AU663327B2 - Creation of Inventions and Patents with Artificial Intelligence

AU663327B2 – Copolyadipamide containing trimethylhexamethyleneadipamide units and products prepared therefrom
– Google Patents

AU663327B2 – Copolyadipamide containing trimethylhexamethyleneadipamide units and products prepared therefrom
– Google Patents
Copolyadipamide containing trimethylhexamethyleneadipamide units and products prepared therefrom

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Publication number
AU663327B2

AU663327B2
AU22360/92A
AU2236092A
AU663327B2
AU 663327 B2
AU663327 B2
AU 663327B2
AU 22360/92 A
AU22360/92 A
AU 22360/92A
AU 2236092 A
AU2236092 A
AU 2236092A
AU 663327 B2
AU663327 B2
AU 663327B2
Authority
AU
Australia
Prior art keywords
document
units
international
copolyadipamide
trimethylhexamethyleneadipamide
Prior art date
1991-06-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Application number
AU22360/92A
Other versions

AU2236092A
(en

Inventor
James Alexander Hammond Jr.
David Neil Marks
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

INVISTA TECHNOLOGIES Sarl

Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1991-06-21
Filing date
1992-06-16
Publication date
1995-10-05

1992-06-16
Application filed by EI Du Pont de Nemours and Co
filed
Critical
EI Du Pont de Nemours and Co

