US4410686A
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US
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Norbornyl modified polyesteramides and process for preparing same
Assignee: Dow Chemical Co
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Filing: 1981-12-21
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Granted: 1983-10-18
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Expires: 2001-12-21
Abstract
Abstract Polyesteramides modified by having at least one terminal norbornene radical have improved physical and chemical properties, such as enhanced corrosion resistance, electrical properties, and heat stability. The modified polyesteramides are prepared by a process of reacting a dicarboxylic acid, a diamine, a polyol and a norbornene compound.
Inventors
- 👤 Robert E. Hefner, Jr.
- 👤 James C. Uroda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 10:20
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/44; H; H05; H05K; H05K1/00; H05K1/02; H05K1/03; H05K1/0313; H05K1/032; H05K1/0346
Claims Analysis
Total Claims: 72
Claim 1
Independent Claim
143 words
A norbornyl modified polyesteramide composed of: (A) a central esteramide chain consisting essentially of: (a) diamino groups of the formula: ##STR2## wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, aliphatic, cycloaliphatic and aromatic or R 1 and R 2 together form an aliphatic ring, and R 3 is a divalent organic radical selected from the group consisting of alkylene, ether-linked alkylene, ether-linked arylene, alkylene amino-linked alkylene, alkylene amino-linked cycloalkylene, cycloalkylene, polycycloalkylene, arylene, alkylarylene bis(alkyl)cycloalkylene and bis(alkyl)polycycloalkylene, (b) bisalkoxy groups of the formula: --O--R.sub.3 --O-- wherein R 3 is a divalent organic radical as before defined, (c) carboxylic acid groups at least a part of which are α,β-unsaturated carboxylic groups with any remainder being saturated aliphatic carboxylic groups, aromatic carboxylic groups or mixtures thereof, (B) at least one terminal group of said polyesteramide being a norbornyl radical.
Claim 2
Dependent Claim
143 words
A norbornyl modified polyesteramide composed of: (A) a central esteramide chain consisting essentially of: (a) diamino groups of the formula: ##STR2## wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, aliphatic, cycloaliphatic and aromatic or R 1 and R 2 together form an aliphatic ring, and R 3 is a divalent organic radical selected from the group consisting of alkylene, ether-linked alkylene, ether-linked arylene, alkylene amino-linked alkylene, alkylene amino-linked cycloalkylene, cycloalkylene, polycycloalkylene, arylene, alkylarylene bis(alkyl)cycloalkylene and bis(alkyl)polycycloalkylene, (b) bisalkoxy groups of the formula: --O--R.sub.3 --O-- wherein R 3 is a divalent organic radical as before defined, (c) carboxylic acid groups at least a part of which are α,β-unsaturated carboxylic groups with any remainder being saturated aliphatic carboxylic groups, aromatic carboxylic groups or mixtures thereof, (B) at least one terminal group of said polyesteramide being a norbornyl radical.
Claim 3
Dependent Claim
15 words
The modified polyesteramide of claim 1 wherein said diamino groups are from an aliphatic diamine.
Claim 4
Dependent Claim
12 words
The modified polyesteramide of claim 2 wherein said diamine is ethylene diamine.
Claim 5
Dependent Claim
11 words
The modified polyesteramide of claim 2 wherein said diamine is 1,6-hexanediamine.
Claim 6
Dependent Claim
15 words
The modified polyesteramide of claim 1 wherein said amino groups are from a cycloaliphatic diamine.
Claim 7
Dependent Claim
11 words
The modified polyesteramide of claim 5 wherein said diamine is piperazine.
Claim 8
Dependent Claim
11 words
The modified polyesteramide of claim 5 wherein said diamine is homopiperazine.
Claim 9
Dependent Claim
11 words
The modified polyesteramide of claim 5 wherein said diamine is 4,4'-methylenebis(cyclohexylamine).
Claim 10
Dependent Claim
11 words
The modified polyesteramide of claim 5 wherein said diamine is 2,2'-bis(4-aminocyclohexyl)propane.
Claim 11
Dependent Claim
15 words
The modified polyesteramide of claim 1 wherein said amino groups are from a polycycloaliphatic diamine.
Claim 12
Dependent Claim
11 words
The modified polyesteramide of claim 10 wherein said diamine is bis(aminomethyl)dicyclopentadiene.
Claim 13
Dependent Claim
11 words
The modified polyesteramide of claim 10 wherein said diamine is bis(aminomethyl)norborane.
Claim 14
Dependent Claim
15 words
The modified polyesteramide of claim 1 wherein said amino groups are from an aromatic diamine.
Claim 15
Dependent Claim
11 words
The modified polyesteramide of claim 13 wherein said diamine is 4,4'-diaminodiphenylether.
Claim 16
Dependent Claim
17 words
The modified polyesteramide of claim 1 wherein said amino groups are from an ether linked alkylene diamine.
Claim 17
Dependent Claim
11 words
The modified polyesteramide of claim 15 wherein said diamine is bis(2-aminomethyl)ether.
Claim 18
Dependent Claim
14 words
The modified polyesteramide of claim 1 wherein said amino groups are from a polyamine.
Claim 19
Dependent Claim
11 words
The modified polyesteramide of claim 17 wherein said polyamine is diethylenetriamine.
Claim 20
Dependent Claim
11 words
The modified polyesteramide of claim 17 wherein said polyamine is aminoethylpiperazine.
Claim 21
Dependent Claim
20 words
The modified polyesteramide of claim 1 wherein said bisoxo group is from an aliphatic glycol or mixture of aliphatic glycols.
Claim 22
Dependent Claim
14 words
The modified polyesteramide of claim 20 wherein said bisoxo group is from propylene glycol.
Claim 23
Dependent Claim
14 words
The modified polyesteramide of claim 20 wherein said bisoxo group is from neopentyl glycol.
Claim 24
Dependent Claim
20 words
The modified polyesteramide of claim 20 wherein said bisoxo group is from a mixture of propylene glycol and dipropylene glycol.
Claim 25
Dependent Claim
20 words
The modified polyesteramide of claim 20 wherein said bisoxo group is from a mixture of propylene glycol and diethylene glycol.
Claim 26
Dependent Claim
15 words
The modified polyesteramide of claim 1 wherein said bisoxo group is from a polycycloaliphatic glycol.
Claim 27
Dependent Claim
14 words
The modified polyesteramide of claim 25 wherein said bisoxo group is from dicyclopentadiene dimethanol.
Claim 28
Dependent Claim
14 words
The modified polyesteramide of claim 1 wherein said bisoxo group is from bis(hydroxypropyl)bisphenol A.
Claim 29
Dependent Claim
21 words
The modified polyesteramide of claim 1 wherein said bisoxo groups are from a mixture of an aliphatic glycol and aliphatic polyol.
Claim 30
Dependent Claim
19 words
The modified polyesteramide of claim 28 wherein said bisoxo groups are from a mixture of propylene glycol and pentaerythritol.
Claim 31
Dependent Claim
13 words
The modified polyesteramide of claim 1 wherein said norbornyl radical is from dicyclopentadiene.
Claim 32
Dependent Claim
20 words
The modified polyesteramide of claim 1 wherein said norbornyl radical is from a dicyclopentadiene concentrate containing Diels-Alder dimers of diolefins.
Claim 33
Dependent Claim
13 words
The modified polyesteramide of claim 1 wherein said norbornyl radical is from polycyclopentadiene.
Claim 34
Dependent Claim
13 words
The modified polyesteramide of claim 1 wherein said norbornyl radical is from norbornene.
Claim 35
Dependent Claim
14 words
The modified polyesteramide of claim 1 wherein said α,β-unsaturated dicarboxylic acid group is maleoyl.
Claim 36
Dependent Claim
20 words
The modified polyesteramide of claim 1 wherein said α,β-unsaturated dicarboxylic acid groups are a mixture of maleoyl and phthaloyl groups.
Claim 37
Dependent Claim
16 words
The modified polyesteramide of claim 1 wherein said α,β-unsaturated dicarboxylic acid groups are maleoyl and isophthaloyl.
Claim 38
Dependent Claim
14 words
The modified polyesteramide of claim 1 wherein said α,β-unsaturated dicarboxylic acid group is fumaroyl.
Claim 39
Dependent Claim
9 words
The modified polysteramide of claim 1 containing hydroquinone inhibitor.
Claim 40
Dependent Claim
10 words
The modified polyesteramide of claim 1 containing 2,5-di-t-butyl hydroquinone inhibitor.
Claim 41
Dependent Claim
13 words
A formulation of the modified polyesteramide of claim 1 and an unsaturated monomer.
Claim 42
Dependent Claim
10 words
A formulation of claim 40 wherein said monomer is styrene.
Claim 43
Dependent Claim
9 words
A cured composition of the formulation of claim 40.
Claim 44
Dependent Claim
9 words
A formulation of claim 42 containing a reinforcing agent.
Claim 45
Dependent Claim
38 words
A process for making modified unsaturated polyesteramides wherein a mixture of norbornene or a norbornene derivative is reacted with an α,β-unsaturated polycarboxylic acid, anhydride, or mixture thereof, a diamine, or polyamine, and a glycol, or a glycol-polyol mixture.
Claim 46
Dependent Claim
38 words
A process for making modified unsaturated polyesteramides wherein a mixture of norbornene or a norbornene derivative is reacted with an α,β-unsaturated polycarboxylic acid, anhydride, or mixture thereof, a diamine, or polyamine, and a glycol, or a glycol-polyol mixture.
Claim 47
Dependent Claim
13 words
The process of claim 44 wherein water is additionally included as a reactant.
Claim 48
Dependent Claim
29 words
The process of claim 44 or 45 wherein a saturated or aromatic polycarboxylic acid, anhydride or mixture thereof replaces a part of the α,β-unsaturated acid, anhydride or mixture thereof.
Claim 49
Dependent Claim
12 words
The process of claim 44 wherein said norbornene derivative is dicyclopentadiene monoalcohol.
Claim 50
Dependent Claim
135 words
The process of claim 45 wherein: (a) an α,β-unsaturated dicarboxylic acid anhydride and a fraction of the stoichiometric equivalent of water are heated to a temperature of from about 60° to 130° C.; (b) an initial fractional equivalent of said norbornene or norbornene derivative is added and allowed to react; (c) one or more additional fractional equivalent of water and norbornene or norbornene derivative is added and allowed to react; (d) additional fractional equivalents of norbornene or norbornene derivative are added and each allowed to react before subsequent addition of the next increment until the desired amount of norbornene or norbornene derivative has been added; (e) the diamine, or polyamine plus the glycol, or polyol or mixture thereof, are added and the temperature maintained from about 110° to 205° C. with continual removal of water.
Claim 51
Dependent Claim
112 words
The process of claim 45 wherein: (a) an α,β-unsaturated dicarboxylic acid anhyride and at least a stoichiometric equivalent of water are heated to a temperature of from about 120° to 125° C.; (b) an initial equivalent of norbornene or norbornene derivative is added and allowed to react; (c) additional fractional equivalents of norbornene or norbornene derivative are added and each allowed to react before subsequent addition of the next increment until the desired amount of norbornene or norbornene derivative has been added; (d) the diamine, or polyamine plus the glycol, or polyol or mixture thereof are added and the temperature maintained from about 110° to 205° C. with continual removal of water.
Claim 52
Dependent Claim
27 words
The process of claim 48 or 49 wherein all of the diamine, or polyamine and the glycol, or polyol or mixture thereof, are added in one step.
Claim 53
Dependent Claim
44 words
The process of claim 48 or 49 wherein all of the glycol or polyol or mixture thereof and a fractional equivalent of the diamine, or polyamine are added initially and allowed to react after which subsequent increments of the diamine, or polyamine are added.
Claim 54
Dependent Claim
24 words
The process of claim 48 or 49 wherein a polyol containing 3 or more hydroxyl groups is separately added after polyesteramidation is substantially complete.
Claim 55
Dependent Claim
18 words
The process of claim 44 or 45 wherein 2,5-di-t-butylhydroquinone is added to the reaction as a process inhibitor.
Claim 56
Dependent Claim
14 words
The process of claim 44 or 45 wherein said diamine is an aliphatic diamine.
Claim 57
Dependent Claim
14 words
The process of claim 44 or 45 wherein said diamine is a cycloaliphatic diamine.
Claim 58
Dependent Claim
14 words
The process of claim 44 or 45 wherein said diamine is a polycycloaliphatic diamine.
Claim 59
Dependent Claim
14 words
The process of claim 44 or 45 wherein said diamine is an aromatic diamine.
Claim 60
Dependent Claim
16 words
The process of claim 44 or 45 wherein said diamine is an ether linked alkylene diamine.
Claim 61
Dependent Claim
15 words
The process of claim 44 or 45 wherein said amino groups are from a polyamine.
Claim 62
Dependent Claim
19 words
The process of claim 44 or 45 wherein said glycol is an aliphatic glycol or mixture of aliphatic glycols.
Claim 63
Dependent Claim
14 words
The process of claim 44 or 45 wherein said glycol is a polycycloaliphatic glycol.
Claim 64
Dependent Claim
16 words
The process of claim 44 or 45 wherein said hydroxyl groups are from a glycol-polyol mixture.
Claim 65
Dependent Claim
14 words
The process of claim 44 or 45 wherein said norbornene derivative is from dicyclopentadiene.
Claim 66
Dependent Claim
14 words
The process of claim 44 or 45 wherein said norbornene derivative is from polycyclopentadiene.
Claim 67
Dependent Claim
14 words
The process of claim 44 or 45 wherein said norbornene derivative is from norbornene.
Claim 68
Dependent Claim
21 words
The process of claim 44 or 45 wherein said norbornene derivative is from a dicyclopentadiene concentrate containing Diels-Alder dimer of diolefin.
Claim 69
Dependent Claim
15 words
The process of claim 44 or 45 wherein said α,β-unsaturated dicarboxylic acid group is maleoyl.
Claim 70
Dependent Claim
16 words
The process of claim 44 or 45 wherein said α,β-unsaturated dicarboxylic acid is maleoyl and phthaloyl.
Claim 71
Dependent Claim
16 words
The process of claim 44 or 45 wherein said α,β-unsaturated dicarboxylic acid is maleoyl and isophthaloyl.
Claim 72
Dependent Claim
14 words
The process of claim 44 or 45 wherein said α,β-unsaturated dicarboxylic acid is fumaroyl.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-10-17 | 1987-04-18 | 1987-10-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-17 | 1991-04-18 | 1991-10-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-17 | 1995-04-18 | 1995-10-18 | $7700.00 | Window Closed / Lapsed |