CN110951252A - Novel cyanate/epoxy modified resin matrix composition - Google Patents
Novel cyanate/epoxy modified resin matrix composition Download PDFInfo
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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Abstract
The invention provides a novel cyanate/epoxy modified resin matrix composition, which comprises the following components: a cyanate ester monomer to provide a cyanate ester group-OCN; a first multifunctional epoxy compound for providing an epoxy group epoxy; and a second multifunctional epoxy compound for providing a hydroxyl group-OH, wherein the molar ratio of the cyanate group-OCN to the epoxy group epoxy is 1.5: 1-1: 1.5, and the molar ratio of the cyanate group-OCN to the hydroxyl group-OH is 1: 1-3: 1. The novel cyanate/epoxy modified resin matrix composition has low raw material cost and high mechanical property.
Description
Technical Field
The invention relates to a modified resin matrix composition, in particular to a novel cyanate/epoxy modified resin matrix composition.
Background
The cyanate resin is a thermosetting resin with excellent dielectric property, mechanical property, heat resistance and low water absorption rate, and has wide application prospect in the fields of high-performance circuit boards, wave-transmitting structural materials, high-toughness structural materials and the like. Since the industrial synthesis in 1970's, cyanate ester resins have been studied by researchers as the most promising high performance resin matrix, and have attracted the continuous attention of various fields of application in the industry.
In the modification method of cyanate, cyanate/epoxy modification is an important system, and the excellent dielectric property and heat resistance of cyanate are combined with the good manufacturability of epoxy, so that the thermosetting resin with good processability and comprehensive performance can be obtained. In practice, however, cyanate/epoxy modified resin has a problem of low mechanical strength, the bending strength of the cyanate/epoxy modified resin is usually lower than 130MPa, and when the cyanate/epoxy modified resin is used as a composite material matrix, the bending strength of the cured resin is usually in the range of 130-100 MPa, and the application of the cyanate/epoxy modified resin in the field of high-performance resin-based composite materials is limited by the level of the mechanical properties.
Heretofore, some methods have been used to improve the mechanical properties of cyanate ester modified resins. For example, ZL200910052209.1 (high-toughness cyanate ester co-cured resin and a preparation method thereof) improves the bending strength of the cured resin to a level of 150-130 MPa by means of cyanate ester, bismaleimide, epoxy resin and bisoxazoline modification. ZL201210169553.0 (cyanate-bis-oxazoline-polyethylene glycol resin composition) and ZL201210169441.5 (cyanate-epoxy-bis-oxazoline-polyethylene glycol resin composition) also have similar mechanical property performances. ZL201110178424.3 (thermosetting modified cyanate ester resin and preparation method thereof) can even improve the bending strength of the cured resin to a level of >150MPa by means of cyanate ester, oxygen resin and bisoxazoline modification. However, these methods require the use of expensive raw materials such as bisoxazoline compounds, bismaleimides, etc., which are disadvantageous for industrial applications.
Disclosure of Invention
The present invention has been made to solve the above problems, and an object of the present invention is to provide a novel cyanate ester/epoxy modified resin matrix composition.
The invention provides a novel cyanate/epoxy modified resin matrix composition having the following characteristics: a cyanate ester monomer to provide a cyanate ester group-OCN; a first multifunctional epoxy compound for providing an epoxy group epoxy; and a second polyfunctional epoxy compound for providing a hydroxyl group-OH, wherein the molar ratio of cyanate group-OCN to epoxy group epoxy is 1.5:1 to 1:1.5, and the molar ratio of cyanate group-OCN to hydroxyl group-OH is 1:1 to 3: 1.
The novel cyanate/epoxy modified resin matrix composition provided by the invention can also have the following characteristics: wherein the cyanate monomer is one or a prepolymer of bisphenol A cyanate, bisphenol L cyanate, bisphenol M cyanate and phenolic cyanate.
The novel cyanate/epoxy modified resin matrix composition provided by the invention can also have the following characteristics: wherein the first multifunctional epoxy compound is a multifunctional epoxy compound with a high epoxy value.
The novel cyanate/epoxy modified resin matrix composition provided by the invention can also have the following characteristics: wherein the second polyfunctional epoxy compound is a polyfunctional epoxy compound with a low epoxy value.
The novel cyanate/epoxy modified resin matrix composition provided by the invention can also have the following characteristics: wherein the ratio of cyanate ester group-OCN to epoxide group epoxy is 1:1mol/mol, and the molar ratio of cyanate ester group-OCN to hydroxyl group-OH is 3: 1.
Action and Effect of the invention
According to the novel cyanate/epoxy modified resin matrix composition, cyanate monomers, a polyfunctional epoxy compound with a high epoxy value and a polyfunctional epoxy compound with a low epoxy value are adopted, and the resin is obtained through the processes of heating, catalyzing, stirring, high-temperature vacuum drying and degassing, pouring into a mold and curing treatment.
Therefore, the novel cyanate/epoxy modified resin matrix composition of the present invention constructs a novel cyanate/epoxy modified resin system of-OCN/-OH/epoxy based on the fact that the hydroxyl-OH reacts with cyanate ester group-OCN and epoxy group epoxy to cure, and will improve the mechanical properties of the cured resin in a low cost manner.
Detailed Description
In order to make the technical means and functions of the invention easy to understand, the invention is specifically described with reference to the following embodiments.
The inventor finds in research that the function of hydroxyl-OH has been neglected in the past in the research process of cyanate/epoxy modified resin.
Researchers generally consider that processes such as triazinylation polymerization of cyanate ester between cyanate ester group-OCN and epoxy group epoxy, isomerization of triazine ring to form isocyanuric ring in the presence of epoxy, reaction of isocyanuric ring with epoxy to form oxazoline ketone ring, and self-polymerization of epoxy occur. The properties of the cyanate/epoxy modified system established on the basis are basically in the comprehensive average state of the properties of cyanate resin and epoxy resin, and the outstanding performance is that the heat resistance (such as glass transition temperature, Tg) is equivalent to that of an epoxy/amine curing system, but is reduced compared with that of the cyanate cured resin. Mechanical properties such as bending strength <130MPa, fail to give play to the high mechanical properties of both resin matrices.
Through research, the inventor finds that hydroxyl-OH is a considerable important factor in the reaction between cyanate ester group-OCN and epoxy group epoxy. The hydroxyl-OH groups are inherent in the structure of the epoxy monomers and differ only in the number of hydroxyl-OH groups in different epoxy monomers. In the presence of hydroxyl-OH, the cyanate/epoxy modified curing reaction pathway comprises: self-polymerizing cyanate ester group-OCN to generate triazine ring, reacting cyanate ester group-OCN with hydroxyl-OH to generate imido carbonate, reacting imido carbonate to generate triazine ring and release hydroxyl-OH, carrying out alcoholysis reaction on triazine ring at high temperature to generate carbamate, reacting carbamate to generate isocyanuric ring, reacting carbamate with epoxy to generate tertiary amino carbonate, and self-polymerizing epoxy to generate ether. Under the condition of enough hydroxyl-OH, more epoxy groups epoxy participate in the reaction to generate tertiary amine carbonate, so that more chemical crosslinking exists between cyanate ester and epoxy, and the properties, particularly the mechanical properties, of the cured resin are favorably improved. It was found that by ensuring a certain amount of hydroxyl-OH in the system, the flexural strength can be easily increased to a level >130 MPa.
Therefore, the invention provides a novel cyanate/epoxy modified resin matrix composition with low cost, which can improve the mechanical property of a cyanate/epoxy modified resin system, namely, the mechanical property of the cured resin can be effectively improved by adjusting and controlling the number of hydroxyl-OH in the cyanate/epoxy system.
Epoxy monomers of bisphenol A type, such as E-20, E-12, E-06, E-03, of medium and high molecular weight are the major source of hydroxyl-OH. The epoxy monomers are mainly used for preparing epoxy paint, have low cost and can be directly synthesized by bisphenol A and epoxy chloropropane, or obtained by further reacting low molecular epoxy such as E-51 and the like with bisphenol A. The advantage of using these epoxies as a source of hydroxyl-OH is that there are no compatibility issues with cyanate esters/epoxies and thus no concerns about process effects and the drawback of phase separation upon curing.
The invention relates to a novel cyanate/epoxy modified resin matrix composition, which comprises the following components in percentage by weight: cyanate ester monomer, first multifunctional epoxy compound and second multifunctional epoxy compound.
Cyanate ester monomers are used to provide cyanate ester groups — OCN.
In the invention, the cyanate ester monomer is one or a prepolymer of one of bisphenol A type cyanate ester (4,4' -dicyanate phenyl-propane, BADCy), bisphenol L type cyanate ester (4,4' -dicyanate phenyl-ethane, BEDCy), bisphenol M type cyanate ester (4,4' - [1, 3-phenylbis (1-methyl-ethylidene) ] bisphenyl cyanate ester), phenolic type cyanate ester (PT) and the like.
The first multifunctional epoxy compound is used to provide the epoxy group epoxy.
In the present invention, the first multifunctional epoxy compound is a high epoxy value multifunctional epoxy compound, the type of the multifunctional epoxy resin as the epoxy group epoxy is not limited, and various grades of commercially available multifunctional epoxy resins can be used in the present invention.
A second polyfunctional epoxy compound is used to provide the hydroxy-OH.
In the present invention, the second polyfunctional epoxy compound is a polyfunctional epoxy compound having a low epoxy value, and the epoxy monomers suitable for the source of hydroxy-OH are E-20, E-12, E-06, E-03. These are all commercial industrial raw materials, and can be selected according to different brands of different epoxy production enterprises when in use.
The molar ratio of cyanate ester group-OCN to epoxy group epoxy is 1.5:1 to 1: 1.5.
The molar ratio of cyanate ester group-OCN to hydroxyl group-OH is 1:1 to 3: 1.
Further, in the present invention, the ratio of cyanate group-OCN to epoxy group epoxy is 1:1mol/mol, and the ratio of cyanate group-OCN to hydroxyl group-OH is 3:1 mol/mol.
The novel cyanate/epoxy modified resin matrix composition can be prepared by a melting method, namely, raw materials of the components are fully melted and uniformly mixed at the temperature of 80-120 ℃ to obtain uncured resin. Or dissolving with DMF, butanone, acetone or other solvent to obtain resin glue solution, which can be used to impregnate reinforcing material, such as glass cloth, carbon fiber cloth, etc. for forming composite material.
In addition, the novel cyanate ester/epoxy modified resin matrix composition of the present invention requires the addition of an organometallic compound as a catalyst during curing. Commonly used organometallic compound catalysts are for example: organotins (stannous octoate, dibutyltin dilaurate, derivatives thereof, and the like), organomagnesiums (manganese octoate, manganese acetylacetonate, cyclopentadienyl manganese carbonyl, and the like), organozincs (zinc octoate, zinc acetylacetonate), and further iron acetylacetonate, nickel acetylacetonate, cobalt acetylacetonate, copper acetylacetonate, and the like.
The invention has the advantages that on the basis of the fact that the hydroxyl (-OH) and cyanate ester (-OCN) and epoxy group (epoxy) are subjected to curing reaction, a novel cyanate ester/epoxy modified resin system of-OCN/-OH/epoxy is constructed, and the mechanical property of the cured resin is improved in a low-cost manner.
