(Meth)acrylates of oxyalkylated phenolic resins and their use as adhesion promoters

• US 20030125493A1
• Filed: 10/26/2001
• Published: 07/03/2003
• Est. Priority Date: 10/26/2001
• Status: Abandoned Application

• Current Assignee: ARCO Chemical Technology, L.P. (Lyondellbasell Industries NV)
• Original Assignee: ARCO Chemical Technology, L.P. (Lyondellbasell Industries NV)
• Inventors: Rodriguez, Carmen L., Harris, Stephen H.
• Application Number:
  US10/044,167
• Publication Number:
  US 20030125493A1
• Time in Patent Office: Days
• US Class Current: 526/319
• CPC Class Codes: C08F 20/30 containing aromatic rings in the alcohol moiety

Abstract

(Meth)acrylate esters of oxyalkylated aralkylated, multi-ring phenolic hydroxyl-containing compounds may be prepared with relatively low viscosity, and are effective as coating composition additives, in particular as adhesion promoters.

Claims

1. An (meth)acrylate-functional composition comprising an (meth)acrylate ester of an oxyalkylated, aralkylated multi-ring phenolic polyol prepared by the process of:

a) selecting a multi-ring aralkylated phenolic starter having minimally two phenolic hydroxyl groups and at least three aryl ring systems which are not condensed with each other;

b) oxyalkylating said aralkylated phenolic starter with from 0.5 to 10 mol of oxyalkylating agent per equivalent of phenolic hydroxyl groups to produce an oxyalkylated aralkylated phenolic intermediate;

c) esterifying said oxyalkylated aralkylated phenolic intermediate with an alkacrylic acid or esterifyable derivative thereof to produce said (meth)acrylate ester of said oxyalkylated alkarylated multi-ring phenolic polyol,

wherein said step of esterifying is conducted with sufficient alkacrylic acid or esterifyable derivative thereof such that 70 mol percent or more of total hydroxyl groups are esterified.

2. The composition of claim 1, wherein 80 mol percent or more of hydroxyl groups are esterified.

3. The composition of claim 1, wherein about 90 mol percent or more of hydroxyl groups are esterified.

4. The composition of claim 1, wherein said aralkylated multi-ring phenolic starter comprises a styrenated phenolic compound.

5. The composition of claim 1, wherein said aralkylated multi-ring phenolic starter has a phenolic hydroxyl functionality which averages between 2 and 10.

6. The composition of claim 1, wherein said aralkylated multi-ring phenolic starter has a phenolic hydroxyl functionality which averages between 2and 5.

7. The composition of claim 1, wherein at least one of said oxyalkylating agent(s) is selected from the group consisting of ethylene carbonate, propylene carbonate, ethylene oxide, propylene oxide, 1,2-butylene oxide, 2,3-butylene oxide, and styrene oxide.

8. The composition of claim 1, wherein said oxyalkylating agent comprises propylene oxide.

9. The composition of claim 1 wherein said aralkylated multi-ring phenolic polyol comprises formaldehyde-coupled aralkylated bisphenol A.

10. The composition of claim 1, wherein said alkacrylic acid comprises acrylic acid.

14. An addition-curable composition comprising at least one (meth)acrylate-functional composition of claim 1 and a catalyst which promotes the addition polymerization of ethylenically-unsaturated compounds.

15. The addition-curable composition of claim 14, wherein said catalyst comprises a photoinitiator.

16. The composition of claim 14, wherein said composition further comprises a (meth)acrylate-functional monomer other than said (meth)acrylate-functional composition.

17. The composition of claim 14, further comprising at least one (meth)acrylate selected from the group consisting of the (meth)acrylates of C_2-10 aliphatic glycols, trimethylolpropane tri(meth)acrylate, and glycerine tri(meth)acrylate.

18. A process for increasing the adhesion and/or hardness of a cured, addition-curable composition derived from (meth)acrylate-functional components, said process comprising adding at least one (meth)acrylate-functional composition of claim 1 to said addition-curable composition prior to cure.

19. The process of claim 18, wherein one of said (meth)acrylate-functional components is replaced all or in part by said (meth)acrylate-functional composition.

20. The process of claim 18, wherein one of said (meth)acrylate-functional components comprises a (meth)acrylate-functional epoxy resin.

11. A low viscosity acrylate-functional compound,

said compound comprising an acrylate ester of an oxyalkylated multi-ring aralkylated phenol having at least three non-condensed aromatic rings, at least one of said non-condensed aromatic rings comprising a phenolic hydroxyl-group free aryl group linked to a phenolic hydroxyl-group-containing aryl group through an alkylene bridge, said alkylene bridge optionally interrupted by one or more of an aryl group, O, and N;

said multiring aralkylated phenol having, prior to oxyalkylation to form said oxyalkylated multi-ring aralkylated phenol, from

2 to 10 phenolic hydroxyl groups;

said oxyakylation sufficient to provide, on average, from 2 to 25 mol of oxyalkylene groups per mol of phenolic hydroxyl groups;

said oxyalkylated multi-ring aralkylated phenol having less than 20 mol percent free phenolic hydroxyl groups based on the total mol of phenolic groups initially present in said multi-ring aralkylated phenol; and

said acrylate-functional compound being a liquid with a neat viscosity less than 3000 cps at 25°

C.

12. The acrylate-functional compound of claim 11, wherein said multi-ring aralkylated phenol comprises a reaction product of a bisphenol, an optionally substituted styrene, and optionally, formaldehyde or an aryldiolefin.

13. The acrylate-functional compound of claim 12 which has an acrylate functionality of from 2 to 4, wherein said oxyalkylation is performed with propylene oxide to an average degree of oxyalkylation of from 3 to 15, and wherein the viscosity of said acrylate-functional is less than 1500 cps at 25°

C.