US3975330A
Expired / Lapsed
US
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Imide-modified polyester resin and wire enamel containing the imide-modified polyester resin
Assignee: Nitto Denko Corp
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Filing: 1975-04-18
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Granted: 1976-08-17
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Expires: 1995-04-18
Abstract
Abstract An imide-ring containing polyester comprising the reaction product of (A) (1) a dicarboxylic acid of the formula ##EQU1## wherein R 1 represents a divalent organic group, R 2 represents a trivalent organic group, and n≧1, the dicarboxylic acid of the formula (I) comprising the reaction product of 1 mole of an imide compound having terminal amino groups of the formula (II) ##EQU2## wherein R 1 has the same meaning as above, or of an imide precursor thereof, with 2 moles of a tricarboxylic acid anhydride of the formula (III) ##EQU3## wherein R 2 has the same meaning as above, the imide compound of the formula (II) being prepared by reacting n moles of 1,2,3,4-butanetetracarboxylic acid (hereinafter referred to as BTC) with (n+1) moles of a diamine of the formula (IV) h.sub.2 n--r.sub.1 --nh.sub.2 (iv) wherein R 1 has the same meaning as above; or (A) (2) a mixture of the dicarboxylic acid of the formula (I) with at least one other polycarboxylic acid (including the lower alkyl ester thereof) with (B) at least one polyhydric alcohol; and a wire enamel containing the imide ring containing polyester described above.
Inventors
- 👤 Yasuhiro Suzuki
- 👤 Katsuhiko Yamaguchi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 14:52
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/16; H; H01; H01B; H01B3/00; H01B3/18; H01B3/30; H01B3/303; H01B3/306
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
186 words
An imide-modified polyester resin comprising the reaction product of (A) (1) a dicarboxylic acid of the formula (I) ##EQU4## wherein R 1 represents a divalent organic group; R 2 represents a trivalent aromatic organic group and n≧1, or (A) (2) a mixture of at least about 5% by weight of said dicarboxylic acid of the formula (I) with up to about 95% by weight of at least one other polycarboxylic acid or the lower alkyl ester thereof; with (B) a polyhydric alcohol; said dicarboxylic acid of the formula (I) comprising the reaction product of 1 mole of an imide compound having terminal amino groups of the formula (II) ##EQU5## wherein R 1 has the same meaning as above, or of an imide precursor thereof, with 2 moles of a tricarboxylic acid anhydride of the formula (III) ##EQU6## wherein R 2 has the same meaning as above, said imide compopund of the formula (II) comprising the reaction product of n moles of 1,2,3,4-butanetetracarboxylic acid with (n+1) moles of a diamine of the formula (IV) h.sub.2 n--r.sub.1 --nh.sub.2 (iv) wherein R 1 has the same meaning as above.
Claim 2
Dependent Claim
186 words
An imide-modified polyester resin comprising the reaction product of (A) (1) a dicarboxylic acid of the formula (I) ##EQU4## wherein R 1 represents a divalent organic group; R 2 represents a trivalent aromatic organic group and n≧1, or (A) (2) a mixture of at least about 5% by weight of said dicarboxylic acid of the formula (I) with up to about 95% by weight of at least one other polycarboxylic acid or the lower alkyl ester thereof; with (B) a polyhydric alcohol; said dicarboxylic acid of the formula (I) comprising the reaction product of 1 mole of an imide compound having terminal amino groups of the formula (II) ##EQU5## wherein R 1 has the same meaning as above, or of an imide precursor thereof, with 2 moles of a tricarboxylic acid anhydride of the formula (III) ##EQU6## wherein R 2 has the same meaning as above, said imide compopund of the formula (II) comprising the reaction product of n moles of 1,2,3,4-butanetetracarboxylic acid with (n+1) moles of a diamine of the formula (IV) h.sub.2 n--r.sub.1 --nh.sub.2 (iv) wherein R 1 has the same meaning as above.
Claim 3
Dependent Claim
37 words
The imide-modified polyester resin as claimed in claim 1, wherein said imide compound of the formula (II) comprises the reaction product of said 1,2,3,4-butanetetracarboxylic acid and said diamine in an aromatic solvent or in a nitrogen-containing solvent.
