WO2015096141A1 - Composition de résine époxyde thermodurcissable et ses applications - Google Patents
Composition de résine époxyde thermodurcissable et ses applications Download PDFInfo
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- WO2015096141A1 WO2015096141A1 PCT/CN2013/090721 CN2013090721W WO2015096141A1 WO 2015096141 A1 WO2015096141 A1 WO 2015096141A1 CN 2013090721 W CN2013090721 W CN 2013090721W WO 2015096141 A1 WO2015096141 A1 WO 2015096141A1
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- Prior art keywords
- epoxy resin
- substituted
- weight
- resin composition
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- Prior art date
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/092—Polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
- C08L85/02—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers containing phosphorus
Definitions
- the present invention relates to a thermosetting epoxy resin composition, and more particularly to a halogen-free epoxy resin composition and a prepreg, a copper-clad laminate, and a high-frequency circuit substrate produced using the same.
- FR-4 materials mostly use dicyandiamide as a curing agent.
- This kind of curing agent has good process operability due to its tertiary amine. However, due to its weak carbon-nitrogen bond, it is easily cracked at high temperature, resulting in curing. The thermal decomposition temperature of the material is low and cannot meet the heat resistance requirements of the lead-free process.
- phenolic resins have been used as curing agents for epoxy resins in the industry. Phenolic resins have a high-density benzene ring heat-resistant structure, so after curing with epoxy resin The heat resistance of the system is very excellent, but at the same time, the dielectric properties of the cured product tend to deteriorate.
- thermosetting epoxy resin composition capable of providing excellent dielectric properties, moist heat resistance, high T g , and low water absorption required for a copper clad laminate. Rate, and achieve halogen-free flame retardant, reaching UL 94 V-0.
- thermosetting epoxy resin composition comprising:
- the present invention employs a polyphosphonate or/and a phosphonate-carbonate copolymer as a flame retardant, and has the advantages of large molecular weight, low water absorption, and good heat resistance.
- polyphosphonate structural formula is as follows:
- Ar is an aryl group
- the -O-Ar-O- is selected from the group consisting of a resorcinol reactive group, a hydroquinone reactive group, a bisphenol A reactive group, a bisphenol F reactive group, 4, 4 '-Diphenol, phenolphthalein reactive group, 4,4'-thiodiphenol reactive group, 4,4,-sulfonyl diphenol reactive group or 3,3,5-trimethylcyclohexyl diphenol Any one;
- X is a substituted or unsubstituted linear fluorenyl group of C1 to C20, a substituted or unsubstituted branched fluorenyl group of C1 to C20, a substituted or unsubstituted linear olefin group of C2 to C20, C2 a substituted or unsubstituted branched olefin group of ⁇ C20, a substituted or unsubstituted linear fluorenylene group of C2 to
- the structural formula of the phosphonate-carbonate copolymer is as follows:
- Ar Ar 2 and Ar 3 are each independently selected from aryl, -0-Ar 3 -0- active group is selected from resorcinol, hydroquinone reactive groups, active groups of bisphenol A, Bisphenol F reactive group, 4,4'-diphenol, phenolphthalein reactive group, 4,4,-thiodiphenol reactive group, 4,4,-sulfonyl diphenol reactive group or 3,3, Any one of 5-trimethylcyclohexyl diphenol;
- X 1 and X 2 are each independently a C1 to C20 substituted or unsubstituted linear fluorenyl group, a C1 to C20 substituted or unsubstituted branched hydrazine; Substituted, C2-C20 substituted or unsubstituted linear olefin group, C2 ⁇ C20 substituted or unsubstituted branched olefin group, C2 ⁇ C20 substituted or unsubstituted linear fluorenylene group, C2 ⁇ C20 substitution Or
- An aryl group means any functional group or substituent derived from an aromatic ring, and exemplary aromatic rings are toluene, ethylbenzene, n-propylbenzene, cumene, styrene, phenol, acetophenone, anisole, phenylethyl ether, Benzyl alcohol, benzaldehyde, benzoyl chloride, benzoic acid, benzonitrile, nitrobenzene, nitrosobenzene, aniline, fluorobenzene, chlorobenzene, Bromobenzene, iodobenzene, benzenesulfonic acid, diphenyl ketone, diphenylethylenedione, phenylacetic acid, mandelic acid, cinnamic acid, acetanilide, phenethylamine, azobenzene, diazonium chloride, Benzoyl peroxide, benzyl chloride,
- the polyphosphonate or / and phosphonate-carbonate copolymer is selected from
- R 3 , R 4 are each independently selected from a substituted or unsubstituted aliphatic or aromatic hydrocarbon group, preferably from an unsubstituted aliphatic or aromatic hydrocarbon group; 13 ⁇ 4 is an arbitrary integer from 1 to 100, n 3 , n 4 And n 5 each alone The standing position is an arbitrary integer of 1 to 75, and P1 is an arbitrary integer of 2 to 50.
- said! ! ! with! ⁇ Each is independently an arbitrary integer from 5 to 100, preferably! ! ! with! ⁇ Each independently is an arbitrary integer of 10 to 100.
- n 2 , n 3 , n 4 and n 5 are each independently an arbitrary integer from 5 to 75, and preferably, n 2 , n 3 , n 4 and n 5 are each independently from 10 to 75. Integer.
- the p and P1 are each independently an arbitrary integer of 5 to 50, and preferably p and P1 are each independently an arbitrary integer of 10 to 50.
- the 111 and mi are each independently, for example, 2, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90 or 95.
- n 2 , n 3 , n 4 and n 5 are each independently, for example, 2, 5, 8, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70 or 72.
- the and Pi are each independently, for example, 3, 5, 10, 14, 18, 22, 26, 30, 34, 38, 42, 45 or 48.
- the polyphosphonate or phosphonate-carbonate copolymer has a weight average molecular weight of from 1,000 to 60,000, preferably from 1,500 to 40,000, more preferably from 2,000 to 10,000.
- the weight average molecular weight is less than 1000, after adding to the cured resin, the heat resistance of the cured product is lowered, such as a decrease in glass transition temperature; but when the weight average molecular weight is more than 60,000, the polyphosphonate or phosphonic acid
- the solubility of the ester-carbonate copolymer in an organic solvent is too poor to obtain a good and uniform resin glue, so that it is difficult to meet the process requirements of the copper clad laminate.
- the epoxy resin is selected from the group consisting of epoxy resins having the following structure:
- X 2 and X 3 are each independently selected from or one of -5 to 5, and R 3 is selected from a hydrogen atom, a C1-C5 substituted or unsubstituted linear fluorenyl group or a C1-C5 substituted or unsubstituted branched fluorenyl group. Any of them;
- Yi, Y 2 are each independently selected from a single bond, -CH:
- a is any integer from 1 to 10, selected from a hydrogen atom, a C1-C5 substituted or unsubstituted linear fluorenyl group or a C1-C5 substituted or unsubstituted branched fluorenyl group, a decyloxy group.
- the epoxy resin is selected from any one of the epoxy resins having the following structure or a mixture of at least two:
- 1 is an arbitrary integer of 1 to 10
- R 5 is selected from a hydrogen atom, a substituted or unsubstituted C1-C5 linear fluorenyl group or a substituted or unsubstituted C1-C5 branched fluorenyl group;
- a 2 is any integer from 1 to 10, such as 2, 3, 4, 5, 6, 7, 8, or 9;
- a 4 is any integer from 1 to 10, such as 2, 3, 4, 5, 6, 7, 8, or 9;
- a 5 is any integer from 1 to 10, such as 2, 3, 4, 5, 6, 7, 8, or 9, and R 6 is selected from a hydrogen atom, a C1-C5 substituted or unsubstituted linear fluorenyl group or Any one of C1-C5 substituted or unsubstituted branched fluorenyl groups; R 7 is selected from a hydrogen atom, a C1-C5 substituted or unsubstituted linear fluorenyl group or a C1-C5 substituted or unsubstituted branched fluorenyl group. Any one of methoxy groups.
- the phenolic compound, the aromatic dicarboxylic acid or the acidic compound and the monohydroxy compound are obtained by reacting, wherein A and B are independently selected from a phenolic group, L is an alicyclic group, and f is an arbitrary integer of 1 to 5.
- the active ester curing agent mainly functions to cure the epoxy resin. Since the epoxy resin does not have secondary hydroxyl groups after curing, the cured product has substantially no hydroxyl polar groups and has good dielectric properties. Low water absorption and good resistance to heat and humidity.
- the phenolic compound is selected from any one or a mixture of at least two phenolic compounds having the following structure:
- f is an arbitrary integer from 1 to 5;
- the aromatic dicarboxylic acid is selected from any one of aromatic dicarboxylic acids having the following structure or a mixture of at least two:
- ⁇ is selected from a substituted or unsubstituted linear alkylene group of C1 to C5 or a substituted or unsubstituted C1 ⁇ C5
- 0.05 ⁇ 0.75mol such as 0.1 mol, 0.15 mol, 0.2 mol, 0.25 mol, 0.3 mol, 0.35 mol, 0.4 mol, 0.45 mol, 0.5 mol, 0.55 mol, 0.6 mol,
- the amount of the monohydroxy compound is 0.25 ⁇ 0.95 mol, for example 0.3 mo 0.35 mol,
- active ester curing agent has the following structural formula:
- X 4 and X 5 are independently selected from a benzene ring or a naphthalene ring, j is 0 or 1, k is 0 or 1, and n 6 represents an average repeating unit of 0.25 to 2.5.
- the polyphosphonate or/and the phosphonate-carbonate copolymer is 10 to 100 parts by weight, such as 15 parts by weight based on 100 parts by weight of the total of the components (A) and (B).
- the polymer or copolymer contained in the phosphonate in the present invention is not particularly limited as long as it can satisfy the UL 94 V-0 of the fixed product.
- the amount of the polymer or copolymer contained in the phosphonate is given by component (A), component (B) and component.
- the total amount of (C) is from 5 to 30% by weight, preferably from 8 to 25% by weight, more preferably from 15 to 25% by weight.
- the amount of the active ester curing agent to be added is calculated according to the epoxy equivalent and the active ester equivalent ratio, and the equivalent ratio is 0.85 to 1.2, for example, 0.88, 0.92, 0.96, 1, 1.04, 1.08, 1.12 or 1.16, preferably equivalent.
- the ratio is 0.9 to 1.1, and the most preferable equivalent ratio is 0.95 to 1.05.
- thermosetting epoxy resin composition of the present invention further comprises a component (D) filler, and the filler to be added as needed is not particularly limited, and the filler is selected from the group consisting of inorganic fillers and/or organic fillers, preferably.
- the inorganic filler is further preferably a surface-treated inorganic filler, most preferably a surface-treated silica.
- the surface treated surface treatment agent is selected from the group consisting of a silicon germanium coupling agent, a silicone oligomer or a titanate coupling Any one or a mixture of at least two;
- the silicon germanium coupling agent is selected from the group consisting of vinyl trimethoxysilane, vinyl triethoxysilane,
- the surface treatment agent is used in an amount of 0.1 to 5.0 parts by weight, preferably 0.5 to 3.0 parts by weight, and still more preferably 0.75 to 2.0 parts by weight, based on 100 parts by weight of the inorganic filler.
- the inorganic filler is selected from any one of a non-metal oxide, a metal nitride, a non-metal nitride, an inorganic hydrate, an inorganic salt, a metal hydrate or an inorganic phosphorus or a mixture of at least two, preferably a crystalline type of dioxide Silicon, fused silica, spherical silica, hollow silica, glass powder, aluminum nitride, boron nitride, silicon carbide, aluminum hydroxide, titanium dioxide, barium titanate, barium titanate, aluminum oxide, barium sulfate Any one or a mixture of at least two of talc, calcium silicate, calcium carbonate or mica.
- the mixture is, for example, a mixture of crystalline silica and fused silica, a mixture of spherical silica and hollow silica, a mixture of glass powder and aluminum nitride, a mixture of boron nitride and silicon carbide, aluminum hydroxide. a mixture with titanium dioxide, a mixture of barium titanate, barium titanate and alumina, a mixture of barium sulfate, talc, calcium silicate, calcium carbonate and mica.
- the organic filler is selected from any one or a mixture of at least two of polytetrafluoroethylene powder, polyphenylene sulfide, organic phosphorus salt compound or polyethersulfone powder.
- the mixture such as polytetrafluoroethylene powder and A mixture of polyphenylene sulfide, a mixture of an organic phosphorus salt compound and a polyethersulfone powder.
