# US 2015/0147508 A1 · Halogen-Free Benzoxazine Based Curable Compositions for High Tg Applications

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- Number: US 2015/0147508 A1
- Document ID: US20150147508A1
- Status: Published application
- Kind: A1
- Application number: 14/606,481
- Filed: 2015-01-27
- Published: 2015-05-28
- Earliest claimed: 2008-02-21
- Assignees: Huntsman Advanced Materials Americas LLC
- Applicants: Huntsman Advanced Materials Americas LLC
- Inventors: Roger Tietze; Yen-Loan Nguyen
- Web page: https://patentgrep.com/patent/US20150147508A1

## CPC

- C08L 79/04: Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- B29C 65/02: by heating, with or without pressure
- B29D 22/003: {Containers for packaging, storing or transporting, e.g. bottles, jars, cans, barrels, tanks}
- C08G 59/24: carbocyclic
- C08G 59/4014: {Nitrogen containing compounds}
- C08G 59/5046: {heterocyclic}
- C08G 59/621: {Phenols}
- C08G 59/683: {Phenolates}
- C08K 5/357: Six-membered rings
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 75/04: Polyurethanes
- B29K 2079/00: Use of polymers having nitrogen, with or without oxygen or carbon only, in the main chain {, not provided for in groups B29K2061/00 - B29K2077/00}, as moulding material
- C08G 59/06: of polyhydric phenols
- C08G 73/0233: {Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups}
- C08G 2650/36: Pre-polymer
- C08L 75/08: from polyethers
- Y10T 428/1397: Single layer [continuous layer]
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A method for forming a halogen-free curable composition containing a benzoxazine monomer, at least one epoxy resin, a catalyst, a toughening agent and a solvent. The halogen-free curable composition is especially suited for use in automobile and aerospace applications since the composition, upon curing, produces a composite having a high glass transition temperature.

## Claims

### Claim 1

A method for producing a halogen-free curable composition comprising mixing together:
(a) a benzoxazine monomer of the formula (I)
wherein each R is, independently from one another, allyl, unsubstituted or substituted phenyl, unsubstituted or substituted C1-C8-alkyl or unsubstituted or substituted C3-C8 cycloalkyl;
(b) at least one epoxy resin;
(c) 5.7-10 parts by weight per 100 parts by weight of the composition of a catalyst selected from tetraphenolethane;
(d) 5.7-10 parts by weight per 100 parts by weight of a toughening agent of the formula (II)
wherein m is 1 or 2, n is 2 to 6, R0 is an n-valent radical of an elastomeric prepolymer after the removal of the terminal isocyanate, amino or hydroxyl groups, the elastomeric prepolymer being soluble or dispersible in epoxy resin, X and Y independently of one another are —O— or —NR3—, at least one X or Y being —NR3—, R2 is an m+1-valent radical of polyphenol or aminophenol after the removal of the phenolic hydroxyl group(s) and optionally of the amino group, and R3 is hydrogen, C1-C6 alkyl or phenol; and
(e) a solvent
to produce the halogen-free curable composition.

### Claim 2 (depends on 1)

The method of claim 1 further comprising mixing in at least one of reinforcement fibers, micro or hollow spheres, plasticizers, carbon black, graphite, dyestuffs, or metal powders.

### Claim 3 (depends on 1)

A halogen-free curable composition produced according to the method of claim 1.

### Claim 4

A method of forming an article comprising:
(a) applying on a first substrate a halogen-free curable composition comprising
(i) a benzoxazine monomer of the formula (I)
wherein each R is, independently from one another, allyl, unsubstituted or substituted phenyl, unsubstituted or substituted C1-C8-alkyl or unsubstituted or substituted C3-C8 cycloalkyl;
(ii) at least one epoxy resin;
(iii) 5.7-10 parts by weight per 100 parts by weight of the composition of a catalyst selected from tetraphenolethane;
(iv) 5.7-10 parts by weight per 100 parts by weight of a toughening agent of the formula (II)
wherein m is 1 or 2, n is 2 to 6, R0 is an n-valent radical of an elastomeric prepolymer after the removal of the terminal isocyanate, amino or hydroxyl groups, the elastomeric prepolymer being soluble or dispersible in epoxy resin, X and Y independently of one another are —O— or —NR3—, at least one X or Y being —NR3—, R2 is an m+1-valent radical of polyphenol or aminophenol after the removal of the phenolic hydroxyl group(s) and optionally of the amino group, and R3 is hydrogen, C1-C6 alkyl or phenol; and
(v) a solvent;
(b) adjoining a second substrate to the first substrate; and
(c) heating the halogen-free curable composition and substrates at a temperature greater than 150° C. to adhere the substrates together and form the article.

### Claim 5

A container comprising a halogen-free curable composition wherein the halogen-free curable composition comprises
(a) a benzoxazine monomer of the formula (I)
wherein each R is, independently from one another, allyl, unsubstituted or substituted phenyl, unsubstituted or substituted C1-C8-alkyl or unsubstituted or substituted C3-C8 cycloalkyl;
(b) at least one epoxy resin;
(c) 5.7-10 parts by weight per 100 parts by weight of the composition of a catalyst selected from tetraphenolethane;
(d) 5.7-10 parts by weight per 100 parts by weight of a toughening agent of the formula
wherein m is 1 or 2, n is 2 to 6, R0 is an n-valent radical of an elastomeric prepolymer after the removal of the terminal isocyanate, amino or hydroxyl groups, the elastomeric prepolymer being soluble or dispersible in epoxy resin, X and Y independently of one another are —O— or —NR3—, at least one X or Y being —NR3—, R2 is an m+1-valent radical of polyphenol or aminophenol after the removal of the phenolic hydroxyl group(s) and optionally of the amino group, and R3 is hydrogen, C1-C6 alkyl or phenol; and
(e) a solvent.