EP0283636A2
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EP
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Polyetherimide oligomers and blends
Assignee: Boeing Co
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Filing: 1988-01-05
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Granted: —
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Expires: 2008-01-05
Abstract
Abstract Polyetherimide oligomers having crosslinking end cap moieties which provide improved solvent -resistance to cured composites are generally represented by the formula: E = allyl or methallyl; R = a trivalent C (6-13) aromatic organic radical; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-. Blends generally comprise substantially equimolar amounts of the oligomers and a comparable, compatible, noncrosslinking, etherimide polymer of substantially the same backbone. The crosslinkable oligomers are made by reacting substituted phthalic anhydrides with hydroxyaryl amines and suitable crosslinking end cap reactants, or by self-condensation of phthalimide salts followed by capping the polymers. Related polyetherimides of the present invention can be prepared by the condensation of nitrophthalic anhydride, diamines, dialcohols, (dihydricphenols), and phenolic, crosslinking end caps (A-OH), or the condensation of bis(phenates) or dialcohols (bisphenols), diamines, nitrophthalic anhydride, and amine-terminated end caps (A-NH₂) or nitro-terminated end caps (A-NO₂). The oligomers and blends can be prepregged, and can be cured to form advanced composites having aerospace applications.
Inventors
- 👤 Hyman R. Lubowitz
- 👤 Clyde H. Sheppard
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 09:54
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C08G73/1003; C08G73/1007; C08G73/101; C08G73/1057; C08G73/1064; C08G73/1067; C08J; C08J5/00; C08J5/24; C08L; C08L79/00; C08L79/04; C08L79/08; C08J2379/00; C08J2379/04; C08J2379/08; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31721
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
96 words
Polyetherimide oligomers, comprising the product of the process of reacting: in about the stoichiometric ratio of I:II:III:IV = 1:1:m:m, wherein m is an integer greater than or equal to one, the reaction product having the general formula: wherein X = -O- or -S-; E = allyl or methallyl; Y = halo- or nitro- R = a trivalent C (6-13) aromatic organic radical; R₁= any of lower alkyl, lower alkoxy, aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2,; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 2
Dependent Claim
96 words
Polyetherimide oligomers, comprising the product of the process of reacting: in about the stoichiometric ratio of I:II:III:IV = 1:1:m:m, wherein m is an integer greater than or equal to one, the reaction product having the general formula: wherein X = -O- or -S-; E = allyl or methallyl; Y = halo- or nitro- R = a trivalent C (6-13) aromatic organic radical; R₁= any of lower alkyl, lower alkoxy, aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2,; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 3
Dependent Claim
54 words
A blend of polyetherimide oligomers and polyetherimide polymers, comprising substantially equimolar amounts of an oligomer of claim 1 and a polymer having a compatible backbone absent the crosslinking end cap radicals (A) of the oligomer, the polymer including repeating units of the formula: wherein X, R, and Rʹ are as defined in claim 1.
Claim 4
Dependent Claim
12 words
A prepreg comprising a suitable reinforcement and the oligomer of claim 1.
Claim 5
Dependent Claim
12 words
A prepreg comprising a suitable reinforcement and the blend of claim 2.
Claim 6
Dependent Claim
11 words
A cured composite formed by curing the prepreg of claim 3.
Claim 7
Dependent Claim
11 words
A cured composite formed by curing the prepreg of claim 4.
Claim 8
Dependent Claim
11 words
A cured composite formed by curing the oligomer of claim 1.
Claim 9
Dependent Claim
11 words
A cured composite formed by curing the blend of claim 2.
Claim 10
Independent Claim
110 words
A method of synthesizing a polyetherimide oligomer, comprising the step of reacting: in about the ratio of about I:II:III:IV = 1:1:m:m, wherein m is an integer greater than or equal to one, the reaction product having the general formula: wherein R = a trivalent C (6-13) aromatic organic radical; X = -O- or -S-; E = allyl or methallyl; Y = halo- or nitro- R₁ = any of lower alkyl, lower alkoxyl aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂, the reaction occurring in a suitable solvent under an inert atmosphere.
Claim 11
Independent Claim
110 words
A method of synthesizing a polyetherimide oligomer, comprising the step of reacting: in about the ratio of about I:II:III:IV = 1:1:m:m, wherein m is an integer greater than or equal to one, the reaction product having the general formula: wherein R = a trivalent C (6-13) aromatic organic radical; X = -O- or -S-; E = allyl or methallyl; Y = halo- or nitro- R₁ = any of lower alkyl, lower alkoxyl aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂, the reaction occurring in a suitable solvent under an inert atmosphere.
Claim 12
Dependent Claim
67 words
An anhydride of the formula: wherein X = -O- or -S-; R = a trivalent C (6-13) aromatic organic radical; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; j = 0, 1, or 2 and G = -CH₂-, -O-, -S-, or -SO₂-, the anhydride being formed by reacting A-XH with a substituted phthalic anhydride of the formula: wherein Y = halo- or nitro-.
Claim 13
Dependent Claim
67 words
An anhydride of the formula: wherein X = -O- or -S-; R = a trivalent C (6-13) aromatic organic radical; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; j = 0, 1, or 2 and G = -CH₂-, -O-, -S-, or -SO₂-, the anhydride being formed by reacting A-XH with a substituted phthalic anhydride of the formula: wherein Y = halo- or nitro-.
Claim 14
Dependent Claim
67 words
A compound of the formula: wherein R = a trivalent C (6-13) aromatic organic radical; E = allyl or methallyl; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-, the compound being formed by reacting A-NH₂ with a substituted phthalic anhydride of the formula: wherein Y = halo- or nitro-.
