Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
2000-01-26
2001-08-21
Hampton-Hightower, P. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C528S125000, C528S126000, C528S128000, C528S170000, C528S171000, C528S172000, C528S173000, C528S174000, C528S175000, C528S176000, C528S179000, C528S183000, C528S185000, C528S188000, C528S220000, C528S229000, C528S350000, C528S351000
Reexamination Certificate
active
06277950
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates generally to a formulation and preparation method of a kind of tractable polyimides that are organic-soluble with controllable solubility.
BACKGROUND OF THE INVENTION
Aromatic polyimides were well known as polymeric materials of high performance for their excellent thermal stabilities and balanced mechanical and electric properties. Polyimides were mainly used in the aerospace and electronic industries in the forms of films and moldings. Other uses for these polymers such as adhesives, gas separation membranes, composite matrices, coatings, and foams were rapidly increasing. However, aromatic polyimides are difficult to be processed because of high softening temperatures and limited solubilities in commercially available solvents; accordingly the improvements to their solubility and heat plasticity without decreasing their original excellent characteristics are the aims of the present researchers.
The literature is flooded with claims of polyimides according to our specific paper and patent search for soluble polyimides. Most of the literature described the improvement of diamines and relatively less literature described the invention of dianhydrides in the preparation of organosolubie polyimides. The diamines used in the synthesis of organosoluble polyimides have in general three kinds of structures. The first type is polyimides prepared from a polysiloxane diamine, which have an improved adhesion with a semiconductor substrate but suffer poorer thermal properties and strength of films. The second type is polyimides prepared from a diamine having two meta amino groups [such as, 3,3-diaminodiphenylsulfone and 1,3-bis(3-aminophenoxy)benzene], which have enhanced solubility but a lower degree of polymerization due to poor reactivity of the diamine. The third type is polyimides prepared from a diamine having two para amino groups, which will have organosolubility only when the diamines have more than one flexible connector groups selected from isopropyl, hexafluoroisopropyl, ether and sulfone [such as 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl ]hexafluoropropane, and bis[4-(4-aminophenoxy)phenyl]sulfone.
Our specific paper and patent search for organosoluble polyimides based on diamine are listed as follows:
(a) Patents
JP 09118,808 (1997)
Chemical Abstract 127: 52287j
EP 729,996 (1996)
Chemical Abstract 125: 276948x
U.S. Pat. No. 5,480,965 (1996)
Chemical Abstract 124: 345157g
JP 07-224,152 (1995)
Chemical Abstract 124: 31222g
JP 07-310,048 (1995)
Chemical Abstract 124: 291209e
EP 639,621 (1995)
Chemical Abstract 123: 85015q
JP 07-224,151 (1995)
Chemical Abstract 123: 315836q
JP 07-224,150 (1995)
Chemical Abstract 123: 315835p
JP 06-172,524 (1994)
Chemical Abstract 121: 281875t
JP 06-172,523 (1994)
Chemical Abstract 121: 281874s
JP 06-172,525 (1994)
Chemical Abstract 121: 281876u
U.S. Pat. No. 5,212,279 (1993)
Chemical Abstract 119: 251699e
JP 04-337,326 (1992)
Chemical Abstract 119: 73356f
JP 04-108,879 (1992)
Chemical Abstract 117: 92386r
JP 04-108,880 (1992)
Chemical Abstract 117: 92387s
EP 438,751 (1991)
Chemical Abstract 115: 234851y
U.S. Pat. No. 4,931,539 (1990)
Chemical Abstract 113: 133121p
JP 02-43,221 (1990)
Chemical Abstract 113: 41153c
JP 02-92,930 (1990)
Chemical Abstract 113: 116471k
JP 02-286,706 (1990)
Chemical Abstract 115: 115256y
EP 284,803 (1988)
Chemical Abstract 110: 155428j
JP 63-00,353 (1988)
Chemical Abstract 109: 46242c
JP 62-265,326 (1987)
Chemical Abstract 108: 133522s
JP 61-108,627 (1986)
Chemical Abstract 106: 20093t
JP 61-241,358 (1986)
Chemical Abstract 106: 157082h
JP 61-57,620 (1986)
Chemical Abstract 105: 153750f
JP 61-59,334 (1986)
Chemical Abstract 105: 200510q
EP 194,865 (1986)
Chemical Abstract 105: 228674v
JP 60-217,261 (1985)
Chemical Abstract 104: 188323a
JP 49-12,592 (1974)
Chemical Abstract 83: 62006d
JP 49-19,119 (1974)
Chemical Abstract 82: 126002p
JP 49-18,639 (1974)
Chemical Abstract 82: 125993a
JP 49-30,717 (1974)
Chemical Abstract 82: 112854f
JP 49-18,118 (1974)
Chemical Abstract 82: 58904g
JP 46-17,145 (1971)
Chemical Abstract 75: 118915d
Fr 1,539,074 (1968)
