Granted Patent B2

US 9,676,922 · App. 14/705,260 · Granted Jun 13, 2017

Abstract

Claims (33)

1. A two part heat and moisture resistant acrylic adhesive composition comprising:

a) an initiator part comprising at least one homopolymer dissolved in a (meth)acrylate monomer and a free radical initiator, wherein the at least one homopolymer is selected from the group consisting of poly(methyl methacrylate) (PMMA), polystyrene (PS), polydicyclopentadiene (PDCPD), and mixtures and blends thereof; and

b) an activator part comprising at least one homopolymer dissolved in a (meth)acrylate monomer, a pyridinic reducing agent, an organometallic curing promoter and a thiourea accelerator, wherein the at least one homopolymer is selected from the group consisting of poly(methyl methacrylate) (PMMA), polystyrene (PS), polydicyclopentadiene (PDCPD), and mixtures and blends thereof.

2. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the initiator part further comprises a toluenesulfonyl chloride co-initiator.

3. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the activator part further comprises a crosslinker.

4. The two part heat and moisture resistant acrylic adhesive composition of claim 3 , wherein the crosslinker is ethyleneglycol dimethacrylate.

5. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the (meth)acrylate monomer is a C 1 to C 20 alkyl ester of (meth)acrylic acid.

6. The two part heat and moisture resistant acrylic adhesive composition of claim 5 , wherein the C 1 to C 20 alkyl ester of (meth)acrylic acid is selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-ethyl hexyl (meth)acrylate, dicyclopentadienyl (meth)acrylate, isobornyl (meth)acrylate, and mixtures and blends thereof.

7. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the free radical initiator is cumene hydroperoxide.

8. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the organometallic curing promoter is an organometallic compound selected from the group consisting of cobalt, nickel, manganese or iron naphthenate, cobalt neodecanoate, copper octoate, copper acetylacetonate, iron hexoate, and iron propionate.

9. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the thiourea accelerator is selected from the group consisting of ethylene thiourea, 1-acetyl-2-thiourea, and 1-(2-pyridyl)-2-thiourea.

10. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the pyridinic reducing agent is 3,5-diethyl-1-phenyl-2-propyl-1,2-dihydropyridine (PDHP).

11. A method of bonding two objects together, the method comprising:

a) mixing an initiator part and an activator part together to form an adhesive,

wherein the initiator part comprises at least one homopolymer dissolved in a (meth)acrylate monomer and a free radical initiator, wherein the at least one homopolymer is selected from the group consisting of poly(methyl methacrylate) (PMMA), polystyrene (PS), polydicyclopentadiene (PDCPD), and mixtures and blends thereof, and

wherein the activator part comprises at least one homopolymer dissolved in a (meth)acrylate monomer, a pyridinic reducing agent, an organometallic curing promoter and a thiourea accelerator, wherein the at least one homopolymer is selected from the group consisting of poly(methyl methacrylate) (PMMA), polystyrene (PS), polydicyclopentadiene (PDCPD), and mixtures and blends thereof;

b) applying the adhesive to at least one surface of one of the two objects to be joined together; and

c) curing the adhesive to bond the two objects together.

12. The method according to claim 11 , wherein the initiator part further comprises a toluenesulfonyl chloride co-initiator.

13. The method according to claim 11 , wherein the activator part further comprises a crosslinker.

14. The method according to claim 13 , wherein the crosslinker is ethyleneglycol dimethacrylate.

15. The method according to claim 11 , wherein the (meth)acrylate monomer is a C 1 to C 20 alkyl ester of (meth)acrylic acid.

16. The method according to claim 15 , wherein the C 1 to C 20 alkyl ester of (meth)acrylic acid is selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 2-ethyl hexyl (meth)acrylate, dicyclopentadienyl (meth)acrylate, isobornyl (meth)acrylate, and mixtures and blends thereof.

17. The method according to claim 11 , wherein the free radical initiator is selected from the group consisting of benzoyl peroxide, cumene hydroperoxide, tertiary butyl hydroperoxide, dicumyl peroxide, tertiary butyl peroxyacetate, tertiary butyl perbenzoate, and mixtures thereof.

18. The method according to claim 11 , wherein the organometallic curing promoter is an organometallic compound selected from the group consisting of cobalt, nickel, manganese or iron naphthenate, cobalt neodecanoate, copper octoate, copper acetylacetonate, iron hexoate, and iron propionate.

19. The method according to claim 11 , wherein the thiourea accelerator is selected from the group consisting of ethylene thiourea, 1-acetyl-2-thiourea, 1-(2-pyridyl)-2-thiourea.

20. The method according to claim 11 , wherein the pyridinic reducing agent is 3,5-diethyl-1-phenyl-2-propyl-1,2-dihydropyridine (PDHP).

21. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , further comprising a copolymer selected from the group consisting of poly(methacrylate-acrylonitrile-butadiene-styrene) (MABS), poly(methacrylate-butadiene-styrene) (MBS), poly(acrylate-styrene-acrylonitrile) (ASA), poly(acrylonitrile-butadiene-styrene) (ABS), block copolymers of butadiene or isoprene with styrene, and mixtures and blends thereof.

22. The two part heat and moisture resistant acrylic adhesive composition of claim 21 , wherein the copolymer is present in an amount of less than 10% by weight of the two part heat and moisture resistant acrylic adhesive composition.

23. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the initiator part and the activator part are combined in a 1:1 ratio to form an adhesive.

24. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , wherein the initiator part and the activator part are combined to form an adhesive and less than 300 μg/L of the (meth)acrylate monomer is present in water when the adhesive is used in a migration test performed according to European Standard EN 12873-2:2004.

25. The two part heat and moisture resistant acrylic adhesive composition of claim 1 , further comprising an organic acid accelerator.

26. The two part heat and moisture resistant acrylic adhesive composition of claim 25 , wherein the organic acid accelerator is methacrylic acid.

Assignments (20)