Back to results
US 2023/0265247 A1Published application
Process for preparing polyimides
AssigneeTechnische UniversitäT Wien
InventorsMiriam Margarethe UNTERLASS, Daniel Alonso CERRON-INFANTES
Life of this patent
Estimating the term…
Abstract
The invention relates to a stoichiometric salt of a tetracarboxylic acid and a diamine of the following general formula (I), wherein R1 is selected from tetravalent residues of butane, cyclobutane, cyclopentane, cyclohexane, tetrahydrofurane and benzophenone and R2 is selected from divalent residues of unbranched, branched or cyclic aliphatic hydrocarbons with 3 to 15 carbon atoms, with the proviso that the salt of the formula (I) is water-soluble and is selected from compounds (1) to (28); and to the polyimides prepared from these salts by polycondensation.
Claims10
A stoichiometric salt of a tetracarboxylic acid and a diamine of the following general formula (I):
- wherein R1 is selected from tetravalent residues of butane, cyclobutane, cyclopentane, cyclohexane, tetrahydrofuran and benzophenone and R2 is selected from divalent residues of straight, branched or cyclic aliphatic hydrocarbons having from 3 to 15 carbon atoms,
- wherein
- i) the salt of formula (I) is water-soluble;
- and
- ii) it is selected from the following compounds:
- a) Salts of tetrahydrofuran-2,3,4,5-tetracarboxylic acid with aliphatic diamines
- Propane-1,3 -diammonium-dihydrogen-tetrahydrofuran-2,3,4,5 -tetracarboxylate (1),
- Butane-1,4-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (2),
- Pentane-1,5-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (3),
- 2,2-Dimethylpropane-1,3-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (4),
- Hexane-1,6-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5 -tetracarboxylate (5),
- 2-Methylpentane-1,5-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (6),
- Heptane-1,7-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (7),
- Octane-1,8-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (8),
- Nonane-1,9-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (9);
- b) Salts of tetrahydrofuran-2,3,4,5-tetracarboxylic acid with alicyclic diamines
- Cyclohexane-1,2-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (10),
- Cyclohexane-1,3 -diammonium-dihydrogen-tetrahydrofuran-2,3,4,5 -tetracarboxylate (11),
- Cyclohexane-1,4-diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (12),
- Cyclohexane-1,3-bis(methanammonium)-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (13),
- Cyclohexane-1,4-bis(methanammonium)-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (14),
- Norbornane bis(methylammonium)-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (15),
- Isophorone diammonium-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (16),
- Tricyclo[5.2.1.02,6]decane-3(4),8(9)-bis(methanammonium)-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (17),
- 4,4′-Methylene-bis(2-methylcyclohexylammonium)-dihydrogen-tetrahydrofuran-2,3,4,5-tetracarboxylate (18);
- c) Salts of 1,2,3,4-butanetetracarboxylic acid with alicyclic diamines
- Norbornane bis(methylammonium)-dihydrogen-1,2,3,4-butanetetracarboxylate (19),
- Tricyclo[5.2.1.02,6]decane-3(4),8(9)-bis(methanammonium)-dihydrogen-1,2,3,4-butanetetracarboxylate (20);
- d) Salts of 1,2,3,4-cyclobutanetetracarboxylic acid with alicyclic diamines
- Norbornane bis(methylammonium)-dihydrogen-1,2,3,4-cyclobutanetetracarboxylate (21),
- Tricyclo[5.2.1.02,6]decane-3(4),8(9)-bis(methanammonium)-dihydrogen-1,2,3,4-cyclobutanetetracarboxylate (22);
- e) Salts of 1,2,3,4-cyclopentanetetracarboxylic acid with alicyclic diamines
- Norbornane bis(methylammonium)-dihydrogen-1,2,3,4-cyclopentanetetracarboxylate (23),
- Tricyclo[5.2.1.02,6]decane-3(4),8(9)-bis(methanammonium)-dihydrogen-1,2,3,4-cyclopentanetetracarboxylate (24);
- f) Salts of 1,2,4,5-cyclohexanetetracarboxylic acid with alicyclic diamines
- Norbornane bis(methylammonium)-dihydrogen-1,2,4,5-cyclohexanetetracarboxylate (25),
- Tricyclo[5.2.1.02,6]decane-3(4),8(9)-bis(methanammonium)-dihydrogen-1,2,4,5-cyclohexane tetracarboxylate (26);
- and
- g) Salts of 3,3′,4,4′-benzophenonetetracarboxylic acid with alicyclic diamines
- Norbornane bis(methylammonium)-dihydrogen-3,3′,4,4′-benzophenone-tetracarboxylate (27),
- Tricyclo[5.2.1.02,6]decane-3 (4), 8(9)-bis(methanammonium)-dihydrogen-3,3′,4,4′benzophenone tetracarboxylate (28).
