WO2021237696A1 - Composition de résine à très faible perte sans halogène - Google Patents

Composition de résine à très faible perte sans halogène Download PDF

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Publication number
WO2021237696A1
WO2021237696A1 PCT/CN2020/093361 CN2020093361W WO2021237696A1 WO 2021237696 A1 WO2021237696 A1 WO 2021237696A1 CN 2020093361 W CN2020093361 W CN 2020093361W WO 2021237696 A1 WO2021237696 A1 WO 2021237696A1
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group
weight
composition
formula
hydrogen
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PCT/CN2020/093361
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English (en)
Inventor
Simon YE
Ethan Wang
Emerson Bao
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Blue Cube IP LLC
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Blue Cube IP LLC
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Priority to PCT/CN2020/093361 priority Critical patent/WO2021237696A1/fr
Priority to CN202080101485.7A priority patent/CN115698178A/zh
Priority to TW110119406A priority patent/TWI887423B/zh
Priority to TW114118426A priority patent/TW202534123A/zh
Publication of WO2021237696A1 publication Critical patent/WO2021237696A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/093—Polyol derivatives esterified at least twice by phosphoric acid groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • 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
    • C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • C08K5/14—Peroxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08L71/12—Polyphenylene oxides
    • C08L71/126—Polyphenylene oxides modified by chemical after-treatment
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
    • 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
    • H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
    • 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

  • PCB printed circuit board
  • PPE acrylate capped polyphenyl ether
  • a resin composition comprising: an organophosphorus olefin, in an amount of from about 10%by weight to about 65%by weight of the composition; an unsaturated resin, in an amount of from 0%by weight to about 50%by weight of the composition; silica, in an amount of from about 20%by weight to about 80%by weight of the composition; and a free radical initiator, in an amount of from about 0.5%by weight to about 7.5%by weight of the composition.
  • the resin composition provided herein comprises an organophosphorus olefin of Formula A,
  • each Ar 1 is independently a moiety of structure (1) ;
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • each Ar 2 is independently selected from the group consisting of structure (4) , structure (5) , structure (6) , structure (7) , structure (8) , and structure (9) ;
  • each X is independently selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen and alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl; and n is an integer greater than or equal to 1.
  • the organophosphorus olefin may comprise a compound of Formula I, Formula Ia, Formula II, Formula IIa, Formula IIb, Formula IIc, Formula IId, Formula IIe, Formula IIf, Formula III, Formula IIIa, Formula IIIb, Formula IIIc, Formula IIId, Formula IIIe, or Formula IIIf.
  • a printed circuit board comprising a cured resin composition, wherein the resin composition is as provided herein.
  • halogen-free, flame retardant curable resin compositions that provide both good electrical characteristics and good heat resistance characteristics sufficient to allow for their use in high-performance PCB systems.
  • organophosphorus olefins that are useful as reactive-type flame retardants.
  • these reactive-type compounds provide good dielectric performance and heat resistance when incorporated into PCB compositions.
  • a resin composition comprising an organophosphorus olefin, an unsaturated resin, silica, and a free radical initiator.
  • the resin composition may comprise one or more organophosphorous olefins as provided herein.
  • organophosphorous olefins as provided herein.
  • the organophosphorous olefins provided herein are useful as reactive-type flame retardants, and provide surprisingly good dielectric performance and heat resistance when incorporated into PCB compositions.
  • the resin composition may comprise an organophosphorus olefin, for example, in an amount of from about 10%by weight to about 65%by weight, from about 15%by weight to about 50%by weight, from about 20%by weight to about 40%by weight, from about 20%by weight to about 35%by weight, or from about 25%by weight to about 35%by weight of the composition.
  • organophosphorus olefin for example, in an amount of from about 10%by weight to about 65%by weight, from about 15%by weight to about 50%by weight, from about 20%by weight to about 40%by weight, from about 20%by weight to about 35%by weight, or from about 25%by weight to about 35%by weight of the composition.
  • the resin composition comprises a compound of Formula A,
  • each Ar 1 is independently a moiety of structure (1) ;
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • each Ar 2 is independently selected from the group consisting of structure (4) , structure (5) , structure (6) , structure (7) , structure (8) , and structure (9) ;
  • each X is independently selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen and alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • R 4 and R 5 are each independently selected from the group consisting of structure (1) , structure (2) , and structure (3) ;
  • alkyl refers to a straight or branched chain moiety comprising up to 10 carbon atoms.
  • suitable alkyl groups include methyl, ethyl, propyl, butyl, pentyl, and hexyl.
  • the alkyl group may be a straight-chain alkyl group or a branched alkyl group (e.g., isopropyl) .
  • the alkyl group is optionally independently substituted with one or more substituents selected from the group consisting of methoxyl, carboxyl, .
  • aryl refers to an aromatic moiety comprising from 6 to 14 carbon atoms.
  • the aryl group is optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl.
  • suitable aryl groups include phenyl, naphthyl, benzyl, tolyl, and xylyl.
  • alkoxyl refers to a group of the form -OR′, wherein R′ is alkyl as defined herein.
  • R′ is alkyl as defined herein.
  • the group -OCH 3 may be referred to herein as “methoxyl. ”
  • the group -OCH 2 CH 3 may be referred to herein as “ethoxyl. ”
  • aryloxyl refers to a group of the form -OR′, wherein R′ is aryl as defined herein.
  • R′ is aryl as defined herein.
  • the group -O (C 6 H 6 ) may be referred to herein as “phenoxyl. ”
  • hydrogen includes both stable isotopes of hydrogen, namely 1 H (also known as protium) and 2 H (also known as deuterium) .
  • carboxyl refers to a group of the form -C (O) OH.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • each Ar 2 is the same.
  • each Ar 2 may be a moiety of structure (4) wherein each X is the same.
  • each Ar 2 is a moiety of structure (5) .
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n is an integer of from 1 to 10.
  • n may be 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • n is 1.
  • the resin composition may comprise a compound of Formula I,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, ;
  • each Ar 2 is independently selected from the group consisting of structure (4) , structure (5) , structure (6) , structure (7) , structure (8) , and structure (9) ;
  • each X is independently selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen and alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , Ar 2 , X, and n may be selected as described above with respect to Formula A.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • Ar 2 is selected from the group consisting of structure (4) and structure (5) , and each Ar 2 is the same.
  • Ar 2 is a moiety of structure (4)
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n 1
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • each X is independently selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , X, and n may be selected as described above with respect to Formula A and/or Formula I.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, X is -C (CH 3 ) 2 -, n is 1, and the compound is Formula Ia-i.
  • the resin composition may comprise a compound of Formula II,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • each Ar 2 is independently selected from the group consisting of structure (4) , structure (5) , structure (6) , structure (7) , structure (8) , and structure (9) ;