- the shape, particle diameter, and the like of the filler are also not particularly limited, and it is preferable that the filler has a median diameter of 0.01 to 50 ⁇ m, for example, 1 ⁇ m, 3 ⁇ m, 7 ⁇ m, 12 ⁇ m, 25 ⁇ m, 28 ⁇ m, 32 ⁇ m, 37 ⁇ m, 43 ⁇ m, 47 ⁇ m 49 ⁇ , preferably 0.01 to 20 ⁇ m, further preferably 0.1 to 10 ⁇ m, and the inorganic filler having such a particle diameter range is more easily dispersed in the resin liquid.
- the amount of the component (D) filler to be added is also not particularly limited, and the total weight of the component ( ⁇ ), the component ( ⁇ ), and the component (C) is 100 parts by weight, the component ( ⁇ ).
- the filler is added in an amount of 5 to 1000 parts by weight, for example, 10 parts by weight, 80 parts by weight, 120 parts by weight, 230 parts by weight, 350 parts by weight, 450 parts by weight, 520 parts by weight, 680 parts by weight, 740 parts by weight, 860 parts by weight
- the parts by weight, 970 parts by weight are preferably 5 to 300 parts by weight, more preferably 5 to 200 parts by weight, particularly preferably 15 to 100 parts by weight.
- the thermosetting epoxy resin composition of the present invention further contains a component ( ⁇ ) curing accelerator, and the curing accelerator is not particularly limited as long as it can catalyze the reaction of the epoxy functional group and lower the reaction temperature of the curing system.
- the curing accelerator is not particularly limited as long as it can catalyze the reaction of the epoxy functional group and lower the reaction temperature of the curing system.
- it is preferably an imidazole compound and a derivative compound thereof, a piperidine compound, a Lewis acid or a triphenylphosphine, or a mixture of at least two.
- the imidazole compound may, for example, be any one of 2-methylimidazole, 2-phenylimidazole or 2-ethyl-4-methylimidazole or a mixture of at least two, and the piperidine compound may be enumerated.
- 2,3-diaminopiperidine 2,5-diaminopiperidine 2,6-diaminopiperidine, 2,5-diamino, 2-amino-3-methylpiperidine, 2-amino-4 Any one or a mixture of at least two of -4 methylpiperidine, 2-amino-3-nitropiperidine, 2-amino-5-nitropiperidine or 4-dimethylaminopiperidine.
- the component ( ⁇ ) curing accelerator is added in an amount of 0.01 to 1 part by weight, for example, 0.07 by weight based on 100 parts by weight of the total weight of the component ( ⁇ ), the component ( ⁇ ), and the component (C).
- the term "comprising" as used in the present invention means that it may include other components in addition to the components, and these other components impart different characteristics to the resin composition.
- the "include” of the present invention may be replaced by a closed “for” or "consisting of”.
- thermosetting epoxy resin composition of the present invention may be added with a thermosetting resin, and specific examples thereof include a polyphenylene ether resin, a cyanate resin, a phenol resin, a polyurethane resin, a melamine resin, and the like, and may be added.
- a curing agent or curing agent accelerator for these thermosetting resins include a polyphenylene ether resin, a cyanate resin, a phenol resin, a polyurethane resin, a melamine resin, and the like.
- thermosetting epoxy resin composition may further contain various additives, and specific examples thereof include an antioxidant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment, a colorant, a lubricant, and the like. These thermosetting resins and various additives may be used singly or in combination of two or more kinds.
- the component (A), the component (B), the component (C), a curing accelerator, a filler, and various kinds may be blended, stirred, and mixed by a known method.
- the resin gel can be obtained by dissolving or dispersing the thermosetting epoxy resin composition as described above in a solvent.
- the solvent in the present invention is not particularly limited, and specific examples thereof include alcohols such as methanol, ethanol, and butanol, ethyl cellosolve, butyl cellosolve, ethylene glycol-methyl ether, carbitol, and butyl.
- Ethers such as carbitol, ketones such as acetone, butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, aromatic hydrocarbons such as toluene, xylene, and mesitylene, ethoxylate
- An ester such as ethyl acetate or ethyl acetate; a nitrogen-containing solvent such as hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimethylacetamide or hydrazine-methyl-2-pyrrolidone.
- solvents may be used singly or in combination of two or more.
- aromatic hydrocarbon solvents such as toluene, xylene, and mesitylene, and acetone, butanone, methyl ethyl ketone, and methyl group.
- a ketone flux such as butyl ketone or cyclohexanone is used in combination.
- the amount of the solvent used can be based on the person skilled in the art. The experience is chosen to bring the resulting resin glue to a viscosity suitable for use.
