Polyrotaxane having substituent having polyalkylene oxide chain or derivative thereof in cyclic molecule, and method for producing said polyrotaxane
The present invention provides a polyrotaxane having high durability and in particular, high hydrolysis resistance, and a method for producing said polyrotaxane. The present invention provides a polyrotaxane obtained by disposing blocking groups on both ends of a pseudopolyrotaxane so that an annular molecule cannot be displaced, said pseudopolyrotaxane being obtained by forming a clathrate by piercing the opening of the cyclic molecule with a linear molecule, said polyrotaxane being characterized in that the cyclic molecule has a substituent represented by formula I (in formula I, R 1 represents a group such as —CH 3 and —CH 2 —CH 3 , R 2 represents H or a group such as —CH 3 , and n is the apparent degree of polymerization of a polyalkylene oxide chain or a derivative thereof added to the cyclic molecule, the value of n being 1.1 to 10.0).
1. A polyrotaxane comprising a pseudopolyrotaxane, which has a linear molecule and a cyclic molecule(s) in which the linear molecule is included in a cavity (cavities) of the cyclic molecule(s) in a skewered manner, and capping groups, each of which locates at each end of the pseudopolyrotaxane in order to prevent the dissociation of the cyclic molecule(s),
wherein the cyclic molecule has a substituent represented by following formula I, wherein R 1 represents at least one group selected from the group consisting of —CH 3 , —CH 2 —CH 3 , —CH 2 —O—CH 3 , —CH 2 —O—CH 2 —CH 3 , —CH 2 —O—CH—(CH 3 ) 2 , and -phenyl group;
R 2 represents at least one group selected from the group consisting of H, —CH 3 , —OCONH—(CH 2 ) 3 —CH 3 , —OCONH—C 18 H 37 , and —COCH 3 ;
n represents an apparent degree of polymerization of a polyalkylene oxide chain or a derivative thereof added to the cyclic molecule, and the value of n ranges from 1.1 to 10.0:
2. A method for preparing a polyrotaxane B, comprising the steps of:
(a) preparing a polyrotaxane A which comprises a pseudopolyrotaxane, which has a linear molecule and a cyclic molecule(s) in which the linear molecule is included in a cavity (cavities) of the cyclic molecule(s) in a skewered manner, and capping groups, each of which locates at each end of the pseudopolyrotaxane in order to prevent the dissociation of the cyclic molecule(s); and
(b) reacting a compound represented by following formula II, wherein R 1 represents at least one group selected from the group consisting of —CH 3 , —CH 2 —CH 3 , —CH 2 —O—CH 3 , —CH 2 —O—CH 2 —CH 3 , —CH 2 —O—CH—(CH 3 ) 2 , with the polyrotaxane A to provide a substituent represented by following formula I wherein R 1 has the same definition as described above; R 2 represents at least one group selected from the group consisting of H, —CH 3 , —OCONH—(CH 2 ) 3 —CH 3 , —OCONH—C 18 H 37 , and —COCH 3 ; and n represents an apparent degree of polymerization of a polyalkylene oxide chain or a derivative thereof added to the cyclic molecule, and the value of n ranges from 1.1 to 10.0, wherein the reaction is carried out in the presence of i) a super strong base, or ii) a polymerization initiator;
thereby to obtain the polyrotaxane B in which the cyclic molecule comprises the substituent represented by following formula I:
3. A material comprising a polyrotaxane comprising a pseudopolyrotaxane, which has a linear molecule and a cyclic molecule(s) in which the linear molecule is included in a cavity (cavities) of the cyclic molecule(s) in a skewered manner, and capping groups, each of which locates at each end of the pseudopolyrotaxane in order to prevent the dissociation of the cyclic molecule(s),
wherein the cyclic molecule has a substituent represented by following formula I, wherein R 1 represents at least one group selected from the group consisting of —CH 3 , —CH 2 —CH 3 , —CH 2 —O—CH 3 , —CH 2 —O—CH 2 —CH 3 , —CH 2 —O—CH—(CH 3 ) 2 , and -phenyl group;
R 2 represents at least one group selected from the group consisting of H, —CH 3 , —OCONH—(CH 2 ) 3 —CH 3 , —OCONH—C 18 H 37 , and —COCH 3 ;
n represents an apparent degree of polymerization of a polyalkylene oxide chain or a derivative thereof added to the cyclic molecule, and the value of n ranges from 1.1 to 10.0:
4. The material according to claim 3 , further comprising a substance other than the polyrotaxane,
wherein the substance and a part of the polyrotaxane are directly or indirectly bound to each other.