  • each X is independently selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen and alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , Ar 2 , X, and n may be selected as described above with respect to Formula A.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • Ar 2 is selected from the group consisting of structure (4) and structure (5) , and each Ar 2 is the same.
  • Ar 2 is a moiety of structure (4)
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n 1
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • X is selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , X, and n may be selected as described above with respect to Formula A and/or Formula II.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, X is -C (CH 3 ) 2 -, n is 1, and the compound is Formula IIa-i.
  • the resin composition may comprise a compound of Formula IIb,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , and n may be selected as described above with respect to Formula A and/or Formula II.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, n is 1, and the compound is Formula IIb-i.
  • the resin composition may comprise a compound of Formula IIc,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , and n may be selected as described above with respect to Formula A and/or Formula II.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, n is 1, and the compound is Formula IIc-i.
  • the resin composition may comprise a compound of Formula IId,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , and n may be selected as described above with respect to Formula A and/or Formula II.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, n is 1, and the compound is Formula IId-i.
  • the resin composition may comprise a compound of Formula IIe,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , and n may be selected as described above with respect to Formula A and/or Formula II.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, n is 1, and the compound is Formula IIe-i.
  • the resin composition may comprise a compound of Formula IIf,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • each X is independently selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen and alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , R 6 , R 7 , X, and n may be selected as described above with respect to Formula A and/or Formula II.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n 1
  • R 1 and R 2 are methyl, R 3 , R 6 , and R 7 are each hydrogen, X is -C (CH 3 ) 2 -, n is 1, and the compound is Formula IIf-i.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • each Ar 2 is independently selected from the group consisting of structure (4) , structure (5) , structure (6) , structure (7) , structure (8) , and structure (9) ;
  • each X is independently selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen and alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , Ar 2 , X, and n may be selected as described above with respect to Formula A.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • Ar 2 is selected from the group consisting of structure (4) and structure (5) , and each Ar 2 is the same.
  • Ar 2 is a moiety of structure (4)
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n 1
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • X is selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , X, and n may be selected as described above with respect to Formula A and/or Formula III.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, X is -C (CH 3 ) 2 -, n is 1, and the compound is Formula IIIa-i.
  • the resin composition may comprise a compound of Formula IIIb,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , and n may be selected as described above with respect to Formula A and/or Formula III.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, n is 1, and the compound is Formula IIIb-i.
  • the resin composition may comprise a compound of Formula IIIc,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , and n may be selected as described above with respect to Formula A and/or Formula III.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, n is 1, and the compound is Formula IIIc-i.
  • the resin composition may comprise a compound of Formula IIId,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , and n may be selected as described above with respect to Formula A and/or Formula III.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, n is 1, and the compound is Formula IIId-i.
  • the resin composition may comprise a compound of Formula IIIe,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , and n may be selected as described above with respect to Formula A and/or Formula III.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • n 1
  • R 1 and R 2 are methyl, R 3 is hydrogen, n is 1, and the compound is Formula IIIe-i.
  • the resin composition may comprise a compound of Formula IIIf,
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • each X is independently selected from the group consisting of -CH 2 -, -C (CH 3 ) 2 -, -S-, -SO 2 -, -O-, and -CO-;
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen and alkyl, aryl, alkoxyl, and aryloxyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of methyl, ethyl, methoxyl, and carboxyl;
  • n is an integer greater than or equal to 1.
  • each of R 1 , R 2 , R 3 , R 6 , R 7 , X, and n may be selected as described above with respect to Formula A and/or Formula III.
  • R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen and C 1 –C 6 alkyl.
  • R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 –C 6 alkyl and R 3 is hydrogen.
  • X is selected from the group consisting of -CH 2 -and -C (CH 3 ) 2 -.
  • X can be -C (CH 3 ) 2 -.
  • n 1
  • R 1 and R 2 are methyl, R 3 , R 6 , and R 7 are each hydrogen, X is -C (CH 3 ) 2 -, n is 1, and the compound is Formula IIIf-i.
  • the resin composition may further comprise one or more unsaturated resins.
  • the resin composition may comprise the one or more unsaturated resins, for example, in an amount of from about 0%by weight to about 50%by weight, from about 10%to about 40%by weight, from about 10%to about 30%by weight, from about 15%to about 30%by weight, or from about 15%to about 25%by weight of the composition.
  • Non-limiting examples of unsaturated resins include acrylate capped polyphenyl ether; bismaleimide; and mixtures thereof.
