CN106946937A - 一种含氰基的磷腈化合物、制备方法和用途 - Google Patents
一种含氰基的磷腈化合物、制备方法和用途 Download PDFInfo
- Publication number
- CN106946937A CN106946937A CN201610012162.6A CN201610012162A CN106946937A CN 106946937 A CN106946937 A CN 106946937A CN 201610012162 A CN201610012162 A CN 201610012162A CN 106946937 A CN106946937 A CN 106946937A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- phosphazene compound
- copper
- cyano
- 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.)
- Pending
Links
Classifications
-
- 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 System
- 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
- C07F9/6581—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
- C07F9/65815—Cyclic phosphazenes [P=N-]n, n>=3 n = 3
-
- 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 System
- 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
- C07F9/6581—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/659—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having three phosphorus atoms as ring hetero atoms in the same ring
-
- 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
-
- 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
-
- 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
- B32B15/09—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 comprising polyesters
-
- 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
- B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
-
- 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
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- 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
- B32B9/00—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00
- B32B9/005—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00 comprising one layer of ceramic material, e.g. porcelain, ceramic tile
-
- 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
- B32B9/00—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00
- B32B9/005—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00 comprising one layer of ceramic material, e.g. porcelain, ceramic tile
- B32B9/007—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00 comprising one layer of ceramic material, e.g. porcelain, ceramic tile comprising carbon, e.g. graphite, composite carbon
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/24—Derivatives of hydrazine
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
-
- 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
- C09D185/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon; Coating compositions based on derivatives of such polymers
- C09D185/02—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon; Coating compositions based on 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- 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
-
- 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
- H05K1/09—Use of materials for the conductive, e.g. metallic pattern
-
- 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
- B32B2255/00—Coating on the layer surface
-
- 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
- B32B2255/00—Coating on the layer surface
- B32B2255/02—Coating on the layer surface on fibrous or filamentary layer
-
- 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
- B32B2255/00—Coating on the layer surface
- B32B2255/10—Coating on the layer surface on synthetic resin layer or on natural or synthetic rubber layer
-
- 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
- B32B2255/00—Coating on the layer surface
- B32B2255/26—Polymeric coating
-
- 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
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/02—Composition of the impregnated, bonded or embedded layer
- B32B2260/021—Fibrous or filamentary layer
-
- 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
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—Synthetic resin
-
- 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
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/101—Glass fibres
-
- 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
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/106—Carbon fibres, e.g. graphite fibres
-
- 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
- B32B2305/00—Condition, form or state of the layers or laminate
- B32B2305/07—Parts immersed or impregnated in a matrix
-
- 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
- B32B2311/00—Metals, their alloys or their compounds
- B32B2311/12—Copper
-
- 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
- B32B2313/00—Elements other than metals
- B32B2313/04—Carbon
-
- 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
- B32B2315/00—Other materials containing non-metallic inorganic compounds not provided for in groups B32B2311/00 - B32B2313/04
- B32B2315/02—Ceramics
-
- 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
- B32B2333/00—Polymers of unsaturated acids or derivatives thereof
- B32B2333/04—Polymers of esters
-
- 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
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
-
- 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
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
-
- 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
- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
-
- 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
- C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/22—Halogen free composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
Abstract
本发明涉及一种含氰基的磷腈化合物,其特征在于,所述磷腈化合物具有式(I)的结构:其中,Y和Y’均各自独立地选自有机基团;M1和M2均各自独立地选自磷腈基团,且M1含有m1个磷原子,M2含有m2个磷原子;X1、X1’、X2、X3和X4均各自独立地任选为第六主族元素中的任意一种;R和R’均各自独立地选自亚有机基团;a为≥0的整数,b为≥1的整数,c为≥0的整数,且满足a+b=2m1,d+2=2m2。本发明通过在磷腈基团上引入氰基,实现了与磷腈基团P、N的协同增效,提高了其热稳定性、阻燃型以及与其他组分的配伍性均表现优异,含有本发明所述的磷腈化合物的树脂组合物具有良好的耐热性、耐水性、粘结性和机械性能,从而扩大了其应用范围。
Description
技术领域
本发明属于阻燃物质的技术领域,尤其涉及含氰基的磷腈化合物、制备方法及在复合金属基板上的用途。
背景技术
以手机、电脑、摄像机、电子游戏机为代表的电子产品、以空调、冰箱、电视影像、音响用品等为代表的家用、办公电器产品以及其他领域使用的各种产品,为了安全,很大部分的产品都要求其具备不同程度的阻燃性能。
为了使产品达到所要求的阻燃性能或等级,传统的技术常常使用向材料体系中添加如氢氧化铝水合物、氢氧化镁水合物等含有结晶水的金属氢氧化物等类的无机阻燃物质、和向体系材料中添加如溴化双酚A、溴化双酚A型环氧树脂等含溴量比较高的或含卤素量比较高的有机化学物质,为了提高这些含有卤素的有机化学物质的阻燃性,还常常在体系中再加入如三氧化二锑等对环境不友好的无机化学阻燃剂物质。
由于使用含卤素的阻燃物质,其燃烧时会产生无降解性或难降解的有毒物质如二恶英类有机卤素化学物质污染环境、影响人类及动物健康。
出于保护环境的目的,使用含磷、含氮等不含卤素的化合物代替含卤素化合物作为阻燃剂,特别是在电子、电气、电器产业上,采用具有反应性的单官能(一个分子中只有一个活性反应基团)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物以下简称DOPO),更多的是采用DOPO的衍生化合物作为阻燃成分,添加或不添加氢氧化铝水合物、氢氧化镁水合物达到阻燃的效果。
在电子领域,通常使用DOPO与线性酚醛型环氧树脂、邻甲基酚醛环氧树脂、双酚A酚醛型环氧树脂等高成本、多官能环氧树脂与DOPO反应的生成物(简称DOPO环氧树脂)广泛应用作为覆铜板用途的环氧树脂材料。
这些使用DOPO环氧树脂所制造的覆铜板,具有良好的阻燃性能,但黏结性、耐热性、加工性等存在不少的缺陷,不适合制造现代通信需要的高多层、高可靠性、高黏结性、良好的加工性能的需要,以及由于高成本的原因,不利于普及到如手机等要求低成本的消费电子等民用品领域。
在电子领域,通常使用DOPO与如双酚A、双酚F、酚醛树脂、苯酚、邻甲酚的醚化物反应制得含有DOPO骨架的含酚化合物(统称含磷酚醛树脂)当做环氧树脂固化剂或阻燃性物质添加剂,应用作为覆铜板用途的环氧树脂材料的阻燃剂。
这些使用含磷酚醛当做阻燃成分的一部分或全部所制得的覆铜板,可以达到阻燃的目的,但耐酸碱性、耐化学药品性、黏结性、耐热性、加工性等存在不少的缺陷,不适合制造现代通信需要的高多层、高可靠性、高黏结性、良好的加工性能的需要,以及由于高成本的原因,不利于普及到如手机等要求低成本的消费电子等民用品领域。
随着电子产业向短、小、薄、高多层化、高可靠性要求的进一步提高、民用消费电子的普及使用以及越来越严峻的环境污染的压力等因素的要求,市场迫切需要材料具有良好的阻燃性、耐热性、良好的机械性能的廉价阻燃性物质。
发明内容
针对现有技术的不足,本发明的目的在于提供一种含氰基的磷腈化合物,所述磷腈化合物具有式(I)的结构:
其中,Y和Y’均各自独立地选自有机基团;
M1和M2均各自独立地选自磷腈基团,且M1含有m1个磷原子,M2含有m2个磷原子;
X1、X1’、X2、X3和X4均各自独立地任选为第六主族元素中的任意一种;
R和R’均各自独立地选自亚有机基团;
a为≥0的整数,b为≥1的整数,c为≥0的整数,且满足a+b=2m1,d+2=2m2。针对M1和M2中磷原子比例的不同,a、b、c、d的取值不同,只需要满足a+b=2m1,d+2=2m2即可。
在式(I)中,M1和M2为相同或者不相同的磷腈基团,本发明所述M1和M2均各自独立地选自具有式(II)结构的环状磷腈,或具有式(III)结构的线性磷腈;
在式(II)或式(III)中,n1为≥2的整数,n2为≥1的整数;
优选环三磷腈基、环四磷腈基或非环状聚磷腈基中的任意1种或至少2种的组合;优选环三磷腈基;
注意,M1、M2结构式的表示中,所出现符号仅仅是对“环状”结构的一种示意。
优选地,Y和Y’均各自独立地选自取代或未取代的直链烃基、取代或未取代的支链烃基或取代或未取代的芳香基;优选C1~C30的取代或未取代的直链烃基、C1~C30取代或未取代的支链烃基或C6~C30取代或未取代的芳香基;进一步优选C1~C10的取代或未取代的直链烃基、C1~C10取代或未取代的支链烃基或C6~C16取代或未取代的芳香基;特别优选苯基、甲苯基、二甲苯基、乙苯基、甲基、乙基、正丙基、正丁基、异丙基或异丁基。
进一步优选地,Y和Y’均各自独立地为苯基、甲苯基、二甲苯基或乙苯基。
这里,可以理解的是,Y和Y’较多的实例均为苯基。
优选地,R和R’均各自独立地选自取代或未取代的直链亚烃基、取代或未取代的支链亚烃基、取代或未取代的亚芳香基;优选C1~C30的取代或未取代的直链亚烃基、C1~C30取代或未取代的支链亚烃基、C6~C30取代或未取代的亚芳香基;进一步优选C1~C10的取代或未取代的直链亚烃基、C1~C10取代或未取代的支链亚烃基、C6~C16取代或未取代的亚芳香基;特别优选亚苯基、甲基亚苯基、二甲基亚苯基、乙基亚苯基、亚甲基、亚乙基、亚丙基、中丙基、亚正丁基或亚异丙基。
进一步优选地,R和R’均各自独立地为亚苯基、甲基亚苯基、二甲基亚苯基、乙基亚苯基或
这里,可以理解的是,R较多的实例为亚苯基。
这里,可以理解的是,R’较多的实例为亚苯基或
优选地,X1、X1’、X2、X3和X4均为O。
本发明所述磷腈化合物优选或其中,M1、M2、a、b、R、R’具有与权利要求1相同的选择范围;
优选地,所述磷腈化合物选自 其中,M1、M2、a、b具有与权利要求1相同的选择范围;
优选地,所述磷腈化合物选自
本发明中,带有曲线的化学键为断键,能够与另一个断键连接成为一个完整的化学键,使2个基团按照通式的结构连接,或者通过断键直接连接在连苯基的某个位置。
本发明所使用的术语“取代的”是指指定原子上的任何一个或多个氢原子被选自指定组的取代基取代,条件是所述指定原子不超过正常价态,并且取代的结果是产生稳定的化合物。当取代基是氧代基团或酮基(即=O)时,那么原子上的2个氢原子被取代。酮取代基在芳香环上不存在。“稳定的化合物”是指能够足够强健地从反应混合物中分离至有效的纯度并配制成有效的化合物。
本发明还提供了一种如前所述的含氰基的磷腈化合物的制备方法,所述方法包括如下步骤:
将磷腈氯化物与第一原料化合物进行亲核取代反应,得到含氰基的磷腈化合物;
