DE2014505A1 - Anionische katalytische Polymerisation von Lactamen - Google Patents
Anionische katalytische Polymerisation von LactamenInfo
- Publication number
- DE2014505A1 DE2014505A1 DE19702014505 DE2014505A DE2014505A1 DE 2014505 A1 DE2014505 A1 DE 2014505A1 DE 19702014505 DE19702014505 DE 19702014505 DE 2014505 A DE2014505 A DE 2014505A DE 2014505 A1 DE2014505 A1 DE 2014505A1
- Authority
- DE
- Germany
- Prior art keywords
- lactam
- lactams
- polymerization
- amount
- isocyanate
- 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
- 150000003951 lactams Chemical class 0.000 title claims description 29
- 238000006116 polymerization reaction Methods 0.000 title claims description 21
- 125000000129 anionic group Chemical group 0.000 title claims description 6
- 230000003197 catalytic effect Effects 0.000 title claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
- -1 lactam lactam Chemical class 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XSJFAAMNRIJDGN-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)cyclobutane Chemical compound O=C=NCC1CCC1CN=C=O XSJFAAMNRIJDGN-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940113125 polyethylene glycol 3000 Drugs 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 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
- C08G69/20—Anionic polymerisation characterised by the catalysts used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6904544A NL6904544A (en, 2012) | 1969-03-25 | 1969-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2014505A1 true DE2014505A1 (de) | 1970-10-01 |
Family
ID=19806514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702014505 Pending DE2014505A1 (de) | 1969-03-25 | 1970-03-25 | Anionische katalytische Polymerisation von Lactamen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3704280A (en, 2012) |
| JP (1) | JPS4841958B1 (en, 2012) |
| BE (1) | BE747856A (en, 2012) |
| CH (1) | CH542258A (en, 2012) |
| DE (1) | DE2014505A1 (en, 2012) |
| FR (1) | FR2039978A5 (en, 2012) |
| GB (1) | GB1298501A (en, 2012) |
| NL (1) | NL6904544A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2248664A1 (de) * | 1972-10-04 | 1974-04-18 | Bayer Ag | Verfahren zur herstellung von polyamiden mit erhoehter schlagzaehigkeit |
| EP0129036B1 (en) * | 1983-06-13 | 1991-12-18 | AlliedSignal Inc. | Polyamide-polyol block copolymers and anionic polymerization process |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7209838A (en, 2012) * | 1972-07-15 | 1974-01-17 | ||
| US3923925A (en) * | 1972-10-04 | 1975-12-02 | Bayer Ag | Process for the preparation of polyamides with increase impact strength |
| DE2325153C2 (de) * | 1973-05-18 | 1984-06-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyamidhohlkörpern |
| JPS574962B2 (en, 2012) * | 1974-05-29 | 1982-01-28 | ||
| CS187003B1 (en) * | 1976-04-30 | 1979-01-31 | Rudolf Puffr | Process for preparing polyamides |
| DE2716004C3 (de) * | 1977-04-09 | 1987-01-22 | Hüls AG, 4370 Marl | Thermoplastische Formmassen auf der Basis von Polylaurinlactam und deren Verwendung zur Herstellung von Rohren |
| US4261881A (en) * | 1979-05-07 | 1981-04-14 | Chevron Research Company | Poly-2-pyrrolidone composition having improved stability and method of extruding |
| DE2931689A1 (de) * | 1979-08-04 | 1981-02-26 | Bayer Ag | Polyamid-formmassen mit verbesserter zaehigkeit |
| US4501821A (en) * | 1983-07-28 | 1985-02-26 | Ppg Industries, Inc. | Property enhancement of anionically polymerized nylon with dual initiators |
| NL8302928A (nl) * | 1983-08-20 | 1985-03-18 | Stamicarbon | N-gesubstitueerde carbamoyl-lactam verbinding. |
| DE3469360D1 (en) * | 1983-08-20 | 1988-03-24 | Stamicarbon | Process for the preparation of an n-substituted carbamoyllactam compound |
| NL8302929A (nl) * | 1983-08-20 | 1985-03-18 | Stamicarbon | Werkwijze voor het bereiden van een n-gesubstitueerde carbamoyl-lactam verbinding. |
| US4578447A (en) * | 1983-12-28 | 1986-03-25 | Ex-Cell-O Corporation | Rim nylon-based urethane block polymer composition |
| NL8400006A (nl) * | 1984-01-03 | 1985-08-01 | Stamicarbon | Werkwijze voor de condensatie van imide en alkohol. |
-
1969
- 1969-03-25 NL NL6904544A patent/NL6904544A/xx unknown
-
1970
- 1970-03-23 CH CH434470A patent/CH542258A/de not_active IP Right Cessation
- 1970-03-23 GB GB03836/70A patent/GB1298501A/en not_active Expired
- 1970-03-24 BE BE747856D patent/BE747856A/xx unknown
- 1970-03-24 JP JP45024792A patent/JPS4841958B1/ja active Pending
- 1970-03-25 FR FR7010753A patent/FR2039978A5/fr not_active Expired
- 1970-03-25 DE DE19702014505 patent/DE2014505A1/de active Pending
- 1970-03-25 US US22684A patent/US3704280A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2248664A1 (de) * | 1972-10-04 | 1974-04-18 | Bayer Ag | Verfahren zur herstellung von polyamiden mit erhoehter schlagzaehigkeit |
| EP0129036B1 (en) * | 1983-06-13 | 1991-12-18 | AlliedSignal Inc. | Polyamide-polyol block copolymers and anionic polymerization process |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2039978A5 (en, 2012) | 1971-01-15 |
| JPS4841958B1 (en, 2012) | 1973-12-10 |
| CH542258A (de) | 1973-09-30 |
| US3704280A (en) | 1972-11-28 |
| BE747856A (fr) | 1970-09-24 |
| NL6904544A (en, 2012) | 1970-09-29 |
| GB1298501A (en) | 1972-12-06 |
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