CN107344914A - A kind of synthesis technique of antibacterial debonding agent, antibacterial debonding agent and purposes - Google Patents
A kind of synthesis technique of antibacterial debonding agent, antibacterial debonding agent and purposes Download PDFInfo
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- CN107344914A CN107344914A CN201710544936.4A CN201710544936A CN107344914A CN 107344914 A CN107344914 A CN 107344914A CN 201710544936 A CN201710544936 A CN 201710544936A CN 107344914 A CN107344914 A CN 107344914A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/36—Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
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Abstract
A kind of synthesis technique of antibacterial debonding agent, antibacterial debonding agent and purposes, comprise the following steps：Using triethanolamine, thionyl chloride as raw material, in organic solvent, substitution reaction is first carried out, long-chain alkyl tertiary amine is then added in above-mentioned product, carry out quaternization reaction synthetic antimicrobial debonding agent；Antibacterial debonding agent is applied to fluff pulp fibers, antibacterial Time of Fluff Slurry is prepared, can also be applied to antimicrobial form paper for daily use, high life paper；Products obtained therefrom antibacterial effect is good, has preferable softness.
Description
Technical field
The invention belongs to paper making additive technical field, and in particular to a kind of synthesis technique of antibacterial debonding agent, antibacterial solution key
Agent and purposes.
Background technology
With the improvement of people ' s living standards, two tire policies and aging population, sanltary towel, baby's diaper and into
The disposable sanitary articles such as people's incontinence article have obtained quick development.Due to close with human contact, have one to sanitary condition
Fixed requirement, but for manufacturing the material of these disposable products, such as：Time of Fluff Slurry etc., itself does not simultaneously have antibiotic property, and
Substantial amounts of microorganism in natural environment be present, once condition suitably if can amount reproduction, it is possible to cause courses of infection, endanger people
Body health.Therefore, anti-biotic material then product of times turn into new material research and development and product development hot fields.
In addition, with increasingly increase of the people to paper for daily use demand, such as toilet paper, napkin paper, beauty paper, napkin
Deng, while to the quality requirement of paper also more and more higher, higher requirement is especially proposed to sheet softness.But China lives
During being manufactured paper with pulp with paper, the ratio shared by non-wood-fiber and secondary stock is very high, makes the universal feel of these paper for daily uses poor.It is logical
Pliability is improved frequently with corrugated mode, the shortcomings that some paper plants even overcome non-wood pulp domestic paper by being filled with, but imitate
Fruit is unsatisfactory, and effective method is to use softening agent.So softening agent for paper is increasingly taken seriously.It is past, soft
Agent in textile industry using more, but application of the textile softener as substitute in papermaking exist dosage greatly, cost
The disadvantages such as height, effect difference, are rarely used in sheet processing.So necessary research and develop paper special softener.
Researcher is by adding first mainly from the antibacterial and softness of product from the aspect of two both at home and abroad at present
Add antiseptic to improve the antibiotic property of paper, then meet requirement of the paper to pliability by adding softening agent again.With this
Invention correlation technique has：
Li Zhanxiong discloses a kind of antiseptic of fluorine-containing alkyl quaternary ammonium salts in Chinese patent application 201310589419.0, prepared
Method and its application.Fluorine-containing alkyl tertiary amine is made by substitution reaction first, then reacts through quaternization to obtain N- tri-alkoxies
The trifluoro octyl group ammonium halide of silicon propyl group-N, N- dialkyl group ten.The antiseptic has the antibacterial more superior than non-fluorine-containing alkyl quaternary ammonium salts
Efficiency.
Zhang Xiuhuas etc. disclose a kind of Effect of Water Soluble Quaternary Ammonium Salt of Chitosan in Chinese patent application 201410044922.2 and killed
Microbial inoculum and preparation method thereof.Its preparation method is chitosan and Polyethylene Glycol Bisglycidyl Ether open loop alkylated reaction,
Then reaction product and halogenated hydrocarbons are subjected to quaterisation and obtain a kind of chitosan derivatives with quaternary ammonium salt structure.
Chen Huaqun etc. discloses a kind of ester group bi-quaternary ammonium salt fabric sofetening in Chinese patent application 200710070954.X
Agent and preparation method thereof.Using long chain fatty acids or fatty acid ester, triethanolamine, antioxidant, catalyst as raw material, first it is esterified
Or esterification exchanges, the chlorinated compound containing double activated functional group is then added in above-mentioned product, quaterisation is carried out and obtains
To ester group bi-quaternary ammonium salt.
Li Yiping discloses a kind of bisamide quaternary ammonium salt sheet softening agent in Chinese patent application 200910048339.X
And preparation method thereof.Its raw material composition is tristerin, diethylenetriamine and dimethyl suflfate.The softening agent can be used for defending
Raw paper, beauty paper, napkin paper etc., and in preparation process is simple, its synthesis technique is simple, and raw material is easy to get.
Xu Guihong etc. discloses a kind of double alkylamide imidazoline quaternary ammoniums in Chinese patent application 200810025673.7
The preparation method of salt form paper softener.The softening agent is characterised by existing amide-type softness, has quaternary ammonium salt soft special again
The characteristics of new type of paper softening agent of color, have year fiber suction-operated it is strong, interfibrous static friction system can be greatly lowered
Number, and with the smooth characteristic of feel.
Above-mentioned quaternary antiseptic and softening agent are from paper single performance, so as to assign paper antibacterial and soft
Soft characteristic, therefore the antibacterial debonding agent that a kind of existing anti-microbial property of synthesis has flexible nature again has important practical significance.
And relevant report in this respect, it is more deficient at present.
The present invention proposes the method by chemical synthesis, using triethanolamine, thionyl chloride and long-chain alkyl tertiary amine as raw material,
In organic solvent, new antibacterial debonding agent is prepared by substitution and quaternization reaction, is then applied to Time of Fluff Slurry, resists
Bacterial type paper for daily use, high life paper etc., assign the performance of the certain antibacterial of product and softness.
The content of the invention
To overcome above-mentioned the deficiencies in the prior art, it is an object of the invention to provide a kind of synthesis work of antibacterial debonding agent
Skill, antibacterial debonding agent and application thereof, products therefrom is then applied to paper pulp fiber, prepare existing anti-microbial property has softness again
The product of characteristic.
To solve the above problems, the present invention adopts the following technical scheme that：
A kind of synthesis technique of antibacterial debonding agent, antibacterial debonding agent and purposes, comprise the following steps：
First, under the conditions of ice-water bath, organic solvent and triethanolamine are added in three-necked flask, turn on agitator, chlorine is added dropwise
Change sulfoxide, 30 DEG C ~ 35 DEG C, stirring reaction 2h ~ 3h are warming up to after adding, be continuously heating to 60 DEG C ~ 70 DEG C, reaction 2h ~ 3h to nothing
Gas is released, and cooling, crystallization, is filtered and is repeatedly washed with chloroform or absolute ethyl alcohol, dries, obtain intermediate product three（The chloroethenes of 2- bis-
Base）Amine hydrochlorate；
Secondly, to above-mentioned intermediate product three（2- Dichloroethyls）It is molten that the sodium hydroxide that concentration is 5mol/L is added dropwise in amine hydrochlorate
Liquid, the pH value of regulation system then heat to 50 DEG C ~ 60 DEG C and start that long-chain alkyl tertiary amine is added dropwise, heated up after finishing between 6 ~ 9
Continue to react 6h ~ 8h to 80 DEG C ~ 90 DEG C, cooling, crystallization, filter and washed repeatedly with anhydrous sodium sulfate, ethyl acetate and ethanol,
Drying, obtains antibacterial debonding agent；Field of papermaking is then applied to, improves properties of product.
The triethanolamine, the mol ratio of thionyl chloride are：1:3.0~4.5.
The organic solvent is absolute ethyl alcohol, chloroform, toluene, isopropanol.
The long-chain alkyl tertiary amine is N-N dimethyl-octas alkyl tertiary amine, N-N dimethyl hexadecyl bases tertiary amine, N-N dimethyl
Octadecyl tertiary amine.
The intermediate product three（2- Dichloroethyls）The mol ratio of amine hydrochlorate and long-chain alkyl tertiary amine is：1:3.0~4.5.
Described antibacterial debonding agent is the antibacterial debonding agent of tri-long-chain alkyl.
Described antibacterial debonding agent is with three N+The cationic surfactant of ion.
Debonding agent prepared by a kind of synthesis technique of described antibacterial debonding agent, it is characterised in that the antibacterial debonding agent
General structure is as follows：
Wherein, n 7,15,17；
Specific reflection equation is as follows：
1）The synthesis of intermediate product：
2）Quaternization reacts：
Wherein, n 7,15,17.
A kind of purposes of described antibacterial debonding agent, the antibacterial debonding agent are applied to fluff pulp fibers, can also be applied to
The production of antimicrobial form paper for daily use and high life paper；The existing anti-microbial property of paper of gained has the characteristic of softness again.
The invention has the advantages that：
The present invention in organic solvent, passes through substitution reaction synthetic mesophase product three using triethanolamine, thionyl chloride as raw material
（2- Dichloroethyls）Amine hydrochlorate；With intermediate product three（2- Dichloroethyls）Amine hydrochlorate and long-chain alkyl tertiary amine are carried out for raw material
New antibacterial debonding agent is prepared in quaternization reaction；
Several new antibacterial debonding agents are made by the method for chemical synthesis in this product, and first Application is in Time of Fluff Slurry, antibacterial
Type paper for daily use, high life paper etc., products obtained therefrom antibacterial effect is good, and has preferable softness.
This product is by increasing N+The quantity of ion, utilizes N+The antibiotic property of the Antibacterial Mechanism increase antibacterial debonding agent of ion
Energy；
This product has antibacterial debonding agent concurrently certain by increasing the length and quantity of alkyl chain using the hydrophobicity of alkyl chain
Flexible nature.
Brief description of the drawings
Fig. 1 is antibacterial Time of Fluff Slurry of the present invention to the antibacterial activity figure of golden glucose coccus, wherein Fig. 1（a）For blank sample
Antibacterial activity figure of the paper to golden glucose coccus；Fig. 1（b）It is different amounts of antibacterial debonding agent to golden glucose coccus
Antibacterial activity figure；S0、S1、S2、S3Respectively add 0%, 0.578%, 0.867%, 1.156% antibacterial debonding agent.
Fig. 2 is antibacterial Time of Fluff Slurry of the present invention to the antibacterial activity figure of Escherichia coli, wherein Fig. 2（a）For blank sample paper pair
The antibacterial activity figure of Escherichia coli；Fig. 2（b）Antibacterial activity figure for different amounts of antibacterial debonding agent to Escherichia coli；S0、S1、
S2、S3Respectively add 0%, 0.578%, 0.867%, 1.156% antibacterial debonding agent.
Embodiment
The present invention is described in further detail with specific embodiment below in conjunction with the accompanying drawings.
Embodiment 1
A kind of synthesis technique of antibacterial debonding agent, comprises the following steps：
1）Intermediate product --- three（2- Dichloroethyls）The synthesis of amine hydrochlorate
Under the conditions of ice-water bath, 22ml chloroform and 10ml are added into 250ml three-necked flask（0.075mol）Three ethanol
Amine, turn on agitator, by 22ml（0.3mol）Thionyl chloride be slowly dropped to tear drop bottle in reaction solution, there is gas slowly to emit
Go out, tail gas is absorbed with sodium hydroxide solution, after being added dropwise, is to slowly warm up to 30 DEG C, stirring reaction 3h, then gradually heating
To 60 DEG C, 3h is reacted, continues to be heated to no gas releasing, cooling separates out a large amount of white solids, then filtered, and use chloroform
Wash repeatedly, 50 DEG C of drying, obtain white solid；
2）Final product three（2- chlorination octyl dimethylammonio ethyls）Amine（A type antibacterial debonding agents）Synthesis
Under the conditions of ice-water bath, 2g is weighed（0.0083mol）Three（2- Dichloroethyls）Amine hydrochlorate and a certain amount of sodium hydroxide are molten
Liquid is added in three-necked flask, and the pH value of regulation system is 6；Measure 9ml（0.0332mol）N-N dimethyl-octas alkyl tertiary amine in
In tear drop bottle, agitator and heater switch are started, is warming up to 50 DEG C, N-N dimethyl-octa alkyl tertiary amines are slowly added drop-wise to three mouthfuls
In the reaction solution of flask, after being added dropwise, continue to be heated to 80 DEG C, react 8h；, then with anhydrous sodium sulfate, ethyl acetate
Handled with absolute ethyl alcohol, obtain A type antibacterial debonding agents.
Embodiment 2
1）Intermediate product --- three（2- Dichloroethyls）The synthesis of amine hydrochlorate
Under the conditions of ice-water bath, 30ml absolute ethyl alcohol and 10ml are added into 250ml three-necked flask（0.075mol）Three
Monoethanolamine, turn on agitator, by 19ml（0.2625mol）Thionyl chloride be slowly dropped to tear drop bottle in reaction solution, have gas
Body is slowly emerged, and tail gas is absorbed with sodium hydroxide solution, after being added dropwise, is to slowly warm up to 35 DEG C, stirring reaction 2h, then
It is gradually heating to 65 DEG C, reacts 2.5h, continues to be heated to no gas to release, cooling, crystallization, then filtered, and with anhydrous
Ethanol washs repeatedly, 50 DEG C of drying, obtains white solid；
2）Final product --- three（2- hexadecyl dimethylammonio ethyls）Amine（Type B antibacterial debonding agent）Synthesis；
Under the conditions of ice-water bath, 1g is weighed（0.0042mol）Three（2- Dichloroethyls）Hydrogen-oxygen is added dropwise in three-necked flask in amine hydrochlorate
The pH value for changing sodium solution regulation system is 7；Agitator and heater switch are started, is warming up to 55 DEG C；Measure 5ml（0.014mol）'s
N-N dimethyl hexadecyl base tertiary amines are slowly dropped in the reaction solution of three-necked flask, after being added dropwise, continue to be heated to 85
DEG C, sustained response 7h；Cooling, crystallization, are then filtered, and repeatedly washed with anhydrous sodium sulfate, ethyl acetate and absolute ethyl alcohol
Wash, 50 DEG C of drying, obtain Type B antibacterial debonding agent.
Embodiment 3
1）Intermediate product --- three（2- Dichloroethyls）The synthesis of amine hydrochlorate
Under the conditions of ice-water bath, 20ml toluene and 10ml are added into 250ml three-necked flask（0.075mol）Three ethanol
Amine, turn on agitator, by 17ml（0.225mol）Thionyl chloride be slowly dropped to tear drop bottle in reaction solution, have gas slowly
Emerge, tail gas is absorbed with sodium hydroxide solution, after being added dropwise, is to slowly warm up to 33 DEG C, stirring reaction 2.5h, then gradually
70 DEG C are warming up to, reacts 2h, continues to be heated to no gas releasing, cooling separates out a large amount of white solids, then filtered, be used in combination
Absolute ethyl alcohol washs repeatedly, 50 DEG C of drying, obtains white solid；
2）Final product three（2- chlorination octadecyldimethyl ammonium ethyls）Amine（C-type antibacterial debonding agent）Synthesis
Under the conditions of ice-water bath, claim 1.5g（0.0062mol）Three（2- Dichloroethyls）Amine hydrochlorate and a certain amount of sodium hydroxide are molten
Liquid is added in three-necked flask, and the pH value of regulation system is 9；Agitator and heater switch are started, is warming up to 60 DEG C；Measure 8ml
（0.0186mol）N-N dimethyl stearyl tertiary amines be slowly dropped in the reaction solution of three-necked flask.After being added dropwise,
Continue to be heated to 90 DEG C, sustained response 6h；Cooling, crystallization, are then filtered, and with anhydrous sodium sulfate, ethyl acetate and nothing
Water-ethanol washs repeatedly, 50 DEG C of drying, obtains c-type antibacterial debonding agent.
Embodiment 4
A type antibacterial debonding agents are configured to the solution that concentration is 0.01g/ml, pipetted by dosage into standard fibers dissociation device, with
Paper pulp fiber is mixed, and 5000r is discongested under normal temperature；
Paper pulp fiber adds 0,0.532%, 0.798%, 1.06% A type antibacterial debonding agents during manufacturing paper with pulp, stirred after discongesting
Quantification of 660g/m is manufactured paper with pulp into after mixing uniformly2Flossy pulp-board, points of three sections squeezings under 4MPa, every section of squeezing changes dry hair after terminating
Blanket simultaneously replaces filter paper, and positive and negative squeezing, the squeezing time is 2min+2min+2min, and after squeezing terminates, wet web is put into 105 DEG C
Polisher on positive and negative dry same time, the moisture of flossy pulp-board for ensureing to manufacture paper with pulp to obtain is between 8% ~ 12%, by drying
Flossy pulp-board afterwards is placed on equilibrium water conten 12h in hermetic bag.The physical performance index testing result of the gained flossy pulp-board such as institute of table 1
Show：
Embodiment 5
Type B antibacterial debonding agent is configured to the solution that concentration is 0.01g/ml, pipetted by dosage into standard fibers dissociation device, with
Paper pulp fiber is mixed, and 5000r is discongested under normal temperature；
Paper pulp fiber adds 0,0.532%, 0.798%, 1.06% Type B antibacterial debonding agent during manufacturing paper with pulp, stirred after discongesting
Quantification of 660g/m is manufactured paper with pulp into after mixing uniformly2Flossy pulp-board, points of three sections squeezings under 4MPa, every section of squeezing changes dry hair after terminating
Blanket simultaneously replaces filter paper, and positive and negative squeezing, the squeezing time is 2min+2min+2min, and after squeezing terminates, wet web is put into 105 DEG C
Polisher on positive and negative dry same time, the moisture of flossy pulp-board for ensureing to manufacture paper with pulp to obtain is between 8%-12%, by drying
Flossy pulp-board afterwards is placed on equilibrium water conten 12h in hermetic bag.The physical performance index of gained flossy pulp-board is as shown in table 2：
Embodiment 6
C-type antibacterial debonding agent is configured to the solution that concentration is 0.01g/ml, pipetted by dosage into standard fibers dissociation device, with
Paper pulp fiber is mixed, and 5000r. is discongested under normal temperature
Paper pulp fiber adds 0,0.532%, 0.798%, 1.06% c-type antibacterial debonding agent during manufacturing paper with pulp, stirred after discongesting
Quantification of 660g/m is manufactured paper with pulp into after mixing uniformly2Flossy pulp-board, points of three sections squeezings under 4MPa, every section of squeezing changes dry hair after terminating
Blanket simultaneously replaces filter paper, and positive and negative squeezing, the squeezing time is 2min+2min+2min.After squeezing terminates, wet web is put into 105 DEG C
Polisher on positive and negative dry same time, the moisture of flossy pulp-board for ensureing to manufacture paper with pulp to obtain is between 8%-12%, by drying
Flossy pulp-board afterwards is placed on equilibrium water conten 12h in hermetic bag.The antibacterial and soft effect of gained antibacterial Time of Fluff Slurry are with antibacterial solution
The increase of key agent dosage and improve constantly.
Claims (9)
1. a kind of synthesis technique of antibacterial debonding agent, antibacterial debonding agent and purposes, it is characterised in that comprise the following steps：
First, under the conditions of ice-water bath, organic solvent and triethanolamine are added in three-necked flask, turn on agitator, chlorine is added dropwise
Change sulfoxide, 30 DEG C ~ 35 DEG C, stirring reaction 2h ~ 3h are warming up to after adding, be continuously heating to 60 DEG C ~ 70 DEG C, reaction 2h ~ 3h to nothing
Gas is released, and cooling, crystallization, is filtered and is repeatedly washed with chloroform or absolute ethyl alcohol, dries, obtain intermediate product three（The chloroethenes of 2- bis-
Base）Amine hydrochlorate；
Secondly, to above-mentioned intermediate product three（2- Dichloroethyls）It is molten that the sodium hydroxide that concentration is 5mol/L is added dropwise in amine hydrochlorate
Liquid, the pH value of regulation system then heat to 50 DEG C ~ 60 DEG C and start that long-chain alkyl tertiary amine is added dropwise, heated up after finishing between 6 ~ 9
Continue to react 6h ~ 8h to 80 DEG C ~ 90 DEG C, cooling, crystallization, filter and washed repeatedly with anhydrous sodium sulfate, ethyl acetate and ethanol,
Drying, obtains antibacterial debonding agent.
2. the synthesis technique of a kind of antibacterial debonding agent according to claim 1, it is characterised in that the triethanolamine, chlorine
Change sulfoxide mol ratio be：1:3.0~4.5.
3. the synthesis technique of a kind of antibacterial debonding agent according to claim 1, it is characterised in that the organic solvent is nothing
Water-ethanol, chloroform, toluene, isopropanol.
A kind of 4. synthesis technique of antibacterial debonding agent according to claim 1, it is characterised in that the long-chain alkyl tertiary amine
For N-N dimethyl-octas alkyl tertiary amine, N-N dimethyl hexadecyl bases tertiary amine, N-N dimethyl stearyl tertiary amines.
A kind of 5. synthesis technique of antibacterial debonding agent according to claim 1, it is characterised in that the intermediate product three
（2- Dichloroethyls）The mol ratio of amine hydrochlorate and long-chain alkyl tertiary amine is：1:3.0~4.5.
A kind of 6. synthesis technique of antibacterial debonding agent according to claim 1, it is characterised in that described antibacterial debonding agent
For the antibacterial debonding agent of tri-long-chain alkyl.
A kind of 7. synthesis technique of antibacterial debonding agent according to claim 1, it is characterised in that described antibacterial debonding agent
For with three N+The cationic surfactant of ion.
8. debonding agent prepared by a kind of synthesis technique of antibacterial debonding agent according to claim 1, it is characterised in that described
Antibacterial debonding agent general structure is as follows：
Wherein, n 7,15,17；
Specific reflection equation is as follows：
1）The synthesis of intermediate product：
2）Quaternization reacts：
Wherein, n 7,15,17.
9. the purposes of a kind of antibacterial debonding agent according to claim 1, it is characterised in that the antibacterial debonding agent is applied to
Fluff pulp fibers, it can also be applied to the production of antimicrobial form paper for daily use and high life paper.
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| CN111001031A (en) * | 2019-12-30 | 2020-04-14 | 福建恒安集团有限公司 | Preparation method of adult paper diaper |
| CN111001031B (en) * | 2019-12-30 | 2022-03-25 | 福建恒安集团有限公司 | Preparation method of adult paper diaper |
| CN113289047A (en) * | 2021-06-24 | 2021-08-24 | 礼顿卫生用品(佛山)有限公司 | Paper diaper capable of effectively resisting bacteria and deodorizing |
| CN113289047B (en) * | 2021-06-24 | 2022-01-25 | 礼顿卫生用品(佛山)有限公司 | Paper diaper capable of effectively resisting bacteria and deodorizing |
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