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WO2004113411A1 - Agent de durcissement ignifugeant de type polyphosphonate conçu pour une resine epoxy - Google Patents

Agent de durcissement ignifugeant de type polyphosphonate conçu pour une resine epoxy Download PDF

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Publication number
WO2004113411A1
WO2004113411A1 PCT/US2004/016459 US2004016459W WO2004113411A1 WO 2004113411 A1 WO2004113411 A1 WO 2004113411A1 US 2004016459 W US2004016459 W US 2004016459W WO 2004113411 A1 WO2004113411 A1 WO 2004113411A1
Authority
WO
WIPO (PCT)
Prior art keywords
epoxy resin
epoxy
polyphosphonate
composition
curing agent
Prior art date
Application number
PCT/US2004/016459
Other languages
English (en)
Inventor
Sergei Levchik
Andrew M. Piotrowski
Original Assignee
Supresta Llc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Supresta Llc filed Critical Supresta Llc
Priority to EP04776110A priority Critical patent/EP1625171A1/fr
Priority to CA002525856A priority patent/CA2525856A1/fr
Priority to US10/557,812 priority patent/US7910665B2/en
Priority to JP2006533410A priority patent/JP2007502904A/ja
Priority to TW093130123A priority patent/TWI356839B/zh
Publication of WO2004113411A1 publication Critical patent/WO2004113411A1/fr

