Composite particle with a carbodiimide resin layer and a process for producing the same

• US 7,258,921 B2
• Filed: 08/07/2003
• Issued: 08/21/2007
• Est. Priority Date: 08/09/2002
• Status: Expired due to Fees

• Current Assignee: Nisshinbo Industries, Inc. (Kawasaki Heavy Industries Limited)
• Original Assignee: Nisshinbo Industries, Inc. (Kawasaki Heavy Industries Limited)
• Inventors: Yoshida, Hiroshi, Sato, Takaya, Hashiba, Toshifumi, Kudo, Satomi, Hayakawa, Kazutoshi, Satoh, Kaori
• Primary Examiner(s): KILIMAN, LESZEK B
• Application Number:
  US10/523,816
• Publication Number:
  US 20050271875A1
• Time in Patent Office: 1,475 Days
• Field of Search: 428/402, 428/403, 428/407, 427/384
• US Class Current: 428/402
• CPC Class Codes: C08G 73/00 Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00 polycarbodiimides prepared from isocyanates C08G18/025, C08G18/797
• CPC Class Codes: C08J 2379/00 Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
• CPC Class Codes: C08J 3/005 Processes for mixing polymers
• CPC Class Codes: C08J 3/12 Powdering or granulating
• CPC Class Codes: C08L 79/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
• CPC Class Codes: Y10T 428/2982 Particulate matter [e.g., sphere, flake, etc.]
• CPC Class Codes: Y10T 428/2991 Coated
• CPC Class Codes: Y10T 428/2998 including synthetic resin or polymer

Abstract

A composite particle that can be easily converted to cured particle or half cured particle by the use of carbodiimide resin without changing of the configuration of matrix particle of, for example a thermoplastic resin, excelling in mechanical and functional characteristics by virtue of the reaction capability inherently possessed by a carbodiimide group. In particular, a composite particle comprising matrix particle (A) having a functional group capable of reacting with a carbodiimide group and carbodiimide resin (B), characterized in that the functional group of the matrix particle (A) couples with the carbodiimide group of the carbodiimide resin (B) and that the composite particle is provided with an outer shell layer of carbodiimide resin (B) having an average thickness diameter (L), defined by the following formula [1], ranging from 0.01 to 20 μm: L=(L₂−L₁)/2 [1] wherein L1 represents the average diameter of matrix particle, and L2 represents the average diameter of composite particle.

Claims

1. A composite particle made from a base particle (A) and a carbodiimide resin (B), wherein

said base particle (A) has a functional group reactable with a carbodiimide group and said carbodiimide resin (B) contains a carbodiimide group and

said base particle (A) and said carbodiimide resin (B) are bonded together by the functional group of the base particle (A) and the carbodiimide group of the carbodiimide resin (B) to form a shell layer comprised of the carbodiimide resin (B) having average thickness diameter (L), represented by the following numerical equation [1], in the range of 0.01 to 20 μ

m;

L=(L₂−

L₁)/2 

 

[1]

wherein L₁ represents average particle diameter of the base particle and L₂ represents average particle diameter of the composite particle.

2. The composite particle according to claim 1, characterized in that morphology of the base particle (A) is true spherical or near spherical.

3. The composite particle according to claim 1, characterized in that at least one carbodiimide group in a molecular chain of the carbodiimide resin (B) bonds with the functional group of the base particle (A) to form the shell layer.

4. The composite particle according to claim 1, characterized in that the bond of the functional group of the base particle (A) and the carbodiimide group of the carbodiimide resin (B) is at least one kind selected from a carbamoyl amide bond, an isourea bond, a guanidine bond or a thiourea bond.

5. The composite particle according to claim 1, characterized in that the functional group of the base particle (A) is at least one active hydrogen group selected from a hydroxyl group, a carboxyl group, an amino group or a thiol group.

6. The composite particle according to claim 1, characterized in that the base particle (A) is a thermoplastic resin particle.

7. The composite particle according to claim 1, characterized in that the carbodiimide resin (B) is a carbodiimide resin represented by the following chemical formula (1):

R¹—

Y—

(R²—

N═

C═

N)_n—

R²—

Y—

R³ 

 

(1)

wherein R¹ and R³ represent hydrogen or an organic residue having a carbon number of 1 to 40, which is obtained from a compound having a functional group reactable with an isocyanate group left by the functional group, and may be the same or different, and R² represents an organic residue which is a diisocyanate left by the isocyanate group, wherein said diisocyanate may be a different type;

Y represents a bond formed by the isocyanate group and the functional group reactable with the isocyanate group, and “

n”

is average degree of polymerization, being in the range of 1 to 100;

R¹—

Y and Y—

R³ may be an isocyanate group itself on the way to carbodiimidation.

8. The composite particle according to claim 7, characterized in that the carbodiimide resin (B) has at least one kind of a hydrophilic segment, and is water-soluble.

9. A method for producing the composite particle according to any one of claims 1 to 8, comprising

a first step wherein a base particle (A) having a functional group reactable with a carbodiimide group and a carbodiimide resin (B) are mixed or immersed in the presence of at least one kind of a solvent selected from an organic solvent or water which is a non-solvent of the base particle (A) but a solvent of the carbodiimide resin (B), to sufficient degree that the carbodiimide resin (B) is impregnated at a surface layer part of the base particle (A), and

consecutively a second step wherein at the surface of the base particle (A), a shell layer which is comprised of the carbodiimide resin (B) is formed so as to cover the base particle (A), by a reaction of a functional group of the base particle (A) with a carbodiimide group of the carbodiimide resin (B).

10. The method for producing the composite particle according to claim 9, further comprising a preliminary step of forming said base particle (A) by suspension polymerization, emulsion polymerization, dispersion polymerization or seed polymerization.

11. The method for producing the composite particle according to claim 9, wherein in the first step the base particle (A) is immersed in a solution which is obtained by dissolving the carbodiimide resin (B) in at least one kind of a solvent selected from an organic solvent or water.