IP Library Patent Application 13255544
Patent Application
App. No. 13/255,544

FUNCTIONALIZED 4- AND 5-VINYL SUBSTITUTED REGIOISOMERS OF 1, 2, 3-TRIAZOLES VIA 1, 3-DIPOLAR CYCLOADDITION AND POLYMERS THEREOF

Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US None
App. No.
13/255,544
Abstract

The present invention provides novel functionalized mixtures 4- and 5-vinyl substituted regioisomers of 1,2,3-triazoles via 1,3-dipolar cycloaddition. Functionalized alkyne moieties with a terminal alcoholic functionality are reacted with functionalized organic moieties with a terminal leaving group and an azide to provide an alcoholic functionalized mixture of 4- and 5-substituted regioisomers of 1,2,3-triazole moieties. The mixture may be converted to a wide variety of useful functionalized mixtures of 4- and 5-vinyl substituted regioisomers of 1,2,3-triazole moieties, which in turn can be converted to a wide variety of useful polymers The novel alcoholic functionalized mixtures of 4- and 5-substituted regioisomers can be separated by chromatography to provide the purified 4- and 5-alcoholic functionalized substituted 1,2,3-triazole moieties. The novel compounds of the invention can be employed in a wide variety of compositions (Formulae (I), (II)); wherein R 1 , R 2 , R 3 , and R 4 , are defined herein.

Claims (77)

1 . An alcoholic mixture of 4- and 5-substituted regioisomers of 1,2,3-triazole moieties.

2 . The alcoholic mixture according to claim 1 , wherein the mixture is represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

3 . The alcoholic mixture according to claim 1 , wherein the mixture is represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

4 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising an alcoholic mixture of 4- and 5-substituted regioisomers of 1,2,3-triazole moieties.

5 . The composition according to claim 4 , wherein the mixture is represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

6 . The composition according to claim 4 , wherein the mixture is represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

7 . An 4-alcoholic substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 2 to about 500.

8 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 4-alcoholic substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

9 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 4-alcoholic substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 2 to about 500.

10 . An 5-alcoholic substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

11 . An 5-alcoholic substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

12 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 5-alcoholic substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

13 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 5-alcoholic substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

14 . A mixture of 4- and 5-vinyl substituted regioisomers of 1,2,3-triazole moieties.

15 . The vinyl mixture according to claim 14 , wherein the mixture is represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

16 . The vinyl mixture according to claim 14 , wherein the mixture is represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

17 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a mixture of 4- and 5-vinyl substituted regioisomers of 1,2,3-triazole moieties.

18 . The composition according to claim 17 , wherein the mixture is represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

19 . The composition according to claim 17 , wherein the mixture is represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

20 . A 4-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 2 to about 500.

21 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 4-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

22 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 4-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

23 . A 5-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

24 . A 5-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

25 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 5-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond.

26 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 5-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; R 5 is selected from the group consisting of functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and x is an integer ranging from 1 to about 500.

27 . A homopolymer of a mixture of 4- and 5-vinyl substituted regioisomers of 1,2,3-triazole moieties.

28 . The homopolymer according to claim 27 , wherein the homopolymer is represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y is an integer ranging from 2 to about 10,000.

29 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a homopolymer of a mixture of 4- and 5-vinyl substituted regioisomers of 1,2,3-triazole moieties.

30 . The composition according to claim 29 , wherein the homopolymer is represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amities, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y is an integer ranging from 2 to about 10,000.

31 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a homopolymer of a 4-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y is an integer ranging from 2 to about 10,000.

32 . A homopolymer of a 5-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y is an integer ranging from 2 to about 10,000.

33 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a homopolymer of a 5-vinyl substituted 1,2,3-triazole moiety represented by the structure:

wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y is an integer ranging from 2 to about 10,000.

34 . A non-homopolymer of a mixture of 4- and 5-vinyl substituted regioisomers of 1,2,3-triazole moieties with a different polymerizable reactant moiety, wherein the non-homopolymer is a random, blocked, or alternating polymer.

35 . The non-homopolymer according to claim 34 , wherein the non-homopolymer is represented by the structure:

wherein M is based upon a different polymerizable reactant moiety, R 1 , R 2 and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y and z are integers independently ranging from about 2 to about 10,000, wherein the non-homopolymer is a random, blocked, or alternating polymer.

36 . The non-homopolymer according to claim 35 , wherein M is based upon a different polymerizable reactant moiety selected from the group consisting of anhydrides, vinyl pyrrolidones, vinyl caprolactams, acrylates, styrenes, maleimides, maleates, fumarates, cinnamyls, vinyl imidazoles, vinyl pyridines, vinyl acetates, acrylamides, vinyl sulfones, vinyl carbonates, vinyl silanes, vinyl acrylamides, allyl alcohols, vinyl ethers, and mixtures thereof.

37 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a non-homopolymer of a mixture of 4- and 5-vinyl substituted regioisomers of 1,2,3-triazole moieties with a different polymerizable reactant moiety, wherein the non-homopolymer is a random, blocked, or alternating polymer.

38 . The composition according to claim 37 , wherein the non-homopolymer is represented by the structure:

wherein M is based upon a different polymerizable reactant moiety, R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y and z are integers independently ranging from about 2 to about 10,000, wherein the non-homopolymer is a random, blocked, or alternating polymer.

39 . A non-homopolymer of a 4-vinyl substituted 1,2,3-triazole moiety with a different polymerizable reactant moiety, wherein the non-homopolymer is a random, blocked, or alternating polymer, wherein the non-homopolymer is represented by the structure:

wherein M is based upon a different polymerizable reactant moiety, R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y and z are integers independently ranging from about 2 to about 10,000, wherein the non-homopolymer is a random, blocked, or alternating polymer.

40 . The non-homopolymer according to claim 39 , wherein M is based upon a different polymerizable reactant moiety selected from the group consisting of anhydrides, vinyl pyrrolidones, vinyl caprolactams, acrylates, styrenes, maleimides, maleates, fumarates, cinnamyls, vinyl imidazoles, vinyl pyridines, vinyl acetates, acrylamides, vinyl sulfones, vinyl carbonates, vinyl silanes, vinyl acrylamides, allyl alcohols, vinyl ethers, and mixtures thereof.

41 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a non-homopolymer of a 4-vinyl substituted 1,2,3-triazole moiety with a different polymerizable reactant moiety, wherein the non-homopolymer is a random, blocked, or alternating polymer, wherein the non-homopolymer is represented by the structure:

wherein M is based upon a different polymerizable reactant moiety, R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amities, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y and z are integers independently ranging from about 2 to about 10,000, wherein the non-homopolymer is a random, blocked, or alternating polymer.

42 . A non-homopolymer of a 5-vinyl substituted 1,2,3-triazole moiety with a different polymerizable reactant moiety, wherein the non-homopolymer is a random, blocked, or alternating polymer, wherein the non-homopolymer is represented by the structure:

wherein M is based upon a different polymerizable reactant moiety, wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y and z are integers independently ranging from about 2 to about 10,000, wherein the non-homopolymer is a random, blocked, or alternating polymer.

43 . The non-homopolymer according to claim 42 , wherein M is based upon a different polymerizable reactant moiety selected from the group consisting of anhydrides, vinyl pyrrolidones, vinyl caprolactams, acrylates, styrenes, maleimides, maleates, fumarates, cinnamyls, vinyl imidazoles, vinyl pyridines, vinyl acetates, acrylamides, vinyl sulfones, vinyl carbonates, vinyl silanes, vinyl acrylamides, allyl alcohols, vinyl ethers, and mixtures thereof.

44 . An adhesive, coating, encapsulation, personal care, oilfield, membrane, agricultural, or cleaning composition comprising a 5-vinyl substituted 1,2,3-triazole moiety with a different polymerizable reactant moiety, wherein the non-homopolymer is a random, blocked, or alternating polymer, wherein the non-homopolymer is represented by the structure:

wherein M is based upon a different polymerizable reactant moiety, wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen, functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the before mentioned groups may be with or without heteroatoms; and R 4 is selected from the group consisting of a direct bond, carboxylic acids, esters, amides, anhydrides, aldehydes, ketones, ethers, amines, alcohols, and thiols; with the proviso that when R 3 is hydrogen, R 4 is a direct bond; and y and z are integers independently ranging from about 2 to about 10,000, wherein the non-homopolymer is a random, blocked, or alternating polymer.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2014
From: MARR, BRIAN B.
To: ISP INVESTMENTS INC.
Reel/Frame 033287/0114 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2014
From: MUSA, OSAMA M.
To: ISP INVESTMENTS INC.
Reel/Frame 033287/0373 →
RELEASE OF SECURITY AGREEMENT Recorded Aug 28, 2013
From: THE BANK OF NOVA SCOTIA
To: ASHLAND INC.; HERCULES INCORPORATED; ISP INVESTMENTS INC.; ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC
Reel/Frame 031106/0682 →
SECURITY AGREEMENT Recorded Oct 6, 2011
From: ISP INVESTMENTS INC.
To: ASHLAND INC.
Reel/Frame 027023/0500 →
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY DATA ADDRESS CHANGE EMAIL ADDRESS PREVIOUSLY RECORDED ON REEL 027023 FRAME 0500. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY AGREEMENT. Recorded Oct 6, 2011
From: ISP INVESTMENTS INC.
To: THE BANK OF NOVA SCOTIA, GWS LOAN OPERATIONS
Reel/Frame 027027/0526 →