Patent US4119615A successfully refreshed from Google Patents.
US4119615A
Expired / Lapsed
US
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Thermoplastic adhesive polyoxamide from polyoxypropylene polyamine
Assignee: Huntsman Corp
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Filing: 1976-09-24
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Granted: 1978-10-10
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Expires: 1996-09-24
Abstract
Abstract Covers a novel thermoplastic adhesive composition comprising a polyoxamide formed by reacting a polyoxypropylene polyamine selected from the group consisting of diamines, triamines and mixtures thereof, and having an average molecular weight of about 190 to about 3,000 with oxalic acid to form a liquid prepolymer, said prepolymer being further reacted with a diamine having the formula: NH.sub.2 -- R -- NH.sub.2 where R is a divalent hydrocarbon radical containing 2-18 carbon atoms to form said resinous polyoxamide. Also covers a method of preparing said thermoplastic adhesive compound by reacting oxalic acid with a polyoxypropylene polyamine to form a prepolymer and thereafter reacting said prepolymer with a diamine such as an alkylene diamine to form said adhesive. Other components, e.g., a minor amount of polyepoxide resin having an epoxide equivalent weight of about 150 to about 600, a compatible plasticizing agent, filler and the like may be added to the polyoxamide to provide a formulated thermoplastic adhesive composition having a broad range of hardness, flexibility and compatibility, capable of bonding together a variety of substrates.
Inventors
- 👤 Heinz Schulze
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 14:13
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/40; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31725
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
96 words
A resinous polyoxamide thermoplastic adhesive formed by reacting one mole of a polyoxypropylene polyamine selected from the group consisting of diamines, triamines and mixtures thereof, and having an average molecular weight of about 190 to about 3,000 with 1-4 moles of oxalic acid or a lower alkyl mono or diester of oxalic acid to form a liquid prepolymer, 1 mole of said prepolymer being further reacted with 0.5-1.5 mole of a diamine having the formula: NH.sub.2 -- R - HN.sub.2 where R is a divalent hydrocarbon radical containing 2-18 carbon atoms to form said resinous polyoxamide.
Claim 2
Dependent Claim
96 words
A resinous polyoxamide thermoplastic adhesive formed by reacting one mole of a polyoxypropylene polyamine selected from the group consisting of diamines, triamines and mixtures thereof, and having an average molecular weight of about 190 to about 3,000 with 1-4 moles of oxalic acid or a lower alkyl mono or diester of oxalic acid to form a liquid prepolymer, 1 mole of said prepolymer being further reacted with 0.5-1.5 mole of a diamine having the formula: NH.sub.2 -- R - HN.sub.2 where R is a divalent hydrocarbon radical containing 2-18 carbon atoms to form said resinous polyoxamide.
Claim 3
Dependent Claim
16 words
The resinous polyoxamide of claim 1 which has a melting point less than about 250° C.
Claim 4
Dependent Claim
14 words
The resinous polyoxamide of claim 2 which has a melting point of 80°-250° C.
Claim 5
Dependent Claim
55 words
A thermoplastic adhesive resinous polyoxamide characterized by the following repeating units: ##STR11## where R is a divalent hydrocarbon radical containing 2-18 carbon atoms, y is a number ranging from about 2 to about 40, z is a number ranging from about 1 to 10 and n is a number ranging from about 2 to 20.
Claim 6
Dependent Claim
55 words
A thermoplastic adhesive resinous polyoxamide characterized by the following repeating units: ##STR11## where R is a divalent hydrocarbon radical containing 2-18 carbon atoms, y is a number ranging from about 2 to about 40, z is a number ranging from about 1 to 10 and n is a number ranging from about 2 to 20.
Claim 7
Dependent Claim
20 words
The resinous polyoxamide of claim 4 which is further characterized as having a melting point less than about 250° C.
Claim 8
Dependent Claim
14 words
The resinous polyoxamide of claim 5 which has a melting point of 80°-250° C.
Claim 9
Dependent Claim
18 words
The resinous polyoxamide of claim 4 wherein y is a number ranging from about 2 to about 20.
Claim 10
Dependent Claim
10 words
The resinous polyoxamide of claim 4 wherein R is hexamethylene.
Claim 11
Dependent Claim
10 words
The resinous polyoxamide of claim 4 wherein R is ethylene.
