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CN-122003455-A - Maleimide polymers for electronic laminates

CN122003455ACN 122003455 ACN122003455 ACN 122003455ACN-122003455-A

Abstract

Provided herein are compounds of formula (I), wherein X is selected from the group consisting of bond, carbonyl, methylene, C 2 to C 20 alkanediyl, and C 2 to C 20 alkenediyl, Y is selected from the group consisting of C 2 to C 20 alkanediyl, a moiety of formula (Y 1 ), a moiety of formula (Y 2 ), a moiety of formula (Y 3 ), a group of formula (Y 4 ), and a moiety of formula (Y 5 ), R 1 –R 6 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl, and alkoxy, and n is an integer greater than or equal to 1. The compounds exhibit good solubility, high thermal stability and good dielectric properties and are useful, for example, in the preparation of electronic laminate compositions.

Inventors

  • YE SIYU
  • BAO JIANLE

Assignees

  • 蓝立方知识产权有限责任公司

Dates

Publication Date
20260508
Application Date
20230831

Claims (16)

  1. 1. A compound of the formula I, Wherein the method comprises the steps of X is selected from the group consisting of bond, carbonyl, methylene, C 2 to C 20 alkanediyl, and C 2 to C 20 alkenediyl; Y is selected from the group consisting of C 2 to C 20 alkanediyl, a moiety of formula Y 1 , Y-type 1 A moiety of the formula Y 2 , Y-type 2 A moiety of the formula Y 3 , Y-type 3 Part of Y 4 Y-type 4 A moiety of formula Y 5 ; y-type 5 R 1 –R 6 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl, and alkoxy, and N is an integer greater than or equal to 1.
  2. 2. The compound of claim 1, wherein X is an alkanediyl group having from 2 carbon atoms to about 10 carbon atoms.
  3. 3. The compound of claim 1, wherein X is an alkenediyl group having from 2 carbon atoms to about 10 carbon atoms.
  4. 4. The compound of claim 1, wherein Y is an alkanediyl group having from 2 carbon atoms to about 10 carbon atoms.
  5. 5. The compound of claim 1, wherein each R 1 –R 6 is independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, vinyl, propenyl, butenyl, phenyl, naphthyl, methoxy, ethoxy, propoxy, and butoxy.
  6. 6. The compound according to any one of claims 1 to 5, wherein n is greater than 1.
  7. 7. A process for preparing a compound as claimed in any one of claims 1 to 6, which comprises reacting a polyalkene with a bismaleimide in a liquid reaction medium.
  8. 8. The method of claim 7, wherein the liquid reaction medium comprises an organic solvent.
  9. 9. The method of claim 7, wherein the liquid reaction medium comprises an organic solvent selected from the group consisting of diglyme, propylene glycol monomethyl ether acetate, 1,3, 5-trimethylbenzene, xylene, and methyl isobutyl ketone.
  10. 10. The method of claim 7, wherein the liquid reaction medium comprises diglyme.
  11. 11. The method of any one of claims 7 to 10, wherein the temperature of the liquid reaction medium is maintained at least about 110 ℃ during the reaction.
  12. 12. The method of claim 11, wherein the temperature of the liquid reaction medium is maintained at about 120 ℃ to about 160 ℃ during the reaction.
  13. 13. A curable composition comprising: a compound according to any one of claims 1 to 6 at a concentration of at least about 20% by weight of the composition, and A crosslinking component comprising at least one crosslinking agent at a concentration of from about 10% to about 80% by weight of the composition.
  14. 14. The composition of claim 13, wherein the crosslinking component comprises at least one crosslinking agent selected from the group consisting of triallyl isocyanurate, polyalkene, cyanate, poly (p-phenylene oxide), and polybutadiene.
  15. 15. The composition of claim 13 or 14, further comprising zinc dioctanoate at a concentration of from about 0.1% to about 1% by weight of the composition.
  16. 16. A printed circuit board comprising the curable composition of any one of claims 13 to 15.