Chemical Abstract 71: 4608t
(b) Articles
1. Arnold, C. A.; etc.; Polymer 30, 986 (1989).
2. Omote, T.; etc.; Polym. Eng. Sci. 29, 945 (1989).
3. Lee, H.-R; etc; Macromolecules. 23, 502 (1990).
4. Arnold, F. E,; etc.; J. Mater. Chem. 3, 353 (1993).
Our specific paper and patent search for organosoluble polyimides based on diether-diamine:
1. Yang C.-P; Lin J.-H, J. Polym. Sci., Part A:, 31, 2153 (1993).
2. Yang C.-P; Chen W.-T, J. Polym. Sci., Part A:, 31, 2799 (1993).
3. Yang C.-P; Chen W.-T, Macromol. Chem., 194, 3061 (1993).
4. Yang C.-P; Chen W.-T, Macromolecules, 26, 4865 (1993).
5. Yang C.-P; Lin J.-H, J. Polym. Sci., Part A:, 32, 423 (1994).
6. Yang C.-P; Lin J.-H, J. Polym. Sci., Part A:, 32, 369 (1994).
7. Hsiao S.-H; Yang C.-P; Fan J.-C, J. Polym. Res., 1, No. 4, 345 (1994).
8. Hsiao S.-H; Yang C.-P; Lin C.-K, J. Polym. Res., 2, No. 1, 1 (1995).
9. Yang C.-P; Hsiao S.-H; Jang C.-C, J. Polym. Sci., Part A:, 33, 1487 (1995).
10. Yang C.-P; Lin J.-H, Polymer, 36, 2607 (1995).
11. Yang C.-P; Lin J.-H, Polymeric Materials Encyclopedia, 9, 6214 (1996).
12. Hsiao S.-H; Yang C.-P; Yang C.-Y, J. Polym. Sci., Part A:, 35, 1469 (1997).
13. Liaw D.-J; Liaw B.-Y, Polym. J.,28, 970 (1996).
The diamine, 1,4-bis(4-aminophenoxy)-2-tert-butylbenzene, was first disclosed in U.S. Pat. No. 5,085,676 (1992). The assignee of this U.S. patent, Du Pont Company, has claimed that the polyamides synthesized from this diamine, 1,4-bis(4-aminophenoxy)-2-tert-butylbenzene, possess a potential application as a gas separation membrane.
SUMMARY OF THE INVENTION
The present invention provides a formulation and preparation method of a kind of tractable polyimides and co-polyimides that are organic-soluble with controllable solubility and also exhibit comparable thermal properties and mechanical properties. The series of organosoluble polyimides (Pls) and co-polyimides of the present invention are prepared from a specific romatic diamine having a tert-butyl group, 1,2-bis(4-aminophenoxy)-4-tert-butylbenzene, or a mixture of this specific aromatic diamine and other diamines with various dianhydrides.
The present invention also provides an organic solution of a polyimide and an organic solution of a co-polyimide, wherein the polyimide and co-polyimide are prepared from the specific aromatic diamine, 1,2-bis(4-aminophenoxy)-4-tert-butylbenzene, and the organic solvent is selected from the group consisting essentially of N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), m-cresol, pyridine, tetrahydrofuran (THF), chloromethane, and chloroethane.
The present invention further discloses methods for forming a polyimide film and a co-polyimide film, which comprise the following common steps: mixing the polyimide or the co-polyimide of the present invention and the organic solvent described above to form an organic solution; casting or coating said organic solution on a substrate to form a layer; and removing said solvent from said layer to form a polyimide or co-polyimide film.
DETAILED DESCRIPTION OF THE INVENTION
In general the polyimide films are prepared by heating a precursor of the polyimide, polyamic acid (PAA), because most of the conventional polyimides (Pls) can not easily dissolve in an organic solvent. Therefore, it is not feasible to form a polyimide film on a substrate which is adversely affected by high temperature. Further, the polyimide is difficult to be processed because of high softening temperature thereof, limited solubility in commercially available solvents thereof, and poor moist and thermal stability of poly(amic acid). In the present invention, a specific diamine having the following formula 11, 1,2-bis(4-aminophenoxy)-4-tert-butylbenzene, is prepared and used in the preparation of organosoluble polyimides, which also have excellent mechanical and thermal properties. In this invention we al
Chen Shin-Hung
Hsiao Sheng-Huei
Yang Chin-Ping
Hampton-Hightower P.
Jackson Walker L.L.P.
National Science Council
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