CN110746595A - Preparation method of poly (propylene glycol) guanidine hydrochloride - Google Patents
Preparation method of poly (propylene glycol) guanidine hydrochloride Download PDFInfo
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- CN110746595A CN110746595A CN201911059343.4A CN201911059343A CN110746595A CN 110746595 A CN110746595 A CN 110746595A CN 201911059343 A CN201911059343 A CN 201911059343A CN 110746595 A CN110746595 A CN 110746595A
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- poly
- guanidine
- hydrochloride
- guanidine hydrochloride
- malonic acid
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- 229960000789 guanidine hydrochloride Drugs 0.000 title claims abstract description 21
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 229920001451 polypropylene glycol Polymers 0.000 title abstract description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 15
- -1 poly (malonic acid) guanidine hydrochloride Chemical compound 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- BTYNVOQLMBUUMS-UHFFFAOYSA-N 2-amino-1h-pyrimidine-4,6-dione Chemical compound NC1=NC(=O)CC(=O)N1 BTYNVOQLMBUUMS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 238000002844 melting Methods 0.000 claims abstract description 4
- 230000008018 melting Effects 0.000 claims abstract description 4
- 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 8
- ZHUWXKIPGGZNJW-UHFFFAOYSA-N 6-methylheptyl 3-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)CCS ZHUWXKIPGGZNJW-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 238000003756 stirring Methods 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 4
- 229960005385 proguanil Drugs 0.000 claims description 4
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract description 27
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 20
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract description 15
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract description 15
- 229960004198 guanidine Drugs 0.000 abstract description 15
- 239000000645 desinfectant Substances 0.000 abstract description 5
- 239000011259 mixed solution Substances 0.000 description 11
- 239000003899 bactericide agent Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 7
- 238000004659 sterilization and disinfection Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 230000001954 sterilising effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 3
- NNDJUNPQOJVCJV-UHFFFAOYSA-N guanidine;hexanedioic acid Chemical compound NC(N)=N.OC(=O)CCCCC(O)=O NNDJUNPQOJVCJV-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 244000005700 microbiome Species 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 230000032683 aging Effects 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
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000007246 mechanism 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
- 239000011148 porous material Substances 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
- 239000000126 substance Substances 0.000 description 1
- 210000000779 thoracic wall Anatomy 0.000 description 1
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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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 (malonic acid) guanidine hydrochloride. The preparation method comprises the following steps: uniformly mixing malonic acid and guanidine hydrochloride, heating and melting at the heating temperature of 120-; adding a catalyst and adding a molecular weight regulator; and (3) carrying out a water separation step in the whole reaction process, immediately adding the water separation step into absolute ethyl alcohol after the reaction is finished, cooling to room temperature, recrystallizing and filtering to obtain the poly (malonylguanidine hydrochloride). The poly (propylene glycol) -guanidine hydrochloride improves the structure of guanidine disinfectants, and introduces electron-withdrawing group acyl to ensure that the guanidine has larger electropositivity, so that the bactericidal capability of the disinfectant is stronger.
Description
Technical Field
The invention relates to a preparation method of a guanidine-containing polymer, in particular to a preparation method of poly (malonic acid) guanidine hydrochloride.
Background
With the increasing living standard, people pay more attention to the quality of life and pursue healthy life, and the full-mesh bactericide on the market is produced. Although the types of the bactericides on the market are various, the sterilization mechanisms, the sterilization ranges, the sterilization effects and the toxic and side effects of the bactericides are different. For example: quaternary ammonium salt, organic sulfur/phosphorus/arsenic bactericides have good bactericidal effect but large toxic and side effects, and some products are forbidden; the substituted benzene bactericide has a small sterilization range; the ethanol and imidazole bactericides have short antibacterial aging and inconvenient use; therefore, a bactericide which is efficient, durable, non-toxic, non-side-effect, colorless and odorless is needed. The guanidine polymer bactericide has guanidine in its chemical structural formula, the guanidine compound has excellent characteristics of bactericidal property, high stability, good biological activity and the like, and the guanidine-containing polymer is electropositive, so that the guanidine polymer bactericide is very easy to be adsorbed by various bacteria and viruses which are usually electronegative, thereby inhibiting bacterial division and leading the guanidine polymer bactericide to lose reproductive capacity. In addition, the film formed by the polymer blocks the respiratory pore passages of microorganisms, so that the microorganisms are rapidly suffocated and die, and the sterilization performance is high.
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 polypropionate guanidine hydrochloride.
The technical scheme of the invention is as follows:
a preparation method of poly (propylene diacid) -guanidine hydrochloride comprises the steps of uniformly mixing malonic acid and guanidine hydrochloride, heating and melting, wherein the heating temperature is 120-; catalyst, adding molecular weight regulator; and (3) carrying out a water separation step in the whole reaction process, immediately adding the water separation step into absolute ethyl alcohol after the reaction is finished, cooling to room temperature, recrystallizing and filtering to obtain the poly (malonylguanidine hydrochloride).
The mol ratio of the malonic acid, the guanidine hydrochloride, the catalyst and the molecular weight regulator is 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 and isooctyl 3-mercaptopropionate.
The invention has the beneficial effects that:
1. the poly (propylene glycol) -guanidine hydrochloride improves the structure of guanidine disinfectants, and introduces electron-withdrawing group acyl to ensure that the guanidine has larger electropositivity, so that the bactericidal capability of the disinfectant is stronger.
2. According to the poly (propylene glycol) guanidine hydrochloride, the structure of a polyguanidine disinfectant is improved, electron-withdrawing acyl is introduced into a high-molecular long chain, and electron-withdrawing acyl is added on two sides of guanidyl of the high-molecular long chain, so that guanidino electrons of a disinfection group are attracted by acyl to enable the positive charge of the guanidyl to be more positive, and the disinfection capacity is higher. The comparison of polypropionic acid with the preparation method of poly (guanidine adipate) hydrochloride (application publication No. CN105315459A) of the subject group patent is also performed, and it can be seen from FIG. 1 and FIG. 2 that: the molecular weight of the poly (malonylguanidine) hydrochloride monomer is smaller than that of poly (adipinyl guanidine) hydrochloride, and under the condition of the same mass, the poly (malonylguanidine) hydrochloride contains more guanidine groups than that of the poly (adipinyl guanidine) hydrochloride, so that the bactericidal effect is better than that of the poly (adipinyl guanidine) hydrochloride.
Drawings
FIG. 1 is a structural formula of poly (biguanide adipate) hydrochloride.
FIG. 2 is a structural formula of poly (malonylguanidine) hydrochloride.
FIG. 3 is a plot of poly (proguanil) -chloride and poly (biguanide) -chloride against Escherichia coli.
Detailed Description
The preparation method of the poly (propylene diacid) -guanidine 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-; water diversion; adding a molecular weight regulator, wherein the molecular weight regulator is mercaptopropionic acid or isooctyl 3-mercaptopropionate; and after the reaction is finished, immediately adding the mixture into absolute ethyl alcohol while the mixture is hot, cooling the mixture to room temperature, recrystallizing the mixture, and filtering the mixture to obtain the poly (propylene glycol) guanidine hydrochloride. The molar ratio of the malonic acid to the guanidine hydrochloride to the catalyst to the molecular weight regulator is 1:1:0.01-0.05:0.02-0.06.
Example 1 malonic acid (104.03g) and guanidine hydrochloride (95.53g) were added to a three necked flask (500mL) equipped with a thermometer, water separator and condenser, heated to 125 ℃ and melted, then stirred, 1.63g p-toluenesulfonic acid was added, stirred for 3.0 hours and 1.92g mercaptopropionic acid was added. And after the water is separated, adding the mixed solution into a beaker filled with 450ml of medical deionized water while the mixed solution is hot, stirring, cooling to room temperature after the mixed solution is completely dissolved, standing overnight, and filtering to obtain the poly (malonic acid) guanidine hydrochloride.
Example 2 malonic acid (104.03g) and guanidine hydrochloride (95.53g) were added to a three necked flask (500mL) equipped with a thermometer, water separator and condenser, heated to 123 ℃ and melted, then stirred, 1.3g of concentrated sulfuric acid was added, stirred for 2.8 hours, and 2.02g of isooctyl 3-mercaptopropionate was added. And after water is separated, adding the mixed solution into a beaker filled with 500mL of absolute ethyl alcohol while the mixed solution is hot, stirring, completely dissolving, cooling to room temperature, standing overnight, and filtering to obtain the poly (malonic acid) guanidine hydrochloride.
Example 3 malonic acid (104.03g) and guanidine hydrochloride (95.53g) were added to a three necked flask (500mL) equipped with a thermometer, trap and condenser, heated to 124 ℃ and melted, then stirred, 1.72g of concentrated phosphoric acid was added, stirred for 2.8 hours, and 2.02g of isooctyl 3-mercaptopropionate was added. And after water is separated, adding the mixed solution into a beaker filled with 550mL of absolute ethyl alcohol while the mixed solution is hot, stirring, completely dissolving, cooling to room temperature, standing overnight, and filtering to obtain the poly (malonic acid) guanidine hydrochloride.
