CS270425B2 - Method of polyamide-6 preparation - Google Patents

Method of polyamide-6 preparation Download PDF

Info

Publication number: CS270425B2
Authority: CS; Czechoslovakia
Prior art keywords: lactam; polymerization; caprolactam; initiator; pyrrolidone
Prior art date: 1984-12-17

Application number

CS859340A

Other languages

Czech (cs)

English (en)

Other versions

CS934085A2 (en

Inventor

James D Gabbert

Ross M Hedrick

Original Assignee

Dsm Rim Nylon Vof

Priority date (The priority date 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 date listed.)

1984-12-17

Filing date

1985-12-16

Publication date

1990-06-13

1985-12-16 Application filed by Dsm Rim Nylon Vof filed Critical Dsm Rim Nylon Vof

1989-11-14 Publication of CS934085A2 publication Critical patent/CS934085A2/cs

1990-06-13 Publication of CS270425B2 publication Critical patent/CS270425B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 17
229920002292 Nylon 6 Polymers 0.000 title claims abstract description 8
238000002360 preparation method Methods 0.000 title claims description 7
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 94
238000006116 polymerization reaction Methods 0.000 claims abstract description 37
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 30
239000003999 initiator Substances 0.000 claims abstract description 24
239000003505 polymerization initiator Substances 0.000 claims abstract description 24
-1 lactam magnesium halide Chemical class 0.000 claims abstract description 21
239000000376 reactant Substances 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 8
150000003951 lactams Chemical class 0.000 claims description 18
239000002685 polymerization catalyst Substances 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 9
150000004820 halides Chemical class 0.000 claims description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 4
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
238000012693 lactam polymerization Methods 0.000 abstract description 24
229910052749 magnesium Inorganic materials 0.000 abstract description 7
239000011777 magnesium Substances 0.000 abstract description 7
229920000642 polymer Polymers 0.000 abstract description 7
230000000379 polymerizing effect Effects 0.000 abstract 2
239000003054 catalyst Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 18
239000000243 solution Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
239000004952 Polyamide Substances 0.000 description 7
229920002647 polyamide Polymers 0.000 description 7
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 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000002243 precursor Substances 0.000 description 4
QISSLHPKTCLLDL-UHFFFAOYSA-N N-Acetylcaprolactam Chemical compound CC(=O)N1CCCCCC1=O QISSLHPKTCLLDL-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000011952 anionic catalyst Substances 0.000 description 2
YIFCDKDXYUCWAZ-UHFFFAOYSA-L magnesium;azepan-2-one;dibromide Chemical compound [Mg+2].[Br-].[Br-].O=C1CCCCCN1 YIFCDKDXYUCWAZ-UHFFFAOYSA-L 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000178 monomer Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
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
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
101100126625 Caenorhabditis elegans itr-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
229920001400 block copolymer Polymers 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
ARPUHYJMCVWYCZ-UHFFFAOYSA-N ciprofloxacin hydrochloride hydrate Chemical compound O.Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ARPUHYJMCVWYCZ-UHFFFAOYSA-N 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
230000007423 decrease Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000000945 filler 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
238000010438 heat treatment Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229920001778 nylon Polymers 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
239000002985 plastic film Substances 0.000 description 1
229920006255 plastic film Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
150000004040 pyrrolidinones Chemical class 0.000 description 1
239000012763 reinforcing filler Substances 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000005292 vacuum distillation Methods 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
- 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)
Polyesters Or Polycarbonates (AREA)
Closures For Containers (AREA)
Polymerisation Methods In General (AREA)
Cosmetics (AREA)
Processes Of Treating Macromolecular Substances (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Audible-Bandwidth Dynamoelectric Transducers Other Than Pickups (AREA)
Other In-Based Heterocyclic Compounds (AREA)

CS859340A 1984-12-17 1985-12-16 Method of polyamide-6 preparation CS270425B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/682,717 US4595746A (en)	1984-12-17	1984-12-17	Promotion of ε-caprolactam polymerization with lactam magnesium halide catalyst and 2-oxo-1-pyrrolidinyl groups

Publications (2)

Publication Number	Publication Date
CS934085A2 CS934085A2 (en)	1989-11-14
CS270425B2 true CS270425B2 (en)	1990-06-13

Family

ID=24740836

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS859340A CS270425B2 (en)	1984-12-17	1985-12-16	Method of polyamide-6 preparation

Country Status (14)

Country	Link
US (1)	US4595746A (de)
EP (1)	EP0188184B1 (de)
JP (1)	JPH0649756B2 (de)
KR (1)	KR900004791B1 (de)
AT (1)	ATE65520T1 (de)
AU (1)	AU571763B2 (de)
BR (1)	BR8506296A (de)
CA (1)	CA1255039A (de)
CS (1)	CS270425B2 (de)
DD (1)	DD240211A5 (de)
DE (1)	DE3583604D1 (de)
DK (1)	DK581785A (de)
IE (1)	IE58570B1 (de)
PT (1)	PT81686B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
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.
US4596865A (en) *	1984-12-17	1986-06-24	Monsanto Company	Promotion of ε-caprolactam block copolymerization
NL8600698A (nl) *	1986-03-19	1987-10-16	Stamicarbon	Alkalimetaallactamaat.
FR2619385B1 (fr) *	1987-08-11	1992-01-17	Atochem	Poudre de polyamide constituee de particules a structure " rose des sables ". procede d'obtention de la poudre de polyamide
NL1014605C2 (nl) *	2000-03-10	2001-09-11	Dsm Nv	Werkwijze voor het bereiden van een vertakt polymeer.
NL1014604C2 (nl) *	2000-03-10	2001-09-11	Dsm Nv	Werkwijze voor ketenverlenging.
DE10341811B4 (de) *	2003-09-10	2006-09-28	Ems-Chemie Ag	Katalysatorlösung zur Durchführung der anionischen Lactampolymerisation, Verfahren zu deren Herstellung und Polyamidformmasse
KR20090012343A (ko)	2006-05-31	2009-02-03	이 아이 듀폰 디 네모아 앤드 캄파니	폴리아미드 블록 공중합체의 제법
KR101349063B1 (ko) *	2012-02-24	2014-01-16	지에스칼텍스 주식회사	고수율로 고분자량의 폴리아미드를 제조하는 방법

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3017391A (en) *	1956-12-13	1962-01-16	Monsanto Chemicals	Preparation of polycaprolactam using n-acyl activators
DE1163541B (de) *	1961-02-24	1964-02-20	Hoechst Ag	Verfahren zur Herstellung linearer Polyamide hoher Viskositaet aus am Stickstoff unsubstituierten ª-Lactamen
US3562221A (en) *	1967-01-19	1971-02-09	Basf Ag	Accelerating anionic polymerization of lactams
US3585171A (en) *	1967-07-05	1971-06-15	Basf Ag	Accelerating the anionic polymerization of lactams
US3644264A (en) *	1969-08-01	1972-02-22	Du Pont	N-alkyl pyrrolidone-plasticized copolylactam compositions
US3862262A (en) *	1973-12-10	1975-01-21	Monsanto Co	Lactam-polyol-acyl polyactam terpolymers
US4223112A (en) *	1975-03-03	1980-09-16	Monsanto Company	Lactam-polyol-polyacyl lactam terpolymers
CH602827A5 (de) *	1975-12-10	1978-08-15	Vysoka Skola Chem Tech
JPS59124930A (ja) *	1982-12-29	1984-07-19	Toray Ind Inc	変性ポリアミドの製造法
US4507465A (en) *	1982-12-29	1985-03-26	Toray Industries, Inc.	Process for producing lactam/polyol block copolymer
JPS59197428A (ja) *	1983-04-26	1984-11-09	Toray Ind Inc	変性ポリアミドの製造法
CA1214012A (en) *	1983-01-27	1986-11-18	Wei-Yeih W. Yang	Rim process using single component composition
CA1225179A (en) *	1983-12-12	1987-08-04	James D. Gabbert	Cross-linked nylon block copolymers
US4596865A (en) *	1984-12-17	1986-06-24	Monsanto Company	Promotion of ε-caprolactam block copolymerization
US4595747A (en) *	1984-12-17	1986-06-17	Monsanto Company	Viscosified lactam polymerization initiator solutions

