CN105567119B - A kind of chitosan system adhesive and its preparation method and application - Google Patents
A kind of chitosan system adhesive and its preparation method and application Download PDFInfo
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- CN105567119B CN105567119B CN201610118927.4A CN201610118927A CN105567119B CN 105567119 B CN105567119 B CN 105567119B CN 201610118927 A CN201610118927 A CN 201610118927A CN 105567119 B CN105567119 B CN 105567119B
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J105/00—Adhesives based on polysaccharides or on their derivatives, not provided for in groups C09J101/00 or C09J103/00
- C09J105/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention relates to a kind of chitosan system adhesive, preparation method and applications, its structural formula such as formula(1)It is shown:
Description
Technical field
The invention belongs to adhesive field, and in particular to a kind of chitosan system adhesive and its preparation method and application.
Background technology
Adhesive is also known as adhesive, is that one kind can be combined closely material of the same race or dissimilar substances by surface
Into entirety, stress conduction can be played, and disclosure satisfy that the connection medium of certain physical and chemical properties requirement.
In spinning coating industry, adhesive is also referred to as crosslinking agent, is mainly used in coating process.Top finish is in fabric
Surface uniformly coating or bonding one floor height molecular material, make it have different functions.Adhesive will influence in coating
The tightness degree combined to macromolecular functional layer with fabric, so as to influence the performance of the efficiency of macromolecular functional layer and water-wash resistance
Can, the pliability and gas permeability of fabric are also influenced whether, the comfort level that textile is worn further is influenceed, so the property of binder
Can be very big to the performance impact of spinning coating product.
Spinning coating technique just turns into the high pollution high energy consumption technique being gradually eliminated at present, is the bonding because used
Agent is mostly smell pungent, toxic property, does not allow degradable high-molecular compound, can become fabric after fabric face coating
Firmly, gas permeability is lost, reduces the comfort level of textile dress, environment-friendly type aqueous binder turns into the problem that producer is competitively studied.
But existing water-based binder washing fastness is very low, after washing, coating easily comes off product, and have impact on water-based
The application of binder.Therefore the adhesive that a kind of stickiness is strong, environment friendly and pollution-free is developed, turns into and improve spinning coating technique urgently
Problem to be solved.
The content of the invention
A kind of chitosan system adhesive is provided the invention aims to overcome the deficiencies in the prior art.
To reach above-mentioned purpose, the technical solution adopted by the present invention is:A kind of chitosan system adhesive, its structural formula is such as
Shown in formula (1):
Its number-average molecular weight is 20000~30000.
Preferably, the number-average molecular weight of chitosan system adhesive is 24000~30000.More preferably 28000~30000.
A further object of the present invention is to provide a kind of preparation method of above-mentioned chitosan system adhesive, and it includes following step
Suddenly:
(a) 3- isocyanides acid propylene, indicator are dissolved in the first organic solvent, are placed in cryostat, be passed through N2With HBr gas
Body, react to obtain 3- bromopropyl isocyanates;
(b) chitosan, sodium hydroxide are added in the second organic solvent and are configured to solution, under heating, stirring condition
Add 3- bromopropyl isocyanates to be reacted, then adjust pH value to neutrality and precipitated, slightly yellow powder is washed to obtain after filtering
End.
Further, the indicator is two Chinese cassia tree acetone, and first organic solvent is dichloromethane or chloroform or two
The combination of person.
Further, in step (a), 3- isocyanides acid propylene, indicator are dissolved in the first organic solvent, at 0~5 DEG C
Under conditions of be passed through N2With HBr gases, reaction solution is set to stop reaction by faint yellow change laking, again with toluene extracts to obtain 3- bromines
Propylisocyanate.
Further, in step (a), the 3- isocyanides acid propylene, indicator, the mass ratio of the first organic solvent are 1:8
×10-5~1.2 × 10-4:7~10, N2Volume ratio with HBr is 1:0.9~1.2.
Preferably, in step (b), second organic solvent is one kind or more in methanol, ethanol and isopropanol
The combination of kind.
Preferably, the chitosan, sodium hydroxide, the second organic solvent, the mass ratio of 3- bromopropyl isocyanates are 1:
18~22:12~16:3~6.
Further, in step (b), chitosan, sodium hydroxide is added in the second organic solvent and are configured to solution, is added
Heat adds 3- bromopropyl isocyanates to 40~60 DEG C after stirring 20~60min, and regulation pH value to neutrality is entered after reacting 2~3h
Row precipitation, filtering, is washed with methanol, obtains micro-yellow powder.
It is still another object of the present invention to provide a kind of application of above-mentioned chitosan system adhesive in fabric foam coating.
Because above-mentioned technical proposal is used, the present invention has following advantages compared with prior art:Chitosan system of the present invention
Adhesive, there is specific chemical structural formula, its have it is degradable, have no irritating odor, the water soluble nature of nonhazardous, solve
Determined spinning coating industry high pollution the problem of, by the crosslinked action of its own, solve terylene and polyamide fibre itself do not lived
Property group, unstable problem is combined with binder, so as to solve the defects of coating is not water-fastness;And chitosan is gathered
Excellent filming performance, hygroscopicity, gas permeability, can be such that the thickness of film in coating procedure is accurately controlled within 100nm, make into
Gas permeability, the pliability of product fabric are greatly enhanced than common coating, and will not increase the weight of fabric.
Embodiment
Chitosan system of the present invention adhesive, shown in its structural formula such as formula (1):
Its number-average molecular weight is 20000~30000.The chitosan system adhesive have it is degradable, have no irritating odor,
The water soluble nature of nonhazardous, solve the problems, such as spinning coating industry high pollution, by the crosslinked action of its own, solve
Terylene and polyamide fibre itself do not have active group, and unstable problem is combined with binder, so as to solve coating not water-fastness
The defects of;And gathered the excellent filming performance of chitosan, hygroscopicity, gas permeability, the thickness of film in coating procedure can be made
It is accurately controlled within 100nm, the gas permeability of finished textile product, pliability is greatly enhanced than common coating, and
The weight of fabric will not be increased.Its number-average molecular weight is preferably 24000~30000, and more preferably 28000~30000.Now
Adhesive molecular weight it is moderate, be advantageous to be sufficiently mixed with other chemical substances, so as to improve filming performance.
The preparation method of above-mentioned chitosan system adhesive, it comprises the following steps:(a) by 3- isocyanides acid propylene, indicator
It is dissolved in the first organic solvent, is placed in cryostat, is passed through N2With HBr gases, 3- bromopropyl isocyanates is reacted to obtain;(b) by shell
Glycan, sodium hydroxide are added in the second organic solvent and are configured to solution, and 3- bromopropyl isocyanides are added under heating, stirring condition
Acid esters is reacted, and is then adjusted pH value to neutrality and is precipitated, micro-yellow powder is washed to obtain after filtering.It is prepared by this method
Step is simple, and obtained chitosan system adhesive purity is higher, thus filming performance is good.
In step (b), the mass ratio of chitosan and 3- the bromopropyl isocyanates is preferably 1:3~6;The indicator
To be preferably two Chinese cassia tree acetone, first organic solvent is preferably dichloromethane or chloroform, and second organic solvent is preferred
For methanol, ethanol or isopropanol.
Step (a) is specially:By 3- isocyanides acid propylene, two Chinese cassia tree acetone solutions in dichloromethane, in 0~5 DEG C of bar
N is passed through under part2With HBr gases, reaction solution is set to stop reaction by faint yellow change laking, again with toluene extracts to obtain 3- bromopropyls
Isocyanates;The 3- isocyanides acid propylene, two Chinese cassia tree acetone, CH2Cl2Mass ratio be 1:8×10-5~1.2 × 10-4:7~
10, N2Volume ratio with HBr is 1:0.9~1.2;So as to improve the purity and yield of 3- bromopropyl isocyanates.Step
(b) it is specially:Chitosan, sodium hydroxide are added in isopropanol and are configured to solution, is heated to 40~60 DEG C, stirring 20~
3- bromopropyl isocyanates is added after 60min, regulation pH value to neutrality is precipitated after reacting 2~3h, is filtered, is washed with methanol
Wash, obtain micro-yellow powder;In step (b), chitosan, sodium hydroxide, isopropanol, the mass ratio of 3- bromopropyl isocyanates
For 1:18~22:12~16:3~6.The chitosan is using existing, as Nantong Lv Shen bioengineering Co., Ltd gives birth to
The relative molecular mass of production is 30000, deacetylation > 90% water soluble chitosan.
Application of the above-mentioned chitosan system adhesive in fabric foam coating, the chitosan system adhesive can be coated individually
Fabric surface, form the fabric of ventilative water repellent, can also be by other chemical materials, such as activated carbon, aeroge, nanogold
Belong to the bonding such as powder, microencapsulation material on the surface of fabric, formation has adsorption cleaning tender, temperature control, radiation proof function altogether
Functional fabric;Either it is mixed according to a certain percentage with agent for three purposes, thickener, foaming agent, foam stabiliser, water,
It is stirring evenly and then adding into foam coating machine to be coated on fabric, suitable for a variety of fabrics such as terylene, polyamide fibre, cotton, blending.Thickening
Agent is from sodium alginate conventional, that 30 mesh, viscosity such as the global marine alga auxiliary agent Co., Ltd in Lianyun Harbour are 500mPa.s;
Foaming agent is from routine, such as the 6501-1 type auxiliary agents of Jinan Guang Quan Chemical Co., Ltd.s;Foam stabiliser is from conventional
, such as the 6501-2 type auxiliary agents of Jinan Guang Quan Chemical Co., Ltd.s;Thickener is beautified from routine, such as Guangdong Guangdong
The YM-2060 of work Co., Ltd;Agent for three purposes is from routine, such as He Te groups model HS1100 water and oil repellent finish
Agent.
The preferred embodiment of the invention is described in detail below in conjunction with accompanying drawing:
Embodiment 1
The present embodiment provides a kind of preparation method of chitosan system adhesive, and it comprises the following steps:
(a) by 3- isocyanides acid propylene and two Chinese cassia tree acetone (CAS 622-21-9, or 1,9- connection biphenyl -1,3,6,8- nonyls
Tetraene -5- ketone, chemical formula are) it is dissolved in CH2Cl2In, then solution is placed in cold
In bath, regulation cryostat temperature is 0 DEG C, is passed through N2With HBr gases, question response liquid is stopped reaction, added by faint yellow change laking
Enter toluene extraction product, it is standby to obtain product 3- bromopropyl isocyanates;Wherein, 3- isocyanides acid propylene, two Chinese cassia tree acetone, CH2Cl2
Mass ratio be 1:0.0001:8, N2Volume ratio with HBr is 1:1,3- isocyanide acid propylene and HBr mol ratio are 1:3;
(b) chitosan and sodium hydroxide are added in isopropanol, solution is made, be heated to 40 DEG C, after stirring 30min,
3- bromopropyl isocyanates is added, after reacting 2h, regulation pH value is 7, is filtered after precipitation, is washed with methanol, obtain micro-yellow powder,
As (number-average molecular weight is 20000~22000 to propylisocyanate chitosan adhesive, and structural formula is);Its
Middle chitosan, sodium hydroxide, isopropanol, the mass ratio of 3- bromopropyl isocyanates are 1:20:15:5 ratio.
It is in mass ratio by agent for three purposes, obtained chitosan system adhesive, thickener, foaming agent, foam stabiliser and water
3:2:1:2:2:90 mix, and the coating agent to stir is standby;By coating agent and sample cloth (1.6 meters of door, 20D, 380T
Nylon Taffeta fabric, mass area ratio 36.3g/m2) foam coating machine is added, it is coated according to 1.0m/s speed,
Then sample is obtained after being dried at a temperature of 180 DEG C;Shown in test result table 1.The test of sample surfaces water repellency is according to national standard
GB/T 4745-2012《The detection and evaluation of textile water proof performance get wet method》Tested;Sample penetrability is according to national standard
GB/T 12704.1-2009《Textile fabric penetrability experimental method Part I:Moisture absorption method》Tested, test condition
HDF37.5℃;Sample gas permeability is according to national standard GB/T 5453-1997《The test of textile fabric gas permeability》Tested, surveyed
Strip part 20cm2, 100pa;Sample washing methods is according to GB/T 8629-2001《Textile Test home washings and dry journey
Sequence》Carry out, washing procedure 5A, 40 DEG C of wash temperature, add " ECE " synthetic detergent, tumble drying.
Table 1 coats the sample cloth performance test data of chitosan system adhesive in embodiment 1
Embodiment 2
The present embodiment provides a kind of preparation method of chitosan system adhesive, its preparation process with it is basic in embodiment 1
Unanimously, unlike, its response parameter is inconsistent, is specially:In step (a), 3- isocyanides acid propylene, two Chinese cassia tree acetone, CH2Cl2
Mass ratio be 1:0.00008:7, N2Volume ratio with HBr is 1:0.9, chitosan, sodium hydroxide, isopropanol, 3- bromopropyls
The mass ratio of isocyanates is 1:18:12:3, the number-average molecular weight of the propylisocyanate chitosan adhesive finally given is
24000~26000, test result is as shown in table 2.
Table 2 coats the sample cloth performance test data of chitosan system adhesive in embodiment 2
Embodiment 3
The present embodiment provides a kind of preparation method of chitosan system adhesive, its preparation process with it is basic in embodiment 1
Unanimously, unlike, its response parameter is inconsistent, is specially:In step (a), 3- isocyanides acid propylene, two Chinese cassia tree acetone, CH2Cl2
Mass ratio be 1:0.00012:10, N2Volume ratio with HBr is 1:1.2, chitosan, sodium hydroxide, isopropanol, 3- bromopropyls
The mass ratio of isocyanates is 1:22:16:2, the number-average molecular weight of the propylisocyanate chitosan adhesive finally given is
28000~30000, test result is as shown in table 3.
Table 3 coats the sample cloth performance test data of chitosan system adhesive in embodiment 3
Comparative example 1
This example provides a kind of application of existing adhesive, is specially:By agent for three purposes, adhesive for polyurethane, (Shanghai, which thinks to contain, gathers
The auxiliary agent of the U-57 types of compound Materials Co., Ltd), thickener, foaming agent, foam stabiliser and water, in mass ratio 3:2:1:2:
2:90 ratio is mixed, and coating agent is obtained after stirring, and coating agent and sample cloth are added into foam coating machine, according to
1.0m/s speed is coated, and obtains sample after then being dried at a temperature of 180 DEG C, test result is as shown in table 3.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar can understand present disclosure and implement according to this, and it is not intended to limit the scope of the present invention, all according to the present invention
The equivalent change or modification that Spirit Essence is made, it should all be included within the scope of the present invention.
Claims (10)
1. a kind of chitosan system adhesive, it is characterised in that shown in its structural formula such as formula (1):
Its number-average molecular weight is 20000~30000.
2. chitosan system according to claim 1 adhesive, it is characterised in that:Its number-average molecular weight be 24000~
30000。
3. the preparation method of the chitosan system adhesive of claim 1 or 2, it is characterised in that it comprises the following steps:
(a) 3- isocyanides acid propylene, indicator are dissolved in the first organic solvent, are placed in cryostat, be passed through N2With HBr gases, reaction
Obtain 3- bromopropyl isocyanates;
(b) chitosan, sodium hydroxide are added in the second organic solvent and are configured to solution, added under heating, stirring condition
3- bromopropyl isocyanates is reacted, then adjust pH value to neutrality precipitated, washed after filtering micro-yellow powder i.e.
Can.
4. the preparation method of chitosan system adhesive according to claim 3, it is characterised in that:The indicator is two Chinese cassia trees
Acetone, first organic solvent are dichloromethane or chloroform or combination.
5. the preparation method of chitosan system adhesive according to claim 3, it is characterised in that:In step (a), by 3- isocyanides
Acid propylene, indicator are dissolved in the first organic solvent, and N is passed through under conditions of 0~5 DEG C2With HBr gases, make reaction solution by
Faint yellow change laking stops reaction, and again with toluene extracts to obtain 3- bromopropyl isocyanates.
6. the preparation method of chitosan system adhesive according to claim 4, it is characterised in that:In step (a), the 3- is different
Cyanic acid propylene, two Chinese cassia tree acetone, the mass ratio of the first organic solvent are 1:8×10-5~1.2 × 10-4:7~10, N2With HBr's
Volume ratio is 1:0.9~1.2.
7. the preparation method of chitosan system adhesive according to claim 3, it is characterised in that:In step (b), described second
Organic solvent is one or more combinations in methanol, ethanol and isopropanol.
8. the preparation method of chitosan system adhesive according to claim 3, it is characterised in that:In step (b), the shell gathers
Sugar, sodium hydroxide, the second organic solvent, the mass ratio of 3- bromopropyl isocyanates are 1:18~22:12~16:3~6.
9. according to the preparation method of the chitosan system adhesive of claim 3 or 7 or 8, it is characterised in that:, will in step (b)
Chitosan, sodium hydroxide are added in the second organic solvent and are configured to solution, are heated to 40~60 DEG C, after stirring 20~60min
3- bromopropyl isocyanates is added, regulation pH value to neutrality is precipitated after reacting 2~3h, is filtered, is washed with methanol, obtain micro- Huang
Color powder.
10. application of the chitosan system adhesive in fabric foam coating described in claim 1 or 2.
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CN112358554B (en) * | 2020-10-30 | 2022-09-09 | 苏州棠华纳米科技有限公司 | Cross-linking agent for water-repellent and oil-repellent finishing, and preparation method and application thereof |
CN115703751B (en) * | 2021-08-16 | 2024-05-07 | 广西至善新材料科技有限公司 | Preparation method of glycidyl gallate and adhesive thereof |
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CN101870743A (en) * | 2010-07-16 | 2010-10-27 | 北京化工大学常州先进材料研究院 | Preparation and application of natural polymer binder capable of realizing photopolymerization |
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