Claim 4
Dependent Claim
40 words
The imide-modified polyester resin as claimed in claim 2, wherein said dicarboxylic acid of the formula (I) and said imide compound of the formula (II) both comprise the reaction product obtained at a temperature ranging from about 60° to 230°C.
Claim 5
Dependent Claim
15 words
The imide-modified polyester resin as claimed in claim 1, wherein n is 1 to 5.
Claim 6
Dependent Claim
26 words
The imide-modified polyester resin as claimed in claim 1, wherein R 1 represents a divalent aliphatic group, a divalent alicyclic group or a divalent aromatic group.
Claim 7
Dependent Claim
78 words
The imide-modified polyester resin as claimed in claim 5, wherein R 1 is selected from the group consisting of ##STR7## wherein n 1 is an integer of from 1 to 11; ##SPC5## wherein R 3 is selected from the group consisting of --H, --Cl, --Br, --OCH 3 , --CH 3 and --C 2 H 5 ; and ##SPC6## wherein R 4 is selected from the group consisting of --CH 2 --, --O--, --S--, --SO 2 --, --CO--, ##STR8##
Claim 8
Dependent Claim
16 words
The imide-modified polyester resin as claimed in claim 1, wherein said diamine is an aromatic diamine.
Claim 9
Dependent Claim
47 words
The imide-modified polyester resin as claimed in claim 1, wherein said diamine is ethylenediamine, m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 4,4'-diaminodiphenylpropane, 4,4'-diaminodiphenylether, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfide, benzidine, 3,3'-dichloroobenzidine, 3,3'-dimethylbenzidine, p-bis(4-aminophenoxy)-benzene, 1,5-diaminonaphthalene, 2,6-diaminonaphthalene, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,4'-diaminobenzanilide, 3,3'-dimethoxybenzidine, 3,4'-diaminodiphenylether, m-xylylenediamine, p-xylylenediamine, di(p-aminocyclohexyl)methane, 4,4'-diaminophenylketone, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, 4,4'-dimethylheptamethylenediamine, 3-methoxyheptamethylenediamine, 2,11-diaminododecane, 1,4-diaminocyclohexane, or 2,6-diaminopyridine.
Claim 10
Dependent Claim
38 words
The imide-modified polyester resin as claimed in claim 1, wherein R 2 represents a trivalent aromatic group having 6 or more carbon atoms, with two bonds of the three bonds of R 2 being positioned adjacent each other.
Claim 11
Dependent Claim
37 words
The imide-modified polyester resin as claimed in claim 9, wherein R 2 is selected from the group consisting of ##SPC7## and ##SPC8## wherein R 5 represents --CH 2 --, --O--, --S--, --SO 2 --, --CO--, or ##STR9##
Claim 12
Dependent Claim
54 words
The imide-modified polyester resin as claimed in claim 11, wherein said tricarboxylic acid anhydride is trimellitic anhydride, hemimellitic anhydride, 3,4,3' (or 3,4,4')-biphenyltricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylmethanetricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylethertricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylsulfidetricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylsulfonetricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylketonetricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylpropanetricarboxylic anhydride, or 2,3,6 (or 2,3,5 or 1,2,4)-naphthalenetricarboxylic anhydride.
Claim 13
Dependent Claim
69 words
The imide-modified polyester resin as claimed in claim 1, wherein said imide-modified polyester resin comprises the reaction product of said imide ring containing dicarboxylic acid (I) esterified with at least one other polycarboxylic acid or the lower alkyl ester thereof selected from the group consisting of terephthalic acid, dimethyl terephthalate, diethylterephthalate, isophthalic acid, dimethyl isophthalate, diethyl isophthalate, 1,4-naphthalene dicarboxylic acid, 1,5-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, or adipic acid.
Claim 14
Dependent Claim
25 words
The imide-modified polyester resin as claimed in claim 12, wherein said esterification reaction product is obtained at a temperature ranging from about 100° to 270°C.