Claim 15
Dependent Claim
67 words
A compound of the formula: wherein R = a trivalent C (6-13) aromatic organic radical; E = allyl or methallyl; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-, the compound being formed by reacting A-NH₂ with a substituted phthalic anhydride of the formula: wherein Y = halo- or nitro-.
Claim 16
Dependent Claim
60 words
Polyetherimide oligomers of the general formula: E = allyl or methallyl; Y = halo- or nitro-; R₂ = a trivalent C (6-13) aromatic organic radical; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 17
Dependent Claim
60 words
Polyetherimide oligomers of the general formula: E = allyl or methallyl; Y = halo- or nitro-; R₂ = a trivalent C (6-13) aromatic organic radical; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 18
Dependent Claim
85 words
Polyetherimide oligomers prepared by the process of reacting a polyetherimide polymer made by the self-condensation of a phthalimide salt of the formula: with crosslinking end cap moieties of the formulae: E = allyl or methallyl; Y = halo- or nitro- R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2; G = -CH₂-, -O-, -S-, or -SO₂-; and M = an alkali metal ion, ammonium salt, or hydrogen.
Claim 19
Dependent Claim
85 words
Polyetherimide oligomers prepared by the process of reacting a polyetherimide polymer made by the self-condensation of a phthalimide salt of the formula: with crosslinking end cap moieties of the formulae: E = allyl or methallyl; Y = halo- or nitro- R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; Rʹ = a divalent C (6-30) aromatic organic radical; j = 0, 1, or 2; G = -CH₂-, -O-, -S-, or -SO₂-; and M = an alkali metal ion, ammonium salt, or hydrogen.
Claim 20
Independent Claim
102 words
A method of making polyetherimide oligomers comprising the step of: condensing a mixture of about 2m + 2 moles of nitrophthalic anhydride of the formula: with about m + 1 moles of diamine, about m moles of dialcohol, and about 2 moles of A-OH, wherein A = n = 1 or 2; m = an integer greater than or equal to 1; E = allyl or methallyl; R = a trivalent C (6-13) aromatic organic radical; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl: j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 21
Independent Claim
102 words
A method of making polyetherimide oligomers comprising the step of: condensing a mixture of about 2m + 2 moles of nitrophthalic anhydride of the formula: with about m + 1 moles of diamine, about m moles of dialcohol, and about 2 moles of A-OH, wherein A = n = 1 or 2; m = an integer greater than or equal to 1; E = allyl or methallyl; R = a trivalent C (6-13) aromatic organic radical; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl: j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 22
Dependent Claim
13 words
The polyetherimide oligomer that is the product of the process of claim 14.
Claim 23
Independent Claim
84 words
A method for making polyetherimide oligomers comprising the step of: condensing about 2 m + 2 moles of nitrophthalic anhydride with about m+1 moles of dialcohol, about m moles of diamine, and about 2 moles of A-NH₂, wherein: n = 1 or 2; m = an integer greater than or equal to 1; E = allyl or methallyl; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 24
Independent Claim
84 words
A method for making polyetherimide oligomers comprising the step of: condensing about 2 m + 2 moles of nitrophthalic anhydride with about m+1 moles of dialcohol, about m moles of diamine, and about 2 moles of A-NH₂, wherein: n = 1 or 2; m = an integer greater than or equal to 1; E = allyl or methallyl; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 25
Dependent Claim
13 words
The polyetherimide oligomer that is the product of the process of claim 16.
Claim 26
Independent Claim
80 words
A method for making polyetherimide oligomers comprising the steps of: condensing about 2m moles of nitrophthalic anhydride with about m+1 moles of dialcohol, about m moles of diamine, and about 2 moles of A-NO₂, wherein: n = 1 or 2; m = an integer greater than or equal to 1; E= allyl or methallyl; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 27
Independent Claim
80 words
A method for making polyetherimide oligomers comprising the steps of: condensing about 2m moles of nitrophthalic anhydride with about m+1 moles of dialcohol, about m moles of diamine, and about 2 moles of A-NO₂, wherein: n = 1 or 2; m = an integer greater than or equal to 1; E= allyl or methallyl; R₁ = any of lower alkyl, lower alkoxy, aryl, or substituted aryl; j = 0, 1, or 2; and G = -CH₂-, -O-, -S-, or -SO₂-.
Claim 28
Dependent Claim
13 words
The polyetherimide oligomers that is the product of the process of claim 18.
Claim 29
Dependent Claim
97 words
The polysulfoneimide oligomers comprising the product of the process of reacting: m+1 moles of a dianhydride; m moles of a diamine; and 2 moles of an amine end cap, the oligomer having the general formula: wherein R and Rʹ are divalent aromatic organic radicals having from 2-20 carbon atoms. These radicals include halogenated aromatic C (6-20) hydrocarbon derivatives; alkylene radicals and cycloalkylene radicals having from 2-20 carbon atoms; C (2-8) alkylene terminated polydiorganosiloxanes; and radicals of the formula: wherein q = -C y H 2y -, -CO-, -SO₂-, -O-, or -S-; and y = 1 to 5.
Claim 30
Dependent Claim
97 words
The polysulfoneimide oligomers comprising the product of the process of reacting: m+1 moles of a dianhydride; m moles of a diamine; and 2 moles of an amine end cap, the oligomer having the general formula: wherein R and Rʹ are divalent aromatic organic radicals having from 2-20 carbon atoms. These radicals include halogenated aromatic C (6-20) hydrocarbon derivatives; alkylene radicals and cycloalkylene radicals having from 2-20 carbon atoms; C (2-8) alkylene terminated polydiorganosiloxanes; and radicals of the formula: wherein q = -C y H 2y -, -CO-, -SO₂-, -O-, or -S-; and y = 1 to 5.
References Cited (Backward Citations)
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