EP1583788A1 - Phosphorus-modified epoxy resin - Google Patents
Phosphorus-modified epoxy resinInfo
- Publication number
- EP1583788A1 EP1583788A1 EP04700258A EP04700258A EP1583788A1 EP 1583788 A1 EP1583788 A1 EP 1583788A1 EP 04700258 A EP04700258 A EP 04700258A EP 04700258 A EP04700258 A EP 04700258A EP 1583788 A1 EP1583788 A1 EP 1583788A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- epoxy resin
- phosphorus
- modified epoxy
- polyepoxide
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Classifications
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
-
- 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
- C08G59/1405—Polycondensates modified by chemical after-treatment with inorganic compounds
- C08G59/1422—Polycondensates modified by chemical after-treatment with inorganic compounds containing phosphorus
-
- 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
- C08G59/1488—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing phosphorus
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/304—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing phosphorus
-
- 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
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/48—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor
- H01L23/488—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor consisting of soldered or bonded constructions
- H01L23/498—Leads, i.e. metallisations or lead-frames on insulating substrates, e.g. chip carriers
- H01L23/49866—Leads, i.e. metallisations or lead-frames on insulating substrates, e.g. chip carriers characterised by the materials
- H01L23/49894—Materials of the insulating layers or coatings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
-
- 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
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
Definitions
- the invention relates to a phosphorus-modified epoxy resin, a process for its production, a phosphorus-modified epoxy resin mixture and its use.
- thermosetting resins such as phenolic, polyester or epoxy resins.
- Epoxy resins with a flame-retardant effect which show good physical and electrical properties in the hardened state, are obtained by reacting polyepoxide compounds with polyphosphonic and / or polyphosphinic acid anhydrides, as is known from EP-A 794 205.
- polyepoxide compounds with polyphosphonic and / or polyphosphinic acid anhydrides, as is known from EP-A 794 205.
- organic phosphinic or phosphonous acid is also described in the literature (EP 1 046 661 AI) and the use of phosphinic or phosphonic anhydrides (WO 96/07684).
- the problem with phosphorus-modified epoxy resins is that although the flammability rating according to UL-94 V-0 is achieved, the moisture resistance of the laminates, which serve as the base material for the production of printed circuits, is no longer sufficient.
- the previously used phosphorus compounds also significantly lower the glass transition temperature of the laminates, so that the laminates are used required glass transition temperature> 150 ° C can no longer take place.
- the permanent temperature stability (T-260 test) of these laminates is also not guaranteed.
- the phosphorus-modified epoxy resins according to the invention can be prepared by simple process steps and these, in particular in combination with a hardener in the form of dicyandiamide, aromatic amines, phenol, cresol or bisphenol A novolaks and / or acid anhydrides in the cured state, are both flame-retardant are equipped, d. H. meet the flammability rating UL 94-V0, as well as have excellent moisture resistance. Furthermore, the epoxy resin systems according to the invention have an excellent long-term temperature resistance in the hardened state.
- the phosphorus-modified epoxy resin according to the invention is produced by reacting at least one polyepoxide with at least 2 epoxy groups with 5 to 50 parts by weight of polyphenylene ethylphosphonate, based on 100 parts by weight of the polyepoxide, with a molecular weight of 500 to 20,000 g / mol at a temperature of 80 ° C. to 150 ° C. , preferably 130 ° C to 140 ° C, and a time of 0.5 to 6 hours, the reaction being carried out essentially in the melt of the polyepoxide.
- the polyphenylene methylphosphonate with a molecular weight of 500 to 20,000 g / mol used has the general formula (m position shown):
- One or more polyepoxide (s) based on bisphenol A and / or bisphenol F, advancement resins based on bisphenol A and / or bisphenol F, o-cresol novolaks, bisphenol A novolaks and / or phenol can be used for the epoxy resin according to the invention -Novolacs can be used. They usually have an epoxy equivalent weight of 170 to 450 g. But it is also possible that, for. B. tri- or tetrafunctional epoxy resins such. B. N, N, N ', N'-tetraglycidyl-4,4'-diamino-diphenylmethane can be used.
- the preferred preparation of the phosphorus-modified epoxy resin according to the invention comprises at least the following step:
- Both the temperature control and the time for the production of the epoxy resin according to the invention is very important. If 150 ° C is exceeded, a gelling process begins, which is undesirable. Reactions at temperatures ⁇ 80 ° C lead to insufficient yields, which is also the case with a reaction time ⁇ 0.5 hours.
- reaction is carried out at 130 ° C to 140 ° C.
- a defined molecular weight of the phosphorus-modified epoxy resin is achieved through this reaction temperature range.
- reaction product can be dissolved by adding a solvent, in particular methoxypropanol, acetone and or methyl ethyl ketone.
- a solvent in particular methoxypropanol, acetone and or methyl ethyl ketone.
- a solvent mixture of methoxypropanol and acetone is preferred since the combination of a low-boiling and a higher-boiling component produces a desired optically uniform impregnation pattern in the production of laminates.
- the phosphorus-modified epoxy resin can be added in customary amounts, which leads to phosphorus-modified epoxy resin mixtures.
- at least one polyepoxide and / or hardener and / or fillers and or accelerator can be admixed as further constituents.
- these include other ingredients such as inorganic fillers or additional additives with flame retardant properties such as.
- Accelerators can be added in the form of, for example, metal complex compounds, tertiary amines or imidazoles.
- the phosphorus-modified epoxy resin in conventional amounts as hardener which serves to control the hardening reaction, is a hardener in the form of amines, polyamines, epoxy-amine adducts, phenolic resins, dicyandiamide, polyaminoamides, acid anhydrides, cyanguanidines and / or Friedel Crafts catalysts is used. After curing, a product is obtained which has a glass transition point> 150 ° C., reduced moisture absorption and good processability.
- the epoxy resin system according to the invention is preferably used for the production of laminates, namely both epoxy resin / paper and also epoxy resin / glass fiber l-e-L-uninates.
- the phosphorus-modified epoxy resin system according to the invention can also be used for
- Fiber composite materials or electrical casting resins are used.
- 100 parts by weight of an epoxidized novolak are mixed with 21 parts by weight of poly (m-phenylene methylphosphonate) and melted at 135 ° C. and homogenized. The mixture is left to react at this temperature for 1 h 25 min and 18.5 parts by weight of 1-methoxypropanol and methyl ethyl ketone are added with evaporative cooling.
- the result is a solution of a phosphorus-modified epoxy resin with a resin content of 76.1%, a viscosity at 25 ° C. of 2350 mPas and an epoxy equivalent weight of the solid resin of 234 g / equivalent.
- 100 parts by weight of an epoxidized novolak are mixed with 21 parts by weight of poly (m-phenylene methylphosphonate) and 37 parts by weight of 1-methoxypropanol and at 100 ° C. solved.
- the mixture is then heated to boiling point (130 ° C).
- the mixture is left to react for 2 hours, the temperature rising to 136 ° C.
- the result is a solution of a phosphorus-modified epoxy resin with a resin content of 76.6%, a viscosity at 25 ° C. of 4970 mPas and an epoxy equivalent weight of the solid resin of 244 g / equivalent.
- 100 parts by weight of an epoxidized novolak are mixed with 21 parts by weight of poly (m-phenylene methylphosphonate) and 18.5 parts by weight of 1-methoxypropanol and methyl ethyl ketone and dissolved at 80 ° C.
- the result is an epoxy resin solution with a resin content of 75.6%, a viscosity at 25 ° C. of 400 mPas and an epoxy equivalent weight of the solid resin of 216 g / equivalent.
- B times and glass transition temperatures were determined, it being evident that the highest glass transition temperature was achieved using the phosphorus-modified epoxy resin according to the invention. B times and glass transition temperatures were determined as follows: - B time:
- the reactivity of the uncured system was measured by the gel-time technique on a hot plate at 170 ° C. Low values mean a high reactivity of the system.
- Glass fabric type 7628 (Gividi) is impregnated with the resin solutions (composition Table 1), predried at 120 ° C. for 15 minutes and then cured at 180 ° C. for 2 hours.
- the glass transition temperature was measured by Differential Scanning Calorimetry (DSC) at a heating rate of 20 ° C / min.
- 100 parts by weight of an epoxidized novolak are in 33.4 parts by weight of methyl ethyl ketone solved.
- 30.0 parts by weight of a 75% strength solution of a phosphorus-containing ester anhydride are added dropwise to this solution at 50 ° C. in the course of one hour. The temperature is raised to 90 ° C. and the temperature is maintained at this temperature for 5 hours.
- Phenol novolaks (Bakelite® PHS 6000 IZ01) added and the mixture homogenized.
- the result is an epoxy resin hardener mixture with a resin content of 75%, a viscosity at 25 ° C. of 1160 mPas and an epoxy equivalent weight of the solid resin of 370 g / equivalent.
- a 25 mm wide and 100 mm long strip of copper foil is detached from the glass hard tissue over a length of 20 mm and pulled off vertically by means of a suitable device at a pull-off speed of 50 mm / min.
- the force F (N) is measured.
