US4055525A
Expired / Lapsed
US
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Novel polyamide adhesives and method of preparation
Assignee: Union Camp Corp
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Filing: 1976-06-23
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Granted: 1977-10-25
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Expires: 1996-06-23
Abstract
Abstract Novel polyamide hot melt adhesive compositions are disclosed together with a novel method of preparation. The process of the invention comprises condensation of hexamethylene diamine with an acid mixture of specific aliphatic C 19 dicarboxylic acids, aliphatic C 6 -C 10 dicarboxylic acids and a specific class of C 2 -C 27 monocarboxylic acids. The process is carried out initially in aqueous solvent and in the presence of a catalyst selected from phosphoric acid, magnesium oxide and calcium oxide. The adhesive compositions are particularly useful in adhering poromerics such as natural and synthetic leather goods. The compositions of the invention are also useful adhesives for adhering metals.
Inventors
- 👤 Thomas T. Cheng
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 20:24
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/26; C08G69/265
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
199 words
The polyamide obtained on condensation of substantially equivalent proportions of hexamethylene diamine and a mixture of acids, said mixture comprising aliphatic dicarboxylic acids of the formula: ##STR2##wherein X and Z are integers of from 0 to 15, inclusive, y is an integer of from 0 to 1 and the sum of X + y + Z is 15; aliphatic dicarboxylic acids of the formula: HOOC--R--COOH (II) wherein R represents alkylene of 4 to 8 carbon atoms, inclusive and monocarboxylic acids of the formula: R'--COOH (III) wherein R' is selected from the group consisting of alkyl having 1 to 21 carbon atoms, inclusive, phenyl and hydroxy-substituted phenyl; the ratio of the moles of the acid of formula (I) to the moles of acid of formula (II) in said mixture being in the range of from 1-2:1 and the ratio of the sum of the moles of acids of formulae (I) and (II) to the moles of formula (III) being from 1:0.0-0.08; said condensation being carried out in the presence of a catalytic proportion of a catalyst selected from the group consisting of phosphoric acid, magnesium oxide and calcium oxide and in the presence of an excess of an aqueous solvent.
Claim 2
Dependent Claim
199 words
The polyamide obtained on condensation of substantially equivalent proportions of hexamethylene diamine and a mixture of acids, said mixture comprising aliphatic dicarboxylic acids of the formula: ##STR2##wherein X and Z are integers of from 0 to 15, inclusive, y is an integer of from 0 to 1 and the sum of X + y + Z is 15; aliphatic dicarboxylic acids of the formula: HOOC--R--COOH (II) wherein R represents alkylene of 4 to 8 carbon atoms, inclusive and monocarboxylic acids of the formula: R'--COOH (III) wherein R' is selected from the group consisting of alkyl having 1 to 21 carbon atoms, inclusive, phenyl and hydroxy-substituted phenyl; the ratio of the moles of the acid of formula (I) to the moles of acid of formula (II) in said mixture being in the range of from 1-2:1 and the ratio of the sum of the moles of acids of formulae (I) and (II) to the moles of formula (III) being from 1:0.0-0.08; said condensation being carried out in the presence of a catalytic proportion of a catalyst selected from the group consisting of phosphoric acid, magnesium oxide and calcium oxide and in the presence of an excess of an aqueous solvent.
Claim 3
Dependent Claim
21 words
The polyamide of claim 1 wherein said acid of formula (I) is the isomeric mixture obtained upon carboxylation of oleic acid.
Claim 4
Dependent Claim
28 words
The polyamide of claim 1 wherein said acid of formula (I) is provided in the crude mixture obtained upon carboxylation of a partially hydrogenated tall oil fatty acid.
Claim 5
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (II) is adipic acid.
Claim 6
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (II) is azelaic acid.
Claim 7
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (II) is sebacic acid.
Claim 8
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (III) is salicylic acid.
Claim 9
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (III) is oleic acid.
Claim 10
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (III) is palmitic acid.
Claim 11
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (III) is stearic acid.
Claim 12
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (III) is acetic acid,
Claim 13
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (III) is neopentanoic acid.
Claim 14
Dependent Claim
14 words
The polyamide of claim 1 wherein said acid of formula (III) is pelargonic acid.
Claim 15
Dependent Claim
42 words
The polyamide of claim 1 wherein the molar ratio of acids of formula (I) to acids of formula (II) is 2:1 and the molar ratio of the sum of acids of formulae (I) and (II) to acids of formula (III) is 1:0.06.
Claim 16
Dependent Claim
11 words
The polyamide of claim 1 wherein said catalyst is phosphoric acid.
