DE1495336A1 - Verfahren zur Herstellung von Polyamiden der Iso- und Terephthalsaeure in feinkoerniger Form - Google Patents
Verfahren zur Herstellung von Polyamiden der Iso- und Terephthalsaeure in feinkoerniger FormInfo
- Publication number
- DE1495336A1 DE1495336A1 DE19631495336 DE1495336A DE1495336A1 DE 1495336 A1 DE1495336 A1 DE 1495336A1 DE 19631495336 DE19631495336 DE 19631495336 DE 1495336 A DE1495336 A DE 1495336A DE 1495336 A1 DE1495336 A1 DE 1495336A1
- Authority
- DE
- Germany
- Prior art keywords
- terephthalic acid
- diphenyl
- mol
- polyamides
- fine
- Prior art date
- 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.)
- Pending
Links
- 239000004952 Polyamide Substances 0.000 title claims description 22
- 229920002647 polyamide Polymers 0.000 title claims description 22
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 title claims description 17
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 15
- -1 diphenyl ester Chemical class 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 9
- FHESUNXRPBHDQM-UHFFFAOYSA-N diphenyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FHESUNXRPBHDQM-UHFFFAOYSA-N 0.000 claims description 8
- HPGJOUYGWKFYQW-UHFFFAOYSA-N diphenyl benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OC=2C=CC=CC=2)C=CC=1C(=O)OC1=CC=CC=C1 HPGJOUYGWKFYQW-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 7
- 150000004985 diamines Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 241001501536 Alethe Species 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000009833 condensation Methods 0.000 description 13
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000005494 condensation Effects 0.000 description 6
- 229920006123 polyhexamethylene isophthalamide Polymers 0.000 description 6
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
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
- C08G69/28—Preparatory processes
- C08G69/30—Solid state polycondensation
-
- 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
-
- 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
- C08G69/28—Preparatory processes
-
- 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
- C08G69/34—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids using polymerised unsaturated fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0031683 | 1963-12-17 | ||
| DEC0033573 | 1964-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1495336A1 true DE1495336A1 (de) | 1969-02-27 |
Family
ID=25969807
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631495336 Pending DE1495336A1 (de) | 1963-12-17 | 1963-12-17 | Verfahren zur Herstellung von Polyamiden der Iso- und Terephthalsaeure in feinkoerniger Form |
| DE19641495376 Pending DE1495376A1 (de) | 1963-12-17 | 1964-08-05 | Verfahren zur Herstellung von Polyamiden der durch Alkylgruppen oder durch Halogen-substituierten Iso- und Terephthalsaeure in feinkoerniger Form |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641495376 Pending DE1495376A1 (de) | 1963-12-17 | 1964-08-05 | Verfahren zur Herstellung von Polyamiden der durch Alkylgruppen oder durch Halogen-substituierten Iso- und Terephthalsaeure in feinkoerniger Form |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3379695A (en, 2012) |
| AR (1) | AR142945A1 (en, 2012) |
| AT (1) | AT251882B (en, 2012) |
| BE (1) | BE657202A (en, 2012) |
| CH (1) | CH448521A (en, 2012) |
| DE (2) | DE1495336A1 (en, 2012) |
| DK (1) | DK108696C (en, 2012) |
| FI (1) | FI42378C (en, 2012) |
| FR (1) | FR1416844A (en, 2012) |
| GB (1) | GB1021608A (en, 2012) |
| NL (1) | NL136655C (en, 2012) |
| SE (1) | SE309325B (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495375A1 (de) * | 1964-08-05 | 1969-03-27 | Witten Gmbh Chem Werke | Verfahren zur Herstellung von Polyamiden aliphatischer oder cycloaliphatischer Dicarbonsaeuren in feinkoerniger Form |
| DE1495393B2 (de) * | 1964-11-12 | 1979-10-18 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Polyamiden aus Methylestern der Tere- und/oder Isophthalsäure und alipatischen primären Diaminen |
| DE1546868A1 (de) * | 1965-04-24 | 1970-11-26 | Witten Gmbh Chem Werke | Verfahren zur Schmelzbeschichtung von Metallen mit Polyamiden in Pulverform |
| BE683232A (en, 2012) * | 1965-07-01 | 1966-12-27 | ||
| DE1595495A1 (de) * | 1966-04-01 | 1970-03-26 | Witten Gmbh Chem Werke | Verfahren zur Herstellung von Mischpolyamiden der Tere- und Isophthalsaeure mit alipatischen Dicarbonsaeuren in feinkoerniger Form |