- a copper-clad laminate sample on both sides is exposed to a temperature of 260 ° C in the TMA (thermomechanical analysis). The time until delamination of the laminate is measured.
- Pressure Cooker Test The test was carried out according to the standard test method IPC-TM-650 2.6.16. On the scale from 1 to 5, 1 means big bubbles, measlings or surface erosion and 5 means no bubbles, measlings or surface erosion.
- Laminates have a surprisingly good temperature and moisture resistance for a phosphorus-modified epoxy resin system of flammability class V-0 and are therefore particularly suitable for the production of halogen-free printed circuit board base material.
- Prepreg gel time must be reduced very far in order to obtain laminates with sufficient thickness. It also has a higher water absorption and a lower one
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Resins (AREA)
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2003100462 DE10300462A1 (en) | 2003-01-07 | 2003-01-07 | Phosphorus modified epoxy resin |
DE10300462 | 2003-01-07 | ||
PCT/EP2004/000023 WO2004060957A1 (en) | 2003-01-07 | 2004-01-06 | Phosphorus-modified epoxy resin |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1583788A1 true EP1583788A1 (en) | 2005-10-12 |
Family
ID=32519747
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04700258A Ceased EP1583788A1 (en) | 2003-01-07 | 2004-01-06 | Phosphorus-modified epoxy resin |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1583788A1 (en) |
DE (1) | DE10300462A1 (en) |
TW (1) | TWI301841B (en) |
WO (1) | WO2004060957A1 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1625171A1 (en) * | 2003-05-22 | 2006-02-15 | Supresta LLC | Polyphosphonate flame retardant curing agent for epoxy resin |
EP1751222A2 (en) * | 2004-04-01 | 2007-02-14 | Supresta U.S. LLC. | Low heat release and low smoke reinforcing fiber/epoxy composites |
US7910665B2 (en) | 2004-05-19 | 2011-03-22 | Icl-Ip America Inc. | Composition of epoxy resin and epoxy-reactive polyphosphonate |
EP2152793A1 (en) * | 2007-06-14 | 2010-02-17 | Basf Se | Flame retardant compositions |
CN101831139B (en) * | 2009-03-11 | 2013-08-28 | 联茂电子股份有限公司 | Epoxy resin compound and film and substrate made from same |
KR20180100348A (en) * | 2015-12-30 | 2018-09-10 | 사이텍 인더스트리스 인코포레이티드 | Multifunctional surface material with adaptive resistance |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2925207A1 (en) * | 1979-06-22 | 1981-01-29 | Bayer Ag | THERMOPLASTIC, BRANCHED, AROMATIC POLYPHOSPHONATES, THEIR USE AND A METHOD FOR THE PRODUCTION THEREOF |
CN1109702C (en) * | 1995-06-27 | 2003-05-28 | 日立化成工业株式会社 | Epoxy resin compsn. for printed wiring board and laminated board produced with the use of the same |
DE19608611A1 (en) * | 1996-03-06 | 1997-09-11 | Hoechst Ag | Phosphorus-modified coating compositions, a process for their preparation and their use |
JPH1180178A (en) * | 1997-09-12 | 1999-03-26 | Hitachi Chem Co Ltd | Oligomer terminated with phosphorus-containing phenol and its production |
EP1432719A1 (en) * | 2001-10-04 | 2004-06-30 | Akzo Nobel N.V. | Oligomeric, hydroxy-terminated phosphonates |
-
2003
- 2003-01-07 DE DE2003100462 patent/DE10300462A1/en not_active Withdrawn
-
2004
- 2004-01-02 TW TW93100057A patent/TWI301841B/en not_active IP Right Cessation
- 2004-01-06 EP EP04700258A patent/EP1583788A1/en not_active Ceased
- 2004-01-06 WO PCT/EP2004/000023 patent/WO2004060957A1/en active Application Filing
Non-Patent Citations (1)
Title |
---|
See references of WO2004060957A1 * |
Also Published As
Publication number | Publication date |
---|---|
TW200508271A (en) | 2005-03-01 |
WO2004060957A1 (en) | 2004-07-22 |
DE10300462A1 (en) | 2004-07-15 |
TWI301841B (en) | 2008-10-11 |
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Inventor name: VOS, SUSANNE Inventor name: REICHWEIN, HEINZ-GUNTER Inventor name: GRAEFEN, MELANIE Inventor name: ROTTLAENDER, CHRISTIAN |
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Inventor name: VOS, SUSANNE Inventor name: REICHWEIN, HEINZ-GUNTER Inventor name: GRAEFEN, MELANIE Inventor name: ROTTLAENDER, CHRISTIAN |
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