WO2001066633A1 - Chain extension process - Google Patents
Chain extension process Download PDFInfo
- Publication number
- WO2001066633A1 WO2001066633A1 PCT/NL2001/000199 NL0100199W WO0166633A1 WO 2001066633 A1 WO2001066633 A1 WO 2001066633A1 NL 0100199 W NL0100199 W NL 0100199W WO 0166633 A1 WO0166633 A1 WO 0166633A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- melt
- polymer
- catalyst
- difunctional
- carbonylbislactamate
- Prior art date
Links
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
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/916—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G69/04—Preparatory processes
-
- 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
-
- 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
- C08G69/48—Polymers modified by chemical after-treatment
Definitions
- the invention relates to a process for preparing a high- molecular weight polymer by contacting in a melt a difunctional polymer having a lower molecular weight whose end functional groups are -OH or -NH 2 groups with a carbonylbislactamate (CBL) with the following formula
- n is an integer from 3 to 15
- WO 98/47940 describes a process for preparing a high-molecular polyamide by contacting polyamide having a lower molecular weight in the melt with carbonylbiscaprolactamate (CBC) A drawback of that process is that the reaction proceeds comparatively slowly
- the object of the invention is to provide a process that does not have the aforementioned drawback or has the aforementioned drawback to a lesser extent
- This object is achieved by the melt also containing an acid or a base
- the acid or base has the function of a catalyst
- Acids that are suitable for use as a catalyst for chain extension in the presence of CBL are LiX, Sb 2 0 3 , Ge0 2 and As 2 0 3 , BX 3 , MgX 2 , B ⁇ X 3 , SnX 4 ,
- DABCO diazobicyclo[2,2,2]octane
- DMAP dimethylaminopyhdine
- guanidine morfoline
- DBTDL dibutyl tin dilaurate
- DBTDL dibutyl
- the catalyst is a Lewis acid or a Lewis base. This ensures that the time needed for curing is even shorter.
- the Lewis acid or base prefferably be tetraalkoxytitanate, Zr(OR) 4 , Li versetate, ZnAcAc in which the alkoxy group is for example a butoxy group or an isopropoxy group.
- the amount of carbonylbiscaprolactamate used in the process of the invention may vary between wide limits. As a rule, at least about 0.1 % by weight relative to the functional polymer is needed in order to have an appreciable effect. Amounts in excess of 3% by weight do not normally result in any further increase in molecular weight.
- a difunctional polymer here and hereinafter means a polymer with two functional groups per molecule consisting of an -OH group or an -NH 2 group.
- Examples of such polymers are polyamides, polyesters, polycarbonates and polyetherpolyols.
- the process of the invention can in principle be applied for all types of polyamide.
- polyamide include at least the aliphatic polyamides, for example polyamide-4, polyamide-6, polyamide-8, polyamide-4,6, polyamide-6,6, polyam ⁇ de-6,10, polyamides derived from an aliphatic diamine and an aromatic dicarboxy c acid, for example polyam ⁇ de-4,T, polyam ⁇ de-6,T, polyam ⁇ de-4,l, where T stands for terephthalate and I for isophthalate, copoiyamides of linear polyamides and copoiyamides of an aliphatic and a partially aromatic polyamide, for example polyamide 6/6, T and 6/6,1
- Suitable polyesters for which the process of the invention may be applied are at least polyesters derived from aliphatic dicarboxyhc acids and diols, polyesters of aliphatic and cycloahphatic diols and aromatic dicarboxyhc acids, copolyesters that are partly aliphatic and partly aromatic and polyesters which contain units that are derived from cycloahphatic dicarboxyhc acids Examples hereof are polybutylene adipate, polymethylene terephthalate polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, copolyesters of polybutylene adipate and polybutylene terephthalate and the polyesters derived from butane diol and cyclohexanedicarboxyhc acid
- the polyetherpolyols, for which the process of the invention may be applied are polyols, which possess a oxyalkylene structure, composed of a oxyalkylene
- the process of the invention can readily be carried out using the customary techniques and melt blending equipment for example by blending the lower molecular polyamide and the carbonylbislactamate and optionally other additives in the solid phase, for example in a tumble dryer, whereupon the obtained blend is melted in a customary melt blender, for example a Haake kneader, a Brabender blender or a twin-screw or double-screw extruder
- a customary melt blender for example a Haake kneader, a Brabender blender or a twin-screw or double-screw extruder
- the various components may also be added to the blending equipment separately
- the carbonylbislactamate and catalyst may also be added to a polymer product stream of a functional polymer having a lower molecular weight as it exits from a polymerization reactor in which this polymer was polymerized
- the polymerization process may be operated batch-wise or continuously In the former case, the residence time in the reactor can be shortened and so productivity can be increased and the postcondensation step can be omitted
- CBL reacts solely with the -NH 2 groups or the -OH functional groups of the functional polymers.
