US4000187A
Expired / Lapsed
US
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Quinoline and anthrazoline polymers
Assignee: University of Iowa Research Foundation
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Filing: 1972-04-11
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Granted: 1976-12-28
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Expires: 1992-04-11
Abstract
Abstract Polymers containing recurring quinoline or anthrazoline groups which are reaction products of aromatic amino carbonyl compounds containing two sets of ortho-amino aldehyde or ortho-amino ketone functions attached to the aromatic nucleus having the general structure: ##STR1## (wherein R is hydrogen, or aryl and the Ar's are aryl groups) with methylene ketones containing two ketone functions having a methylene group adjacent to each ketone and having the general structure: ##STR2## (wherein R = hydrogen or aryl and R' = aryl and the Ar's are aryl groups) are described. According to the above, R from both the aromatic amino carbonyl and the aromatic methylene ketone could be hydrogen when producing a polymer, but the polymer in which both R's are hydrogen is excluded from this invention.
Inventors
- 👤 John K. Stille
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:30
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0683; C08G73/0688; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31942
Claims Analysis
Total Claims: 94
Claim 1
Independent Claim
137 words
A method for the preparation of polymers containing anthrazoline, isoanthrazoline or quinoline recurring units from the reaction of a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of ortho-amino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR23## wherein R is hydrogen or aryl, and the Ar, Ar', and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR24## wherein R is hydrogen or aryl, R' is aryl, and the Ar's are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer.
Claim 2
Independent Claim
137 words
A method for the preparation of polymers containing anthrazoline, isoanthrazoline or quinoline recurring units from the reaction of a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of ortho-amino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR23## wherein R is hydrogen or aryl, and the Ar, Ar', and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR24## wherein R is hydrogen or aryl, R' is aryl, and the Ar's are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer.
Claim 3
Dependent Claim
18 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar, of the aminocarbonyl monomer is monocyclic.
Claim 4
Dependent Claim
18 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar, of the aminocarbonyl monomer is polycyclic.
Claim 5
Dependent Claim
18 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar", of the aminocarbonyl monomer is monocyclic.
Claim 6
Dependent Claim
18 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar", of the aminocarbonyl monomer is polycyclic.
Claim 7
Dependent Claim
18 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar', of the aminocarbonyl monomer is monocyclic.
Claim 8
Dependent Claim
18 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar', of the aminocarbonyl monomer is polycyclic.
Claim 9
Dependent Claim
20 words
A method as defined in claim 1 wherein the aromatic amino carbonyl is in the form of a dihydrochloride salt.
Claim 10
Dependent Claim
17 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar", of the methylenecarbonyl is monocyclic.
Claim 11
Dependent Claim
18 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar", of the methylene carbonyl is polycyclic.
Claim 12
Dependent Claim
36 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar'", of the methylene carbonyl is structured such that the two methylene carbonyl functions are joined by two bridging aromatic nuclei which are each monocyclic.
Claim 13
Dependent Claim
33 words
A method as defined in claim 1 wherein the aromatic nucleus, Ar'", of the methylene carbonyl is structured such that the two methylene carbonyl functions are joined by a polycyclic bridging aromatic nucleus.
Claim 14
Dependent Claim
13 words
A method as defined in claim 1 wherein the amino carbonyl is 4,6-diaminoisophthalaldehyde.
Claim 15
Dependent Claim
13 words
A method as defined in claim 1 wherein the amino carbonyl is 2,5-diaminoterephthalaldehyde.
Claim 16
Dependent Claim
13 words
A method as defined in claim 1 wherein the amino carbonyl is 4,6-dibenzoyl-m-phenylenediamine.
Claim 17
Dependent Claim
13 words
A method as defined in claim 1 wherein the amino carbonyl is 2,5-dibenzoyl-p-phenylenediamine.
Claim 18
Dependent Claim
13 words
A method as defined in claim 1 wherein the amino carbonyl is 2,2'-diaminoisophthalophenone.
Claim 19
Dependent Claim
13 words
A method as defined in claim 1 wherein the amino carbonyl is 2,2'-diaminoterephthalophenone.
Claim 20
Dependent Claim
13 words
A method as defined in claim 1 wherein the amino carbonyl is 4,4'-(o-aminobenzoyl)biphenyl.
Claim 21
Dependent Claim
14 words
A method as defined in claim 1 wherein the amino carbonyl is 4,4'-(o-aminobenzoyl)diphenyl ether.
Claim 22
Dependent Claim
13 words
A method as defined in claim 1 wherein the amino carbonyl is 3,3'-dibenzoylbenzidine.
Claim 23
Dependent Claim
14 words
A method as defined in claim 1 wherein the amino carbonyl is 3,3'-dibenzoyl-4,4'-diaminodiphenyl ether.
Claim 24
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is biacetyl.
Claim 25
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 1,4-diphenacylbenzene.
Claim 26
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 1,4-diphenacetylbenzene.
Claim 27
Dependent Claim
14 words
A method as defined in claim 1 wherein the methylene ketone is 4,4'-diphenacetylphenyl ether.
Claim 28
Dependent Claim
14 words
A method as defined in claim 1 wherein the methylene ketone is 4,4'-diphenacetylphenyl sulfide.
Claim 29
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 4,4'-diphenacetylbiphenyl.
Claim 30
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is p-diacetylbenzene.
Claim 31
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 1,3-diacetylbenzene.
Claim 32
Dependent Claim
14 words
A method as defined in claim 1 wherein the methylene ketone is 4,4'-diacetylphenyl ether.
Claim 33
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 4,4'-diacetyldiphenylsulfide.
Claim 34
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 4,4'-diacetyldiphenylsulfone.
Claim 35
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 4,4'-diacetylbiphenyl.
Claim 36
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 2,6-diacetylpyridine.
Claim 37
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is dibenzo[a,e]cyclooctene-5,11[6H,12H]dione.
Claim 38
Dependent Claim
13 words
A method as defined in claim 1 wherein the methylene ketone is 1,10-diketo[2.2]metacyclophane.
Claim 39
Dependent Claim
23 words
A method as described in claim 1 wherein the reaction is carried out in a solvent which will not react with the monomers.
Claim 40
Dependent Claim
48 words
A method as described in claim 38 wherein the solvent is selected from the group consisting of benzene, chlorobenzene, o-dichlorobenzene, m-dichlorobenzene, p-dichlorobenzene, mixtures of dichlorobenzenes, 1-chloronaphthalene, 2-chloronaphthalene, tetralin, diphenyl ether, p-dioxane, tetrahydropyran, acetic acid, formic acid, trifluoroacetic acid, phenol, m-cresol, phosphoric acid, polyphosphoric acid, and methane sulfonic acid.
Claim 41
Dependent Claim
31 words
A method as described in claim 1 wherein the reaction is carried out in the presence of a base catalyst which is a hydroxylic base, an alkoxide or a Lewis base.
Claim 42
Dependent Claim
31 words
A method as described in claim 40 wherein the hydroxylic base catalysts are selected from the group consisting of hydroxides, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, alkali metal hydroxides.
Claim 43
Dependent Claim
38 words
A method as described in claim 40 wherein the reaction is carried out in a solvent which will not react with the monomers or the catalyst such that it will have an adverse effect on the polymerization reaction.
Claim 44
Dependent Claim
32 words
A method as described in claim 42 wherein the solvent is selected from the group consisting of benzene, tetralin, diphenyl ether, p-dioxane, tetrahydropyran, dimethylsulfoxide, hexamethylphosphoric triamide, dimethylformamide, tetrahydrothiophene dioxide dimethylacetamide, and N-methylpyrrolidone.
Claim 45
Dependent Claim
24 words
A method as described in claim 1 wherein the reaction is carried out by heating the reaction mixture between 25° C and 200° C.
Claim 46
Dependent Claim
20 words
A method as described in claim 38 wherein the reaction is carried out at the reflux temperature of the solvent.
Claim 47
Dependent Claim
20 words
A method as described in claim 42 wherein the reaction is carried out at the reflux temperature of the solvent.
Claim 48
Dependent Claim
30 words
The method as defined in claim 40, wherein said alkoxides are selected from the group consisting of sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, sodium t-butoxide, and potassium t-butoxide.
Claim 49
Dependent Claim
57 words
A composition comprising a polymer having recurring units of the general formula ##STR25## wherein the integers 1-8 define C atom positions in said unit, wherein said unit contains diaromatic substitution in the 2,8-, 3,7-, or 4,6- position or tetraaromatic substitution in the 3,4,6,7- or 2,4,6,8- positions, wherein the recurring units link at the 2,8 or 3,7 position.
