CN109467697A - A kind of branched polyamide-glyoxal resin adhesive and preparation method and application - Google Patents
A kind of branched polyamide-glyoxal resin adhesive and preparation method and application Download PDFInfo
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- CN109467697A CN109467697A CN201811307822.9A CN201811307822A CN109467697A CN 109467697 A CN109467697 A CN 109467697A CN 201811307822 A CN201811307822 A CN 201811307822A CN 109467697 A CN109467697 A CN 109467697A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
- C08G69/50—Polymers modified by chemical after-treatment with aldehydes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
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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
- C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
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Abstract
The invention discloses a kind of branched polyamide-glyoxal resin adhesive, the branched polyamide-glyoxal resin adhesive as three (2- amino-ethyl) amine and urea it is solvent-free, be made without branched polyamide made from deamination condensation reaction under catalysts conditions and glyoxal addition, condensation reaction, and the branched polyamide-glyoxal resin adhesive is claret uniform liquid, solid content 55-60%, pH 7.0-8.0, Storage period 60 days or more.It has the characteristics that formaldehydeless release, storage stability is good, has excellent performance, and realizes being substantially improved for adhesive overall performance.The present invention also provides the preparation methods of the adhesive.
Description
Technical field
The present invention relates to timber to process technical field, especially a kind of branched polyamide-glyoxal resin adhesive
And preparation method and application.
Background technique
Lauxite (UF), phenolic resin (PF) and melamine resin (MF) are extensive in current Wood-based Panel Production
The conventional resins adhesive used.These three resins are all anti-through addition and polycondensation with urea, phenol and melamine by formaldehyde
It should be made.Since formaldehyde is main synthesis material, more or less all remains the formaldehyde for having neither part nor lot in reaction in final resin, that is, swim
From formaldehyde；In addition, especially molecular resin can be sent out under the condition of high temperature and high humidity since addition and polycondensation reaction are reversible reaction
Raw depolymerization.The two reasons can all lead to wood-based panel product gradually release formaldehyde in use, cause to human body and environment
Harm.With the enhancing of social progress and environmental consciousness, Form aldehyde release problem is increasingly highlighted, and the application of diaion is faced with
Unprecedented challenge.
In above-mentioned three kinds of resins, Lauxite have it is low in cost, have excellent performance, be easy to large-scale industrial production and make
Significant advantage, therefore it is widely used in the generation of particieboard, glued board and middle density county fiberboard.But Lauxite there is also
Laminated product durability difference and the biggish defect of burst size of methanal.It is general in order to reduce the Form aldehyde release of Lauxite laminated product
All over low mole prop0rtion synthetic technology is used, in wood shavings board manufacturing process, the molar ratio of urea and formaldehyde has been approached 1:1.Low mole
Form aldehyde release is although significantly reduced than Lauxite, but also leads to the overall performance sharp fall of plate.Simultaneously as urea
There are the unstable groups such as methylene ether link or methylol in urea formaldehyde structure, and Lauxite laminated product is at it using in the period
The constant release formaldehyde of meeting constitutes long-term potential threat to environmental and human health impacts.Zero formaldehyde or ultra-low formaldehyde are discharged
Pursuit promote countries in the world academia and industry actively find it is low in cost, have excellent performance, the novel nothing of simple production process
Formaldehyde resin.
Isocyanates gluing agent (pMDI) is currently the most important non-formaldehyde series Artificial Plate Adhesive, real both at home and abroad
Existing industrialized production and application, the oriented wood chipboard of North America 20% or so use the agent of isocyanates gluing, and China, which also has, quite to be counted
The production line of amount uses, but its cost is ten times of UF resin or so, simultaneously because use process need to use release agent etc., application
Technique is relative complex, and existing market share is still extremely limited.It is the biomass wood of representative with tannin, soybean protein, lignin etc.
Material adhesive has also realized industrialized production and application, but is limited by the various originals such as raw material total amount, cost and technique for applying complexity
Cause, it is difficult to meet wood-based panel industry heavy industrialization use demand.
Using urea as primary raw material, the solution route that formaldehyde substitute is possible cost of implementation and performance balance is found.Its
In, the concern of a part of domestic and foreign scholars has been caused with the research that glyoxal substitution formaldehyde prepares based Wood Adhesives.Document
“Performance and reaction mechanism of zero formaldehyde-emission urea-
Glyoxal (UG) resin " reports a kind of composition principle of urea-glyoxal based Wood Adhesives；" one kind is formaldehydeless to be released patent
Resin adhesive put and the preparation method and application thereof (ZL201310274163.4) " discloses a kind of formaldehydeless release resin glue
The preparation method of glutinous agent, this Resin adhesive is directly synthetically prepared using urea and glyoxal as synthesis material step by step, and is had
Standby certain glue performance.But the reaction of urea and glyoxal under acid or alkaline conditions is easy to generate dihydroxy ethylene
Urea cyclic structure and cause functional group to be consumed, polymer molecular weight is small, and the degree of branching is lower.Meanwhile polycondensation reaction can generate half
Acetal and linear diether linkage structure, cause resin body structural stability poor.Therefore, the tree directly synthesized with urea and glyoxal
Rouge bonding strength is not ideal enough, and the water resistance of especially wood-based plate is poor.
Summary of the invention
In view of the above-mentioned problems, the purpose of the present invention is to provide a kind of branched polyamide-glyoxal resin adhesive,
It has the characteristics that formaldehydeless release, storage stability is good, has excellent performance, and realizes being substantially improved for adhesive overall performance,
The technical solution adopted by the invention is as follows:
A kind of branched polyamide-glyoxal resin adhesive, the branched polyamide-glyoxal resin adhesive is by three
(2- amino-ethyl) amine and urea it is solvent-free, without branched polyamide made from deamination condensation reaction under catalysts conditions and second two
Aldehyde addition, condensation reaction are made, and the branched polyamide-glyoxal resin adhesive is claret uniform liquid, solid content
For 55-60%, pH 7.0-8.0, Storage period 60 days or more.
Further, the branched polyamide molecule branch has-CH2-CH2- NHCONH- repetitive structure and branch last-in-chain(LIC)
End is-CH2-CH2-NH-CO-NH2Structure.
The present invention also provides foregoing branched polyamide-glyoxal resin adhesive preparation methods, include the following steps:
A. the reaction incipient stage will measure as T1Three (2- amino-ethyl) amine be warming up to 40-60 DEG C in oil bath, stirring
Lower addition metering is U1Urea, the molar ratio U of urea and three (2- amino-ethyl) amine1/T1Control is between 3.5-5.0；Continue
It is warming up to 110-120 DEG C, insulation reaction is absorbed in reaction process with ammonia absorption device and overflows ammonia；
B. it is T that second of metering is added after insulation reaction 2.0-3.0 hours at 110-120 DEG C2Three (2- amino-ethyls)
Amine makes U1/(T1+T2) molar ratio is 0.7-1.0, second of urea, metered amount U is added in insulation reaction after 3.0-4.0 hours2,
Make (U1+U2)/(T1+T2) molar ratio be 2.0-2.6, keep the temperature 1.5-2.0 hour, discharging, cool down；
C. product after cooling is three (2- amino-ethyl) amine-urea polyamide solid, in 50-60 DEG C of item in drying box
Deamination 3-4 hours under part, for use；
D. 40% (mass fraction w%) glyoxal solution pH value for measuring as G is adjusted to 8.0-9.0 at room temperature,
40 DEG C or so are heated in water-bath, ureometer used in lower three (2- amino-ethyl) amine-urea polyamide by synthesis of stirring
Three (2- amino-ethyl) amine-urea polyamide solid that metering is added is calculated, glyoxal/urea mol ratio 0.8-1.2 is made；Continue
60 DEG C are warming up to, adjusting pH again after three (2- amino-ethyl) amine-urea polyamide solid all dissolution is 8.0-9.0, is protected
Temperature reaction 1.0-1.5 hours, it is 7.0-8.0 that pH is adjusted after natural cooling, obtains branched polyamide-glyoxal resin adhesive.
Application of the branched polyamide-glyoxal resin adhesive in wood-based panel industry production.
Compared with prior art, the invention has the following advantages:
The invention firstly uses the deamination condensation reaction of three (2- amino-ethyl) amine and urea preparations to have branched structure
Polyamide macromolecule is further reacted using its stability height, good water solubility, the feature for having urea reaction activity with glyoxal
Polyamide-glyoxal resin adhesive is prepared, stable, performance is stored in the formaldehydeless release of synthesized polyamide-glyoxal resin
It is excellent, it can use in humid conditions, realize being substantially improved for adhesive overall performance.
Specific embodiment
To keep the purposes, technical schemes and advantages of the application apparent, the present invention is made into one below with reference to embodiment
Step explanation, embodiments of the present invention include but is not limited to the following example.Based on the embodiment in the application, this field is common
Technical staff's every other embodiment obtained without making creative work belongs to the application protection
Range.
A kind of branched polyamide-glyoxal resin adhesive is urged by three (2- amino-ethyl) amine and urea in solvent-free, nothing
Branched polyamide made from deamination condensation reaction is further made with glyoxal addition, condensation reaction under the conditions of agent, and described
Branched polyamide-glyoxal resin adhesive is claret uniform liquid, solid content 55-60%, pH 7.0-8.0, storage
Phase 60 days or more.Wherein, the branched polyamide molecule branch has-CH2-CH2- NHCONH- repetitive structure and last-in-chain(LIC)
End is-CH2-CH2-NH-CO-NH2Structure.Branched polyamide-glyoxal resin adhesive applications are in wood-based panel industry production.
Branched polyamide above-mentioned-glyoxal resin adhesive preparation method, includes the following steps:
A. the reaction incipient stage will measure as T1Three (2- amino-ethyl) amine be warming up to 40-60 DEG C in oil bath, stirring
Lower addition metering is U1Urea, the molar ratio U of urea and three (2- amino-ethyl) amine1/T1Control is between 3.5-5.0；Continue
It is warming up to 110-120 DEG C, insulation reaction is absorbed in reaction process with ammonia absorption device and overflows ammonia；
B. it is T that second of metering is added after insulation reaction 2.0-3.0 hours at 110-120 DEG C2Three (2- amino-ethyls)
Amine makes U1/(T1+T2) molar ratio is 0.7-1.0, second of urea, metered amount U is added in insulation reaction after 3.0-4.0 hours2,
Make (U1+U2)/(T1+T2) molar ratio be 2.0-2.6, keep the temperature 1.5-2.0 hour, discharging, cool down；
C. product after cooling is three (2- amino-ethyl) amine-urea polyamide solid, in 50-60 DEG C of item in drying box
Deamination 3-4 hours under part, for use；
D. 40% (mass fraction) the glyoxal solution pH value for measuring as G is adjusted to 8.0-9.0 at room temperature, in water-bath
In be heated to 40 DEG C or so, urea used in lower three (2- amino-ethyl) amine-urea polyamide by synthesis of stirring calculate plus
Three (2- amino-ethyl) amine-urea polyamide solid for entering metering, makes glyoxal/urea mol ratio 0.8-1.2；Persistently overheating
To 60 DEG C, adjusting pH again after three (2- amino-ethyl) amine-urea polyamide solid all dissolution is 8.0-9.0, and heat preservation is anti-
It answers 1.0-1.5 hours, it is 7.0-8.0 that pH is adjusted after natural cooling, obtains branched polyamide-glyoxal resin adhesive.
Formaldehyde is not used in aforementioned adhesive preparation process, therefore formaldehydeless release, the adhesive of preparation are put at room temperature
Appearance (color, viscosity) does not have significant change after setting 60 days, and storage stability is high.
Different according to the hot pressing temperature of glued board pressing process, the water resistance of the glued board is different: (1) hot pressing temperature
It is 160~180 DEG C, when hot pressing time is 5 minutes, by national standard GB/T 17657-2013 " wood-based plate and face artificial board physics and chemistry
Can test method " test, when test specimen impregnates 24 in not less than 17 DEG C of cold water after wet shape bonding strength be 0.7Mpa or more, i.e.,
It can reach water resistance requirement of the national standard GB/T 98684-2015 " normal plywood " to III class glued board；(2) hot pressing temperature is
190~220 DEG C, hot pressing time be 5 minutes when, test specimen is impregnated 3 hours in 63 DEG C of hot water after bonding strength for 0.7Mpa with
On, that is, it can reach water resistance requirement of the national standard GB/T 98684-2015 " normal plywood " to II class glued board.
Equipment used by preparation method of the invention is conventional equipment, and preparation embodiment is as follows:
Embodiment 1:
Using three (2- amino-ethyl) amine, urea and glyoxals as Material synthesis, in which:
A. the reaction incipient stage will measure as T1Three (2- amino-ethyl) amine be warming up to 40-60 DEG C in oil bath, stirring
Lower addition metering is U1Urea, the molar ratio U of urea and three (2- amino-ethyl) amine1/T1Control is 3.5 or so；Persistently overheating
To 110 DEG C, insulation reaction is absorbed in reaction process with ammonia absorption device and overflows ammonia；
B. it is T that second of metering is added after insulation reaction 3.0 hours at 110 DEG C2Three (2- amino-ethyl) amine, make U1/
(T1+T2) molar ratio be 0.70, second of urea is added in insulation reaction after 3.0-4.0 hours, measure as U2, make (U1+U2)/(T1+
T2) molar ratio be 2.0, keep the temperature 1.5-2.0 hour, discharging, cool down；
C. product after cooling is three (2- amino-ethyl) amine-urea polyamide solid, in 50-60 DEG C of item in drying box
Deamination 3-4 hours under part, for use；
D. 40% (mass fraction w%) glyoxal solution pH value for measuring as G is adjusted to 8.0-9.0 at room temperature,
40 DEG C or so are heated in water-bath, stirring is lower to be calculated by urea used in three (2- amino-ethyl) amine-urea polyamide of synthesis
Three (2- amino-ethyl) amine-urea polyamide solid of metering is added, makes glyoxal/urea mol ratio 0.8；Persistently overheating is extremely
60 DEG C, adjusting pH again after three (2- amino-ethyl) amine-urea polyamide solid all dissolution is 8.0-9.0, insulation reaction
1.0-1.5 hours, it was 7.0-8.0 that pH is adjusted after natural cooling, obtained final branched polyamide-glyoxal resin adhesive.
Embodiment 2:
Using three (2- amino-ethyl) amine, urea and glyoxals as Material synthesis, in which:
A. the reaction incipient stage will measure as T1Three (2- amino-ethyl) amine be warming up to 40-60 DEG C in oil bath, stirring
Lower addition metering is U1Urea, the molar ratio U of urea and three (2- amino-ethyl) amine1/T1Control is 4.0 or so；Persistently overheating
To 115 DEG C, insulation reaction is absorbed in reaction process with ammonia absorption device and overflows ammonia；
B. it is T that second of metering is added after insulation reaction 2.5 hours at 115 DEG C2Three (2- amino-ethyl) amine, make U1/
(T1+T2) molar ratio be 0.85, second of urea (U is added in insulation reaction after 3.0-4.0 hours2), make (U1+U2)/(T1+T2) rub
You keep the temperature 1.5-2.0 hours, discharging is cooling than being 2.3；
C. product after cooling is three (2- amino-ethyl) amine-urea polyamide solid, in 50-60 DEG C of item in drying box
Deamination 3-4 hours under part, for use；
D. 40% (mass fraction w%) glyoxal solution pH value for measuring as G is adjusted to 8.0-9.0 at room temperature,
40 DEG C or so are heated in water-bath, stirring is lower to be calculated by urea used in three (2- amino-ethyl) amine-urea polyamide of synthesis
Three (2- amino-ethyl) amine-urea polyamide solid of metering is added, makes glyoxal/urea mol ratio 1.0；Persistently overheating is extremely
60 DEG C, adjusting pH again after three (2- amino-ethyl) amine-urea polyamide solid all dissolution is 8.0-9.0, insulation reaction
1.0-1.5 hours, it was 7.0-8.0 that pH is adjusted after natural cooling, obtained final branched polyamide-glyoxal resin adhesive.
Embodiment 3:
Using three (2- amino-ethyl) amine, urea and glyoxals as Material synthesis, in which:
A. the reaction incipient stage will measure as T1Three (2- amino-ethyl) amine be warming up to 40-60 DEG C in oil bath, stirring
Lower addition metering is U1Urea, the molar ratio U of urea and three (2- amino-ethyl) amine1/T1Control is 5.0 or so；Persistently overheating
To 120 DEG C, insulation reaction is absorbed in reaction process with ammonia absorption device and overflows ammonia；
B. it is T that second of metering is added after insulation reaction 2.0 hours at 120 DEG C2Three (2- amino-ethyl) amine, make U1/
(T1+T2) molar ratio be 1.0, second of urea (U is added in insulation reaction after 3.0-4.0 hours2), make (U1+U2)/(T1+T2) rub
You keep the temperature 1.5-2.0 hours, discharging is cooling than being 2.6；
C. product after cooling is three (2- amino-ethyl) amine-urea polyamide solid, in 50-60 DEG C of item in drying box
Deamination 3-4 hours under part, for use；
D. 40% (mass fraction w%) glyoxal solution pH value for measuring as G is adjusted to 8.0-9.0 at room temperature,
40 DEG C or so are heated in water-bath, stirring is lower to be calculated by urea used in three (2- amino-ethyl) amine-urea polyamide of synthesis
Three (2- amino-ethyl) amine-urea polyamide solid of metering is added, makes glyoxal/urea mol ratio 1.2；Persistently overheating is extremely
60 DEG C, adjusting pH again after three (2- amino-ethyl) amine-urea polyamide solid all dissolution is 8.0-9.0, insulation reaction
1.0-1.5 hours, it was 7.0-8.0 that pH is adjusted after natural cooling, obtained final branched polyamide-glyoxal resin adhesive.
Adhesive prepared by Example 1~3 respectively suppresses three layers of glued board with a thickness of the board using poplar board of 2mm, according to
National standard GB/T 17657-2013 " test methods of evaluating the properties of wood-based panels and surface decorated wood-based panels " carry out plate physical and mechanical property into
Row test, it is main to test plate water resistance.Concrete outcome is as follows:
Hot pressing temperature be 160~180 DEG C, hot pressing time be 5 minutes when, when test specimen impregnates 24 in 20 DEG C of cold water after it is wet
Shape bonding strength is 0.7~0.85Mpa；Hot pressing temperature is 190~220 DEG C, and when hot pressing time is 5 minutes, test specimen is in 63 DEG C of warm
Bonding strength after impregnating 3 hours in water is 0.7~0.95Mpa.
Above-described embodiment is merely a preferred embodiment of the present invention, and it is not intended to limit the protection scope of the present invention, as long as using
Design principle of the invention, and the non-creative variation worked and made is carried out on this basis, it should belong to of the invention
Within protection scope.
Claims (4)
1. a kind of branched polyamide-glyoxal resin adhesive, it is characterised in that: the branched polyamide-glyoxal resin glue
Stick as three (2- amino-ethyl) amine and urea it is solvent-free, without branching polyamides made from deamination condensation reaction under catalysts conditions
Amine and glyoxal addition, condensation reaction are made, and the branched polyamide-glyoxal resin adhesive is claret uniform liquid
Body, solid content 55-60%, pH 7.0-8.0, Storage period 60 days or more.
2. a kind of branched polyamide-glyoxal resin adhesive according to claim 1, it is characterised in that: the branching
Polyamide molecule branch has-CH2-CH2- NHCONH- repetitive structure and branch terminals are-CH2-CH2-NH-CO-NH2Knot
Structure.
3. the described in any item branched polyamides of claims 1 or 2-glyoxal resin adhesive preparation method, feature exist
In: include the following steps:
A. the reaction incipient stage will measure as T1Three (2- amino-ethyl) amine be warming up to 40-60 DEG C in oil bath, be added with stirring
Metering is U1Urea, the molar ratio U of urea and three (2- amino-ethyl) amine1/T1Control is between 3.5-5.0；Persistently overheating is extremely
110-120 DEG C, insulation reaction is absorbed in reaction process with ammonia absorption device and overflows ammonia；
B. it is T that second of metering is added after insulation reaction 2.0-3.0 hours at 110-120 DEG C2Three (2- amino-ethyl) amine, make
U1/(T1+T2) molar ratio is 0.7-1.0, second of urea, metered amount U is added in insulation reaction after 3.0-4.0 hours2, make (U1+
U2)/(T1+T2) molar ratio be 2.0-2.6, keep the temperature 1.5-2.0 hour, discharging, cool down；
C. product after cooling is three (2- amino-ethyl) amine-urea polyamide solid, in drying box under the conditions of 50-60 DEG C
Deamination 3-4 hours, for use；
D. 40% (mass fraction w%) glyoxal solution pH value for measuring as G is adjusted to 8.0-9.0 at room temperature, in water-bath
In be heated to 40 DEG C or so, urea used in lower three (2- amino-ethyl) amine-urea polyamide by synthesis of stirring calculate plus
Three (2- amino-ethyl) amine-urea polyamide solid for entering metering, makes glyoxal/urea mol ratio 0.8-1.2；Persistently overheating
To 60 DEG C, adjusting pH again after three (2- amino-ethyl) amine-urea polyamide solid all dissolution is 8.0-9.0, and heat preservation is anti-
It answers 1.0-1.5 hours, it is 7.0-8.0 that pH is adjusted after natural cooling, obtains branched polyamide-glyoxal resin adhesive.
4. the described in any item branched polyamides of claims 1 or 2-glyoxal resin adhesive is in wood-based panel industry production
Using.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110734731A (en) * | 2019-11-28 | 2020-01-31 | 西南林业大学 | hyperbranched polyurea aldehyde-free wood adhesive as well as preparation method and application thereof |
| CN110734735A (en) * | 2019-11-28 | 2020-01-31 | 西南林业大学 | high-branched polymer wood adhesive and preparation method and application thereof |
| CN110804415A (en) * | 2019-11-28 | 2020-02-18 | 西南林业大学 | Water-soluble formaldehyde-free wood adhesive and preparation method and application thereof |
| CN113336908A (en) * | 2021-07-20 | 2021-09-03 | 西南林业大学 | Branched polymer-urea-glyoxal copolycondensation resin, preparation method and application thereof |
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| CN110734731A (en) * | 2019-11-28 | 2020-01-31 | 西南林业大学 | hyperbranched polyurea aldehyde-free wood adhesive as well as preparation method and application thereof |
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| CN110804415B (en) * | 2019-11-28 | 2021-07-06 | 西南林业大学 | Water-soluble formaldehyde-free wood adhesive and preparation method and application thereof |
| CN110734731B (en) * | 2019-11-28 | 2021-09-21 | 西南林业大学 | Hyperbranched polyurea aldehyde-free wood adhesive as well as preparation method and application thereof |
| CN113336908A (en) * | 2021-07-20 | 2021-09-03 | 西南林业大学 | Branched polymer-urea-glyoxal copolycondensation resin, preparation method and application thereof |
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