1984
- 1984-12-17 US US06/682,717 patent/US4595746A/en not_active Expired - Lifetime
1985
- 1985-12-16 DE DE8585870185T patent/DE3583604D1/de not_active Expired - Fee Related
- 1985-12-16 AT AT85870185T patent/ATE65520T1/de not_active IP Right Cessation
- 1985-12-16 IE IE317185A patent/IE58570B1/en not_active IP Right Cessation
- 1985-12-16 EP EP85870185A patent/EP0188184B1/de not_active Expired - Lifetime
- 1985-12-16 CA CA000497760A patent/CA1255039A/en not_active Expired
- 1985-12-16 KR KR1019850009445A patent/KR900004791B1/ko not_active Expired
- 1985-12-16 BR BR8506296A patent/BR8506296A/pt unknown
- 1985-12-16 DD DD85284389A patent/DD240211A5/de unknown
- 1985-12-16 DK DK581785A patent/DK581785A/da not_active Application Discontinuation
- 1985-12-16 PT PT81686A patent/PT81686B/pt not_active IP Right Cessation
- 1985-12-16 CS CS859340A patent/CS270425B2/cs not_active IP Right Cessation
- 1985-12-16 JP JP60281245A patent/JPH0649756B2/ja not_active Expired - Lifetime
- 1985-12-16 AU AU51269/85A patent/AU571763B2/en not_active Ceased

Also Published As

Publication number	Publication date
US4595746A (en)	1986-06-17
PT81686B (pt)	1987-10-20
DE3583604D1 (en)	1991-08-29
EP0188184A2 (de)	1986-07-23
KR860004943A (ko)	1986-07-16
IE58570B1 (en)	1993-10-06
JPH0649756B2 (ja)	1994-06-29
EP0188184A3 (en)	1988-03-02
EP0188184B1 (de)	1991-07-24
CS934085A2 (en)	1989-11-14
CA1255039A (en)	1989-05-30
DK581785A (da)	1986-06-18
PT81686A (en)	1986-01-01
AU5126985A (en)	1986-06-26
JPS61143430A (ja)	1986-07-01
BR8506296A (pt)	1986-08-26
DK581785D0 (da)	1985-12-16
IE853171L (en)	1986-06-17
DD240211A5 (de)	1986-10-22
KR900004791B1 (ko)	1990-07-05
AU571763B2 (en)	1988-04-21
ATE65520T1 (de)	1991-08-15

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2001-02-14	MK4A	Patent expired	Effective date: 20001216

Publication	Publication Date	Title
KR970000487B1 (ko)	1997-01-13	신규 폴리아미드류 및 이로부터 수득되는 물품
US6060580A (en)	2000-05-09	Star-shaped branched polyamide
JP3417938B2 (ja)	2003-06-16	ラクタムのアニオン重合方法
JPH10292041A (ja)	1998-11-04	アニオンラクタム重合用液状触媒系の製造法
US5864007A (en)	1999-01-26	Liquid system for executing an anionic lactam polymerization
CS270425B2 (en)	1990-06-13	Method of polyamide-6 preparation
KR100513025B1 (ko)	2005-12-29	음이온성락탐을중합하기위한액체다분성시스템
US5200498A (en)	1993-04-06	Lactam-lactone copolymer
KR102287645B1 (ko)	2021-08-06	실리카계 촉매를 이용한 배위-음이온 개환 중합에 의한 폴리아마이드의 제조방법 및 이에 의해 제조된 폴리아마이드
KR100672190B1 (ko)	2007-01-19	폴리아미드의 제조방법
US4596865A (en)	1986-06-24	Promotion of ε-caprolactam block copolymerization
KR900004794B1 (ko)	1990-07-05	ε-카프로락탐 중합반응에 적합한 조성물
KR880002239B1 (ko)	1988-10-20	N-치환된 아실-락탐 화합물을 제조하는 방법
CA1252089A (en)	1989-04-04	Process for preparing an acyl-lactam compound
US4644050A (en)	1987-02-17	Poly(1-oxy-3-lactam vinylene)
US3228916A (en)	1966-01-11	Anionic polymerization of e-caprolactam with cyanogen halide as activator
US3394112A (en)	1968-07-23	Anionic polymerization of anhydrous lactams with amido acetals as co-catalysts
CA1252090A (en)	1989-04-04	N- substituted acyl-lactam compound
US4171425A (en)	1979-10-16	Nitrobenzene-accelerated lactam polymerization
RU2110531C1 (ru)	1998-05-10	Способ получения ударопрочного блоксополиэфирамида
US3945984A (en)	1976-03-23	Preparing polyamides by anionic polymerization of lactams
US3715340A (en)	1973-02-06	Process for preparing polyamides
SU732292A1 (ru)	1980-05-05	Способ получени полиамидов
JPH0689132B2 (ja)	1994-11-09	ポリアミド成形品の製法