# US 2025/0084199 A1 · Allyl-type flame-retardant prepolymer, resin composition, composite resin, prepreg and laminate

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- Number: US 2025/0084199 A1
- Document ID: US20250084199A1
- Status: Published application
- Kind: A1
- Application number: 18/724,998
- Filed: 2022-12-29
- Published: 2025-03-13
- Earliest claimed: 2021-12-31
- Assignees: Guangdong Hinno-Tech Co., Ltd.; Research Institute of Tsinghua, Pearl River Delta
- Applicants: Guangdong Hinno-Tech Co., Ltd.; Research Institute of Tsinghua, Pearl River Delta
- Inventors: Xiaolong QI; Wenyan WEN; Yangjie ZHU
- Web page: https://patentgrep.com/patent/US20250084199A1

## CPC

- C08F 226/06: by a heterocyclic ring containing nitrogen
- C08J 5/24: Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- B32B 5/02: characterised by structural features of a {fibrous or filamentary} layer {(layer formed of metallic wires B32B15/02; layer formed of natural mineral fibres B32B19/02; layer formed of wood fibres B32B21/02)}
- B32B 5/26: another layer {next to it} also being fibrous or filamentary {(relative arrangement of fibres or filaments of different layers B32B5/12)}
- B32B 15/14: next to a fibrous or filamentary layer
- B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)}
- B32B 27/08: of synthetic resin
- B32B 27/28: comprising synthetic resins not wholly covered by any one of the sub-groups {B32B27/30 - B32B27/42}
- C08F 212/34: Monomers containing two or more unsaturated aliphatic radicals
- C08J 5/244: {using glass fibres}
- C08J 5/249: {characterised by the additives used in the prepolymer mixture}
- C08L 79/02: Polyamines
- C08L 79/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L 79/085: {Unsaturated polyimide precursors}
- B32B 2260/023: Two or more layers
- B32B 2260/046: Synthetic resin
- B32B 2307/204: Di-electric
- B32B 2307/3065: Flame resistant or retardant, fire resistant or retardant
- B32B 2457/08: PCBs, i.e. printed circuit boards
- C08F 230/02: containing phosphorus
- C08F 2800/20: as weight or mass percentages
- C08J 2335/00: Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Derivatives of such polymers
- C08J 2439/04: Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08J 2463/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J 2475/00: Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08L 2201/02: Flame or fire retardant/resistant
- C08L 2205/035: containing four or more polymers in a blend
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present application discloses an allyl-type flame-retardant prepolymer, a resin composition, a composite resin, a prepreg, and a laminate. The allyl-type flame-retardant prepolymer provided in the present application is prepared by pre-polymerization of an allyl-type benzoxazine compound and an allyl-type phosphorous compound in a mass part ratio of 100:(20 to 80).

## Claims

### Claim 1

An allyl-type flame-retardant prepolymer, comprising 100 mass parts of an allyl-type benzoxazine compound and 20 to 80 mass parts of an allyl-type phosphorous compound;
wherein the allyl-type phosphorous compound has the following structural formula:
the allyl-type benzoxazine compound is selected from the compounds of the following structural formulas and combinations thereof:
wherein X is independently selected from —CHR1—, —CR2R3—, —SO2—, or —O—;
R1, R2, and R3 are each independently selected from —H or —CH3.

### Claim 2 (depends on 1)

The allyl-type flame-retardant prepolymer of claim 1, wherein the allyl-type benzoxazine compound has the following structural formula:

### Claim 3 (depends on 1)

The allyl-type flame-retardant prepolymer of claim 1, further comprising 10 to 20 mass parts of an allyl-type non-phosphorus compound, wherein the allyl-type non-phosphorus compound is selected from allyl-type bisphenol A, allyl-type bisphenol S, allyl-type diphenyl ether, and combinations thereof.

### Claim 4 (depends on 1)

The allyl-type flame-retardant prepolymer of claim 1, wherein the allyl-type flame-retardant prepolymer is prepared by mixing the allyl-type benzoxazine compound with the allyl-type phosphorous compound and then heating them at 100 to 130° C. for 1 to 3 hours.

### Claim 5 (depends on 1, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100)

A resin composition, comprising 10 to 30 mass parts of the allyl-type flame-retardant prepolymer of claim 1, 50 to 100 mass parts of a bismaleimide resin, 30 to 80 mass parts of a cyanate resin, 5 to 30 mass parts of an additional functional resin, and 10 to 60 mass parts of an inorganic filler.

### Claim 6 (depends on 5)

The resin composition of claim 5, wherein the bismaleimide resin is selected from an organic compound containing two or more maleimide structures in the molecular structure thereof; and/or
the cyanate resin is selected from a bisphenol A-type cyanate resin, a phenolic aldehyde-type cyanate resin, a bisphenol F-type cyanate resin, a multifunctional cyanate resin, a bisphenol M-type cyanate resin, a bisphenol E-type cyanate resin, a dicyclopentadiene bisphenol-type cyanate resin, and combinations thereof; and/or
the additional functional resin is selected from an epoxy resin, polyphenyl ether, a hydrocarbon resin, and combinations thereof; and/or
the inorganic filler is selected from zirconium vanadate, zirconium tungstate, hafnium tungstate, microcrystalline glass, eucryptite, silica, quartz, mica powder, titanium dioxide, magnesium oxide, magnesium hydroxide, talc, alumina, silicon carbide, boron nitride, aluminum nitride, molybdenum oxide, barium sulfate, zinc molybdate, zinc borate, zinc stannate, zinc oxide, strontium titanate, barium titanate, calcium titanate, clay, kaolinite, and combinations thereof.

### Claim 7 (depends on 5)

The resin composition of claim 5, further comprising 1 to 5 mass parts of an auxiliary agent selected from a curing accelerator, a coupling agent, a toughening agent, and combinations thereof.

### Claim 8 (depends on 1)

A composite resin, comprising the allyl-type flame-retardant prepolymer of claim 1.

### Claim 9 (depends on 1)

A prepreg, comprising a reinforcing material and a resin material loaded on the reinforcing material, wherein the resin material comprising the allyl-type flame-retardant prepolymer of claim 1.

### Claim 10 (depends on 1)

A laminate, prepared from 9 a prepreg, wherein the prepreg comprising a reinforcing material and a resin material loaded on the reinforcing material, wherein the resin material comprising the allyl-type flame-retardant prepolymer of claim 1.

### Claim 11 (depends on 1, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100)

A composite resin, comprising a resin composition comprising 10 to 30 mass parts of the allyl-type flame-retardant prepolymer of claim 1, 50 to 100 mass parts of a bismaleimide resin, 30 to 80 mass parts of a cyanate resin, 5 to 30 mass parts of an additional functional resin, and 10 to 60 mass parts of an inorganic filler.

### Claim 12 (depends on 1, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100)

A prepreg, comprising a reinforcing material and a resin material loaded on the reinforcing material, wherein the resin material comprising a resin composition comprising 10 to 30 mass parts of the allyl-type flame-retardant prepolymer of claim 1, 50 to 100 mass parts of a bismaleimide resin, 30 to 80 mass parts of a cyanate resin, 5 to 30 mass parts of an additional functional resin, and 10 to 60 mass parts of an inorganic filler.

### Claim 13 (depends on 1, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100)

A laminate, prepared from a prepreg, wherein the prepreg comprising a reinforcing material and a resin material loaded on the reinforcing material, wherein the resin material comprising a resin composition comprising 10 to 30 mass parts of the allyl-type flame-retardant prepolymer of claim 1, 50 to 100 mass parts of a bismaleimide resin, 30 to 80 mass parts of a cyanate resin, 5 to 30 mass parts of an additional functional resin, and 10 to 60 mass parts of an inorganic filler.

### Claim 14 (depends on 1)

The allyl-type flame-retardant prepolymer of claim 1, wherein the allyl groups in the allyl-type benzoxazine compound and the allyl-type phosphorous compound are bonded to each other.

### Claim 15 (depends on 1)

The allyl-type flame-retardant prepolymer of claim 1, wherein a mass ratio the allyl-type benzoxazine compound to the allyl-type phosphorous compound is 100:(40 to 60).

### Claim 16 (depends on 6)

The resin composition of claim 6, wherein the bismaleimide resin is selected from N-phenylmaleimide resin, N-(2-methylphenyl)maleimide resin, N-(4-methylphenyl)maleimide resin, N-(2,6-dimethylphenyl)maleimide resin, bis(4-maleimidophenyl)methane resin, 2,2-bis(4-(4-maleimidophenoxy)-phenyl)propane resin, bis(3,5-dimethyl-4-maleimidophenyl)methane resin, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane resin, bis(3,5-diethyl-4-maleimidophenyl)methane resin, polyphenylmethanebismaleimide resin, biphenyl-containing maleimide resin, and combinations thereof.