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
    • C08G59/40—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
    • 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
    • C08G59/62—Alcohols or phenols
    • C08G59/621—Phenols
    • 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
    • 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
    • C08G59/4071—Curing agents not provided for by the groups C08G59/42 - C08G59/66 phosphorus containing compounds
    • 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 present invention relates to an epoxy resin composition that can be used, for example, in printed wiring boards for electronic applications. It represents a new embodiment, for example, over the type of flame retarded epoxy resin compositions described in PCT Patent Publication No. WO 03/029258 where an epoxy resin, which contained the type of polyphosphonate flame retardant additive that is also used in the epoxy resin compositions of the present invention, was cured in the presence of a methylimidazole curing catalyst.
  • the composition of the present invention contains, as one essential component, an epoxy resin.
  • This component is present at from about 50% to about 95%, by weight of the total weight of the composition.
  • This component can be a non-halogen containing epoxy resin, such as a bisphenol A- type of epoxy resin, or other resins of this general type that have utility for the manufacture of printed wiring boards or other electronic substrate materials of that type (for example, bisphenol F epoxy, phenolic novolak epoxy, cresol novolak epoxy, and/or bisphenol A novolak epoxy resins) .
  • a non-halogen containing epoxy resin such as a bisphenol A- type of epoxy resin, or other resins of this general type that have utility for the manufacture of printed wiring boards or other electronic substrate materials of that type (for example, bisphenol F epoxy, phenolic novolak epoxy, cresol novolak epoxy, and/or bisphenol A novolak epoxy resins) .
  • Compatible mixtures of any of these resins may be employed, if desired.
  • the polyphosphonate flame retardant curing agent that forms another essential additive of the compositions of the present invention is generally present at from about 5% to about 50%, by weight of the total weight of the composition, for example, from about 10% to about 35%, by weight.
  • this polyphosphonate functions as the effective curing agent for the epoxy resin.
  • This curing agent is an polyphosphonate composition having the formula: O O
  • ⁇ V Y" is an arylene and "n" can range from about 2 to about 30.
  • mixed arylenes diols and mixed alkylphosphonates can be used to prepare mixed products.
  • This oligomeric or polymeric material has a phosphorus content of greater than about 10%, by weight.
  • the polyphosphonate species in the composition comprise oligomers or polymers of this type that can either contain - OH end groups or not contain such end groups.
  • the individual polyphosphonate species that contain -OH end groups can be monohydroxy or dihydroxy-substituted.
  • the concentration of polyphosphonate species in the composition that contain hydroxy end groups can range from about 20% to about 100%, based upon the total number of termination ends ("chain ends") that potentially could hold such end groups, for example, from about 50% to about 100%.
  • the number of OH terminal groups can be controlled by the ratio of arylene to phosphonate or by using end-capping agents such as triaryl phosphates. In the former case, if excess arylene- containing diol is used with the phosphonate reagent, for example, in making the polyphosphonate, there will be a higher hydroxyl content in the final product, and vice versa.
  • the preferred R group is methyl, but can be lower alkyl .
  • Arylene is meant any radical of a dihydric phenol.
  • the dihydric phenol can have its two hydroxy groups in non- adjacent positions. Examples include the resorcinols; hydroquinones; and bisphenols, such as bisphenol A, bisphenol F, and 4, 4' -biphenol, phenolphthalein, 4,4'- thiodiphenol , or 4,4' -sulfonyldiphenol .
  • a small amount of polyhydric phenol, such as a novolac or phloroglucinol with three or more hydroxyl groups therein can be included to increase the molecular weight.
  • the Arylene group can be 1,3-phenylene, 1,4-phenylene, or a bisphenol diradical unit, but it is preferably 1,3-phenylene.
  • the polyphosphonate curing agent for the epoxy resin composition of this invention can be made by any of several routes: (1) the reaction of an RP0C1 2 with HO-Aryl-OH or a salt thereof, where R is lower alkyl, preferably methyl; (2) the reaction of diphenyl alkylphosphonate , preferably methylphosphonate , with HO-Arylene-OH under transesterification conditions; (3) the reaction of an oligomeric phosphite with repeating units of the structure - OP (OR' ) -O-Arylene- with an Arbuzov rearrangement catalyst, where R' is lower alkyl, preferably methyl; or (4) the reaction of an oligomeric phosphite with the repeating units having the structure -OP (O-Ph) -O-Arylene with trimethyl phosphite and an Arbuzov catalyst or with dimethyl methylphosphonate with, optionally, an Arbuzov catalyst-.
  • the -OH end groups, if attached to Arylene can be produced by having a controlled molar excess of the HO-Arylene-OH in the reaction media.
  • the -OH end groups, if acid type (P- OH) can be formed by hydrolytic reactions . It is preferred that the end groups of the oligomers be mainly -Arylene-OH types .
  • the epoxy resin composition of the present invention can contain optional additives like auxiliary flame retardant additive as well including the following types of materials: auxiliary curing catalysts, fiber and/or cloth reinforcing additives; mineral fillers, such as Al(OH) 3/ Mg(0H) 2 or silica; release agents; colorants; and the like.
  • auxiliary flame retardant additive like auxiliary flame retardant additive as well including the following types of materials: auxiliary curing catalysts, fiber and/or cloth reinforcing additives; mineral fillers, such as Al(OH) 3/ Mg(0H) 2 or silica; release agents; colorants; and the like.
  • Example 1 The aforementioned polyphosphonate curing agent (poly(m- phenylene methylphosphonate) (29.1 g) was mixed with 70.1 g of bisphenol A type epoxy (epoxy equivalent: 180) to prepare a master batch. A 10 g sample was removed from the master batch and was placed in a nitrogen-purged oven at 179°C. A sample was removed after ninety minutes and was cooled to room temperature. The Barkol hardness was than measured using Gl 934-1 meter. The sample was uniformly cured with a hardness of 28-29. The sample was submerged in acetone for twelve hours. No swelling or dissolution was observed.
  • poly(m- phenylene methylphosphonate) 29.1 g
  • bisphenol A type epoxy epoxy
  • Comparative Example 2 A lOg sample of bisphenol A type epoxy (epoxy equivalent: 180) was placed the nitrogen-purged oven at 179°C for one hundred minutes. Sample did not cure or gel. It was a viscous liquid at room temperature and was completely soluble in acetone.
  • FYROL PNX brand from Akzo Nobel was mixed with a bisphenol A di-epoxy resin (epoxy equivalent of 180) to form a mixture containing 70% of epoxy resin and 30% of FYROL PNX. Mixture was placed in the oven at 150°C for one and one half hours. It did not cure.
  • a polyphosphonate which is the reaction product of dimethyl methylphosphonate, P 2 0 5 and ethylene oxide (FYROL HP brand from Akzo Nobel) with a hydroxyl number of 125mg KOH/g was mixed with a bisphenol A di-epoxy resin (epoxy equivalent 180) to form a mixture containing 70% of epoxy resin and 30% of the polyphosphonate. The mixture was placed in an oven at 150°C for one and one half hours. It did not cure.
  • the epoxy insertion product as described in Example 7 was placed in the oven at 150°C for one hour and then the temperature was increased to 180°C over a period of one hour.
  • the resulting cured epoxy composition had a BARKOL hardness of 32 (measured using Gl 934-1 meter) .
  • the epoxy insertion product as described in Example 7 was dissolved in acetone and mixed with ATH to make a blend containing 62% ATH by weight and 38% of the epoxy composition.
  • Acetone was evaporated under reduced pressure and resulting paste mixed well and cured at 150°C for one hour followed by a gradual temperature increase to 160°C over a period of thirty minutes.
  • the resulting cured epoxy composition had a BARKOL hardness of 52.
  • the epoxy insertion product as described in Example 7 dissolved in acetone and combined with 1000 ppm of methylimidazole and 1000 ppm of triphenyl phosphine. Acetone was evaporated under reduced pressure and sample cured at 138°C for one hour. The resulting cured epoxy composition had a BARKOL hardness of 25.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition de résine époxy comprenant une résine époxy et, en tant qu'agent de durcissement efficace, un polyphosphonate qui réagit avec la résine époxy et qui peut être de formule (I), dans laquelle « Y » représente un arylène, et « n » peut se trouver dans la plage comprise entre approximativement 2 et approximativement 30.
PCT/US2004/016459 2003-05-22 2004-05-19 Agent de durcissement ignifugeant de type polyphosphonate conçu pour une resine epoxy WO2004113411A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP04776110A EP1625171A1 (fr) 2003-05-22 2004-05-19 Agent de durcissement ignifugeant de type polyphosphonate con u pour une resine epoxy
CA002525856A CA2525856A1 (fr) 2003-05-22 2004-05-19 Agent de durcissement ignifugeant de type polyphosphonate concu pour une resine epoxy
US10/557,812 US7910665B2 (en) 2004-05-19 2004-05-19 Composition of epoxy resin and epoxy-reactive polyphosphonate
JP2006533410A JP2007502904A (ja) 2003-05-22 2004-05-19 ポリエキシ樹脂用ポリホスホネート難燃硬化剤
TW093130123A TWI356839B (en) 2004-05-19 2004-10-05 Polyphosphonate flame retardant curing agent for e