所述磷腈氯化物为M1(Cl)p和/或M2(Cl)q,所述p=2m1,q=2m2;
所述第一原料化合物为Y-X1-H、Y’-X1’-H、H-X2-R-CN或H-X4-R’-X3-H中的任意1种或至少2种的组合,所述第一原料化合物中必须含有H-X2-R-CN或H-X4-R’-X3-H中的任意1种,其中,X1、X1’、X2、X3、X4、Y、Y’、R和R’具有与权利要求1~3之一所述的相同含义,R、R’、Y和Y’优选为取代或未取代的苯基,进一步优选为未取代的苯基。
或者,所述第一原料化合物为Y-X1-Na、Y’-X1’-Na、或Na-X4-R’-X3-Na中的任意1种或至少2种的组合,所述第一原料化合物中必须含有或Na-X4-R’-X3-Na中的任意1种,其中,X1、X1’、X2、X3、X4、Y、Y’、R和R’具有与前述X1、X1’、X2、X3、X4、Y、Y’、R和R’相同的含义。
亲核取代可采用本领域公知的方法来制备,例如可参考“聚磷腈的研究进展,张宏伟等,材料导报2010年第24卷第7期”。催化剂的具体实例有氯化锌、氯化镁、氯化铝等金属氯化物、三氟化硼及其络合物、氢氧化钠等路易斯碱。这些催化剂可以一种或多种混合使用,本发明中并无特别的规定。磷腈氯化物可以采用来源最为广泛的六氯环三磷腈等。为得到得到目标产物中的Y-X1-基、Y’-X1’-基、基和-X4-R’-X3-基,可同时加入可提供Y-X1-基、Y’-X1’-基、基和-X4-R’-X3-基的亲核试剂,也可以分别依次加入可提供Y-X1-基、Y’-X1’-基、基和-X4-R’-X3-基的亲核试剂。
在亲核试剂与磷腈氯化物的反应中,可以先采用一种亲核试剂与磷腈氯化物反应,部分取代磷腈氯化物中的氯,然后再用另一种亲核试剂与磷腈氯化物反应,以得到式(Ⅰ)结构的磷腈化合物。并且可以通过控制物质之间的物质量关系,来得到结构中含有一个M基团或含有多个M基团的磷腈化合物。
本发明还提供了一种氰酸酯树脂组合物,包含前述的含氰基的磷腈化合物。
本发明所述氰酸酯树脂具有良好阻燃性、耐热性(耐200℃高温)、良好的粘结性能、良好的机械性能。
至于氰酸酯树脂树脂组合物的氰酸酯树脂、固化剂、其它填料可采用公知的原料。
本发明还提供了一种预浸板,其由所述环氧树脂组合物含浸或涂布于基材而成。
所述基材为玻璃纤维基材、聚酯基材、聚酰亚胺基材、陶瓷基材或碳纤维基材。
这里,其含浸或涂布的具体工艺条件无特别限定。“预浸板”也为本领域技术人员所熟知的“粘结片”。
本发明还提供了一种复合金属基板,其包括一张以上如前所述的预浸板依次进行表面覆金属层、重叠、压合而成。
优选地,所述表面覆金属层的材质为铝、铜、铁及其任意组合的合金。
优选地,所述复合金属基板为CEM-1覆铜板、CEM-3覆铜板、FR-4覆铜板、FR-5覆铜板、CEM-1铝基板、CEM-3铝基板、FR-4铝基板或FR-5铝基板。
本发明还提供了一种线路板,所述线路板于所述的复合金属基板的表面加工线路而成。
本发明还提供了一种柔性覆铜板,所述柔性覆铜板包含一张以上所述预浸板以及覆于叠合后的预浸板一侧或两侧的铜箔。
本发明还提供了一种所述的含氰基的磷腈化合物的用途,所述含氰基的磷腈化合物用于IC封装版、HDI封装版、汽车板或覆铜板。
氰酸酯树脂树脂组合物的原料通过固化在复合金属基板上形成具有良好阻燃性能的涂层,可提高线路板,例如电子产业、电气、电器产业、交通运输、航空航天、玩具产业等需要线路板的机器、设备、仪器、仪表等产业的广泛应用。
上述术语“×××基或基团”指×××化合物分子结构中脱去一个或多个氢原子或其它原子或原子团后剩余的部分。
本发明通过在磷腈基团上引入氰基,实现了与磷腈基团P、N的协同增效,提高了其热稳定性、阻燃型以及与其他组分的配伍性均表现优异,含有本发明所述的磷腈化合物的树脂组合物具有良好的耐热性、耐水性、粘结性和机械性能、电性能,从而扩大了其应用范围。采用本发明提供的磷腈化合物制备得到的环氧树脂,阻燃等级可达到V-0。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。
本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
实施例1
一种磷腈化合物1,具有如下的结构:
制备方法为:
(1)在反应器中,将羟基当量为119g/eq的对氰基苯酚714g(6eq)的溶解在二氧六环中,然后加入氯原子当量为28.4g/eq的六氯环三磷腈170.5g(6eq)和钠原子当量为53g/eq的碳酸钠318g(6eq),通入氮气保护,在回流温度下反应24小时;
(2)将步骤(1)的产物用物理方法去除体系中的盐分、水分,再过滤去除体系中的不溶物质,蒸馏掉体系中溶剂,干燥后得到磷腈化合物1,氰基当量为140.7g/eq。
性能表征:
红外光谱为:1400~1600cm-1(苯环);2220~2230cm-1(氰基);1260~1280cm-1(P-N);1170~1185cm-1(P=N);955~960cm-1、1005~1015cm-1、1065~1075cm-1(P-O-C);另外,510cm-1(P-Cl)峰消失;
1H-NMR(DMSO-d6,ppm)核磁图谱为:6.85~6.95(氰基苯酚基上酚羟基邻位的氢,12H),7.3~7.4(氰基苯酚基上酚羟基间位的氢,12H)。
实施例2
一种磷腈化合物2,具有如下的结构:
制备方法为:
(1)在反应器中,将羟基当量为119g/eq的对氰基苯酚357g(3eq)和羟基当量为94g/eq的苯酚282g(3eq)溶解在二氧六环中,然后加入氯原子当量为28.4g/eq的六氯环三磷腈170.5g(6eq)和钠原子当量为53g/eq的碳酸钠318g(6eq),通入氮气保护,在回流温度下反应24小时;
(2)将步骤(1)的产物经碱洗洗涤,后除去残余原料,干燥后得到磷腈化合物2,其氰基当量为256.2g/eq。
性能表征:
红外光谱为:1400~1600cm-1(苯环);2220~2230cm-1(氰基);1260~1280cm-1(P-N);1170~1185cm-1(P=N);955~960cm-1、1005~1015cm-1、1065~1075cm-1(P-O-C);另外,510cm-1(P-Cl)峰消失;
1H-NMR(DMSO-d6,ppm)核磁图谱为:6.85~6.95(氰基酚羟基上酚羟基邻位的氢,6H),7.3~7.4(氰基酚羟基上氰基邻位的氢,6H),6.73(苯酚基上酚羟基邻位的氢,6H),7.05~7.12(苯酚基上酚羟基间位的氢),6H,6.80~6.84(苯酚基上酚羟基对位的氢,3H)。
实施例3
一种磷腈化合物3,具有如下的结构:
制备方法为:
(1)在反应器中,将羟基当量为119g/eq的对氰基苯酚357g(3eq)和羟基当量为108g/eq的对甲基苯酚324g(3eq)溶解在二氧六环中,然后加入氯原子当量为28.4g/eq的六氯环三磷腈170.5g(6eq)和钠原子当量为53g/eq的碳酸钠318g(6eq),通入氮气保护,在回流温度下反应24小时;
(2)将步骤(1)的产物经碱洗洗涤,后除去残余原料,干燥后得到磷腈化合物3,其氰基当量为270g/eq。
性能表征:
红外光谱为:1400~1600cm-1(苯环);2220~2230cm-1(氰基);1260~1280cm-1(P-N);1170~1185cm-1(P=N);955~960cm-1、1005~1015cm-1、1065~1075cm-1(P-O-C)、2960cm-1、2870cm-1(甲基);另外,510cm-1(P-Cl)峰消失;
1H-NMR(DMSO-d6,ppm)核磁图谱为:6.85~6.95(氰基酚羟基上酚羟基邻位的氢,6H),7.3~7.4(氰基酚羟基上氰基邻位的氢,6H),6.73(苯酚基上酚羟基邻位的氢,6H),7.05~7.12(苯酚基上酚羟基间位的氢,6H),6.80~6.84(苯酚基上酚羟基对位的氢,3H),2.3~2.4(甲基上的氢,9H)。
实施例4
一种磷腈化合物4,具有如下的结构:
制备方法为:
(1)在反应器中,将羟基当量为119g/eq的对氰基苯酚357g(3eq)、羟基当量为108g/eq的对甲基苯酚216g(2eq)和羟基当量为55g/eq的对苯二酚110g(2eq)溶解在二氧六环中,然后加入氯原子当量为28.4g/eq的六氯环三磷腈170.5g(6eq)和钠原子当量为53g/eq的碳酸钠318g(6eq),通入氮气保护,在回流温度下反应24小时;
(2)向步骤(1)的反应产物中加入氯原子当量为28.4g/eq的六氯环三磷腈170.5g(6eq)、羟基当量为108g/eq的对甲基苯酚432g(4eq)、羟基当量为55g/eq的对苯二酚110g(2eq),以及钠原子当量为53g/eq的碳酸钠318g(6eq),通入氮气保护,在回流温度下反应24小时;
(3)向步骤(2)的反应产物中加入氯原子当量为28.4g/eq的六氯环三磷腈170.5g(6eq)、羟基当量为119g/eq的对氰基苯酚357g(3eq)、羟基当量为108g/eq的对甲基苯酚216g(2eq)以及钠原子当量为53g/eq的碳酸钠318g(6eq),通入氮气保护,在回流温度下反应24小时;
(4)将步骤(3)的产物经碱洗洗涤,后除去残余原料,干燥后得到磷腈化合物4,其氰基当量为364.5g/eq。
性能表征:
红外光谱为:1400~1600cm-1(苯环);2220~2230cm-1(氰基);1260~1280cm-1(P-N);1170~1185cm-1(P=N);955~960cm-1、1005~1015cm-1、1065~1075cm-1(P-O-C)、2960cm-1、2870cm-1(甲基);另外,510cm-1(P-Cl)峰消失;
1H-NMR(DMSO-d6,ppm)核磁图谱为:6.85~6.95(氰基酚羟基上酚羟基邻位的氢,20H),7.3~7.4(氰基酚羟基上氰基邻位的氢,20H),6.58~6.63(对甲基苯酚基上羟基邻位的氢,8H),6.85~6.95(对甲基苯酚基上甲基基邻位的氢,8H),2.3~2.4(甲基上的氢,30H)。
应用例1
一种无卤阻燃氰酸酯树脂组合物,按重量份数包括如下组分:
向187g液态双酚A环氧树脂中加入22.5g实施例1得到的磷腈化合物1和88.2g酚羟基当量为105的酚醛树脂,用适当的丙酮溶解成溶液,用标准玻璃纤维布上胶,压合成覆铜板,将此覆铜板命名为覆铜板a。测得覆铜板a的性能如表-1所示。
应用例2
一种无卤阻燃氰酸酯树脂组合物,按重量份数包括如下组分:
向187g液态双酚A环氧树脂中加入25.6g实施例1得到的磷腈化合物1和94.5g酚羟基当量为105的酚醛树脂,用适当的丙酮溶解成溶液,用标准玻璃纤维布上胶,压合成覆铜板,将此覆铜板命名为覆铜板b。测得覆铜板b的性能如表-1所示。
应用例3
一种无卤阻燃氰酸酯树脂组合物,按重量份数包括如下组分:
向187g液态双酚A环氧树脂中加入27g实施例1得到的磷腈化合物1和94.5g酚羟基当量为105的酚醛树脂,得到氰酸酯树脂C,之后用适当的丙酮溶解成溶液,用标准玻璃纤维布上胶,压合成覆铜板,将此覆铜板命名为覆铜板c。测得覆铜板c的性能如表-1所示。
应用例4
一种无卤阻燃氰酸酯树脂组合物,按重量份数包括如下组分:
向187g液态双酚A环氧树脂中加入29.15g实施例1得到的磷腈化合物1和96.6g酚羟基当量为105的酚醛树脂,得到氰酸酯树脂D,之后用适当的丙酮溶解成溶液,用标准玻璃纤维布上胶,压合成覆铜板,将此覆铜板命名为覆铜板d。测得覆铜板d的性能如表-1所示。
比较例1
与应用例1的区别在于,将磷腈化合物1等质量替换为六苯氧基环三磷氰,得到环氧树脂组合物E。
采用环氧树脂组合物E用适当的丙酮溶解成溶液,用标准玻璃纤维布上胶,压合成覆铜板,将此覆铜板命名为覆铜板e。测得覆铜板e的性能如表-1所示。
实施例和比较例的测试结果如下表-1所示:
表-1各种覆铜板的性能比较
测试方法:
(1)吸水率
将100mm×100mm×1.6mm板材置于105℃的烘箱中干燥1h,冷却后称重并放置在105kPa的蒸汽压下蒸煮120min,最后擦干称重并计算出吸水率。
(2)玻璃化转变温度Tg
制备测试样品的宽度约为8-12mm,长度为60mm,在德国耐驰DMA Q800上设置测量模式为弯曲模式,扫描温度为室温至200℃,读取损耗角正切值最大时对应的温度为该试样的玻璃化转变温度Tg。
(3)弯曲强度
制备25.4mm×63.5m的试样,使用游标卡尺测量其厚度,将材料万能试验机的测试模式调为弯曲测试模式,设置间距为15.9mm,试验速度为0.51mm/min,取3次平行测试的平均值,测试温度分别为室温和180℃。
(4)剥离强度测定
将覆铜层叠板切成100mm×3mm的试验片,使用抗剥仪试验装置,以速度50.8mm/min对铜箔进行剥离分层,测试铜箔与树脂的剥离强度,数值越大说明树脂与铜箔间的粘合力越好。
(5)按照标准ANSL UL94-1985测试燃烧性;
(6)按照标准GB 5594.3-1985测试线膨胀系数。
申请人声明,本发明通过上述实施例来说明本发明的工艺方法,但本发明并不局限于上述工艺步骤,即不意味着本发明必须依赖上述工艺步骤才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明所选用原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (10)
1.一种含氰基的磷腈化合物,其特征在于,所述磷腈化合物具有式(I)的结构:
其中,Y和Y’均各自独立地选自有机基团;
M1和M2均各自独立地选自磷腈基团,且M1含有m1个磷原子,M2含有m2个磷原子;
X1、X1’、X2、X3和X4均各自独立地任选为第六主族元素中的任意一种;
R和R’均各自独立地选自亚有机基团;
a为≥0的整数,b为≥1的整数,c为≥0的整数,且满足a+b=2m1,d+2=2m2。
2.如权利要求1所述的磷腈化合物,其特征在于,所述M1和M2均各自独立地选自具有式(II)结构的环状磷腈,或具有式(III)结构的线性磷腈;
在式(II)或式(III)中,n1为≥2的整数,n2为≥1的整数;
优选环三磷腈基、环四磷腈基或非环状聚磷腈基中的任意1种或至少2种的组合;优选环三磷腈基;
优选地,Y和Y’均各自独立地选自取代或未取代的直链烃基、取代或未取代的支链烃基或取代或未取代的芳香基;优选C1~C30的取代或未取代的直链烃基、C1~C30取代或未取代的支链烃基或C6~C30取代或未取代的芳香基;进一步优选C1~C10的取代或未取代的直链烃基、C1~C10取代或未取代的支链烃基或C6~C16取代或未取代的芳香基;特别优选苯基、甲苯基、二甲苯基、乙苯基、甲基、乙基、正丙基、正丁基、异丙基或异丁基;
进一步优选地,Y和Y’均各自独立地为苯基、甲苯基、二甲苯基或乙苯基;
优选地,R和R’均各自独立地选自取代或未取代的直链亚烃基、取代或未取代的支链亚烃基、取代或未取代的亚芳香基;优选C1~C30的取代或未取代的直链亚烃基、C1~C30取代或未取代的支链亚烃基、C6~C30取代或未取代的亚芳香基;进一步优选C1~C10的取代或未取代的直链亚烃基、C1~C10取代或未取代的支链亚烃基、C6~C16取代或未取代的亚芳香基;特别优选亚苯基、甲基亚苯基、二甲基亚苯基、乙基亚苯基、亚甲基、亚乙基、亚丙基、中丙基、亚正丁基或亚异丙基;
进一步优选地,R和R’均各自独立地为亚苯基、甲基亚苯基、二甲基亚苯基、乙基亚苯基或
优选地,X1、X1’、X2、X3和X4均为氧原子。
3.如权利要求1或2所述的磷腈化合物,其特征在于,所述磷腈化合物选自其中,M1、M2、a、b、R、R’具有与权利要求1相同的选择范围;
优选地,所述磷腈化合物选自 其中,M1、M2、a、b具有与权利要求1相同的选择范围;
优选地,所述磷腈化合物选自
4.一种如权利要求1~3之一所述的含氰基的磷腈化合物的制备方法,其特征在于,所述方法包括如下步骤:
将磷腈氯化物与第一原料化合物进行亲核取代反应,得到含氰基的磷腈化合物;
所述磷腈氯化物为M1(Cl)p和/或M2(Cl)q,所述p=2m1,q=2m2;
所述第一原料化合物为Y-X1-H、Y’-X1’-H、H——X2——R——CN或H-X4-R’-X3-H中的任意1种或至少2种的组合,所述第一原料化合物中必须含有H——X2——R——CN或H-X4-R’-X3-H中的任意1种,其中,X1、X1’、X2、X3、X4、Y、Y’、R和R’具有与权利要求1~3之一所述的相同含义,R和Y优选为取代或未取代的苯基,进一步优选为未取代的苯基。
5.一种氰酸酯树脂组合物,其特征在于,包含权利要求1-3之一所述的含氰基的磷腈化合物。
6.一种预浸板,其特征在于,其由如权利要求5所述氰酸酯脂组合物含浸或涂布于基材而成;
优选地,所述基材为玻璃纤维基材、聚酯基材、聚酰亚胺基材、陶瓷基材或碳纤维基材。
7.一种复合金属基板,其特征在于,其包括一张以上如权利要求5所述预浸板依次进行表面覆金属层、重叠、压合而成;
优选地,所述表面覆金属层的材质为铝、铜、铁及其任意组合的合金;
优选地,所述复合金属基板为CEM-1覆铜板、CEM-3覆铜板、FR-4覆铜板、FR-5覆铜板、CEM-1铝基板、CEM-3铝基板、FR-4铝基板或FR-5铝基板。
8.一种线路板,其特征在于,于权利要求7所述的复合金属基板的表面加工线路而成。
9.一种柔性覆铜板,其特征在于,所述柔性覆铜板包含一张以上如权利要求6所述预浸板以及覆于叠合后的预浸板一侧或两侧的铜箔。
10.一种如权利要求1-3之一所述的含氰基的磷腈化合物的用途,其特征在于,所述含氰基的磷腈化合物用于IC封装版、HDI封装版、汽车板或覆铜板。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610012162.6A CN106946937A (zh) | 2016-01-07 | 2016-01-07 | 一种含氰基的磷腈化合物、制备方法和用途 |
JP2016148875A JP2017122077A (ja) | 2016-01-07 | 2016-07-28 | シアノ基を含むホスファゼン化合物、製造方法及び用途 |
EP16182165.7A EP3190119A1 (en) | 2016-01-07 | 2016-08-01 | Phosphazene compound comprising cyano group, preparation method and uses thereof |
TW105125211A TWI585098B (zh) | 2016-01-07 | 2016-08-08 | 一種含氰基的磷腈化合物、製備方法及用途 |
US15/234,004 US20170197998A1 (en) | 2016-01-07 | 2016-08-11 | Phosphazene compound comprising cyano group, preparation method and uses thereof |
KR1020160135279A KR20170082967A (ko) | 2016-01-07 | 2016-10-18 | 시아노기를 함유한 포스파젠화합물, 제조방법 및 용도 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610012162.6A CN106946937A (zh) | 2016-01-07 | 2016-01-07 | 一种含氰基的磷腈化合物、制备方法和用途 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN106946937A true CN106946937A (zh) | 2017-07-14 |
Family
ID=56842610
