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US4055525A Expired / Lapsed US ⏱️ 0.0 years remaining

Novel polyamide adhesives and method of preparation

Assignee: Union Camp Corp
•
Filing: 1976-06-23
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Granted: 1977-10-25
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Expires: 1996-06-23
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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.

References Cited (Backward Citations)

US2891084A Cited
US3206438A Cited
US3700618A Cited
US3793270A Cited
US3781234A Cited
US3847875A Cited
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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

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