| US3962400A (en) * | 1967-10-28 | 1976-06-08 | Dynamit Nobel Aktiengesellschaft | Injection molding of polyamides prepared from terephthalic acid mono- or di-methyl esters and 2,2,4-and/or 2,4,4-trimethylhexamethylenediamine |
| US3790423A (en) * | 1971-11-22 | 1974-02-05 | Phillips Petroleum Co | Method of bonding using a polyamide resin |
| US3901854A (en) * | 1971-12-09 | 1975-08-26 | Celanese Corp | Two stage process for preparing aromatic polyamides |
| US3865899A (en) * | 1973-06-01 | 1975-02-11 | Unifilm Corp | Flatting compositions |
| US3941755A (en) * | 1973-07-12 | 1976-03-02 | Monsanto Company | Fiber-forming 6TA/6IA copolymers |
| US4022756A (en) * | 1973-08-29 | 1977-05-10 | Monsanto Company | Dimensionally stable 6TA/6IA fibers |
| US4182844A (en) * | 1974-01-02 | 1980-01-08 | The C.P. Hall Company | Preparation of polyaminoamide resin in the absence of water |
| DE2627342A1 (de) * | 1976-06-18 | 1977-12-22 | Dynamit Nobel Ag | Verfahren zur herstellung von gegebenenfalls modifiziertem poly- (alkylpentamethylenterephthalamid) |
| DE2743515A1 (de) * | 1977-09-28 | 1979-04-05 | Bayer Ag | Polyamide aus isophthalsaeure und hexamethylendiamin |
| US4567249A (en) * | 1983-11-18 | 1986-01-28 | General Electric Company | Melt preparation of polyamide by amide ester interchange |
| JPH0645753B2 (ja) * | 1985-02-21 | 1994-06-15 | 三井石油化学工業株式会社 | ポリアミド組成物 |
| US5028462A (en) * | 1989-07-21 | 1991-07-02 | Amoco Corporation | Molded bottles and method of producing same |
| US5175238A (en) * | 1989-07-21 | 1992-12-29 | Amoco Corporation | Polyamide having improved gas barrier properties from adipic acid, isophthalic acid and m-xylylene diamine |
| US5079339A (en) * | 1989-07-31 | 1992-01-07 | Allied-Signal Inc. | Copolymer of dodecane terephthalamide |
| US5081223A (en) * | 1990-02-27 | 1992-01-14 | Amoco Corporation | Amorphous polyamide from neopentyl diamine |
| US5102312A (en) * | 1990-08-30 | 1992-04-07 | Butterworth Jetting System, Inc. | Pump head |
| RU2245345C1 (ru) * | 2003-04-30 | 2005-01-27 | Байкальский институт природопользования Сибирского отделения Российской академии наук (БИП СО РАН) | Способ получения ароматических полиамидов |
| DK1994075T3 (da) * | 2006-03-08 | 2009-12-07 | Basf Se | Delvist aromtiske copolyamider med höj krystallinitet |
| FR3030537B1 (fr) * | 2014-12-22 | 2018-08-17 | Arkema France | Fabrication de poudres de polyamide par aminolyse d'ester |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2130948A (en) * | 1937-04-09 | 1938-09-20 | Du Pont | Synthetic fiber |
| GB614625A (en) * | 1944-07-04 | 1948-12-20 | Geoffrey William Ison Sheavyn | Improvements in the production of condensation polymers |
| US2987507A (en) * | 1957-11-26 | 1961-06-06 | California Research Corp | Preparation of nylon polymers |
| US3194794A (en) * | 1960-01-27 | 1965-07-13 | Eastman Kodak Co | Process of preparing polymers of nuclearly polychlorinated aromatic dicarboxylic acids and diamines having at least 4 carbons |
| NL270423A (en, 2012) * | 1960-10-20 |
-
1963
- 1963-12-17 DE DE19631495336 patent/DE1495336A1/de active Pending
-
1964
- 1964-08-05 DE DE19641495376 patent/DE1495376A1/de active Pending
- 1964-09-28 CH CH1256764A patent/CH448521A/de unknown
- 1964-10-06 AT AT850764A patent/AT251882B/de active
- 1964-10-26 NL NL6412435A patent/NL136655C/xx active
- 1964-11-12 SE SE13642/64A patent/SE309325B/xx unknown
- 1964-11-27 DK DK585064AA patent/DK108696C/da active
- 1964-12-01 GB GB48802/64A patent/GB1021608A/en not_active Expired
- 1964-12-08 FR FR997767A patent/FR1416844A/fr not_active Expired
- 1964-12-09 FI FI642604A patent/FI42378C/fi active
- 1964-12-16 BE BE657202D patent/BE657202A/xx unknown
- 1964-12-16 US US418883A patent/US3379695A/en not_active Expired - Lifetime
-
1965
- 1965-02-11 AR AR142945D patent/AR142945A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| FI42378B (en, 2012) | 1970-03-31 |
| GB1021608A (en) | 1966-03-02 |
| BE657202A (en, 2012) | 1965-04-16 |
| NL136655C (en, 2012) | 1973-02-15 |
| AT251882B (de) | 1967-01-25 |
| AR142945A1 (en, 2012) | 1965-02-11 |
| SE309325B (en, 2012) | 1969-03-17 |
| DK108696C (da) | 1968-01-29 |
| FI42378C (fi) | 1970-07-10 |
| CH448521A (de) | 1967-12-31 |
| FR1416844A (fr) | 1965-11-05 |
| US3379695A (en) | 1968-04-23 |
| NL6412435A (en, 2012) | 1965-06-18 |
| DE1495376A1 (de) | 1969-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |