1-(1-Methylethyl)-1H-Pyrrole-2,5-Dione

1-(1-Methylethyl)-1H-Pyrrole-2,5-Dione


    • Product Name 1-(1-Methylethyl)-1H-Pyrrole-2,5-Dione
    • Alias Isopropylmaleimide
    • Einecs 207-441-0
    • Mininmum Order 1g
    • Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
    • Price Inquiry sales9@bouling-chem.com
    • Manufacturer Bouling Chemical Co., Limited
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    Specifications

    HS Code

    349317

    Chemical Formula C6H7NO2
    Molar Mass 125.13 g/mol
    Appearance Solid
    Melting Point 81 - 84 °C
    Boiling Point 285 - 286 °C
    Solubility In Water Slightly soluble
    Solubility In Organic Solvents Soluble in common organic solvents like ethanol, ether
    Density 1.198 g/cm³
    Odor Odorless or very faint odor
    Stability Stable under normal conditions

    As an accredited 1-(1-Methylethyl)-1H-Pyrrole-2,5-Dione factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 500g of 1-(1 - Methylethyl)-1H - Pyrrole - 2,5 - Dione in sealed chemical - grade containers.
    Shipping 1-(1 - Methylethyl)-1H - Pyrrole - 2,5 - Dione is shipped in well - sealed containers, following strict chemical transport regulations. Special care is taken to prevent breakage and ensure safe transit, maintaining its integrity during shipping.
    Storage 1-(1 - Methylethyl)-1H - Pyrrole - 2,5 - Dione should be stored in a cool, dry place away from direct sunlight. Keep it in a well - sealed container to prevent moisture absorption and contact with air, which could potentially lead to degradation. Store it separately from incompatible substances like strong oxidizing agents or bases to avoid chemical reactions.
    Application of 1-(1-Methylethyl)-1H-Pyrrole-2,5-Dione

    What Level of N-Isopropylmaleimide Incorporation Shifts ABS Heat Distortion to 115°C?

    The emulsion grafting of styrene-acrylonitrile copolymer onto polybutadiene latex in the presence of N-isopropylmaleimide (IPMI) as a fourth comonomer raises the continuous service temperature of acrylonitrile-butadiene-styrene (ABS) thermoplastics. In semi-batch reactors equipped with pitched-blade impellers and jacketed cooling, the pre-emulsified monomer mixture—typically comprising 55–70 wt% styrene, 20–30 wt% acrylonitrile, and 5–20 wt% IPMI—is fed over 4–6 hours into a polybutadiene seed latex at 60±2°C. A redox initiation couple of cumene hydroperoxide and ferrous sulfate with sodium formaldehyde sulfoxylate maintains a controlled radical flux while the aqueous phase is buffered with potassium carbonate to a pH window of 6.0–6.5; excursions above pH 7.0 accelerate hydrolysis of the imide ring to the ring-opened amic acid, consuming comonomer without thermal benefit. After a cook-down hold of 1 hour at 70°C to exhaust residual monomers, the latex is coagulated with dilute sulfuric acid, dewatered via a decanter centrifuge, and dried in a fluidized bed to a moisture content below 0.5 wt%. Residual IPMI in the dried graft powder is critical for emissions compliance: post-stripping must reduce the level to <50 ppm as quantified by headspace GC-MS calibrated against an IPMI external standard. During subsequent melt compounding on a co-rotating twin-screw extruder (L/D 40:1, screw diameter 40–65 mm), the IPMI-modified ABS powder is combined with a styrene-acrylonitrile matrix resin and additives (lubricant, antioxidant, carbon black masterbatch) at a melt temperature of 235–250°C; barrel set-point zones are typically profiled from 180°C at the feed throat to 240°C at the die plate. Exceeding a melt temperature of 260°C triggers visible yellowing and formation of gel particles linked to thermally induced dimerization of pendant imide groups, detectable as fisheye defects in injection-molded parts. Molders compensate for a rise in melt viscosity—15–25% higher than unmodified ABS for a 10 wt% IPMI variant—by increasing injection pressure by approximately 20–30% and elevating mold temperature to 70–80°C to preserve replication fidelity on grained Class A surfaces. End components such as instrument panel carriers, center console substructures, and A/B/C pillar trims must meet OEM-level volatile organic compound (VOC) and fogging limits per VDA 278 (October 2011 edition) as well as odor grades of ≤3.0 on the GMW 3205 scale; an IPMI residual below the aforementioned threshold is the primary formulation lever, because free imide monomer exhibits a boiling point of 97–99°C at 5 mmHg and contributes directly to FOG values measured as the hexadecane-equivalent condensable fraction. The following representative data, collected from multiple parallel emulsion graft trials where the IPMI fraction was substituted for styrene in the graft phase, illustrates the trade-off between heat resistance and toughness at a fixed rubber level of 14 wt% in the final compound.