1993-01-25
Publication of AU2236092A
publication
Critical
patent/AU2236092A/en

1995-10-05
Application granted
granted
Critical

1995-10-05
Publication of AU663327B2
publication
Critical
patent/AU663327B2/en

2012-06-16
Anticipated expiration
legal-status
Critical

Status
Expired
legal-status
Critical
Current

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Classifications

C—CHEMISTRY; METALLURGY

C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON

C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule

C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids

C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids

C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids

Description

OPI DATE ’25/01/93 APPLN. ID 22360/92 AOJP DATE 25/03/93 PCT NUMBER PCT/US92/04828 111111IIIIllll1111111111111111111 Ill1111 AU9222360
.PCT)
(51) International Patent Classification 5 C08G 69/26 (11) International Publication Number: AI (43) International Publication Date: WO 91/00384 7 January 1993 (07.01.93) (21) International Application Number: (22) International Filing Date: Priority data: 718,940 21 June 1 PCT/US92/04828 16 June 1992 (16.06.92) (81) Designated States: AU, BR, CA, European patent (AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LU, MC, NL,
SE).
Published With international search report. 991 (21.06.91) (71) Applicant: E. I. DU PONT DE NEMOURS AND COM- PANY [US/US]; 1007 Market Street, Wilmington, DE 19898 (US).
(72) Inventors: HAMMOND, James, Alexander, Jr. 1020 Lakeshore Lane. Chattanooga. TN 37415 MARKS.
David, Neil 1007 Cypress Road, Wilmington, DE 19810 (US).
(74) Agents: HENDRICKSON. John. S. et al.; E.I. du Pont de Nemours and Company, Legal ‘Patent Records Center, 1007 Market Street, Wilmington. DE 19898 (US).
e’ (54)Title: COPOLYADIPAMIDE CONTAINING TRIMETHYLHEXAMETHYLENEADIPAMIDE UNITS AND PRO- DUCTS PREPARED THEREFROM (57) Abstract A copolyadipamide consisting essentially of between about 60 and about 99.5 mole percent hexamethyleneadipamide units and between about 0.5 and 40 mole percent trimethylhexamethyleneadipamide units, the copolyadipamide having an RV greater than about 25, and a melting point of greater than about 220 °C.
WO 93/00384 PCT/US92/04828 Copolyadipamide Containing Trimethylhexamethyleneadipamide Units and Products Prepared Therefrom BACKGROUND OF THE INVENTION The present invention relates to polymers and more particularly to a copolyadipamide having hexamethyleneadipamide units and a minor portion of trimethylhexamethyleneadipamide units, and products prepared therefrom.
Polyadipamide polymers, e.g., polyhexamethyleneadipamide (nylon 66), have a number of positive characteristics, but are quite thermally unstable at their normal processing tenperatures. When kept in the molten state at processing temperature for a long time, polyadipamides form branched/crosslinked, insoluble, nonfusible gel. The formation of gel in the polymer product and on the walls of processing equipment results in deficient product with poor processibility, particularly when fiber spinning is involved. The fiber spinning breaks which may occur are troublesome and make the winding of large yarn packages impractical.
Certain remedies to gel-formation have been reported such as in U.S. Patent No. 3,872,055. U.S.
Patent No. 3,872,055 discloses a polyamide composition which has a decreased gel-forming property, specifically a copolyamide of the diamine-dicarboxylic acid type containing a phosphinic or phosphonous acid compound together with an alkali metal compound.
SUMMARY OF THE INVENTION In accordance with the invention, there is provided a copolyadipamide consisting essentially of between about 60 and about 99.5 mole percent hexamethyleneadipamide units and between about 0.5 and mole percent trimethylhexainethyleneadipamide units, the copolyamide having an RV greater than about 25, and a melting point of greater than about 220°C. For convenience, the copolyamide of the invention will be referred to as nylon 66/trimethyl66.
WO 93/00384 PCT/US92/04828 In a preferred form of the invention, the copolyadipamide consists essentially of between about and about 99.5 mole percent hexamethyleneadipamide units and between about 0.5 and 10 mole percent trimethylhexamethyleneadipamide units. Preferably, the RV of the copolyamide is between about 30 and about 80, most preferably between about 30 and about The copolyamide of the invention provides a reduced gel formation rate relative to that of nylon 66 and provides improvements in product quality, increases in process continuity, and decreases in equipment maintenance costs.
