1. A method for the synthesis of an activated bisimide, comprising
reacting 4-halotetrahydrophthalic anhydride with a primary amine having the formula A-NH2 to yield an N-substituted-4-halotetrahydrophthalimide wherein A is a group which activates the tetrahydrophthalimide ring system to aromatization;
aromatizing activated 4-halotetrahydrophthalimide in the presence of a catalyst to yield an activated 4-halophthalimide; and
treating activated 4-halophthalimide (V) with a disodium salt of a dihydroxy compound having the structure HO\u2014S\u2014OH, to yield the activated bisimide (VI):
wherein S comprises a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a substituted straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, a substituted cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms or a substituted arylene group having from 6 to about 20 carbon atoms.
2. The method of claim 1, wherein S is selected from the group consisting of a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms, halogenated derivatives of arylene groups having from about 6 to 20 carbons.
3. The method of claim 1, wherein the dihydroxy compound is a bis(phenol) having the formula (XIII):
wherein T is selected from the group consisting of a single bond linking the two aryl groups, a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms; an arylene group having from 6 to about 20 carbon atoms, sulfide, carbonyl, sulfoxide, ether and mixtures thereof.
4. The method of claim 3, wherein T is selected from the group consisting of 2,2-bis4-hydroxyphenylpropane; 4,4\u2032-bis(4-hydroxyphenyl)diphenyl ether; 4,4\u2032-bis(4-phenoxy)diphenyl sulfide; 4,4\u2032-bis(4-hydroxyphenyl)benzophenone; 4,4\u2032-bis(4-hydroxyphenyl)diphenyl sulfone; 2,2-bis4-(3-hydroxyphenyl) phenylpropane; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl ether; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl sulfide; 4,4\u2032-bis(3-hydroxyphenyl)benzophenone; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl sulfone; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl-2,2-propane; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl ether; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl sulfide; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)benzophenone, and 4-(hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl sulfone dianhydride, and mixtures thereof.
5. The method of claim 3, wherein the dihydroxy compound is bisphenol A.
6. The method of claim 1, wherein A is selected from the group consisting of pyridine, chloropyridine, nitropyridine, pyrimidine, pyrazine, thiazole, methylthiazole, benzothiazole, 1,3,4-thiadiazole, and benzotriflouride.
7. The method of claim 1, wherein A is 2-pyridyl.
8. The method of claim 1, wherein the catalyst is copper based.
9. The method of claim 8, wherein the catalyst further comprises activated carbon.
10. A method for the synthesis of poly(etherimide)s, comprising
reacting 4-halotetrahydrophthalic anhydride with a primary amine having the formula A-NH2 to yield an N-substituted-4-halotetrahydrophthalimide wherein A is a group which activates the tetrahydrophthalimide ring system to aromatization;
aromatizing N-substituted-4-halotetrahydrophthalimide in the presence of a catalyst to yield an N-substituted-4-halophthalimide; and
treating N-substituted-4-halophthalimide with a disodium salt of a dihydroxy compound having the structure HO\u2014S\u2014OH, to yield the activated bisimide (VI);
wherein S comprises a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a substituted straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, a substituted cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms or a substituted arylene group having from 6 to about 20 carbon atoms; and
reacting activated bisimide (XII) with a diamine to form a poly(etherimide) and the primary amine.
11. The method of claim 10, wherein S is selected from the group consisting of a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms, halogenated derivatives of arylene groups having from about 6 to 20 carbons.
12. The method of claim 11, wherein the dihydroxy compound is a bis(phenol) having the formula (XIII):
wherein T is selected from the group consisting of a single bond linking the two aryl groups, a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms; an arylene group having from 6 to about 20 carbon atoms, sulfide, carbonyl, sulfoxide, ether and mixtures thereof.
13. The method of claim 12, wherein the T is selected from the group consisting of 2,2-bis4-hydroxyphenylpropane; 4,4\u2032-bis(4-hydroxyphenyl)diphenyl ether; 4,4\u2032-bis(4-phenoxy)diphenyl sulfide; 4,4\u2032-bis(4-hydroxyphenyl)benzophenone; 4,4\u2032-bis(4-hydroxyphenyl)diphenyl sulfone; 2,2-bis4-(3-hydroxyphenyl)phenylpropane; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl ether; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl sulfide; 4,4\u2032-bis(3-hydroxyphenyl)benzophenone; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl sulfone; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl-2,2-propane; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl ether; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl sulfide; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)benzophenone, and 4-(hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl sulfone dianhydride, and mixtures thereof.
14. The method of claim 10, wherein A is selected from the group consisting of pyridine, chloropyridine, nitropyridine, pyrimidine, pyrazine, thiazole, methylthiazole, benzothiazole, 1,3,4-thiadiazole, and benzotriflouride.