Claim 15
Dependent Claim
35 words
The imide-modified polyester resin as claimed in claim 12, wherein said esterification reaction product is obtained in the absence of a solvent, in the presence of a solvent, or is carried out under reduced pressure.
Claim 16
Dependent Claim
50 words
The imide-modified polyester resin as claimed in claim 12, wherein the esterification reaction product is obtained in the presence of antimony trioxide, zinc acetate, lead acetate, cadmium acetate or manganese acetate as a catalyst and said polycarboxylic acid or the lower alkyl ester thereof is dimethyl terephthalate or dimethyl isophthalate.
Claim 17
Dependent Claim
24 words
The imide-modified polyester resin as claimed in claim 1, wherein said polyhydric alcohol is a dihydric alcohol, a trihydric alcohol or a tetrahydric alcohol.
Claim 18
Dependent Claim
35 words
The imide-modified polyester resin as claimed in claim 16, wherein said polyhydric alcohol is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1-methylpropylene glycol, neopentyl glycol, 1,6-hexanediol, glycerin, trimethylol propane, tris(2-hydroxyethyl)-isocyanurate or pentaerythritol.
Claim 19
Dependent Claim
194 words
A wire enamel containing the imide-modified polyester resin of claim 1 comprising the reaction product of (A) (1) a dicarboxylic acid of the formula (I) ##STR10## wherien R 1 represents a divalent organic group, R 2 represents a trivalent organic group, and n≧1, or (A) (2) a mixture of at least about 5% by weight of said dicarboxylic acid of the formula (I) with up to about 95% by weight of at least one other polycarboxylic acid or the lower alkyl ester thereof, with (B) a polyhydric alcohol; said dicarboxylic acid of the formula (I) comprising the reaction product of 1 mole of an imide compound having terminal amino groups of the formula (II) ##STR11## wherein R 1 has the same meaning as above, or of an imide precursor thereof, with 2 moles of tricarboxylic acid anhydride of the formula (III) ##STR12## wherein R 2 has the same meaning as above, said imide compound of the formula (II) comprising the reaction product of n moles of 1,2,3,4-butanetetracarboxylic acid with (n+1) moles of a diamine of the formula (IV) h.sub.2 n -- r.sub.1 -- nh.sub.2 (iv) wherein R 1 has the same meaning as above.
Claim 20
Dependent Claim
36 words
The wire enamel as claimed in claim 18, wherein said imide compound of the formula (II) comprises the reaction product of said 1,2,3,4-butanetetracarboxylic acid and said diamine in an aromatic solvent or in a nitrogen-containing solvent.
Claim 21
Dependent Claim
39 words
The wire enamel as claimed in claim 19, wherein said dicarboxylic acid of the formula (I) and said imide compound of the formula (II) both comprise the reaction product obtained at a temperature ranging from about 60° to 230°C.
Claim 22
Dependent Claim
14 words
The wire enamel as claimed in claim 18, wherein n is 1 to 5.
Claim 23
Dependent Claim
25 words
The wire enamel as claimed in claim 18, wherein R 1 reppresents a divalent aliphatic group, a divalent alicyclic group or a divalent aromatic group.
Claim 24
Dependent Claim
78 words
The wire enamel as claimed in claim 21, wherein R 1 is selected from the group consisting of ##STR13## wherein n 1 is an integer of from 1 to 11; ##SPC9## ##SPC10## wherein R 3 is selected from the group consisting of --H, --Cl, --Br, --OCH 3 , --CH 3 and --C 2 H 5 ; and ##SPC11## wherein R 4 is selected from the group consisting of --CH 2 --, --O--, --S--, --SO 2 --, --CO--, ##STR14##
Claim 25
Dependent Claim
15 words
The wire enamel as claimed in claim 18, wherein said diamine is an aromatic diamine.
