Method for preparing high solids films employing a plurality of curing mechanisms

• US 4,025,407 A
• Filed: 11/04/1974
• Issued: 05/24/1977
• Est. Priority Date: 05/05/1971
• Status: Expired due to Term

• Current Assignee: PPG Industries Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Incorporated (Nouryon BV)
• Inventors: Chang, Wen-Hsuan, Wismer, Marco
• Primary Examiner(s): Turer, Richard B.
• Application Number:
  US05/520,767
• Time in Patent Office: 932 Days
• Field of Search: 204/159.14, 204/159.15, 204/159.16, 204/159.17, 204/159.19, 260/859, 260/861
• US Class Current: 522/142
• CPC Class Codes: C08F 291/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
• CPC Class Codes: C08G 59/14 Polycondensates modified by chemical after-treatment
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 61/20 Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen with aminophenols C08L61/04
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 67/00 Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 67/06 Unsaturated polyesters
• CPC Class Codes: C08L 75/04 Polyurethanes
• 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 167/06 Unsaturated polyesters having carbon-to-carbon unsaturation
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: C09D 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
• CPC Class Codes: Y10T 428/31678 Of metal
• CPC Class Codes: Y10T 428/31681 Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.]
• CPC Class Codes: Y10T 428/31688 Next to aldehyde or ketone condensation product
• CPC Class Codes: Y10T 428/31692 Next to addition polymer from unsaturated monomers

Abstract

Conventional thermosetting resins are thinned with radiation sensitive or actinic light sensitive materials and then subjected to a dual cure wherein the material is first subjected to ionizing irradiation or actinic light and then to the conventional curing mechanism of the thermosetting resin. The resultant film contains the properties of both the radiation sensitive material and the conventional thermosetting resin and is easily applied as a coating.

Claims

1. A method for preparing high solids films comprising subjecting a film of a mixture comprising

a. a radiation sensitive liquid material;

and

b. a radiation insensitive thermosetting resin wherein said radiation sensitive liquid material is present in said mixture in an amount in the range of from about 20 to about 90 percent by weight and wherein said radiation insensitive thermosetting resin is present in said mixture in an amount in the range of from about 10 to about 80 percent by weight, to a member of either of the following two classes of crosslinking conditions;

c. a first class consisting of ionizing irradiation and actinic light, or

d. a second class consisting of oxidation, moisture and heating to partially cure said mixture and subsequently completely curing the remainder of said mixture by subjecting said partially cured mixture to a member of the other of said classes of curing conditions to form a film which is flexible and abrasion resistant.

2. The method of claim 1 wherein

a. said radiation sensitive liquid material is selected from the group consisting of ethylenically unsaturated polyester resins solubilized in vinyl monomers, esters of acrylic acid, esters of methacrylic acid, amides of acrylic acid, amides of methacrylic acid, diacrylates, dimethacrylates, triacrylates and trimethacrylates;

b. said radiation insensitive thermosetting resin is selected from the group consisting of radiation insensitive thermosetting alkyd resins, radiation insensitive thermosetting polyurethane resins, radiation insensitive thermosetting acrylic resins, radiation insensitive thermosetting polyepoxide resins, radiation insensitive thermosetting aminoplast resins and radiation insensitive thermosetting phenolic resins; and

c. said first class consists of electron radiation having an energy of at least about 100,000 electron volts and ultraviolet light having a wavelength in the range of from about 180 to about 400 nanometers.

3. The method of claim 1 wherein

a. said radiation sensitive liquid material is selected from the group consisting of ethylenically unsaturated polyester resins solubilized in vinyl monomers, esters of acrylic acid, esters of methacrylic acid, amides of acrylic acid, amides of methacrylic acid, diacrylates, dimethacrylates, triacrylates and trimethacrylates;

b. said radiation insensitive thermosetting resin is selected from the group consisting of radiation insensitive thermosetting alkyd resins, radiation insensitive thermosetting polyurethane resins, radiation insensitive thermosetting acrylic resins and radiation insensitive thermosetting polyepoxide resins; and

c. said first class consists of electron radiation having an energy of at least about 100,000 electron volts and ultraviolet light having a wavelength in the range of from about 180 to about 400 nanometers.

4. The method of claim 1 wherein said mixture is subjected to said first class of crosslinking conditions to partially cure said mixture and then said partially cured mixture is subjected to said second class of crosslinking conditions to form a film which is flexible and abrasion resistant.

5. The method of claim 1 wherein said mixture is subjected to said second class of crosslinking conditions to partially cure said mixture and then said partially cured mixture is subjected to said first class of crosslinking conditions to form a film which is flexible and abrasion resistant.

6. The method of claim 1 wherein said radiation insensitive thermosetting resin is a radiation insensitive thermosetting polyurethane resin.

7. The method of claim 6 wherein said second class of curing conditions is moisture.

8. The method of claim 1 wherein said radiation insensitive thermosetting resin is a radiation insensitive thermosetting alkyd resin.

9. The method of claim 8 wherein said second class of curing conditions is oxidation.

10. The method of claim 1 wherein said radiation insensitive thermosetting resin is a radiation insensitive thermosetting acrylic resin comprising an interpolymer of an unsaturated carboxylic acid amide and at least one other monomer having a CH₂ = C<

group, said interpolymer being characterized by having amido hydrogen atoms replaced by the structure --RCHOR₁, wherein R is selected from the group consisting of hydrogen and saturated lower aliphatic hydrocarbon radicals and R₁ is selected from the group consisting of hydrogen and lower alkyl radicals.

11. The method of claim 10 wherein said second class of crosslinking conditions is heating.

12. The method of claim 1 wherein said radiation insensitive thermosetting resin is a radiation insensitive thermosetting polyepoxide resin.

13. The method of claim 12 wherein said second class of crosslinking conditions is oxidation.

14. The method of claim 1 wherein said mixture is subjected to a total dose of ionizing irradiation of from 0.2 to about 20 megarads.

15. A method for preparing high solids films comprising subjecting a film of a mixture comprising

a. radiation sensitive liquid esters of acrylic acid;

and

b. radiation insensitive thermosetting polyurethane resin wherein said radiation sensitive liquid esters of acrylic acid are present in said mixture in an amount in the range of from about 20 to about 90 percent by weight and wherein said radiation insensitive thermosetting polyurethane resin is present in said mixture in an amount in the range of from about 10 to about 80 percent by weight, to a member of either of the following two classes of crosslinking conditions.

c. a first class consisting of ionizing irradiation and actinic light, or

d. a second class consisting of oxidation, moisture and heating to partially cure said mixture and subsequently completely curing the remainder of said mixture by subjecting said partially cured mixture to a member of the other of said classes of curing conditions to form a film which is flexible and abrasion resistant.