CS268168B2 - Process for preparing block copolymere of polyamide-6 - Google Patents
Process for preparing block copolymere of polyamide-6 Download PDFInfo
- Publication number
- CS268168B2 CS268168B2 CS859338A CS933885A CS268168B2 CS 268168 B2 CS268168 B2 CS 268168B2 CS 859338 A CS859338 A CS 859338A CS 933885 A CS933885 A CS 933885A CS 268168 B2 CS268168 B2 CS 268168B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- caprolactam
- catalyst
- initiator
- solution
- examples
- Prior art date
Links
- 229920002292 Nylon 6 Polymers 0.000 title claims abstract description 15
- 229920001577 copolymer Polymers 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 100
- 239000003999 initiator Substances 0.000 claims abstract description 32
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 30
- -1 lactam magnesium halide Chemical class 0.000 claims abstract description 25
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229920001400 block copolymer Polymers 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000004952 Polyamide Substances 0.000 claims description 11
- 229920002647 polyamide Polymers 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- YIFCDKDXYUCWAZ-UHFFFAOYSA-L magnesium;azepan-2-one;dibromide Chemical compound [Mg+2].[Br-].[Br-].O=C1CCCCCN1 YIFCDKDXYUCWAZ-UHFFFAOYSA-L 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 238000001746 injection moulding Methods 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims 3
- 238000007711 solidification Methods 0.000 claims 2
- 230000008023 solidification Effects 0.000 claims 2
- 230000003068 static effect Effects 0.000 claims 2
- 239000004809 Teflon Substances 0.000 claims 1
- 229920006362 Teflon® Polymers 0.000 claims 1
- 230000001133 acceleration Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims 1
- 230000035515 penetration Effects 0.000 claims 1
- 230000000704 physical effect Effects 0.000 claims 1
- 230000009257 reactivity Effects 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000012693 lactam polymerization Methods 0.000 abstract description 20
- 239000003505 polymerization initiator Substances 0.000 abstract description 20
- 239000000376 reactant Substances 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 229910052749 magnesium Inorganic materials 0.000 abstract description 3
- 239000011777 magnesium Substances 0.000 abstract description 3
- 230000000379 polymerizing effect Effects 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 150000003951 lactams Chemical group 0.000 description 12
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002685 polymerization catalyst Substances 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000011952 anionic catalyst Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- DVPHDWQFZRBFND-DMHDVGBCSA-N 1-o-[2-[(3ar,5r,6s,6ar)-2,2-dimethyl-6-prop-2-enoyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[4-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chlorophenyl)-4-oxoazetidin-3-yl]oxy-4-oxobutanoyl]oxyethyl] 4-o-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chloropheny Chemical group C1([C@H]2[C@H](C(N2SC(C)CC)=O)OC(=O)CCC(=O)OC(COC(=O)CCC(=O)O[C@@H]2[C@@H](N(C2=O)SC(C)CC)C=2C(=CC=CC=2)Cl)[C@@H]2[C@@H]([C@H]3OC(C)(C)O[C@H]3O2)OC(=O)C=C)=CC=CC=C1Cl DVPHDWQFZRBFND-DMHDVGBCSA-N 0.000 description 1
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229920006147 copolyamide elastomer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- YVIVRJLWYJGJTJ-UHFFFAOYSA-N gamma-Valerolactam Chemical compound CC1CCC(=O)N1 YVIVRJLWYJGJTJ-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000003381 stabilizer Substances 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
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
-
- 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
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 |
|---|---|---|---|
| US06/682,719 US4596865A (en) | 1984-12-17 | 1984-12-17 | Promotion of ε-caprolactam block copolymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS933885A2 CS933885A2 (en) | 1989-03-14 |
| CS268168B2 true CS268168B2 (en) | 1990-03-14 |
Family
ID=24740845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS859338A CS268168B2 (en) | 1984-12-17 | 1985-12-16 | Process for preparing block copolymere of polyamide-6 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4596865A (ja) |
| EP (1) | EP0186646A3 (ja) |
| JP (1) | JPH0649755B2 (ja) |
| KR (1) | KR900004793B1 (ja) |
| AU (1) | AU571761B2 (ja) |
| BR (1) | BR8506313A (ja) |
| CA (1) | CA1255038A (ja) |
| CS (1) | CS268168B2 (ja) |
| DD (1) | DD240212A5 (ja) |
| DK (1) | DK581985A (ja) |
| PT (1) | PT81688B (ja) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8400006A (nl) * | 1984-01-03 | 1985-08-01 | Stamicarbon | Werkwijze voor de condensatie van imide en alkohol. |
| US4595746A (en) * | 1984-12-17 | 1986-06-17 | Monsanto Company | Promotion of ε-caprolactam polymerization with lactam magnesium halide catalyst and 2-oxo-1-pyrrolidinyl groups |
| JP3347545B2 (ja) * | 1995-09-13 | 2002-11-20 | 三菱化学株式会社 | ランダム共重合ポリアミド樹脂及びその製造法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4223112A (en) * | 1975-03-03 | 1980-09-16 | Monsanto Company | Lactam-polyol-polyacyl lactam terpolymers |
| EP0067694B1 (en) * | 1981-06-16 | 1986-10-15 | Dsm Rim Nylon V.O.F | Acid halide and acyllactam functional materials and process for the preparation of nylon block polymers therewith |
| JPS5821425A (ja) * | 1981-06-16 | 1983-02-08 | モンサント・カンパニ− | ナイロンブロツク重合体の製法 |
| JPS5821423A (ja) * | 1981-06-16 | 1983-02-08 | モンサント・カンパニ− | 酸ハライドおよびアシルラクタム官能性物質 |
| ZA824217B (en) * | 1981-06-16 | 1983-04-27 | Monsanto Co | Acid halide and acyllactam functional materials and the process for the preparation of nylon block polymers therewith |
| EP0159704B1 (en) * | 1981-06-16 | 1989-01-18 | Dsm Rim Nylon V.O.F | Process for the preparation of molded nylon block polymers |
| US4507465A (en) * | 1982-12-29 | 1985-03-26 | Toray Industries, Inc. | Process for producing lactam/polyol block copolymer |
| JPS6028145A (ja) * | 1983-07-25 | 1985-02-13 | Hitachi Ltd | 回転陽極ｘ線管 |
| ZA849640B (en) * | 1983-12-12 | 1985-07-31 | Monsanto Co | Process for preparing nylon block copolymers and composition for use in the same |
| US4587305A (en) * | 1983-12-12 | 1986-05-06 | Monsanto Company | Composition for use in preparing nylon block copolymer |
| US4595746A (en) * | 1984-12-17 | 1986-06-17 | Monsanto Company | Promotion of ε-caprolactam polymerization with lactam magnesium halide catalyst and 2-oxo-1-pyrrolidinyl groups |
| US4595747A (en) * | 1984-12-17 | 1986-06-17 | Monsanto Company | Viscosified lactam polymerization initiator solutions |
-
1984
- 1984-12-17 US US06/682,719 patent/US4596865A/en not_active Expired - Fee Related
-
1985
- 1985-12-16 PT PT81688A patent/PT81688B/pt not_active IP Right Cessation
- 1985-12-16 DD DD85284390A patent/DD240212A5/de unknown
- 1985-12-16 CS CS859338A patent/CS268168B2/cs unknown
- 1985-12-16 JP JP60281244A patent/JPH0649755B2/ja not_active Expired - Lifetime
- 1985-12-16 KR KR1019850009449A patent/KR900004793B1/ko not_active Expired
- 1985-12-16 EP EP85870183A patent/EP0186646A3/en not_active Withdrawn
- 1985-12-16 AU AU51271/85A patent/AU571761B2/en not_active Ceased
- 1985-12-16 CA CA000497762A patent/CA1255038A/en not_active Expired
- 1985-12-16 BR BR8506313A patent/BR8506313A/pt unknown
- 1985-12-16 DK DK581985A patent/DK581985A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US4596865A (en) | 1986-06-24 |
| PT81688B (pt) | 1987-11-30 |
| AU571761B2 (en) | 1988-04-21 |
| EP0186646A2 (en) | 1986-07-02 |
| JPS61143429A (ja) | 1986-07-01 |
| EP0186646A3 (en) | 1988-07-20 |
| CS933885A2 (en) | 1989-03-14 |
| BR8506313A (pt) | 1986-08-26 |
| KR860004945A (ko) | 1986-07-16 |
| DK581985A (da) | 1986-06-18 |
| AU5127185A (en) | 1986-06-26 |
| DD240212A5 (de) | 1986-10-22 |
| JPH0649755B2 (ja) | 1994-06-29 |
| KR900004793B1 (ko) | 1990-07-05 |
| CA1255038A (en) | 1989-05-30 |
| DK581985D0 (da) | 1985-12-16 |
| PT81688A (en) | 1986-01-01 |
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