Adhesive compositions containing reactive silsesquioxanes

Patent metadata

Field	Value
Publication number	US-2019136102-A1
Application number	US-201816185466-A
Country	US
Kind code	A1
Filing date	Nov 9, 2018
Priority date	May 9, 2016
Publication date	May 9, 2019
Grant date	—

Abstract

The present invention provides adhesive compositions, sometimes in a two part configuration which include a first part containing a (meth)acrylic component, an organic peroxide and a silsesquioxane and a second part containing a (meth)acrylic component, a nitrogen-containing compound and a metal salt.

First claim

What is claimed is:

1 . An adhesive composition in a two part configuration comprising:
(a) a first part comprising a (meth)acrylic component and an organic peroxide; and (b) a second part comprising a (meth)acrylic component, a nitrogen-containing compound and a metal salt, wherein at least one of the first part or the second part further comprises a silsesquioxane.

2 . The composition of claim 1 , wherein the silsesquioxane comprises one or more (meth)acryl groups attached thereto.

3 . The composition of claim 1 , wherein the silsesquioxane comprises the structure:

wherein one or more R groups is a (meth)acryloxyakyl group.

4 . The composition of claim 2 , wherein the R group is (meth)acryloxypropyl.

5 . The composition of claim 1 , wherein the silsesquioxane comprises the structure (II):

wherein R is a cyclohexyl group.

6 . The composition of claim 1 , wherein the (meth)acrylic component of at least one of the first part (A) or the second part (B) is selected from the group consisting of methyl (meth)acrylate, (meth)acrylic acid, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, phenyl (meth)acrylate, tolyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, stearyl (meth)acrylate, glycidyl (meth)acrylate, 2-aminoethyl (meth)acrylate, γ-(meth)acryloyloxypropyl trimethoxysilane, (meth)acrylic acid-ethylene oxide adduct, trifluoromethylmethyl (meth)acrylate, 2-trifluoromethylethyl (meth)acrylate, 2-perfluoroethylethyl (meth)acrylate, 2-perfluoroethyl-2-perfluorobutylethyl (meth)acrylate, 2-perfluoroethyl (meth)acrylate, perfluoromethyl (meth)acrylate, diperfluoromethylmethyl (meth)acrylate, 2-perfluoromethyl-2-perfluoroethylmethyl (meth)acrylate, 2-perfluorohexylethyl (meth)acrylate, 2-perfluorodecylethyl (meth)acrylate, 2-perfluorohexadecylethyl (meth)acrylate, ethoxylated trimethylolpropane triacrylate, trimethylol propane trimethacrylate, dipentaerythritol monohydroxypentacrylate, pentaerythritol triacrylate, ethoxylated trimethylolpropane triacrylate, 1,6-hexanedioldiacrylate, neopentyl glycoldiacrylate, pentaerythritol tetraacrylate, 1,2-butylene glycoldiacrylate, trimethylopropane ethoxylate tri(meth)acrylate, glyceryl propoxylate tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, dipentaerythritol monohydroxy penta(meth)acrylate, tri(propylene glycol) di(meth)acrylate, neopentylglycol propoxylate di(meth)acrylate, 1,4-butanediol di(meth)acrylate, polyethyleneglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, butylene glycol di(meth)acrylate, ethoxylated bisphenol A di(meth)acrylate, and combinations thereof.

7 . The adhesive composition of claim 1 , further comprising a block copolymer.

8 . The composition of claim 1 , wherein the silsesquioxane is present in Part A.

9 . The composition of claim 1 , wherein the silsesquioxane is present in Part B.

10 . A method of preparing a two-part adhesive composition comprising:
(a) forming a first part (A) comprising a (meth)acrylic acid component and an organic peroxide; and (b) forming a second part (B) comprising a (meth)acrylic acid component, a nitrogen-containing component and a metal salt, wherein at least one of the first part or the second part further comprises a silsesquioxane.

11 . The method of claim 10 , wherein the silsesquioxane comprises one or more (meth)acryloxyalkyl groups attached thereto.

12 . The method of claim 10 , wherein the organic portion of the silsesquioxane comprises cyclohexyl groups and silanol groups.

13 . A method of bonding a first surface to a second surface, comprising:
providing a two part composition comprising:
(a) a first part (A) comprising a (meth)acrylic component and an organic peroxide; and
(b) a second part (B) comprising a (meth)acrylic component, a nitrogen-containing compound and a metal salt, wherein at least one of the first part or the second part further comprises a silsesquioxane;

where providing a first surface and a second surface in a mating relationship and disposing the composition between the mated surfaces, wherein when the surfaces are mated they will have a cure time of about 20 minutes or less at 80° C.; and a fixture time of less than 5 minutes at which the bond will support 3 Kg.

14 . The method of claim 13 , wherein the silsesquioxane comprises one or more (meth)acryloxyakyl groups attached thereto.

15 . The method of claim 13 , wherein the first part and second are mixed in a ratio of 1:10 to 10:1 part (A) to part (B) by volume.

16 . An adhesive composition comprising:
(a) a (meth)acrylic component; (b) a curative package comprising an organic peroxide, a nitrogen-containing compound and a metal salt; and (c) a silsesquioxane.

17 . The composition of claim 16 , wherein the silsesquioxane comprises one or more (meth)acryloxyalkyl groups attached thereto.

18 . The composition of claim 16 , wherein the silsesquioxane comprises the structure:

wherein one or more R groups is a (meth)acryloxyalkyl group.

19 . The composition of claim 18 , wherein the silsesquioxane comprises silanol groups and cyclohexyl groups.

20 . The composition of claim 16 , wherein the silsesquioxane comprises the formula:

wherein R is a cyclohexyl group.

21 . The adhesive composition of claim 16 , further comprising a block copolymer.

22 . The composition of claim 16 , wherein the (meth)acrylic component is selected from the group consisting of methyl (meth)acrylate, (meth)acrylic acid, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, phenyl (meth)acrylate, tolyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, stearyl (meth)acrylate, glycidyl (meth)acrylate, 2-aminoethyl (meth)acrylate, γ-(meth)acryloyloxypropyl trimethoxysilane, (meth)acrylic acid-ethylene oxide adduct, trifluoromethylmethyl (meth)acrylate, 2-trifluoromethylethyl (meth)acrylate, 2-perfluoroethylethyl (meth)acrylate, 2-perfluoroethyl-2-perfluorobutylethyl (meth)acrylate, 2-perfluoroethyl (meth)acrylate, perfluoromethyl (meth)acrylate, diperfluoromethylmethyl (meth)acrylate, 2-perfluoromethyl-2-perfluoroethylmethyl (meth)acrylate, 2-perfIuorohexylethyl (meth)acrylate, 2-perfluorodecylethyl (meth)acrylate, 2-perfluorohexadecylethyl (meth)acrylate, ethoxylated trim

Assignees

• Henkel IP & Holding GmbH

Inventors

• Hurlburt Lynnette
• Sweeney Nigel
• Klemarczyk Philip T

Classifications

• C08K5/3432

  Six-membered rings · CPC title

• C08K5/098

  Metal salts of carboxylic acids · CPC title

• C08K5/14

  Peroxides · CPC title

• C08K5/5435

  containing oxygen in a ring · CPC title

• C09J5/06

  involving heating of the applied adhesive · CPC title