CN109293880A - A kind of preparation method of modified o-cresol formaldehyde epoxy resin - Google Patents
A kind of preparation method of modified o-cresol formaldehyde epoxy resin Download PDFInfo
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- CN109293880A CN109293880A CN201811037693.6A CN201811037693A CN109293880A CN 109293880 A CN109293880 A CN 109293880A CN 201811037693 A CN201811037693 A CN 201811037693A CN 109293880 A CN109293880 A CN 109293880A
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/08—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols from phenol-aldehyde condensates
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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Abstract
The invention belongs to polymer-function material fields, provide a kind of preparation method of modified o-cresol formaldehyde epoxy resin, its method is that synthesis modification agent is reacted with isocyanates with hydroxyl dimethyl silicone polymer, by weight, by 10~30 parts of modifying agent, 20~60 parts of o-cresol formaldehyde epoxy resins, 30~70 parts of solvents sequentially add reactor, it stirs and heats to 70~90 DEG C, after mixing to it, catalyst is added, is then heated to 100~160 DEG C of 2~10h of reaction, the modified o-cresol formaldehyde epoxy resin is obtained after cooling.The modification o-cresol formaldehyde epoxy resin obtained using preparation method of the invention has excellent increasing tougheness and heat-resistant stability, excellent electrical property.
Description
Technical field
The invention belongs to polymer-function material fields, and in particular to a kind of preparation side of modified o-cresol formaldehyde epoxy resin
Method.
Background technique
O-cresol formaldehyde epoxy resin is that a kind of line style phenolic aldehyde as obtained by o-cresol-formaldehyde resin and epichlorohydrin reaction is resistance to
Hot multi-functional epoxy resin is connected with an epoxy group on each phenyl ring from can be seen that in molecular structure, with
Bisphenol A type epoxy resin (epoxide number 0.2eq/100g) of the softening point in 70~80 DEG C of sections is compared, o-cresol formaldehyde asphalt mixtures modified by epoxy resin
The epoxide number of rouge is up to 0.5eq/100g or more, and when resin solidification is capable of providing 2.5 times of crosslinking points, and it is close easily to form high crosslinking
The three-dimensional structure of degree, solidfied material is rich in phenolic aldehyde skeleton in addition, shows excellent thermal stability, mechanical strength, electric insulating quality
Energy, water resistance, chemical resistance.
When another distinguishing feature of the resin is softening point variation, epoxide number is substantially unchanged, and melt viscosity phase
When low, impart resin excellent technology stability and processing technology, thus be widely used as semiconductor equipment, integrated circuit,
The capsulation material of the electronic components such as copper-clad plate keeps properties of product and service life to protect electronic component from environmental corrosion.
But the resin is crisp in solidification when property, and toughness is lower, and when temperature is higher, thermal stress is larger, and thermal expansion index is higher,
With circuit board multiple stratification and dystectic lead-free solder it is universal etc. in printed circuit board, semiconductor-encapsulating material
Used resin requires higher and higher.
Summary of the invention
It is an object of the invention to overcome the deficiency of the above-mentioned prior art, a kind of modified o-cresol formaldehyde epoxy resin is provided
Preparation method.The modifying agent reacted by introducing hydroxyl dimethyl silicone polymer with isocyanates, chemical modification o-cresol
Nitrogen, silicon synergistic flame-retardant system are introduced into o-cresol formaldehyde epoxy resin by formaldehyde epoxy resin.The program is in addition to that can improve material
Heat-resisting, flame retardant effect, play synergistic effect outside, moreover it is possible to play the effect of toughening.
In order to solve the above technical problems, the preparation method of modification o-cresol formaldehyde epoxy resin of the invention, including walk as follows
It is rapid:
(1) preparation of modifying agent
Hydroxyl dimethyl silicone polymer is added in reaction vessel, N is led to2Protection, is warming up to 50~60 DEG C, is added dropwise and hydroxyl
The isocyanates that 1~2 times mole of base dimethyl silicone polymer, 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, rise
Temperature reacts 2~6h to 80~95 DEG C；When temperature reaches 100~120 DEG C, vacuum dehydration terminates when reaching -0.1MPa, obtains adjacent first
Novolac epoxy resin modifying agent, wherein the hydroxyl dimethyl silicone polymer is selected from the compound of following general structure:
Wherein n is 1~10,
It is as follows that it reacts synthetic route:
(2) preparation of modified o-cresol formaldehyde epoxy resin
By weight, by 10~30 parts of o-cresol formaldehyde epoxy resin modifying agent, 20~60 parts of o-cresol formaldehyde epoxy resins,
30~70 parts of solvents sequentially add reactor, stir and heat to 70~90 DEG C, after mixing to it, catalysis are added
Then agent is heated to 100~160 DEG C of 2~10h of reaction, the modified o-cresol formaldehyde epoxy resin is obtained after cooling.
In the preferred technical solution of the present invention, wherein the isocyanates is selected from toluene di-isocyanate(TDI), diphenylmethyl
One of alkane diisocyanate, isophorone diisocyanate, dicyclohexyl methyl hydride diisocyanate are a variety of, preferably first
Phenylene diisocyanate.
In the preferred technical solution of the present invention, wherein the o-cresol formaldehyde epoxy resin is selected from EOCN-6850, EOCN-
6950, one of CNE-202, NPCN-704 or a variety of, preferably EOCN-6850.
In the preferred technical solution of the present invention, wherein the solvent is selected from benzene, toluene, chlorobenzene, methyl iso-butyl ketone (MIBK), fourth
One of alcohol, cyclohexanone are a variety of, preferably cyclohexanone.
In the preferred technical solution of the present invention, wherein the catalyst is selected from zinc naphthenate, nitric acid, salicylic acid, tetramethyl
One of base ammonium hydroxide is a variety of, preferably zinc naphthenate.
The preparation method of modified o-cresol formaldehyde epoxy resin, includes the following steps:
(1) preparation of modifying agent
Hydroxyl dimethyl silicone polymer is added in four-hole bottle, leads to N2 protection, is warming up to 60 DEG C, be added dropwise and hydroxyl poly- two
The isocyanates that 1~2 times mole of methylsiloxane, 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, it is warming up to 80
~95 DEG C, react 2~6h；After reaction, vacuum dehydration, when temperature reaches 100~120 DEG C, when vacuum degree reaches -0.1MPa
Dehydration terminates, and obtains o-cresol formaldehyde epoxy resin modifying agent, wherein the hydroxyl dimethyl silicone polymer is selected from as flowering structure is logical
The compound of formula:
Wherein n is 1~10,
It is as follows that it reacts synthetic route:
(2) preparation of modified o-cresol formaldehyde epoxy resin
By weight, by 10~30 parts of modifying agent, 20~60 parts of o-cresol formaldehyde epoxy resins, 30~70 parts of solvents are successively
Reactor is added, stirs and heats to 70~90 DEG C, after mixing to it, catalyst is added, is then heated to
100~160 DEG C of 2~10h of reaction, obtain the modified o-cresol formaldehyde epoxy resin after cooling.
Compared with prior art, the advantages and effects of the present invention are:
(1) modifying agent that the present invention synthesizes, phenyl content is high, improves the solubility parameter of modifier components, increases
With the compatibility of o-cresol formaldehyde epoxy resin so that product have good storage stability；Meanwhile the phenyl of high-content also mentions
The high high temperature resistance of product.
(2) modifying agent that the present invention synthesizes, introduces isocyanate groups, can be with hydroxyl, water, the amine in hydroxy compounds
And the compound reaction with active hydrogen generates carbamate, urea, semicarbazides and biuret etc., improves the toughness of product.
(3) organosilicon itself has good plasticity and heat-resistant stability, further improves material processing performance.
(4) modified o-cresol formaldehyde epoxy resin prepared by the present invention also has resistance to ultraviolet other than good toughness, high temperature resistant
The features such as aging, high hardness, gives substrate multiple protective.
Specific embodiment
Above scheme is described further below in conjunction with specific embodiment.It should be understood that these embodiments are for illustrating
The present invention and be not limited to limit the scope of the invention.Implementation condition used in the examples can be done according to the condition of specific producer
Further adjustment, the implementation condition being not specified is usually the condition in routine experiment.
