CN109265359A - A kind of side chain type water-soluble poly-quaternary ammonium salt and preparation method thereof - Google Patents
A kind of side chain type water-soluble poly-quaternary ammonium salt and preparation method thereof Download PDFInfo
- Publication number
- CN109265359A CN109265359A CN201811233118.3A CN201811233118A CN109265359A CN 109265359 A CN109265359 A CN 109265359A CN 201811233118 A CN201811233118 A CN 201811233118A CN 109265359 A CN109265359 A CN 109265359A
- Authority
- CN
- China
- Prior art keywords
- quaternary ammonium
- ammonium salt
- side chain
- type water
- preparation
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pest Control & Pesticides (AREA)
- Polymers & Plastics (AREA)
- Agronomy & Crop Science (AREA)
- Medicinal Chemistry (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)
Abstract
The invention discloses side chain type water-soluble poly-quaternary ammonium salts and preparation method thereof as shown in formula.After under alkaline condition substitution reaction occurs for ethanol amine and long-chain chloralkane, reaction solution replaces with 3- tolysulfonyl oxygen methyl -3- ethyl-oxetane again without processing generates the monomer containing tertiary amine group, which occurs cationic ring opening copolymer with hydrophilic monomer under the action of initiator and coinitiator and handle to obtain side chain type water-soluble poly-quaternary ammonium salt through halide.Such polyquaternium structure novel, low toxicity have the function of good water-soluble and stronger bacteriostasis antibiosis, and non-foam generates in use, has broad application prospects in fields such as industrial circulation water treatment, personal care articles, papermaking, coating, intermetallic composite coating and textiles.
Description
Technical field
The present invention relates to a kind of side chain type water-soluble poly-quaternary ammonium salts and preparation method thereof, belong to field of fine chemical.
Background technique
Industrial bactericide refers in industrial circle to the preparation killed or suppressed growth of microorganism, and industrially uses
Fungicide, bacteriostatic agent, preservative, mould inhibitor, algicide etc. are referred to as industrial bactericide, and application field mainly includes industrial cycle
Water process, intermetallic composite coating, pulping and paper-making, oil field, coating, adhesive, the cleaning of a shield and polymer emulsion etc..Industrial bactericide
It generally can be divided into oxidative bactericide and non-oxidative bactericide two major classes, quaternary ammonium salt fungicide is the surface of a kind of antibiotic property
Activating agent is one of most widely used non-oxidative bactericide.Now widely used quaternary ammonium salt fungicide belongs to organic
There is more foam when easily dissolution is migrated, used, poor chemical stability, with certain physiological-toxicity and skin irritatin in small molecule
The disadvantages of property.With the progress of science and technology and the raising of living standards of the people, people ask material safety and environmental pollution
Topic is increasingly paid close attention to, and the research and development of new efficient, low bubble, less toxic quaternary ammonium salt bactericide become focus.
Quaternary ammonium salt macromolecular is the main means to solve the above problems, compared with small molecule quaternary ammonium salt, macromolecule
Quaternary ammonium salt has many advantages, such as: it is not easy dissolution migration, good durability, low bubble and hypotoxicity etc..Quaternary ammonium salt macromolecular
Method first is that preparing polyquaternium by monomer polymerization or copolymerization, polyquaternium, which refers to, contains multiple quaternary ammonium salt bases in molecule
The polymer of group, quaternary ammonium salt group are distributed on high molecular side chain or main chain by covalent bond mode.Polyquaternium purposes
Than wide, the multi-purpose conditioner etc. for making personal-care supplies of presently commercially available polyquaternium product, such as polyquaternium -7, polyquaternary amine
Salt -10 and Merquat 280 etc..Minority is applied to the polyquaternium products in antibacterial field, such as polyquaternium -1, though have compared with
Strong bactericidal effect is simultaneously used widely in contact lens care solution, but still it is growing to be insufficient for more areas
The market demand, it is therefore necessary to develop new polyquaternary amine salt Antibacterial Products.