Description

Maleimide polymers for electronic laminates Background Bismaleimides (BMIs) are thermosetting resins that can be used in high temperature applications due to their thermal stability and relatively good dielectric properties. Thus, the BMI can be used for both industrial electronics and consumer electronics. For example, BMI can be used in electronic laminate applications that require resistance to high temperatures and low losses (i.e., the level of energy dissipation or attenuation that occurs as electromagnetic waves or signals pass through a material). In addition, BMI is less costly than polyphenylene ether (e.g., SA9000 from Sabic), a common component in electronic laminate applications. Traditionally, conventional BMI has been used in electronic lamination processes. Conventional BMI is commonly used as a base material for high performance thermosetting resins. However, commercially available BMIs (e.g., 4 '-diphenylmethane bismaleimide, 3' -dimethyl-5, 5 '-diethyl-4, 4' -diphenylmethane bismaleimide) have poor solubility in ketones (i.e., typically less than 20% at 25 ℃) and poor viscosity build-up (viscibility build-up) during the pre-cure step of the electronic laminate formation process. Thus, the percentage of BMI in a formulation is typically small. Accordingly, there is a need for improved compounds and processes, including maleimide polymers with good solubility, high thermal stability, and good dielectric properties. Summary of The Invention For example, provided herein is a compound of formula I, I is a kind of Wherein the method comprises the steps of X is selected from the group consisting of bond, carbonyl, methylene, C 2 to C 20 alkanediyl, and C 2 to C 20 alkenediyl; Y is selected from the group consisting of C 2 to C 20 alkanediyl, a moiety of formula Y 1, Y-type 1 A moiety of the formula Y 2, Y-type 2 A moiety of the formula Y 3, Y-type 3 Part of Y 4 Y-type 4 A moiety of formula Y 5; y-type 5 R 1–R6 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl, and alkoxy, and N is an integer greater than or equal to 1. Also provided herein are methods of preparing a compound of formula I, comprising reacting a polyalkene with a bismaleimide in a liquid reaction medium. Preferably, the liquid reaction medium comprises an organic solvent, such as diglyme. Also provided herein are curable compositions comprising compounds of formula I. For example, the curable composition can be used to prepare electronic laminates such as printed circuit boards. The curable composition may further comprise one or more optional components, such as a crosslinking component, a free radical initiator, and a crosslinking catalyst. Also provided are printed circuit boards comprising the curable resin compositions provided herein (e.g., curable resin compositions comprising a compound of formula I). Other objects and features will be in part apparent and in part pointed out hereinafter. Detailed Description Provided herein are compounds useful in electronic laminate compositions that have good solubility, high thermal stability, and good dielectric properties. For example, provided herein are maleimide polymers prepared from a polyalkene and BMI by Diels-Alder reaction. The compounds disclosed herein may exhibit higher solubility in Methyl Ethyl Ketone (MEK) than prior art compositions while also providing low loss performance characteristics suitable for use in electronic laminates. Preferably, the compounds provided herein are fluorine-free (and more preferably, halogen-free). For example, the compounds can be used to prepare fluorine-free (and more preferably, halogen-free) electronic laminate compositions. Definition of the definition As used herein, the term "alkyl" refers to a straight or branched chain moiety comprising up to about 10 carbon atoms (unless a different number of carbon atoms is specified otherwise). Non-limiting examples of 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). As used herein, the term "aryl" refers to a moiety derived by removal of one hydrogen atom from a ring carbon atom of an aromatic hydrocarbon. Non-limiting examples of aryl groups include phenyl, o-tolyl, p-tolyl, and naphthyl. As used herein, the term "alkoxy" refers to a moiety of the form ‒ OR ', wherein R' is alkyl as defined herein. For example, the group ‒ OCH 3 may be referred to herein as "methoxy". The group ‒ OCH 2CH3 may be referred to herein as "ethoxy". Non-limiting examples of alkoxy groups include methoxy, ethoxy, and propoxy. The alkoxy group may comprise a straight chain alkyl group or a branched chain alkyl group (e.g., isopropoxy). As used herein, the term "alkenyl" refers to a straight or branched chain moiety comprising up to about 10 carbon atoms (unless a different number of carbon atoms is specified otherwise) and comprising at least one double bond b