  • the resin composition may comprise an acrylate capped polyphenyl ether of Formula B
  • Y is an aliphatic backbone comprising 1 or more carbon atoms, and m and n are each independently greater than or equal to 1.
  • Y is an aliphatic backbone comprising between 1 and 20 carbon atoms, for example, between 1 and 10 carbon atoms, between 1 and 8 carbon atoms, or between 1 and 6 carbon atoms.
  • the concentration of the acrylate capped polyphenyl ether is preferably from about 20%by weight to about 80%by weight, for example, from about 40%by weight to about 70%by weight, from about 45%by weight to about 65%by weight, or from about 50%by weight to about 60%by weight of the composition.
  • the resin composition may comprise a bismaleimide of Formula C
  • R 1 is selected from the group consisting of: an aliphatic backbone comprising 1 or more carbon atoms, and a cycloaliphatic backbone comprising a ring with 3 or more members;
  • R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of hydrogen and C 1 –C 3 alkyl.
  • R 1 is an aliphatic backbone comprising between 1 and 20 carbon atoms, for example, between 1 and 10 carbon atoms, between 1 and 8 carbon atoms, or between 1 and 6 carbon atoms.
  • the concentration of the bismaleimide is preferably from about 1%by weight to about 50%by weight, for example, from about 10%by weight to about 40%by weight, from about 15%by weight to about 35%by weight, or from about 20%by weight to about 30%by weight of the composition.
  • the resin composition comprises a combination of two or more unsaturated resins.
  • the resin composition may comprise a combination of (1) an acrylate capped polyphenyl ether (including but not limited to a compound of Formula B) , and (2) a bismaleimide (including but not limited to a compound of Formula C) .
  • the concentration of the acrylate capped polyphenyl ether may range from 1%by weight to about 30%by weight, from about 2%by weight to about 25%by weight, from about 5%by weight to about 20%by weight, or from about 5%by weight to about 15%by weight of the composition.
  • the concentration of the bismaleimide may range, for example, from 1%by weight to about 30%by weight, from about 2%by weight to about 25%by weight, from about 5%by weight to about 20%by weight, or from about 5%by weight to about 15%by weight of the composition.
  • the resin composition may further comprise a filler component.
  • a filler component can improve the dimensional stability, mechanical strength, and/or thermal conductivity of the composition.
  • suitable filler components include spherical silica, fused silica, aluminum oxide, aluminum hydroxide, magnesium oxide, magnesium hydroxide, boron nitride, mica, talc, and mixtures thereof.
  • the filler component comprises an inorganic filler.
  • the filler component may comprise silica.
  • the resin composition may comprise the filler component, for example, in an amount of from about 20%by weight to about 80%by weight, from about 30%to about 70%by weight, or from about 40%by weight to about 60%by weight of the composition.
  • the resin composition may comprise one or more free radical initiators.
  • the free radical initiator may act to release free radicals at elevated temperature, and thereby trigger the cross linking of all the components in the composition.
  • Non-limiting examples of free radical initiators include dicumyl peroxide, di-tert-butyl peroxide, and benzoyl peroxide.
  • the free radical initiator may comprise a peroxide compound.
  • the resin composition may comprise the one or more free radical initiators, for example, in an amount of from about 0.5%by weight to about 7.5%by weight, from about 0.5%by weight to about 5%by weight, from about 0.5%by weight to about 2.5%by weight, from about 1%by weight to about 2.5%by weight, or from about 1.5%by weight to about 2.5%by weight of the composition.
  • a printed circuit board comprising a resin composition as provided herein.
  • compositions provided herein can be formulated using typical techniques that are known to those skilled in the art.
  • SA9000 is acrylate terminated polyphenyl ether available from SABIC.
  • TAIC is triallyl isocyanurate available from Tokyo Chemical Industry Co.
  • PX200 is resorcinol bis [di (2, 6-dimethylphenyl) phosphate] available from Daihachi Chemical Industry Co.
  • BMI 5100 is 3, 3'-dimethyl-5, 5'-diethyl-4, 4'-diphenylmethane bismaleimide available from Daiwakasei Industry Co.
  • SC2300-SVJ is spherical silica available from Admatechs Co., Ltd.
  • DCP is dicumyl peroxide available from Sinopharm Chemical Reagent Co.
  • SPB100 is hexaphenoxycyclotriphosphazene available from Otsuka Chemical Co.
  • tBuO 2 refers to di-tert-butyl peroxide, available from Sinopharm Chemical Reagent Co.
  • a varnish was prepared by combining the Example formulations with methyl ethyl ketone solvent (50%of the varnish composition by weight) .
  • methyl ethyl ketone solvent 50%of the varnish composition by weight
  • Into a tray was poured about 200 grams of varnish.
  • One piece of 2116 glass cloth (about 30 cm ⁇ 30 cm) was dipped into the varnish and then hand pulled through a gapped pair of rollers to control the thickness.
  • One edge of the prepared glass cloth was fixed by clamps and then hung in a fume hood to allow the varnish to evenly spread and promote solvent evaporation.
  • the glass cloth was then baked in a mini-treater (with good ventilation capability) at elevated temperature for a period of time sufficient to remove the solvent and generate a reasonable prepreg gel time, so the temperature and the time could be adjusted according to specific cases. Following the baking, the desired prepregs were obtained.
  • Table 2 demonstrates that the Inventive Examples comprising an Organophosphorus Olefin provide an ideal balance between Tg, Td, and Df when used in a laminate application.
  • the Organophosphorous Olefin of Formula IIa was formulated with SA9000.
  • the laminate could achieve 182°C Tg and promising low loss, 0.0028 Df at 1 GHz, while the flame retardancy was compromised to V-1 level.
  • Inventive Example 5 to further increase the thermal resistance, BMI resin and spherical silica were included into the formulation.
  • the laminate Tg increased to 205°C with a good low loss, 0.0025 Df at 1 GHz.
  • the articles “a” , “an” , “the” , and “said” are intended to mean that there are one or more of the elements.
  • the terms “comprising” , “including” , and “having” are intended to be inclusive and mean that there may be additional elements other than the listed elements.