< example 1 >
Weighing 21.08g of epoxy E-20, 1.77g of epoxy E-51 and 7.15g of bisphenol A cyanate ester (BADCy) in a beaker, heating to 80-100 ℃ to be melted uniformly, adding a certain amount of organic tin catalyst, stirring uniformly, degassing in a vacuum drying oven at 80 ℃ for 10 minutes, pouring into a mold coated with a silicon ester release agent, and curing in an electronic oven. Curing treatment is carried out according to the process of 150 ℃/30min +180 ℃/30min +200 ℃/30min +220 ℃/1h +230 ℃/1h, thus obtaining the resin A.
In this example, the molar ratio of each reactive group is: -OCN: -OH epoxy ═ 1:1: 1.
The resin A is brown yellow solid resin, the bending strength is 157.2MPa, and the bending modulus is 3.55 GPa.
< example 2 >
Resin B was obtained by weighing 12.53g of epoxy E-20, 8.10g of epoxy E-51 and 9.36g of bisphenol A type cyanate ester (BADCy) and processing in the same manner as in example 1.
In this example, the molar ratio of each reactive group is: -OCN epoxy 1:1mol/mol, -OCN OH 2:1 mol/mol.
The resin B is brown yellow solid resin, the bending strength is 152.0MPa, and the bending modulus is 3.45 GPa.
< example 3 >
Resin C was obtained by weighing 8.37g of epoxy E-20, 11.18g of epoxy E-51 and 10.44g of bisphenol A type cyanate ester (BADCy) and processing in the same manner as in example 1.
In this example, the molar ratio of each reactive group is: -OCN epoxy 1:1mol/mol, -OCN OH 3:1 mol/mol.
The resin C is brown yellow solid resin, and has the bending strength of 151.2MPa and the bending modulus of 3.39 GPa.
< example 4 >
Resin D was obtained by weighing 5.90g of epoxy E-20, 13.01g of epoxy E-51 and 11.07g of bisphenol A type cyanate ester (BADCy) and processing in the same manner as in example 1.
In this example, the molar ratio of each reactive group is: -OCN epoxy 1:1mol/mol, -OCN OH 4:1 mol/mol.
The resin D is a brown yellow solid resin, the bending strength is 135.4MPa, and the bending modulus is 3.65 GPa.
< example 5 >
Resin E was obtained by weighing 6.68g of epoxy E-20, 12.87g of o-cresol novolac epoxy CNE and 10.45g of bisphenol A type cyanate ester (BADCy) in a beaker in the same manner as in example 1.
In this example, the molar ratio of each reactive group is: -OCN epoxy 1:1mol/mol, -OCN OH 3:1 mol/mol.
The resin E is a brownish red solid resin, the bending strength is 141.3MPa, and the bending modulus is 4.02 GPa.
< comparative example 1 >
Pure cyanate ester curing resin. Resin F was obtained by weighing 30g of bisphenol A type cyanate ester (BADCy) in a beaker and processing in the same manner as in example 1.
The resin F is a brown yellow solid resin, the bending strength is 113.9MPa, and the bending modulus is 4.11 GPa.
< comparative example 2 >
Cyanate ester/epoxy (BADCy/E-51) resins. Resin G was obtained by weighing 17.39G of epoxy E-51 and 12.61G of bisphenol A type cyanate (BADCy) and processing in the same manner as in example 1.
In this example, the molar ratio of each reactive group is: -OCN epoxy 1:1mol/mol, -OCN OH 11.8:1 mol/mol.
The resin G is a brown yellow solid resin, the bending strength is 126.2MPa, and the bending modulus is 3.72 GPa.
TABLE 1 characterization results of resin A to resin G
| Resin composition | A | B | C | D | E | F | G |
| Flexural Strength (MPa) | 157.2 | 152.0 | 151.2 | 135.4 | 141.3 | 113.9 | 126.2 |
| Flexural modulus (GPa) | 3.55 | 3.45 | 3.39 | 3.65 | 4.02 | 4.11 | 3.72 |
Effects and effects of the embodiments
As can be seen from table 1, the resins of examples 1 to 5 have improved flexural strength and flexural modulus compared to comparative examples 1 and 2.
