CA1064644A - Polylauric lactam, method of making higher polylactams and their application - Google Patents
Polylauric lactam, method of making higher polylactams and their applicationInfo
- Publication number
- CA1064644A CA1064644A CA227,337A CA227337A CA1064644A CA 1064644 A CA1064644 A CA 1064644A CA 227337 A CA227337 A CA 227337A CA 1064644 A CA1064644 A CA 1064644A
- Authority
- CA
- Canada
- Prior art keywords
- approx
- lactam
- melt
- catalyst
- measured according
- 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.)
- Expired
Links
- 150000003951 lactams Chemical class 0.000 title claims abstract description 97
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 30
- 239000012190 activator Substances 0.000 claims abstract description 28
- 239000000155 melt Substances 0.000 claims description 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 16
- 238000005266 casting Methods 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- 239000001569 carbon dioxide Substances 0.000 claims description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 8
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 6
- 238000005299 abrasion Methods 0.000 claims description 3
- 238000005452 bending Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 description 32
- 229920002647 polyamide Polymers 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000007792 addition Methods 0.000 description 13
- 230000035882 stress Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 239000003570 air Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000007711 solidification Methods 0.000 description 7
- 230000008023 solidification Effects 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920000299 Nylon 12 Polymers 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229920000571 Nylon 11 Polymers 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 241001417495 Serranidae Species 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N linear paraffin C13 Natural products CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VXRDAMSNTXUHFX-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;n,n-dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide Chemical compound OC(=O)C(O)C(O)C(O)=O.N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1.N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 VXRDAMSNTXUHFX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940094070 ambien Drugs 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000005058 metal casting Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical class CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- -1 phenyl isocyanate Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
- C08G69/18—Anionic polymerisation
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 |
|---|---|---|---|
| CH692374 | 1974-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064644A true CA1064644A (en) | 1979-10-16 |
Family
ID=4317171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA227,337A Expired CA1064644A (en) | 1974-05-21 | 1975-05-20 | Polylauric lactam, method of making higher polylactams and their application |
Country Status (17)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4233433A (en) | 1977-06-29 | 1980-11-11 | Harwe Ag | Process for producing molded articles from polylauryllactam activated anionic polymerization |
| US4393193A (en) | 1977-06-29 | 1983-07-12 | Harwe Ag | Process for producing molded articles from polylactams by activated anionic polymerization of medium lactams |
| DE3007204C2 (de) | 1980-02-26 | 1983-12-22 | Benkler ASD AG, Villmergen | Elektrisch isolierte Schienenstoßverbindung |
| JPS56137007U (enrdf_load_stackoverflow) * | 1980-03-17 | 1981-10-17 | ||
| JPS5847201A (ja) * | 1981-09-14 | 1983-03-18 | Mitsutoyo Mfg Co Ltd | ハイトゲ−ジ |
| US4404360A (en) | 1981-11-02 | 1983-09-13 | Harwe Ag | Homogeneous molded article produced from polylactam by activated anionic polymerization of medium lactams |
| DE3238799C1 (de) * | 1982-10-20 | 1984-02-09 | Harwe AG, 5012 Schönenwerd | Verfahren zur Herstellung von Formkoerpern aus Polylaurinlactam,sowie die danach erhaltenen Formkoerper |
| JPS62189604U (enrdf_load_stackoverflow) * | 1987-05-06 | 1987-12-02 | ||
