IP Library Granted Patent US 6,855,748
Granted Patent B1
US 6,855,748 · App. 10/088,564 · Granted Feb 15, 2005

UV-curable compositions

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Quick Facts
Patent No.
US 6,855,748
App. No.
10/088,564
Granted
Feb 15, 2005
Kind
B1
Abstract

The present invention relates to UV-curable compositions, the process for preparing the compositions and to the use of the curable compositions. The compositions contain: a) at least one oxetane compound; b) at least one polyfunctional cycloaliphatic epoxy compound; c) at least one multifunctional hydroxy compound; and d) at least one curing agent.

Claims (33)

1. A curable composition comprising

a) at least one oxetane compound;

b) at least one polyfunctional cycloaliphatic epoxy compound;

c) at least one multifunctional hydroxy compound; and

d) at least one curing agent

wherein the ratio of the oxetane compound to the polyfunctional cycloaliphatic epoxy compound to the multifunctional hydroxy compound is from 7.5:1.5:1 to 150:10:1.

2. A curable composition according to claim 1 comprising

a) at least one oxetane compound of the formula

wherein R and R′ independently of one another represent aliphatic, cycloaliphatic or araliphatic groups and n represents an integer from one to four,

b) at least one polyfunctional cycloaliphatic epoxy compound containing a group of the formula

wherein R is a straight chain C 2 -C 6 alkylene group; and

c) at least one multifunctional hydroxy compound

Q(OH) n   (III)

in which Q represents an aliphatic, cycloaliphatic or araliphatic group and n an integer from 2 up to 128; and

d) at least one curing agent.

3. A curable composition according to claim 1 comprising

a) at least one oxetane compound selected from the group consisting of 3,3-[1,4-phenylene-bis(methyleneoxymethylene)]-bis(3-ethyloxetane), 3-methyl-3-α-ethanemethanol and 3-ethyl-3-oxethanemethanol;

b) at least one polyfunctional cycloaliphatic epoxy compound selected from the group consisting of 7-oxabicyclo[4.1.0]hept-3-ylmethyl ester-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid, 2,2′-oxy-bis(6-oxabicyclo[3.1.0]hexane),bis(7-oxabicyclo[4.1.0]hept-3-yl)methyl ester hexanedioic acid, 3,3′-(dioxane-2,5-diyl)-bis(7-oxabicyclo[4.1.0]heptane) and 2,2-bis(7-oxabicyclo[4.1.0]hept-3-ylcarbonyloxy)methyl]-1,3-propanediyl ester-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid;

c) a multifunctional hydroxy compound selected from the group consisting of pentaerythritol ethoxylate, polyethylene glycol, polytetrahydrofuran, polycaprolactone diol or triol, tripropylene glycol, glycerol propoxylate and dendritic polyols; and

d) at least one curing agent.

4. A curable composition according to claim 1 comprising

a) at least one oxetane compound;

b) at least one polyfunctional cycloaliphatic epoxy compound selected from the group consisting of 7-oxabicyclo[4.1.0]hept-3-ylmethyl ester-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid and bis(7-oxabicyclo[4.1.0]hept-3-yl)-methyl ester hexanedioic acid;

c) a multifunctional hydroxy compound selected from the group consisting of pentaerythritol ethoxylate, polyethylene glycol, polytetrahydrofuran, polycaprolactone diol or triol, tripropylene glycol, glycerol propoxylate and dendritic polyols; and

d) at least one curing agent.

5. A curable composition according to claim 1 , wherein the ratio of the oxetane compound to the polyfunctional cycloaliphatic epoxy compound to the multifunctional hydroxy compound is from 14:2:1 to 91:7:1.

6. A process for preparing a curable composition, which comprises

α) treating a composition comprising

a) at least one oxetane compound;

b) at least one polyfunctional cycloaliphatic epoxy compound; and

c) at least one multifunctional hydroxy compound; with

β) an ultraviolet (UV) curable curing agent

wherein the ratio of the oxetane compound to the polyfunctional cycloaliphatic epoxy compound to the multifunctional hydroxy compound is from 7.5:1.5:1 to 150:10:1.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Aug 26, 2021
From: HSBC BANK USA, NATIONAL ASSOCIATION
To: 3D SYSTEMS, INC.
Reel/Frame 057651/0374 →
SECURITY INTEREST Recorded Feb 27, 2019
From: 3D SYSTEMS, INC.
To: HSBC BANK USA, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 048456/0017 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN UNITED STATES TRADEMARKS AND PATENTS Recorded Jun 13, 2018
From: JPMORGAN CHASE BANK, N.A.
To: HUNTSMAN ADVANCED MATERIALS AMERICAS INC. (N/K/A HUNTSMAN ADVANCED MATERIALS AMERICAS LLC)
Reel/Frame 046352/0893 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2012
From: HUNTSMAN ADVANCED MATERIALS AMERICAS LLC
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 029370/0038 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 9, 2011
From: HUNTSMAN INTERNATIONAL LLC
To: 3D SYSTEMS, INC.
Reel/Frame 027355/0090 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE FROM ASSIGNMENT TO SECURITY AGREEMENT PREVIOUSLY RECORDED ON REEL 025855 FRAME 0192. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 28, 2011
From: DEUTSCHE BANK TRUST AG NEW YORK BRANCH, AS RESIGNING ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 026515/0735 →