DETAILED DESCRIPTION The copolyadipamides of the invention are substantially linear copolyamides which consist essentially of between about 60 and about 99.5 mole percent hexamethyleneadipamide units and between about and 40 mole percent trimethylhexamethyleneadipamide (trimethyl66) units. Preferably, the trimethyl66 units are selected from the class consisting of 2,2,4-trimethylhexamethyleneadipamide units, 2,4,4-trimethylhexamethyleneadipamide units, and mixtures thereof. In the preferred copolyadipamides, the trimethyl66 units are generally randomly distributed throughout the copolymer. The copolyamide has properties similar to homopolymer nylon 66, but has significant advantages in product quality, production cost, and processability.
Depending on the intended end use of the copolyadipamides of the invention, it is advantageous to employ varying mole percentages of trimethyl66 in the copolyamide. So that the properties of copolyamide remain similar to the properties of homopolymer poly(hexamethyleneadipamide), it is preferable for the mole percentage of trimethyl66 in the polymer to be between about 0.5 and about The copolyadipamides in accordance with the invention have a formic acid relative viscosity (RV) of M -I WO 93/D0384 PCT/US92/04828 greater than about 25. Preferably, the RV of the copolyadipamide is between about 30 and about 80, most preferably, between about 30 and about The melting point of the copolyadipamides in accordance with the invention is greater than about 220 0
C.
The melting points of the copolyadipamides vary with the percentage of trimethyl66 and thus range very close to the melting point of homopolymer nylon 66 polymer, about 265 0 C, when the percentage of trimethyl66 is about With increasing trimethyl66, the melting point decreases to about 220 0 C where the trimethyl66 percentage is about Surprisingly, the copolyadipamides of the invention have been found to form “gel” at a substantially lower rate than nylon 66 homopolymer. “Gel” refers to the very high molecular weight, branched/crosslinked polymer which forms in the nylon 66 polymer melt and which collects in the product and on equipment walls in contact with the molten polymer. The gel is essentially insoluble and often can only be removed from equipment using extreme measures such as by burning off of the gel. As shown in Table the gelation time (the time required to show an inflection in a melt viscosity vs. heating time plot of a polymer sample maintained at a constant temperature and constant steam pressure) increases significantly with increasing percentages of trimethyl66. In addition, since the melting point of the copolyamide is lower, and is substantially lower at the greater trimethyl66 mole percentages, the gelation time can be further increased without affecting spinning performance by employing lower polymer melt temperatures.
The copolyadipamides of the invention can be prepared by condensation polymerization in an aqueous “salt” solution formed by mixing adipic acid with hexamethylenediamine (HMD) and trimethylhexamethylenediamine (TMHMD) in the molar proportions necessary to produce the copolymer with the desired mole percent of trimethyl66 units. Adapted as
IL.–
WO 93/00384 PCT/US92/04828 necessary to compensate for the different properties of the TMHMD, procedures useful for the production of homopolymer poly(hexamethyleneadipamide) can be applied to the production of the copolymer of the invention.
A particularly convenient method for making a copolyadipamide in accordance with the invention is to provide two aqueous salt solutions of hexamethylene diammonium adipate and trimethylhexamethylene diammonium adipate. Necessary quantities of the two solutions can be readily mixed to produce a salt solution for the desired copolyamide.
It is sometimes desirable to add a catalyst to the salt solution. A variety of catalysts are known for use in polymerizing homopolymer nylon 66 such as phenyl phosphinic acid, manganese hypophosphite, etc. The salt solution with or without catalyst is reacted in a suitable reaction vessel such as an autoclave under an inert atmosphere. One preferred procedure is purging the autoclave with nitrogen and increasing the pressure to about 265 psia. The salt solution is heated to a temperature of about 250°C. The pressure is then released over, for example, one hour while increasing the temperature to about 275 0 C. The reaction temperature is held constant at atmospheric pressure for sufficient time to complete the reaction to the extent desired. The copolyamide can be cooled in the autoclave and ground or can be extruded from the autoclave into water and conveniently chipped and dried to produce flake. The RV of the polymer from the clave can be in the range of 25-80 but is typically in the range of 25-45.
The copolyamide in accordance with the invention can also be made by any of a variety of continuous polymerization processes.
The copolyadipamide is useful in a wide variety of known processes for the manufacture of fibers, films and molded articles. For use of the composition in fibers, any of a variety of known additives such as delustrants, titanium dioxide, antioxidants, pigments, and other
IN.-
I
WO 93/90384 PCT/US92/04828 materials may be added to the copolyamide at a suitable point in the polymer preparation or, for example, as the flake is melted in an extruder in advance of spinning.
The following example is offered for the purposes of illustrating the invention and is not intended to be limiting. Percentages are by weight except for mole percentages of 66 and trimethyl66 monomer units. The test methods which follow were used for obtaining the results reported.
TEST METHODS The formic acid relative viscosity (RV) of the polyamide is measured as described at col. 2, 1. 42-51, in Jennings, U.S. Patent No. 4,702,875.
Amine and carboxyl ends are determined by the methods described on pages 293 and 294 in Volume 17 ci the “Encyclopedia of Industrial Chemical Analysis” published by John Wiley Sons, Inc. in 1973.
The gel time (reported in hours) is the time required to show a sharp inflection and rise in polymer melt viscosity while heating a polymer sample maintained at a constant temperature and constant steam pressure. A plot of polymer melt viscosity versus time will show a rise or inflection in melt viscosity as formation of polymer gel makes the bulk polymer more viscous.
Alternately, gel time can be determined by the method of U.S. Patent No. 3,872,055. This method reports the time required for making the copolyamide insoluble (when only solvent swelling is observed) in anhydrous formic acid after being heated at a given temperature and pressure in a steam atmosphere.
EXAMPLE I Into a 1 gallon autoclave, the following reactants were added in varied amounts as indicated in Table I(a) to provide the indicated mole ratios: nylon 66 salt solution (approximately 50% concentration), adipic acid, and trimethylhexamethylenediamine (TMHMD) with or without water as indicated. The TMHMD used was obtained from American Tokyo Kasei, Inc., 9211 N. Harborgate St., r r ~U WO 93/00384 PCT/US92/04828 Portland OR 97203 and is a mixture of 2,2,4- and 2,4,4trimethylhexamethylenediamines.
TABLE I(a) Nylon 66/ Adipic Nylon Trimethvl66 TMHMD(q) Acid(g) 66 Salt(q) Water(q) 100/0 0 0 2000 0 (51.5%) 95/5 34.8 30.2 2000 0 (51.5%) 85/15 94.4 86.2 1700 0 (51.5%) 65/35 170.3 154.7 1000 150 (51.5%) For each reactant mixture, the autoclave was purged with nitrogen and sealed. The pressure release valve on the clave was set to 265 psia and the clave was heated to 250 0 C. When the temperature reached 250 0 C, the pressure reduction cycle was started so that the pressure was reduced to atmospheric over one hour. At the same time, the temperature of the autoclave was raised to 275 0 C. When the pressure reached atmospheric, it was held for 45 minutes. The molten polymer was removed from the autoclave under nitrogen pressure as a continuous filament and cooled in water. The polymer was subsequently ground to a fine powder and dried at 90 0 C in a vacuum oven over night. Properties of the compositions prepared are reported in Table The gel times of the 66/trimethyl66 copolymers at 292 0 C are given in Table I(c).
_I_
TABLE I (b) End Groups (Eauiv./1 0 6 Relative Nylon 66/trimethvl66 Viscosity Amine Carboxyl 100/0 53 60 56 95/5 52 34 121 85/15 34 49 99 65/35 32 49 86 TABLE 1(c) Nylon 66/trimethvl66 Gel Time, 2920C, Hr.
100/0 15.0 95/5 18.0 85/15 20.0 65/35 31.4 Throughout this specification and the claims which follow, unless the context requires otherwise, the word “comprise”, jr variations such as “comprises” or “comprising”, will be understood to imply the inclusion of a stated integer or group of integers but not the exclusion of any other integer or group of integers.
*e ,v 7/8)5MSAP7489.SI’E.7

