acid and guanidine hydrochloride uniformly, heating and melting at 120-135 ℃; adding a catalyst and a molecular weight regulator; the whole reaction process is carried out with a water diversion step, and after the reaction is finished, the mixture is immediately added into absolute ethyl alcohol, cooled to room temperature, recrystallized and filtered to obtain the poly (oxalyl guanidine) hydrochloride. The polyacrylic guanidine hydrochloride improves the structure of the guanidine disinfectant, and the positive charges of the guanidine group are higher by introducing the acyl of the electron withdrawing group, so that the sterilizing capability of the guanidine disinfectant is higher.
Description
Technical Field
The invention relates to a preparation method of a guanidine-containing polymer, in particular to a preparation method of poly (acrylic acid) guanidine hydrochloride.
Background
With the increasing standard of living, people pay more attention to the quality of living, pursue healthy living, and the market has been full of sterilizing agents. Although the types of bactericides on the market are various, the sterilizing mechanism, the sterilizing range, the sterilizing effect and the toxic and side effects are different. For example: quaternary ammonium salt, organic sulfur/phosphorus/arsenic bactericides, although the sterilizing effect is better, the toxic and side effects are larger, and some products are forbidden; the sterilization range of the substituted benzene bactericide is small; the antibacterial time of the ethanol and imidazole bactericides is short, and the use is inconvenient; therefore, a bactericide which is high-efficiency, durable, nontoxic, free of side effects, colorless and odorless is needed. The guanidine polymer bactericide has guanidine group in the chemical structural formula, and the guanidine compound has excellent characteristics of bactericidal property, high stability, good biological activity and the like, and the polymer containing the guanidine group is electropositive, so that the guanidine polymer is extremely easy to be adsorbed by various bacteria and viruses which are generally electronegative, thereby inhibiting bacterial division and losing reproductive capacity. In addition, the film formed by the polymer blocks the respiratory canal of the microorganism, so that the microorganism can die quickly by suffocation, and has high bactericidal property.
Disclosure of Invention
The invention aims to provide a preparation method of a guanidine-containing polymer with strong bactericidal capacity, namely a preparation method of poly (guanidine diacid) hydrochloride.
The technical scheme of the invention is as follows:
a preparation method of poly (guanidine sulfate) comprises mixing malonic acid and guanidine hydrochloride uniformly, heating to melt, and heating to 120-135deg.C; a catalyst, a molecular weight regulator is added; the whole reaction process is carried out with a water diversion step, and after the reaction is finished, the mixture is immediately added into absolute ethyl alcohol, cooled to room temperature, recrystallized and filtered to obtain the poly (oxalyl guanidine) hydrochloride.
Malonic acid, guanidine hydrochloride, a catalyst and a molecular weight regulator in a molar ratio of 1:1:0.01-0.05:0.02-0.06.
The catalyst is p-toluenesulfonic acid, concentrated sulfuric acid and phosphoric acid.
The molecular weight regulator is mercaptopropionic acid or isooctyl 3-mercaptopropionate.
The invention has the beneficial effects that:
1. the polyacrylic guanidine hydrochloride improves the structure of the guanidine disinfectant, and the positive charges of the guanidine group are higher by introducing the acyl of the electron withdrawing group, so that the sterilizing capability of the guanidine disinfectant is higher.
2. The poly (guanidine) disinfectant is structurally improved, the electron-withdrawing acyl is introduced into a high polymer long chain, and the electron-withdrawing acyl is added at two sides of the polymer long chain guanidine, so that the guanidine electron of the disinfectant group is attracted by the acyl to ensure that the guanidine positive charge is more positive, and the disinfectant capacity is stronger. Meanwhile, the preparation method of poly (malonic acid) and poly (adipic guanidine hydrochloride) (application publication number CN 105315459A) of the patent of the subject group are adopted for comparison, and as can be seen from fig. 1 and 2: the molecular weight of the poly (guanidine adipate) hydrochloride monomer is smaller than that of the poly (guanidine adipate), and the poly (guanidine adipate) hydrochloride contains more guanidine groups under the condition of the same mass, so that the sterilization effect is better than that of the poly (guanidine adipate).
