US4395541A — Ionene polymer and preparation thereof

Claim 1

Independent Claim 393 words

A polymer having units of the formula ##STR24## wherein R 1 , R 2 , R 3 and R 4 , each independently represent a hydrocarbon group containing up to 20 carbon atoms, or at least one pair selected from the group consisting of R 1 , R 2 and R 3 , R 4 , together with the nitrogen atom to which it is attached, forms a heterocycle selected from the group consisting of a heterocycle wherein the heteroatom is nitrogen and a heterocycle containing nitrogen as a first heteroatom and a second heteroatom selected from the group consisting of oxygen and sulfur; A 1 and A 2 each independently represents a linear or branched alkylene, or aryl, containing up to 20 carbon atoms; X represents --SO 2 -- or --CO--; R 5 and R 6 represent hydrogen or lower alkyl when X represents --SO 2 --; or R 5 and R 6 , together, represent ##STR25## when X represents --CO--; R 7 and R 8 represent hydrogen or lower alkyl; A 3 represents alkylene, cycloalklene, alkenylene or cycloalkenylene, containing 2 to 20 carbon atoms, or at least one or said alkylene, cycloalkylene, alkenylene and cycloalkylene, interrupted by at least one heteroatom or by at least one of an arylene or cycloalkylene group, or A 3 represents polyoxyalkylene or --B 1 --D--B 2 -- wherein B 1 and B 2 represent alkylene having from 1 to 12 carbon atoms, or arylene, and D represents a member selected from the group consisting of ##STR26## --CONH--, --CO--O--, --O--CONH--, --CO--D 2 --CO-- and --O--CO--D 3 --CO--O--, wherein D 1 represents alkylene, alkylene interrupted by a --S--S-- group, alkenylene, arylene, diaminoalkylene, diaminoarylene, dioxyalkylene, polyoxyalkylene or dioxyarylene, or D 1 represents a direct covalent bond, y is a number equal to 0 or 1, R 10 and R 11 represent hydrogen or lower alkyl, or when y is 0, R 10 and R 11 , together, represent ##STR27## D 2 represents diaminoalkylene, dioxyalkylene, polyoxyalkylene or dithioalkylene, D 3 represents alkylene, arylene, diaminoalkylene, diaminocycloalkylene or diaminoarylene, or A 3 , together with the two nitrogens to which it is attached and with at least one of the pairs R 1 , R 3 and R 2 , R 4 , represents a cyclic or polycyclic group having from 4 to 6 carbon atoms; and Z.sup.⊖ represents an anion.

Claim 2

Dependent Claim 393 words

A polymer having units of the formula ##STR24## wherein R 1 , R 2 , R 3 and R 4 , each independently represent a hydrocarbon group containing up to 20 carbon atoms, or at least one pair selected from the group consisting of R 1 , R 2 and R 3 , R 4 , together with the nitrogen atom to which it is attached, forms a heterocycle selected from the group consisting of a heterocycle wherein the heteroatom is nitrogen and a heterocycle containing nitrogen as a first heteroatom and a second heteroatom selected from the group consisting of oxygen and sulfur; A 1 and A 2 each independently represents a linear or branched alkylene, or aryl, containing up to 20 carbon atoms; X represents --SO 2 -- or --CO--; R 5 and R 6 represent hydrogen or lower alkyl when X represents --SO 2 --; or R 5 and R 6 , together, represent ##STR25## when X represents --CO--; R 7 and R 8 represent hydrogen or lower alkyl; A 3 represents alkylene, cycloalklene, alkenylene or cycloalkenylene, containing 2 to 20 carbon atoms, or at least one or said alkylene, cycloalkylene, alkenylene and cycloalkylene, interrupted by at least one heteroatom or by at least one of an arylene or cycloalkylene group, or A 3 represents polyoxyalkylene or --B 1 --D--B 2 -- wherein B 1 and B 2 represent alkylene having from 1 to 12 carbon atoms, or arylene, and D represents a member selected from the group consisting of ##STR26## --CONH--, --CO--O--, --O--CONH--, --CO--D 2 --CO-- and --O--CO--D 3 --CO--O--, wherein D 1 represents alkylene, alkylene interrupted by a --S--S-- group, alkenylene, arylene, diaminoalkylene, diaminoarylene, dioxyalkylene, polyoxyalkylene or dioxyarylene, or D 1 represents a direct covalent bond, y is a number equal to 0 or 1, R 10 and R 11 represent hydrogen or lower alkyl, or when y is 0, R 10 and R 11 , together, represent ##STR27## D 2 represents diaminoalkylene, dioxyalkylene, polyoxyalkylene or dithioalkylene, D 3 represents alkylene, arylene, diaminoalkylene, diaminocycloalkylene or diaminoarylene, or A 3 , together with the two nitrogens to which it is attached and with at least one of the pairs R 1 , R 3 and R 2 , R 4 , represents a cyclic or polycyclic group having from 4 to 6 carbon atoms; and Z.sup.⊖ represents an anion.

Claim 3

Dependent Claim 78 words

The polymer of claim 1 wherein, when A 3 represents alkylene or cycloalkylene, A 3 represents a member selected from the group consisting of ##STR28## wherein R 12 and R 13 represent hydrogen, lower alkyl, lower hydroxyalkyl, halogen, carboxy, alkoxycarbonyl or phenyl, Y represents a direct covalent bond, or Y represents --O--, --CO--, --CHOH--, --SO 2 -- or alkylene, n is a number ranging from 1 to 6; and p is a number ranging from 1 to 3.

Claim 4

Dependent Claim 38 words

The polymer of claim 1 wherein, when A 3 represents a cyclic or polycyclic group, A 3 represents a member selected from the group consisting of ##STR29## where R 2 and R 4 are defined in claim 1.

Claim 5

Dependent Claim 22 words

The polymer of claim 1 wherein Z - represents an anion derived from a mineral acid or low molecular weight organic acid.

Claim 6

Dependent Claim 18 words

The polymer of claim 4 wherein Z - represents a halide, nitrate, sulfate, acetate or paratoluene sulfonate anion.

Claim 7

Dependent Claim 34 words

The polymer of claim 1 wherein R 1 , R 2 , R 3 and R 4 each independently, represent an aryl, aliphatic, alicyclic or arylaliphatic group containing a maximum of 20 carbon atoms.

Claim 8

Dependent Claim 51 words

The polymer of claim 6 wherein R 1 , R 2 , R 3 and R 4 each independently represent alkyl or hydroxyalkyl containing 1-8 carbon atoms, cycloalkyl-alkyl having less than 20 carbon atoms, cycloalkyl having 5 or 6 carbon atoms or aralkyl wherein the alkyl group contains 1-3 carbon atoms.

Claim 9

Dependent Claim 49 words

The polymer of claim 1 wherein, when at least one of the pairs R 1 , R 2 and R 3 , R 4 together with the nitrogen atom to which it is attached forms a ring, said pair represents a polymethylene group having 2 to 6 carbon atoms.

Claim 10

Dependent Claim 44 words

The polymer of claim 1 wherein A 1 and A 2 each independently represents linear or branched alkylene having 1-12 carbon atoms or linear or branched alkylene having 1-12 carbon atoms substituted by 1-4 branched alkyl substituents wherein said alkyl contains 1-10 carbon atoms.

Claim 11

Dependent Claim 136 words

The polymer of claim 1 wherein A 3 represents --B 1 --D--B 2 -- wherein D represents --N(R 10 )--(CO--D 1 ) y CO--N(R 11 )-- wherein D 1 represents linear or branched alkylene having 1-12 carbon atoms, linear or branched alkylene having 1-12 carbon atoms and having at least one branched alkyl substituent having 1-10 carbon atoms, linear or branched alkylene having 1-12 carbon atoms and being interrupted by a --S--S-- group or linear or branched alkylene having 1-12 carbon atoms and including an --NH-- or --O-- group at each end thereof, or D 1 represents arylene having 6-20 carbon atoms, arylene having 6-20 carbon atoms and being substituted by at least one allyl group having 1-3 carbon atoms or arylene having 6-20 carbon atoms and including an --NH-- or --O-- group at each end.

Claim 12

Dependent Claim 21 words

The polymer of claim 1 wherein D 2 represents --NH--alkylene--NH--, --O--alkylene--O-- or --S--alkylene-S- wherein the alkylene moiety has 1-12 carbon atoms.

Claim 13

Dependent Claim 93 words

The polymer of claim 1 wherein D 3 is linear or branched alkylene having 1-12 carbon atoms, linear or branched alkylene having 1-12 carbon atoms and having at least one branched alkyl substituent having 1-10 carbon atoms or linear or branched alkylene having 1-12 carbon atoms and having an --NH-- group at each end thereof or D 3 is arylene having 6-20 carbon atoms, arylene having 6-20 carbon atoms and being substituted by at least one alkyl group, or arylene having 6-20 carbon atoms and having an --NH-- group at each end thereof.