Claims (8)

1. A copolyadipamide comprising between 60 and 99.5 mole percent hexamethyleneadipamide units and between 0.5 and 40 mole percent trimethylhexamethyleneadipamide units, said copolyamide having a formic acid RV greater than 25, and a melting point of greater than 220 0 C.

2. A copolyadipamide as claimed in claim 1 wherein said formic acid RV is between 30 and

3. A copolyadipamide as claimed in claim 1 wherein said formic acid RV is between 30 and

4. A copolyadipamide as claimed in any one of claims 1 to 3 wherein said trimethylhexamethyleneadipamide units are selected from 2,2,4-trimethylhexamethyleneadipamide units, 2,4,4-trimethylhexamethyleneadipamide units, and mixtures thereof.

5. A copolyadipamide as claimed in any one of claims 1 to 4 comprising between 90 and 99.5 mole percent hexamethylene adipamide units and between 0.5 and 10 mole percent trimethylhexamethyleneadipamide units.

6. A copolyadipamide as claimed in claim 1 substantially as hereinbefore described with reference to any one of the examples. DATED this 7th day of August, 1995. E I DU PONT DE NEMOURS AND COMPANY By Their Patent Attorneys: CALLINAN LAWRIE 7/895MSA P7489.SPI’.8 L rn INTERNATIONAL SEARCH REPORT International Application No PCT/US 92/04828 1. CLASSIFICATION OF SUBJECT MATTER (If several classification symbols apply, indicate all) 6 According to International Patent Classification (IPC) or to both Nation’ Classification and IPC C 08 G 69/26 U. FIEIDS SEARCHED Minimum Documentation Sea;ched 7 Classification System Classification Symbols C 08 G Documentation Searched other than Minimum Documentation to the Extent that such Documents are Included in the Fields Searched 8 Ill. DOCUMENTS CONSIDERED TO BE RELEVANT 9 Category o Citation of Document, 1I with Indication, where appropriate, of the relevant passages I2 Relevarn to Claim No. 13 A Database WPI, accession no. 75-35118W [21], Derwent Publications Ltd, London, GB, JP,A,50018593 (TOYO SPINNING) 27 February 1975 A FR,A,2371474 (BAYER) 16 June 1978 o Special categories of cited documents 10 later document published after the international filing date or priority date and not In conflict with the application but document defining the general state of the art which Is not cited to understand the principle or theory underlying the considered to be of particular relevance invention earlier document but published on or after the International document of particular relevance; the claimed Invention filing date cannot be considered novel or cannot be considered to document which may throw doubts on priority claim(s) or Involve an inventive step which is cited to establish the publication date of another “Y document of particular relevance; the claimed invention citation or other special reason (as specified) cannot be considered to involve an Inventive step when the document referring to an oral disclosure, use, exhibition or document is combined with one or more other such docu- other means ments, such combination being obvious to a person skilled document published prior to the international filing date but In the art. later than the priority date claimed document member of the same patent family IV. CERTI-1CATION Date of the Actual Completion of the International Search Date of Mailing of this International Search Report 02-09-1992

24. 09.92 International Searching Authorit) Signature of Authorized Officer EUROPEAN PATENT OFFICE A. LEROY Form PCTIISA/210 ecmnd Ishel Jnuary 19& L IL ANNEX TO THE INTERNATIONAL SEARCH REPORT ON INTERNATIONAL PATENT APPLICATION NO. US 9204828 SA 61799 This annex lists the patent family members relating to the patent documents cited in the above-mentioned international search report. The members are as contained in the European Patent Office EDP file on 18/09/92 The European Patent Office is in no way liable for these particulars which are merely given for the purpose of information. Patent document cited in search report Publication date Patent family member(s) Publication date I FR-A- 2371474 16-06-78 DE-A- GB-A- JP-C- JP-A- JP-B- NL-A- US-A- 2652465 1554245 1303415 53064299 60026140 7708391 4250297 24-05-78 17-10-79

28-02-86 08-06-78 21-06-85 22-05-78 10-02-81 c C For mo details about this annex :see Oicil Journal of the European Patent Oie, No. 12/82 1L. I

AU22360/92A
1991-06-21
1992-06-16
Copolyadipamide containing trimethylhexamethyleneadipamide units and products prepared therefrom

Expired

AU663327B2
(en)

Applications Claiming Priority (3)

Application Number
Priority Date
Filing Date
Title

US718940

1991-06-21

US07/718,940

US5185428A
(en)

1991-06-21
1991-06-21
Copolyadipamide containing pentamethyleneadipamide units and products prepared therefrom

PCT/US1992/004828

WO1993000384A1
(en)

1991-06-21
1992-06-16
Copolyadipamide containing trimethylhexamethyleneadipamide units and products prepared therefrom

Publications (2)

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AU2236092A

AU2236092A
(en)

1993-01-25

AU663327B2
true

AU663327B2
(en)

1995-10-05

Family
ID=24888168
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Title
Priority Date
Filing Date

AU22360/92A
Expired

AU663327B2
(en)

1991-06-21
1992-06-16
Copolyadipamide containing trimethylhexamethyleneadipamide units and products prepared therefrom

AU22263/92A
Expired

AU663326B2
(en)

1991-06-21
1992-06-16
Copolyadipamide containing pentamethyleneadipamide units and products prepared therefrom

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Priority Date
Filing Date

AU22263/92A
Expired

AU663326B2
(en)

1991-06-21
1992-06-16
Copolyadipamide containing pentamethyleneadipamide units and products prepared therefrom

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US
(1)

US5185428A
(en)

EP
(2)

EP0590054B1
(en)

AU
(2)

AU663327B2
(en)

BR
(2)

BR9206171A
(en)

CA
(2)

CA2111246A1
(en)

DE
(2)