38 more elements
A polyimide of general formula (II) prepared using a salt of formula (I):
- wherein R1 and R2 are as previously defined and n is ≥2, wherein the polyimide is selected from the following:
- a) polyimides from tetrahydrofuran-2,3,4,5-tetracarboxylic acid and aliphatic diamines
- poly(N,N′-(1,3-propylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (101),
- poly(N,N′-(1,4-butylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (102),
- poly(N,N′-(1,5-pentylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (103),
- poly(N,N′-(2,2-dimethyl-1,3-propylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (104),
- poly(N,N′-(1,6-hexylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (105),
- poly(N,N′-(2-methyl-1,5-pentylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (106),
- poly(N,N′-(1,7-heptylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (107),
- poly(N,N′-(1,8-octylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (108),
- poly(N,N′-(1,9-nonylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (109);
- b) polyimides from tetrahydrofuran-2,3,4,5-tetracarboxylic acid and alicyclic diamines
- poly(N,N′-(1,2-cyclohexylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (110),
- poly(N,N′-(1,3-cyclohexylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (111),
- poly(N,N′-(1,4-cyclohexylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (112),
- poly(N,N′-(cyclohexane-1,3 -dimethylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (113),
- poly(N,N′-(cyclohexane-1,4-dimethylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (114),
- poly(N,N′-(norbornane dimethylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (115),
- poly(N,N′-(isophorylene)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (116),
- poly(N,N′-(tricyclo[5.2.1.02,6]decane-3(4), 8(9)-dimethylene)tetrahydrofuran-2,3,4,5 -tetracarboxylic acid diimide) (117),
- poly(N,N′-(4,4′-methylene-bis(2-methylcyclohexyl)tetrahydrofuran-2,3,4,5-tetracarboxylic acid diimide) (118);
- c) polyimides from 1,2,3,4-butanetetracarboxylic acid and alicyclic diamines
- poly(N,N′-(norbornane dimethylene)butane-1,2,3,4-tetracarboxylic acid diimide) (119),
- poly(N,N′-(tricyclo[5.2.1.02,6]decane-3(4),8(9)-dimethylene)butane-1,2,3,4-tetracarboxylic acid diimide) (120);
- d) polyimides from 1,2,3,4-cyclobutanetetracarboxylic acid and alicyclic diamines
- poly(N,N′-(norbornane dimethylene)cyclobutane-1,2,3,4-tetracarboxylic acid diimide) (121),
- poly(N,N′-(tricyclo[5.2.1.02,6]decane-3(4),8(9)-dimethylene)cyclobutane-1,2,3,4-tetracarboxylic acid diimide) (122);
- e) polyimides from 1,2,3,4-cyclopentanetetracarboxylic acid and alicyclic diamines
- poly(N,N′-(norbornane dimethylene)cyclopentane-1,2,3,4-tetracarboxylic acid diimide) (123),
- poly(N,N′-(tricyclo[5.2.1.02,6]decane-3(4),8(9)-dimethylene)cyclopentane-1,2,3,4-tetracarboxylic acid diimide) (124);
- f) polyimides from 1,2,4,5-cyclohexanetetracarboxylic acid and alicyclic diamines
- poly(N,N′-(norbornane dimethylene)cyclohexane-1,2,4,5-tetracarboxylic acid diimide) (125),
- poly(N,N′-(tricyclo[5.2.1.02,6]decane-3(4),8(9)-dimethylene)cyclohexane-1,2,4,5-tetracarboxylic acid diimide) (126);
- and
- g) polyimides from 3,3′,4,4′-benzophenonetetracarboxylic acid and alicyclic diamines
- poly(N,N′-(norbornane dimethylene)-3,3′,4,4′-benzophenone tetracarboxylic acid diimide) (127),
- poly(N,N′-(tricyclo[5.2.1.02,6]decane-3(4),8(9)-dimethylene)-3,3′,4,4′-benzophenonetetracarboxylic acid diimide) (128).
34 more elements
Dependencies are inferred from the claim text.