| JPS6427605U (enrdf_load_stackoverflow) * | 1987-08-08 | 1989-02-17 | ||
| EP2447301A1 (de) * | 2010-10-29 | 2012-05-02 | Rhein Chemie Rheinau GmbH | Verfahren zur Herstellung von Gusspolyamiden |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL106789C (enrdf_load_stackoverflow) * | 1956-08-18 | |||
| NL124646C (enrdf_load_stackoverflow) * | 1959-07-14 | |||
| AT218744B (de) * | 1959-07-14 | 1961-12-27 | Basf Ag | Verfahren zur alkalischen Polymerisation von Lactamen |
| NL120559C (enrdf_load_stackoverflow) * | 1962-07-02 | |||
| BE634391A (enrdf_load_stackoverflow) * | 1962-07-03 | |||
| CH427272A (de) * | 1963-06-14 | 1966-12-31 | Inventa Ag | Verfahren zur Polymerisation von w-Laurinlactam |
| US3345340A (en) * | 1964-10-01 | 1967-10-03 | Du Pont | Polymerizing lactam to polylactam with a substituted phosphorane cocatalyst |
| DE1595638A1 (de) * | 1966-06-07 | 1970-04-30 | Bayer Ag | Verfahren zur Herstellung von Hohlkoerpern aus Polyamiden |
| GB1194350A (en) * | 1966-12-28 | 1970-06-10 | Toray Industries | Process for the Polymerisation of Lactams to Polyamides |
| CH479654A (de) | 1968-03-02 | 1969-10-15 | Basf Ag | Verfahren und Vorrichtung zum Herstellen von Polyamidformkörpern |
| DE1902507A1 (de) * | 1969-01-18 | 1970-10-15 | Degussa | Verfahren zur Herstellung von Polyamiden |
| DE2108759C3 (de) * | 1971-02-24 | 1985-11-14 | Handtmann, H. Arthur, 7950 Biberach | Verfahren zur kontinuierlichen Herstellung von Formkörpern durch die aktivierte anionische Polymerisation von Laurinlactam |
| DE2111545A1 (de) * | 1971-03-10 | 1972-09-14 | Arthur Handtmann | Giessfaehige Formmasse auf der Basis von Laurin-Lactam |
| FR2137175B1 (enrdf_load_stackoverflow) * | 1971-05-14 | 1974-03-08 | Aquitaine Total Organico | |
| JPS509026B1 (enrdf_load_stackoverflow) * | 1971-06-30 | 1975-04-09 | ||
| CS154991B1 (enrdf_load_stackoverflow) * | 1972-01-14 | 1974-04-30 |
-
1975
- 1975-02-21 DE DE19752507549 patent/DE2507549A1/de not_active Withdrawn
- 1975-02-21 DE DE19752559749 patent/DE2559749A1/de active Pending
- 1975-05-16 IT IT68268/75A patent/IT1044504B/it active
- 1975-05-19 GB GB21309/75A patent/GB1515902A/en not_active Expired
- 1975-05-19 ZA ZA00753197A patent/ZA753197B/xx unknown
- 1975-05-20 CA CA227,337A patent/CA1064644A/en not_active Expired
- 1975-05-20 DK DK220775A patent/DK220775A/da not_active Application Discontinuation
- 1975-05-20 FR FR7515642A patent/FR2272127B1/fr not_active Expired
- 1975-05-20 SE SE7505736A patent/SE425790B/xx unknown
- 1975-05-20 BR BR4000/75D patent/BR7503134A/pt unknown
- 1975-05-20 JP JP50059331A patent/JPS5139797A/ja active Granted
- 1975-05-21 NL NL7505994.A patent/NL164070C/xx not_active IP Right Cessation
- 1975-05-21 EG EG301/75A patent/EG12874A/xx active
- 1975-05-21 DD DD186150A patent/DD120210A5/xx unknown
- 1975-05-21 ES ES437847A patent/ES437847A1/es not_active Expired
- 1975-05-21 AT AT387575A patent/AT342306B/de not_active IP Right Cessation
- 1975-05-21 SU SU752140015A patent/SU688133A3/ru active
-
1978
- 1978-05-08 YU YU1097/78A patent/YU39508B/xx unknown
-
1982
- 1982-08-09 YU YU01732/82A patent/YU173282A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8128175A (en) | 1976-12-02 |
| JPS5520486B2 (enrdf_load_stackoverflow) | 1980-06-03 |
| JPS5139797A (en) | 1976-04-02 |
| DE2559749A1 (de) | 1977-09-15 |
| ES437847A1 (es) | 1977-04-16 |
| YU173282A (en) | 1985-04-30 |
| ZA753197B (en) | 1976-07-28 |
| SE425790B (sv) | 1982-11-08 |
| DD120210A5 (enrdf_load_stackoverflow) | 1976-06-05 |
| FR2272127A1 (enrdf_load_stackoverflow) | 1975-12-19 |
| NL164070C (nl) | 1980-11-17 |
| DE2507549A1 (de) | 1975-12-04 |
| SE7505736L (sv) | 1975-11-24 |
| BR7503134A (pt) | 1976-04-27 |
| AT342306B (de) | 1978-03-28 |
| YU109778A (en) | 1982-10-31 |
| IT1044504B (it) | 1980-03-31 |
| ATA387575A (de) | 1977-07-15 |
| NL164070B (nl) | 1980-06-16 |
| SU688133A3 (ru) | 1979-09-25 |
| DK220775A (da) | 1975-11-22 |
| FR2272127B1 (enrdf_load_stackoverflow) | 1980-09-26 |
| NL7505994A (nl) | 1975-11-25 |
| EG12874A (en) | 1980-07-31 |
| GB1515902A (en) | 1978-06-28 |
| YU39508B (en) | 1984-12-31 |
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