Synthesis and characterization of AB-type monomers and polyimides: a review

Thiruvasagam, P.

doi:10.1080/15685551.2013.771307

Cited by 31 publications

(20 citation statements)

References 74 publications

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“…charge transfer complexes, CTC) and chain motions (7,8) with aliphatic groups generally disrupting the molecular packing (9). As in many other material classes, the traditional approach to increase the service life of polyimides has been by increasing their thermal and mechanical stability (10)(11)(12). However, a small amount of work has already been done on turning polyimides into self-healing grades.…”

Section: Introductionmentioning

confidence: 99%

Effect of the Dianhydride/Branched Diamine Ratio on the Architecture and Room Temperature Healing Behavior of Polyetherimides

Susa

Bose

Grande

et al. 2016

ACS Appl. Mater. Interfaces

101

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Traditional polyetherimides (PEIs) are commonly synthesized from an aromatic diamine and an aromatic dianhydride (e.g. 3,4'-oxydianiline (ODA) and 4,4'-oxydiphtalic anhydride (ODPA)) leading to the imide linkage and outstanding chemical, thermal and mechanical properties yet lacking any self-healing functionality. In this work, we have replaced the traditional aromatic diamine by a branched aliphatic fatty dimer diamine (DD1).This led to a whole family of self-healing polymers not containing reversible chemical bonds, capable of healing at (near) room temperature yet maintaining very high elastomeric-like mechanical properties (up to 6 MPa stress and 570% strain at break). In this work, we present the effect of the DD1/ODPA ratio on the general performance and healing behavior of a room temperature healing polyetherimide. A dedicated analysis suggests that healing proceeds in three steps: (i) an initial adhesive step leading to the formation of a relatively weak interface; (ii) a second step at long healing times leading to the formation of an interphase with different properties than the bulk material and (iii) disappearance of the damaged zone leading to full healing. We argue that the fast interfacial adhesive step is due to van der Waals interactions of long dangling alkyl chains followed by an interphase formation due to polymer chain interdiffusion. An increase in DD1 ratio leads to an increase in the healing kinetics and displacement shift of the first healing step towards lower temperatures. An excess of DD1 leads to the crosslinking of the polymer thereby restricting the necessary mobility for the interphase formation and limiting the self-healing behavior. The results here presented offer a new route for the development of room temperature self-healing thermoplastic elastomers with improved mechanical properties using fatty dimer diamines.

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Section: Introductionmentioning

confidence: 99%

Effect of the Dianhydride/Branched Diamine Ratio on the Architecture and Room Temperature Healing Behavior of Polyetherimides

Susa

Bose

Grande

et al. 2016

ACS Appl. Mater. Interfaces

101

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“…Markoski previously reported that a high molecular weight linear polyetherimide was synthesized from self-condensation of 4-fluoro-N-3-hydroxyphenyl phthalimide, an AB-type monomer that contains a pair of tert-butyldimethylsilyl protected phenols and an activated aryl fluoride group [40,41]. Thiruvasagam recently synthesized polyetherimides by aromatic nucleophilic substitution reactions from AB-type monomers containing both phenolate salt and nitrophthalimide [42,43]. As early as in 1995, Mathias LJ attempted to synthesize poly(thioether imide)s from N-(p-mercaptophenyl)-4-chlorophthalimide (AB monomer); nevertheless, this kind of polyimide was only soluble in sulfuric acid and flexible films could not be obtained because of low molecular weight and limited flexibility of polymer backbone itself [44].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of high performance poly(thioether imide)s via aromatic nucleophilic substitution reaction of isomeric AB-type monomers

2015

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A series of isomeric poly(thioether imide)s (PTIs) containing thioether linkages were prepared by aromatic nucleophilic substitution reaction of isomeric N-(4-mercaptophenyl)-3-chlorophthalimide and/or N-(4-mercaptophenyl)-4-chlorophthalimide. The inherent viscosities of these polymers were in the range of 0.38-0.42 dL/g. The glass transition temperature increased with increasing the content of 3-substituted phthalimide unit in the polymer backbone. The 5 % weight loss temperatures of isomeric PTIs (a-e) were 506-531°C in nitrogen and 509-536°C in air, respectively. The isomeric PTIs (b-d) films exhibited good mechanical properties with tensile strength of about 90 MPa, elongation at break of more than 6.0 %, and tensile moduli of more than 2.2 GPa. The storage moduli of PTIs (b-d) almost completely maintained at about 2.0 GPa before reaching the corresponding glass transition temperatures. It is noted that the minimum melt viscosity of these polymers decreased with increasing the content of unsymmetrical 3-and 4-substituted phthalimide unit.

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“…Aromatic polyimides [1][2][3][4][5] are one of the most important classes of thermally stable/high performance polymers due to their excellent thermal, mechanical, and electrical properties. Polyimides are widely used in electrical, electronics, automotive, chemical, and aerospace industries [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and properties of novel diol monomers and processable thermally stable polyimides

Thiruvasagam

2014

Colloid Polym Sci

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Diimide-diol monomers containing aliphatic spacer N,N′-bis (2-hydroxyethyl) biphenyl tetracarboxylic diimide and N,N′-bis(2-hydroxyethyl)benzophenone tetracarboxylic diimide were synthesized by a nucleophilic substitution reaction that involved ethanolamine and commercially available aromatic dianhydrides. The structures of the monomers were characterized by FT-IR and 1 H-NMR. Processable polyimides (PIs) containing aliphatic spacer were synthesized from these new diols and 4,4′-dichlorodiphenyl sulfone/4,4′-difluorobenzophenone by nucleophilic substitution reaction. The polyimides were characterized by FT-IR, 1 H-NMR, X-ray diffraction (XRD), thermogravimetry (TG), differential scanning calorimetry (DSC), solution viscosity, and solubility test. The X-ray diffraction patterns indicated that all these polyimides were amorphous and soluble in common organic solvents. Thermogravimetry analysis indicated that the polyimides exhibit good thermal stability, and 10 % weight loss occurred in the temperature range 375 to 429°C. The limited oxygen index (LOI) values of polyimides were in the range 36.3 to 37.5 and such PIs can be used as self extinguishing polymers.

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Synthesis and characterization of AB-type monomers and polyimides: a review

Cited by 31 publications

References 74 publications

Effect of the Dianhydride/Branched Diamine Ratio on the Architecture and Room Temperature Healing Behavior of Polyetherimides

Effect of the Dianhydride/Branched Diamine Ratio on the Architecture and Room Temperature Healing Behavior of Polyetherimides

Synthesis and characterization of high performance poly(thioether imide)s via aromatic nucleophilic substitution reaction of isomeric AB-type monomers

Synthesis, characterization, and properties of novel diol monomers and processable thermally stable polyimides

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