15. The method of claim 10, wherein A is 2-pyridyl.
16. The method of claim 10, wherein the diamine has the structure H2N-Z-NH2, wherein Z is selected from the group consisting of a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms, halogenated derivatives of an arylene group having from 6 to about 20 carbon atoms, and diarylene radicals of the following general formula (XV):
wherein Q includes, but is not limited to, the formula (XVI):
wherein y is an integer from about 1 to about 5, methylene, ethylene, propylene, isopropylene, n-butylene, 1,3-phenylene, naphthylene, and mixtures thereof.
17. The method of claim 10, wherein the catalyst is copper based.
18. The method of claim 17, wherein the catalyst further comprises activated carbon.
19. The method of claim 10 further comprising recycling the primary amine.
20. A method for the synthesis of poly(etherimide)s, comprising
reacting 4-halotetrahydrophthalic anhydride with a primary amine having the formula A-NH2 to yield an N-substituted-4-halotetrahydrophthalimide wherein A is a group which activates the tetrahydrophthalimide ring system to aromatization;
aromatizing the N-substituted-4-halotetrahydrophthalimide in the presence of a catalyst to yield an N-substituted-4-halophthalimide; and
treating N-substituted-4-halophthalimide with a disodium salt of a dihydroxy compound having the structure HO\u2014S\u2014OH, to yield the activated bisimide (VI); and
converting the activated bisimide (VI) to dianhydride (VIII)
wherein S comprises a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a substituted straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, a substituted cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms or a substituted arylene group having from 6 to about 20 carbon atoms
and reacting dianhydride (VIII) with a diamine to yield a poly(etherimide).
21. The method of claim 20, wherein S is selected from the group consisting of a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms, halogenated derivatives of arylene groups having from about 6 to 20 carbons.
22. The method of claim 20, wherein the dihydroxy compound is a bis(phenol) having the formula (XIII):
wherein T is selected from the group consisting of a single bond linking the two aryl groups, a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms; an arylene group having from 6 to about 20 carbon atoms, sulfide, carbonyl, sulfoxide, ether and mixtures thereof.
23. The method of claim 22, wherein T is selected from the group consisting of 2,2-bis4-hydroxyphenylpropane; 4,4\u2032-bis(4-hydroxyphenyl)diphenyl ether; 4,4\u2032-bis(4-phenoxy)diphenyl sulfide; 4,4\u2032-bis(4-hydroxyphenyl)benzophenone; 4,4\u2032-bis(4-hydroxyphenyl)diphenyl sulfone; 2,2-bis4-(3-hydroxyphenyl)phenylpropane; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl ether; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl sulfide; 4,4\u2032-bis(3-hydroxyphenyl)benzophenone; 4,4\u2032-bis(3-hydroxyphenyl)diphenyl sulfone; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl-2,2-propane; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl ether; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl sulfide; 4-(3-hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)benzophenone, and 4-(hydroxyphenyl)-4\u2032-(4-hydroxyphenyl)diphenyl sulfone dianhydride, and mixtures thereof.
24. The method of claim 20, wherein A is selected from the group consisting of pyridine, chloropyridine, nitropyridine, pyrimidine, pyrazine, thiazole, methylthiazole, benzothiazole, 1,3,4-thiadiazole, and benzotriflouride.
25. The method of claim 20, wherein A is 2-pyridyl.
26. The method of claim 20, wherein the diamine has the structure H2N-Z-NH2, wherein Z is selected from the group consisting of a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms, halogenated derivatives of an arylene group having from 6 to about 20 carbon atoms, and diarylene radicals of the following general formula (XV):
wherein Q includes, but is not limited to, the formula (XVI):
wherein y is an integer from about 1 to about 5, methylene, ethylene, propylene, isopropylene, n-butylene, 1,3-phenylene, naphthylene, and mixtures thereof.
27. The method of claim 20, wherein the activated bisimide (VI) is converted to dianhydride (VIII) by reacting the activated bisimide with phthalic anhydride.
28. The method of claim 20, wherein the activated bisimide (VI) is converted to dianhydride (VIII) by hydrolysis ring closure.
