WO2006021313A1 - Polymermaterial zur herstellung von laminaten sowie laminat für die leiterplattenindustrie - Google Patents
Polymermaterial zur herstellung von laminaten sowie laminat für die leiterplattenindustrie Download PDFInfo
- Publication number
- WO2006021313A1 WO2006021313A1 PCT/EP2005/008459 EP2005008459W WO2006021313A1 WO 2006021313 A1 WO2006021313 A1 WO 2006021313A1 EP 2005008459 W EP2005008459 W EP 2005008459W WO 2006021313 A1 WO2006021313 A1 WO 2006021313A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer material
- resin
- mixture
- resins
- polymer
- Prior art date
Links
Classifications
-
- 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
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- 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
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/065—Preparatory processes
- C08G73/0655—Preparatory processes from polycyanurates
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
-
- 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
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
Definitions
- the present invention relates to polymer material, in particular a polymer mixture, of a mixture of hydrocarbon resin with cyanate ester and optionally epoxy resin as polymer material for the production of laminates for the printed circuit board industry, preferably for the production of electrical laminates with low dielectric losses.
- the invention further relates to a laminate for the production of printed circuit boards of this polymer material.
- the laminates used in the electrical industry are plastic sheets, which, in simple terms, consist of fabric layers which, in turn, have been coated, for example, with phenolic or epoxy resins.
- the materials used for laminate production can be divided into three material classes:
- the resins used in the production of laminates are phenolic resins, polyester resins, epoxy resins, bismaleimide / triazine resins, cyanate resins, polyimide resins, but also teflon (polytetrafluoroethylene).
- phenolic resins polyester resins
- epoxy resins bismaleimide / triazine resins
- cyanate resins polyimide resins
- polyimide resins but also teflon (polytetrafluoroethylene).
- teflon polytetrafluoroethylene
- BEST ⁇ TäGUNGSKOPlE this includes paper, nonwovens and woven fabrics made of glass or aramid, PTFE fabric and PTFE film.
- copper foils made of electrodeposited copper or rolled copper are used for the production of laminates.
- laminate materials with improved dielectric properties are needed, i. such materials have a low dielectric loss factor tan ⁇ and a low dielectric constant DK.
- Laminates are suitable.
- hydrocarbon resins are thermoplastic polymers which have a mean molecular weight below 2000 and soften over a wide temperature range. Depending on the provenance of
- Hydrocarbon resins are usually distinguished between resins of petroleum, resins of coal tar and resins of terpene resins.
- the petroleum or petroleum resins are the most important group of hydrocarbon resins.
- coal tar resins reference should be made to coumarone-indene resins (also called indene coumarone resins), which are the main representatives of this group are and are the oldest synthetic thermoplastics ever to have found a variety of engineering applications.
- the range of hydrocarbon resins ranges from liquids at normal temperature to brittle hard solids, where the color of the resins can vary from almost colorless to dark brown. Due to the property profile of these resins, they may i.a. as binders, tackifiers, enhancers, extenders, film formers and dispersants in a variety of applications, especially in adhesives, rubbers and paints, etc. are used.
- hydrocarbon resins have good insulating properties since the values of the dielectric constants are in the range of about 2.3 to 2.8.
- hydrocarbon resins are in aromatic and aliphatic solvents, higher ketones, esters, ethers and halogenated
- hydrocarbon resins are also compatible with a variety of materials, namely, drying oils, plasticizers, styrenes, polyethylene waxes and rubbers, so that such hydrocarbon resins could also find use as additives for reactive polymers.
- hydrocarbon resins are not compatible with castor oils, cellulose ethers and esters, as well as epoxy resins and ketone resins (see Ulimann's Encyclopadie der ischen Chemie, 4th Edition, Vol. 12, 539, 540 right column.
- the polymer materials in particular polymer mixtures as cyanate ester resins, may comprise at least one compound of the general formula I
- R is a mononuclear or polynuclear aromatic or alkylaromatic substituted or unsubstituted radical and n is a number greater than 1.
- X a divalent organic radical, in particular a substituted or unsubstituted linear, cyclic or branched alkyl or benzyl radical having 1 to
- R inert organic radical, in particular an alkyl, halogen, an ether or
- cyanate ester resins may also contain triazines.
- EP 0 794 979 B1 in which such polyfunctional phenolocyanate / phenoltriazine copolymers have been described, to which reference is hereby expressly made.
- Triazines can be obtained from the company Lonza Ltd., Basel, Switzerland under the product name Primaset®. Products which can be used according to the invention are, for example, Primaset® PT-15, Primaset® PT-30, Primaset® PT-3OS, Primaset® PT-60, Primaset® PT-60S, Primaset® BA-230S, where the cyanate ester resin of the product Primaset® PT- 60 for the inventive
- Polymer materials is particularly preferred.
- Polymer / polymer blends that are not in thermodynamic equilibrium, but which are e.g. behave in terms of mechanical properties as if they were.
- Exemplary here are aliphatic and / or aromatic hydrocarbon resins which have been modified by copolymerization with phenol and / or styrene.
- thermoplastic hydrocarbon resins based on petro- and carbostämmiger raw materials, which can be obtained from the company RÜTGERS CHEMICALS AG, Duisburg, Germany under the name NOVARES®, preferably aromatic hydrocarbon resins, aliphatic modified, aromatic hydrocarbon resins, phenol-modified aromatic hydrocarbon resins and indene -Cumaron resins.
- phenol-modified petroleum-derived hydrocarbon resins in particular copolymers of unsaturated C9 / C10 aromatic hydrocarbon resins with phenol, which have a softening point (ring & ball) ASTM D3465 95 to 125 [ 0 C] and a color (Gardner scale) [50 % in toluene] ISO 4630 5 to 9 are marked and those of the company
- RÜTGERS CHEMICALS AG are available under the product name NOVARES®.
- the polymer materials according to the invention mixtures of at least one compatible with cyanate esters hydrocarbon resin, namely at least one phenol-modified petroleum hydrocarbon resin, in particular at least one copolymer of an unsaturated, aromatic C9- / C10-hydrocarbon resin with phenol, which has a softening point (ring & ball) ASTM D3465 95 to 125 [ 0 C] and a color (Gardner scale) [50%]. in toluene] ISO 4630 5 to 9 and under the name
- NOVARES® TA 100 is available, with at least one liquid hydrocarbon resin, in particular a styrenated phenolic resin, which by a viscosity at 25 ° C from 400 to 1400 [mPas], an OH content of 7.0 to 7.6 [%] and a Color (Gardener scale) undiluted ISO 4630 of max. 6 is marked.
- liquid styrenated phenolic resins are also available from RÜTGERS CHEMICALS AG under the product name NOVARES® LS 500.
- the polymer materials according to the invention must be suitable as polymer materials for the production of laminates for the printed circuit board industry, preferably for the production of electrical laminates with low dielectric losses, it has been found that particularly good results can be achieved for this application, if the polymer materials according to the invention Hydrocarbon resins, a combination of a phenol-modified petroleum-derived hydrocarbon resin, in particular one
- a copolymer of an unsaturated, aromatic C9 / C10 hydrocarbon resin with phenol is, preferably a NOVARES® TA 100 hydrocarbon resin, and a NOVARES® LS 500 styrenated phenolic resin.
- the weight ratio between the phenol-modified petroleum-derived hydrocarbon resin and the liquid hydrocarbon resin, preferably a styrenated phenolic resin is in the range from 0.3 to 1.7 parts by weight to 1.7 to 0.3 parts by weight.
- a weight ratio ranging from 0.75 to 1.25 to 1.25 to 0.75
- the polymer materials according to the invention may optionally comprise at least one epoxy resin.
- all epoxide compounds which contain more than one epoxide group, ie which are difunctional or polyfunctional, can be used as epoxide compounds.
- difunctional epoxide compounds are preferred.
- the polymer materials according to the invention may in particular comprise polyglycidyl ethers of novolaks.
- polymer materials according to the invention may contain further additives, such as e.g. Hardener, solvent, further compatible with the polymeric materials additional resins, accelerators or retarders.
- further additives such as e.g. Hardener, solvent, further compatible with the polymeric materials additional resins, accelerators or retarders.
- polymer materials according to the invention are outstandingly suitable as polymer materials for the production of laminates for the circuit board industry, preferably for the production of electrical laminates with low dielectric losses.
- hydrolysis-resistant laminates with low dielectric constants and dielectric loss factors can be produced therefrom, or else storage-stable, relatively moist, insensitive prepregs can be produced therefrom.
- the boiling point is set to 110 0 C at the end.
