Production of colored vinyl polymer particles by polymerizing a vinyl polymerizable monomer with a polymerizable dye

• US 5,367,039 A
• Filed: 01/12/1993
• Issued: 11/22/1994
• Est. Priority Date: 07/06/1988
• Status: Expired due to Fees

• Current Assignee: Nippon Paint Company Limited (Rainbow Light Limited)
• Original Assignee: Nippon Paint Company Limited (Rainbow Light Limited)
• Inventors: Yabuuchi, Naoya, Kashihara, Akio, Otsuka, Chikayuki
• Primary Examiner(s): HENDERSON JR, CHRISTOPHER A
• Application Number:
  US08/003,669
• Time in Patent Office: 679 Days
• Field of Search: 526/284
• US Class Current: 526/284
• CPC Class Codes: C08F 246/00 Copolymers in which the nature of only the monomers in minority is defined

Abstract

Disclosed is a process for preparing a colored polymer without color change between a reactant color dye and an obtained polymer. The process of the present invention comprises polymerizing a vinyl polymerizable monomer (A), and a polymerizable dye (B) prepared by reacting a (meth)acryloyl compound having a group reactive with an active hydrogen, with a dye represented by the formula: ##STR1## wherein R₁ and R₂, which are the same or different, show a hydrogen atom or a group having the formula; ##STR2## (R₃ represents --(CH₂)m-NH₂, or --(CH₂)m-OH, R₄ represents a hydrogen atom, an alkyl group, a cycloalkyl group or an allyl group, n is an integer of 1 to 5 and m is 0 or an integer of 1 to 5), provided that both R₁ and R₂ do not represents a hydrogen atom, X and Y, which are different, --OH or --NHR₁,

in the presence of a polymerization initiator, and a color difference between the polymerizable dye and the obtained colored vinyl polymer is within ± 3 nm by absorption spectrum.

Claims

1. A process for preparing colored vinyl polymer particles which comprises suspension-polymerizing, dispersion-polymerizing or emulsion polymerizing:

(A) 100 parts by weight of a vinyl polymerizable monomer, and

(B) 0.1 to 99.9 parts by weight of a polymerizable dye prepared by reacting a (meth)acryloyl compound having a group reactive with an active hydrogen selected from the group consisting of (meth)acryloyl chloride, (meth)acryloyl isocyanate, isocyanatoethyl (meth)acrylate, ethoxalyloxyethyl (meth)acrylate and 2-vinylazlactone, with a dye represented by the formula;

##STR18## wherein R₁ and R₂, which are the same or different, represent a group having the formula;

##STR19## wherein R₃ represents --(CH₂)m-NH₂, or [--(CH₂),-OH]--(CH₂)m-OH, R₄ represents a hydrogen atom, an alkyl group, a cycloalkyl group or an allyl group, n is an integer of 1 to 5 and m is 0 or an integer of 1 to 5, and X and Y, which are different, represent --OH or --NHR₁,

in the presence of a polymerization initiator, and a color difference between the dye (1) to (6) and the obtained colored vinyl polymer particles is within ±

3nm as measured by absorption spectrum.

2. The process according to claim 1 wherein a reaction of the dye (1) to (6) and (meth)acryloyl chloride is carried out by dissolving the dyes in a suitable solvent followed by adding (meth)acryloyl chloride thereto in the presence of an tertiary amine.

3. The process according to claim 2 wherein said tertiary amine includes triethylamine, benzyldimethylamine or diazabicyclooctadecane.

4. The process according to claim 1 wherein a reaction of the dye (1) to (6) with (meth)acryloyl isocyanate, isocyanatoethyl (meth)acrylate, ethoxalyloxyethyl (meth)acrylate or 2-vinylazlactone takes place by simply mixing the both.

5. The process according to claim 1 wherein said polymerization initiator includes an azo compound and a peroxide.