Claim 14

Dependent Claim 22 words

The polymer of claim 1 wherein D 3 represents cycloalkylene or --NH--cycloalkylene--NH-- wherein said cycloalkylene has from 5 to 20 carbon atoms.

Claim 15

Dependent Claim 20 words

The polymer of claim 8 wherein said ring contains a heteroatom selected from the group consisting of oxygen and sulfur.

Claim 16

Dependent Claim 84 words

A polymer having units of the formula ##STR30## wherein R 1 , R 2 , R 3 and R 4 each independently represent alkyl having up to 20 carbon atoms; A 1 and A 2 each independently represent alkylene containing up to 20 carbon atoms; X represents --CO--; R 5 and R 6 , together, represent ##STR31## wherein R 7 and R 8 represent hydrogen or lower alkyl, A 3 represents alkylene containing 2 to 20 carbon atoms, and Z - represents an anion.

Claim 17

Dependent Claim 84 words

A polymer having units of the formula ##STR30## wherein R 1 , R 2 , R 3 and R 4 each independently represent alkyl having up to 20 carbon atoms; A 1 and A 2 each independently represent alkylene containing up to 20 carbon atoms; X represents --CO--; R 5 and R 6 , together, represent ##STR31## wherein R 7 and R 8 represent hydrogen or lower alkyl, A 3 represents alkylene containing 2 to 20 carbon atoms, and Z - represents an anion.

Claim 18

Dependent Claim 60 words

The polymer of claim 15, wherein A 1 equals A 2 equals --(CH 2 ) 3 --; R 1 equals R 2 equals R 3 equals R 4 equals CH 3 ; R 5 and R 6 , together, represent --CH 2 --O--CH 2 --; A 3 equals --(CH 2 ) 6 -- and Z - equals Cl - .

Claim 19

Dependent Claim 218 words

A process for preparing the polymer of claim 1 comprising polycondensing at least one amine selected from the group consisting of an amine of the formula R 1 R 2 N--A 1 --N(R' 5 )--X--N(R' 6 )--A 2 --N--R 3 R 4 (II) wherein R' 5 and R' 6 have the meanings given for R 5 and R 6 in claim 39 or R' 5 and R' 6 also represent hydrogen when X represents --CO-- and an amine of the formula R 1 R 2 N--A 3 --NR 3 R 4 (III) with at least one dihalide selected from the group consisting of Z--A 3 --Z and Z--A 1 --N(R 5 )--X--N(R 6 )--A 2 --Z, wherein R 1 , R 2 , A 1 , X, A 2 , R 3 , R 4 , R 5 , R 6 and A 3 have the meanings given in claim 1, with the proviso that when R' 5 equals R'.sub. 6 equals H and X equals --CO--, the resulting intermediate polymer is reacted in the presence of an acid catalyst with an aldehyde having the formula R 7 --CHO wherein said aldehyde is present in an amount of two moles thereof per --NH--CO--NH-- group present in said intermediate polymer so as to produce the polymer of claim 1.

Claim 20

Dependent Claim 99 words

The process of claim 17 wherein said amine of formula II for which X represents --CO-- and R 5 and R 6 , together, represent --CH(R 7 )--O--CH(R 8 )-- is prepared by reacting at least one amine of the formula R 1 R 2 N--A 1 --NHCONH--A 2 --NR 3 R 4 with at least one aldehyde selected from the group consisting of R 7 CHO and R 8 CHO in an acid environment so as to form the salt of the resulting amine and thereafter transforming said salt into the free amine by reaction with a base.

Claim 21

Dependent Claim 93 words

The process of claim 17 wherein said amine of formula II for which X represents --SO 2 -- is prepared by reacting at least one amine selected from the group consisting of R 1 R 2 N--A 1 --NHR 5 and R 1 R 2 N--A 1 --NHR 6 with sulfuryl chloride wherein said amine is present in an amount of two moles thereof per mole of sulfuryl chloride so as to form the salt of the resulting amine and thereafter transforming said salt into the free amine by reaction with a base.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1986-07-25	1987-01-24	1987-07-26	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1990-07-25	1991-01-24	1991-07-26	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1994-07-25	1995-01-24	1995-07-26	$7700.00	Window Closed / Lapsed

Ionene polymer and preparation thereof

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