DE1162553B - Process for the production of polyamide moldings with a fine crystalline structure - Google Patents
Process for the production of polyamide moldings with a fine crystalline structureInfo
- Publication number
- DE1162553B DE1162553B DEB67243A DEB0067243A DE1162553B DE 1162553 B DE1162553 B DE 1162553B DE B67243 A DEB67243 A DE B67243A DE B0067243 A DEB0067243 A DE B0067243A DE 1162553 B DE1162553 B DE 1162553B
- Authority
- DE
- Germany
- Prior art keywords
- polyamides
- polyamide
- added
- crystalline structure
- production
- 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 21
- 229920002647 polyamide Polymers 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000465 moulding Methods 0.000 title claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- HCUZVMHXDRSBKX-UHFFFAOYSA-N 2-decylpropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)C(O)=O HCUZVMHXDRSBKX-UHFFFAOYSA-N 0.000 description 1
- MVDKKZZVTWHVMC-UHFFFAOYSA-N 2-hexadecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C(O)=O MVDKKZZVTWHVMC-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- -1 enanthlactam Chemical compound 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UVTQXRIBKWGKLD-UHFFFAOYSA-N n-cyclohexylcyclohexanamine;methane Chemical compound C.C1CCCCC1NC1CCCCC1 UVTQXRIBKWGKLD-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Description
Verfahren zur Herstellung von Polyamidformkörpern mit feinkristalliner Struktur Zusatz zum Patent: 1052112 Das Patent 1 052 112 betrifft ein Verfahren zur Herstellung von Polyamidformkörpern mit feinkristalliner Struktur, bei dem man Polyamide verwendet, denen vor ihrer Verformung kleine Mengen eines in ihrer Schmelze unter den üblichen Verarbeitungsbedingungen sich nicht oder nur wenig lösenden oder quellenden feinpulvrigen, höherschmelzenden Polyamids zugesetzt sind.Process for the production of polyamide moldings with finely crystalline Structure Addendum to the patent: 1052112 The patent 1 052 112 relates to a method for the production of polyamide moldings with a finely crystalline structure, in which one Polyamides used, which before their deformation, small amounts of one in their melt under the usual processing conditions not or only slightly dissolving or swelling finely powdered, higher melting polyamides are added.
Es wurde gefunden, daß man Polyamidformkörper mit feinkristalliner Struktur aus Polyamiden, denen vor ihrer Verformung kleine Mengen eines in ihrer Schmelze unter den üblichen Verarbeitungsbedingungen sich nicht oder wenig lösenden oder quellenden feinpulvrigen höherschmelzenden Polyamids zugesetzt worden sind, nach Patent 1 052 112 auch erhalten werden können, wenn man Polyamide verwendet, bei deren Herstellung den polyamidbildenden Ausgangsstoffen diese höherschmelzenden Polyamide zugesetzt worden sind. It has been found that polyamide moldings with finely crystalline Structure made of polyamides, which before their deformation, small amounts of one in their Melt does not dissolve or dissolves slightly under the usual processing conditions or swelling, finely powdered, higher-melting polyamides have been added, according to patent 1,052,112 can also be obtained using polyamides, in their production the polyamide-forming starting materials these higher-melting Polyamides have been added.
Polyamidbildende Ausgangsstoffe im Sinne der Erfindung sind: Lactame, wie Caprolactam, Önanthlactam, Capryllactam, C-Methyl-e-caprolactame od. ä., weiterhin Salze von Diaminen, wie Hexamethylendiamin, Octamethylendiamin, Dekamethylendiamin, Bis-(4-aminocyclohexyl)-methan od. ä., und Dicarbonsäuren, wie Adipinsäure, Korksäure, Sebacinsäure, Undecandicarbonsäure oder Heptadecandicarbonsäure, sowie aliphatische co-Aminoalkohole und Dicarbonsäuren oder Gemische mehrerer der genannten Stoffe. Polyamide-forming starting materials for the purposes of the invention are: lactams, such as caprolactam, enanthlactam, capryllactam, C-methyl-e-caprolactam or the like, furthermore Salts of diamines, such as hexamethylenediamine, octamethylenediamine, decamethylenediamine, Bis (4-aminocyclohexyl) methane or the like, and dicarboxylic acids, such as adipic acid, suberic acid, Sebacic acid, undecanedicarboxylic acid or heptadecanedicarboxylic acid, as well as aliphatic co-amino alcohols and dicarboxylic acids or mixtures of several of the substances mentioned.
