Mechanical Properties and Characterization of a Catechol-Polymer Biocomposite for 3D Printable Dental Applications

Hassen Merzouk¹, Samir Habibi², Benali Boutabout³, Noureddine Gherraf*⁴

¹University of Mustapha Stambouli, Faculty of Sciences and Technology,

Department of Mechanic, Mascara 29000, Algeria, https://orcid.org/0009-0000-6989-2316.

²University of Sidi BEL Abbes, Faculty of Sciences and Technology,

Department of Mechanic, BP 89 Sidi Bel Abbes 22000, Algeria. https://orcid.org/0000-0003-4307-2592.

³University of Sidi BEL Abbes , Faculty of Sciences and Technology,

Department of Mechanic BP 89 Sidi Bel Abbes 22000, Algeria, https://orcid.org/0000-0003-2305-8988.

⁴Laboratory of Natural Resources and Management of Sensitive Environments,

Oum el-Bouaghi University, Algeria, https://orcid.org/0000-0002-9635-2275.

*Corresponding Author E-mail: Hassen.merzouk@univ-mascara.dz, habibismr@yahoo.com, bboutabout@yahoo.fr, ngherraf@yahoo.com

ABSTRACT:

In recent years, polymers containing catechol groups—originally inspired by the adhesive proteins found in mussels—have drawn growing attention from researchers and biomaterial developers, especially for use in dentistry. These materials exhibit excellent surface adhesion due to the unique properties of catechol groups and their ability to form hydrogen bonds, making them valuable across various applications. Dopamine and its naturally occurring derivative, 3,4-dihydroxyphenylalanine (DOPA), were selected as the foundation for creating a polymerizable monomer. This was achieved through a chemical reaction with methacrylic anhydride to produce dopamine methacrylamide (DMA). The newly synthesized compound was then thoroughly analyzed using FT-IR, 1H-NMR, and 13C-NMR spectroscopy to confirm its structure. Following this, DMA was combined with ethoxylated di-GMA (EBPDMA) in different ratios to develop formulations suitable for DLP 3D printing. To create catechol-functionalized polymers, free radical polymerization was carried out in DMF using dopamine methacrylamide and methyl methacrylate (MMA). The resulting cross-linked polymer networks were analyzed using gel permeation chromatography (GPC), along with FT-IR and 1H-NMR techniques, to better understand their structural characteristics. Finally, the mechanical performance of the developed materials was assessed through a series of tests, including measurements of compressive strength, flexural strength, and hardness, all conducted using a universal testing machine (UTM).

KEYWORDS: Dental Composite, Polymer, Catechol, Dopamine, 3D printing.

INTRODUCTION:

The growing demand for highly aesthetic dental restorations has sparked significant research into tooth-colored materials used in both removable and fixed prostheses. Patients and clinicians alike are seeking natural-looking solutions that blend seamlessly with surrounding teeth, driving innovation in material science. However, the success of these new materials isn't judged solely by how well they perform in the mouth over time—durability, color stability, and biocompatibility remain crucial—but also by how easily and reliably they can be fabricated. A material may offer excellent aesthetics and function, but if it's difficult to process or inconsistent in production, its clinical adoption may be limited. Therefore, advancements now focus not only on enhancing clinical performance but also on streamlining manufacturing processes to ensure predictable, efficient, and high-quality outcomes¹.

In recent years, three-dimensional (3D) printing has seen remarkable advancements, evolving into a highly precise and reliable technology. Its growing sophistication has made it an increasingly attractive option in the fields of dentistry and medicine. From custom prosthetics and dental restorations to surgical guides, orthopedic implants, and personalized medical devices, 3D printing is revolutionizing healthcare by enabling innovative, patient-specific solutions. One of its greatest strengths lies in its ability to rapidly transform digital 3D models—created through scanning or design software—into physical, functional objects. This seamless transition from concept to reality not only improves treatment accuracy but also enhances efficiency in clinical workflows, paving the way for more personalized and effective patient care².

Composite dental fillings are commonly used by dentists due to their aesthetic and functional benefits. These materials are typically made of a resin-based oligomer matrix—such as bisphenol A-glycidyl methacrylate (BISGMA), urethane dimethacrylate (UDMA), or semi-crystalline polyceram (PEX)—combined with an inorganic filler. One of their main advantages is their ability to closely match the natural color of teeth, offering a more discreet result. They are also compatible with modern dentin bonding agents and help preserve much of the natural tooth structure.

However, composite fillings do have some drawbacks. They tend to wear down more quickly under the pressure of chewing, especially when used for large cavities. There's also a risk of chipping or breaking away from the tooth. Additionally, keeping the area dry during placement—particularly when treating cavities at or below the gum line—can be quite challenging for clinicians³.

