Nanofiltration membranes and methods of use

Patent metadata

Field	Value
Publication number	US-2016288057-A1
Application number	US-201615176110-A
Country	US
Kind code	A1
Filing date	Jun 7, 2016
Priority date	Dec 7, 2013
Publication date	Oct 6, 2016
Grant date	—

Abstract

The present invention provides nanofiltration membranes with reduced chemical reactivity that can be utilized in manufacturing processes where reactive feedstocks and/or products are utilized or produced. Methods of making and using the membranes are also provided.

First claim

1 . A nanofiltration membrane comprising a polysiloxane polymer, wherein the polysiloxane polymer comprises less than 500 nmol of free —Si(OH)— containing groups per gram of polysiloxane.

2 . The nanofiltration membrane of claim 1 , comprising polydimethylsiloxane.

3 . The nanofiltration membrane of claim 1 , wherein the polysiloxane polymer is crosslinked.

4 . The nanofiltration membrane of claim 1 , wherein the polysiloxane polymer is treated with a reagent reactive toward —OH groups, wherein the reagent is an alkyl chloride, alkyl bromide, alkyl iodide, alkyl sulfonate ester, sulfonyl chloride, sulfonic acid anhydride, isocyanate, acid chloride, acid anhydride, alkyl chloroformate, aryl chloroformate or R 3 SiX, wherein R is an aliphatic or aryl group and X is halogen.

5 . A nanofiltration membrane comprising a co-polymer, the co-polymer comprising a monomer of Formula M1 and one or more monomers of Formulae M1a, M2 and M3:

wherein:
each Ar 1 is a tetravalent aromatic moiety;
each

represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
each

represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
n is any integer up to about 100,000;
Z is a functional group that does not contain a nitrogen atom;
Z 1 is —H, aliphatic, acyl or aryl;
Z 2 is selected from the group consisting of: aliphatic, aryl, acyl, —C(O)OR x , —SO 2 R x and —C(O)NHR x ;
where Z 1 and Z 2 may optionally be taken together to form a ring,
R z is an optionally substituted aliphatic or optionally substituted aromatic group; and
R x is an optionally substituted aliphatic or optionally substituted aromatic group.

6 . The nanofiltration membrane of claim 5 , the co-polymer comprising a monomer of Formulae M2a to M2j:

wherein:
R a is —H, or an optionally substituted radical selected from the group consisting of C 1-20 aliphatic, C 1-2 heteroaliphatic, 3- to 12-membered heterocyclic, and 6- to 12-membered aryl;
each of R b and R c are independently selected from the group consisting of: —H; optionally substituted C 1 to C 12 aliphatic; optionally substituted 3- to 14-membered carbocyclic; and optionally substituted 3- to 14 membered heterocyclic, where R b and R c may be taken together with intervening atoms to form one or more optionally substituted rings;
R e is one or more moieties selected from the group consisting of: —H, halogen, —OR, —NR 2 , —SR, —CN, —SO 2 R, —SOR, —CO 2 R, —C(O)R, —OC(O)R, SO 2 NR 2 ; —CNO, —NRSO 2 R, —N 3 , —SiR 3 ; or an optionally substituted group selected from the group consisting of C 1-20 aliphatic; C 1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6-10-membered aryl; 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4-7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
R is H, optionally substituted aliphatic or optionally substituted aromatic;
is a single or double bond;
ring A is an optionally substituted aryl ring or an optionally substituted saturated or partially unsaturated mono- or polycyclic ring optionally containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur; and
ring B represents an optionally substituted 5- or 6-membered saturated, partially unsaturated or aromatic ring optionally containing one or more additional heteroatoms, selected from the group consisting of nitrogen, oxygen, and sulfur, which may be part of a larger fused ring system.

7 . The nanofiltration membrane of claim 5 , the co-polymer comprising a monomer of Formulae M3a or M3b:

wherein
X b is Cl, Br or I.

8 . The nanofiltration membrane of claim 5 , wherein:
each Ar 1 is independently selected from the group consisting of:

and
Q is selected from the group consisting of:

9 . A nanofiltration membrane comprising a co-polymer, the co-polymer comprising a monomer of Formula M4 and one or more of a monomer of Formula M5 and a group of Formula M6:

wherein:
each Ar 2 is a trivalent aromatic moiety;
each

represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
each

represents a bivalent linker and may be the same or different at each occurrence in the co-polymer;
n is any integer up to about 100,000;
Z 1 is —H, aliphatic, acyl, or aryl;
Z 2 is selected from the group consisting of: aliphatic, aryl, acyl, —C(O)OR x , —SO 2 R x , and —C(O)NHR x ;
where Z 1 and Z 2 may optionally be taken together to form a ring;
R x is an optionally substituted aliphatic or optionally substituted aromatic group; and
R a is —H, or an optionally substituted radical selected from the group consisting of C 1-20 aliphatic, C 1-20 heteroaliphatic, 3- to 12-membered heterocyclic, and 6- to 12-membered aryl.

10 . The nanofiltration membrane of claim 9 , the co-polymer comprising a monomer of Formulae M5a to M5j:

wherein:
R e is one or more moieties selected from the group consisting of: —H, halogen, —OR, —NR 2 , —SR, —CN, —SO 2 R, —SOR, —CO 2 R, —C(O)R, —OC(O)R, SO 2 NR 2 ; —CNO, —NRSO 2 R, —N 3 , —SiR 3 ; or an optionally substituted group selected from the group consisting of C 1-20 aliphatic; C 1-20 heteroaliphatic having 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur; 6-10-membered aryl; 5-10-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur; and 4-7-membered heterocyclic having 1-2 heteroatoms independently selected from the group consisting of nitrogen, oxygen, and sulfur;
R is H, or optionally substituted aliphatic or optionally substituted aromatic;
ring A is an optionally substituted aryl ring or an optionally substituted saturated or partially unsaturated mono- or polycyclic ring optionally containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen,

Assignees

• Novomer Inc

Inventors

• Lapointe Robert E
• Allen Scott D
• Lee Han
• Widzinski Thomas
• Farmer Jay J

Classifications

• B01D2323/36

  Introduction of specific chemical groups · CPC title

• B01D2323/30

  Cross-linking · CPC title

• B01D71/56

  Polyamides, e.g. polyester-amides · CPC title

• B01D71/82

  characterised by the presence of specified groups, e.g. introduced by chemical after-treatment · CPC title

• B01D71/76

  Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 (rubbers in general B01D71/24) · CPC title