Claim 50
Dependent Claim
57 words
A composition comprising a polymer having recurring units of the general formula ##STR25## wherein the integers 1-8 define C atom positions in said unit, wherein said unit contains diaromatic substitution in the 2,8-, 3,7-, or 4,6- position or tetraaromatic substitution in the 3,4,6,7- or 2,4,6,8- positions, wherein the recurring units link at the 2,8 or 3,7 position.
Claim 51
Dependent Claim
51 words
A polymer having recurring units of the general formula ##STR26## wherein integers 1-10 define C atom positions of said unit, wherein said unit contains diaromatic substitution in the 3,8-, 4,9-, or 2,7- or tetraaromatic substitution in the 3,4,8,9- or 2,4,7,9-positions, wherein the recurring units link at the 2,7 or 3,8 positions.
Claim 52
Dependent Claim
51 words
A polymer having recurring units of the general formula ##STR26## wherein integers 1-10 define C atom positions of said unit, wherein said unit contains diaromatic substitution in the 3,8-, 4,9-, or 2,7- or tetraaromatic substitution in the 3,4,8,9- or 2,4,7,9-positions, wherein the recurring units link at the 2,7 or 3,8 positions.
Claim 53
Dependent Claim
52 words
A polymer having recurring units of the general formula: ##STR27## wherein the integers 1-8 define C-atom positions of said, unit, wherein said unit contains aromatic substitution at 2-, 3-, 4-, positions or diaromatic substitution in the 2,4- or 3,4- position, said recurring units being linked at positions not occupied by aromatic substitution.
Claim 54
Dependent Claim
52 words
A polymer having recurring units of the general formula: ##STR27## wherein the integers 1-8 define C-atom positions of said, unit, wherein said unit contains aromatic substitution at 2-, 3-, 4-, positions or diaromatic substitution in the 2,4- or 3,4- position, said recurring units being linked at positions not occupied by aromatic substitution.
Claim 55
Dependent Claim
90 words
A polymer composition containing a polymer containing recurring anthrazoline units, comprising the reaction product of a compound of the general formula ##STR28## wherein R is hydrogen or aryl, wherein Ar is an aromatic nucleus with a single aromatic ring, with a methylene ketone, said methylene ketone containing two ketone functions, having a methylene group adjacent to each ketone, said anthrazoline unit being of the general formula ##STR29## wherein said anthrazoline unit contains pendant diaromatic substitution in the 2,8-, 3,7-, or 4,6-positions, or pendant tetraaromatic substitution in the 3,4,6,7- or 2,4,6,8-positions.
Claim 56
Dependent Claim
90 words
A polymer composition containing a polymer containing recurring anthrazoline units, comprising the reaction product of a compound of the general formula ##STR28## wherein R is hydrogen or aryl, wherein Ar is an aromatic nucleus with a single aromatic ring, with a methylene ketone, said methylene ketone containing two ketone functions, having a methylene group adjacent to each ketone, said anthrazoline unit being of the general formula ##STR29## wherein said anthrazoline unit contains pendant diaromatic substitution in the 2,8-, 3,7-, or 4,6-positions, or pendant tetraaromatic substitution in the 3,4,6,7- or 2,4,6,8-positions.
Claim 57
Dependent Claim
83 words
A polymer composition containing a polymer having recurring isoanthrazoline units, comprising the reaction product of (1) a compound of the general formula: ##STR30## wherein R is hydrogen or aryl, with (2) a methylene ketone, said methylene ketone containing two ketone functions having a methylene group adjacent to each ketone function, said isoanthrazoline unit being of the general formula: ##STR31## wherein said isoanthrazoline unit contains pendant diaromatic substitution in the 3,8-, 4,9-, or 2,7- positions, or pendant tetraaromatic substitution in the 3,4,8,9- or 2,4,7,9-positions.
Claim 58
Dependent Claim
83 words
A polymer composition containing a polymer having recurring isoanthrazoline units, comprising the reaction product of (1) a compound of the general formula: ##STR30## wherein R is hydrogen or aryl, with (2) a methylene ketone, said methylene ketone containing two ketone functions having a methylene group adjacent to each ketone function, said isoanthrazoline unit being of the general formula: ##STR31## wherein said isoanthrazoline unit contains pendant diaromatic substitution in the 3,8-, 4,9-, or 2,7- positions, or pendant tetraaromatic substitution in the 3,4,8,9- or 2,4,7,9-positions.