The novel cyanate/epoxy modified resin matrix composition of embodiments 1 to 5 uses cyanate ester monomer, high epoxy value multifunctional epoxy compound and low epoxy value multifunctional epoxy compound, and the resin is obtained through the processes of heating, catalysis, stirring, high temperature vacuum drying degassing, pouring into a mold and curing treatment.
Therefore, the novel cyanate/epoxy modified resin matrix composition of the present invention constructs a novel cyanate/epoxy modified resin system of-OCN/-OH/epoxy based on the fact that the hydroxyl-OH reacts with cyanate ester group-OCN and epoxy group epoxy to cure, and will improve the mechanical properties of the cured resin in a low cost manner.
The above embodiments are preferred examples of the present invention, and are not intended to limit the scope of the present invention.
Claims (5)
1. A novel cyanate/epoxy modified resin matrix composition, comprising:
a cyanate ester monomer to provide a cyanate ester group-OCN;
a first multifunctional epoxy compound for providing an epoxy group epoxy; and
a second polyfunctional epoxy compound for providing a hydroxyl group-OH,
wherein the molar ratio of the cyanate ester group-OCN to the epoxy group epoxy is 1.5:1 to 1:1.5,
the molar ratio of the cyanate ester group-OCN to the hydroxyl group-OH is 1: 1-3: 1.
2. The novel cyanate/epoxy modified resin matrix composition according to claim 1, wherein:
the cyanate monomer is one or a prepolymer of bisphenol A cyanate, bisphenol L cyanate, bisphenol M cyanate and phenolic cyanate.
3. The novel cyanate/epoxy modified resin matrix composition according to claim 1, wherein:
wherein the first multifunctional epoxy compound is a multifunctional epoxy compound with a high epoxy value.
4. The novel cyanate/epoxy modified resin matrix composition according to claim 1, wherein:
wherein the second polyfunctional epoxy compound is a polyfunctional epoxy compound with a low epoxy value.
5. The novel cyanate/epoxy modified resin matrix composition according to claim 1, wherein:
wherein the ratio of the cyanate ester group-OCN to the epoxy group epoxy is 1:1mol/mol,
the molar ratio of the cyanate ester group-OCN to the hydroxyl group-OH is 3: 1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111732929A (en) * | 2020-07-07 | 2020-10-02 | 遂宁立讯精密工业有限公司 | Cyanate ester adhesive with low curing temperature and high thermal stability and preparation method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103665326A (en) * | 2013-09-26 | 2014-03-26 | 同济大学 | Thermosetting cyanate/bismaleimide resin composition |
| CN105038223A (en) * | 2015-06-02 | 2015-11-11 | 长春长光宇航复合材料有限公司 | Cyanate resin for hot-melt prepregs and preparation method thereof |
-
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103665326A (en) * | 2013-09-26 | 2014-03-26 | 同济大学 | Thermosetting cyanate/bismaleimide resin composition |
| CN105038223A (en) * | 2015-06-02 | 2015-11-11 | 长春长光宇航复合材料有限公司 | Cyanate resin for hot-melt prepregs and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| LIANG GZ等: "Effect of the Epoxy Molecular Weight on the Properties of a Cyanate Ester/Epoxy Resin System", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111732929A (en) * | 2020-07-07 | 2020-10-02 | 遂宁立讯精密工业有限公司 | Cyanate ester adhesive with low curing temperature and high thermal stability and preparation method thereof |
| CN111732929B (en) * | 2020-07-07 | 2022-04-12 | 遂宁立讯精密工业有限公司 | Cyanate ester adhesive with low curing temperature and high thermal stability and preparation method thereof |
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Application publication date: 20200403 |