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201610012162.6A Pending CN106946937A (zh) | 2016-01-07 | 2016-01-07 | 一种含氰基的磷腈化合物、制备方法和用途 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20170197998A1 (zh) |
EP (1) | EP3190119A1 (zh) |
JP (1) | JP2017122077A (zh) |
KR (1) | KR20170082967A (zh) |
CN (1) | CN106946937A (zh) |
TW (1) | TWI585098B (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107522744A (zh) * | 2016-06-21 | 2017-12-29 | 广东广山新材料股份有限公司 | 一种磷腈化合物、磷腈环氧树脂、预浸板及复合金属基板 |
CN107602617A (zh) * | 2016-07-12 | 2018-01-19 | 广东广山新材料股份有限公司 | 含有氰基的磷腈化合物、制备方法及用途 |
CN109970981A (zh) * | 2017-12-27 | 2019-07-05 | 华为技术有限公司 | 一种固体阻燃聚合物、电极片、隔膜和锂二次电池 |
CN111269266A (zh) * | 2020-04-01 | 2020-06-12 | 吉林大学 | 含氰基芳醚磷腈型无卤阻燃剂、制备方法及辐照交联电缆绝缘材料中的应用 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6830586B1 (ja) * | 2020-07-22 | 2021-02-17 | 株式会社伏見製薬所 | オキサホスホリン環含有構造を有する環状ホスファゼン化合物 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1242784A (zh) * | 1997-10-15 | 2000-01-26 | 大塚化学株式会社 | 交联苯氧基磷腈化合物、阻燃剂、阻燃性树脂组合物和阻燃性树脂成形体 |
JP2007224160A (ja) * | 2006-02-23 | 2007-09-06 | Matsushita Electric Works Ltd | 難燃剤 |
JP2009191252A (ja) * | 2008-01-17 | 2009-08-27 | Toyo Ink Mfg Co Ltd | 難燃性樹脂組成物 |
JP2010189589A (ja) * | 2009-02-20 | 2010-09-02 | Toyo Ink Mfg Co Ltd | 硬化性難燃性電磁波シールド接着フィルム |
JP2011162615A (ja) * | 2010-02-05 | 2011-08-25 | Kyocera Chemical Corp | プリプレグおよび金属張り積層板 |
CN102741352A (zh) * | 2010-01-28 | 2012-10-17 | 三井化学株式会社 | 金属树脂复合体 |
CN103709747A (zh) * | 2013-12-27 | 2014-04-09 | 广东生益科技股份有限公司 | 一种热固性树脂组合物及其用途 |
CN105153234A (zh) * | 2014-06-13 | 2015-12-16 | 广东生益科技股份有限公司 | 一种苯氧基环三磷腈活性酯、无卤树脂组合物及其用途 |
CN106103591A (zh) * | 2014-03-06 | 2016-11-09 | 三菱瓦斯化学株式会社 | 树脂组合物、预浸料、树脂片、覆金属箔层叠板及印刷电路板 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002114981A (ja) * | 1997-02-14 | 2002-04-16 | Otsuka Chem Co Ltd | 難燃剤、難燃性樹脂組成物及び難燃性樹脂成形体 |
JP2011094037A (ja) * | 2009-10-30 | 2011-05-12 | Toyo Ink Mfg Co Ltd | 難燃性接着剤組成物、難燃性接着剤シート、及びフレキシブルプリント配線板 |
-
2016
- 2016-01-07 CN CN201610012162.6A patent/CN106946937A/zh active Pending
- 2016-07-28 JP JP2016148875A patent/JP2017122077A/ja active Pending
- 2016-08-01 EP EP16182165.7A patent/EP3190119A1/en not_active Withdrawn
- 2016-08-08 TW TW105125211A patent/TWI585098B/zh active
- 2016-08-11 US US15/234,004 patent/US20170197998A1/en not_active Abandoned
- 2016-10-18 KR KR1020160135279A patent/KR20170082967A/ko not_active Application Discontinuation
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1242784A (zh) * | 1997-10-15 | 2000-01-26 | 大塚化学株式会社 | 交联苯氧基磷腈化合物、阻燃剂、阻燃性树脂组合物和阻燃性树脂成形体 |
JP2007224160A (ja) * | 2006-02-23 | 2007-09-06 | Matsushita Electric Works Ltd | 難燃剤 |
JP2009191252A (ja) * | 2008-01-17 | 2009-08-27 | Toyo Ink Mfg Co Ltd | 難燃性樹脂組成物 |
JP2010189589A (ja) * | 2009-02-20 | 2010-09-02 | Toyo Ink Mfg Co Ltd | 硬化性難燃性電磁波シールド接着フィルム |
CN102741352A (zh) * | 2010-01-28 | 2012-10-17 | 三井化学株式会社 | 金属树脂复合体 |
JP2011162615A (ja) * | 2010-02-05 | 2011-08-25 | Kyocera Chemical Corp | プリプレグおよび金属張り積層板 |
CN103709747A (zh) * | 2013-12-27 | 2014-04-09 | 广东生益科技股份有限公司 | 一种热固性树脂组合物及其用途 |
CN106103591A (zh) * | 2014-03-06 | 2016-11-09 | 三菱瓦斯化学株式会社 | 树脂组合物、预浸料、树脂片、覆金属箔层叠板及印刷电路板 |
CN105153234A (zh) * | 2014-06-13 | 2015-12-16 | 广东生益科技股份有限公司 | 一种苯氧基环三磷腈活性酯、无卤树脂组合物及其用途 |
Non-Patent Citations (1)
Title |
---|
CABINO A. CARRIEDO等: "On the Synthesis of Functionalized Cyclic and Polymeric Aryloxyphosphazenes from Phenols", 《J. APP. POLYMER SCI.》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107522744A (zh) * | 2016-06-21 | 2017-12-29 | 广东广山新材料股份有限公司 | 一种磷腈化合物、磷腈环氧树脂、预浸板及复合金属基板 |
CN107602617A (zh) * | 2016-07-12 | 2018-01-19 | 广东广山新材料股份有限公司 | 含有氰基的磷腈化合物、制备方法及用途 |
CN109970981A (zh) * | 2017-12-27 | 2019-07-05 | 华为技术有限公司 | 一种固体阻燃聚合物、电极片、隔膜和锂二次电池 |
CN111269266A (zh) * | 2020-04-01 | 2020-06-12 | 吉林大学 | 含氰基芳醚磷腈型无卤阻燃剂、制备方法及辐照交联电缆绝缘材料中的应用 |
CN111269266B (zh) * | 2020-04-01 | 2021-11-16 | 吉林大学 | 含氰基芳醚磷腈型无卤阻燃剂、制备方法及辐照交联电缆绝缘材料中的应用 |
Also Published As
Publication number | Publication date |
---|---|
TW201808975A (zh) | 2018-03-16 |
KR20170082967A (ko) | 2017-07-17 |
TWI585098B (zh) | 2017-06-01 |
EP3190119A1 (en) | 2017-07-12 |
US20170197998A1 (en) | 2017-07-13 |
JP2017122077A (ja) | 2017-07-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101915918B1 (ko) | 열경화성 수지 조성물 및 이로 제조한 프리프레그와 적층판 | |
CN106946937A (zh) | 一种含氰基的磷腈化合物、制备方法和用途 | |
CN107177030B (zh) | 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 | |
EP2896653B1 (en) | Epoxy resin composition, and, prepreg and copper clad laminate manufactured using the composition | |
CN108250676B (zh) | 一种含磷活性酯及其无卤组合物与覆铜箔基板 | |
CN105348742B (zh) | 含三聚氰胺型苯并噁嗪树脂的热固性树脂组合物、半固化片及层压板 | |
CN107337694A (zh) | 一种带硅醇的磷腈化合物、阻燃剂、环氧树脂组合物以及复合金属基板 | |
KR101915919B1 (ko) | 열경화성 수지 조성물 및 이로 제조한 프리프레그와 적층판 | |
TWI656129B (zh) | 一種含有酯基的磷腈化合物、製備方法及用途 | |
JP2017110014A (ja) | Dopo誘導体とエポキシ樹脂組成物の高周波基板への適用 | |
CN108148178A (zh) | 一种热固性树脂组合物 | |
EP3187501B1 (en) | A phosphazene compound, and a composition, a prepreg and a wiring board comprising the same | |
TWI617614B (zh) | Epoxy resin composition and prepreg and copper clad laminate prepared using same | |
CN108164684A (zh) | 一种热固性树脂组合物 | |
CN108219114B (zh) | 一种无卤热固性树脂组合物、含有它的预浸料、层压板以及印制线路板 | |
CN104892899A (zh) | 带双酚f基磷氮环氧树脂、阻燃组合物、复合金属基板 | |
CN112409572A (zh) | 含磷阻燃低热膨胀系数环氧树脂及其制备方法和所涉及的中间产物以及应用 | |
CN108250674A (zh) | 一种无卤环氧树脂组合物以及使用它的预浸料和层压板 | |
CN107602617A (zh) | 含有氰基的磷腈化合物、制备方法及用途 | |
CN104371321B (zh) | 一种热固性树脂组合物及用其制作的预浸料与层压板 | |
CN104371320B (zh) | 一种热固性树脂组合物及用其制作的预浸料与层压板 | |
CN115716972A (zh) | 无卤低介电组成物、积层板以及印刷电路板 | |
CN107540712A (zh) | 一种改性磷腈化合物、制备方法及用途 | |
CN107540713A (zh) | 一种改性的低介电磷腈化合物、制备方法及用途 | |
CN107573487A (zh) | 含巯基磷腈化合物、固化剂和含巯基磷腈环氧树脂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170714 |