Claim 59
Dependent Claim
82 words
A polymer composition containing a polymer having recurring quinoline units, comprising the reaction product of (1) a compound of the general formula: ##STR32## wherein Ar' and Ar" are aryl groups, with (2) a methylene ketone, said methylene ketone containing two ketone functions having a methylene group adjacent to each ketone, said quinoline unit having the general formula: ##STR33## said quinoline unit containing pendant aromatic substitution in the 2-, 3-, or 4- positions, or pendant diaromatic substitution in the 2,4- or 3,4- positions.
Claim 60
Dependent Claim
82 words
A polymer composition containing a polymer having recurring quinoline units, comprising the reaction product of (1) a compound of the general formula: ##STR32## wherein Ar' and Ar" are aryl groups, with (2) a methylene ketone, said methylene ketone containing two ketone functions having a methylene group adjacent to each ketone, said quinoline unit having the general formula: ##STR33## said quinoline unit containing pendant aromatic substitution in the 2-, 3-, or 4- positions, or pendant diaromatic substitution in the 2,4- or 3,4- positions.
Claim 61
Independent Claim
156 words
A method for the preparation of polymers containing anthrazoline, isoanthrazoline or quinoline recurring units comprising reacting a compound selected from the group consisting of a. an aromatic amino carbonyl containing two sets of ortho-amino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR34## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with b. a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR35## wherein R is hydrogen or aryl, R' is aryl, and the Ar,Ar', and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer, in the presence of an acid or base catalyst to produce said polymers containing anthrazoline, isoanthrazoline or quinoline recurring units.
Claim 62
Independent Claim
156 words
A method for the preparation of polymers containing anthrazoline, isoanthrazoline or quinoline recurring units comprising reacting a compound selected from the group consisting of a. an aromatic amino carbonyl containing two sets of ortho-amino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR34## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with b. a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR35## wherein R is hydrogen or aryl, R' is aryl, and the Ar,Ar', and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer, in the presence of an acid or base catalyst to produce said polymers containing anthrazoline, isoanthrazoline or quinoline recurring units.
Claim 63
Dependent Claim
24 words
The method of claim 54 wherein compound (a) and compound (b) are mixed with a solvent inert under the reaction condition to said catalyst.
Claim 64
Dependent Claim
25 words
The method of claim 54 wherein said compounds (a) and (b) are contacted with said catalyst at temperature of about 25° C. to 250° C.
Claim 65
Dependent Claim
26 words
The method of claim 56 wherein said compounds (a) and (b) are mixed with a solvent which is inert under the reaction condition to said catalyst.
Claim 66
Dependent Claim
46 words
The method of claim 54 wherein compound (a) and compound (b) are allowed to react in the presence of an acid or base catalyst, at temperatures from about 25° C. to 250° C. in a solvent which is inert under the reaction condition to said catalyst.
Claim 67
Dependent Claim
19 words
The method of claim 54 wherein the polymer containing anthrazoline, isoanthrazoline or quinoline recurring units, is separated by precipitation.
Claim 68
Dependent Claim
21 words
A method as described in claim 54 wherein said base catalyst is a hydroxylic base, an alkoxide or a Lewis base.
Claim 69
Dependent Claim
32 words
A method as described in claim 60 wherein the hydroxylic base catalysts are selected from the group consisting of hydroxides, alkoxides, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide, alkali metal hydroxides.
Claim 70
Dependent Claim
30 words
The method as defined in claim 60 wherein said alkoxides are selected from the group consisting of sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, sodium t-butoxide, and potassium t-butoxide.
Claim 71
Independent Claim
157 words
A method for preparation of polymers containing anthrazoline, isoanthrazoline or quinoline recurring units comprising reacting a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of orthoamino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR36## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR37## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer, and wherein the reaction is carried out in the presence of acid catalyst which is a protonic acid or a Lewis acid.
Claim 72
Independent Claim
157 words
A method for preparation of polymers containing anthrazoline, isoanthrazoline or quinoline recurring units comprising reacting a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of orthoamino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR36## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR37## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer, and wherein the reaction is carried out in the presence of acid catalyst which is a protonic acid or a Lewis acid.
Claim 73
Dependent Claim
49 words
A method as defined in claim 63 wherein the said protonic acid catalyst is selected from the group consisting of sulfuric acid, hydrochloric acid, hydrofluoric acid, hydrobromic acid, hydroiodic acid, chloric acid, methane sulfonic acid, phosphoric acid, polyphosphoric acid, trifluoroacetic acid, toluene sulfonic acid, and a sulfonated polymer resin.
