CN108047404A - A kind of water base self-dispersion type thermosetting phenolic resin and preparation method thereof - Google Patents
A kind of water base self-dispersion type thermosetting phenolic resin and preparation method thereof Download PDFInfo
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- CN108047404A CN108047404A CN201711305712.4A CN201711305712A CN108047404A CN 108047404 A CN108047404 A CN 108047404A CN 201711305712 A CN201711305712 A CN 201711305712A CN 108047404 A CN108047404 A CN 108047404A
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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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/18—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenols substituted by carboxylic or sulfonic acid groups
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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
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09J161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
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Abstract
The invention belongs to high polymer material fields.Naphthol sulfonate is introduced on molecular resin main chain, it is water-soluble to assign resin system；Using phenol and the mixed system of naphthol sulfonate, synthesized under bivalent metal ion catalysts conditions.Water base self-dispersion type thermosetting phenolic resin of the present invention, is catalyzed, formaldehyde sprays and feeds intake in batches using bivalent metal ion, and naphthol sulfonate is contained in material system, and material composition includes：1 molar part of phenol, naphthol sulfonate are the 10~20% of phenol, and phenol/formaldehyde molar ratio is 1：1.5~2.0,14~24 mass parts of water, 0.5~5 mass parts of bivalent metal ion catalyst.Water base self-dispersion type thermosetting phenolic resin of the present invention, water dispersible is good, and storage stability is good, caking property and temperature tolerance higher, it is suitable as high shear strength, heat safe water base thermoset structure adhesive, the bonding particularly suitable for phenolic composite in brake block and steel.
Description
Technical field
The invention belongs to high polymer material field, it is related to the synthesis skill of polymer synthesis techniques, more particularly to phenolic resin
Art.
Background technology
Water dispersible phenolic resin is a kind of phenolic resin that can form stable homogeneous liquid dispersed phase in water, is stablized
Property is good, and during storage, appearance, viscosity, water-thinned remain unchanged, and volatile contaminant discharge capacity is small, by from polycondensation or
It adds waterborne curing agent to cure, high crosslink density and adhesion strength can be obtained, as adhesive in use, solvent can be substituted
Type phenolic resin bonds timber, metal, plastics etc..
US6130289 describes a kind of technology of preparing of self-emulsifying resol dispersion liquid.Using in water-soluble first
Introduced in rank phenolic resin containing phenolic resin can reactive functionality modifying agent, sulfonic group, sulphur are contained in the modifying agent side group
The sulfur-containing groups such as acidic group react into sticky opaque liquid at a certain temperature, after filtering grumeleuse, obtain translucent phenolic resin
Dispersion liquid.But this preparation method, it is to be modified on the basis of previously prepared water-soluble resol, in modification
During, there are polycondensation reaction between water-soluble A-stage resin, there is partial gel appearance, finished product rate reduces, Er Qiexu
Want two steps that could complete, preparation process is complicated, and cost is higher.
The content of the invention
The technical problems to be solved by the invention are to provide that a kind of molecular structure is controllable, molecular chain length, water dispersible are good, cut
Good environment protection water-based self-dispersion type thermosetting phenolic resin of shearing stress height, high temperature resistant, resistance to ag(e)ing and preparation method thereof.
The object of the present invention is achieved like this：In a manner of introducing naphthol sulfonate on molecular resin main chain, assign
Resin system is water-soluble；Using phenol and the mixed system of naphthol sulfonate, under bivalent metal ion catalyst action, by naphthalene
Sulfocarbolate is introduced into the molecular backbone of phenolic resin, and it is water-soluble to improve resin.
Water base self-dispersion type thermosetting phenolic resin of the present invention, be catalyzed using bivalent metal ion, formaldehyde in batches
Spraying feeds intake, and naphthol sulfonate is contained in material system, and material composition includes：
1 molar part of phenol, naphthol sulfonate are the 10~20% of phenol, and phenol/formaldehyde molar ratio is 1：1.5~2.0, water 14~
24 mass parts, 0.5~5 mass parts of bivalent metal ion catalyst.
Water base self-dispersion type thermosetting phenolic resin of the present invention, be catalyzed using bivalent metal ion, formaldehyde in batches
Spraying feeds intake, and naphthol sulfonate is contained in material system, and material composition includes：
1 molar part of phenol, naphthol sulfonate are the 13~17% of phenol, and phenol/formaldehyde molar ratio is 1：1.6~1.7, water 17~
21 mass parts, 2~4 mass parts of bivalent metal ion catalyst.
Water base self-dispersion type thermosetting phenolic resin of the present invention, the naphthol sulfonate are beta naphthal -6,8-
The double sylvite of disulfonic acid, one kind in 2,3- dihydroxy naphthlene -6- sodium sulfonates or its combination.
Water base self-dispersion type thermosetting phenolic resin of the present invention, the bivalent metal ion catalyst are hydrogen-oxygen
Change the combination of one or more of manganese, cobalt hydroxide, barium hydroxide, zinc acetate.
The preparation method of water base self-dispersion type thermosetting phenolic resin of the present invention, using formaldehyde is sprayed and fed intake in batches
Technique, including dispensing, one section of polycondensation, two sections of additions and dehydrating condensation process, it is characterised in that：
（1）Dispensing：Phenol, naphthol sulfonate, water, bivalent metal ion catalyst by proportion are added to reaction kettle, disperseed equal
It is even；
（2）One section of polycondensation：Stirring, is warming up to 85~90 DEG C, by formaldehyde and phenol molar ratio 1~1.05：1, it is even by atomizing
Speed adds in formalin to reaction kettle, reacts 1~2h, obtains high-ortho thermoplastic performed polymer；
（3）Two sections of additions：98~100 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in residual formaldehyde solution, reaction 0.5
~1h obtains thermosetting property performed polymer；
（4）Dehydrating condensation：60~80 DEG C of vacuum dehydration condensations, polymerization speed reach 300~350 seconds（150±1℃）, obtain water
Base self-dispersing thermosetting phenolic resin.
The preparation method of water base self-dispersion type thermosetting phenolic resin of the present invention, formaldehyde charging is using metered charge
Atomizer, a diameter of 3~10 μm of atomizing particle.
The preparation method of water base self-dispersion type thermosetting phenolic resin of the present invention, uniformly distributed 3~4 metered charge mists
Change nozzle, 200~400L/h of load.
Water base self-dispersion type thermosetting phenolic resin of the present invention, molecular resin chain length, naphthol sulfonate are distributed in
In molecular backbone structure, water dispersible is good, and storage stability is good, and solidification crosslinking degree is high, and caking property and temperature tolerance higher are suitble to
As high shear strength, heat safe water base thermoset structure adhesive, particularly suitable for phenolic composite in brake block
With the bonding of steel.
Water base self-dispersion type thermosetting phenolic resin preparation method of the present invention, reacting balance is easily controllable, is not easy
Generation gel；Molecular structure and reaction process controllability are strong, and product quality uniformity is high.
Specific embodiment
With reference to embodiment, the invention will be further described, but not as the limitation to technical solution.
Embodiment 1
（1）Dispensing：By 94Kg (1000mol) phenol, the double sylvite of 38Kg (100mol) beta naphthals -6,8- disulfonic acid, 14Kg water,
0.5Kg manganous hydroxides are added to reaction kettle, are uniformly dispersed；
（2）One section of polycondensation：Stirring, is warming up to 85 DEG C, 80Kg formaldehyde is at the uniform velocity added in by 3 metered charge atomizer atomizings
Solution (formaldehyde 30Kg（1000mol）), spray load 200L/h, then a diameter of 3~6 μm of atomizing particle reacts 1h, obtains
High-ortho thermoplastic performed polymer；
（3）Two sections of additions：98 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 40Kg formalins（Formaldehyde 15Kg
（500mol））, spray load 200L/h, then a diameter of 3~6 μm of atomizing particle reacts 0.5h, obtains thermosetting property pre-polymerization
Body；
（4）Dehydrating condensation：78 DEG C of vacuum dehydration condensations, polymerization speed reach 300S（150℃）, reaction terminates, obtain it is water base from
Scattered thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 210mPaS, and water dispersible is good, and water can
95 times of dilution ratio, room temperature shear strength 12.6MPa, 300 DEG C of shear strength 2.8MPa.
Embodiment 2
（1）Dispensing：By 94Kg (1000mol) phenol, the double sylvite of 57Kg (150mol) beta naphthals -6,8- disulfonic acid, 15Kg water,
2Kg cobalt hydroxides are added to reaction kettle, are uniformly dispersed；
（2）One section of polycondensation：Stirring, is warming up to 87 DEG C, 84Kg formaldehyde is at the uniform velocity added in by 3 metered charge atomizer atomizings
Solution (formaldehyde 31.5Kg（1050mol）), spray load 400L/h, then a diameter of 5~10 μm of atomizing particle reacts 2h,
Obtain high-ortho thermoplastic performed polymer；
（3）Two sections of additions：98 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 76Kg formalins（Formaldehyde 28.5Kg
（950mol））, spray load 350L/h, then a diameter of 5~10 μm of atomizing particle reacts 1h, obtains thermosetting property performed polymer；
（4）Dehydrating condensation：80 DEG C of vacuum dehydration condensations, polymerization speed reach 315S（149℃）, reaction terminates, obtain it is water base from
Scattered thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 254mPaS, and water dispersible is good, and water can
100 times of dilution ratio, room temperature shear strength 13.5MPa.
Embodiment 3
（1）Dispensing：By 94Kg (1000mol) phenol, the double sylvite of 76Kg (200mol) beta naphthals -6,8- disulfonic acid, 24Kg water,
5Kg barium hydroxides are added to reaction kettle, are uniformly dispersed；
（2）One section of polycondensation：Stirring, is warming up to 90 DEG C, 81Kg formaldehyde is at the uniform velocity added in by 3 metered charge atomizer atomizings
Solution (formaldehyde 30.375Kg（1012.5mol）), spray load 220L/h, then a diameter of 7~10 μm of atomizing particle reacts
1h obtains high-ortho thermoplastic performed polymer；
（3）Two sections of additions：100 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 50Kg formalins（Formaldehyde 18.75Kg
（625mol））, spray load 300L/h, then a diameter of 7~10 μm of atomizing particle reacts 0.5h, obtains thermosetting property pre-polymerization
Body；
（4）Dehydrating condensation：75 DEG C of vacuum dehydration condensations, polymerization speed reach 320S（151℃）, reaction terminates, obtain it is water base from
Scattered thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 267mPaS, and water dispersible is good, and water can
124 times of dilution ratio, 300 DEG C of shear strength 3.3MPa.
Embodiment 4
（1）Dispensing：By 94Kg (1000mol) phenol, 34.06Kg (130mol) 2,3- dihydroxy naphthlene -6- sodium sulfonates, 17Kg water,
2.5Kg zinc acetates are added to reaction kettle, are uniformly dispersed；
（2）One section of polycondensation：Stirring, is warming up to 86 DEG C, 81.6Kg first is at the uniform velocity added in by 4 metered charge atomizer atomizings
Aldehyde solution (formaldehyde 30.6Kg（1020mol）), spray load 320L/h, then a diameter of 3~6 μm of atomizing particle reacts
1.4h obtains high-ortho thermoplastic performed polymer；
（3）Two sections of additions：99 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 46.4Kg formalins（Formaldehyde 17.4Kg
（580mol））, spray load 360L/h, then a diameter of 3~6 μm of atomizing particle reacts 0.6h, obtains thermosetting property pre-polymerization
Body；
（4）Dehydrating condensation：70 DEG C of vacuum dehydration condensations, polymerization speed reach 335S（150℃）, reaction terminates, obtain it is water base from
Scattered thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 290mPaS, and water dispersible is good, and water can
152 times of dilution ratio, room temperature shear strength 14.3MPa, 300 DEG C of shear strength 3.5MPa.
Embodiment 5
（1）Dispensing：By 94Kg (1000mol) phenol, 39.3Kg (150mol) 2,3- dihydroxy naphthlene -6- sodium sulfonates, 21Kg water,
1Kg zinc acetates are added to reaction kettle, are uniformly dispersed；
（2）One section of polycondensation：Stirring, is warming up to 85 DEG C, 82Kg formaldehyde is at the uniform velocity added in by 4 metered charge atomizer atomizings
Solution (formaldehyde 30.75Kg（1025mol）), spray load 350L/h, then a diameter of 7~10 μm of atomizing particle reacts
1.5h obtains high-ortho thermoplastic performed polymer；
（3）Two sections of additions：100 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 73Kg formalins（Formaldehyde
27.375Kg（912.5mol））, spray load 360L/h, then a diameter of 7~10 μm of atomizing particle reacts 1h, obtains heat
Solidity performed polymer；
（4）Dehydrating condensation：65 DEG C of vacuum dehydration condensations, polymerization speed reach 350S（150.5℃）, reaction terminates, obtains water base
Self-dispersing thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 325mPaS, and water dispersible is good, and water can
179 times of dilution ratio, room temperature shear strength 14.8MPa.
Embodiment 6
（1）Dispensing：By 94Kg (1000mol) phenol, 44.54Kg (170mol) 2,3- dihydroxy naphthlene -6- sodium sulfonates, 20Kg water,
1.5Kg zinc acetates, 2Kg barium hydroxides are added to reaction kettle, are uniformly dispersed；
（2）One section of polycondensation：Stirring, is warming up to 87 DEG C, 82.4Kg first is at the uniform velocity added in by 3 metered charge atomizer atomizings
Aldehyde solution (formaldehyde 30.9Kg（1030mol）), spray load 370L/h, then a diameter of 3~6 μm of atomizing particle reacts
1.6h obtains high-ortho thermoplastic performed polymer；
（3）Two sections of additions：99 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 53.6Kg formalins（Formaldehyde 20.1Kg
（670mol））, spray load 370L/h, then a diameter of 3~6 μm of atomizing particle reacts 0.8h, obtains thermosetting property pre-polymerization
Body；
（4）Dehydrating condensation：78 DEG C of vacuum dehydration condensations, polymerization speed reach 321S（149℃）, reaction terminates, obtain it is water base from
Scattered thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 270mPaS, and water dispersible is good, and water can
178 times of dilution ratio, room temperature shear strength 13.8MPa.
Embodiment 7
（1）Dispensing：By 94Kg (1000mol) phenol, 19Kg (50mol) beta naphthals -6,8- disulfonic acid double sylvite, 15.72Kg
(60mol) 2,3- dihydroxy naphthlene -6- sodium sulfonates, 18Kg water, 4Kg zinc acetates are added to reaction kettle, are uniformly dispersed；
（2）One section of polycondensation：Stirring, is warming up to 88 DEG C, 82Kg formaldehyde is at the uniform velocity added in by 3 metered charge atomizer atomizings
Solution (formaldehyde 30.75Kg（1025mol）), spray load 210L/h, then a diameter of 3~6 μm of atomizing particle reacts
1.5h obtains high-ortho thermoplastic performed polymer；
（3）Two sections of additions：100 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 45Kg formalins（Formaldehyde
16.875Kg（562.5mol））, spray load 200L/h, then a diameter of 3~6 μm of atomizing particle reacts 0.8h, obtains heat
Solidity performed polymer；
（4）Dehydrating condensation：76 DEG C of vacuum dehydration condensations, polymerization speed reach 334S（150℃）, reaction terminates, obtain it is water base from
Scattered thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 285mPaS, and water dispersible is good, and water can
121 times of dilution ratio, 300 DEG C of shear strength 3.4MPa.
Embodiment 8
（1）Dispensing：By 94Kg (1000mol) phenol, 38Kg (100mol) beta naphthals -6,8- disulfonic acid double sylvite, 15.72Kg
(60mol) 2,3- dihydroxy naphthlene -6- sodium sulfonates, 17.5Kg water, 1Kg zinc acetates, 1.6Kg cobalt hydroxides are added to reaction kettle, point
It dissipates uniform；
（2）One section of polycondensation：Stirring, is warming up to 88 DEG C, 81.5Kg first is at the uniform velocity added in by 3 metered charge atomizer atomizings
Aldehyde solution (formaldehyde 30.5625Kg（1018.75mol）), spray load 280L/h, a diameter of 7~10 μm of atomizing particle, then
1h is reacted, obtains high-ortho thermoplastic performed polymer；
（3）Two sections of additions：99 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 55Kg formalins（Formaldehyde 20.625Kg
（687.5mol））, spray load 200L/h, then a diameter of 7~10 μm of atomizing particle reacts 0.75h, it is pre- to obtain thermosetting property
Aggressiveness；
（4）Dehydrating condensation：75 DEG C of vacuum dehydration condensations, polymerization speed reach 318S（151℃）, reaction terminates, obtain it is water base from
Scattered thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 258mPaS, and water dispersible is good, and water can
108 times of dilution ratio, room temperature shear strength 13.6MPa.
Embodiment 9
（1）Dispensing：By 94Kg (1000mol) phenol, 28.5Kg (75mol) beta naphthals -6,8- disulfonic acid double sylvite, 26.2Kg
(100mol) 2,3- dihydroxy naphthlene -6- sodium sulfonates, 20Kg water, 1Kg zinc acetates, 2.2Kg manganous hydroxides are added to reaction kettle, disperse
Uniformly；
（2）One section of polycondensation：Stirring, is warming up to 88 DEG C, 80Kg formaldehyde is at the uniform velocity added in by 3 metered charge atomizer atomizings
Solution (formaldehyde 30Kg（1000mol）), spray load 330L/h, then a diameter of 3~6 μm of atomizing particle reacts 1.3h, obtains
To high-ortho thermoplastic performed polymer；
（3）Two sections of additions：99 DEG C, in whipping process are warming up to, atomizing at the uniform velocity adds in 66Kg formalins（Formaldehyde 24.75Kg
（825mol））, spray load 220L/h, then a diameter of 3~6 μm of atomizing particle reacts 1h, obtains thermosetting property performed polymer；
（4）Dehydrating condensation：60 DEG C of vacuum dehydration condensations, polymerization speed reach 309S（149℃）, reaction terminates, obtain it is water base from
Scattered thermosetting phenolic resin.
The resin is viscous light yellow transparent resin, and the viscosity of 50% aqueous solution is 228mPaS, and water dispersible is good, and water can
136 times of dilution ratio, 300 DEG C of shear strength 2.9MPa.
Claims (9)
1. a kind of water base self-dispersion type thermosetting phenolic resin, is catalyzed, formaldehyde sprays and feeds intake in batches, object using bivalent metal ion
Contain naphthol sulfonate in material system, material composition is：
1 molar part of phenol, naphthol sulfonate are the 10~20% of phenol, and phenol/formaldehyde molar ratio is 1：1.5~2.0, water 14~
24 mass parts, 0.5~5 mass parts of bivalent metal ion catalyst.
2. water base self-dispersion type thermosetting phenolic resin according to claim 1, it is characterised in that：Material forms：
1 molar part of phenol, naphthol sulfonate are the 13~17% of phenol, and phenol/formaldehyde molar ratio is 1：1.6~1.7, water 17~
21 mass parts, 2~4 mass parts of bivalent metal ion catalyst.
3. water base self-dispersion type thermosetting phenolic resin according to claim 1, it is characterised in that：The naphtholsulfonic acid
Salt is the double sylvite of 2-naphthol-6,8-disulfonic acid, one kind in 2,3- dihydroxy naphthlene -6- sodium sulfonates or its combination.
4. water base self-dispersion type thermosetting phenolic resin according to claim 2, it is characterised in that：The naphtholsulfonic acid
Salt is the double sylvite of 2-naphthol-6,8-disulfonic acid, one kind in 2,3- dihydroxy naphthlene -6- sodium sulfonates or its combination.
5. water base self-dispersion type thermosetting phenolic resin according to claim 1, it is characterised in that：The divalent metal
Ionic catalyst is the combination of one or more of manganous hydroxide, cobalt hydroxide, barium hydroxide, zinc acetate.
6. water base self-dispersion type thermosetting phenolic resin according to claim 2, it is characterised in that：The divalent metal
Ionic catalyst is the combination of one or more of manganous hydroxide, cobalt hydroxide, barium hydroxide, zinc acetate.
7. the preparation method of the water base self-dispersion type thermosetting phenolic resin according to claim 1~6 any one uses
Formaldehyde is sprayed charging technology in batches, including dispensing, one section of polycondensation, two sections of additions and dehydrating condensation process, it is characterised in that：
Dispensing：Phenol, naphthol sulfonate, water, bivalent metal ion catalyst by proportion are added to reaction kettle, are uniformly dispersed；
One section of polycondensation：Stirring, is warming up to 85~90 DEG C, by formaldehyde and phenol molar ratio 1~1.05：1, at the uniform velocity added by atomizing
Enter formalin to reaction kettle, react 1~2h, obtain high-ortho thermoplastic performed polymer；
Two sections of additions：It is warming up to 98~100 DEG C, in whipping process, atomizing at the uniform velocity adds in residual formaldehyde solution, reaction 0.5~
1h obtains thermosetting property performed polymer；
Dehydrating condensation：60~80 DEG C of vacuum dehydrations condensation, polymerization speed reach 300~350 seconds/150 ± 1 DEG C, obtain it is water base from
Scattered thermosetting phenolic resin.
8. the preparation method of water base self-dispersion type thermosetting phenolic resin according to claim 7, it is characterised in that：Formaldehyde
Charging is using metered charge atomizer, a diameter of 3~10 μm of atomizing particle.
9. the preparation method of water base self-dispersion type thermosetting phenolic resin according to claim 8, it is characterised in that：It is described
Atomizer is 3~4 uniformly distributed, 200~400L/h of load.
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| CN106085313A (en) * | 2016-06-13 | 2016-11-09 | 北京林业大学 | A kind of thermosetting high adjacent position phenolic resin adhesive and preparation method thereof |
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