Quinophthalone compound, mixed colorant, laser ray transmitting colored resin composition, and laser-welded product

Assignee: Orient Chemical Industries Co., Ltd.

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Quick Facts

Patent No.: US 7,879,929
App. No.: 11/571,916
Granted: Feb 1, 2011
Kind: B2

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Abstract

Quinophthalone compound of Formula (1) or (2), mixed colorant, laser ray transmitting colored resin composition containing thereof, and laser-welded product. in each of Formulas (1) and (2), X: —O-L; L: hydrogen atom, alkyl, aryl; Y represents hydrogen atom, hydroxyl, mercapto, alkoxy, aryloxy, heterocyclic oxy, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, alkylthio, arylthio, heterocyclic thio; R 1 to R 8 and R 1 to R 4 and R 9 to R 14 : hydrogen atom, nitro, hydroxyl, mercapto, carboxyl, cyano, thiocyano, halogen atom, alkyl, cycloalkyl, aryl, amino, acyl, alkoxy, aryloxy, heterocyclic oxy, acyloxy, alkylsulfonyloxy, arylsulfonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, alkoxycarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, heterocyclic oxycarbonyl, carbamoyl, sulfamoyl, alkylsulfonyl, arylsulfonyl, alkylthio, arylthio, heterocyclic thio, alkoxysulfonyl, cycloalkyloxysulfonyl, aryloxysulfonyl, heterocyclic oxysulfonyl; at least one of R 5 to R 8 in Formula (1) is carboxyl, at least one of R 9 to R 14 in Formula (2) is carboxyl.

Claims (77)

1. Laser-welded product wherein a laser ray transmitting member made of a laser ray transmitting colored resin composition which contains a thermoplastic resin or a thermoplastic elastomer and a quinophthalone compound represented by Formula (1) or (2) below and a laser ray absorbing member made of a resin composition having a thermoplastic resin or a thermoplastic elastomer, and having a laser ray absorbing layer, have been welded by laser welding with laser ray that has penetrated said laser ray transmitting member:

in each of Formulas (1) and (2),

each of R 1 to R 8 in Formula (1) and R 1 to R 4 and R 9 to R 14 in Formula (2) independently represents a hydrogen atom, a nitro group, a mercapto group, a carboxyl group, a cyano group, a thiocyano group, a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an amino group, an acyl group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an acyloxy group, an alkylsulfonyloxy group, an arylsulfonyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an alkoxycarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, a heterocyclic oxycarbonyl group, a carbamoyl group, a sulfamoyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkylthio group, an arylthio group, a heterocyclic thio group, an alkoxysulfonyl group, a cycloalkyloxysulfonyl group, an aryloxysulfonyl group, or a heterocyclic oxysulfonyl group;

at least one of R 5 to R 8 in Formula (1) is a carboxyl group, and at least one of R 9 to R 14 in Formula (2) is a carboxyl group.

2. Laser-welded product of claim 1 , wherein said quinophthalone compound has an endothermic peak at a temperature of not lower than 380° C.

3. Laser-welded product of claim 1 , wherein said laser ray transmitting colored resin composition contains said quinophthalone compound as a coloring ingredient, and another coloring ingredient.

4. Laser-welded product of claim 3 , wherein said laser ray transmitting colored resin composition has a black color.

5. Laser-welded product of claim 3 , wherein said other coloring ingredient is one or two or more selected from the group consisting of azo dyes/pigments, azo metal complex dyes/pigments, naphtholazo dyes/pigments, azo lake dyes/pigments, azomethine dyes/pigments, anthraquinone dyes/pigments, quinacridone dyes/pigments, dioxazine dyes/pigments, diketopyrrolopyrrole dyes/pigments, anthrapyridone dyes/pigments, isoindolinone dyes/pigments, indanthrone dyes/pigments, perinone dyes/pigments, perylene dyes/pigments, indigo dyes/pigments, thioindigo dyes/pigments, quinoline dyes/pigments, benzimidazolone dyes/pigments, and triphenylmethane dyes/pigments.

6. Laser-welded product of claim 3 , wherein said other coloring ingredient is one or two or more selected from the group consisting of, near-infrared ray transmitting, azo dyes, triphenylmethane dyes, anthraquinone dyes, perinone dyes, and anthrapyridone dyes.

7. Laser-welded product of claim 6 , wherein said other coloring ingredient is a salt forming dye prepared by allowing an acid dye to form a salt with an organic amine.

8. Laser-welded product of claim 1 , wherein the thermoplastic resin in said laser ray transmitting colored resin composition is a polyamide resin, a polyester resin, or a polyphenylene sulfide resin.

9. Laser-welded product of claim 1 , wherein said laser ray transmitting colored resin composition is obtained by mixing a thermoplastic resin or a thermoplastic elastomer and a master batch containing said quinophthalone compound in a thermoplastic resin or a thermoplastic elastomer.

10. Laser-welded product of claim 3 , wherein said laser ray transmitting colored resin composition is obtained by mixing a thermoplastic resin or a thermoplastic elastomer and a master batch containing said quinophthalone compound and said other coloring ingredient in a thermoplastic resin or a thermoplastic elastomer.

11. Laser-welded product of claim 9 , wherein the thermoplastic resin in said laser ray transmitting colored resin composition and said master batch is a polyamide resin, a polyester resin, or a polyphenylene sulfide resin.

12. The laser-welded product of claim 1 , wherein:

each of R 1 to R 8 in Formula (1) and R 1 to R 4 and R 9 to R 14 in Formula (2) independently represents a hydrogen atom, a carboxyl group, a chlorine atom, a fluorine atom, an iodine atom, carbamoyl group or sulfamoyl group;

at least one of R 5 to R 8 in Formula (1) is a carboxyl group, and at least one of R 9 to R 14 in Formula (2) is a carboxyl group.

13. The laser-welded product of claim 2 , wherein:

at least one of R 5 to R 8 in Formula (1) is a carboxyl group, and at least one of R 9 to R 14 in Formula (2) is a carboxyl group.

14. The laser-welded product of claim 7 , wherein:

at least one of R 5 to R 8 in Formula (1) is a carboxyl group, and at least one of R 9 to R 14 in Formula (2) is a carboxyl group.

15. The laser-welded product of claim 8 , wherein each of R 1 to R 8 in Formula (1) and R 1 to R 4 and R 9 to R 14 in Formula (2) independently represents a hydrogen atom, a carboxyl group, a chlorine atom, a fluorine atom, an iodine atom, carbamoyl group or sulfamoyl group;

at least one of R 5 to R 8 in Formula (1) is a carboxyl group, and at least one of R 9 to R 14 in Formula (2) is a carboxyl group.

16. The laser-welded product of claim 1 , wherein:

each of R 1 to R 4 , R 5 and R 8 in Formula (1) and R 1 to R 4 and R 9 , R 10 , R 13 and R 14 in Formula (2) represents a hydrogen atom;

each of R 6 and R 7 in Formula (1) and R 11 and R 12 in Formula (2) independently represents a hydrogen atom or a carboxyl group;

at least one of R 6 and R 7 in Formula (1) is a carboxyl group, and at least one of R 11 and R 12 in Formula (2) is a carboxyl group.

17. The laser-welded product of claim 2 , wherein:

each of R 1 to R 4 , R 5 and R 8 in Formula (1) and R 1 to R 4 and R 9 , R 10 , R 13 and R 14 in Formula (2) represents a hydrogen atom;

each of R 6 and R 7 in Formula (1) and R 11 and R 12 in Formula (2) independently represents a hydrogen atom or a carboxyl group;

at least one of R 6 and R 7 in Formula (1) is a carboxyl group, and at least one of R 11 and R 12 in Formula (2) is a carboxyl group.

18. The laser-welded product of claim 7 , wherein:

each of R 1 to R 4 , R 5 and R 8 in Formula (1) and R 1 to R 4 and R 9 , R 10 , R 13 and R 14 in Formula (2) represents a hydrogen atom;

each of R 6 and R 7 in Formula (1) and R 11 and R 12 in Formula (2) independently represents a hydrogen atom or a carboxyl group;

at least one of R 6 and R 7 in Formula (1) is a carboxyl group, and at least one of R 11 and R 12 in Formula (2) is a carboxyl group.

19. The laser-welded product of claim 8 , wherein:

each of R 1 to R 4 , R 5 and R 8 in Formula (1) and R 1 to R 4 and R 9 , R 10 , R 13 and R 14 in Formula (2) represents a hydrogen atom;

each of R 6 and R 7 in Formula (1) and R 11 and R 12 in Formula (2) independently represents a hydrogen atom or a carboxyl group;

at least one of R 6 and R 7 in Formula (1) is a carboxyl group, and at least one of R 11 and R 12 in Formula (2) is a carboxyl group.

20. The laser-welded product of claim 1 , wherein: