Title: Optically clear photo-polymerization resists for additive manufacturing of radiopaque parts

Abstract

According to one embodiment, a method includes contacting a triiodobenzoic acid with an oxalyl chloride in a solvent whereby triiodobenzoyl chloride is formed, contacting diethanolamine with triiodobenzoyl chloride where triiodobenzoic diol amine is formed, and forming an acrylate of triiodobenzoic diol amine with acryloyl chloride where an organoiodine compound is formed. According to another embodiment, an optically clear photopolymer resist blend for additive manufacturing includes a radiopaque pre-polymer compound where the compound includes at least one of the following: iodine, bromine, tin, lead, or bismuth. The resist blend also includes a photoinitiator, a polymerization inhibitor, and a base pre-polymer.

Inventors:

Saha, Sourabh Kumar; Oakdale, James Spencer

Issue Date:

2020-09-22

Research Org.:

Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1735288

Patent Number(s):

10781315

Application Number:

15/367,069

Assignee:

Lawrence Livermore National Security, LLC (Livermore, CA)

Patent Classifications (CPCs):

B - PERFORMING OPERATIONS B33 - ADDITIVE MANUFACTURING TECHNOLOGY B33Y - ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

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B - PERFORMING OPERATIONS B33 - ADDITIVE MANUFACTURING TECHNOLOGY B33Y - ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING

B33Y80/00 - Products made by additive manufacturing

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C231/02 - from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines

C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08F - MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

C08F222/18 - Esters containing halogen

B - PERFORMING OPERATIONS B33 - ADDITIVE MANUFACTURING TECHNOLOGY B33Y - ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING

B33Y70/00 - Materials specially adapted for additive manufacturing

C - CHEMISTRY C09 - DYES C09D - COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS

C09D4/00 - Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C63/70 - Monocarboxylic acids
C07C51/60 - by conversion of carboxylic acids or their anhydrides {or esters, lactones, salts} into halides with the same carboxylic acid part
C07C231/12 - by reactions not involving the formation of carboxamide groups
C07C233/69 - of an acyclic saturated carbon skeleton

B - PERFORMING OPERATIONS B33 - ADDITIVE MANUFACTURING TECHNOLOGY B33Y - ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING

B33Y10/00 - Processes of additive manufacturing

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DOE Contract Number:  

AC52-07NA27344

Resource Type:

Patent

Resource Relation:

Patent File Date: 12/01/2016

Country of Publication:

United States

Language:

English