Claim 12
Dependent Claim
108 words
A process of preparing a resinous polyoxamide thermoplastic adhesive composition which comprises the steps of reacting 1 mole of a polyoxypropylene polyamine selected from the group consisting of diamines, triamines and mixtures thereof and having an average molecular weight of about 190 to about 3,000 with 1-4 moles of oxalic acid or an ester of oxalic acid at 75°-150° C. to form a prepolymer, and reacting 1 mole of said prepolymer with 0.5-1.5 moles of a diamine having the formula: NH.sub.2 -- R -- NH.sub.2 where R is a divalent hydrocarbon radical containing 2-18 carbon atoms at a temperature ranging from about 100° C. to about 250° C.
Claim 13
Dependent Claim
108 words
A process of preparing a resinous polyoxamide thermoplastic adhesive composition which comprises the steps of reacting 1 mole of a polyoxypropylene polyamine selected from the group consisting of diamines, triamines and mixtures thereof and having an average molecular weight of about 190 to about 3,000 with 1-4 moles of oxalic acid or an ester of oxalic acid at 75°-150° C. to form a prepolymer, and reacting 1 mole of said prepolymer with 0.5-1.5 moles of a diamine having the formula: NH.sub.2 -- R -- NH.sub.2 where R is a divalent hydrocarbon radical containing 2-18 carbon atoms at a temperature ranging from about 100° C. to about 250° C.
Claim 14
Dependent Claim
18 words
The process of claim 10 wherein said thermoplastic adhesive composition has a melting point less than 250° C.
Claim 15
Dependent Claim
15 words
The process of claim 11 wherein said composition has a melting point of 80°-250° C.
Claim 16
Dependent Claim
31 words
The process of claim 10 wherein 1-2 moles of oxalic acid are reacted with 1 mole of polyoxypropylene polyamine, and 0.5-1 moles of diamine are reacted with 1 mole of prepolymer.
Claim 17
Dependent Claim
157 words
A process of preparing a resinous polyoxamide thermoplastic adhesive composition characterized by the following repeating units: ##STR12## where R is a divalent hydrocarbon radical containing 2-18 carbon atoms, y is a number ranging from about 2 to about 40, z is a number ranging from about 1 to 10 and n is a number ranging from about 2 to 20, which comprises the steps of reacting 1-4 moles of oxalic acid or an ester of oxalic acid at 75°-150° C. with 1 mole of a polyoxypropylene diamine having the following structural formula: ##STR13## where y has a significance as expressed above, to form a liquid prepolymer, reacting said prepolymer with a diamine having the formula NH.sub.2 -- R -- NH.sub.2 where R is a divalent hydrocarbon radical radial containing 2-18 carbon atoms in a mole ratio of 0.5-1.5 moles of diamine per mole of prepolymer at a temperature of 100°-250° C. to provide said thermoplastic adhesive compound.
Claim 18
Dependent Claim
157 words
A process of preparing a resinous polyoxamide thermoplastic adhesive composition characterized by the following repeating units: ##STR12## where R is a divalent hydrocarbon radical containing 2-18 carbon atoms, y is a number ranging from about 2 to about 40, z is a number ranging from about 1 to 10 and n is a number ranging from about 2 to 20, which comprises the steps of reacting 1-4 moles of oxalic acid or an ester of oxalic acid at 75°-150° C. with 1 mole of a polyoxypropylene diamine having the following structural formula: ##STR13## where y has a significance as expressed above, to form a liquid prepolymer, reacting said prepolymer with a diamine having the formula NH.sub.2 -- R -- NH.sub.2 where R is a divalent hydrocarbon radical radial containing 2-18 carbon atoms in a mole ratio of 0.5-1.5 moles of diamine per mole of prepolymer at a temperature of 100°-250° C. to provide said thermoplastic adhesive compound.
Claim 19
Dependent Claim
18 words
The process of claim 14 wherein said thermoplastic adhesive composition has a melting point less than 250° C.
Claim 20
Dependent Claim
17 words
The process of claim 14 wherein said thermoplastic adhesive composition has a melting point of 80°-250° C.
Claim 21
Dependent Claim
34 words
The process of claim 14 wherein 1-2 moles of oxalic acid or ester of oxalic acid are reacted per mole of polyoxypropylene diamine and 0.5-1 mole of diamine is reacted per mole of prepolymer.
Claim 22
Dependent Claim
9 words
The process of claim 14 wherein R is hexamethylene.
Claim 23
Dependent Claim
9 words
The process of claim 14 where R is ethylene.
References Cited (Backward Citations)
US3882090A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-09 | 1982-04-10 | 1982-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-09 | 1986-04-10 | 1986-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-09 | 1990-04-10 | 1990-10-10 | $7700.00 | Window Closed / Lapsed |