Benzoxazines and compositions containing the same

Patent metadata

Field	Value
Publication number	US-9499666-B2
Application number	US-201313848220-A
Country	US
Kind code	B2
Filing date	Mar 21, 2013
Priority date	Mar 29, 2012
Publication date	Nov 22, 2016
Grant date	Nov 22, 2016

Abstract

Disclosed herein are monofunctional benzoxazine compounds having at least one electron-withdrawing group. The monofunctional benzoxazine compounds may be combined with one or more multifunctional benzoxazine compounds to form a unique benzoxazine blend. This benzoxazine blend may be combined with additional components such as catalysts and toughening agents to form a curable resin composition suitable for forming resinous films or composite materials. The presence of monofunctional benzoxazine improves the processability of the benzoxazine-based resin composition by reducing the viscosity of the resin composition, and results in improved tack and drape in the films and composite materials formed from the composition without the loss of modulus in the cured resin.

First claim

What is claimed is:

1. A curable composition comprising:
(a) at least one substituted monofunctional benzoxazine compound, which is in liquid form at ambient temperature within the range of 20° C.-25° C. and is represented by one of the following structures:

wherein X is F in structure (A), and is F or Cl in structures (B) and (C); and
(b) at least one multifunctional benzoxazine compound.

2. The curable composition of claim 1 , wherein the weight ratio of multifunctional benzoxazine to substituted monofunctional benzoxazine is within the range of 99.9:0.1 to 50:50.

3. The curable composition of claim 2 , wherein the multifunctional benzoxazine compound is a di-functional benzoxazine.

4. The of claim 2 , wherein the multifunctional benzoxazine compound is a compound of Formula (II):

wherein:
Z 1 is selected from a direct bond, —C(R 3 )(R 4 )—, —C(R 3 )(aryl)-, —C(O)—, —S—, —O—, —S(O)—, —S(O) 2 —, a divalent heterocycle and —[C(R 3 )(R 4 )] x -arylene-[C(R 5 )(R 6 )] y —, or the two benzyl rings of the benzoxazine moieties may be fused;
R 1 and R 2 are independently selected from alkyl, cycloalkyl and aryl;
R 3 , R 4 , R 5 and R 6 are independently selected from H, C 1-8 alkyl and halogenated alkyl;
x and y are independently 0 or 1.

5. The curable composition of claim 4 , wherein Z 1 is —[C(R 3 )(R 4 )] x -arylene-[C(R 5 )(R 6 )] y .

6. The curable composition of claim 4 , wherein Z 1 is selected from —C(CH 3 ) 2 —, —CH 2 — and 3,3-isobenzofuran-1(3H)-one.

7. The curable composition of claim 4 , wherein R 1 and R 2 in Formula II are independently selected from aryl.

8. The curable composition of claim 1 further comprising:
at least one thermoplastic or elastomeric toughening agent.

9. The curable composition of claim 1 further comprising:
a catalyst for activating the curing of the benzoxazine compounds.

10. A cured resin formed from curing the curable composition of claim 1 within the range of 180° C.-200° C.

11. A composite material comprising reinforcement fibers impregnated with the curable composition of claim 1 .

12. A prepreg comprising a layer of unilaterally aligned reinforcement fibers impregnated with the curable composition of claim 1 .

13. A composite part formed by infusing a dry fiber preform having a three-dimensional shape with the curable composition of claim 1 , followed by curing.

14. The curable composition of claim 1 , wherein the substituted monofunctional benzoxazine compound is represented by structure (B) and the composition further comprises an isomer represented by structure (D):

wherein X is the same for both structures (B) and (D).

15. The curable composition of claim 1 , wherein the composition does not contain any solvent.

Assignees

• Cytec Tech Corp

Inventors

• Ward Steven
• Harriman Mark

Classifications

• C08G59/00

  Polycondensates containing more than one epoxy group per molecule (low-molecular-weight polyepoxy compounds C07); Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups · CPC title

• C08L61/34

  Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20 · CPC title

• C07D265/16 Primary

  with only hydrogen or carbon atoms directly attached in positions 2 and 4 · CPC title

• C08L79/02

  Polyamines · CPC title

• C08G73/0233 Primary

  Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups · CPC title