Embodiment 1
Blender, thermometer and high performance reflux condenser are being housed, and are being equipped with tetra- mouthfuls of 500ml of drying tube in condensation nozzle
In flask, with the air in N2 displacement bottle falling, 148g (1mol) hydroxyl dimethyl silicone polymer is added, is warming up to 60 DEG C, is added dropwise
174g (1mol) toluene di-isocyanate(TDI), 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, 90 DEG C are warming up to, instead
Answer 4h；After reaction, vacuum dehydration, being dehydrated when temperature reaches 100 DEG C, and vacuum degree reaches -0.1MPa terminates, and obtains o-cresol
Formaldehyde epoxy resin modifying agent；
10g modifying agent, 20gEOCN-6850 are weighed, 30g cyclohexanone is added sequentially to equipped with blender, thermometer and height
Reflux condensing tube is imitated, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, is slowly stirred and heats to 80
DEG C, after mixing to it, 0.05g zinc naphthenate is added, then heats to 120 DEG C, reacts 4h, and constantly separate reaction
The water generated in the process, cooling obtain modified o-cresol formaldehyde epoxy resin 1.
Embodiment 2
Blender, thermometer and high performance reflux condenser are being housed, and are being equipped with tetra- mouthfuls of 500ml of drying tube in condensation nozzle
In flask, with the air in N2 displacement bottle falling, 148g (1mol) hydroxyl dimethyl silicone polymer is added, is warming up to 60 DEG C, is added dropwise
174g (1mol) toluene di-isocyanate(TDI), 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, 90 DEG C are warming up to, instead
Answer 4h；After reaction, vacuum dehydration, being dehydrated when temperature reaches 100 DEG C, and vacuum degree reaches -0.1MPa terminates, and obtains o-cresol
Formaldehyde epoxy resin modifying agent；
10g modifying agent, 40gEOCN-6850 are weighed, 50g cyclohexanone is added sequentially to equipped with blender, thermometer and height
Reflux condensing tube is imitated, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, is slowly stirred and heats to 80
DEG C, after mixing to it, 0.1g zinc naphthenate is added, then heats to 140 DEG C, reacts 5h, and constantly separate reaction
The water generated in the process, cooling obtain modified o-cresol formaldehyde epoxy resin 2.
Embodiment 3
Blender, thermometer and high performance reflux condenser are being housed, and are being equipped with tetra- mouthfuls of 500ml of drying tube in condensation nozzle
In flask, with the air in N2 displacement bottle falling, 148g (1mol) hydroxyl dimethyl silicone polymer is added, is warming up to 60 DEG C, is added dropwise
174g (1mol) toluene di-isocyanate(TDI), 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, 90 DEG C are warming up to, instead
Answer 4h；After reaction, vacuum dehydration, being dehydrated when temperature reaches 100 DEG C, and vacuum degree reaches -0.1MPa terminates, and obtains o-cresol
Formaldehyde epoxy resin modifying agent；
10g modifying agent, 60gEOCN-6850 are weighed, 70g cyclohexanone is added sequentially to equipped with blender, thermometer and height
Reflux condensing tube is imitated, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, is slowly stirred and heats to 80
DEG C, after mixing to it, 0.15g zinc naphthenate is added, then heats to 160 DEG C, reacts 6h, and constantly separate reaction
The water generated in the process, cooling obtain modified o-cresol formaldehyde epoxy resin 3.
Embodiment 4
Blender, thermometer and high performance reflux condenser are being housed, and are being equipped with tetra- mouthfuls of 500ml of drying tube in condensation nozzle
In flask, with the air in N2 displacement bottle falling, 148g (1mol) hydroxyl dimethyl silicone polymer is added, is warming up to 60 DEG C, is added dropwise
174g (1mol) toluene di-isocyanate(TDI), 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, 90 DEG C are warming up to, instead
Answer 4h；After reaction, vacuum dehydration, being dehydrated when temperature reaches 100 DEG C, and vacuum degree reaches -0.1MPa terminates, and obtains o-cresol
Formaldehyde epoxy resin modifying agent；
30g modifying agent, 40gEOCN-6850 are weighed, 50g cyclohexanone is added sequentially to equipped with blender, thermometer and height
Reflux condensing tube is imitated, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, is slowly stirred and heats to 80
DEG C, after mixing to it, 0.12g zinc naphthenate is added, then heats to 120 DEG C, reacts 4h, and constantly separate reaction
The water generated in the process, cooling obtain modified o-cresol formaldehyde epoxy resin 4.