DE69213455T2
(en)

ES
(2)

ES2090662T3
(en)

MX
(1)

MX9202986A
(en)

WO
(2)

WO1993000384A1
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1991-01-10
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polyamide composition

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1991-06-21
1992-05-05
E. I Du Pont De Nemours And Company
Copolyadipamide containing ethyltetramethyleneadipamide units

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Copolyadipamide containing pentamethyleneadipamide units and products prepared therefrom

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1993-12-07
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Polyamides,heat-sealable layers formed therefrom and packages incorporating them

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军事科学院系统工程研究院军需工程技术研究所
Copolyamide 56/66 polymer and preparation method and application thereof

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2021-06-30
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上海凯赛生物技术股份有限公司
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1991

1991-06-21
US
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patent/US5185428A/en
not_active
Expired – Lifetime

1992

1992-06-16
WO
PCT/US1992/004828
patent/WO1993000384A1/en
active
IP Right Grant

1992-06-16
ES
ES92914184T
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Expired – Lifetime

1992-06-16
CA
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patent/CA2111246A1/en
not_active
Abandoned

1992-06-16
BR
BR9206171A
patent/BR9206171A/en
not_active
IP Right Cessation

1992-06-16
AU
AU22360/92A
patent/AU663327B2/en
not_active
Expired

1992-06-16
WO
PCT/US1992/004830
patent/WO1993000385A1/en
active
IP Right Grant

1992-06-16
DE
DE69213455T
patent/DE69213455T2/en
not_active
Expired – Lifetime

1992-06-16
AU
AU22263/92A
patent/AU663326B2/en
not_active
Expired

1992-06-16
BR
BR9206172A
patent/BR9206172A/en
not_active
IP Right Cessation

1992-06-16
DE
DE69213453T
patent/DE69213453T2/en
not_active
Expired – Lifetime

1992-06-16
EP
EP92914184A
patent/EP0590054B1/en
not_active
Expired – Lifetime

1992-06-16
CA
CA002111245A
patent/CA2111245A1/en
not_active
Abandoned

1992-06-16
ES
ES92914464T
patent/ES2090664T3/en
not_active
Expired – Lifetime

1992-06-16
EP
EP92914464A
patent/EP0592532B1/en
not_active
Expired – Lifetime

1992-06-18
MX
MX9202986A
patent/MX9202986A/en
unknown

Patent Citations (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

AU8060991A
(en)

1990-06-21
1992-01-07
E.I. Du Pont De Nemours And Company
Fiber-forming copolyamide and fibers produced therefrom

AU2226392A
(en)

1991-06-21
1993-01-25
Invista Technologies S.A.R.L.
Copolyadipamide containing pentamethyleneadipamide units and products prepared therefrom

AU657154B2
(en)

1991-06-21
1995-03-02
Invista Technologies S.A.R.L.
Copolyadipamide containing ethyltetramethyleneadipamide units and products prepared therefrom

Also Published As

Publication number
Publication date

WO1993000384A1
(en)

1993-01-07

AU2226392A
(en)

1993-01-25

EP0592532B1
(en)

1996-09-04

ES2090664T3
(en)

1996-10-16

ES2090662T3
(en)

1996-10-16

BR9206172A
(en)

1994-12-27

WO1993000385A1
(en)

1993-01-07

CA2111246A1
(en)

1993-01-07

EP0592532A1
(en)

1994-04-20

AU663326B2
(en)

1995-10-05

AU2236092A
(en)

1993-01-25

DE69213453D1
(en)

1996-10-10

DE69213455D1
(en)

1996-10-10

BR9206171A
(en)

1995-10-10

US5185428A
(en)

1993-02-09

DE69213455T2
(en)

1997-03-13

DE69213453T2
(en)

1997-03-13

MX9202986A
(en)

1993-02-01

EP0590054A1
(en)

1994-04-06

EP0590054B1
(en)

1996-09-04

CA2111245A1
(en)

1993-01-07

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