Example 4 malonic acid (104.03g) and guanidine hydrochloride (95.53g) were added to a three necked flask (500mL) equipped with a thermometer, water separator and condenser, heated to 130 ℃ and melted, then stirred, 2.93g p-toluene sulfonic acid was added, stirred for 2.8 hours, and 2.89g isooctyl 3-mercaptopropionate was added. And after water is separated, adding the mixed solution into a beaker filled with 500mL of absolute ethyl alcohol while the mixed solution is hot, stirring, completely dissolving, cooling to room temperature, standing overnight, and filtering to obtain the poly (malonic acid) guanidine hydrochloride.
Example 5 malonic acid (104.03g) and guanidine hydrochloride (95.53g) were added to a three necked flask (500mL) equipped with a thermometer, trap and condenser, heated to 132 ℃ and melted, then stirred, 2.03g of concentrated phosphoric acid was added, stirred for 3.0 hours and 2.26g of mercaptopropionic acid was added. And after water is separated, adding the mixed solution into a beaker filled with 500mL of absolute ethyl alcohol while the mixed solution is hot, stirring, completely dissolving, cooling to room temperature, standing overnight, and filtering to obtain the poly (malonic acid) guanidine hydrochloride.
FIG. 3 is a graph showing Escherichia coli-killing effects of poly (guanidine adipate) hydrochloride and poly (guanidine) hydrochloride
As can be seen from the above figure, the left side ● represents the bactericidal curve of poly (guanidine adipate) hydrochloride, and the bactericidal ability becomes worse when the solution is diluted 10 times; polyproguanil hydrochloride is weakened when the solution is diluted 15 times on the right-side of the chest wall, and it is inferred that the bactericidal activity of the polypropiogliadin hydrochloride is 1/3 stronger than that of the polyhexamethylene guanidine hydrochloride.
Claims (4)
1. A preparation method of poly (malonic acid) guanidine hydrochloride is characterized in that: uniformly mixing malonic acid and guanidine hydrochloride, heating and melting at the heating temperature of 120-; adding a catalyst, heating, stirring for 3 hours, and adding a molecular weight regulator; and (3) carrying out a water separation step in the whole reaction process, immediately adding the water separation step into absolute ethyl alcohol after the reaction is finished, cooling to room temperature, recrystallizing and filtering to obtain the poly (malonylguanidine hydrochloride).
2. The method of claim 1, wherein the poly (proguanil) -malonate is selected from the group consisting of: the molar ratio of the malonic acid to the guanidine hydrochloride to the catalyst to the molecular weight regulator is 1:1:0.01-0.05:0.02-0.06.
3. The method of claim 1, wherein the poly (proguanil) -malonate is selected from the group consisting of: the catalyst is p-toluenesulfonic acid, concentrated sulfuric acid and phosphoric acid.
4. The method of claim 1, wherein the poly (proguanil) -malonate is selected from the group consisting of: the molecular weight regulator is mercaptopropionic acid and isooctyl 3-mercaptopropionate.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386278A (en) * | 1971-07-08 | 1975-03-05 | Dyno Industrier As | Polyamide-epichlorohydrin resins |
| US20030113291A1 (en) * | 2000-05-11 | 2003-06-19 | Schmidt Oskar J. | Biocidal polymers based on guanidine salts |
| 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 |
| US20110015304A1 (en) * | 2008-03-28 | 2011-01-20 | Polyrise | Modification of the Surface Chemistry of Macromolecular Species in the Presence of a Conjugated Guanidine |
| 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 |
-
2019
- 2019-11-01 CN CN201911059343.4A patent/CN110746595B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1386278A (en) * | 1971-07-08 | 1975-03-05 | Dyno Industrier As | Polyamide-epichlorohydrin resins |
| US20030113291A1 (en) * | 2000-05-11 | 2003-06-19 | Schmidt Oskar J. | Biocidal polymers based on guanidine salts |
| US20110015304A1 (en) * | 2008-03-28 | 2011-01-20 | Polyrise | Modification of the Surface Chemistry of Macromolecular Species in the Presence of a Conjugated Guanidine |
| 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 |
|---|
| DAFU WEI ET AL: "Structural characterization and antibacterial activity of oligoguanidine", MATERIALS SCIENCE AND ENGINEERING C, vol. 29, pages 1776 - 1780, XP026322557, DOI: 10.1016/j.msec.2009.02.005 * |
| 张浩 等: "含胍基抗菌聚合物的合成及应用", 化学进展, vol. 31, no. 5, pages 681 - 689 * |
| 曾平;谢维跃;蒋健;魏盼中;许筠;: "聚六亚甲基胍盐酸盐的合成研究", 日用化学工业, no. 11, pages 629 - 632 * |
| 黄奇然 等: "聚六亚甲基盐酸胍在造纸工业中的应用", vol. 30, no. 6, pages 32 - 36 * |
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