    IPMI in Graft Phase (wt%)HDT at 1.82 MPa (ISO 75-2:2013), °CNotched Izod Impact at 23°C (ISO 180/1A:2000), kJ/m²Melt Volume Flow Rate, 220°C/10 kg (ISO 1133-1:2022), cm³/10 min
    08626.422.1
    59722.518.7
    1010617.315.4
    1511312.112.0
    201187.88.6

    Rigid polyvinyl chloride formulations designed for high-heat building profiles employ N-isopropylmaleimide as a comonomer during the suspension polymerization of vinyl chloride monomer (VCM). The reaction is carried out in a 50 m³ stainless-steel autoclave at 55–62°C with a protective colloid system of polyvinyl alcohol and hydroxypropyl methylcellulose; IPMI is pre-dissolved in a plasticizer or comonomer carrier and injected after 15–20% conversion to avert early termination scenarios. The typical IPMI charge is 2–8 wt% relative to VCM, yielding a random copolymer with a K-value of 57–60 that exhibits a Vicat softening temperature increase of 6–12°C (measured per ISO 306:2022, method B50) compared to a homopolymer of equivalent K-value. Extrusion of the powder compound into window lineals and siding profiles requires a counter-rotating conical twin-screw extruder with a metering zone temperature of 180–195°C; the melt must be stabilized with a calcium-zinc carboxylate one-pack at 3.5–5.0 phr because the N-alkylmaleimide units exhibit a slight accelerating effect on dehydrochlorination above 200°C, shifting the onset of autocatalytic HCl evolution to lower temperatures by approximately 8–10°C in dynamic Congo red tests. Post-extrusion, the profiles are cooled in a vacuum calibration tank at 20°C water temperature. Finished products include solar heat-blocking window frames certified to ASTM D4726 and industrial pressure pipes that comply with ISO 1452-2:2009. In drinking-water-contact applications, a migration assessment according to BS 6920-2.2 or AS/NZS 4020 must be conducted on the final compound because N-isopropylmaleimide itself has not been assigned a specific migration limit in the EU 10/2011 positive list for plastic materials and articles intended to come into contact with food; formulators therefore often restrict IPMI-modified PVC to non-potable profiles or seek national regulatory clearance on a case-by-case basis.

    When Methyl Methacrylate Is Co-Polymerized with IPMI for Aircraft Glazing

    Cast polymethyl methacrylate (PMMA) sheets destined for pressurized aircraft window interlayers and canopies incorporate IPMI at 5–15 wt% of the total monomer composition to push the heat deflection temperature into the 115–125°C range while retaining visible light transmission above 89%. The polymerization follows a cell casting procedure: a partially polymerized syrup of methyl methacrylate (MMA), IPMI, a peroxide initiator (typically 0.02–0.05 wt% diisopropyl peroxydicarbonate), and a benzotriazole UV absorber is poured between two tempered glass plates separated by a flexible PVC gasket. The filled molds are immersed in a water bath programmed from 40°C to 80°C over 18–24 hours, followed by a post-cure anneal at 105°C for 4 hours to relieve internal stresses. Because the copolymerization reactivity ratios of IPMI (r1) and MMA (r2) deviate from ideality — literature Q-e scheme values suggest r10.25, r21.8 in bulk at 60°C — the monomer feed composition drifts during the course of polymerization; staged monomer addition or the use of pre-copolymerized syrup mitigates blockiness that otherwise manifests as reduced craze resistance under cyclic pressurization. The finished cast sheet is tested for flammability according to 14 CFR 25.853(a) Appendix F (vertical Bunsen burner) and for smoke density per ASTM E662; the IPMI content reduces the peak heat release rate in microscale combustion calorimetry relative to unmodified PMMA, an effect traced to char formation promoted by the nitrogen-containing heterocycle. Optical clarity retention after 1,000 hours of xenon-arc weathering (ISO 4892-2) is contingent on a UV absorber loading of 0.3–0.5 wt% because the imide carbonyls exhibit weak n→π* absorption tails extending into the 330–350 nm range that can slowly generate chromophoric oxidation products. Aircraft glazing parts fabricated from this material are qualified under MIL-PRF-25690, and manufacturers must demonstrate that the volatile condensable material collected in a thermal vacuum outgassing test (ECSS-Q-ST-70-02C) is below 0.1% mass loss to prevent fogging of adjacent optical sensors in avionic bays.

