Dual curable composition

• US 10,563,011 B2
• Filed: 03/14/2014
• Issued: 02/18/2020
• Est. Priority Date: 03/15/2013
• Status: Active Grant

• Current Assignee: Benedict S. Curatolo
• Original Assignee: Benedict S. Curatolo
• Inventors: Curatolo, Benedict S.
• Primary Examiner(s): Moore, Margaret G
• Application Number:
  US14/210,851
• Publication Number:
  US 20140272175A1
• Time in Patent Office: 2,167 Days
• CPC Class Codes: C07F 7/081 comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
• CPC Class Codes: C08F 220/343 in the form of urethane links
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08F 230/085 the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
• CPC Class Codes: C08G 2150/90 Compositions for anticorrosive coatings
• CPC Class Codes: C08G 59/00 Polycondensates containing more than one epoxy group per molecule low-molecular-weight polyepoxy compounds C07; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
• CPC Class Codes: C08G 63/00 Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule polyester-amides C08G69/44; polyester-imides C08G73/16
• CPC Class Codes: C08G 63/695 containing silicon
• CPC Class Codes: C08G 63/6952 derived from hydroxycarboxylic acids
• CPC Class Codes: C08G 63/78 Preparation processes
• CPC Class Codes: C08G 77/54 Nitrogen-containing linkages C08G77/485 takes precedence
• CPC Class Codes: C08K 2003/2241 Titanium dioxide
• CPC Class Codes: C08K 2003/321 Phosphates
• CPC Class Codes: C08K 2201/019 the composition being defined by the absence of a certain additive
• CPC Class Codes: C08K 3/22 of metals
• CPC Class Codes: C08K 3/32 Phosphorus-containing compounds
• CPC Class Codes: C08K 3/36 Silica
• CPC Class Codes: C08K 5/375 containing six-membered aromatic rings C08K5/3725 takes precedence
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 167/00 : Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain based on polyester-amides C09D177/12; based on polyester-imides C09D179/08; Coating compositions based on derivatives of such polymers
• CPC Class Codes: C09D 183/14 : in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C09D183/10 takes precedence
• CPC Class Codes: C09D 4/00 : Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
• CPC Class Codes: C09D 5/08 : Anti-corrosive paints
• CPC Class Codes: C09J 163/00 : Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
• CPC Class Codes: C09J 167/00 : Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain based on polyester-amides C09J177/12; based on polyester-imides C09J179/08; Adhesives based on derivatives of such polymers
• CPC Class Codes: C09J 183/14 : in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms C09J183/10 takes precedence
• CPC Class Codes: C09J 2301/414 : presence of a copolymer

Abstract

A dual curable composition is provided, comprising a compound represented by formula (I):
(acrylate)_a-(A)-(silane)_b  (I)
in which a and b are identical or different and are each represented by an integer greater than or equal to 1; and wherein the dual curable composition is radiation curable and/or moisture curable. The moiety A comprises at least one of an aliphatic hydrocarbon, a cycloaliphatic hydrocarbon, an aryl moiety, an ether, an ester, an amide, a urethane, a urea, a hydroxyl group-containing organic moiety, an acrylic oligomer, an epoxy oligomer, a urethane oligomer, a polyester oligomer, or mixtures thereof, and the dual curable composition has a molecular weight greater than or equal to 300.

Claims

1. A cured composition, that has been cured by radiation cure and moisture cure of a dual curable composition, the dual curable composition comprising a compound represented by formula (I):

(acrylate)_a-(A)-(silane)_b 

 

(I)

in which a and b are identical or different and are each represented by an integer greater than or equal to 1; and

the moiety A comprises at least one of a urethane, a urea, an acrylic oligomer, a urethane oligomer, or mixtures thereof;

wherein the dual curable composition compound represented by formula (I) is further represented by formula (II) and/or formula (III);

2. The cured composition of claim 1, wherein the moiety B of the dual curable composition comprising a compound represented by formula (II) and/or formula (III) comprises a neohexyl group.

3. The cured composition of claim 1, wherein the dual curable composition comprising a compound represented by formula (II) and/or formula (III) further comprises an additional component of a curable composition.

4. The cured composition of claim 1, wherein the dual curable composition comprising a compound represented by formula (II) and/or formula (III) further comprises a silane.

5. The cured composition of claim 1, wherein the dual curable composition comprising a compound represented by formula (II) and/or formula (III) further comprises a reactive monomer.

6. The cured composition of claim 1, wherein the dual curable composition comprising a compound represented by formula (II) and/or formula (III) further comprises an acrylate.

7. The cured composition of claim 1, wherein the dual curable composition comprising a compound represented by formula (II) and/or formula (III) further comprises an oligomer.

8. The cured composition of claim 1, wherein the dual curable composition comprising a compound represented by formula (II) and/or formula (III) further comprises a photoinitiator.

9. The cured composition of claim 1, wherein the dual curable composition comprising a compound represented by formula (II) and/or formula (III) further comprises a cationic photoinitiator.

10. The cured composition of claim 1, wherein the dual curable composition comprising a compound represented by formula (II) and/or formula (III) further comprises at least one of a dispersant, pigment, filler, flow agent, leveling agent, wetting agent, surfactant, defoamer, rheology modifier, stabilizer, antioxidant, adhesion promoter, corrosion inhibitor, or mixtures thereof.

11. A coating, sealant, adhesive, or composite resin comprising the cured composition of claim 1.

12. A coating, sealant, adhesive, or composite resin comprising the cured composition of claim 2.

13. The cured composition of claim 1, that has been cured by radiation cure and moisture cure of a dual curable two part coating, sealant, adhesive, or composite resin comprising Part A and Part B;

Part A comprising;

the dual curable composition comprising a compound represented by formula (II) and/or formula (III); and

Part B comprising at least one of;

a corrosion inhibitor,

an organic acid functional component,

or mixtures thereof.

14. The cured composition of claim 13, that has been cured by radiation cure and moisture cure of the dual curable two part coating, sealant, adhesive, or composite resin;

Part A further comprising at least one of;

a photoinitiator, reactive monomer, defoamer, dispersant, pigment, stabilizer, or mixtures thereof and

Part B further comprising at least one of;

a dispersant, reactive monomer, defoamer, oligomer, adhesion promoter, surfactant, flow agent, or mixtures thereof.

15. A method of preparing the composition of claim 1, the method comprising:

reacting an acrylated component comprising at least two acrylate groups with an aminosilane to form a reaction product comprising at least one acrylate group and at least one silane group to form a compound represented by formula (II) and/or formula (III);

optionally, further comprising contacting an additional component of a curable composition with the reaction product;

and exposing the reaction product to a radiation source and moisture to cure the reaction product.

16. The method according to claim 15, wherein the acrylated component comprises at least one of a diacrylate monomer, aliphatic polyether urethane diacrylate, aliphatic polyester urethane diacrylate, aromatic polyether urethane diacrylate, aromatic polyester urethane diacrylate, acrylated acrylic diacrylate, polyacrylate monomer, aliphatic polyether urethane polyacrylate, aliphatic polyester urethane polyacrylate, aromatic polyether urethane polyacrylate, aromatic polyester urethane polyacrylate, acrylated acrylic polyacrylate, acrylate grafted polymer, or mixtures thereof.

17. The method according to claim 15, wherein the aminosilane comprises at least one of 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-beta-(aminoethyl)-3-aminopropyltrimethoxysilane, N-beta-(aminoethyl)-3-aminopropyl methyldimethoxysilane, N-beta-(aminoethyl)-3-aminopropyltriethoxysilane, delta-aminoneohexyltrimethoxysilane, delta-aminoneohexylmethyldimethoxysilane, delta-aminoneohexyl triethoxysilane, or mixtures thereof.

18. A method of coating a substrate with the cured composition of claim 1 comprising applying to the substrate the dual curable composition comprising a compound represented by formula (II) and/or formula (III), and exposing the coated substrate to a radiation source and moisture to cure the dual curable composition, wherein the radiation source is at least one of ultraviolet radiation or electron beam radiation.

19. A method of coating a substrate with the cured composition of claim 2 comprising applying to the substrate the dual curable composition comprising a compound represented by formula (II) and/or formula (III), wherein the moiety B comprises a neohexyl group, and exposing the coated substrate to a radiation source and moisture to cure the dual curable composition, wherein the radiation source is at least one of ultraviolet radiation or electron beam radiation.

20. A method of coating a substrate with the cured composition of claim 13, comprising:

a) Providing Part A and Part B;

b) Mixing Part A and Part B to form a mixture;

c) Applying the mixture to the substrate; and

d) Exposing the coated substrate to a radiation source and moisture to cure the mixture.

21. A method of coating a substrate with the cured composition of claim 14, comprising:

a) Providing Part A and Part B;

b) Mixing Part A and Part B to form a mixture;

c) Applying the mixture to the substrate; and

d) Exposing the coated substrate to a radiation source and moisture to cure the mixture.

22. The method of claim 18, wherein the substrate is selected from the group consisting of metal, concrete, stone, vinyl, wood, tile, ceramic, glass, plastic, paper, cardboard, asphalt, thermoplastic materials, thermoset materials, rubber, and composite materials.

23. The method of claim 18, wherein the substrate comprises a metal.

24. The method of claim 23, wherein the metal comprises aluminum, aluminum alloy, steel, stainless steel, magnesium alloy, or titanium.

25. The method of claim 18, wherein the substrate comprises an industrial or aerospace substrate.

26. A corrosion-resistant coating, sealant, adhesive, or composite resin comprising the cured composition of claim 1.

27. A solvent-free, isocyanate-free, chromium-free coating, sealant, adhesive, or composite resin comprising the cured composition of claim 1.

28. The cured composition of claim 2, that has been cured by radiation cure and moisture cure of a dual curable two part coating, sealant, adhesive, or composite resin comprising Part A and Part B;

Part A comprising;

the dual curable composition comprising a compound represented by formula (II) and/or formula (III), wherein the moiety B comprises a neohexyl group; and

Part B comprising at least one of;

a corrosion inhibitor,

an organic acid functional component,

or mixtures thereof.

29. The cured composition of claim 28, that has been cured by radiation cure and moisture cure of the dual curable two part coating, sealant, adhesive, or composite resin;

Part A further comprising at least one of;

a photoinitiator, reactive monomer, defoamer, dispersant, pigment, stabilizer, or mixtures thereof; and

Part B further comprising at least one of;

a dispersant, reactive monomer, defoamer, oligomer, adhesion promoter, surfactant, flow agent, or mixtures thereof.

30. A method of coating a substrate with the cured composition of claim 28, comprising:

a) Providing Part A and Part B;

b) Mixing Part A and Part B to form a mixture;

c) Applying the mixture to the substrate; and

d) Exposing the coated substrate to a radiation source and moisture to cure the mixture.

31. A method of coating a substrate with the cured composition of claim 29, comprising:

a) Providing Part A and Part B;

b) Mixing Part A and Part B to form a mixture;

c) Applying the mixture to the substrate; and

d) Exposing the coated substrate to a radiation source and moisture to cure the mixture.

32. A corrosion-resistant coating, sealant, adhesive, or composite resin comprising the curable composition of claim 2.

33. A solvent-free, isocyanate-free, chromium-free coating, sealant, adhesive, or composite resin comprising the cured composition of claim 2.