29. The method of claim 20, wherein the catalyst is copper based.
30. The method of claim 29, wherein the catalyst further comprises activated carbon.
31. A method for the synthesis of poly(etherimide)s, comprising
reacting 4-halotetrahydrophthalic anhydride with a primary amine having the formula A-NH2 to yield an N-substituted-4-halotetrahydrophthalimide wherein A is a group which activates the tetrahydrophthalimide ring system to aromatization;
aromatizing N-substituted-4-halotetrahydrophthalimide in the presence of a catalyst to yield an N-substituted-4-halophthalimide in the presence of a catalyst;
treating N-substituted-4-halophthalimide (V) with a diamine having the structure H2N-Z-NH2, wherein Z is selected from the group consisting of a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms, halogenated derivatives of an arylene group having from 6 to about 20 carbon atoms, and diarylene radicals of the following general formula (XV):
wherein O includes, but is not limited to, the formula (XVI):
wherein y is an integer from about 1 to about 5 methylene, ethylene, propylene, isopropylene, n-butylene, 1,3-phenylene, naphthylene, and mixtures thereof
to produce the dihalobisimide (IX); and
reacting dihalobisimide (IX) with the disodium salt of a dihydroxy compound having the structure HO\u2014S\u2014OH wherein S comprises a straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a substituted straight or branched chain alkylene group having from about 2 to about 20 carbon atoms, a cycloalkylene group having from about 3 to about 20 carbon atoms, a substituted cycloalkylene group having from about 3 to about 20 carbon atoms, an arylene group having from 6 to about 20 carbon atoms or a substituted arylene group having from 6 to about 20 carbon atoms, to yield poly(etherimide).
32. The method of claim 31, wherein the catalyst is copper based.
33. The method of claim 32, wherein the catalyst further comprises activated carbon.
34. The method of claim 31, wherein A is selected from the group consisting of pyridine, chloropyridine, nitropyridine, pyrimidine, pyrazine, thiazole, methylthiazole, benzothiazole, 1,3,4-thiadiazole, and benzotriflouride.
35. The method of claim 34, wherein A is 2-pyridyl.
36. The method of claim 31, wherein the dihydroxy compound is bisphenol A.
37. A method for the synthesis of an activated 4-halophthalimide, comprising
reacting 4-halotetrahydrophthalic anhydride with a primary amine having the formula A-NH2 to yield an N-substituted-4-halotetrahydrophthalimide wherein A is a group which activates the tetrahydrophthalimide ring system to aromatization; and
aromatizing activated 4-halotetrahydrophthalimide in the presence of a catalyst to yield an activated 4-halophthalimide.
38. The method of claim 37, wherein the catalyst is copper based.
39. The method of claim 38, wherein the catalyst further comprises activated carbon.
40. The method of claim 37, wherein A is selected from the group consisting of pyridine, chloropyridine, nitropyridine, pyrimidine, pyrazine, thiazole, methylthiazole, benzothiazole, 1,3,4-thiadiazole, and benzotriflouride.
41. The method of claim 40, wherein A is 2-pyridyl.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A one-piece flush seating roof bolt head adapted for use with an embossed load bearing plate comprising:
a first section adapted for insertion into a roof hole, said first section having a first end surface;
a second section adapted for seating flush against the inside area of the embossed load bearing plate, said second section having a surface for load distribution;
a third section adapted for receiving a tightening tool, said third section having a second end surface of the cable bolt head; and
a first tapered through-hole portion extending through said first section through said second section and forming an openings in said first and second end surfaces for accommodating a cable bolt portion.
2. The roof bolt head of claim 1, wherein said second section has a curved surface which sets flush within an embossed area of the embossed load bearing plate and has a opposite surface substantially flush with a high point of embossment of the embossed load bearing plate.
3. The roof bolt head of claim 2, wherein the curved surface has a first portion substantially transverse in cross-section to the first section; a second portion having a substantially linear cross-sectional profile; a third potion having a curved cross-sectional profile between the first portion and the second portion; and a fourth portion disposed between the second portion and the third section and substantially transverse to said opposite surface of the second section.
4. An apparatus comprising:
an embossed load bearing plate;
a cable bolt body;
a one-piece flush seating roof bolt head disposed at an end of said cable bolt body and adapted for seating within the embossed load bearing plate;
said roof bolt head comprising:
a first section adapted for insertion into a roof hole, said first section having a first end surface;
a second section adapted for seating flush against the inside area of the embossed load bearing plate, said second section having a surface for load distribution;
a third section adapted for receiving a tightening tool, said third section having a second end surface of the cable bolt head; and
a first tapered through-hole portion extending through said first section through said second section and forming an openings in said first and second end surfaces for accommodating a cable bolt portion.
5. The roof bolt head of claim 4, wherein said second section has a curved surface which sets flush within an embossed area of the embossed load bearing plate and has a opposite surface substantially flush with a high point of embossment of the embossed load bearing plate.
6. The roof bolt head of claim 5, wherein the curved surface has a first portion substantially transverse in cross-section to the first section; a second portion having a substantially linear cross-sectional profile; a third potion having a curved cross-sectional profile between the first portion and the second portion; and a fourth portion disposed between the second portion and the third section and substantially transverse to said opposite surface of the second section.