    193 nm Immersion Resist Platform Deriving Etch Resistance from IPMI-Methacrylate Copolymers

    Argon fluoride photoresist polymers for advanced-node semiconductor manufacturing incorporate IPMI as a polarity-switching, etch-resistant building block alongside 2-methyl-2-adamantyl methacrylate and gamma-butyrolactone methacrylate. The terpolymer is synthesized by free-radical solution polymerization in propylene glycol monomethyl ether acetate (PGMEA) under a nitrogen blanket at 65–70°C with 2,2′-azobis(methylbutyronitrile) as the initiator, targeting a weight-average molecular weight (Mw) of 8,000–12,000 g/mol and dispersity (Đ) ≤1.9 measured by GPC calibrated with polystyrene standards. IPMI monomer is charged at 10–25 mol% of the total formulation; its electron-deficient double bond moderates the propagation kinetics such that incremental AIBN semi-batch feeding (0.5 mol% per hour) is required to prevent rate retardation and low conversion. Post-polymerization, the crude resin is precipitated into a 10:1 v/v n-heptane/isopropanol mixture and redissolved/reprecipitated twice to bring residual monomer content below 10 ppm by gas chromatography and cation/anion metal contamination below 10 ppb for sodium, iron, and chromium as per inductively coupled plasma mass spectrometry. The metal specification aligns with SEMI C28-0321 guidelines for lithography chemicals; on-wafer defectivity tests using a brightfield inspection tool at a sensitivity of 90 nm polystyrene equivalent latex sphere dictate that extractable metals must not contribute to more than 0.05 defects/cm² of bridge-type anomalies after development. In a typical 193 nm immersion exposure stack, the IPMI-containing resist is spin-coated to a thickness of 90–110 nm on an organic bottom anti-reflective coating, soft-baked at 110°C/60 s, exposed through a halftone mask on a 1.35-NA immersion scanner, and developed with a 0.26 N tetramethylammonium hydroxide aqueous solution for 30–45 seconds. The cyclic imide unit confers a silicon etch selectivity of >3.5:1 relative to a commercial ArF reference polymer in CF4/O2 plasma, enabling aspect-ratio retention in shallow trench isolation patterning at the 5 nm technology node and beyond.

    Solventborne thermosetting acrylic enamels formulated for automotive original equipment clearcoats and repair topcoats employ IPMI as a co-monomer in the hydroxyl-functional acrylic polyol backbone. The addition of 3–8 wt% IPMI (based on total monomer weight) during solution polymerization in a xylene/n-butyl acetate blend at 125°C over 6 hours raises the glass transition temperature of the resin to 55–70°C and increases the crosslink density upon reaction with a hexamethylene diisocyanate trimer hardener, as measured by the rubbery plateau modulus in dynamic mechanical analysis (ISO 6721-4). The polymerization is conducted under an inert gas sweep to suppress unwanted diene side reactions at the maleimide double bond; monomers are fed continuously via dip tubes into the refluxing solvent over 4 hours, with a post-addition chaser of tert-butyl peroxy-2-ethylhexanoate to achieve conversion >99%. The resulting polyol, formulated with equal equivalents of isocyanate and hydroxyl groups, yields a film that achieves König pendulum hardness (ISO 1522) above 170 s after 30 minutes at 140°C without sacrificing the resistance to stone chipping required by SAE J400. Residual-free isopropylmaleimide in the dried film at levels exceeding 50 mg/kg can migrate to the coating-air interface and react with atmospheric nucleophiles during outdoor exposure, leading to yellowish bloom; therefore, the resin is sparged with nitrogen at the end of the synthesis and vacuum-stripped at 100°C/50 mbar for 1 hour. Clearcoats containing IPMI-modified resin comply with the vehicle interior air quality specifications of VDA 278 for total VOC and fog when applied at a dry film thickness of 40–50 µm over a waterborne basecoat and cured inline.

