One component (1K) anaerobic curable composition

Patent metadata

Field	Value
Publication number	US-12152172-B2
Application number	US-202217747459-A
Country	US
Kind code	B2
Filing date	May 18, 2022
Priority date	Nov 18, 2019
Publication date	Nov 26, 2024
Grant date	Nov 26, 2024

Abstract

The present invention provides an one-component (1K) anaerobic curable composition comprising, based on the weight of the composition:
from 15 to 35 wt. % of a1) at least one (meth)acrylate monomer represented by Formula I:

H 2 C═CGCO 2 R 1   (I)
wherein: G is hydrogen, halogen or a C 1 -C 4 alkyl group; and,
R 1 is selected from C 1 -C 30 alkyl, C 3 -C 30 cycloalkyl, C 2 -C 20 alkenyl and C 2 -C 12 alkynyl;

from 5 to 25 wt. % of a2) at least one (meth)acrylate monomer represented by Formula II:

H 2 C═CQCO 2 R 2   (II)
wherein: Q may be hydrogen, halogen or a C 1 -C 4 alkyl group; and,
R 2 may be selected from C 6 -C 18 aryl, alkaryl and aralkyl;

from 35 to 75 wt. % of a3) at least one (meth)acrylate-functionalized oligomer; from 0.1 to 10 wt. % of b) at least one cure initiator; from 0.1 to 5 wt. % of c) at least one cure accelerator; from 1 to 5 wt. % of d) at least one cellulose mixed ester of which all of said ester groups are selected from C 1 -C 6 ester groups; and, from 1 to 5 wt. % of e) fumed silica.

First claim

What is claimed is:

1. One component (1K) anaerobic curable composition comprising, based on the weight of the composition:
from 15 to 35 wt. % of a1) at least one (meth)acrylate monomer represented by Formula I:
H 2 C═CGCO 2 R 1   (I)

wherein: G is hydrogen, halogen or a C 1 -C 4 alkyl group; and,
R 1 is selected from C 1 -C 30 alkyl, C 3 -C 30 cycloalkyl, C 2 -C 20 alkenyl and C 2 -C 12 alkynyl;

from 5 to 25 wt. % of a2) at least one (meth)acrylate monomer represented by Formula II:
H 2 C═CQCO 2 R 2   (II)

wherein: Q may be hydrogen, halogen or a C 1 -C 4 alkyl group; and,
R 2 may be selected from C 6 -C 18 aryl, alkaryl and aralkyl;

from 35 to 75 wt. % of a3) at least one (meth)acrylate-functionalized oligomer;
from 0.1 to 10 wt. % of b) at least one cure initiator;
from 0.1 to 5 wt. % of c) at least one cure accelerator;
from 1 to 5 wt. % of d) at least one cellulose mixed ester of which all of said ester groups are selected from C 1 -C 6 ester groups; and, from 1 to 5 wt. % of e) fumed silica.

2. The one component composition according to claim 1 , wherein R 1 in Formula I is selected from C 1 -C 18 alkyl and C 3 -C 18 cycloalkyl.

3. The one component composition according to claim 1 comprising from 15 to 30 wt. %, based on the weight of the composition, of a1) said at least one (meth)acrylate monomer represented by Formula I.

4. The one component composition according to claim 1 , wherein said at least one (meth)acrylate monomer represented by Formula II is selected from: benzyl (meth)acrylate; phenoxyethyl (meth)acrylate; phenoxydiethylene glycol (meth)acrylate; phenoxypropyl (meth)acrylate; and, phenoxydipropylene glycol (meth)acrylate.

5. The one component composition according to claim 1 comprising from 5 to 20 wt. %, based on the weight of the composition, of a2) said at least one (meth)acrylate monomer represented by Formula II.

6. The one component composition according to claim 1 , wherein said at least one (meth)acrylate functionalized oligomer is characterized by having: i) two or more (meth)acrylate functional groups per molecule; and/or, ii) a weight average molecular weight (Mw) of from 300 to 1000 daltons.

7. The one component composition according to claim 1 , wherein said at least one (meth)acrylate functionalized oligomer is selected from: (meth)acrylate-functionalized urethane oligomers; (meth)acrylate-functionalized polyepoxide resins; (meth)acrylate-functionalized polybutadienes; (meth)acrylic polyol (meth)acrylates; polyester (meth)acrylate oligomers; polyamide (meth)acrylate oligomers; and, polyether (meth)acrylate oligomers.

8. The one component composition according to claim 7 comprising at least one polyether (meth)acrylate oligomer.

9. The one component composition according to claim 1 comprising from 40 to 60 wt. %, based on the weight of the composition, of a3) said at least one (meth)acrylate-functionalized oligomer.

10. The one component composition according to claim 1 , wherein at least one cure initiator is selected from the group consisting of: cumene hydroperoxide (CHP); para-menthane hydroperoxide; t-butyl hydroperoxide (TBH); t-butyl perbenzoate; t-amyl hydroperoxide; 1,2,3,4-tetramethylbutyl hydroperoxide; benzoyl peroxide; dibenzoyl peroxide; 1,3-bis(t-butylperoxyisopropyl) benzene; diacetyl peroxide; butyl 4,4-bis (t-butylperoxy) valerate; p-chlorobenzoyl peroxide; t-butyl cumyl peroxide; di-t-butyl peroxide; dicumyl peroxide; 2,5-dimethyl-2,5-di-t-butylperoxyhexane; 2,5-dimethyl-2,5-di-t-butyl-peroxyhex-3-yne; and, 4-methyl-2,2-di-t-butylperoxypentane.

11. The one component composition according to claim 1 comprising from 0.1 to 5 wt. % of b) said at least one cure initiator, based on the total weight of the composition.

12. The one component composition according to claim 1 , wherein all of said ester groups of said at least one cellulose mixed ester are selected from C 1 -C 4 ester groups.

13. The one component composition according to claim 1 , wherein said at least one cellulose mixed ester has a glass transition temperature (T g ) of from 80° C. to 160° C., as measured by differential scanning calorimetry (DSC).

14. The one component composition according to claim 1 , wherein said fumed silica is characterized by at least one of: i) an average particle size of from 1 to 10 microns; ii) a specific surface area of from 100 to 250 m 2 /g; and, iii) a tap density of from 25 to 75 g/l.

15. The one component composition according to claim 1 , wherein the ratio by weight of fumed silica to said cellulose ester is in the range from 3:1 to 1:3.

16. The one component composition according to claim 1 , wherein said composition:
i) is essentially free of solvent; and,
ii) has a viscosity of from 3000 to 20000 mPa·s, as determined at 20° C. and 50% Relative Humidity (RH).

17. A cured product obtained from the one-component (1K) composition as defined in claim 1 .

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Trivedi Krunal
• Ghule Namdev
• Shah Jayesh P
• Khandagale Prasad

Classifications

• C09J101/14

  Mixed esters, e.g. cellulose acetate-butyrate · CPC title

• C09J11/04

  inorganic · CPC title

• C08L51/02

  grafted on to polysaccharides · CPC title

• C09D4/06

  {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 C09D159/00 - C09D187/00 · CPC title

• C09J133/10 Primary

  Homopolymers or copolymers of methacrylic acid esters · CPC title