Claim 74
Dependent Claim
65 words
A composition comprising a polymer having recurring units of the general formula ##STR38## wherein the integers 1-8 define C atom positions in said unit, wherein said unit contains diaromatic substitution in the 2,8-, 3,7-, or 4,6- position or tetraaromatic substitution in the 3,4, 6,7- or 2,4,6,8- positions, wherein the recurring units link at the 2,8 or 3,7 position, and wherein the aromatic groups are phenyl.
Claim 75
Dependent Claim
65 words
A composition comprising a polymer having recurring units of the general formula ##STR38## wherein the integers 1-8 define C atom positions in said unit, wherein said unit contains diaromatic substitution in the 2,8-, 3,7-, or 4,6- position or tetraaromatic substitution in the 3,4, 6,7- or 2,4,6,8- positions, wherein the recurring units link at the 2,8 or 3,7 position, and wherein the aromatic groups are phenyl.
Claim 76
Dependent Claim
59 words
A polymer having recurring units of the general formula ##STR39## wherein integers 1-10 define C atom positions of said unit, wherein said unit contains diaromatic substitution in the 3,8-, 4,9-, or 2,7- or tetraaromatic substitution in the 3,4,8,9- or 2,4,7,9- positions, wherein the recurring units link at the 2,7 or 3,8 positions, and wherein the aromatic groups are phenyl.
Claim 77
Dependent Claim
59 words
A polymer having recurring units of the general formula ##STR39## wherein integers 1-10 define C atom positions of said unit, wherein said unit contains diaromatic substitution in the 3,8-, 4,9-, or 2,7- or tetraaromatic substitution in the 3,4,8,9- or 2,4,7,9- positions, wherein the recurring units link at the 2,7 or 3,8 positions, and wherein the aromatic groups are phenyl.
Claim 78
Dependent Claim
59 words
A polymer having recurring units of the general formula ##STR40## wherein the integers 1-8 define C-atom positions of said unit, wherein said unit contains aromatic substitution of 2-, 3-, 4-, positions or diaromatic substitution in the 2,4- or 3,4- position, and wherein the aromatic groups are phenyl, said recurring units being linked at positions not occupied by aromatic substitution.
Claim 79
Dependent Claim
59 words
A polymer having recurring units of the general formula ##STR40## wherein the integers 1-8 define C-atom positions of said unit, wherein said unit contains aromatic substitution of 2-, 3-, 4-, positions or diaromatic substitution in the 2,4- or 3,4- position, and wherein the aromatic groups are phenyl, said recurring units being linked at positions not occupied by aromatic substitution.
Claim 80
Dependent Claim
138 words
A cast film comprising a polymer containing anthrazoline, isoanthrazoline or quinoline recurring units prepared from the reaction of a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of ortho-amino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR41## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR42## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer.
Claim 81
Dependent Claim
138 words
A cast film comprising a polymer containing anthrazoline, isoanthrazoline or quinoline recurring units prepared from the reaction of a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of ortho-amino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR41## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR42## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer.
Claim 82
Dependent Claim
143 words
A coating on a substrate wherein said coating comprises a polymer containing anthrazoline, isoanthrazoline or quinoline recurring units prepared from the reaction of a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of ortho-amino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR43## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR44## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer.
Claim 83
Dependent Claim
143 words
A coating on a substrate wherein said coating comprises a polymer containing anthrazoline, isoanthrazoline or quinoline recurring units prepared from the reaction of a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of ortho-amino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR43## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR44## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer.
Claim 84
Dependent Claim
35 words
A method as defined in claim 63 wherein said Lewis acid is selected from the group consisting of boron trifluoride, phosphorus pentafluoride, sulfur trioxide, aluminum chloride, antimony trifluoride, antimony pentafluoride, antimony trichloride and stannic chloride.
Claim 85
Dependent Claim
24 words
A method as described in claim 60 wherein said Lewis base is selected from the group consisting of N-ethyl morpholine, triethylamine, 1,5-diazabicyclo[4.3.0]-non-5-ene and 1,4-diazabicyclo[2.2.2]octane.
Claim 86
Independent Claim
165 words
A method for the preparation of a polymer containing anthrazoline, isoanthrazoline or quinoline recurring units comprising reacting a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of orthoamino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR45## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR46## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer, wherein compound (a) and compound (b) are allowed to react in the presence of an acid or base catalyst, at temperatures from about 25° C to 250° C.
Claim 87
Independent Claim
165 words
A method for the preparation of a polymer containing anthrazoline, isoanthrazoline or quinoline recurring units comprising reacting a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of orthoamino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR45## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR46## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer, wherein compound (a) and compound (b) are allowed to react in the presence of an acid or base catalyst, at temperatures from about 25° C to 250° C.
Claim 88
Independent Claim
167 words
A method for the preparation of a polymer containing anthrazoline, isoanthrazoline or quinoline recurring units comprising reacting a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of orthoamino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR47## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR48## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer, in the presence of an acid catalyst to produce said polymers containing anthrazoline, isoanthrazoline or quinoline recurring units, wherein said acid catalyst is a protonic acid or a Lewis acid.
Claim 89
Independent Claim
167 words
A method for the preparation of a polymer containing anthrazoline, isoanthrazoline or quinoline recurring units comprising reacting a compound selected from the group consisting of (a) an aromatic amino carbonyl containing two sets of orthoamino carbonyl functions attached to an aromatic nucleus selected from the group consisting of structure represented by the formulas: ##STR47## wherein R is hydrogen or aryl, and Ar, Ar' and Ar" are aryl groups, with (b) a methylene ketone compound selected from the group consisting of the structures represented by the formulas: ##STR48## wherein R is hydrogen or aryl, R' is aryl, and Ar, Ar' and Ar" are aryl groups except that the amino carbonyl and the methylene ketone are selected such that neither or at least only one of them contain R equal to hydrogen in the preparation of any given polymer, in the presence of an acid catalyst to produce said polymers containing anthrazoline, isoanthrazoline or quinoline recurring units, wherein said acid catalyst is a protonic acid or a Lewis acid.
Claim 90
Dependent Claim
23 words
A method as described in claim 62 wherein said base is selected from the group consisting of N-ethyl morpholine, triethylamine, 1,5-diazabicyclo[4.3.0]-non-5-ene and 1,4-diazabicyclo[2.2.2]octane.
Claim 91
Dependent Claim
51 words
A method as defined in claim 73 wherein the said protonic acid catalyst is selected from the group consisting of protonic acids, sulfuric acid, hydrochloric acid, hydrofluoric acid, hydrobromic acid, hydroiodic acid, chloric acid, methane sulfonic acid, phosphoric acid, polyphosphoric acid, trifluoroacetic acid, toluene sulfonic acid, and a sulfonated polymer resin.
Claim 92
Dependent Claim
35 words
A method as defined in claim 73 wherein said Lewis acid is selected from the group consisting of boron trifluoride, phosphorus pentafluoride, sulfur trioxide, aluminum chloride, antimony trifluoride, antimony pentafluoride, antimony trichloride and stannic chloride.
Claim 93
Dependent Claim
116 words
A polymer containing a recurring structure represented by a member selected from the following group: ##STR49## wherein n represents an integer such that the products will have a sufficiently high molecular weight to afford an inherent viscosity of at least about 0.1 in a solvent for said polymer, at 25° C, measured in a solvent selected from the group consisting of H 2 SO 4 , CH 3 SO 3 H and hexamethylphosphoramide at a concentration of polymer from 0.04 g/dl to 0.5 g/dl, wherein R is hydrogen or aryl, wherein R' is aryl, wherein if R is hydrogen the nitrogen containing ring must contain the substituent R', wherein Ar, Ar', and Ar" are aryl groups.
Claim 94
Dependent Claim
116 words
A polymer containing a recurring structure represented by a member selected from the following group: ##STR49## wherein n represents an integer such that the products will have a sufficiently high molecular weight to afford an inherent viscosity of at least about 0.1 in a solvent for said polymer, at 25° C, measured in a solvent selected from the group consisting of H 2 SO 4 , CH 3 SO 3 H and hexamethylphosphoramide at a concentration of polymer from 0.04 g/dl to 0.5 g/dl, wherein R is hydrogen or aryl, wherein R' is aryl, wherein if R is hydrogen the nitrogen containing ring must contain the substituent R', wherein Ar, Ar', and Ar" are aryl groups.
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) | 1979-12-28 | 1980-06-28 | 1980-12-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-28 | 1984-06-28 | 1984-12-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-28 | 1988-06-28 | 1988-12-28 | $7700.00 | Window Closed / Lapsed |