Fluorescent degree of cure monitors

• US 5,118,559 A
• Filed: 06/03/1991
• Issued: 06/02/1992
• Est. Priority Date: 05/31/1989
• Status: Expired due to Fees

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: DeVoe, Robert J., Tiers, George V. D., Brown-Wensley, Katherine A.
• Primary Examiner(s): McCamish, Marion E.
• Assistant Examiner(s): BERMAN, SUSAN W
• Application Number:
  US07/709,719
• Time in Patent Office: 365 Days
• Field of Search: 522/99, 522/100, 522/103, 522/182, 522/65, 522/70, 526/93, 526/103, 526/284, 526/280, 526/256, 526/259, 526/268, 526/279, 528/15, 528/25, 528/27, 528/28, 428/262, 428/264, 428/266, 428/290
• US Class Current: 442/59
• CPC Class Codes: C08F 283/12 on to polysiloxanes
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 85/00 General processes for preparing compounds provided for in this subclass
• CPC Class Codes: C08J 3/20 Compounding polymers with additives, e.g. colouring
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: G01N 21/643 non-biological material
• CPC Class Codes: G03F 7/105 having substances, e.g. indicators, for forming visible images
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane
• CPC Class Codes: Y10T 428/31855 Of addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31895 Paper or wood
• CPC Class Codes: Y10T 428/31909 Next to second addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31913 Monoolefin polymer
• CPC Class Codes: Y10T 442/20 Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer

Abstract

A curable composition, the cure of which can be monitored optically, comprises at least one of a hydride curable silicone, an ethylenically unsaturated compound, and a cationically polymerizable monomer, and as cure monitor dibenzofulvene or derivatives thereof. The cure monitor is a latent fluorophore which reacts under the cure conditions to form a UV-detectable fluorophore.

The invention also provides a method for measuring degree of cure of a polymeric material which can be a coating or an article.

Claims

1. An article comprising a support and having applied to at least one surface thereof a curable composition consisting essentially of at least one of (a) a hydride curable silicone comprising an ethylenically unsaturated siloxane and a polyhydrosiloxane, (b) an ethylenically unsaturated compound selected from the group consisting of acrylates and methacrylates, unsaturated amides, and vinyl compounds, and (c) a cationically polymerizable monomer which is different from component (b) and is selected from the group consisting of 1,2-, 1,3-, and 1,4-cyclic ethers, vinyl ethers, N-vinyl compounds, ethylenically unsaturated hydrocarbons, cyclic formals an cyclic organosiloxanes;

and dibenzofulyene or derivative thereof as a latent uvaphore which is capable of reacting during curing to form a uvaphore, said dibenzofulvene or derivative thereof having the formula ##STR8## wherein X is CR¹ R² or NR¹, wherein R¹ and R² each independently is a hydrogen atom, or an alkyl, aryl, alkenyl, aralkenyl, alkynyl, aralkynyl, alkaryl, or aralkyl group, or R¹ and R² together are a cycloaliphatic group of ring size 3 to 12 atoms, all of which can include up to 50 carbon atoms and 0 to 30 heteroatoms selected from the group consisting of unitary N, Si, S and nonperoxidic O; and

wherein aromatic groups designated A and B together or each independently contain up to two ring nitrogen atoms, and together or independently are a single or fused aromatic ring system having 1 to 4 rings.

2. The article according to claim 1 wherein the aromatic groups designated A and B of formula I are substituted by 1 to 4 substituents chosen from (1) alkyl, aryl, aralkyl, alkaryl, acylamido, acyl, amino, alkoxycarbonyl, alkoxy, aryloxy, and hydroxycarbonyl groups of up to 50 carbon atoms and 0 to 30 unitary fluoro, chloro, bromo, nitrogen, silicon, sulfur, and nonperoxidic oxygen atoms, (2) cyano, chloro, bromo, fluoro groups, and (3) silyl and siloxy groups containing up to 200 silicon atoms and up to 200 unitary nitrogen, sulfur and nonperoxidic oxygen atoms.

3. The article according to claim 1 wherein said dibenzofulvene or derivative thereof of said curable composition is selected from the group consisting of dibenzofulvene, methyldibenzofulvene vinyldibenzofulvene.

4. The article according to claim 1 wherein said dibenzofulvene or derivative thereof of said curable composition is present int he range of 0.001 to 10 weight percent of the solids content of the curable composition.

5. The article according to claim 1 wherein said curable composition consists essentially of a hydride curable silicone comprising an ethylenically unsaturated siloxane and a polyhydrosiloxane.

6. The article according to claim 1 wherein said curable composition consists essentially of an ethylenically unsaturated compound selected form the group consisting of acrylates and methacrylates, unsaturated amides, and vinyl compounds.

7. The article according to claim 1 wherein said curable composition consists essentially of a cationically polymerizable monomer which is selected from the group consisting of 1,2-, 1,3-, and 1,4-cyclic ethers, vinyl ethers, N-vinyl compounds, ethylenically unsaturated hydrocarbons, cyclic formals, and cyclic organosiloxanes.

8. The article according to claim 1 wherein said curable composition further consists of an effective amount of a thermally or photochemically activated catalyst.

9. The article according to claim 1 wherein said curable composition further consists of an inhibitor.

10. The article according to claim 1 wherein said curable composition further consists of at least one adjuvant selected from the group consisting of fillers, plasticizers, flowing agents, colorants, and pigments.

11. The article according to claim 1 wherein said support is a woven or nonwoven web.

12. The article according to claim 1 wherein said support is a solid material.

13. The article according to claim 1 which has been cured.

14. The article according to claim 13 wherein said support is a woven or nonwoven web.

15. The article according to claim 13 wherein said support is a solid material.

16. The article according to claim 13 wherein said uvaphore has the formula ##STR9## wherein X is as previously defined, and Y and Z are chain atoms in the backbone of said cured composition.