WO2023087579A1 - Procédé de synthèse de carbamidine de polyoléfine bactéricide macromoléculaire - Google Patents

Procédé de synthèse de carbamidine de polyoléfine bactéricide macromoléculaire Download PDF

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Publication number
WO2023087579A1
WO2023087579A1 PCT/CN2022/080262 CN2022080262W WO2023087579A1 WO 2023087579 A1 WO2023087579 A1 WO 2023087579A1 CN 2022080262 W CN2022080262 W CN 2022080262W WO 2023087579 A1 WO2023087579 A1 WO 2023087579A1
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parts
add
polyolefin
heat
macromolecular
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PCT/CN2022/080262
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English (en)
Chinese (zh)
Inventor
赵晴晴
韩爱芹
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山东志存科技有限公司
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Publication of WO2023087579A1 publication Critical patent/WO2023087579A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • 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

Definitions

  • the invention relates to a synthesis process of a bactericide, in particular to a synthesis process of a macromolecule bactericide-polyolefin carbazine.
  • bacteria and viruses are ubiquitous.
  • Common bacteria include Escherichia coli, Staphylococcus, Streptococcus, Pseudomonas aeruginosa, Proteus, etc. , nose, and pharynx, and some live in the intestines and urethra.
  • Salmonella, Staphylococcus aureus, Vibrio parahaemolyticus, Escherichia coli, etc. can cause food poisoning in varying degrees. Therefore, it is particularly necessary to develop a fungicide that can be used on the skin surface and in food packaging, so that it has long-acting broad-spectrum antibacterial properties and has the advantages of safe use and green production.
  • the common fungicides with similar functions and safe and non-toxic side effects on the market are mainly products containing guanidine groups such as polyhexamethylene monoguanidine and polyhexamethylene biguanide, which have changed the chlorine content of the original fungicides. Or the disadvantage of containing heavy metal ions, which greatly improves the safety of use.
  • guanidine groups such as polyhexamethylene monoguanidine and polyhexamethylene biguanide
  • the disadvantage of containing heavy metal ions which greatly improves the safety of use.
  • the application scenarios and usage methods of these two products are different, resulting in limitations in use and limited popularization and application.
  • the synthesis of biguanides needs to be carried out in organic solvents, reducing the production safety.
  • the purpose of the present invention is to address the above-mentioned defects in the prior art, and to provide a synthesis process of macromolecular bactericidal polyolefin carbazine, which combines the monoguanide structure and the biguanide structure in the same macromolecule, and multifunctional block copolymerization form, a new fungicide was synthesized.
  • the present invention mentions a kind of synthetic technique of macromolecular sterilization-polyolefin carbazine, and its technical scheme is to comprise the following steps, by weight:
  • the obtained solution is the polyolefin carbacilidine macromolecular fungicide of the present invention.
  • the above-mentioned initiator is azobisisobutyronitrile.
  • the synthesis technique of the macromolecule bactericidal-polyolefin carbazine mentioned in the present invention is: comprising the following steps, in parts by weight:
  • the obtained solution is the polyolefin carbacilidine macromolecular fungicide of the present invention.
  • Fig. 1 is embodiment of the present invention 1 in the bacteriostatic zone test comparison picture of Escherichia coli;
  • Fig. 2 is embodiment 2 in the bacteriostatic zone test contrast picture of Escherichia coli
  • Fig. 3 is embodiment 3 in the bacteriostatic zone test comparison picture of Escherichia coli
  • Fig. 4 is embodiment 1 in the antibacterial zone test contrast picture of Staphylococcus aureus
  • Fig. 5 is the comparison picture of embodiment 2 in the antibacterial zone test of staphylococcus aureus
  • Figure 6 is a comparison picture of the inhibition zone test of Staphylococcus aureus in Example 3.
  • Embodiment 1 polyolefin carbacilidine macromolecule fungicide, its preparation method is:
  • the obtained solution is the polyolefin carbacilidine macromolecular fungicide of the present invention.
  • Embodiment 2 polyolefin carbazine macromolecule fungicide, its preparation method is:
  • the obtained solution is the polyolefin carbacilidine macromolecular fungicide of the present invention.
  • Embodiment 3 polyolefin carbacilidine macromolecule fungicide, its preparation method is:
  • the obtained solution is the polyolefin carbacilidine macromolecular fungicide of the present invention.
  • the process of the present invention makes it contain monoguanidine group and biguanide group in the macromolecule at the same time, so as to achieve the following purposes: 1) it can quickly kill microorganisms on the environment or object surface with a lower concentration; 2) it is safe to use, The product does not contain chlorine, heavy metals, or organic solvents; 3) When it stays on the skin surface, it will not harm the human body; 4) The production is green and safe, and does not produce three wastes; 5) It is easy to use and does not require complex compounding process, which can achieve satisfactory results.
  • the present invention is through internal performance experiment, and process is as follows:
  • Bactericidal performance evaluation Escherichia coli and Staphylococcus aureus were selected to test the bactericidal performance, and the bactericidal test was divided into two types: the inhibition zone test and the bactericidal rate test.
  • Solid medium 400mL 1.2g beef extract, 2.0g sodium chloride, 6.0g agar powder, 4.0g peptone, adjust the pH to about 7.2 with 10% sodium hydroxide, and autoclave at 121°C for 20min. In the actual experiment, determine the configuration amount of solid medium and the number of petri dishes according to the number of samples to be tested.
  • 4Secondary inoculation Pipette 1mL of the cultured bacteria solution into the other two bottles of liquid culture solution, and put them in a heating shaker for 2-4 hours.
  • Bacterial culture test inhibition zone prepare a sterilized petri dish and mark it. Add 50 ⁇ L of the bacteria to be tested to each Petri dish. Pour an equivalent amount of solid culture medium into the Petri dish to completely cover it, shake it evenly, add small round paper pieces at each concentration after solidification, and drop 10 ⁇ L or 50 ⁇ L of fungicides of different concentrations on the paper piece, with sterilized pure medium in the middle. Water makes a blank. Put it in a 28-35°C incubator, turn it over after 2 hours, and incubate for 12-24 hours.
  • Solid medium 400mL 1.2g beef extract, 2.0g sodium chloride, 6.0g agar powder, 4.0g peptone, adjust the pH to about 7.2 with 10% sodium hydroxide, and autoclave at 121°C for 20min. In the actual experiment, determine the configuration amount of solid medium and the number of petri dishes according to the number of samples to be tested.
  • 4Secondary inoculation Pipette 1mL of the cultured bacteria solution into the other two bottles of liquid culture solution, and put them in a heating shaker for 2-4 hours.
  • Bacterial culture test sterilization rate Prepare the sterilized petri dish and mark it. Add 50 ⁇ L of the bacteria to be tested and 1 mL of fungicides of different concentrations into the petri dish. Pour an appropriate amount of solid medium into the Petri dish to completely cover it, shake it well, put it into an incubator at 28-35°C after solidification, turn it over after 2 hours, and incubate for 12-24 hours.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un procédé de synthèse d'une carbamidine de polyoléfine bactéricide macromoléculaire. La solution technique comprend les étapes suivantes consistant : 1) à ajouter de l'hexaméthylènediamine et de l'acrylate d'éthyle dans une cuve réactionnelle, à chauffer tout en agitant, et à ajouter un initiateur ; 2) à poursuivre le chauffage, à ajouter du dicyandiamide et du chlorhydrate de guanidine qui sont mélangés de manière uniforme, et à ajouter au goutte à goutte de l'acide chlorhydrique comme catalyseur à une température constante ; 3) à chauffer plusieurs fois, et à réaliser une réaction à température constante ; 5) une fois la réaction terminée, à ajouter au goutte au goutte de l'eau claire dans la cuve réactionnelle, et à agiter complètement ; et 6) à ajuster la valeur du pH entre 6 à 9 afin d'obtenir un bactéricide macromoléculaire de carbamidine de polyoléfine. La présente invention présente les effets bénéfiques suivants : 1) les micro-organismes dans l'environnement ou à la surface d'un objet peuvent être rapidement tués jusqu'à une concentration relativement basse ; 2) le produit peut être utilisé en toute sécurité puisque le produit ne contient ni chlore ni métaux lourds, et aucun solvant organique n'est inclus ; 3) aucun dommage n'est causé au corps humain lorsque le produit reste à la surface de la peau ; 4) une production non polluante et en toute sécurité est obtenue, et il n'y a pas de production de gaz résiduaires, d'eaux usées et de résidus de déchets ; et 5) l'utilisation est pratique, et un résultat d'utilisation satisfaisant peut être obtenu sans nécessiter de processus de préparation complexe.
PCT/CN2022/080262 2021-11-18 2022-03-11 Procédé de synthèse de carbamidine de polyoléfine bactéricide macromoléculaire WO2023087579A1 (fr)

Applications Claiming Priority (2)

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CN202111369437.9 2021-11-18
CN202111369437.9A CN114369188A (zh) 2021-11-18 2021-11-18 一种大分子杀菌剂-聚烯烃卡巴嘧啶的合成工艺

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WO2023087579A1 true WO2023087579A1 (fr) 2023-05-25

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1350022A (zh) * 2000-10-19 2002-05-22 上海塑杰科技有限公司 一种多元胺与胍盐聚合物及其制备方法
CN106800652A (zh) * 2017-01-26 2017-06-06 上海富元塑胶科技有限公司 胍类齐聚物及其制备方法与键合于通用聚合物分子链上的应用
WO2021024075A1 (fr) * 2019-08-07 2021-02-11 3M Innovative Properties Company Articles contenant un polymère contenant du guanidinyle réticulé et leurs utilisations

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1282698C (zh) * 2002-03-15 2006-11-01 上海塑杰科技有限公司 一种聚烯烃功能化母粒及其制备方法和应用
CN101962442B (zh) * 2009-07-21 2013-03-27 铜陵高聚生物科技有限公司 一种盐酸聚六亚甲基双胍的制备方法
CN109371500A (zh) * 2018-10-30 2019-02-22 中国工程物理研究院核物理与化学研究所 一种抗菌提铀纤维及其制备方法
CA3121644A1 (fr) * 2018-11-30 2020-06-04 Dilcem Kimya Ve Denismanlik Ith. Ihr. San. Tic. Ltd. Sti. Masque, pansement, culotte, soutien-gorge, mouchoir, tampon, tampon de recurage, vetement chirurgical jetable et draps chirurgicaux jetables tisses, non tisses, en coton, en polye thylene, en polypropylene et en polystyrene melanges avec du coton non tisse, presentant des proprietes antimicrobiennes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1350022A (zh) * 2000-10-19 2002-05-22 上海塑杰科技有限公司 一种多元胺与胍盐聚合物及其制备方法
CN106800652A (zh) * 2017-01-26 2017-06-06 上海富元塑胶科技有限公司 胍类齐聚物及其制备方法与键合于通用聚合物分子链上的应用
WO2021024075A1 (fr) * 2019-08-07 2021-02-11 3M Innovative Properties Company Articles contenant un polymère contenant du guanidinyle réticulé et leurs utilisations

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