Crosslinkable and crosslinked polymeric materials

Patent metadata

Field	Value
Publication number	US-10640686-B2
Application number	US-201716471630-A
Country	US
Kind code	B2
Filing date	Dec 19, 2017
Priority date	Dec 22, 2016
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

Crosslinkable compositions are provided that contain a) a polymeric material having at least two terminal dithiocarbamate groups or two terminal dithiocarbonate groups and b) a monomer composition that includes at least a crosslinking monomer having two or more ethylenically unsaturated groups. The polymeric materials in the crosslinkable compositions undergo chain extension and crosslinking reactions when exposed to actinic radiation in the ultraviolet region of the electromagnetic spectrum. Additionally, crosslinked compositions, articles that contain the crosslinkable compositions or the crosslinked compositions, and methods of making the articles are provided.

First claim

What is claimed is:

1. A crosslinkable composition comprising:
a) a polymeric material of Formula (I)

wherein
R 1 is hydrogen, alkyl, fluorinated alkyl, aryl, aralkyl, or substituted aryl;
X is oxy or—NR 2 — where group R 2 is hydrogen, alkyl, fluorinated alkyl, aryl, aralkyl, or substituted aryl;
each R 3 is an alkoxy, fluorinated alkoxy, or —N(R 4 ) 2 where each R 4 is an alkyl, fluorinated alkyl, or together with the nitrogen to which they are both attached form a heterocyclic ring;
each P is a polymeric block that comprises a polymerized product of a first monomer composition comprising at least one monomer having a single ethylenically unsaturated group;
y is an integer in a range of 1 to 5; and

b) a second monomer composition that is miscible with the polymeric material of Formula (I), the second monomer composition comprising a crosslinking monomer having at least two ethylenically unsaturated groups.

2. The crosslinkable composition of claim 1 , wherein y is equal to 1 and the polymeric material of Formula (I) is an elastomeric material.

3. The crosslinkable composition of claim 1 , wherein the crosslinkable composition comprises 5 to 99.99 weight percent polymeric material of Formula (I), 0.01 to 20 weight percent crosslinking monomer having at least two ethylenically unsaturated groups, and 2) 0 to 95 weight percent monomer having a single ethylenically unsaturated group, wherein each amount is based on a total weight of polymerized and polymerizable material.

4. The crosslinkable composition of claim 1 , wherein the polymeric material of Formula (I) has a weight average molecular weight in a range of 10,000 Daltons to 5 million Daltons.

5. The crosslinkable composition of claim 1 , wherein the crosslinkable composition further comprises a photoinitiator.

6. The crosslinkable composition of claim 5 , wherein the photoinitiator is of Formula (V)

wherein
R 1 i is hydrogen, alkyl, fluorinated alkyl, aryl, aralkyl, or substituted aryl;
X is oxy or —NR 2 — where group R 2 is hydrogen, alkyl, fluorinated alkyl, aryl, aralkyl, or substituted aryl;
each R 3 is an alkoxy, fluorinated alkoxy, or —N(R 4 ) 2 where each R 4 is an alkyl, fluorinated alkyl, or together with the nitrogen to which they are both attached form a heterocyclic ring.

7. The crosslinkable composition of claim 5 , wherein the photoinitiator is not of Formula (V).

8. The crosslinkable composition of claim 1 , wherein the crosslinking monomer has two or more (meth)acryloyl groups.

9. A crosslinked composition comprising the polymerized product of a crosslinkable composition of claim 1 .

10. The crosslinked composition of claim 9 , wherein the crosslinked composition further comprises a tackifier.

11. The crosslinked composition of claim 9 , wherein the crosslinked composition is a pressure-sensitive adhesive composition.

12. An article comprising:
a first substrate; and
a crosslinked composition layer positioned adjacent to the first substrate, the crosslinked composition layer comprising the crosslinked composition of claim 9 .

13. A method of making an article, the method comprising:
providing a first substrate;
applying a crosslinkable composition layer adjacent to the substrate, the crosslinkable composition layer comprising the crosslinkable composition of claim 1 ;
exposing the crosslinkable composition layer to actinic radiation to form a crosslinked composition layer, wherein the actinic radiation comprises ultraviolet radiation.

14. The method of claim 13 , wherein the substrate is in the form of a polymeric web.

15. The method of claim 13 , wherein the actinic radiation is from a light emitting diode.

Assignees

• 3M Innovative Properties Co

Inventors

• Roscoe Stephen B
• Gopalakrishnan Deepti
• Gryska Stefan H
• Griesgraber George W
• Yurt Serkan
• Fansler Duane D
• Lewandowski Kevin M
• Chatterjee Joon
• Lee Hae-Seung Harry
• Gaddam Babu N

Classifications

• C08F287/00 Primary

  Macromolecular compounds obtained by polymerising monomers on to block polymers · CPC title

• C09J4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C08F265/06

  Polymerisation of acrylate or methacrylate esters on to polymers thereof · CPC title

• C09J7/387 Primary

  Block-copolymers · CPC title

• C08F2438/03

  Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX] · CPC title