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Non-isocyanate polyurethane inks for 3D printing

An ink and three-dimensional printing technology, applied in polyurea/polyurethane coatings, inks, 3D object support structures, etc., can solve problems such as toxicity, and achieve the effects of reducing toxicity, reducing skin sensitization or irritation, and high toughness

Active Publication Date: 2018-12-21
3D SYST INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Other inks provide both high resolution and high toughness, but may contain one or more toxic or bioincompatible substances

Method used

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  • Non-isocyanate polyurethane inks for 3D printing
  • Non-isocyanate polyurethane inks for 3D printing
  • Non-isocyanate polyurethane inks for 3D printing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0159] Cyclic carbonate monomer

[0160] The cyclic carbonate monomer with formula (A11) structure is prepared as follows, wherein R 1 for (CH 2 ) 8 . To a 500 mL 3-neck round bottom flask with a large Teflon®-coated football-shaped stirring magnet, a constant pressure addition funnel, and a condenser, was charged 12.0 g of sebacoyl chloride (SebCl), 10.4 g of triethylamine, and 80 g of methyltetrahydrofuran (mTHF ) solvent. Place this flask into a 190x 100 Pyrex filled with ice water ® (2.5L) crystallization dish and allow to stir / cool for about 30 min. 11.8 grams of glycerol carbonate and 20 grams of mTHF were added to a 150 mL constant pressure addition funnel, followed by gentle vortexing until the solid glycerol carbonate dissolved. The glycerol carbonate solution was added dropwise to the cooled sebacoyl chloride solution over a 30 minute period. Additional mTHF was added during subsequent reactions to facilitate stirring. Stirring was continued for about two ...

Embodiment 2

[0162] Cyclic carbonate monomer

[0163] A cyclic carbonate monomer having a structure of formula (A14) is prepared as follows, wherein R 1 for (CH 2 ) 2 , R 2 for CH 2 , and R 6 for CH 3 or H. for R 6 =CH 3 , was added 620.6 grams of isocyanatoethyl methacrylate (available from Synasia, Nantong, China) to a 2000 mL beaker with a large football-shaped stirring magnet coated with Teflon®. The solution was then stirred and heated in a 60°C silicone oil bath. A mixture of 476.7 grams of glycerol carbonate (from Huntsman Chemical) and 0.16 grams of dibutyltin dilaurate (from Sigmal Aldrich) was gradually added to the heated isocyanatoethyl methacrylate while maintaining the reaction temperature at 50 °C and between 80°C. After all the mixture had been added, 0.48 grams of BHT (from Sigma-Aldrich) was added and the resulting solution was stirred at 70-80°C for an additional 16 hours. The resulting product was a clear viscous liquid with no isocyanate peaks by FT-IR. ...

Embodiment 3

[0165] Cyclic carbonate monomer

[0166] The cyclic carbonate monomer having the structure of formula (A15) is prepared as follows. To a 500 mL beaker with a large football-shaped stirring magnet coated with Teflon® was added 55.57 grams of isophorone diisocyanate (from Sima-Aldrich), isobornyl methacrylate (IBOMA, from Evonik Industries) and 0.02 grams of diisocyanate (available from Evonik Industries). Dibutyltin laurate (available from Sigma Aldrich). The solution was stirred and heated in a silicone oil bath at 55-60°C. In the next step, 29.5 grams of glycerol carbonate (from Huntsman Chemical) was gradually added over 30 min while maintaining the reaction temperature between 50°C and 80°C. After all the glycerol carbonate had been added, 0.04 grams of BHT (from Sigma-Aldrich) was added and the resulting solution was stirred at 60-70°C for an additional hour. Then, 32.53 grams of hydroxyethyl methacrylate (from Sigma-Aldrich) were gradually added over 0.2 hours, and t...

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Abstract

In one aspect, inks for use with a 3D printer are described herein. In some embodiments, an ink described herein comprises a cyclic carbonate monomer and an amine monomer. Further, in some instances,an ink described herein also comprises an ethylenically unsaturated monomer such as a (meth)acrylate. Additionally, an ink described herein, in some cases, further comprises a colorant, such as a molecular dye, a particulate inorganic pigment, or a particulate organic colorant. An ink described herein may also comprise one or more additives selected from the group consisting of inhibitors, stabilizing agents, photoinitiators, and photosensitizers.

Description

[0001] Cross References to Related Applications [0002] This application claims priority under 35 U.S.C. § 119(e) to U.S. Provisional Patent Application Serial No. 62 / 305,051 filed March 8, 2016, which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to inks and, in particular, to inks for use in three-dimensional (3D) printing systems. Background of the invention [0004] Some commercially available 3D printers such as 3D Systems, ProJet manufactured by Rock Hill, South Carolina TM 3DPrinters, use inks, also known as build materials, that are ejected as liquids through print heads to form various 3D objects, articles or parts. Other 3D printing systems also use ink that is jetted through a print head, or otherwise dispensed onto a substrate. In some cases, the ink is solid at ambient temperature and turns liquid at elevated inkjet temperatures. In other cases, the ink is a liquid at ambient temperature. Additi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09D11/102B29C67/00C09D11/101C09D11/54
CPCC09D11/10C09D11/101C09D11/54B29C64/112B33Y70/00B33Y70/10B33Y10/00B33Y80/00B29K2075/00B29K2105/0058C09D4/00C09D175/12
Inventor B.吴J.班宁P.徐
Owner 3D SYST INC
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