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US47265403P 2003-05-22 2003-05-22
US60/472,654 2003-05-22

Publications (1)

Publication Number Publication Date
WO2004113411A1 true WO2004113411A1 (fr) 2004-12-29

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/016459 WO2004113411A1 (fr) 2003-05-22 2004-05-19 Agent de durcissement ignifugeant de type polyphosphonate conçu pour une resine epoxy

Country Status (6)

Country Link
EP (1) EP1625171A1 (fr)
JP (1) JP2007502904A (fr)
KR (1) KR20060019547A (fr)
CN (1) CN1795223A (fr)
CA (1) CA2525856A1 (fr)
WO (1) WO2004113411A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010051182A1 (fr) * 2008-10-29 2010-05-06 Icl-Ip America Inc. Composition de résine époxy retardatrice de flamme contenant du phosphore, préimprégné et stratifié à base de celle-ci
US20110132646A1 (en) * 2009-06-12 2011-06-09 Icl-Ip America Inc. Flame retardant epoxy resin composition, prepreg and laminate thereof
EP2655384A2 (fr) * 2010-12-22 2013-10-30 FRX Polymers, Inc. Phosphonates oligomères et compositions les comprenant
EP2716718A1 (fr) * 2011-06-03 2014-04-09 Arisawa Mfg. Co., Ltd. Composition de résine ignifuge, stratifié à revêtement en métal pour carte à circuits imprimés souple utilisant cette composition; couche de revêtement; feuille adhésive destinée à une carte de circuits imprimés souple et carte de circuits imprimés souple
US10167377B2 (en) 2013-01-22 2019-01-01 Frx Polymers, Inc. Phosphorus containing epoxy compounds and compositions therefrom
US11359047B2 (en) 2017-09-13 2022-06-14 Hexion Inc. Epoxy resin systems

