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US 10,227,433 B2Granted
Cycloalkylnorbornene monomers, polymers derived therefrom and their use in pervaporation
AssigneePromerus, LLC
InventorsAndrew Bell, Leah Langsdorf, Oleksandr Burtovyy
Life of this patent
Estimating the term…
Abstract
A variety of polycycloalkyl polynorbornene monomers and polymers derived therefrom are disclosed and claimed. The polymers and copolymers as disclosed herein are useful for forming pervaporation membranes, among other uses.
Claims13
A compound of formula (I):
- wherein:
- each occurrence of X independently represents —CH2—or —CH2—CH2—;
- m is an integer from 0 to 5 inclusive;
- at least one of R1, R2, R3 and R4 independently represents -L-(C7-C14)tricycloalkyl or a group of formula (A):
- wherein:
- each occurrence of Y independently represents —CH2—or —CH2—CH2—;
- n is 1;
- and
- R5, R6, R7 and R8 independently represents hydrogen, methyl, ethyl, linear or branched (C3-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C 14)tricycloalkyl, (C6-C 10)aryl, (C6-C10)aryl(C1-C3)alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C1)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C1)alkyl, (C5-C10)heteroaryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, or halogen;
- L represents a bond;
- or
- R1 and R3 taken together with the carbon atom to which they are attached form a substituted or unsubstituted (C5-C7)cycloalkyl or (C6-C12)bicycloalkyl ring;
- remaining one or more of R1, R2, R3 and R4 independently represents hydrogen, methyl, ethyl, linear or branched (C3-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C3)alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10))aryloxy(C1-C3)alkyl, (C5-C10)heteroaryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, or halogen;
- wherein each of aforementioned groups, where valence is permissible, is optionally substituted with one or more groups selected from (C1-C6)alkyl, (C3-C7)cycloalkyl, (C1-C6)perfluoroalkyl, halogen, hydroxy, acetoxy, phenyl, hydroxyphenyl, acetoxyphenyl and a group of formula (B):
- wherein:
- D is (CH2)r where r is an integer from 1to 5 inclusive, phenylene,
- C6H4(CH2)s where s is an integer from 1to 3 inclusive, or ((CH2)t—O)uwhere t and u independently are integers from 1to 4 inclusive;
- E is methyl, ethyl, CF3 or C2F5;
- and
- R13 is hydrogen or (C1-C5)alkyl.
17 more elements
A compound of formula (III):
- wherein:
- each occurrence of R5, R6, R7 and R8 independently represents hydrogen, methyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, CF3, bicycloheptyl, or phenyl.
A polymer comprising a first repeating unit represented by formula (IA), said repeating unit is derived from a monomer of formula (I):
- wherein:
- each occurrence of X independently represents —CH2—or —CH2—CH2—;
- m is an integer from 0 to 5 inclusive;
- at least one of R1, R2, R3 and R4 independently represents a group of formula (A):
- wherein:
- each occurrence of Y independently represents —CH2—or —CH2—CH2—;
- n is 0 or 1;
- and
- R5, R6, R7 and R8 independently represents hydrogen, methyl, ethyl, linear or branched (C3-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl,(C7-C 14)tricycloalkyl, (C6-C 10)aryl, (C6-C10)aryl(C1-C3)alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C5-C10)heteroaryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, or halogen;
- L represents a bond;
- or
- R1 and R3 taken together with the carbon atom to which they are attached form a substituted or unsubstituted (C5-C7)cycloalkyl or (C6-C12)bicycloalkyl ring;
- remaining one or more of R1, R2, R3 and R4 independently represents hydrogen, methyl, ethyl, linear or branched (C3-C3-12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C 14)tricycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C3)alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C5-C10)heteroaryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, or halogen;
- wherein each of aforementioned groups, where valence is permissible, is optionally substituted with one or more groups selected from (C1-C6)alkyl, (C3-C7)cycloalkyl, (C1-C6)perfluoroalkyl, halogen, hydroxy, acetoxy, phenyl, hydroxyphenyl, acetoxyphenyl and a group of formula (B):
- wherein:
- D is (CH2)r where r is an integer from 1to 5 inclusive, phenylene, C6H4(CH2)s where s is an integer from 1to 3 inclusive, or ((CH2)t—O)u where t and u independently are integers from 1to 4 inclusive;
- E is methyl, ethyl, CF3 or C2F5;
- and
- R13 is hydrogen or (C1-C5)alkyl.
16 more elements
A compound of formula (I):
- wherein:
- each occurrence of X independently represents —CH2—or —CH2—CH2—;
- m is an integer from 0 to 5 inclusive;
- at least one of R1, R2, R3 and R4 independently a group of formula (A):
- wherein:
- each occurrence of Y independently represents —CH2—or —CH2—CH2—;
- n is 0;
- and
- R5, R6, R7 and R8 independently represents hydrogen, methyl, linear or branched (C3-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C3)alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C5-C10)heteroaryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, or halogen;
- L represents a bond;
- or
- R1 and R3 taken together with the carbon atom to which they are attached form a substituted or unsubstituted (C5-C7)cycloalkyl or (C6-C12)bicycloalkyl ring;
- remaining one or more of R1, R2, R3 and R4 independently represents hydrogen, methyl, ethyl, linear or branched (C3-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10)aryl, (C6-C10 )aryl(C1-C3)alkyl, (C5-C10)heteroaryl, (C5-C10)heteroaryl(C1-C3)alkyl, hydroxy, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C5-C10)heteroaryloxy(C1-C3)alkyl, (C6-C10)aryloxy, (C5-C10)heteroaryloxy, (C1-C6)acyloxy, or halogen;
- wherein each of aforementioned groups, where valence is permissible, is optionally substituted with one or more groups selected from (C1-C6)alkyl, (C3-C7)cycloalkyl, (C1-C6)perfluoroalkyl, halogen, hydroxy, acetoxy, phenyl, hydroxyphenyl, acetoxyphenyl and a group of formula (B):
- wherein:
- D is (CH2)r where r is an integer from 1to 5 inclusive, phenylene,
- C6H4(CH2)s where s is an integer from 1to 3 inclusive, or ((CH2)t—O)u where t and u independently are integers from 1to 4 inclusive;
- E is methyl, ethyl, CF3 or C2F5;
- and
- R13 is hydrogen or (C1-C5)alkyl.
17 more elements
Dependencies are inferred from the claim text.