Resorcinol Resin-Blocked Isocyanates and Their Applications

Abstract

Resorcinol resin-blocked isocyanate compositions are derived from the reaction between a resorcinol resin and at least two different isocyanate compounds. The resorcinol resin-blocked isocyanate compositions may have two or more unblocking temperatures and/or melting characteristics that may provide some unique properties, such as improved adhesion of reinforcing materials to rubber compounds. The resorcinol resin-blocked isocyanate compositions can be used in fabric dipping formulations and/or rubber compositions with improved properties.

Description

BRIEF DESCRIPTION OF THE FIGURE

FIG. 1 depicts the process flow diagram showing the process steps of preparing a resorcinol resin-blocked isocyanate composition derived from resorcinol, formaldehyde and a mixture of 2,4′- and 4,4′-MDI.

FIG. 2 depicts the chemical reaction steps of preparing a resorcinol resin-blocked isocyanate composition derived from resorcinol, formaldehyde and a mixture of 2,4′- and 4,4′-MDI.

Claims

1) A resorcinol resin-blocked isocyanate composition comprising: (a) a first compound having Formula (VI′):

2) The resorcinol resin-blocked isocyanate composition of claim 1, wherein each of X and Y is independently a divalent radical having one of the following formulae:

3) The resorcinol resin-blocked isocyanate composition of claim 1 further comprising a third compound having Formula (VIII′):

4) A resorcinol resin-blocked isocyanate composition obtainable from the reaction between at least two different isocyanate compounds and a resorcinol resin.

5) The resorcinol resin-blocked isocyanate composition of claim 4, wherein the resorcinol resin has Formula (V), Formula (V′) or a combination thereof:

6) The resorcinol resin-blocked isocyanate composition of claim 5, wherein each of A, B, A′ and B′ is independently H, Formula (V-1) or Formula (V-2):

7) The resorcinol resin-blocked isocyanate composition of claim 4, wherein the at least two isocyanate compounds have the formulae O═C═N—X—N═C═O and O═C═N—Y—N═C═O wherein X and Y are different and each of X and Y comprises independently alkylene, cycloalkylene, arylene, alkarylene, cycloalkarylene, aralkylene, heterocyclylene, heteroarylene or a combination thereof.

8) A process for preparing a resorcinol resin-blocked isocyanate composition comprising reacting at least two different isocyanate compounds with a resorcinol resin.

9) The process of claim 8, wherein the resorcinol resin has Formula (V), Formula (V′) or a combination thereof:

10) The process of claim 9, wherein each of A, B, A′ and B′ is independently H, Formula (V-1), or Formula (V-2):

11) The process of claim 8, wherein the reaction occurs in the absence of a solvent.

12) The process of claim 8, wherein the reaction occurs in the presence of a catalyst.

13) The process of claim 12, wherein the catalyst is 3-methyl-1-phenyl-2-phospholene-1-oxide or dibutyltin dilaurate.

14) The process of claim 8, wherein the reaction occurs in the absence of a catalyst.

15) The process of claim 8, wherein the at least two isocyanate compounds have the formulae O═C═N—X—N═C═O and O═C═N—Y—N═C═O wherein X and Y are different and each of X and Y comprises independently alkylene, cycloalkylene, arylene, alkarylene, cycloalkarylene, aralkylene, heterocyclylene, heteroarylene or a combination thereof.

16) The process of claim 15, wherein each of X and Y is independently a divalent radical having one of the following formulae:

17) A vulcanizable rubber composition comprising or obtainable from a mixture comprising a rubber material, a methylene donor and a methylene acceptor comprising the resorcinol resin-blocked isocyanate composition of claim 1.

18) The vulcanizable rubber composition of claim 17, wherein the rubber material is a natural or synthetic rubber.

19) The vulcanizable rubber composition of claim 17 further comprising a rubber reinforcement material.

20) The vulcanizable rubber composition of claim 19, wherein the rubber reinforcement material is in the form of fibers, filaments, fabrics or cords.

21) The vulcanizable rubber composition of claim 19, wherein the rubber reinforcing material is made of a polyester, a polyamide, carbon, glass, steel, polybenzoxazole or rayon.

22) The vulcanizable rubber composition of claim 21, wherein the reinforcing material is steel.

23) The vulcanizable rubber composition of claim 17 further comprising a vulcanizing agent.

24) The vulcanizable rubber composition of claim 17 further comprising at least an additive, wherein the additive is carbon black, zinc oxide, silica, an antioxidant, a stearate, an accelerator, an adhesion promoter, a cobalt salt, stearic acid, a filler, a plasticizer, a wax, a processing oil, a retarder, an antiozonant or a combination thereof.

25) A dipping formulation comprising the resorcinol resin-blocked isocyanate composition of claim 1.

26) The dipping formulation of claim 25 further comprising a solvent.

27) The dipping formulation of claim 25 further comprising an additive.

28) The dipping formulation of claim 27, wherein the additive is an epoxy-containing compound, a thickener, an antifoam or a combination thereof.

29) The dipping formulation of claim 25 further comprising a poly(vinyl pyridine/butadiene/styrene) latex.

30) The dipping formulation of claim 25 further comprising a resin solution.

31) The dipping formulation of claim 30, wherein the resin solution is a resorcinol-formaldehyde solution.

32) The dipping formulation of claim 31 further comprising an additive.

33) The dipping formulation of claim 32, wherein the additive is an antifoam.

34) A fabricated article comprising a rubber material and a rubber reinforcing material treated with the dipping formulation of claim 25.

35) The fabricated article of claim 34, wherein the rubber material is a natural or synthetic rubber.

36) The fabricated article of claim 34, wherein the rubber reinforcing material is in the form of fibers, filaments, fabrics or cords.

37) The fabricated article of claim 34, wherein the rubber reinforcing material is made of a polyester, a polyamide, carbon, glass, steel, a polybenzoxazole or rayon.

38) The fabricated article of claim 34, wherein the fabricated article is a tire, power transmission belt, conveyor belt, V-belt, hose printing roll, rubber shoe heel, rubber shoe sole, automobile floor mat, truck mud flap or ball mill liner.

39) A coating comprising a resin prepared by curing Formula (B), (B′), (C) or a combination thereof:

40) The coating of claim 39, wherein the curing occurs in the presence of an initiator.

41) The coating of claim 40 further comprising an additive.

42) The coating of claim 41, wherein the additive is a filler, rheology modifier, thickener, surfactant, wetting agent, cross-linking agent, coupling agent, colorant, lubricant, leveling agent, antioxidant, UV stabilizer, plasticizer or a combination thereof.

43) A coating comprising a resin prepared by curing Formula (B), (D) or a combination thereof:

44) The coating of claim 43 further comprising an additive.

45) The coating of claim 44, wherein the additive is a filler, rheology modifier, thickener, surfactant, wetting agent, cross-linking agent, coupling agent, colorant, lubricant, leveling agent, antioxidant, UV stabilizer, plasticizer or a combination thereof.