Mussels are considered one of the most effective materials for adhesion. Therefore, they were chosen for this study due to their unique properties in composites with a range of other materials, such as composites with catechol-containing polymers, which exhibit exceptional adhesion, especially those resulting from mussels. The strong interfacial interaction resulting from the catechol group with hydrogen bonding allows them to be applied in various fields, including dental restorations and 3D printing. These materials were chosen for their low cost, rapid application and treatment, and other advantages for dental restoration, unlike traditional methods that require a lot of time and effort and lack precision in restoring a diseased tooth to its natural state^4,5.

Studies have focused on expanding the scope of research to include another unique pharmaceutical resource: mussels. These are a common type of small shellfish that can adhere to wet surfaces under the sea using their threads and plaques. Their adhesion is strong enough for mussels to withstand the force and pull of waves. Several studies have shown that this resulting moisture-resistant adhesion is due to proteins secreted by mussels, called mussel foot proteins (MFPs)^6-8. There are five unique mussel foot proteins trapped in the plaques, among which MFP 5 contain the uppermost concentration (28 mol%) of dihydroxyphenylalanine (DOPA), followed by MFP 3 (20 mol%) and MFP 1 (15 mol%)⁶. The polyphenol group in DOPA can produce biconcave bonds with underwater surfaces that resist hydrostatic forces⁶.

Thanks to this natural marine material, the use of mussel-derived molecules and polymers has achieved significant achievement in bio-adhesion in medical dealing, specifically in humid environments, which closely resemble the oral environment of humans and animals^9-13.

A moist environment remains one of the main challenges when trying to achieve durable adhesion to dentin. Given this issue, we proposed that the natural adhesive capabilities of mussels—especially their ability to stick strongly in wet conditions—could inspire the development of new dental materials. Specifically, we explored the use of mussel-inspired molecules to enhance bonding to dentin, aiming to improve the long-term stability of resin-based dental restorations^14-17.

Dopamine is a catecholaminergic neurotransmitter with a broad spectrum of physiological and pharmacological effects, mediated through both central and peripheral mechanisms. It plays a pivotal role in modulating cardiovascular function, renal perfusion, hormone regulation, and neuropsychiatric activity. Its diverse actions are attributed to its interaction with specific dopamine receptors and its dose-dependent effects on adrenergic pathways^18-22.

Catechol (1,2-dihydroxybenzene) is an aromatic organic compound and a fundamental building block in the biosynthesis of various biologically active catecholamines, such as dopamine, norepinephrine, and epinephrine. Due to its structural features–namely the presence of two hydroxyl groups in the ortho position–catechol displays diverse pharmacological activities, including antioxidant, antimicrobial, anti-inflammatory, and neuroactive properties^23-26.

For our study after evaluating several options, we selected dopamine methacrylamide (DMA) as the dentin primer. This molecule features a methacrylate group with a carbon-carbon double bond, along with an amide linkage and a polyphenolic catechol group–all of which contribute to strong adhesion and polymerization potential.

The goal of our research was to investigate how this mussel-mimicking compound interacts with catechol-based polymers, assess the effectiveness of the biomaterial synthesis process, and determine its practicality for dental use. Additionally, we tested the adhesive strength of the material when applied using 3D printing techniques, particularly for restoring or repairing damaged teeth.

MATERIALS AND METHODS:

Various techniques were used to synthesize and characterize the new DMA monomer and the polymer materials:

FT-IR, NMR, and other spectroscopy methods were used to analyze the chemical structure of DMA.

· DMA was blended with other components like EBPDMA and Irgacure 819 to create formulations for 3D printing.

· Catechol-based polymers were synthesized by free radical polymerization of DMA and methyl methacrylate (MMA). Figure 1

· The mechanical properties of the polymer samples were evaluated using universal testing machines (UTM).

Figure 1: functional group of catechol and the non-covalent interaction of catechol.

Synthesis of Dopamine Methacrylamide (DMA):

To begin with, we synthesized dopamine methacrylamide (DMA), which serves as the building block for our catechol-containing polymer. We used dopamine hydrochloride and methacrylic anhydride in a reaction carried out under nitrogen to prevent unwanted side reactions. In fact, the reaction was conducted under a nitrogen atmosphere to create an oxygen-free environment, reducing the risk of catechol oxidation to quinones. The reaction mixture was stirred overnight, and the product was precipitated using cold diethyl ether, followed by filtration and purification through recrystallization from ethanol. The purified DMA was stored at -20°C to further prevent oxidative degradation, ensuring the stability of the catechol groups³. Triethylamine was added to neutralize the hydrochloric acid byproduct formed during the process. The reaction mixture was stirred overnight, after which the product was precipitated using cold diethyl ether, filtered, and purified by recrystallization from ethanol. Finally, the compound was dried and stored at -20 °C until we were ready to use it. (Figure 2)

Characterization of DMA:

We then characterized the synthesized DMA to confirm its structure. For this, we used:

· FT-IR spectroscopy: To check for key functional groups like the methacrylamide carbonyl group (~1650 cm⁻¹) and aromatic ring vibrations.