- Functional polymers that also possess -COOH functionality react with either the -OH functional groups or the -NH 2 functional groups. If -COOH functionality is present in the melt, it is preferred not only for CBL and the catalyst but also a bisoxazine or a bisoxazoline to be present in the process of the invention. This ensures that the reaction proceeds even more rapidly.
- the bisoxazoline is 1 ,4- phenylenebisoxazoline.
- the invention will be elucidated on the bases of the following examples.
- Example 1 was repeated without adding any catalyst. The relative viscosity increased from 1.59 to 1.76
- lithium chloride zirconium(IV)butoxide, zirconium acetylacetonate or lithium versetate are added.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002402430A CA2402430A1 (en) | 2000-03-10 | 2001-03-09 | Chain extension process |
JP2001565796A JP2003525989A (en) | 2000-03-10 | 2001-03-09 | Chain extension method |
AU2001242861A AU2001242861A1 (en) | 2000-03-10 | 2001-03-09 | Chain extension process |
EP01915913A EP1263864A1 (en) | 2000-03-10 | 2001-03-09 | Chain extension process |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL1014604 | 2000-03-10 | ||
NL1014604A NL1014604C2 (en) | 2000-03-10 | 2000-03-10 | Procedure for chain extension. |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001066633A1 true WO2001066633A1 (en) | 2001-09-13 |
Family
ID=19770973
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/NL2001/000199 WO2001066633A1 (en) | 2000-03-10 | 2001-03-09 | Chain extension process |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1263864A1 (en) |
JP (1) | JP2003525989A (en) |
CN (1) | CN1416449A (en) |
AU (1) | AU2001242861A1 (en) |
CA (1) | CA2402430A1 (en) |
NL (1) | NL1014604C2 (en) |
WO (1) | WO2001066633A1 (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL1019241C2 (en) * | 2001-10-26 | 2003-05-01 | Dsm Nv | New polymer compositions, as well as the preparation and use thereof. |
WO2004046156A1 (en) * | 2002-11-20 | 2004-06-03 | Dsm Ip Assets B.V. | Silane coupling agent, process for the preparation of a silane coupling agent, use of said silane coupling agent in a composite or on a substrate, nanoparticles and use thereof in a coating. |
US6984694B2 (en) | 2002-02-01 | 2006-01-10 | Johnson Polymer, Llc | Oligomeric chain extenders for processing, post-processing and recycling of condensation polymers, synthesis, compositions and applications |
DE102007040683A1 (en) | 2007-08-29 | 2009-03-05 | Evonik Degussa Gmbh | Sheathed pipe |
DE102008044224A1 (en) | 2008-12-01 | 2010-06-02 | Evonik Degussa Gmbh | Use of a composition for contact with supercritical media |
US7745548B2 (en) | 2003-09-05 | 2010-06-29 | Ticona Gmbh | Polyoxymethylene homopolymers and copolymers, and production and use thereof |
DE102009001001A1 (en) | 2009-02-19 | 2010-09-02 | Evonik Degussa Gmbh | Use of a conduit for the production of a pipeline laid in the water |
US7795357B2 (en) | 2003-09-05 | 2010-09-14 | Ticona Gmbh | Polyoxymethylene multi-block copolymers, their production and use |
DE102011007104A1 (en) | 2011-04-11 | 2012-10-11 | Evonik Degussa Gmbh | Polyamide sheathed steel construction tubes for offshore structures |
US8927737B2 (en) | 2011-08-09 | 2015-01-06 | Basf Se | Process for purifying ionic liquids |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100465207C (en) * | 2005-08-31 | 2009-03-04 | 北京化工大学 | Process for preparing high-molecular aliphatic polyester |
CN101585915B (en) * | 2008-05-23 | 2011-04-20 | 北京化工大学 | Method for preparing biodegradable polyesteramide through chain extension |
CN102643422A (en) * | 2011-02-21 | 2012-08-22 | 北京化工大学 | Preparation method for biodegradable aliphatic alternating polyester amide |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3862262A (en) * | 1973-12-10 | 1975-01-21 | Monsanto Co | Lactam-polyol-acyl polyactam terpolymers |
EP0147792A2 (en) * | 1984-01-03 | 1985-07-10 | Stamicarbon B.V. | Process for the condensation of imide and alcohol |
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 |
JPS6399228A (en) * | 1986-06-23 | 1988-04-30 | Teijin Ltd | Production of polyester having high polymerization degree |
EP0556170A1 (en) * | 1992-01-29 | 1993-08-18 | Monsanto Company | Lactam-lactone copolymers |
WO1996034909A1 (en) * | 1995-05-04 | 1996-11-07 | Dsm N.V. | High-molecular polyamide |
WO1998047940A1 (en) * | 1997-04-22 | 1998-10-29 | Dsm N.V. | High-molecular polyamide |
-
2000
- 2000-03-10 NL NL1014604A patent/NL1014604C2/en not_active IP Right Cessation
-
2001
- 2001-03-09 EP EP01915913A patent/EP1263864A1/en not_active Withdrawn
- 2001-03-09 CN CN 01806375 patent/CN1416449A/en active Pending
- 2001-03-09 WO PCT/NL2001/000199 patent/WO2001066633A1/en not_active Application Discontinuation
- 2001-03-09 JP JP2001565796A patent/JP2003525989A/en active Pending
- 2001-03-09 CA CA002402430A patent/CA2402430A1/en not_active Abandoned
- 2001-03-09 AU AU2001242861A patent/AU2001242861A1/en not_active Abandoned
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3862262A (en) * | 1973-12-10 | 1975-01-21 | Monsanto Co | Lactam-polyol-acyl polyactam terpolymers |
EP0147792A2 (en) * | 1984-01-03 | 1985-07-10 | Stamicarbon B.V. | Process for the condensation of imide and alcohol |
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 |
JPS6399228A (en) * | 1986-06-23 | 1988-04-30 | Teijin Ltd | Production of polyester having high polymerization degree |
EP0556170A1 (en) * | 1992-01-29 | 1993-08-18 | Monsanto Company | Lactam-lactone copolymers |
WO1996034909A1 (en) * | 1995-05-04 | 1996-11-07 | Dsm N.V. | High-molecular polyamide |
WO1998047940A1 (en) * | 1997-04-22 | 1998-10-29 | Dsm N.V. | High-molecular polyamide |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Section Ch Week 198823, Derwent World Patents Index; Class A23, AN 1988-158448, XP002157844 * |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL1019241C2 (en) * | 2001-10-26 | 2003-05-01 | Dsm Nv | New polymer compositions, as well as the preparation and use thereof. |
WO2003035767A1 (en) * | 2001-10-26 | 2003-05-01 | Dsm Ip Assets B.V. | New polymer compositions, the preparation and use thereof as well as shaped parts and the preparation thereof |
US6984694B2 (en) | 2002-02-01 | 2006-01-10 | Johnson Polymer, Llc | Oligomeric chain extenders for processing, post-processing and recycling of condensation polymers, synthesis, compositions and applications |
WO2004046156A1 (en) * | 2002-11-20 | 2004-06-03 | Dsm Ip Assets B.V. | Silane coupling agent, process for the preparation of a silane coupling agent, use of said silane coupling agent in a composite or on a substrate, nanoparticles and use thereof in a coating. |
US7795357B2 (en) | 2003-09-05 | 2010-09-14 | Ticona Gmbh | Polyoxymethylene multi-block copolymers, their production and use |
US7745548B2 (en) | 2003-09-05 | 2010-06-29 | Ticona Gmbh | Polyoxymethylene homopolymers and copolymers, and production and use thereof |
DE102007040683A1 (en) | 2007-08-29 | 2009-03-05 | Evonik Degussa Gmbh | Sheathed pipe |
DE102008044224A1 (en) | 2008-12-01 | 2010-06-02 | Evonik Degussa Gmbh | Use of a composition for contact with supercritical media |
WO2010063506A1 (en) | 2008-12-01 | 2010-06-10 | Evonik Degussa Gmbh | Use of a composition for the contact with supercritical media |
DE102009001001A1 (en) | 2009-02-19 | 2010-09-02 | Evonik Degussa Gmbh | Use of a conduit for the production of a pipeline laid in the water |
DE102011007104A1 (en) | 2011-04-11 | 2012-10-11 | Evonik Degussa Gmbh | Polyamide sheathed steel construction tubes for offshore structures |
EP2511430A1 (en) | 2011-04-11 | 2012-10-17 | Evonik Degussa GmbH | Steel tubes for offshore structures |
US8927737B2 (en) | 2011-08-09 | 2015-01-06 | Basf Se | Process for purifying ionic liquids |
Also Published As
Publication number | Publication date |
---|---|
CA2402430A1 (en) | 2001-09-13 |
AU2001242861A1 (en) | 2001-09-17 |
NL1014604C2 (en) | 2001-09-11 |
CN1416449A (en) | 2003-05-07 |
JP2003525989A (en) | 2003-09-02 |
EP1263864A1 (en) | 2002-12-11 |
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