US 6,908,720 B2Granted

Polyhydroxyalkanoate, its production method, charge control agent containing the polyhydroxyalkanoate, toner binder and toner, and image forming method and image forming apparatus using the toner

AssigneeCanon Kabushiki Kaisha

InventorsTakashi Kenmoku, Toyoko Kobayashi, Etsuko Sugawa, Tetsuya Yano, Shin Kobayashi, Takeshi Imamura, Tsutomu Honma

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Abstract

The present invention provides a novel PHA comprising a unit containing thioether with high reactivity, and its production method. The present invention also provides polyhydroxyalkanoate (PHA) comprising units having defined chemical formulas (1) and (2), and at least one of four units having defined chemical formulas (3), (4), (5) and (6); its production method; a charge control agent containing the PHA; a toner binder containing the charge control agent; an electrostatic latent image developing toner; and an image forming method and an image forming apparatus using the electrostatic latent image developing toner.

Claims32

Dependent claims

A polyhydroxyalkanoate comprising units having the following chemical formulas (1) and (2) and at least one selected from four units having the following chemical formulas (3), (4), (5) and (6), in a molecule;

wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula.

15 more elements

In a charge control agent composition for controlling an electrostatic charging state of a powder particle, the improvement which comprises as a charge control agent, a polyhydroxyalkanoate including units having the following chemical formulas (1) and (2) and at least one selected from four types of units having the following chemical formulas (3), (4), (5) and (6):

wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula;
and
wherein R is a substituent optionally selected from H, a halogen atom, CN, NO2, COOR′, SO2R″, CH3, C2H5, CH3CH2CH2, (CH3)2CH and (CH3)3C (R′ is H, Na, K, CH3 or C2H5;
and R″ is OH, ONa, OK, a halogen atom, OCH3 or OC2H5);
and x is at least one optional integer value within the range shown in the formula.

16 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/133,576Filed 29 Apr 2002
Priority: JP 2001-13365127 Apr 2001
Published: US 2003/0104300 A15 Jun 2003
Granted: 21 Jun 2005
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

G03G 9/08771
Comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds: polymers having sulfur…
C08G 63/6882
Containing sulfur: derived from hydroxy carboxylic acids
C12P 7/625
Carboxylic acid esters: polyesters of hydroxy carboxylic acids
C12P 11/00
Preparation of sulfur-containing organic compounds