Compound comprising crosslinked polyrotaxane

Details Compound comprising crosslinked polyrotaxane Compound comprising crosslinked polyrotaxane

2002-10-25

2004-12-07

Nutter, Nathan M. (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Mixing of two or more solid polymers; mixing of solid...

C525S403000, C525S418000, C525S420000, C525S452000, C525S454000, C525S461000, C525S919000

Reexamination Certificate

active

06828378

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a novel compound and a novel gelatinous material having high absorbability, uniform expandability, and elasticity or viscoelasticity. In particular, the present invention relates to a compound comprising crosslinked polyrotaxane, which is obtained by linking two or more polyrotaxane molecules through chemical bonds between cyclic molecules or rotators in the inter-polyrotaxane-molecules.
DESCRIPTION OF THE PRIOR ART
To date, there are various chemical and physical gels. Among these gels, chemical gels in general have a so-called network structure in which macromolecules are crosslinked to each other. Such a network structure has some problems: when tension is applied to chemical gels, the structure is broken down at locations where the distances between the crosslinking points are short, whereby the gel undergoes non-uniform destruction, since the structure does not have uniform distances from a crosslinking point to its neighboring points. On the other hand, physical gels are subjected to gelation by the attraction force between polymers. However, physical gels have problems: physical gels melt or dissolve at high temperatures or in solvents, and crystallize at low temperatures, since their structures are formed by the attraction force and the physical gels tend to undergo permanent deformation.
Gels in which crosslinking points are movable, gels in which multiple polymeric molecules are slidable against each other, the so-called slipping or sliding gels, have been proposed as models since 1950s in well known studies. The possibilities for a variety of applications of such gels have been discussed. However, such gels have not been actually made, and researchers have been focused on how to produce such gels.
Japanese Patent Laid-open Publication (JP-A) No. 6-25307 discloses compounds referred to as so-called polyrotaxane. These compounds are molecules in which plural alpha-cyclodextrin molecules as a rotator and a polyethylene glycol molecule as the axis are assembled by means of non-covalent bonding and each end of the axis is blocked with a blocking group. That is, compounds are disclosed in which a polyethylene glycol molecule has alpha-cyclodextrin molecules included in a skewered manner and each end of the polyethylene glycol molecule is blocked with a blocking group so as not to allow eliminating the alpha-cyclodextrin molecules from the polyethylene glycol molecule.
Although there are various chemical gels well known to date, all of these gels are characterized by their gradual breakdown against tension or stress. In other words, chemical gels undergo deformation in response to stress. Even though the shape of a chemical gel is retained as a whole, portions of the gel undergo microscopicaldestruction. Thus, chemical gels suffer from gradual breakdown. On the other hand, physical gels always tending to undergo permanent deformation leading to melt down at high temperatures, dissolution in solvents, and crystallization at low temperatures.
In addition, so-called slipping or sliding gels have been discussed in theory, and not realized yet.
Furthermore, JP-A No. 6-25307 discloses polyrotaxane that is a novel compound, and a process for producing the same, but does not describe its uses.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a third gel, that is, a novel gel having a structure and properties which are not possessed by conventional chemical and physical gels.
Further, an object of the present invention, as another object or in addition to the above-described object, is to provide a novel gel or compound in which movable crosslinking segments allow stress to be dispersed within the gel or compound, thereby providing the gel or compound with a higher fracture strength than those of chemical gels.
More, as another object or in addition to the above-described objects, an object of the present invention is to provide a novel gel or compound having higher entropic elasticity than those of physical gels.
Moreover, as another object or in addition to the above-described objects, an object of the present invention is to provide a novel biodegradable gel, a novel biodegradable compound that can be readily degraded by microorganisms.
The inventors have carried out intensive research, and as a result, found that the objects described above can be achieved by the present invention as illustrated by the following <1> to <77>:
<1> A compound comprising crosslinked polyrotaxane, wherein the crosslinked polyrotaxane has a first and a second polyrotaxane, the first polyrotaxane having a first linear molecule and a first cyclic molecule, the first linear molecule having the first cyclic molecule included in a skewered manner which allows the first linear molecule to pass through the opening of the first cyclic molecule, and having at each end a first blocking group which is placed so as to prevent the elimination of the first cyclic molecule; and the second polyrotaxane having a second linear molecule and a second cyclic molecule, the second linear molecule having the second cyclic molecule included in a skewered manner which allows the second linear molecule to pass through the opening of the second cyclic molecule, and having at each end a second blocking group which is placed so as to prevent the elimination of the second cyclic molecules, each opening of the first and second cyclic molecules is of substantial ring, and the crosslinked polyrotaxane is formed by linking at least one of the first cyclic molecules and at least one of the second cyclic molecules via chemical bonding.
<2> In the compound of item <1>, the first blocking group may have bulkiness and/or ionic property, thereby preventing the elimination of the first cyclic molecules.
<3> In the compound of item <1> or <2>, the second blocking group may have bulkiness and/or ionic property, thereby preventing the elimination of the second cyclic molecules.
<4> A compound comprising crosslinked polyrotaxane, wherein the crosslinked polyrotaxane has a first and a second polyrotaxane, the first polyrotaxane having a first linear molecule and a first cyclic molecule, the first linear molecule having the first cyclic molecule included in a skewered manner which allows the first linear molecule to pass through the opening of the first cyclic molecule, and having at each end a first blocking group which is bulky enough to prevent the elimination of the first cyclic molecule, the second polyrotaxane having a second linear molecule and a second cyclic molecule, the second linear molecule having the second cyclic molecule included in a skewered manner which allows the second linear molecule to pass through the opening of the second cyclic molecule, and having at each end a second blocking group which is bulky enough to prevent the elimination of the second cyclic molecules, each opening of the first and second cyclic molecule is substantially cyclic, and the crosslinked polyrotaxane is formed by linking at least one of the first cyclic molecules and at least one of the second cyclic molecules via chemical bonding.
<5> In any one of items <1> to <4>, the first linear molecule may have at least two first cyclic molecules included in a skewered manner and the second linear molecule may have at least two second cyclic molecules included in a skewered manner.
<6> In any one of items <1> to <5>, the first linear molecule may have the first cyclic molecules included in a skewered manner at an amount of 0.001 to 0.6, preferably 0.01 to 0.5, more preferably 0.05 to 0.4 of a first maximum inclusion amount, which is defined as an amount at which the first cyclic molecule can be included at the maximum when the first linear molecule has the first cyclic molecule included in a skewered manner, and the value at maximum is normalized to be 1; and the second linear molecule may have the second cyclic molecules included in a skewered manner at an amount of 0.001 to 0.6, preferably

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