Toner and method for producing toner
Provided is a toner has a toner particle containing a binder resin and is characterized in that the binder resin contains a polymer A, which is a polymer of a composition containing a first polymerizable monomer, a second polymerizable monomer and a crosslinking agent, the first polymerizable monomer is at least one monomer selected from the group consisting of (meth)acrylic acid esters having an alkyl group with 18 to 36 carbon atoms, the crosslinking agent has two or more polymerizable double bonds, a content of the first polymerizable monomer in the composition is 5.0 to 60.0 mol %, a content of the second polymerizable monomer is 20.0 to 95.0 mol %, and when the SP values of the first polymerizable monomer, the second polymerizable monomer and the crosslinking agent are denoted by SP 12 , SP 22 and SP C2 , respectively, the formulae 0.60≤(SP 22 −SP 12 )≤15.00 and SP 12 <SP C2 <(SP 22 +3.00) are satisfied.
1. A toner, comprising:
a toner particle comprising a binder resin;
the binder resin comprising polymer A, polymer A being a polymer of a composition containing a first polymerizable monomer, a second polymerizable monomer that is different from the first polymerizable monomer, and a crosslinking agent;
the first polymerizable monomer being at least one monomer selected from the group consisting of (meth)acrylic acid esters having an alkyl group with 18 to 36 carbon atoms, a content of the first polymerizable monomer in the composition being 5.0 to 40.0 mol% based on the total number of moles of all polymerizable monomers and the crosslinking agent in the composition;
a content of the second polymerizable monomer in the composition being 40.0 to 92.6 mol% based on the total number of moles of all polymerizable monomers and the crosslinking agent in the composition; and
the crosslinking agent having two or more polymerizable double bonds, a content of the crosslinking agent in the composition being 0.2 to 5.0 mol% based on the total number of moles of all polymerizable monomers and the crosslinking agent in the composition, wherein
0.60≤(SP 22 -SP 12 )≤15.00 and SP 12 <SP C2 <(SP 22 +3.00) when SP 12 (J/cm 3 ) 5 is the SP value of the first polymerizable monomer, SP 22 (J/cm 3 ) 5 is the SP value of the second polymerizable monomer and SP C2 (J/cm 3 ) 5 is the SP value of the crosslinking agent.
2. The toner according to claim 1 , wherein a content of polymer A in the binder resin is at least 50.0 mass %.
3. The toner according to claim 1 , wherein the first polymerizable monomer is at least one monomer selected from the group consisting of (meth)acrylic acid esters having a straight chain alkyl group with 18 to 36 carbon atoms.
4. The toner according to claim 1 , wherein the second polymerizable monomer is at least one monomer selected from the group consisting of formulae (A) and (B)
where X denotes a single bond or an alkylene group with 1 to 6 carbon atoms,
R 1 denotes —C≡N, —C(═O)NHR 10 where R 10 is a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, a hydroxyl group, —COOR 11 where R 11 is an alkyl group with 1 to 6 carbon atoms or a hydroxyalkyl group with 1 to 6 carbon atoms, —NHCOOR 12 where R 12 is an alkyl group with 1 to 4 carbon atoms, —NH—C(═O)—N(R 13 ) 2 , where R 13 groups are independently a hydrogen atom or an alkyl group with 1 to 6 carbon atoms, —COO(CH 2 ) 2 NHCOOR 14 where R 14 is an alkyl group with 1 to 4 carbon atoms, or —COO(CH 2 ) 2 —NH—C(═O)—N(R 15 ) 2 where R 15 groups are independently a hydrogen atom or an alkyl group with 1 to 6 carbon atoms,
R 2 denotes an alkyl group with 1 to 4 carbon atoms, and
R 3 denotes a hydrogen atom or a methyl group.
5. The toner according to claim 1 , wherein the second polymerizable monomer is at least one monomer selected from the group consisting of following formulae (A) and (B)
where X denotes a single bond or an alkylene group with 1 to 6 carbon atoms, R 1 denotes —C≡N, an amido group —C(═O)NHR 10 , where R 10 is a hydrogen atom or an alkyl group with 1 to 4 carbon atoms, a hydroxyl group, —COOR 11 where R 11 is an alkyl group with 1 to 6 carbon atoms or a hydroxyalkyl group with 1 to 6 carbon atoms, —NH—C(═O)—N(R 13 ) 2 where R 13 groups are independently a hydrogen atom or an alkyl group with 1 to 6 carbon atoms, —COO(CH 2 ) 2 NHCOOR 14 where R 14 is an alkyl group with 1 to 4 carbon atoms, or —COO(CH 2 ) 2 —NH—C(═O)—N(R 15 ) 2 where R 15 groups are independently a hydrogen atom or an alkyl group with 1 to 6 carbon atoms,
R 2 denotes an alkyl group with 1 to 4 carbon atoms, and
R 3 denotes a hydrogen atom or a methyl group.
6. The toner according to claim 1 , wherein the composition further comprises a third polymerizable monomer that is different from each of the first polymerizable monomer, the second polymerizable monomer and the crosslinking agent, the third polymerizable monomer being at least one polymerizable monomer selected from the group consisting of styrene, methyl methacrylate and methyl acrylate.
7. The toner according to claim 1 , wherein (SP 22min -SP C2 )<(SP C2 -SP 12max ) when SP 12max (J/cm 3 ) 0.5 is the SP value of a polymerizable monomer having the highest SP value among the first polymerizable monomers, SP 22max (J/cm 3 ) 0.5 is the SP value of a polymerizable monomer having the lowest SP value among the second polymerizable monomers, and SP 22min (J/cm 3 ) 0.5 is the SP value of the crosslinking agent.
8. The toner according to claim 1 , wherein the crosslinking agent has a molecular weight of at least 300.
9. The toner according to claim 1 , wherein the first polymerizable monomer is at least one monomer selected from the group consisting of stearyl (meth)acrylate and behenyl (meth)acrylate.
10. The toner according to claim 1 , wherein the content of the crosslinking agent in the composition is 0.2 to 2.8 mol % based on the total number of moles of all polymerizable monomers and the crosslinking agent in the composition.
11. The toner according to claim 1 , wherein the content of the second polymerizable monomer in the composition is 40.0 to 70.0 mol% based on the total number of moles of all polymerizable monomers and the crosslinking agent in the composition.
12. A method for producing a toner having a toner particle, the method comprising
a step of forming a particle of a polymerizable monomer composition containing polymerizable monomers in an aqueous medium, and
a step of obtaining the toner particle, which contains polymer A obtained by polymerizing the polymerizable monomers contained in the particle,
the polymerizable monomer composition containing a first polymerizable monomer, a second polymerizable monomer that is different from the first polymerizable monomer, and a crosslinking agent,
the first polymerizable monomer being at least one monomer selected from the group consisting of (meth)acrylic acid esters having an alkyl group with 18 to 36 carbon atoms, a content of the first polymerizable monomer in the composition being 5.0 to 40.0 mol % based on the total number of moles of all polymerizable monomers and the crosslinking agent in the composition;
a content of the second polymerizable monomer in the composition being 40.0 to 92.6 mol % based on the total number of moles of all polymerizable monomers and the crosslinking agent in the composition; and
the crosslinking agent having two or more polymerizable double bonds, a content of the crosslinking agent in the composition being 0.2 to 5.0 mol % based on the total number of moles of all polymerizable monomers and the crosslinking agent in the composition, wherein
0.60≤(SP 22 -SP 12 )≤15.00 and SP 12 <SP C2 <(SP 22 +3.00) when SP 12 (J/cm 3 ) 5 is the SP value of the first polymerizable monomer, SP 22 (J/cm 3 ) 5 is the SP value of the second polymerizable monomer and SP C2 (J/cm 3 ) 5 is the SP value of the crosslinking agent.