Claim 17
Dependent Claim
11 words
The polyamide of claim 1 wherein said catalyst is calcium oxide.
Claim 18
Dependent Claim
11 words
The polyamide of claim 1 wherein said catalyst is magnesium oxide.
Claim 19
Dependent Claim
23 words
The polyamide of claim 1 wherein said condensation is carried out at a temperature of from about 250° C. to about 300° C.
Claim 20
Dependent Claim
11 words
The polyamide of claim 18 wherein said temperature is 275° C.
Claim 21
Independent Claim
219 words
A method of preparing a polyamide hot-melt adhesive, which comprises; reacting, in the presence of an excess of an aqueous solvent, substantially equivalent proportions of hexamethylene diamine and a mixture of acids, said mixture comprising aliphatic dicarboxylic acids of the formula: ##STR3## wherein X and Z are integers of from 0 to 15, inclusive, y is an integer of from 0 to 1 and the sum of X + y + Z is 15; aliphatic dicarboxylic acids of the formula: HOOC--R--COOH (II) wherein R represents alkylene of 4 to 8 carbon atoms, inclusive and monocarboxylic acids of the formula: R'--COOH (III) wherein R' is selected from the group consisting of alkyl having 1 to 21 carbon atoms, inclusive, phenyl and hydroxy-substituted phenyl; the ratio of moles of acid of formula (I) to the moles of acid of formula (II) in said mixture being in the range of from 1-2:1 and the ratio of the sum of the moles of acids of formulae (I) and (II) to the moles of formula (III) being from 1.0:0.0-0.08; and polymerizing the product of said reacting at a temperature within the range of from about 250° C. to about 300° C. in the presence of a catalytic proportion of a catalyst selected from the class consisting of phosphoric acid, magnesium oxide and calcium oxide.
Claim 22
Independent Claim
219 words
A method of preparing a polyamide hot-melt adhesive, which comprises; reacting, in the presence of an excess of an aqueous solvent, substantially equivalent proportions of hexamethylene diamine and a mixture of acids, said mixture comprising aliphatic dicarboxylic acids of the formula: ##STR3## wherein X and Z are integers of from 0 to 15, inclusive, y is an integer of from 0 to 1 and the sum of X + y + Z is 15; aliphatic dicarboxylic acids of the formula: HOOC--R--COOH (II) wherein R represents alkylene of 4 to 8 carbon atoms, inclusive and monocarboxylic acids of the formula: R'--COOH (III) wherein R' is selected from the group consisting of alkyl having 1 to 21 carbon atoms, inclusive, phenyl and hydroxy-substituted phenyl; the ratio of moles of acid of formula (I) to the moles of acid of formula (II) in said mixture being in the range of from 1-2:1 and the ratio of the sum of the moles of acids of formulae (I) and (II) to the moles of formula (III) being from 1.0:0.0-0.08; and polymerizing the product of said reacting at a temperature within the range of from about 250° C. to about 300° C. in the presence of a catalytic proportion of a catalyst selected from the class consisting of phosphoric acid, magnesium oxide and calcium oxide.
Claim 23
Dependent Claim
23 words
The method of claim 20 wherein said reacting is carried out at a temperature of from about 60° C. to about 200° C.
Claim 24
Dependent Claim
17 words
The method of claim 20 wherein said reacting is from about 125° C to about 150° C.
Claim 25
Dependent Claim
13 words
The method of claim 20 wherein phosphoric acid is present in said mixture.
Claim 26
Dependent Claim
21 words
The method of claim 20 wherein said polymerizing is carried out at a temperature of about 275° C. to 300° C.
Claim 27
Dependent Claim
11 words
The method of claim 20 wherein said mixture includes an antioxidant.
Claim 28
Dependent Claim
11 words
The method of claim 20 carried out in an inert atmosphere.
Claim 29
Dependent Claim
24 words
The method of claim 20 wherein said catalytic proportion is within the range of from 0.1 to 5 percent by weight of the reactants.
Claim 30
Dependent Claim
25 words
The method of claim 27 wherein said proportion is within the range of from about 0.3 to 3 percent by weight of the diamine reactant.
Claim 31
Dependent Claim
11 words
The method of claim 28 wherein said catalyst is phosphoric acid.
Claim 32
Dependent Claim
11 words
The method of claim 28 wherein said catalyst is magnesium oxide.
Claim 33
Dependent Claim
11 words
The method of claim 28 wherein said catalyst is calcium oxide.
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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) | 1980-10-24 | 1981-04-25 | 1981-10-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-24 | 1985-04-25 | 1985-10-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-24 | 1989-04-25 | 1989-10-25 | $7700.00 | Window Closed / Lapsed |