- An emulsifier may be added during the process of dissolving or dispersing the resin composition as described above in a solvent. By dispersing by an emulsifier, the powder filler or the like can be uniformly dispersed in the glue.
- Another object of the present invention is to provide a prepreg comprising a reinforcing material and a thermosetting epoxy resin composition as described above adhered to the reinforcing material by impregnation and drying.
- the reinforcing material is not particularly limited and may be an organic fiber, an inorganic fiber woven fabric or a non-woven fabric, and the organic fiber may preferably be aramid nonwoven, and the inorganic fiber woven fabric may be E-glass, D-glass. , S-glass, T-glass, NE-glass and quartz cloth.
- the thickness of the reinforcing material is not particularly limited.
- the thickness of the braided fabric or nonwoven fabric is preferably 0.01 to 0.2 mm, and is preferably subjected to fiber opening treatment and silicon.
- the surface treatment of the ruthenium coupling agent in order to provide good water resistance and heat resistance, the silicon germanium coupling agent is preferably an epoxy silicon germanium coupling agent, an aminosilicone coupling agent or a vinyl silicon germanium coupling agent. Any one or a mixture of at least two.
- the prepreg is obtained by drying the prepreg impregnated with the thermosetting epoxy resin composition at 100 to 200 ° C for 2 to 10 minutes.
- a third object of the present invention is to provide a laminate comprising at least one prepreg as described above.
- One or more prepregs as described above are stacked in a certain order, and the copper foil is respectively pressed on one side or both sides of the prepreg which are superposed on each other, and is solidified in a hot press.
- a copper clad laminate having a curing temperature of 150 to 250 ° C and a curing pressure of 25 to 60 kg/cm 2 .
- the prepreg, the laminate and the copper-clad laminate according to the invention have excellent dielectric properties, moisture and heat resistance, high glass transition temperature, lower water absorption, and halogen-free resistance. Burning, reaching UL 94 V-0.
- a fourth object of the present invention is to provide a high-frequency circuit substrate comprising at least one prepreg as described above, and a copper foil covering both sides of the laminated prepreg.
- thermosetting epoxy resin composition of the present invention adopts a specific molecular structure
- the epoxy resin has high functionality and the cured product has low low water absorption
- 2 the epoxy resin composition of the invention uses the active ester as a curing agent to fully exert the reaction of the active ester with the epoxy.
- a polar group which has excellent dielectric properties and good heat and humidity resistance.
- a polyphosphonate or/and a phosphonate-carbonate copolymer having a number average molecular weight of 1000 to 60,000 is used as a flame retardant without sacrificing the original
- the heat-resistant product has low heat resistance, low water absorption, and excellent dielectric properties, and achieves halogen-free flame retardancy, and the flame retardancy of the cured product reaches UL94 V-0 level; 3.
- the use of the above thermosetting epoxy resin combination of the present invention The prepreg and its copper-clad laminate have excellent dielectric properties, moisture and heat resistance, and have a flame retardancy of UL94 V-0. Concrete J ⁇ r
- the dielectric constant and dielectric loss factor, the glass transition temperature and the moist heat resistance were measured, and the details and description are further given in the following examples.
- the above-mentioned glue was impregnated with a glass cloth (model 2116, thickness 0.08 mm), and controlled to a suitable thickness, and then the solvent was removed by drying to obtain a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- Example 2 Take a container, add 100 parts by weight of naphthol novolac epoxy resin NC-7000L (Nippon Chemical Co., Ltd., EEW is 232 g/eq), and then add 95 parts by weight of active ester curing agent HPC-8000-65T (Japan DIC, solid content of 65%), evenly stirred, and then added flame retardant phosphonate oligomer compound OL5000 (FRX Polymers, phosphorus content of 10.8%) 65 parts by weight, and then added 0.075 parts by weight of curing accelerator DMAP, and Solvent toluene, continue to stir and form a glue.
- NC-7000L Natural Chemical Co., Ltd., EEW is 232 g/eq
- the above-mentioned glue was impregnated with a glass cloth (model 2116, thickness 0.08 mm), and controlled to a suitable thickness, and then the solvent was removed by drying to obtain a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- the above-mentioned glue was impregnated with a glass cloth (model 2116, thickness 0.08 mm), and controlled to a suitable thickness, and then the solvent was removed by drying to obtain a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- the above-mentioned glue was impregnated with a glass cloth (model 2116, thickness 0.08 mm), and controlled to a suitable thickness, and then the solvent was removed by drying to obtain a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- the above-mentioned glue was impregnated with a glass cloth (model 2116, thickness 0.08 mm), and controlled to a suitable thickness, and then the solvent was removed by drying to obtain a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- a glass fiber cloth model 2116, thickness 0.08 mmy, and control to a suitable thickness
- bake The solvent is removed by dry removal to prepare a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- the above-mentioned glue was impregnated with a glass cloth (model 2116, thickness 0.08 mm), and controlled to a suitable thickness, and then the solvent was removed by drying to obtain a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- the above-mentioned glue was impregnated with a glass cloth (model 2116, thickness 0.08 mm), and controlled to a suitable thickness, and then the solvent was removed by drying to obtain a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- Comparative example 1 Comparative example 1
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- Prepreg is prepared by dipping the above-mentioned glue with a glass fiber cloth (model 2116, thickness 0.08 mmy, and controlling to a suitable thickness, and then drying and removing the solvent.
- the prepregs obtained by using several sheets are superposed on each other, A copper foil is pressed on both sides thereof and cured in a hot press to obtain a copper-clad laminate having a curing temperature of 150-250 ° C and a curing pressure of 25-60 kg/cm 2 , and the curing time is 90min.
- the above-mentioned glue was impregnated with a glass cloth (model 2116, thickness 0.08 mm), and controlled to a suitable thickness, and then the solvent was removed by drying to obtain a prepreg.
- the prepreg obtained by using a plurality of sheets is superposed on each other, and a copper foil is pressed on both sides thereof to be cured in a hot press to obtain a copper clad laminate having a curing temperature of 150-250 ° C.
- the curing pressure is 25-60 kg/cm 2 and the curing time is 90 min.
- Table 1 Physical property data of each of the examples and comparative examples
- V-2 V-0 V-0 V-0 The test method for V-2 V-0 V-0 V-0 is as follows:
- Glass transition temperature (Tg) Measured according to the DMA test method specified in IPC-TM-650 2.4.24 using the DMA test.
- Comparative Example 1 does not contain a flame retardant, and an active ester curing agent can achieve good heat resistance and dielectric properties, but does not reach the flame retardant V-0 level, and is used from Comparative Example 3
- Conventional phenolic resin as a curing agent due to the secondary hydroxyl group generated after curing with epoxy, has poor dielectric properties, especially high dielectric loss tangent;
- Comparative Example 4 uses existing phosphate as a flame retardant, although V- can be achieved. 0 flame retardant requirements, but due to the plasticity of the phosphate ester, the glass transition temperature of the curing system is severely lowered.
- the present invention adds a phosphonate having a number average molecular weight of 1000 to 60000. Or / and phosphonate-carbonate copolymer as a flame retardant, without sacrificing the heat resistance of the original cured product, low water absorption, excellent dielectric properties, achieving halogen-free flame retardant, curing product resistance Flammability reaches UL94 V-0;
- the copper-clad laminate of the present invention has superior dielectric properties, high glass transition temperature, and high heat and humidity resistance as compared with a general copper foil substrate, and is suitable for use in a high frequency field.
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Abstract
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Cited By (4)
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CN108117634A (zh) * | 2016-11-30 | 2018-06-05 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108117633A (zh) * | 2016-11-30 | 2018-06-05 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108117632A (zh) * | 2016-11-30 | 2018-06-05 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
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CN108117634A (zh) * | 2016-11-30 | 2018-06-05 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108117633A (zh) * | 2016-11-30 | 2018-06-05 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108117632A (zh) * | 2016-11-30 | 2018-06-05 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
WO2018098908A1 (fr) * | 2016-11-30 | 2018-06-07 | 广东生益科技股份有限公司 | Composition de résine thermodurcissable |
CN108117632B (zh) * | 2016-11-30 | 2019-08-23 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108117634B (zh) * | 2016-11-30 | 2019-08-27 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108117633B (zh) * | 2016-11-30 | 2019-08-27 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108164684A (zh) * | 2016-12-07 | 2018-06-15 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
CN108164684B (zh) * | 2016-12-07 | 2019-08-27 | 广东生益科技股份有限公司 | 一种热固性树脂组合物 |
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