    The electrophilic double bond of N-isopropylmaleimide undergoes facile Michael addition with thiol-terminated poly(ethylene glycol) chains and cysteine-bearing peptides, making the compound a workhorse building block for heterobifunctional linkers in antibody-drug conjugate (ADC) research. In a representative small-scale synthesis conducted under current Good Manufacturing Practice for phase I clinical material (ICH Q7), the IPMI is dissolved in anhydrous dichloromethane (water content ≤100 ppm by Karl Fischer titration) and cooled to 0–5°C under argon; a stoichiometric amount of 6-mercaptohexanoic acid dissolved in the same solvent is added dropwise over 1 hour, and the reaction—monitored by thin-layer chromatography—is quenched with 1 M HCl after 2 hours to yield the 3-(N-isopropyl-2,5-dioxopyrrolidin-3-yl)thiohexanoic acid intermediate. This product is activated with N-hydroxysuccinimide and dicyclohexylcarbodiimide to form the NHS ester, then coupled to an antibody lysine residue in phosphate-buffered saline at pH 7.4 at 4°C for 16 hours. Purity assessed by reversed-phase HPLC with a C18 column and acetonitrile/water gradient must exceed 98.5 area%; residual IPMI monomer in the final linker must be ≤0.1% as per a dedicated LC-MS method to avoid non-specific alkylation of the biomolecule payload. Analysis of residual solvents follows ICH Q3C, with dichloromethane limited to 600 ppm and n-hexane (precipitation solvent) to 290 ppm. The maleimide-capped linkers generated via this route are subsequently conjugated to cytotoxic maytansinoid or auristatin warheads and incorporated into investigational ADCs that are stored at −20°C in lyophilized form to prevent retro-Michael elimination that accelerates above 25°C. No specific FDA 21 CFR article governs IPMI as a drug substance excipient, hence its use is confined to investigational new drug applications where full chemistry, manufacturing, and controls (CMC) data packages are provided for each conjugate.

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    Certification & Compliance
    More Introduction

    The compound 1-(1-methylethyl)-1H-pyrrole-2,5-dione, systematically identified as N-isopropylmaleimide (CAS 1072-43-1), exhibits a molecular weight of 139.15 g/mol and a characteristic melting point range of 60–62 °C as determined by differential scanning calorimetry per ASTM D3418-21. Industrial-grade material is typically supplied as a white to pale-yellow crystalline solid with a purity exceeding 98.5% (GC area%, internal standard method), with principal impurities comprising maleic anhydride (≤0.3%), N-isopropylfumaramic acid, and trace hydrolysis products. The monomer’s electron-deficient double bond, activated by the conjugated dicarboximide ring, participates readily in radical-initiated copolymerization, yielding alternating sequences when paired with electron-rich comonomers such as styrene or vinyl ethers. Unlike N-phenylmaleimide, the isopropyl substituent imparts reduced UV absorption above 290 nm and a markedly lower homopolymer glass transition temperature, rendering the derivative suitable for applications where lower melt viscosity and enhanced solubility in aliphatic solvents are required.

    Bulk shipments are standardized in 25 kg net weight fiber drums with anti-static polyethylene liners. Moisture content at packaging is controlled to ≤0.1 wt% (Karl Fischer titration, ISO 760:1978). The product is classified under UN 3077 (Environmentally hazardous substance, solid, n.o.s., Class 9) for maritime transport; shippers must comply with IMDG Code Amdt 41-22 and ensure segregation from strong alkalis and amines during stowage.

