DE1495375A1 - Verfahren zur Herstellung von Polyamiden aliphatischer oder cycloaliphatischer Dicarbonsaeuren in feinkoerniger Form - Google Patents
Verfahren zur Herstellung von Polyamiden aliphatischer oder cycloaliphatischer Dicarbonsaeuren in feinkoerniger FormInfo
- Publication number
- DE1495375A1 DE1495375A1 DE19641495375 DE1495375A DE1495375A1 DE 1495375 A1 DE1495375 A1 DE 1495375A1 DE 19641495375 DE19641495375 DE 19641495375 DE 1495375 A DE1495375 A DE 1495375A DE 1495375 A1 DE1495375 A1 DE 1495375A1
- Authority
- DE
- Germany
- Prior art keywords
- aliphatic
- polyamides
- fine
- polyamide
- dicarboxylic acids
- 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 26
- 229920002647 polyamide Polymers 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 10
- 125000001931 aliphatic group Chemical group 0.000 title claims description 8
- 150000001991 dicarboxylic acids Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000003756 stirring Methods 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000004953 Aliphatic polyamide Substances 0.000 claims 1
- 229920003231 aliphatic polyamide Polymers 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 10
- 238000009833 condensation Methods 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 230000005494 condensation Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 aliphatic Dicarboxylic acids Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000126 substance 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- ODVYFOLTLWONHF-UHFFFAOYSA-N diphenyl decanedioate Chemical compound C=1C=CC=CC=1OC(=O)CCCCCCCCC(=O)OC1=CC=CC=C1 ODVYFOLTLWONHF-UHFFFAOYSA-N 0.000 description 2
- BDIFKMOUQSYRRD-UHFFFAOYSA-N diphenyl hexanedioate Chemical compound C=1C=CC=CC=1OC(=O)CCCCC(=O)OC1=CC=CC=C1 BDIFKMOUQSYRRD-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZGRXZVQQLDOVAT-UHFFFAOYSA-N Diasin Natural products COC(=O)C1(C)CCCC2C1CC3OC(=O)C24CC(OC(=O)C34)c5cocc5 ZGRXZVQQLDOVAT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DQUOEPYPFCBQPA-UHFFFAOYSA-N bis(4-methylphenyl) decanedioate Chemical compound C1=CC(C)=CC=C1OC(=O)CCCCCCCCC(=O)OC1=CC=C(C)C=C1 DQUOEPYPFCBQPA-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- RBSWFNKEWQOEJF-UHFFFAOYSA-N diphenyl cyclohexane-1,4-dicarboxylate Chemical compound C1CC(C(=O)OC=2C=CC=CC=2)CCC1C(=O)OC1=CC=CC=C1 RBSWFNKEWQOEJF-UHFFFAOYSA-N 0.000 description 1
- ULOZDEVJRTYKFE-UHFFFAOYSA-N diphenyl oxalate Chemical compound C=1C=CC=CC=1OC(=O)C(=O)OC1=CC=CC=C1 ULOZDEVJRTYKFE-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
-
- 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
- C08G69/28—Preparatory processes
- C08G69/30—Solid state polycondensation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/14—Powdering or granulating by precipitation from solutions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0033572 | 1964-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1495375A1 true DE1495375A1 (de) | 1969-03-27 |
Family
ID=7020892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641495375 Pending DE1495375A1 (de) | 1964-08-05 | 1964-08-05 | Verfahren zur Herstellung von Polyamiden aliphatischer oder cycloaliphatischer Dicarbonsaeuren in feinkoerniger Form |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3459714A (enExample) |
| AT (1) | AT247608B (enExample) |
| BE (1) | BE667876A (enExample) |
| CH (1) | CH439738A (enExample) |
| DE (1) | DE1495375A1 (enExample) |
| ES (1) | ES310760A1 (enExample) |
| FI (1) | FI42756C (enExample) |
| FR (1) | FR1442049A (enExample) |
| GB (1) | GB1100375A (enExample) |
| NL (1) | NL6505371A (enExample) |
| NO (1) | NO117612B (enExample) |
| SE (1) | SE309496B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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) |
| US4407983A (en) * | 1982-03-29 | 1983-10-04 | Union Carbide Corporation | Polyoxamate polymer/polyols |
| US4567249A (en) * | 1983-11-18 | 1986-01-28 | General Electric Company | Melt preparation of polyamide by amide ester interchange |
| US4739035A (en) * | 1986-08-27 | 1988-04-19 | The Standard Oil Company | Two-step process for the manufacture of polyamide from diamine and dinitrile |
| NL1009846C2 (nl) * | 1998-08-12 | 2000-02-15 | Dsm Nv | Polyamide voortbrengsel uit polytetramethyleendizuuramide. |
| ES2628778T3 (es) | 2009-04-10 | 2017-08-03 | Sk Chemicals, Co., Ltd. | Procedimiento de preparación de una poliamida resistente al calor |
| EP2617755A4 (en) * | 2010-09-17 | 2014-04-09 | Ube Industries | POLYOXAMIDE RESIN WITH EXCELLENT WEARNESS AND STRIKE PART |
| FR3030537B1 (fr) * | 2014-12-22 | 2018-08-17 | Arkema France | Fabrication de poudres de polyamide par aminolyse d'ester |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1495336A1 (de) * | 1963-12-17 | 1969-02-27 | Witten Gmbh Chem Werke | Verfahren zur Herstellung von Polyamiden der Iso- und Terephthalsaeure in feinkoerniger Form |
-
1964
- 1964-08-05 DE DE19641495375 patent/DE1495375A1/de active Pending
-
1965
- 1965-03-01 AT AT175965A patent/AT247608B/de active
- 1965-03-12 CH CH350965A patent/CH439738A/de unknown
- 1965-03-20 ES ES0310760A patent/ES310760A1/es not_active Expired
- 1965-04-02 NO NO157520A patent/NO117612B/no unknown
- 1965-04-27 NL NL6505371A patent/NL6505371A/xx unknown
- 1965-05-06 GB GB19180/65A patent/GB1100375A/en not_active Expired
- 1965-05-19 SE SE6562/65A patent/SE309496B/xx unknown
- 1965-06-03 FI FI651330A patent/FI42756C/fi active
- 1965-07-09 US US470873A patent/US3459714A/en not_active Expired - Lifetime
- 1965-08-02 FR FR26901A patent/FR1442049A/fr not_active Expired
- 1965-08-04 BE BE667876D patent/BE667876A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI42756C (fi) | 1970-10-12 |
| SE309496B (enExample) | 1969-03-24 |
| BE667876A (enExample) | 1965-12-01 |
| NO117612B (enExample) | 1969-09-01 |
| FI42756B (enExample) | 1970-06-30 |
| ES310760A1 (es) | 1965-06-01 |
| AT247608B (de) | 1966-06-27 |
| US3459714A (en) | 1969-08-05 |
| NL6505371A (enExample) | 1966-02-07 |
| GB1100375A (en) | 1968-01-24 |
| FR1442049A (fr) | 1966-06-10 |
| CH439738A (de) | 1967-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |