Polyester oligomer
AssigneeThe Boeing Company
InventorsHyman R. Lubowitz, Clyde H. Sheppard
Life of this patent
Estimating the term…
Abstract
High performance polyester sulfone oligomers are prepared for aerospace applications by condensing mono- or difunctional crosslinkable end caps (i.e. unsaturated hydrocarbons having one or two crosslinking sites) with dicarboxylic acid halides and dialcohols (i.e. diols). Multidimensional oligomers have an aromatic hub from which the polyester chains radiate. Blends of the linear and multidimensional oligomers can be made using compatible, non-crosslinking polymers. Prepregs and composites are formed from the oligomers or blends.
Claims42
A linear polyester oligomer useful for forming advanced composites, comprising:
- wherein the polyester oligomer is formed by the simultaneous condensation of diacid halides, dialcohols, and end-cap monomers and wherein
- E is a crosslinkable end cap radical to improve the solvent resistance of the cured oligomer in the advanced composite and is:
- R1 is lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;
- j is 0, 1, or 2;
- G is —CH2—, —O—, —S—, or —SO2—;
- T is methallyl or allyl;
- Me is methyl;
- A is a residue of a dicarboxylic acid halide;
- and
- B is a residue of a dialcohol.
An oligomer useful for forming advanced composites, comprising the product of the process of reacting about:
- (a) 2 moles of a crosslinkable end cap acid halide of the general formula:
- Di—Ø—COX, wherein
- Ø is phenyl;
- D is
- X is halogen;
- i is 1 or 2;
- R1 is lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;
- j is 0, 1, or 2;
- G is —CH2—, —O—, —S—, or —SO2—;
- T is methallyl or allyl;
- and
- Me is methyl;
- (b) n moles of a dicarboxylic acid halide or of a chain including a plurality of aryl rings linked with at least one linkage selected from the group consisting of —SO2—, —O—, —S—, —CO—, —(CH3)2C—, —(CF3)2C—, and mixtures thereof throughout the chain, the chain having an acid halide functionality on each end;
- and
- (c) (n+1) moles of a diol having terminal —OH functionalities, wherein n is an integer greater than or equal to 1.
A linear polyester oligomer useful for forming advanced composites, comprising:
- wherein the polyester oligomer is formed by the simultaneous condensation of diacid halides, dialcohols, and end-cap monomers and wherein
- E is a crosslinkable end cap radical to improve the solvent resistance of the cured oligomer in the advanced composite and is:
- R1 is lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;
- j is 0, 1, or 2;
- G is —CH2—, —O—, —S—, or —SO2—;
- T is methallyl or allyl;
- Me is methyl;
- A is a residue of a dicarboxylic acid halide;
- B is a residue of a dialcohol;
- wherein both A and B are linear aromatic radicals having a plurality of aromatic groups linked together by linkages selected from the group consisting of:
- —CO—;
- —O—;
- —S—;
- —SO2—;
- —(CH3)2C—;
- —(CF3)2C—;
- —CH═N—;
- oxazole;
- thiazole;
- and imidazole;
- wherein the aromatic groups of both A and B are selected from the group consisting of phenyl, biphenyl, naphthyl, and mixtures thereof;
- wherein A includes a radical of the general formula:
- wherein D is:
- —SO2—, —S—, —CO—, —O—, —(CH3)2C—, —(CF3)2C—, or mixtures thereof, and
- wherein B includes one or more linkages selected from the group consisting of —CH═N oxazole, thiazole, and imidazole.
An oligomer useful for forming advanced composites, comprising the product of the process of reacting about:
- (a) 2 moles of a crosslinkable end cap phenol of the general formula:
- Di—Ø—OH,
- (b) (n+1) moles of a dicarboxylic acid halide/or of a chain including a plurality of aryl rings linked with at least one linkage selected from the group consisting of —SO2—, —O—, —S—, —CO—, —(CH3)2C—, —(CF3)2C—, and mixtures thereof throughout the chain, the chain having an acid halide functionality on each end;
- and
- (c) n moles of a diol having terminal —OH functionalities,
- wherein the diol, the diacid halide, or both includes a Schiff base segment being one of:
- R1 is lower alkyl, lower alkoxy, aryl, aryloxy, substituted alkyl, substituted aryl, halogen, or mixtures thereof;
- j is 0, 1, or 2;
- G is —CH2—, —O—, —S—, or —SO2—;
- T is methallyl for allyl;
- Me is methyl;
- R is phenyl;
- biphenyl;
- naphthyl;
- or a compound of the general formula:
- —Ø—W—Ø—
- W is —CH2— or —SO2—;
- and
- q is 0-4.
Dependencies are inferred from the claim text.