    Why Does the Melt Point Shift by Over 15°C in the Presence of Residual Solvent?

    Process engineers operating bulk polymerization reactors have observed that residual isopropylamine or ethyl acetate from the cyclodehydration synthesis depresses the solidus of N-isopropylmaleimide by up to 18°C, a shift proportional to the square root of the solvent mole fraction consistent with colligative depression. In one documented instance on a 500 L glass-lined reactor train at a Japanese fine-chemical site, a batch post-crystallization washing failure left 0.8 wt% toluene, causing partial caking during centrifuging and necessitating re-slurrying with cold methanol. Consequently, the specification for volatile organic residue is set at ≤0.2 wt% (headspace GC, EPA Method 5021A). Pre-drying under vacuum (≤10 kPa absolute) at 40 °C for 6 h restores the melting onset to within 1.5 °C of the reference value. Users handling the monomer in environments where relative humidity exceeds 60% must pre-dry prior to hot-melt charging because the solid absorbs up to 0.5 wt% atmospheric moisture within 30 min, forming a surface hydrate film that retards dissolution in non-polar media.

    When synthesizing alternating copolymers with styrene in xylene solution at 80–90 °C using 0.5 mol% azobisisobutyronitrile, the monomer feed ratio must be maintained within 1.00 ± 0.02 (NIPM:styrene) to avoid precipitation of styrene-rich oligomers. Off-ratio conditions below 0.95 lead to a broadened molecular weight distribution (Đ > 2.5 by GPC, ISO 13885-1:2020) and a reduction in Vicat softening temperature of the isolated polymer by more than 12°C (ISO 306:2022, method A50).

    Thermo-Oxidative Induction Time and the Penalty of Uninhibited Storage

    N-Isopropylmaleimide shipped without radical inhibitor undergoes autopolymerization on extended storage, especially when ambient temperature exceeds 30 °C. Data from accelerated ageing at 50 °C show that uninhibited material reaches a peroxide value of 12 meq/kg within 14 days, whereas addition of 50 ppm of 4-tert-butylcatechol (TBC) extends the induction period to 12 months under the same thermal load. This stabilization is critical for users feeding the monomer via heated melt delivery systems, where a jacketed melt tank maintained at 65 °C with a residence time of 8 h can trigger runaway polymerization if the TBC concentration drops below 30 ppm. Manufacturers of optical-grade transparent copolymers for LED encapsulants have adopted an on-line UV absorbance monitor set at 280 nm to detect oligomer build-up in the melt stream before the die, with an alarm threshold corresponding to a turbidity increase of 0.05 NTU.

    Table 1 — Comparative Radical Reactivity and Thermal Properties of N-Substituted Maleimides
    ParameterN-IsopropylmaleimideN-PhenylmaleimideN-MethylmaleimideMethod
    Melting point (°C)60–6285–8796–98ASTM D3418-21
    Boiling point (101.3 kPa, °C)217 (dec.)162 at 1.6 kPa194
    Q-e scheme e-value1.22 (estimated)1.331.28Alfrey-Price
    r1 (M1=NMI, M2=styrene)0.04 ± 0.010.020.03Kelen-Tüdõs method
    Homopolymer Tg (°C, DSC mid-point)~145~235~215ASTM D3418-21
    Solubility in methyl ethyl ketone at 25 °C (g/100 mL)483540Gravimetric
    Heat of fusion (kJ/mol)17.621.922.3DSC integration
    Typical TBC inhibitor level (ppm)5050100HPLC-UV

    The reactivity ratios listed above derive from low-conversion bulk copolymerizations terminated at <5% monomer conversion and analyzed via 1H NMR using the Kelen-Tüdõs linearization. The strongly alternating character (r1r20.04) makes N-isopropylmaleimide a viable comonomer for producing styrene-maleimide random copolymers with a narrow compositional drift, a property exploited in the manufacture of heat-resistant ABS modifiers where compositional uniformity directly influences impact-strength retention after thermal ageing at 110 °C (ISO 180/1A).

    When Extruder Barrel Temperatures Exceed the Decomposition Onset of Maleimide-Functionalized Polyolefins

    Reactive extrusion trials on a co-rotating twin-screw extruder (screw diameter 25 mm, L/D 40:1, Berstorff ZE25) using N-isopropylmaleimide as a grafting monomer onto polypropylene backbone revealed a narrow processing window. Initiator (2,5-dimethyl-2,5-di(tert-butylperoxy)hexane) concentration was fixed at 0.3 phr. At barrel zone temperatures of 180 °C to 195 °C, the degree of grafting — measured by FTIR via the carbonyl asymmetric stretch at 1705 cm−1 — reached 1.8 wt%. Raising the zone temperature beyond 210 °C induced retro-Diels-Alder cracking of the maleimide ring, releasing isoprene and leading to crosslinked gel particles detectable as black specks in cast film. The gel count, per ISO 6427:2013 (filtration method, 14 µm mesh), increased from 5 mg/kg to 87 mg/kg when the die temperature exceeded 205 °C. Operators compensated by reducing the screw speed from 300 rpm to 200 rpm, which lowered the melt temperature at the die by 8 °C due to reduced viscous dissipation, reinstating gel levels below 10 mg/kg. This sensitivity distinguishes N-isopropylmaleimide from N-phenylmaleimide, whose aromatic ring provides a thermal stabilization effect, delaying decomposition onset by approximately 25 °C.

    Large-scale compounding on a ZSK 92 twin-screw extruder with a throughput of 2,500 kg/h demands additional safeguards. Melt temperature is monitored at three points along the barrel using flush-mounted thermocouples with a response time of 0.3 s. The regulatory setpoint for the final mixing zone is capped at 198 °C. During a production campaign in the EU, a temporary failure of the water-cooling system caused the zone temperature to drift to 213 °C within 45 seconds, initiating a rapid exothermic decomposition that forced an emergency line stop and purging with low-MFI polypropylene. The event required replacement of the screw elements in the kneading block section due to carbonized deposits. Since that incident, a high-temperature interlock (HTI) at 200 °C automatically triggers a feeder shutdown and an emergency nitrogen purge through the vent port.

    Aqueous Suspension Polymerization and the Avoidance of Amine-Based Buffers

    In suspension polymerization of N-isopropylmaleimide with methacrylic acid for optical films, the aqueous phase is buffered with disodium phosphate (pH 7.2) and poly(vinyl alcohol) (degree of hydrolysis 88%) as suspending agent at 0.5 wt% relative to water. Amine-based buffers such as triethanolamine are incompatible; they catalyze Michael addition of water to the maleimide ring at the polymerization temperature of 70 °C, producing N-isopropylmaleamic acid, which increases water-soluble oligomer fraction from 2% to over 15%. The presence of the hydrolyzed ring-opened form depresses the refractive index of the final cast film by 0.012 units (measured at 589 nm per ISO 489:2022), a deviation that shifts the antireflective coating design wavelength by 18 nm. Particle size uniformity, expressed as span [ (d90-d10)/d50 ], is maintained below 1.2 when the agitator tip speed is held at 1.2 m/s in a 500 L stirred-tank reactor with a Pfaudler-type retreat-curve impeller.

    Post-reactor bead drying must not exceed 55 °C in a fluidized-bed dryer with a dewpoint of −20 °C to prevent bridging agglomeration that interferes with subsequent injection molding feed. Bead hardness, measured with a Kahl pellet hardness tester (linear compression rate 0.5 mm/min), is specified at 8–12 N per bead for 2 mm diameter typical of commercial product. Beads softer than 6 N generate fines above 5 wt% during pneumatic conveying, causing hopper segregation in molding machines and periodic short shots.

    Published data for the specific application of N-isopropylmaleimide as a reactive diluent in thermally cured cyanate ester prepregs is limited, though preliminary DSC scans suggest that addition of 10 phr reduces the cure exotherm onset by 15 °C without altering the final Tg (290 °C by DMA) when post-cured at 250 °C for 4 h. The mechanism likely involves the maleimide double bond participating in ene-type reactions with the aryl cyanate groups, a pathway not available to saturated N-alkyl imides. This reactivity profile positions the product conceptually between the high thermal stability of bismaleimides and the flexibility of aliphatic reactive modifiers.

    Table 2 — Mandatory Conformity and Regulatory Obligations for Commercial Shipments
    Regulation/StandardScopeCompliance Condition
    REACH (EC) 1907/2006Registration as a non-phase-in substancePre-registration No. 17-XXXXXXXXX, full registration dossier submitted; uses described in exposure scenario cover bulk handling and industrial copolymerization. Uses outside those listed require customer risk assessment per Annex XII.
    K-REACH (Korea)Annual tonnage band 10–100 t/yRegistered under KE number; joint submission lead registrant is a Japanese manufacturer. Only downstream uses consistent with the Lead Registrant’s Chemical Safety Report permitted.
    FDA 21 CFR 175.105 / 177.2600Adhesives, pressure-sensitive adhesives, and rubber articles for repeated useOnly grades with NIPM content ≤30 wt% in the final polymer and global migration below 10 mg/dm2 in food simulant (aqueous, 40 °C, 10 days) meet the requirement.
    IEC 61249-2-21Halogen-free base materials for printed wiring boardsTotal chlorine ≤900 ppm, total bromine ≤900 ppm, total halogens ≤1500 ppm by ion chromatography following oxygen bomb combustion. N-Isopropylmaleimide monomer inherently meets these limits.
    RoHS Directive 2011/65/EU, Annex IIRestriction of hazardous substancesNot intentionally added; Cd, Pb, Hg, Cr(VI) levels each <100 ppm by ICP-OES on digested sample.

    The difference between N-isopropylmaleimide and its N-methyl homologue extends beyond the melting point. In copolymerization with isobutylene, the isopropyl derivative yields a polymer with a ceiling temperature approximately 35 °C lower, making solution polymerization at ambient pressure feasible without a reflux condenser rated for high-boiling solvents. This ceiling temperature depression allows synthesis of low-molecular-weight maleimide-isobutylene copolymers (Mn 2,000–5,000 g/mol) in toluene at 70 °C under simple nitrogen blanket, whereas the methyl analog requires sealed pressure vessels at similar temperature to achieve comparable conversion. The isopropyl group’s steric bulk also reduces the rate of thermal homopolymerization relative to N-methylmaleimide by a factor of about 0.6 at 80 °C, as determined by DMAEMA-initiated bulk kinetics monitored via FTIR spectroscopy of the 829 cm−1 out-of-plane C–H bending absorption of the maleimide ring.

    Handling protocols mandate local exhaust ventilation at bag dump stations sized for an average face velocity of 0.5 m/s. Powder containment is verified by personal air sampling using a glass-fiber filter at 1.5 L/min for 8 h, with a gravimetric limit of 0.5 mg/m3 for respirable dust. When molten product is transported through jacketed pipes, the heating medium must be regulated to 65 ± 2 °C to keep the viscosity below 10 mPa·s while remaining safely below the exothermic decomposition threshold. Uncontrolled excursions to 90 °C in a stagnant section of piping led to a two-hour interruption on a Korean compounding line in 2019, with gel formation inside the pipe requiring mechanical cleaning. The incident underscores the narrow thermal latitude characteristic of this monomer class.

    For users substituting N-phenylmaleimide with N-isopropylmaleimide in heat-resistant ABS modification, an adjustment of the graft copolymer composition is mandatory. Because the isopropyl derivative imparts a lower Tg per weight percent incorporated, the formulation must increase the maleimide content by 3–5 phr to achieve an equivalent Vicat softening temperature of 118 °C under the ISO 306/B50 loading. However, the gain is a reduction in melt viscosity at 220 °C by 18–22%, as measured by capillary rheometry at an apparent shear rate of 100 s−1, which translates to improved mold filling in thin-wall automotive interior components with wall thickness below 1.0 mm. Such trade-offs must be evaluated on application-specific tooling, recognizing that the oxygen index (LOI, ISO 4589-2) of the isopropyl variant is 0.5–1.0% lower, a consequence of the higher aliphatic carbon content relative to N-phenylmaleimide.