IP Library Granted Patent US 11,905,360
Granted Patent B2
US 11,905,360 · App. 16/754,561 · Granted Feb 20, 2024

Method for producing a cross-linkable polymer with the formation of oxazolidinones

Inventors: Dirk Achten (Leverkusen, DE); Thomas Buesgen (Leverkusen, DE); Roland Wagner (Leverkusen, DE); Florian Stempfle (Cologne, DE); Christoph Tomczyk (Leverkusen, DE)
Assignee: STRATASYS, INC.
C08G18/8125B33Y70/00C08G18/003C08G18/225C08G85/002B33Y70/10
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Quick Facts
Patent No.
US 11,905,360
App. No.
16/754,561
Granted
Feb 20, 2024
Kind
B2
Abstract

The invention relates to a method for producing a polymer comprising the following steps: (A) depositing a radically cross-linkable resin, obtaining a radically cross-linked resin; and (B) treating the radically cross-linked resin under conditions which are sufficient to trigger a chemical reaction that is different from the radical cross-linking in the radically cross-linked resin. The radically cross-linkable resin comprises a curable component, in which there are NCO groups, olefinic C═C double bonds and epoxide groups, and the chemical reaction in the radically cross-linked resin that is different from the radical cross-linking is the reaction of NCO groups and epoxide groups to form oxazolidinone groups.

Claims (30)

1. A process for producing a polymer, comprising:

Step A) depositing a free-radically crosslinkable resin to obtain a free-radically crosslinked resin; and

Step B) treating the free-radically crosslinked resin under conditions sufficient to trigger a chemical reaction different than free-radical crosslinking in the free-radically crosslinked resin,

wherein the free-radically crosslinkable resin comprises a curable component in which NCO groups, olefinic C═C double bonds, and epoxide groups are present, and

wherein the chemical reaction in the free-radically crosslinked resin different than free-radical crosslinking is a reaction of NCO groups and epoxide groups to form oxazolidinone groups.

2. The process as claimed in claim 1 , wherein the curable component comprises a curable compound that contains epoxide groups and olefinic C═C double bonds.

3. The process as claimed in claim 1 , wherein the curable component comprises a curable compound that contains NCO groups and olefinic C═C double bonds.

4. The process as claimed in claim 1 , characterized in that the free-radically crosslinkable resin further comprises a free-radical initiator and/or a Lewis acid catalyst.

5. The process as claimed in claim 1 , wherein treating the free-radically crosslinked resin under conditions sufficient to trigger a chemical reaction different than free-radical crosslinking in the free-radically crosslinked resin comprises heating at a temperature of ≥60° C.

6. The process as claimed in claim 1 , wherein the free-radically crosslinkable resin is applied as a coating to a substrate.

7. The process as claimed in claim 1 , wherein the process is an additive production process and wherein the polymer is in the form of an object formed from a precursor, wherein in step A) the free-radically crosslinked resin is the precursor and the treating in step B) results in obtaining the object.

8. The process as claimed in claim 7 , wherein the depositing in step A) comprises:

I) depositing the free-radically crosslinked resin on a carrier to obtain a ply of build material joined to the carrier that corresponds to a first selected cross section of the precursor;

II) depositing the free-radically crosslinked resin onto the ply of build material to obtain a further ply of build material that corresponds to a further selected cross section of the precursor that is joined to the previously applied ply;

III) repeating step II) until the precursor is formed;

wherein depositing the free-radically crosslinked resin at least in step II) further comprises exposure and/or irradiation of a selected region of the free-radically crosslinkable resin corresponding to the respectively selected cross section of the precursor and

the treating in step B) comprises:

IV) treating the precursor obtained in step III) under conditions sufficient for reaction of NCO groups and epoxide groups to form oxazolidinone groups.

9. The process as claimed in claim 8 , further comprising:

lowering the carrier by a predetermined distance before each step II) so that a layer of the free-radically crosslinkable resin forms above the uppermost ply of build material viewed in the vertical direction, and

exposing and/or irradiating the selected region of the layer of the free-radically crosslinkable resin corresponding to the respectively selected cross section of the precursor with an energy beam in step II),

wherein the carrier is positioned inside a container and is vertically lowerable in the direction of gravity, and

wherein the container contains the free-radically crosslinkable resin in an amount sufficient to cover at least the carrier and crosslinked resin deposited on the carrier.

10. The process as claimed in claim 8 , further comprising:

raising the carrier before each step II) by a predetermined distance so that a layer of the free-radically crosslinkable resin forms below the lowermost ply of build material viewed in the vertical direction,

providing the free-radically crosslinkable resin to the carrier from the container, and

simultaneously exposing and/or irradiating the selected region of the layer of the free-radically crosslinkable resin corresponding to the respectively selected cross section of the precursor with a plurality of energy beams in step II),

wherein the carrier is positioned inside a container and is vertically raisable counter to the direction of gravity.

11. The process as claimed in claim 8 , further comprising:

applying the free-radically crosslinkable resin from one or more print heads in step II) in accordance with the respectively selected cross section of the precursor and subsequently exposing and/or irradiating the respectively selected cross section of the precursor with an energy beam.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2024
From: COVESTRO DEUTSCHLAND AG
To: STRATASYS, INC.
Reel/Frame 069637/0063 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 8, 2020
From: ACHTEN, DIRK; BUESGEN, THOMAS; WAGNER, ROLAND; STEMPFLE, FLORIAN; TOMCZYK, CHRISTOPH
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 052346/0155 →
Priority Claims (1)
EP 17196378 · Oct 13, 2017 · regional
Continuity (1)
Related Publication 20200255584A1 · Aug 13, 2020