Bismaleimide-based solution for inkjet ink for three dimensional printing

Patent metadata

Field	Value
Publication number	US-11161995-B2
Application number	US-201716316356-A
Country	US
Kind code	B2
Filing date	Jul 5, 2017
Priority date	Jul 11, 2016
Publication date	Nov 2, 2021
Grant date	Nov 2, 2021

Abstract

A polyimidc-based solution for inkjet printing includes an α,ω-Bismaleimide(BMI) terminated oligomer, wherein said α,ω-Bismaleimide terminated oligomer is delined by formula (I), wherein R represents an aliphatic, an aromatic or mixed aliphatic and aromatic groups.

First claim

What is claimed is:

1. A curable liquid composition for inkjet 3D printing comprising:
(A) Bismaleimide (BMI) α,{acute over (ω)}-terminated compound defined by the general formula (1):

where “-R-” is a bivalent spacer that include hydrocarbon group comprising alkylene-, alkylidene-, arylene-, aralkylene-, alkarylene- groups, and groups, containing heteroatoms comprising Si, O, S, N and P.
(B) Organic diluent or solvent
(C) Reactive additives, wherein said reactive additives (C) comprise curing initiators, reagents and surfactants, and wherein said α,{acute over (ω)}-BMI-compound (A) is used as a stable suspension of a micronized powder in said organic diluent (B) in combination with said reactive additives and surfactants (C).

2. The composition according to claim 1 , wherein said α,{acute over (ω)}-BMI-compounds (A) are used as a low viscous solution in a suitable Organic solvent (B) in combination with said reactive additives (C).

3. The composition according to claim 1 , wherein said α,{acute over (ω)}-BMI-compounds (A) undergoes quick thermal- and (or) photo-initiating curing during inkjet 3D printing process (1-20 sec. per layer) in the presence of the Reactive additives (C).

4. The composition according to claim 1 , wherein said solvents (B) having a boiling temperature below 190° C. and an evaporation rate lower than 1.

5. The composition according to claim 1 , wherein said solvents (B) comprises Alcohols, Mono-alkyl ethers, comprising 2-Ethoxyethanol or 2-Butoxyethanol and Alkyl carboxylates comprising n-Alkyl Acetates and n-Alkyl Propionate with Alkyl=C n H 2n+1 , n=4-8.

6. The composition according to claim 1 , wherein said Bismaleimide (BMI) α,{acute over (ω)}-terminated compound is mixed with a solvent to form a BMI-based solution that has a viscosity of 7-88 mPa.s at 40-65° C.

7. The composition according to claim 1 , wherein said α,{acute over (ω)}-BMI-compound (A) has a molecular weight from 250 to 10,000 Dalton and can be represented as an individual compound or as a α,{acute over (ω)}-Bismaleimide-terminated oligomer.

8. A curable liquid composition for inkjet 3D printing comprising:
(A) Bismaleimide (BMI) α,{acute over (ω)}-terminated compound defined by the general formula (1):

where “-R-” is a bivalent spacer that include hydrocarbon group comrising alkylene-, alkylidene-, arylene-, aralkylene-, alkarylene- groups, and groups, containing heteroatoms comprising Si, O, S, N and P.
(B) Organic diluent or solvent
(C) Reactive additives, wherein said reactive additives (C) comprise curing initiators, reagents and surfactants, and
wherein said α,{acute over (ω)}-BMI-compound (A) is used in combination with said reactive additives, wherein one of said reactive additives comprises oligomeric polyamine containing reactive N-H bonds, that undergoes Michael addition reaction to said BMI-compound during the thermal curing process.

9. The composition according to claim 8 , wherein said α,{acute over (ω)}-BMI-compound (A) is used as a low viscous solution in a suitable Organic solvent (B) in combination with Reactive additives (C).

10. The composition according to claim 8 , wherein said α,{acute over (ω)}-BMI-compounds (A) undergoes quick thermal- or photo-initiating curing during inkjet 3D printing process in the presence of the Reactive additives (C).

11. A curable liquid composition for inkjet 3D printing comprising:
(A) Bismaleimide (BMI) α,{acute over (ω)}-terminated compound defined by the general formula

where “-R-” is a bivalent spacer that include hydrocarbon group comprising alkylene-, alkylidene-, arylene-, aralkylene-, alkarylene- groups, and groups, containing heteroatoms comprising Si, O, S, N and P.
(B) Organic diluent or solvent
(C) Reactive additives, wherein said reactive additives (C) comprise curing initiators, reagents and surfactants, and wherein said α,{acute over (ω)}-BMI-compound (A) has a molecular weight 689 Dalton and can be used alone or in a mixture with other BMI-compounds.

Assignees

• Soreq Nuclear Res Ct

Inventors

• Gouzman Irina
• Atar Nurit
• Verker Ronen
• Bolker Assaf
• Grossman Eitan

Classifications

• B33Y70/00

  Materials specially adapted for additive manufacturing · CPC title

• C08G73/12

  Unsaturated polyimide precursors · CPC title

• C09D179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C09D11/30

  Inkjet printing inks · CPC title

• C09D11/102 Primary

  containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds · CPC title