Drawings
FIG. 1 is a structural formula of a poly (adipic acid) guanidine hydrochloride.
FIG. 2 is a structural formula of poly (oxalyl guanidine) hydrochloride.
FIG. 3 is a graph showing E.coli killing by the poly (oxalylguanidine) hydrochloride and poly (adipate guanidine) hydrochloride.
Detailed Description
The preparation method of the poly (guanidine diacid) hydrochloride comprises the steps of uniformly mixing malonic acid and guanidine hydrochloride in a container provided with a thermometer, a water separator and a condenser, heating and melting, wherein the heating temperature is 120-135 ℃, the optimal reaction temperature is 125 ℃, and the catalyst is p-toluenesulfonic acid, concentrated sulfuric acid or phosphoric acid; dividing water; adding a molecular weight regulator, wherein the molecular weight regulator is mercaptopropionic acid or isooctyl 3-mercaptopropionate; and after the reaction is finished, adding the mixture into absolute ethyl alcohol immediately when the mixture is hot, cooling to room temperature, recrystallizing, and filtering to obtain the poly (guanidine diacid) hydrochloride. The molar ratio of the malonic acid, the guanidine hydrochloride catalyst and the molecular weight regulator is 1:1:0.01-0.05:0.02-0.06.
Example 1 to a three-necked flask (500 mL) equipped with a thermometer, a water separator and a condenser, malonic acid (104.03 g) and guanidine hydrochloride (95.53 g) were added, and after heating to 125℃and melting, 1.63g of p-toluenesulfonic acid was added, followed by stirring, stirring for 3.0 hours and 1.92g of mercaptopropionic acid was added. After the water separation is finished, the mixed solution is added into a beaker filled with 450ml of medical deionized water while the mixed solution is hot, stirred, cooled to room temperature after complete dissolution, and filtered to obtain the poly (oxypolyguanidine) hydrochloride.
Example 2 to a three-necked flask (500 mL) equipped with a thermometer, a water separator and a condenser were added malonic acid (104.03 g) and guanidine hydrochloride (95.53 g), and after heating to 123℃and melting, 1.3g of concentrated sulfuric acid was added with stirring, and 2.8 hours of stirring, 2.02g of isooctyl 3-mercaptopropionate was added. After the completion of the water separation, the mixture was added to a beaker containing 500mL of absolute ethanol while it was still hot, stirred, and after complete dissolution, cooled to room temperature overnight, and filtered to obtain poly (oxalylguanidine) hydrochloride.
Example 3 to a three-necked flask (500 mL) equipped with a thermometer, a water separator and a condenser were added malonic acid (104.03 g) and guanidine hydrochloride (95.53 g), and after heating to 124℃and melting, 1.72g of concentrated phosphoric acid was added with stirring, and 2.8 hours of stirring, 2.02g of isooctyl 3-mercaptopropionate was added. After the completion of the water separation, the mixture was added to a beaker containing 550mL of absolute ethanol while it was still hot, stirred, and after complete dissolution, cooled to room temperature overnight, and filtered to obtain poly (oxalylguanidine) hydrochloride.
Example 4 to a three-necked flask (500 mL) equipped with a thermometer, a water separator and a condenser, malonic acid (104.03 g) and guanidine hydrochloride (95.53 g) were added, and after heating to 130℃and melting, 2.93g of p-toluenesulfonic acid was added, followed by stirring, 2.8 hours, and 2.89g of isooctyl 3-mercaptopropionate was added. After the completion of the water separation, the mixture was added to a beaker containing 500mL of absolute ethanol while it was still hot, stirred, and after complete dissolution, cooled to room temperature overnight, and filtered to obtain poly (oxalylguanidine) hydrochloride.
Example 5 to a three-necked flask (500 mL) equipped with a thermometer, a water separator and a condenser, malonic acid (104.03 g) and guanidine hydrochloride (95.53 g) were added, and after heating to 132℃and melting, 2.03g of concentrated phosphoric acid was added, followed by stirring, stirring for 3.0 hours, and 2.26g of mercaptopropionic acid was added. After the completion of the water separation, the mixture was added to a beaker containing 500mL of absolute ethanol while it was still hot, stirred, and after complete dissolution, cooled to room temperature overnight, and filtered to obtain poly (oxalylguanidine) hydrochloride.
FIG. 3 comparison of E.coli killing with poly (guanidine adipate) and poly (guanidine sulfate) with poly (guanidine sulfate)
From the above graph, the left ∈ represents the sterilization curve of poly (adipic acid guanidine hydrochloride), and the sterilization capability is deteriorated when the liquid medicine is diluted 10 times; the right side of the Chassis shows that the sterilizing ability of the poly (guanidine sulfate) is weakened when the liquid medicine is diluted 15 times, and thus it is inferred that the sterilizing ability of the poly (guanidine sulfate) is 1/3 stronger than that of the poly (guanidine adipate) hydrochloride.
Claims (4)
1. A preparation method of poly (propylene glycol) guanidine hydrochloride is characterized by comprising the following steps: mixing malonic acid and guanidine hydrochloride uniformly, heating and melting at 120-135 ℃; adding a catalyst, heating and stirring for 3 hours, and adding a molecular weight regulator; the whole reaction process is carried out with a water diversion step, and after the reaction is finished, the mixture is immediately added into absolute ethyl alcohol, cooled to room temperature, recrystallized and filtered to obtain the poly (oxalyl guanidine) hydrochloride.
2. The method for preparing the poly (propylene glycol) guanidine hydrochloride according to claim 1, wherein the method comprises the following steps: the molar ratio of malonic acid, guanidine hydrochloride, catalyst and molecular weight regulator is 1:1:0.01-0.05:0.02-0.06.
3. The method for preparing the poly (propylene glycol) guanidine hydrochloride according to claim 1, wherein the method comprises the following steps: the catalyst is p-toluenesulfonic acid, concentrated sulfuric acid and phosphoric acid.
4. The method for preparing the poly (propylene glycol) guanidine hydrochloride according to claim 1, wherein the method comprises the following steps: the molecular weight regulator is mercaptopropionic acid or isooctyl 3-mercaptopropionate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911059343.4A CN110746595B (en) | 2019-11-01 | 2019-11-01 | Preparation method of poly (propylene glycol) guanidine hydrochloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911059343.4A CN110746595B (en) | 2019-11-01 | 2019-11-01 | Preparation method of poly (propylene glycol) guanidine hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110746595A CN110746595A (en) | 2020-02-04 |
| CN110746595B true CN110746595B (en) | 2023-12-22 |
Family
ID=69281741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911059343.4A Active CN110746595B (en) | 2019-11-01 | 2019-11-01 | Preparation method of poly (propylene glycol) guanidine hydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110746595B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386278A (en) * | 1971-07-08 | 1975-03-05 | Dyno Industrier As | Polyamide-epichlorohydrin resins |
| CN101857540A (en) * | 2009-04-09 | 2010-10-13 | 宁波大学 | Method for producing adipic acid, hexamethylenediamine hydrochloride and polyhexamethylene (di)guanidine chloride from nylon-66 through depolymerization |
| CN105315459A (en) * | 2014-10-29 | 2016-02-10 | 吉林云飞医药有限公司 | Preparation method for poly(guanidine hydrochloride adipate |
| CN106380598A (en) * | 2016-10-15 | 2017-02-08 | 石家庄学院 | Synthesis method and application of high-polymer ionic liquid |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA005462B1 (en) * | 2000-05-11 | 2005-02-24 | П.О.Ц. Ойл Индастри Текнолоджи Бератунгсгез.М.Б.Х. | Biocidal polymers based on guanidine salts |
| FR2929281B1 (en) * | 2008-03-28 | 2011-03-11 | Polyrise | MODIFICATION OF THE SURFACE CHEMISTRY OF MACROMOLECULAR SPECIES IN THE PRESENCE OF A CONJUGATED GUANIDINE |
-
2019
- 2019-11-01 CN CN201911059343.4A patent/CN110746595B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386278A (en) * | 1971-07-08 | 1975-03-05 | Dyno Industrier As | Polyamide-epichlorohydrin resins |
| CN101857540A (en) * | 2009-04-09 | 2010-10-13 | 宁波大学 | Method for producing adipic acid, hexamethylenediamine hydrochloride and polyhexamethylene (di)guanidine chloride from nylon-66 through depolymerization |
| CN105315459A (en) * | 2014-10-29 | 2016-02-10 | 吉林云飞医药有限公司 | Preparation method for poly(guanidine hydrochloride adipate |
| CN106380598A (en) * | 2016-10-15 | 2017-02-08 | 石家庄学院 | Synthesis method and application of high-polymer ionic liquid |
Non-Patent Citations (4)
| Title |
|---|
| Structural characterization and antibacterial activity of oligoguanidine;Dafu Wei et al;Materials Science and Engineering C;第29卷;第1776-1780页 * |
| 含胍基抗菌聚合物的合成及应用;张浩 等;化学进展;第31卷(第5期);第681-689页 * |
| 聚六亚甲基胍盐酸盐的合成研究;曾平;谢维跃;蒋健;魏盼中;许筠;;日用化学工业(第11期);第629-632页 * |
| 黄奇然 等.聚六亚甲基盐酸胍在造纸工业中的应用.中国造纸.2011,第30卷(第6期),第32-36页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110746595A (en) | 2020-02-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105601778B (en) | A kind of ring-type halogen amine polymer antibacterial agent containing quaternary ammonium group and its preparation method and application | |
| JPS58148808A (en) | Bactericide | |
| WO1991007184A1 (en) | SUBSTANTIALLY ANHYDROUS COMPLEXES OF PVP and H2O¿2? | |
| KR100196460B1 (en) | Antimicrobial agent containing quaternary ammonium salt | |
| CN103598196A (en) | Biological slime stripping agent for water treatment, and preparation method thereof | |
| CN101962442A (en) | Method for preparing polyhexamethylene biguanidine hydrochloride | |
| CN113383775A (en) | Compound quaternary ammonium salt low-temperature disinfectant and preparation method thereof | |
| SU1192621A3 (en) | Method of producing substituted quinoxalin-2-yl-1,4-dioxidethinylketones | |
| CN110746595B (en) | Preparation method of poly (propylene glycol) guanidine hydrochloride | |
| US4271190A (en) | Guanidinium salts, processes for their manufacture as well as microbicidal preparations containing these compounds | |
| JPS5944283B2 (en) | New microbicides and algaecides | |
| US10189798B2 (en) | Antimicrobial compounds, methods of making the same and articles comprising them | |
| CN115053909B (en) | Bio-based green composite antibacterial agent and preparation method and application thereof | |
| CN113214464B (en) | Antibacterial polyester material and preparation method and application thereof | |
| AU703980B2 (en) | Storage stable biocide composition and process for making the same | |
| JPH04224518A (en) | Novel antibacterial composition and method of its preparation | |
| JP2017043559A (en) | Antibacterial agent composition | |
| CN113632803A (en) | Quaternary ammonium salt complex iodine disinfectant and preparation method thereof | |
| CN111574495B (en) | Water-soluble dibenzo-24-crown-8-based gel and preparation method thereof | |
| JP4052526B2 (en) | Antibacterial resin | |
| JP2007091647A (en) | Antimicrobial dna salt composition | |
| US4207326A (en) | Antimicrobial quaternary pyrazole derivatives | |
| CN111574710B (en) | Dendritic tryptophan compound, preparation method thereof and application thereof as antibacterial agent | |
| JP2000247805A (en) | Inorganic composition having antibacterial and mildew resistant activity, and resin composition having the same activity | |
| JPH07285809A (en) | Antibacterial agent containing quaternary ammonium salt |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |