Adhesive compositions

Patent metadata

Field	Value
Publication number	US-9657203-B2
Application number	US-201514696611-A
Country	US
Kind code	B2
Filing date	Apr 27, 2015
Priority date	Oct 26, 2012
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

A two part curable composition is provided, where the composition comprises:
(a) a first part comprising:
(i) a (meth)acrylate component; (ii) 1,4-quinones, such as napthoquinone or benzoquinone and derivatives thereof in an amount less than or equal to about 0.05 weight percent; (iii) triaryl or alkaryl phenylphosphine in an amount greater than or equal to about 0.5 weight percent; and (iv) an amine;

and

(b) a second part comprising:
(i) benzoyl peroxide in an amount greater than about 1.0 weight percent.

First claim

What is claimed is:

1. A two part curable composition comprising:
(a) a first part comprising:
(i) a (meth)acrylate component;
(ii) a 1,4-quinone in an amount less than or equal to about 0.05 weight percent;
(iii) triaryl or alkaryl phosphine as an accelerator in an amount greater than or equal to about 0.5 weight percent; and
(iv) an amine;

and
(b) a second part comprising:
(i) a peroxide-based oxidant.

2. The composition of claim 1 , wherein the composition has an open time at room temperature of at least about 2 minutes and a fixture time of less than about 80 seconds at a bondline temperature of 40° C. when used to adhesively join substrates, and a shelf life of at least one of at a temperature of 38° C. of greater than 4 weeks, at a temperature of 55° C. of greater than 3 days and at a temperature of 82° C. of greater than 7 hours, as measured by manual dispensability through a dual barrel 50 mL.

3. The composition of claim 1 , wherein the (meth)acrylic component of the first part is selected from the group consisting of methyl (meth)acrylate, 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, isobornyl (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.

4. The composition of claim 1 , wherein the amine of the first part is selected from the group consisting of 1,8-diazabicyclo(5.4.0)undec-7-ene, 1,4-diazabicyclo(2.2.2)octane, triethylamine, tetramethylguanidine, dimethyl-p-toluidine, dimethyl aniline, dihydroxyethyl aniline, dihydroxy ethyl p-toluidine, dimethyl-o-toluidine, dimethyl aniline, benzoyl-thiourea, a trialkyl amine, tributyl amine, dihydro pyridine, phenyl dihydro pyridine, dihydropyridine derivatives, aldehyde condensation products of alkyl, aromatic, heterocyclic amines, and combinations thereof.

5. The composition of claim 1 , wherein the amine is a toluidine.

6. The composition of claim 1 , further comprising in the first part methacrylic acid.

7. The composition of claim 1 , further comprising in the second part an epoxy resin.

8. The composition of claim 7 , wherein the epoxy resin of the second part is selected from the group consisting of cycloaliphatic epoxides, epoxy novolac resins, bisphenol-A epoxy resins, bisphenol-F epoxy resins, bisphenol-A epichlorohydrin based epoxy resin, alkyl epoxides, limonene dioxide, polyfunctional epoxides, and combinations thereof.

9. The composition of claim 2 , wherein the substrates are each constructed from metals.

10. The composition of claim 2 , wherein the substrates are each constructed from plastics.

11. The composition of claim 2 , wherein one of the substrates is constructed from a metal and the other is constructed from a plastic.

12. The composition of claim 2 , wherein one of the substrates is constructed from anodized aluminum and the other being constructed from PC/ABS.

13. A method of bonding a first surface to a second surface, comprising:
providing a two part composition comprising:
(a) a first part comprising:
(i) a (meth)acrylate component;
(ii) a 1,4-quinone in an amount less than about 0.05 weight percent;
(iii) a triaryl or arylalkyl phosphine as an accelerator in an amount greater than or equal to about 0.5 weight percent; and
(iv) an amine; and

(b) a second part comprising:
(i) a peroxide-based oxidant,

providing a first surface and a second surface;
applying the two part composition to at least one of the surfaces wherein when the first and second parts are mixed and applied to at least one substrate, the composition shows at least 2 minutes of open time; and
mating the surface such that the composition shows a fixture time of less than 80 seconds at a bondline temperature of about 40° C. at which point the mated surfaces can support 3 kg load.

14. The composition of claim 1 , wherein the peroxide-based oxidant is benzoyl peroxide in an amount greater than about 1.0 weight percent.

15. The composition of claim 1 , wherein the peroxide-based oxidant is benzoyl peroxide in an amount up to about 75 weight percent.

16. The composition of claim 1 , wherein the 1,4-quinone is naphthoquinone in an amount less than or equal to about 0.005 weight percent.

17. The composition of claim 1 , wherein the 1,4-quinone is benzoquinone in an amount less than or equal to about 0.05 weight percent.

18. The composition of claim 2 , wherein the composition has a shelf life at a temperature of 38° C. of greater than 6 weeks, at a temperature of 55° C. of greater than 7 days and at a temperature of 82° C. of greater than 24 hours.

19. A two part curable composition comprising:
(a) a first part comprising:
(i) a (meth)acrylate component comprising methyl (meth)acrylate;
(ii) naphthoquinone in an amount less than or equal to about 0.05 weight percent;
(iii) triphenyl phosphine as an accelerator in an amount greater than or equal to about 0.5 weight percent; and
(iv) an amine;

and
(b) a second part comprising:
(i) a peroxide-based oxidant.

20. The composition of claim 19 , wherein the triphenyl phosphine is present in an amount greater than or equal to about 0.75 weight percent.

21. The composition of claim 1 , further comprising in the first part a vinyl-terminated polybutadiene.

22. The composition of claim 1 , wherein the vinyl-terminated polybutadiene is in the liquid form at room temperature.

23. The composition of claim 19 , further comprising in the first part a vinyl-terminated polybutadiene.

24. The composition of claim 19 , wherein the vinyl-terminated polybutadiene is in the liquid form at room temperature.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Murray James
• Schuft Charles F
• Cheng Chih-Min

Classifications

• B32B37/12

  characterised by using adhesives · CPC title

• C09J163/00

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C09J2203/10

  Chemistry & Metallurgy · mapped topic

• C09J4/00 Primary

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C08K5/50

  Phosphorus bound to carbon only · CPC title