Patent CN105523946B discloses a kind of polyquaternium anti-biotic material and preparation method thereof, will modify with halides
Monomer polymerization after form polymer precursor, add tertiary amine carry out quaternary ammonium reaction prepare polyquaternium high molecular material；Specially
Sharp CN106084203B uses above-mentioned same method, and coinitiator is changed to polyethylene glycol, makes water-soluble preferable polyethylene glycol
Segment is embedded into material, increases the water solubility of material, to obtain a kind of water soluble block polyquaternium macromolecule material
Material.Although the polyquaternium anti-biotic material of above method preparation has good anti-microbial property, master used in synthesis process
The disadvantages of wanting raw material includes double halides, and there are reaction selectivity difference and higher costs, limits it to a certain extent and answers
With.
The present invention is directed to the shortcomings that quaternary ammonium salt bactericide and development trend, is introduced polymerizable groups by MOLECULE DESIGN
In small molecule quaternary ammonium salt structure precursor, then it is prepared for by the cationic ring opening copolymer and quaternization reaction with hydrophilic monomer
A kind of novel side chain type water-soluble poly-quaternary ammonium salt.
Summary of the invention
The purpose of the present invention is to provide a kind of novel polyquaternium and preparation method thereof, polyquaternary amines of the present invention
Salt and preparation method thereof has the advantage that polyquaternium 1) of the invention has good anti-microbial property, can be used for commercial sterilization
Agent field；2) preparation process is simply controllable, strong operability, environmentally protective；3) polyquaternium prepared by the present invention dissolves out migration
Rate is low, is easy degradation, belongs to the compound of low toxic and environment-friendly type；4) polyquaternium prepared by the present invention has good water-soluble
Property, non-foam generates in use.
Quaternary ammonium salt is a kind of non-oxidative bactericide with cation group, and it is permanent that biocidal efficacies are stablized, if logical
It crosses polymerization methods and prepares polyphosphazene polymer quaternary ammonium salt and be possible to obtain that polyfunctional group, quaternary ammonium salt molecular mobility ratio be low, anti-microbial property
The fungicide product of excellent, low foam in use process, good water solubility.Currently, the report of this respect is few, the present invention is by dividing
Polymerizable groups are introduced into small molecule quaternary ammonium salt structure precursor by son design, then by opening with the cation of hydrophilic aqueous monomers
Ring copolymerization and quaternization reaction are prepared for a kind of novel side chain type water-soluble poly-quaternary ammonium salt.
A kind of novel polyquaternium provided by the invention, structural formula are (I):
Wherein:
R is C8~C22 alkyl；M and n is natural number greater than 1, and m > n；X is Cl or Br；
The example of the compound of formula (I) includes following compounds, but not limited to this:
Formula (I) compound reaction route provided by the invention can be used following reaction equation to indicate:
The preparation method of formula (I) compound provided by the invention comprises the following steps that
1) tertiary amine that substitution reaction generates hydroxyl occurs under alkaline condition for long-chain chloralkane and ethanol amine；
2) the above-mentioned reaction solution 1) obtained is directly added into 3- tolysulfonyl oxygen methyl -3- ethyl-oxa- ring without processing
Butane carries out substitution reaction, through being recrystallized to give the monomer containing tertiary amine group；
3) it is above-mentioned 2) gained monomer initiator and coinitiator effect under with 3- ethyl -3- methylol-oxetanes
Cationic ring opening copolymer occurs, then handles to obtain the aqueous solution of target compounds of formula (I) through halide.
Long-chain chloralkane and ethanol amine reaction process used catalyst are potassium iodide or sodium iodide；Solvent for use is selected from N,
Dinethylformamide, toluene, methylene chloride, tetrahydrofuran, preferably n,N-Dimethylformamide and tetrahydrofuran；Alkali used
For tertiary amine, secondary sterically hindered amines；Preferably triethylamine, the dosage of alkali are selected from 1.1~1.5 times of the amount of long-chain chloralkane substance.
Initiator used in polymerization reaction is boron trifluoride ether；Coinitiator is selected from ethylene glycol, 1,4-butanediol, 1,5- penta
Glycol, 1,6- hexylene glycol, glycerine, preferably ethylene glycol and Isosorbide-5-Nitrae butanediol.
The preparation method of formula (I) compound provided by the invention, entire preparation method is simply controllable, strong operability, preparation
Process waste is few, environmentally protective.
Specific embodiment
The present invention will be further illustrated by following nonlimiting examples.
The preparation of double ten alkyl tertiary amines of embodiment 1:3- ethyl-oxetane -3- methoxyethyl
Equipped in churned mechanically 500mL four-hole bottle, 7.6g ethanol amine, 44.0g chloro decane, 220mL tetrahydro is added
Furans, 30.4g triethylamine, 0.2g potassium iodide are heated to 50~60 DEG C and react 8 hours, and TLC detection display reaction is completed, will be anti-
It answers liquid temperature to be down to 25~30 DEG C, adds 33.7g 3- tolysulfonyl oxygen methyl -3- ethyl-oxetane and 12.6g
Triethylamine, insulation reaction 24 hours, reaction solution was extracted with ethyl acetate after water stirring is added, and took off after the washing of combined ethyl acetate layer
Molten, 50% ethyl alcohol recrystallization is added in residue, obtains the pale yellow acicular crystal of 39.5g after dry, yield 72%, and content >=
98.0%.1H NMR(CDCl3) δ: 4.23~4.51 (m, 4H), 3.82 (s, 2H), 3.35 (t, 2H), 2.63 (t, 4H), 2.28
(t, 2H), 1.64 (m, 2H), 1.30~1.50 (m, 32H), 0.89 (m, 9H).
The preparation of embodiment 2:3- ethyl-oxetane -3- methoxyethyl double hexadecyl tertiary amine
In churned mechanically 500mL four-hole bottle is housed, addition 7.6g ethanol amine, 65.0g chloro-hexadecane, 180mL N,
Dinethylformamide, 30.4g triethylamine, 0.3g potassium iodide are heated to 50~60 DEG C and react 12 hours, and TLC detection display is anti-
It should complete, reacting liquid temperature is down to 25~30 DEG C, add 33.7g 3- tolysulfonyl oxygen methyl -3- ethyl-oxa- ring
Butane and 12.6g triethylamine, insulation reaction 24 hours, reaction solution was extracted with ethyl acetate after water stirring is added, and merged acetic acid second
Precipitation after ester layer washing, residue are added 95% ethyl alcohol recrystallization, obtain 47.5g buff powder after dry, yield 63% contains
Amount >=98.0%.1H NMR(CDCl3) δ: 4.20~4.48 (m, 4H), 3.79 (s, 2H), 3.23 (t, 2H), 2.45 (t, 4H),
2.16 (t, 2H), 1.52 (m, 2H), 1.28~1.51 (m, 56H), 0.90 (m, 9H).
Embodiment 3: the preparation of compound (I a)
In the 250mL four-hole bottle equipped with mechanical stirring and nitrogen protection device, addition 0.70g boron trifluoride ether,
0.16g ethylene glycol and 25mL anhydrous methylene chloride are cooled to 0~5 DEG C, keep that 27.8g 3- ethyl-oxygen is added dropwise at this temperature
Double ten alkyl tertiary amines of azetidine -3- methoxyethyl and 22.0g 3- ethyl -3- methylol-oxetanes 100mL dichloro
Dichloromethane continues to stir at this temperature 15 hours after being added dropwise, and 1g deionized water, the anhydrous sulphur of 2g are added into reaction solution
Sour sodium and 10g diatomite filter after stirring half an hour, and 220mL deionized water is added after removing methylene chloride in filtrate, are transferred to and have
In the 500mL four-hole bottle of mechanical stirring and air-breather, it is passed through methyl chloride gas under stirring, it is small to continue stirring 1 after the completion of ventilation
When after be passed through nitrogen, cross and filter out mechanical admixture, obtain 260g light yellow solution, polyquaternium content >=20.0%.
Embodiment 4: the preparation of compound (I b)
In the 500mL four-hole bottle equipped with mechanical stirring and nitrogen protection device, addition 0.70g boron trifluoride ether,
0.23g 1,4-butanediol and 25mL anhydrous methylene chloride are cooled to 0~5 DEG C, keep that 28.8g 3- second is added dropwise at this temperature
Base-oxetanes -3- methoxyethyl double hexadecyl tertiary amine and 22.0g 3- ethyl -3- methylol-oxetanes
120mL dichloromethane solution continues to stir at this temperature 15 hours after being added dropwise, and 1g deionization is added into reaction solution
Water, 3g anhydrous sodium sulfate and 15g diatomite filter after stirring half an hour, and 500mL deionization is added after removing methylene chloride in filtrate
Water is transferred in the 1L four-hole bottle with mechanical stirring and air-breather, and methyl chloride gas is passed through under stirring, is continued after the completion of ventilation
Stirring is passed through nitrogen after 1 hour, cross and filter out mechanical admixture, obtain 530g light yellow solution, polyquaternium content >=10.0%.
Embodiment 5: the preparation of compound (I c)
In the 500mL four-hole bottle equipped with mechanical stirring and nitrogen protection device, addition 0.70g boron trifluoride ether,
0.23g 1,4-butanediol and 25mL anhydrous methylene chloride are cooled to 0~5 DEG C, keep that 28.8g 3- second is added dropwise at this temperature
Base-oxetanes -3- methoxyethyl double hexadecyl tertiary amine and 22.0g 3- ethyl -3- methylol-oxetanes
120mL dichloromethane solution continues to stir at this temperature 15 hours after being added dropwise, and 1g deionization is added into reaction solution
Water, 3g anhydrous sodium sulfate and 15g diatomite filter after stirring half an hour, and 500mL deionization is added after removing methylene chloride in filtrate
Water is transferred in the 1L four-hole bottle with mechanical stirring and air-breather, and methyl bromide gas is passed through under stirring, is continued after the completion of ventilation
Stirring is passed through nitrogen after 1 hour, cross and filter out mechanical admixture, obtain 525g light yellow solution, polyquaternium content >=10.0%.
Embodiment 6: the antibiotic effect test of side chain type water-soluble poly-quaternary ammonium salt
Gram-positive bacteria staphylococcus aureus (SA) is selected in experiment, and Gram-negative bacteria Escherichia coli (EC) are as survey
Try bacterium, take activation after bacterial strain, be inoculated in liquid nutritional culture solution, cultivated in 37 DEG C of shaking tables 24 hours it is spare.Every kind
4 groups of experiments, blank control, I a of sample, I b of sample, I c of sample are in test.I a of sample weighs 25mg, sample I b and I c weigh 50mg
(polyquaternium content is 5mg) is respectively put into 250mL conical flask (except blank group), and 100mL PBS buffer solution is added
24 hours bacterium solutions are cultivated with 1mL, is placed in vibrate 1 hour in 30 DEG C of shaking tables 1mL supernatant is taken to make gradient dilution, using plate meter
The clump count of number method measurement viable bacteria.The calculation formula of antibiotic rate are as follows:
Test result is as follows for antibiotic effect shown in table:
Claims (6)
1. a kind of side chain type water-soluble poly-quaternary ammonium salt, which is characterized in that its chemical structural formula is shown below:
Wherein: R is C8 ~ C22 alkyl；M and n is natural number greater than 1, and m > n；X is Cl or Br.
2. the preparation method of side chain type water-soluble poly-quaternary ammonium salt as described in claim 1, which is characterized in that steps are as follows: 1)
The tertiary amine that substitution reaction generates hydroxyl occurs under alkaline condition for long-chain chloralkane and ethanol amine；2) it is above-mentioned 1) obtain it is anti-
It answers liquid without processing, is directly added into 3- tolysulfonyl oxygen methyl -3- ethyl-oxetane and carries out substitution reaction, tied again
Crystalline substance obtains the monomer containing tertiary amine group；3) it is above-mentioned 2) gained monomer under the action of initiator and coinitiator with 3- ethyl -3-
Methylol-oxetanes handles to obtain the aqueous solution of target compounds of formula through halide after cationic ring opening copolymer occurs.
3. the preparation method of side chain type water-soluble poly-quaternary ammonium salt according to claim 2, which is characterized in that used in step 1)
Solvent is selected from n,N-Dimethylformamide, toluene, methylene chloride, tetrahydrofuran, and alkali used is selected from tertiary amine, secondary sterically hindered amines, alkali
Dosage be selected from 1.1 ~ 1.5 times of amount of long-chain chloralkane substance；Used catalyst is selected from potassium iodide or sodium iodide.
4. the preparation method of side chain type water-soluble poly-quaternary ammonium salt according to claim 3, which is characterized in that the solvent N,
Dinethylformamide and tetrahydrofuran.
5. the preparation method of side chain type water-soluble poly-quaternary ammonium salt according to claim 3, which is characterized in that three second of alkali
Amine and diisopropyl ethyl amine.
6. the preparation method of side chain type water-soluble poly-quaternary ammonium salt according to claim 2, which is characterized in that used in step 3)
Initiator is boron trifluoride ether；Coinitiator is selected from ethylene glycol, 1,4-butanediol, 1,5-PD, 1,6- hexylene glycol, the third three
Alcohol, preferably ethylene glycol and Isosorbide-5-Nitrae butanediol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811233118.3A CN109265359B (en) | 2018-10-22 | 2018-10-22 | Side chain type water-soluble polyquaternary ammonium salt and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811233118.3A CN109265359B (en) | 2018-10-22 | 2018-10-22 | Side chain type water-soluble polyquaternary ammonium salt and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109265359A true CN109265359A (en) | 2019-01-25 |
| CN109265359B CN109265359B (en) | 2021-09-03 |
Family
ID=65193766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811233118.3A Active CN109265359B (en) | 2018-10-22 | 2018-10-22 | Side chain type water-soluble polyquaternary ammonium salt and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109265359B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113384758A (en) * | 2021-06-18 | 2021-09-14 | 海思盖德(苏州)生物医学科技有限公司 | Anticoagulation coating composition and preparation method and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010116713A1 (en) * | 2009-04-06 | 2010-10-14 | 株式会社ブリヂストン | Organosilicon compound, and rubber composition, tire, primer composition, coating composition and adhesive each using the organosilicon compound |
| JP2012057107A (en) * | 2010-09-10 | 2012-03-22 | Bridgestone Corp | Rubber composition, vulcanized rubber, and tire |
| CN105523946A (en) * | 2016-01-13 | 2016-04-27 | 苏州睿研纳米医学科技有限公司 | Polycation quaternary ammonium salt high polymer material and preparation method thereof |
| CN106084203A (en) * | 2016-06-20 | 2016-11-09 | 苏州睿研纳米医学科技有限公司 | A kind of water soluble block polyquaternary ammonium salt macromolecular material and preparation method thereof |
| WO2017112865A1 (en) * | 2015-12-22 | 2017-06-29 | Modernatx, Inc. | Compounds and compositions for intracellular delivery of agents |
-
2018
- 2018-10-22 CN CN201811233118.3A patent/CN109265359B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010116713A1 (en) * | 2009-04-06 | 2010-10-14 | 株式会社ブリヂストン | Organosilicon compound, and rubber composition, tire, primer composition, coating composition and adhesive each using the organosilicon compound |
| JP2012057107A (en) * | 2010-09-10 | 2012-03-22 | Bridgestone Corp | Rubber composition, vulcanized rubber, and tire |
| WO2017112865A1 (en) * | 2015-12-22 | 2017-06-29 | Modernatx, Inc. | Compounds and compositions for intracellular delivery of agents |
| CN105523946A (en) * | 2016-01-13 | 2016-04-27 | 苏州睿研纳米医学科技有限公司 | Polycation quaternary ammonium salt high polymer material and preparation method thereof |
| CN106084203A (en) * | 2016-06-20 | 2016-11-09 | 苏州睿研纳米医学科技有限公司 | A kind of water soluble block polyquaternary ammonium salt macromolecular material and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| KURT, PINAR ETAL: "Contact biocidal polymeric surface modifiers: polyurethanes containing 2,2-substituted -1,3-propylene oxide soft blocks with alkylammonium side chains", 《PMSE PREPRINTS》 * |
| KURT, PINAR ETAL: "Highly effective biomimetic contact biocidal polyurethanes as polymeric surface modifiers (PSMs)", 《PMSE PREPRINTS》 * |
| PINAR KURT ETAL: "Highly Effective Contact Antimicrobial Surfaces via Polymer Surface Modifiers", 《LANGMUIR》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113384758A (en) * | 2021-06-18 | 2021-09-14 | 海思盖德(苏州)生物医学科技有限公司 | Anticoagulation coating composition and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109265359B (en) | 2021-09-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Patale et al. | O, N-carboxymethyl chitosan–zinc complex: A novel chitosan complex with enhanced antimicrobial activity | |
| US20210259243A1 (en) | Anti-microbial polymer incorporating a quaternary ammonium group | |
| CN102131836A (en) | Antimicrobial polymers and coatings | |
| CN104592459B (en) | A kind of hud typed long acting antibiotic emulsion and preparation method thereof | |
| JP2001504531A (en) | Antibacterial polymer | |
| Gozzelino et al. | Quaternary ammonium monomers for UV crosslinked antibacterial surfaces | |
| CN107383283A (en) | A kind of structural type antimicrobial acrylic emulsion and its preparation method and application | |
| CN102942812B (en) | Imidazolium salt type high polymer antibacterial agent with ultraviolet crosslinking function and preparation method of antibacterial agent | |
| CN106750056A (en) | A kind of triclosan amphipathic nature polyalcohol nano-particle and its preparation method and antibacterial applications | |
| WO2019159865A1 (en) | Molded body | |
| CN109265359A (en) | A kind of side chain type water-soluble poly-quaternary ammonium salt and preparation method thereof | |
| CN102875814A (en) | Polysiloxane, preparation method, application and bacteriacide containing same | |
| WO1994001474A1 (en) | Polymerizable monomer, polymer thereof, and process for producing the same | |
| CN108219065B (en) | A kind of betaine type antibacterial finishing agent and preparation method thereof | |
| CN109771314A (en) | Long-acting anti-, antibacterial wet tissue of one kind and preparation method thereof | |
| CN107099031B (en) | A kind of heat resist modification polyhexamethylene guanide and its preparation method and application | |
| US8491878B2 (en) | Sanitizing formulation | |
| WO1994014872A1 (en) | Polycationic polymer and polycationic bactericidal/algicidal agent | |
| CN109796543A (en) | A kind of preparation method of antibacterial carboxymethyl chitosan and its application in nursing ointment | |
| CN109467513A (en) | A kind of end group type macromolecular quaternary ammonium salt and preparation method thereof | |
| CN109400871B (en) | Quaternary ammonium salt of monodisperse octadecyl three-arm polyglycol ether and preparation method thereof | |
| US4830851A (en) | Polymeric halophors | |
| DE69521161T2 (en) | Polyvinyl alcohol film, process for its production and laminate | |
| CN107207448A (en) | Antimicrobe compound, its preparation method and the product comprising the Antimicrobe compound | |
| CN110201603B (en) | Cationic surfactant and preparation method thereof |
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 |