Trigger-responsive chain-shattering polymers
View Patent ↗Disclosed are polymers containing a backbone comprising alternating N-protected hydroxymethylaniline units (“spacer”) and linker units.
1. A polymer comprising repeating units of Formula I:
wherein
R P is a nitrogen protecting group;
each R 1 is independently hydrogen, hydroxyalkyl, alkyl, alkoxy, or halogen,
q is 1, 2, or 3;
R L is a group of formula A or formula B:
where
Q and D are alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclyl, heteroalkyl, or heteroaryl, each of which is optionally substituted with one or more of alkyl, alkoxy, nitro, amino, aminoalkyl, cycloalkyl, oxo, imino, or halogen; and
R is H or alkyl;
R 2 is hydrogen, alkyl, alkenyl, alkyl-alkoxy, aryl, or arylalkyl; and n is from 2 to about 100,000.
2. A polymer according to claim 1 , where each R P is independently —X—Y—Z,
where
X is —CO—, —CO 2 —, —SO 2 —, or —C(O)NR″—, where R″ is H, alkyl, cycloalkyl, aryl or arylalkyl;
Y is —CH 2 —, —CH 2 CH 2 —, or a bond; and
Z is aryl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, heterocyclic, C(O)alkyl, alkyl-disulfide, or NR 23 R 24 , each of which is optionally substituted with one or more of aryl, alkyl, alkoxy, nitro, amino, aminoalkyl, cycloalkyl, oxo, imino, or halogen.
3. A polymer according to claim 1 , in the form of an oligomer, dendrimer, cross-linked network, strand, film, fiber, resin, adhesive, coating, hydrogel, organogel or particle.
4. A method for making a polymer of claim 1 , comprising:
mixing a compound of Formula II:
where
R 2 is hydrogen, alkyl, alkenyl, alkyl-alkoxy, aryl, or arylalkyl;
q is 1, 2, or 3;
each R 1 is independently hydrogen, —CH 2 OH, alkyl, aryl, alkoxy, arylalkyl, or halogen; provided that no more than one of R 1 is —CH 2 OH, and when R 1 is —CH 2 OH it is at the para position and/or remaining ortho position relative to N;
with one or more linking agents; and
(b) isolating a polymer of Formula I according to claim 1 .
5. A mixture comprising a polymer of claim 1 and one or more substances.
6. A method for release of the substance from the mixture of claim 5 comprising subjecting the mixture to depolymerization conditions.
7. A method for preparing the mixture of claim 6 comprising blending a polymer of claim 1 with a substance.