Claim 26
Dependent Claim
46 words
The wire enamel as claimed in claim 18, wherein said diamine is ethylenediamine, m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylethane, 4,4'-diaminodiphenylpropane, 4,4'-diaminodiphenylether, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfide, benzidine, 3,3'-dichlorobenzidine, 3,3'-dimethylbenzidine, p-bis(4-aminophenoxy)benzene, 1,5-diaminonaphthalene, 2,6-diaminonaphthalene, 3,3'-dimethyl-4,4'-diaminobiphenyl, 3,4'-diaminobenzanilide, 3,3'-dimethoxybenzidine, 3,4'-diaminodiphenylether, m-xylylenediamine, p-xylylenediamine, di(p-aminocyclohexyl)methane, 4,4'-diaminophenylketone, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, 4,4'-dimethylheptamethylenediamine, 3-methoxyheptamethylenediamine, 2,11-diaminododecane, 1,4-diaminocyclohexane, or 2,6-diaminopyridine.
Claim 27
Dependent Claim
37 words
The wire enamel as claimed in claim 17, wherein R 2 represents a trivalent aromatic group having 6 or more carbon atoms, with two bonds of the three bonds of R 2 being positioned adjacent each other.
Claim 28
Dependent Claim
34 words
The wire enamel as claimed in claim 26, wherein R 2 is selected from the group consisting of ##SPC12## wherein R 5 represents --CH 2 --, --O--, --S--, --SO 2 --, --CO-- or ##STR15##
Claim 29
Dependent Claim
53 words
The wire enamel as claimed in claim 18, wherein said tricarboxylic acid anhydride is trimellitic anhydride, hemimellitic anhydride, 3,4,3' (or 3,4,4')-biphenyltricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylmethanetricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylethertricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylsulfidetricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylsulfonetricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylketonetricarboxylic anhydride, 3,4,3' (or 3,4,4')-diphenylpropanetricarboxylic anhydride, or 2,3,6 (or 2,3,5 or 1,2,4)-naphthalenetricarboxylic anhydride.
Claim 30
Dependent Claim
68 words
The wire enamel as claimed in claim 18, wherein said imide-modified polyester resin comprises the reaction product of said imide ring containing dicarboxylic acid (I) esterified with at least one other polycarboxylic acid or the lower alkyl ester thereof selected from the group consisting of terephthalic acid, dimethyl terephthalate, diethylterephthalate, isophthalic acid, dimethyl isophthalate, diethyl isophthalate, 1,4-naphthalene dicarboxylic acid, 1,5-naphthalene dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, or adipic acid.
Claim 31
Dependent Claim
24 words
The wire enamel as claimed in claim 29, wherein said esterification reaction product is obtained at a temperature ranging from about 100° to 270°C.
Claim 32
Dependent Claim
34 words
The wire enamel as claimed in claim 29, wherein said esterification reaction product is obtained in the absence of a solvent, in the presence of a solvent, or is carried out under reduced pressure.
Claim 33
Dependent Claim
49 words
The wire enamel as claimed in claim 29, wherein the esterification reaction product is obtained in the presence of antimony trioxide, zinc acetate, lead acetate, cadmium acetate or manganese acetate as a catalyst and said polycarboxylic acid or the lower alkyl ester thereof is dimethyl terephthalate or dimethyl isophthalate.
Claim 34
Dependent Claim
13 words
The wire enamel as claimed in claim 18, including an organo-metal compound hardener.
Claim 35
Dependent Claim
19 words
The wire enamel as claimed in claim 33, including a metal octenoate or metal naphthenate as a hardening accelerator.
Claim 36
Dependent Claim
26 words
The wire enamel as claimed in claim 18, including at least one of a phenol resin, a melamine resin, an epoxy resin or a blocked polyisocyanate.
Claim 37
Dependent Claim
23 words
The wire enamel as claimed in claim 18, wherein said polyhydric alcohol is a dihydric alcohol, a trihydric alcohol or a tetrahydric alcohol.
Claim 38
Dependent Claim
34 words
The wire enamel as claimed in claim 36, wherein said polyhydric alcohol is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1-methylpropylene glycol, neopentyl glycol, 1,6-hexanediol, glycerin, trimethylol propane, tris(2-hydroxyethyl)isocyanurate or pentaerythritol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-17 | 1980-02-16 | 1980-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-17 | 1984-02-16 | 1984-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-17 | 1988-02-16 | 1988-08-17 | $7700.00 | Window Closed / Lapsed |