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WO2006026616A1 (fr) * 2004-08-31 2006-03-09 Supresta Llc Procede pour preparer des diaryl alkyl phosphonates, et des derives oligomeres/polymeres correspondants
EP2152793A1 (fr) * 2007-06-14 2010-02-17 Basf Se Compositions ignifuges
TWI472558B (zh) * 2011-12-22 2015-02-11 Frx Polymers Inc 寡聚膦酸酯及包含該寡聚膦酸酯之組成物
KR101469270B1 (ko) * 2011-12-30 2014-12-08 제일모직주식회사 폴리포스포네이트 공중합체, 그 제조 방법 및 이를 포함하는 난연성 열가소성 수지 조성물
CN105802127B (zh) * 2014-12-29 2018-05-04 广东生益科技股份有限公司 一种无卤热固性树脂组合物及使用它的预浸料以及印制电路用层压板
CN105801814B (zh) * 2014-12-29 2018-05-04 广东生益科技股份有限公司 一种无卤热固性树脂组合物及使用它的预浸料和印制电路用层压板
CN105330824A (zh) * 2015-12-09 2016-02-17 西安元创化工科技股份有限公司 一种用于环氧树脂的阻燃固化剂及其制备方法
TWI620785B (zh) * 2016-08-10 2018-04-11 Taiwan Union Technology Corporation 樹脂組成物、及使用該樹脂組成物所製得之預浸漬片、金屬箔積層板及印刷電路板
TWI620763B (zh) * 2017-04-27 2018-04-11 Taiwan Union Technology Corporation 樹脂組成物、及使用該樹脂組成物所製得之預浸漬片、金屬箔積層板及印刷電路板
CN107903383A (zh) * 2017-11-22 2018-04-13 吉林省高性能复合材料制造业创新中心有限公司 中低温固化环氧树脂及其制备方法与在大小丝束碳纤维环氧复合传动轴中的应用
CN107778456A (zh) * 2017-11-22 2018-03-09 吉林省高性能复合材料制造业创新中心有限公司 中低温固化环氧树脂及其制备方法与在大丝束碳纤维环氧复合传动轴中的应用
CN109705530B (zh) * 2018-12-29 2021-06-04 广东生益科技股份有限公司 热固性树脂组合物及含有它的预浸料、层压板和高频电路基板
CN112480373A (zh) * 2019-09-11 2021-03-12 广东广山新材料股份有限公司 一种阻燃性环氧树脂组合物及其制备方法和应用

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WO2003029258A1 (fr) * 2001-10-04 2003-04-10 Akzo Nobel N.V. Phosphonates oligomeres a terminaison hydroxy
WO2004044054A1 (fr) * 2002-11-08 2004-05-27 Akzo Nobel N.V. Composition de resine epoxy contenant un oligomere phosphonate ignifugeant reactif et une charge
WO2004060957A1 (fr) * 2003-01-07 2004-07-22 Bakelite Ag Resine epoxyde modifiee par des composes phosphoreux

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WO2003029258A1 (fr) * 2001-10-04 2003-04-10 Akzo Nobel N.V. Phosphonates oligomeres a terminaison hydroxy
WO2004044054A1 (fr) * 2002-11-08 2004-05-27 Akzo Nobel N.V. Composition de resine epoxy contenant un oligomere phosphonate ignifugeant reactif et une charge
WO2004060957A1 (fr) * 2003-01-07 2004-07-22 Bakelite Ag Resine epoxyde modifiee par des composes phosphoreux

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010051182A1 (fr) * 2008-10-29 2010-05-06 Icl-Ip America Inc. Composition de résine époxy retardatrice de flamme contenant du phosphore, préimprégné et stratifié à base de celle-ci
US20110132646A1 (en) * 2009-06-12 2011-06-09 Icl-Ip America Inc. Flame retardant epoxy resin composition, prepreg and laminate thereof
EP2655384A2 (fr) * 2010-12-22 2013-10-30 FRX Polymers, Inc. Phosphonates oligomères et compositions les comprenant
EP2655384A4 (fr) * 2010-12-22 2014-04-16 Frx Polymers Inc Phosphonates oligomères et compositions les comprenant
US8779041B2 (en) 2010-12-22 2014-07-15 Frx Polymers, Inc. Oligomeric phosphonates and compositions including the same
EP2716718A1 (fr) * 2011-06-03 2014-04-09 Arisawa Mfg. Co., Ltd. Composition de résine ignifuge, stratifié à revêtement en métal pour carte à circuits imprimés souple utilisant cette composition; couche de revêtement; feuille adhésive destinée à une carte de circuits imprimés souple et carte de circuits imprimés souple
EP2716718A4 (fr) * 2011-06-03 2015-04-15 Frx Polymers Inc Composition de résine ignifuge, stratifié à revêtement en métal pour carte à circuits imprimés souple utilisant cette composition; couche de revêtement; feuille adhésive destinée à une carte de circuits imprimés souple et carte de circuits imprimés souple
US10167377B2 (en) 2013-01-22 2019-01-01 Frx Polymers, Inc. Phosphorus containing epoxy compounds and compositions therefrom
US11359047B2 (en) 2017-09-13 2022-06-14 Hexion Inc. Epoxy resin systems
CN115260453A (zh) * 2017-09-13 2022-11-01 瀚森公司 环氧树脂体系
CN115260453B (zh) * 2017-09-13 2023-10-03 瀚森公司 环氧树脂体系

Also Published As

Publication number Publication date
EP1625171A1 (fr) 2006-02-15
CN1795223A (zh) 2006-06-28
JP2007502904A (ja) 2007-02-15
CA2525856A1 (fr) 2004-12-29
KR20060019547A (ko) 2006-03-03

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