- 64 kg of phenol-modified, petroleum-derived hydrocarbon resin copolymer of unsaturated aromatic C 9 / C 10 hydrocarbon resins with phenol eg that available under the trade name Novares® TA 100 from Rütgers Chemicals AG, Duisburg
- 64 kg of styrene / phenol-modified petro-carbohedral hydrocarbon resin eg that available under the trade name Novares LS 500 from Rütgers Chemicals AG, Duisburg
- 680 kg of cyanate ester are added and dissolved.
- the resin is cooled to room temperature.
- Support material is a type 7628 glass cloth having a gross weight of about 203 g / m 2 .
- the fabric is conveyed at a rate of 0.8-1.4 m / min through the resin bath with impregnating varnish and through squeezing
- the cyanate ester / hydrocarbon resin / epoxy resin blend is available under the trade name Bakelite® EPS 05353 from Bakelite AG, Iserlohn-Lethmate.
- the modifier is available under the trade name Bakelite® EPM 05352 and the catalyst under the trade name Bakelite® EPC 05126 from Bakelite AG, Iserlohn-Lethmate.
- the impregnated fabric is dried by a multi-stage vertical dryer at 160 0 C air temperature and 188 ° C / 189 ° C radiant heater temperature to the required characteristics of the prepreg out.
- Prepreg rape content ⁇ 1, 0%
- the laminate is made up of 8 layers of prepreg and 2 layers of 35 ⁇ m copper foil, one of which forms the topmost layer and the other the bottommost laminate layer.
- the curing takes place at a rate 2-4 K / min, a lamination temperature of at least 200 to 220 0 C for 1 hour and an effective pressing pressure 10-50 bar.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004041129A DE102004041129A1 (de) | 2004-08-24 | 2004-08-24 | Polymermaterial zur Herstellung von Laminaten sowie Laminat für die Leiterplattenindustrie |
DE102004041129.8 | 2004-08-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006021313A1 true WO2006021313A1 (de) | 2006-03-02 |
Family
ID=34981467
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2005/008459 WO2006021313A1 (de) | 2004-08-24 | 2005-08-04 | Polymermaterial zur herstellung von laminaten sowie laminat für die leiterplattenindustrie |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE102004041129A1 (fi) |
TW (1) | TW200616790A (fi) |
WO (1) | WO2006021313A1 (fi) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009003132A1 (de) * | 2009-05-15 | 2010-11-18 | Robert Bosch Gmbh | Kunststoffformmasse sowie Verfahren zu deren Herstellung |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4533727A (en) * | 1983-04-06 | 1985-08-06 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a curable resin from cyanate ester compound and unsaturated 1,2-epoxy compound |
EP0290860A2 (en) * | 1987-04-27 | 1988-11-17 | Mitsubishi Gas Chemical Company, Inc. | Thermosetting resin composition |
US6372861B1 (en) * | 1999-02-09 | 2002-04-16 | Bakelite A.G. | Cyanate resin, polyepoxide and metal complex curing agent |
US20020197479A1 (en) * | 2001-05-15 | 2002-12-26 | Samsung Electro-Mechanics Co., Ltd. | Cyanate ester-containing insulating composition, insulating film made therefrom and multilayer printed circuit board having the film |
-
2004
- 2004-08-24 DE DE102004041129A patent/DE102004041129A1/de not_active Withdrawn
-
2005
- 2005-08-04 WO PCT/EP2005/008459 patent/WO2006021313A1/de active Application Filing
- 2005-08-08 TW TW094126821A patent/TW200616790A/zh unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4533727A (en) * | 1983-04-06 | 1985-08-06 | Mitsubishi Gas Chemical Company, Inc. | Process for producing a curable resin from cyanate ester compound and unsaturated 1,2-epoxy compound |
EP0290860A2 (en) * | 1987-04-27 | 1988-11-17 | Mitsubishi Gas Chemical Company, Inc. | Thermosetting resin composition |
US6372861B1 (en) * | 1999-02-09 | 2002-04-16 | Bakelite A.G. | Cyanate resin, polyepoxide and metal complex curing agent |
US20020197479A1 (en) * | 2001-05-15 | 2002-12-26 | Samsung Electro-Mechanics Co., Ltd. | Cyanate ester-containing insulating composition, insulating film made therefrom and multilayer printed circuit board having the film |
Also Published As
Publication number | Publication date |
---|---|
DE102004041129A1 (de) | 2006-03-02 |
TW200616790A (en) | 2006-06-01 |
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