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Abstract

L'invention concerne des compositions de résine durcissables retardatrices de flamme, sans halogène, qui assurent tant de bonnes caractéristiques électriques que de bonnes caractéristiques de résistance à la chaleur, suffisantes pour permettre leur utilisation dans des systèmes de circuits imprimés haute performance. En particulier, l'invention porte sur de nouvelles oléfines organophosphorées qui peuvent être utilisées comme retardateurs de flamme à temps de réaction. D'une manière surprenante, il a été découvert que ces composés de type réactif assurent de bonne performance diélectrique et une bonne résistance à la chaleur lorsqu'ils sont incorporés dans des compositions de circuits imprimés. La présence de liaisons doubles C=C dans ces oléfines organophosphorées leur permet de réagir avec des résines insaturées (par exemple, de l'éther de polyphényle à double coiffe C=C, de l'imide bismaléique, etc.) pour former un réseau réticulé.
PCT/CN2020/093361 2020-05-29 2020-05-29 Composition de résine à très faible perte sans halogène Ceased WO2021237696A1 (fr)

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PCT/CN2020/093361 WO2021237696A1 (fr) 2020-05-29 2020-05-29 Composition de résine à très faible perte sans halogène
CN202080101485.7A CN115698178A (zh) 2020-05-29 2020-05-29 无卤素的极低损耗树脂组合物
TW110119406A TWI887423B (zh) 2020-05-29 2021-05-28 無鹵素的極低損耗樹脂組合物
TW114118426A TW202534123A (zh) 2020-05-29 2021-05-28 無鹵素的極低損耗樹脂組合物

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JP7397227B1 (ja) 2023-02-07 2023-12-12 四国化成工業株式会社 リン化合物、その合成方法およびその利用
WO2024171871A1 (fr) * 2023-02-14 2024-08-22 日鉄ケミカル＆マテリアル株式会社 Composé de (méth)acryloyle contenant du phosphore, composé de vinyle et benzyle contenant du phosphore, procédés de production associés, composition de résine ignifuge et carte stratifiée pour carte de circuit électronique la contenant

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CN102276837A (zh) * 2011-08-19 2011-12-14 慧智科技（中国）有限公司 无卤含磷的阻燃聚酰亚胺树脂组合物及其制备方法
WO2017067140A1 (fr) * 2015-10-22 2017-04-27 广东生益科技股份有限公司 Composite de résine polyphényléther, préimprégné et stratifié comportant celui-ci, ainsi que carte de circuit imprimé
WO2019112920A1 (fr) * 2017-12-06 2019-06-13 Icl-Ip America Inc. Composé additif polysiloxane contenant du phosphore pour résines thermodurcissables, composition ignifuge comprenant celui-ci, et articles fabriqués à partir de celui-ci

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* Cited by examiner, † Cited by third party
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JP7397227B1 (ja) 2023-02-07 2023-12-12 四国化成工業株式会社 リン化合物、その合成方法およびその利用
WO2024166557A1 (fr) * 2023-02-07 2024-08-15 四国化成工業株式会社 Composé phosphore, et procédé de synthèse ainsi qu'application associés
JP2024111858A (ja) * 2023-02-07 2024-08-20 四国化成工業株式会社 リン化合物、その合成方法およびその利用
WO2024171871A1 (fr) * 2023-02-14 2024-08-22 日鉄ケミカル＆マテリアル株式会社 Composé de (méth)acryloyle contenant du phosphore, composé de vinyle et benzyle contenant du phosphore, procédés de production associés, composition de résine ignifuge et carte stratifiée pour carte de circuit électronique la contenant

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