Core-sheath filaments including crosslinkable and crosslinked adhesive compositions and methods of making the same

Patent metadata

Field	Value
Publication number	US-11725308-B2
Application number	US-202017632771-A
Country	US
Kind code	B2
Filing date	Aug 12, 2020
Priority date	Aug 19, 2019
Publication date	Aug 15, 2023
Grant date	Aug 15, 2023

Abstract

A core-sheath filament including a crosslinkable adhesive core that can be cured using ultraviolet or visible light radiation. These crosslinkable adhesive core compositions can provide very high bond strength and are capable of replacing traditional mechanical fasteners in many industrial applications. Core-sheath filaments including such crosslinkable compositions, crosslinked compositions, articles containing these compositions, and methods of making the articles are provided. The crosslinkable compositions contain pendant aromatic ketone groups or pendant (meth)acryloyl groups that, upon exposure to ultraviolet radiation, result in the formation of crosslinks within the polymeric material. The crosslinked compositions can function as pressure-sensitive adhesives.

First claim

What is claimed is:

1. A core-sheath filament comprising:
a non-tacky sheath, wherein the non-tacky thermoplastic sheath exhibits a melt flow index of less than 15 grams per 10 minutes (g/10 min) when measured in accord with ASTM D1238 at 190° C.; and
a curable adhesive composition comprising (1) a curable (meth)acrylate copolymer having a weight average molecular weight in a range of 100,000 to 1,500,000 Da and (2) an optional photoinitiator, wherein the curable (meth)acrylate copolymer comprises:
a) a first monomeric unit of Formula (I) in an amount in a range of 50 to 99 weight percent based on a total weight of monomeric units in the curable (meth)acrylate copolymer

wherein
R 1 is hydrogen or methyl; and

R 2 is an alkyl, heteroalkyl, aryl, aralkyl, or alkaryl group;
b) a second monomeric unit of Formula (II) in an amount in a range of 1 to 13 weight percent based on the total weight of monomeric units in the curable (meth)acrylate copolymer

wherein
R 1 is hydrogen or methyl; and
R 4 is —OH, —NH 2 , a secondary amino group, a tertiary amino group, an (N,N-dialkylaminoalkyl)-O— group, (N,N-dialkylaminoalkyl)-N— group; and

c) a third monomeric unit of Formula (III) in an amount in a range of 0.05 to 5 weight percent based on the total weight of monomeric units of the curable (meth)acrylate copolymer

wherein
R 3 comprises 1) an aromatic ketone group that causes hydrogen abstraction from a polymeric chain when exposed to ultraviolet radiation or 2) a (meth)acryloyl group that undergoes free radical polymerization in the presence of the photoinitiator when exposed to ultraviolet or visible light radiation.

2. The core-sheath filament of claim 1 , wherein the non-tacky sheath comprises a polymer selected from the group consisting of a (meth)acrylic block copolymer, an ethylene methyl copolymer, and combinations thereof.

3. The core-sheath filament of claim 1 , wherein 1 to 10 percent of the longest cross-sectional distance of the core-sheath filament is the sheath and 90 to 99 percent of the longest cross-sectional distance of the core-sheath filament is the core.

4. The core-sheath filament of claim 1 , wherein the curable (meth)acrylate copolymer has a weight average molecular weight in a range of 200 kDa to 1500 kDa.

5. The core-sheath filament of claim 1 , wherein the curable adhesive composition further comprises an ionic crosslinking additive.

6. A method of making a core-sheath filament, the method comprising:
a) forming a core composition comprising the curable adhesive composition of claim 1 ;
b) forming a sheath composition comprising the non-tacky thermoplastic material of claim 1 ; and
c) wrapping the sheath composition around the core composition the core-sheath filament, wherein the core-sheath filament has an average longest cross-sectional distance in a range of 1 to 20 millimeters.

7. The method of claim 6 , wherein the wrapping the sheath composition around the core composition comprises co-extruding the core composition and the sheath composition such that the sheath composition surrounds the core composition.

Assignees

• 3M Innovative Properties Company

Inventors

• Behling Ross E
• Chastek Thomas Q
• Napierala Mark E
• Kugel Alexander J
• West Shaun M
• Waid Robert D
• Young Jacob D

Classifications

• D01F8/10 Primary

  with at least one other macromolecular compound obtained by reactions only involving carbon-to-carbon unsaturated bonds as constituent · CPC title

• B29C64/118

  using filamentary material being melted, e.g. fused deposition modelling [FDM] · CPC title

• B33Y70/00

  Materials specially adapted for additive manufacturing · CPC title

• C09J133/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• B29K2033/12

  Polymers of methacrylic acid esters, e.g. PMMA, i.e. polymethylmethacrylate · CPC title