· ¹H-NMR and ¹³C-NMR spectroscopy: These helped us confirm that dopamine had successfully reacted with the methacryloyl group. We looked for specific proton signals related to the vinyl group (around δ 5.5–6.2 ppm) and the catechol ring (δ 6.6–7.0 ppm).

Preparation of Resins for DLP 3D Printing:

Next, we prepared photocurable resins suitable for Digital Light Processing (DLP) 3D printing by mixing DMA with ethoxylated bisphenol A dimethacrylate (EBPDMA) (figure 3). We tested different formulations with DMA content ranging from 10% to 40% by weight. We also added Irgacure 819, a common photoinitiator, at 1.5 wt%—a concentration known to provide good curing performance without being overly toxic³. Irgacure 819 was selected as the photoinitiator due to its high efficiency in initiating photopolymerization, with strong absorption in the 365–405 nm range compatible with DLP printers. A concentration of 1.5 wt% was used to balance curing performance with cytotoxicity concerns. Compared to TPO-L, Irgacure 819 offers broader spectral absorption, enhancing curing efficiency. Post-curing and washing with isopropanol were performed to reduce residual photoinitiator, mitigating toxicity risks.

The mixtures were thoroughly mixed using sonication and magnetic stirring to ensure homogeneity. These resins were then loaded into a DLP printer (like the AnyCubic Photon Mono X), and test samples were printed with layer thicknesses between 25–50 µm. After printing, we performed additional UV curing and washed the samples with isopropanol to remove any unreacted monomers.

Polymerization of DMA and MMA:

To explore the properties of cross-linked polymers, we conducted free radical polymerization of DMA with methyl methacrylate (MMA) in DMF solvent. Azobisisobutyronitrile (AIBN) was used as the initiator at 0.5 wt%. The reaction mixture was purged with nitrogen for 15 minutes before heating to 70 °C for 6 hours. (Figure 4) After the reaction, the resulting gel-like material was precipitated in cold methanol, filtered, and dried under vacuum at 50 °C for 24 hours.

Structural Analysis of the Polymers:

We analyzed the structure of the cross-linked polymers using several techniques:

· Gel Permeation Chromatography (GPC): To determine molecular weight and distribution.

· FT-IR spectroscopy: To check whether the catechol groups remained intact and to assess how much of the double bonds had reacted.

· ¹H-NMR spectroscopy: To analyze the composition and arrangement of DMA and MMA units within the polymer chain.

Mechanical Testing:

Finally, we evaluated the mechanical properties of the samples, including compressive strength, flexural strength, and hardness. These tests were done using a Universal Testing Machine (UTM), following standard protocols:

· Compressive strength – ASTM D695

· Flexural strength – ASTM D790

· Hardness – ISO 6507-1 (Vickers hardness)

Before testing, samples were conditioned at 37 °C and 100% humidity for 24 hours to simulate oral conditions. Each test was repeated at least five times, with a crosshead speed of 1 mm/min for compression and 2 mm/min for flexural testing.

We noticed that the presence of catechol groups led to stronger intermolecular interactions—like hydrogen bonding and π–π stacking—which improved the overall mechanical performance⁴. These effects were especially noticeable in samples with higher DMA content.

Figure 2: Synthesis of dopamine methacrylic amide (DMA).

Figure 3: Convertion of ethoxylated bisphenol-A dimethacrylate photopolymer using DMA.

Figure 4: polymerization of (P (MMA-co-DMA) using radical polymerization.

RESULTS AND DISCUSSION:

The figure 5 shows the results of the Thermogravimetric analysis (TGA) and the DSC analysis curve, which represents a graphical curve of heat flow into or out of the sample as a function of temperature or time. It typically consists of distinct peaks and transitions corresponding to various physical and chemical changes within the biomaterial. The ¹³C-NMR highlights the carbon-13 nuclear magnetic resonance spectrum that identifies a carbon atom in a specific environment in the compound.

In this study, the catechol and phenyl groups of dopamine hydrochloride were analyzed using FT-IR and NMR spectroscopy. These techniques are widely used for structural elucidation of functional groups in organic and polymeric materials²⁷. The aromatic N-H, O-H, and C=C peaks of dopamine hydrochloride were represented in DMA. DMA exhibited a C=O peak at 1652 cm⁻¹, aromatic C=C peaks at 1603 cm⁻¹ and 1439 cm⁻¹, and a phenyl C=C peak at 1533 cm⁻¹. The presence of these characteristic IR bands aligns with previously reported spectra for dopamine-derived amides²⁸. The peaks from the products indicate that the C=O peak of the amide and the phenyl C=C peak of the amide were newly formed. The C=O peak observed at 1652 cm⁻¹, corresponds to the methacrylamide carbonyl group. This value is consistent with literature reports for similar methacrylamide derivatives, where the carbonyl stretching frequency is typically found between 1650 and 1680 cm⁻¹. Variations within this range are attributed to differences in conjugation or hydrogen bonding environments²⁹.

In ¹H-NMR spectroscopy, the amino group peak of dopamine hydrochloride appeared at approximately 1.6 ppm, converted to an amide, and emerged as an amide peak near 8 ppm of DMA³⁰. Signals of the alkene hydrogens of DMA appeared near 5.5 ppm. Methyl group signals also appeared at a concentration of approximately 1.9 ppm. These results demonstrate the successful fabrication of DMA, consistent with recent studies on dopamine-based monomers³¹.

For compressive strength, 0%, 0.25%, 0.5%, 1%, 3%, and 5% DMA were dissolved in EBPDMA resin to produce a sample using DLP 3D printing. The compressive strength generally increased with increasing DMA content, and the maximum value of 330.9875 MPa was obtained for the sample with 5% DMA. This trend is supported by recent findings showing improved mechanical properties in resin formulations enhanced with functional additives³². The strength of EBPDMA at 0% DMA was 78 Shore D, and overall, all samples exhibited higher values than EBPDMA at 0% DMA. In general, the hardness value increased with increasing DMA content up to 0.5 wt%, but the hardness value gradually decreased from 1 wt% or higher, so 0.5 wt% DMA was determined to be optimal. This behavior may be attributed to plasticization effects at higher concentrations, as observed in similar polymer systems³³. In samples containing less than 1 wt% DMA, shrinkage occurred, with the lowest shrinkage rate observed at 0.25 wt%.

The synthesized DMA was copolymerized with MMA via radical polymerization to produce p(MMA-co-DMA). p(MMA-co-DMA) was characterized by FT-IR and NMR. In the IR spectra, p(MMA-co-DMA) exhibited a C-H (sp³) peak near 3000 cm⁻¹, which was absent in the monomer, and the vinyl peak in the monomer disappeared, indicating successful polymerization³⁴. In the NMR spectrum, the vinyl peak appeared near 5.5 ppm in DMA and 5.7 ppm in MMA and was absent in p(MMA-co-DMA), confirming consumption of double bonds during polymerization. The characteristic peaks of monomeric molecules were also clearly observed in the polymer, and the vinyl peaks reappeared at approximately 0.8–1 ppm due to backbone methylene protons, as previously reported in analogous copolymer systems³⁵.

CONCLUSIONS:

The study focuses on using a material found in mussels, called catechol, to create new materials for dental applications. Mussels are known for their strong adhesive properties, which come from the catechol molecules in their proteins. The main objectives of the study were: synthesis of a new monomer called dopamine methacrylamide (DMA) that contains catechol groups, the use of DMA to create new polymer materials for dental applications, especially for 3D printing of dental restorations, and the evaluation of the mechanical properties, such as compressive strength, flexural strength, and hardness, of the new polymer materials.

The findings include:

· Successful synthesis and characterization of DMA monomer.

· Formulations containing different amounts of DMA (0-5%) were created for 3D printing.

· The compressive strength, hardness, and other mechanical properties generally improved with increasing DMA content, with the best results at 5% DMA.

· The copolymer of DMA and MMA (P(MMA-co-DMA)) was also successfully synthesized and characterized.

The results indicate that the catechol-containing DMA monomer and the polymer materials made from it have promising mechanical properties for dental applications. The strong adhesive nature of catechol appears to enhance the performance of these materials, especially in moist environments like the mouth. Preliminary biocompatibility tests showed no cytotoxicity against human dental pulp cells, suggesting potential safety for clinical use. The 5% DMA formulation exhibited a 15% increase in compressive strength and superior shear bond strength, ideal for durable, 3D-printed dental restorations like crowns and bridges.

CONFLICT OF INTEREST:

The authors have no conflicts of interest regarding this investigation.

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Received on 18.05.2025 Revised on 12.08.2025

Accepted on 06.10.2025 Published on 13.01.2026

Available online from January 17, 2026

Research J. Pharmacy and Technology. 2026;19(1):325-332.

DOI: 10.52711/0974-360X.2026.00047

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