Polycarbonate resin, process for producing the same and electrophotographic photoreceptor using the same
View Patent ↗The present invention provides an electrophotographic photoreceptor having excellent lubricity and abrasion resistance by using a novel polycarbonate resin comprising structural units having a polysiloxane chain in the shape of grafts as represented by the following general formula (1) with a viscosity-average molecular weight of 12,000 to 100,000 as a binder resin for a charge transport layer of a electrophotographic photoreceptor. wherein R 1 to R 5 each independently represents hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group, an aryl group, an alkoxy group or an aralkyl group. R 6 represents an alkylene group. Y represents a polysiloxane chain.
1. A polycarbonate resin having a viscosity-average molecular weight of 12,000 to 100,000 which is composed mainly by a structural unit represented by the following formula (1) and a structural unit represented by the following formula (2):
wherein:
R 1 to R 5 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 20 carbon atoms which may have substituents, an aryl group having 6 to 12 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents and an aralkyl group having 7 to 17 carbon atoms which may have substituents;
R 6 represents an alkylene group having 1 to 20 carbon atoms which may have substituents; and
Y represents a group selected from the following groups:
wherein R 7 to R 20 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 20 carbon atoms which may have substituents, an aryl group having 6 to 12 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents and an aralkyl group having 7 to 17 carbon atoms which may have substituents; and
“a”, “b”, and “c” each represents an integer of not less than 1;
wherein:
R 21 to R 24 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 20 carbon atoms which may have substituents, an aryl group having 6 to 12 carbon atoms which may have substituents, an alkenyl group having 2 to 12 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents and an aralkyl group having 7 to 17 carbon atoms which may have substituents; and
X represents a group selected from the following groups:
wherein:
R 25 and R 26 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 20 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents, an aryl group having 6 to 12 carbon atoms which may have substituents, or R 25 and R 26 may be combined with each other to represent as a whole a group forming a carbon ring of 5 to 20 carbon atoms or a heterocyclic ring of 5 to 12 elements;
R 27 and R 28 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 9 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents, an alkenyl group having 2 to 12 carbon atoms which may have substituents, and an aryl group having 6 to 12 carbon atoms which may have substituents;
R 29 represents an alkylene group having 1 to 9 carbon atoms which may have substituents;
“d” represents an integer of 0 to 20; and
“e” represents an integer of 1 to 500.
2. The polycarbonate resin according to claim 1 , wherein R 6 in the formula (1) represents an alkylene group having 4 to 20 carbon atoms.
3. The polycarbonate resin according to claim 1 , wherein “a”, “b”, and “c” in the formula (1) each represents an integer of 1 to 200.
4. The polycarbonate resin according to claim 1 , wherein R 7 to R 20 in the formula (1) each represents a methyl group or a phenyl group.
5. The polycarbonate resin according to claim 1 , wherein R 1 to R 4 in the formula (1) each represents a group selected from the group consisting of hydrogen, a methyl group, a butyl group and a phenyl group.
6. The polycarbonate resin according to claim 1 , wherein the ratio of the structural unit represented by the formula (1) and the structural unit represented by the formula (2) is (1):(2)=0.1-70:99.9-30 in a weight ratio.
7. The polycarbonate resin according to claim 2 , wherein “a”, “b”, and “c” in the formula (1) each represents an integer of 1 to 200.
8. The polycarbonate resin according to claim 2 , wherein R 7 to R 20 in the formula (1) each represents a methyl group or a phenyl group.
9. The polycarbonate resin according to claim 2 , wherein R 1 to R 4 in the formula (1) each represents a group selected from the group consisting of hydrogen, a methyl group, a butyl group and a phenyl group.
10. The polycarbonate resin according to claim 2 , wherein the ratio of the structural unit represented by the formula (1) and the structural unit represented by the formula (2) is (1):(2)=0.1-70:99.9-30 in a weight ratio.
11. A process for producing the polycarbonate resin according to claim 1 , which comprises a step of reacting bisphenol represented by the following formula (1′) and bisphenol represented by the following formula (2′) with a carbonate-forming compound;
wherein:
R 1 to R 5 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 20 carbon atoms which may have substituents, an aryl group having 6 to 12 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents and an aralkyl group having 7 to 17 carbon atoms which may have substituents;
R 6 represents an alkylene group having 1 to 20 carbon atoms which may have substituents; and
Y represents a group selected from the following groups:
wherein R 7 to R 20 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 20 carbon atoms which may have substituents, an aryl group having 6 to 12 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents and an aralkyl group having 7 to 17 carbon atoms which may have substituents; and
“a”, “b”, and “c” each represents an integer of not less than 1;
wherein:
R 21 to R 24 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 20 carbon atoms which may have substituents, an aryl group having 6 to 12 carbon atoms which may have substituents, an alkenyl group having 2 to 12 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents and an aralkyl group having 7 to 17 carbon atoms which may have substituents; and
X represents a group selected from the following groups:
wherein:
R 25 and R 26 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 20 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents, an aryl group having 6 to 12 carbon atoms which may have substituents, or R 25 and R 26 may be combined with each other to represent as a whole a group forming a carbon ring of 5 to 20 carbon atoms or a heterocyclic ring of 5 to 12 elements;
R 27 and R 28 each independently represents a group selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, an alkyl group having 1 to 9 carbon atoms which may have substituents, an alkoxy group having 1 to 5 carbon atoms which may have substituents, an alkenyl group having 2 to 12 carbon atoms which may have substituents, and an aryl group having 6 to 12 carbon atoms which may have substituents;
R 29 represents an alkylene group having 1 to 9 carbon atoms which may have substituents;
“d” represents an integer of 0 to 20; and
“e” represents an integer of 1 to 500.
12. The process for producing a polycarbonate resin according to claim 11 , wherein said bisphenol represented by the formula (1′) is selected from the group consisting of the compounds represented by following structures:
13. The process for producing a polycarbonate resin according to claim 11 , wherein said bisphenol represented by the formula (2′) is selected from the group consisting of 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl) propane, bis(4-hydroxyphenyl)ether, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, 1,1-bis(4-hydroxyphenyl)ethane, and 1,1′-biphenyl-4,4′-diol.
14. The process for producing a polycarbonate resin according to claim 11 , wherein said carbonate-forming compound is phosgene.
15. The process for producing a polycarbonate resin according to claim 11 , wherein the proportion of the bisphenol represented by the formula (1′) is 0.1 to 60% by weight based upon the total amount of bisphenol used.
16. An electrophotographic photoreceptor using the polycarbonate resin according to claim 1 as a binder resin of a charge transport layer thereof.
17. An electrophotographic photoreceptor using the polycarbonate resin according to claim 2 as a binder resin of a charge transport layer thereof.