Als erfindungsgemäß verwendbare, kristallisationsfördernde Zusätze eignen sich außer den im Hauptpatent genannten Polyamiden auch Kondensationsprodukte von Salzen aus mindestens dreiwertigen Säuren, wie Pyromellithsäure, Butantetracarbonsäure, '-Cyclohexanontetrapropionsäure oder Polyacrylsäure, und mehrwertigen Basen, wie Dicyclohexylaminmethan, Xylylendiamin, ol,or'- Cyclohexanontetrapropylamin, sowie Polymethylen-bis-caprolactam, die vernetzt oder verzweigt sein können und die sehr hoch oder gar nicht schmelzen. As additives which can be used according to the invention and which promote crystallization In addition to the polyamides mentioned in the main patent, condensation products are also suitable of salts of at least trivalent acids, such as pyromellitic acid, butanetetracarboxylic acid, '-Cyclohexanontetrapropionic acid or polyacrylic acid, and polyvalent bases such as Dicyclohexylamine methane, xylylenediamine, ol, or'-cyclohexanone tetrapropylamine, as well as Polymethylene-bis-caprolactam, which can be crosslinked or branched and which are very melt high or not at all.
Überraschenderweise behalten diese kristallisationsfördernden Zusätze ihre Wirksamkeit, wenn man sie schon den festen oder geschmolzenen polyamidbildenden Ausgangsstoffen zugibt. Obwohl bei der anschließenden Polymerisation oder Polykondensation die Berührungszeit mit der Schmelze etwa 10- bis 20mal länger ist als beim Zusatz zu den Polyamiden gemäß Patent 1 052 112, finden offenbar weder Umamidierungsreaktionen statt, noch lösen sich die Komponenten ineinander. Surprisingly, these crystallization-promoting additives retain their effectiveness, if you already have the solid or molten polyamide-forming Adding raw materials. Although in the subsequent polymerization or polycondensation the contact time with the melt is about 10 to 20 times longer than with the addition to the polyamides according to patent 1,052,112, apparently neither transamidation reactions take place instead, the components are still dissolving into one another.
Die Molekulargewichte und die Mengen der vor der Polymerisation zugesetzten Polyamide entsprechen denen des Hauptpatents. Man verwendet demnach nieder- bis hochmolekulare Produkte, zweckmäßig jedoch solche mit einem K-Wert nach F i k e n t -s c h e r von etwa 30 bis 50, in Mengen von 0,01 bis 1 Gewichtsprozent, vorzugsweise 0,05 bis 0,5 Gewichtsprozent. The molecular weights and the amounts of before Polymerization added Polyamides correspond to those of the main patent. Accordingly, one uses low to High molecular weight products, but expediently those with a K value according to F i k e n t -s c h e r from about 30 to 50, in amounts from 0.01 to 1 percent by weight, preferably 0.05 to 0.5 percent by weight.
Die in dem folgenden Beispiel genannten Teile sind Gewichtsteile. The parts mentioned in the following example are parts by weight.
Beispiel Eine aus 1000 Teilen Caprolactam, 100 Teilen Wasser und 1 Teil eines feingepulverten Polyamids aus Oxalsäure und Propylendiamin, durch Polykondensation im Autoklav in üblicher Weise hergestellte Polyamidschmelze ist gleichmäßig mit sehr feinen Sphärolithen versetzt und läßt sich im Spritzguß sehr gut in hoher Schußfolge zu Formteilen verarbeiten. Example One from 1000 parts of caprolactam, 100 parts of water and 1 part of a finely powdered polyamide made from oxalic acid and propylenediamine, through polycondensation Polyamide melt produced in the usual way in the autoclave is uniform with very fine spherulites and can be injection molded very well in high shot sequence process into molded parts.
Claims (2)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB67243A DE1162553B (en) | 1962-05-15 | 1962-05-15 | Process for the production of polyamide moldings with a fine crystalline structure |
| CH546263A CH447604A (en) | 1957-03-19 | 1963-05-01 | Process for the production of polyamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB67243A DE1162553B (en) | 1962-05-15 | 1962-05-15 | Process for the production of polyamide moldings with a fine crystalline structure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1162553B true DE1162553B (en) | 1964-02-06 |
Family
ID=6975450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB67243A Pending DE1162553B (en) | 1957-03-19 | 1962-05-15 | Process for the production of polyamide moldings with a fine crystalline structure |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1162553B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348561A (en) * | 2009-04-29 | 2016-02-24 | 巴塞尔聚烯烃股份有限公司 | Thermoplastic polymeric composition with improved resistance to thermo-oxidative degradation and use thereof for producing pipes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB569184A (en) * | 1941-04-11 | 1945-05-11 | Du Pont | Improvements in or relating to the manufacture of new polymeric materials |
| DE1052112B (en) * | 1957-03-19 | 1959-03-05 | Basf Ag | Process for the production of polyamide moldings with a fine crystalline structure |
-
1962
- 1962-05-15 DE DEB67243A patent/DE1162553B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB569184A (en) * | 1941-04-11 | 1945-05-11 | Du Pont | Improvements in or relating to the manufacture of new polymeric materials |
| DE1052112B (en) * | 1957-03-19 | 1959-03-05 | Basf Ag | Process for the production of polyamide moldings with a fine crystalline structure |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348561A (en) * | 2009-04-29 | 2016-02-24 | 巴塞尔聚烯烃股份有限公司 | Thermoplastic polymeric composition with improved resistance to thermo-oxidative degradation and use thereof for producing pipes |
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