Embodiment 5
Blender, thermometer and high performance reflux condenser are being housed, and are being equipped with tetra- mouthfuls of 500ml of drying tube in condensation nozzle
In flask, with the air in N2 displacement bottle falling, 148g (1mol) hydroxyl dimethyl silicone polymer is added, is warming up to 60 DEG C, is added dropwise
174g (1mol) toluene di-isocyanate(TDI), 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, 90 DEG C are warming up to, instead
Answer 4h；After reaction, vacuum dehydration, being dehydrated when temperature reaches 100 DEG C, and vacuum degree reaches -0.1MPa terminates, and obtains o-cresol
Formaldehyde epoxy resin modifying agent；
30g modifying agent, 20gEOCN-6850 are weighed, 30g cyclohexanone is added sequentially to equipped with blender, thermometer and height
Reflux condensing tube is imitated, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, is slowly stirred and heats to 80
DEG C, after mixing to it, 0.1g zinc naphthenate is added, then heats to 140 DEG C, reacts 5h, and constantly separate reaction
The water generated in the process, cooling obtain modified o-cresol formaldehyde epoxy resin 5.
Embodiment 6
Blender, thermometer and high performance reflux condenser are being housed, and are being equipped with tetra- mouthfuls of 500ml of drying tube in condensation nozzle
In flask, with the air in N2 displacement bottle falling, 148g (1mol) hydroxyl dimethyl silicone polymer is added, is warming up to 60 DEG C, is added dropwise
174g (1mol) toluene di-isocyanate(TDI), 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, 90 DEG C are warming up to, instead
Answer 4h；After reaction, vacuum dehydration, being dehydrated when temperature reaches 100 DEG C, and vacuum degree reaches -0.1MPa terminates, and obtains o-cresol
Formaldehyde epoxy resin modifying agent；
20g modifying agent, 60gEOCN-6850 are weighed, 70g cyclohexanone is added sequentially to equipped with blender, thermometer and height
Reflux condensing tube is imitated, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, is slowly stirred and heats to 80
DEG C, after mixing to it, 0.15g zinc naphthenate is added, then heats to 160 DEG C, reacts 8h, and constantly separate reaction
The water generated in the process, cooling obtain modified o-cresol formaldehyde epoxy resin 6.
Comparative example 1
20gEOCN-6850 is weighed, 30g cyclohexanone is added sequentially to equipped with blender, thermometer and efficient backflow condensation
Pipe, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, it is slowly stirred and heats to 80 DEG C, to its mixing
After uniformly, 0.05g zinc naphthenate is added, then heats to 120 DEG C, reacts 4h, and constantly separate in reaction process and generate
Water, cooling obtain comparison o-cresol formaldehyde epoxy resin 1.
Comparative example 2
40gEOCN-6850 is weighed, 50g cyclohexanone is added sequentially to equipped with blender, thermometer and efficient backflow condensation
Pipe, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, it is slowly stirred and heats to 80 DEG C, to its mixing
After uniformly, 0.1g zinc naphthenate is added, then heats to 140 DEG C, react 5h, and constantly separates and generated in reaction process
Water, cooling obtain comparison o-cresol formaldehyde epoxy resin 2.
Comparative example 3
60gEOCN-6850 is weighed, 70g cyclohexanone is added sequentially to equipped with blender, thermometer and efficient backflow condensation
Pipe, and in 500ml four-hole boiling flask of the condensation nozzle equipped with drying tube, it is slowly stirred and heats to 80 DEG C, to its mixing
After uniformly, 0.15g zinc naphthenate is added, then heats to 160 DEG C, reacts 8h, and constantly separate in reaction process and generate
Water, cooling obtain comparison o-cresol formaldehyde epoxy resin 3.
Modification o-cresol formaldehyde epoxy resin product prepared by the embodiment of the present invention and unmodified o-cresol formaldehyde epoxy resin
Properties of product comparison such as table 1
Table 1 is modified o-cresol formaldehyde epoxy resin performance test
As seen from the above table, using modified o-cresol formaldehyde epoxy resin provided by the invention, resin can significantly be improved
Toughness and high-temperature heat-resistance performance.
The foregoing examples are merely illustrative of the technical concept and features of the invention, its object is to allow person skilled in the art's energy
The solution contents of the present invention much of that are simultaneously implemented accordingly, and it is not intended to limit the scope of the present invention.It is all spiritual according to the present invention
The equivalent transformation or modification that essence is done, should be covered by the protection scope of the present invention.
Claims (5)
1. the preparation method of modified o-cresol formaldehyde epoxy resin, includes the following steps:
(1) preparation of modifying agent
Hydroxyl dimethyl silicone polymer is added in reaction vessel, N is led to2Protection is warming up to 50~60 DEG C, is added dropwise poly- with hydroxyl
The isocyanates that 1~2 times mole of dimethyl siloxane, 60~70 DEG C of reaction temperature of control during being added dropwise；After dripping off, it is warming up to
80~95 DEG C, react 2~6h；When temperature reaches 100~120 DEG C, vacuum dehydration terminates when reaching -0.1MPa, obtains o-cresol formaldehyde
Epoxy resin modification agent, wherein the hydroxyl dimethyl silicone polymer is selected from the compound of following general structure:
Wherein n is 1~10,
It is as follows that it reacts synthetic route:
(2) preparation of modified o-cresol formaldehyde epoxy resin
By weight, by 10~30 parts of o-cresol formaldehyde epoxy resin modifying agent, 20~60 parts of o-cresol formaldehyde epoxy resins, 30~
70 parts of solvents sequentially add reactor, stir and heat to 70~90 DEG C, after mixing to it, catalyst are added, so
After be heated to 100~160 DEG C of 2~10h of reaction, the modified o-cresol formaldehyde epoxy resin is obtained after cooling.
2. preparation method according to claim 1, which is characterized in that the isocyanates is selected from toluene diisocynate
One of ester, methyl diphenylene diisocyanate, isophorone diisocyanate, dicyclohexyl methyl hydride diisocyanate are more
Kind.
3. preparation method according to claim 1, which is characterized in that the o-cresol formaldehyde epoxy resin is selected from EOCN-
6850, one of EOCN-6950, CNE-202, NPCN-704 or a variety of.
4. preparation method according to claim 1, which is characterized in that the solvent is selected from benzene, toluene, chlorobenzene, methyl
One of isobutyl ketone, butanol, cyclohexanone are a variety of.
5. preparation method according to claim 1, which is characterized in that the catalyst is selected from zinc naphthenate, nitric acid, water
One of poplar acid, tetramethylammonium hydroxide are a variety of.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811037693.6A CN109293880A (en) | 2018-09-06 | 2018-09-06 | A kind of preparation method of modified o-cresol formaldehyde epoxy resin |
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| CN201811037693.6A CN109293880A (en) | 2018-09-06 | 2018-09-06 | A kind of preparation method of modified o-cresol formaldehyde epoxy resin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113773653A (en) * | 2021-09-08 | 2021-12-10 | 广东致格纳米科技有限公司 | Preparation method of modified novolac epoxy resin |
| CN117625031A (en) * | 2024-01-23 | 2024-03-01 | 山东默特尔工程科技有限公司 | Preparation method of wear-resistant corrosion-resistant polyurethane self-leveling floor coating |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113773653A (en) * | 2021-09-08 | 2021-12-10 | 广东致格纳米科技有限公司 | Preparation method of modified novolac epoxy resin |
| CN113773653B (en) * | 2021-09-08 | 2022-10-14 | 广东致格纳米科技有限公司 | Preparation method of modified novolac epoxy resin |
| CN117625031A (en) * | 2024-01-23 | 2024-03-01 | 山东默特尔工程科技有限公司 | Preparation method of wear-resistant corrosion-resistant polyurethane self-leveling floor coating |
| CN117625031B (en) * | 2024-01-23 | 2024-04-19 | 山东默特尔工程科技有限公司 | Preparation method of wear-resistant corrosion-resistant polyurethane self-leveling floor coating |
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