US4496708A — Water-soluble polyurethane comb polymer production

Claim 1

Independent Claim 164 words

A comb polymer comprising a water-soluble polyurethane containing the repeating units: --X.sub.a' --, --Y.sub.b -- and --(--X--).sub.m --Z.sub.c -- wherein: X is the residue of an organic polyisocyanate; Y is the residue of a polyethylene glycol homopolymer or copolymer with up to 50 mole percent C 3 to C 5 polyoxyalkylene, or the monomeric equivalent of said polyethylene glycol; Z is the residue of a hydrophobe reactant containing a monovalent hydrophobic group providing a molar volume contribution of at least about 130 cc/mole; b is at least about 2; c is at least about 2; m is 0 or 1; a' is such that ##EQU5## is between about 0.50 to about 1.25 and sufficient to provide a polymer molecular weight of at least about 10,000; and wherein: (1) the polymer has at least one Z unit separated from each end of the polymer by at least one X unit; and (2) the hydrophilic/lipophilic balance of the polymer is between about 14 to about 19.5.

Claim 2

Dependent Claim 164 words

A comb polymer comprising a water-soluble polyurethane containing the repeating units: --X.sub.a' --, --Y.sub.b -- and --(--X--).sub.m --Z.sub.c -- wherein: X is the residue of an organic polyisocyanate; Y is the residue of a polyethylene glycol homopolymer or copolymer with up to 50 mole percent C 3 to C 5 polyoxyalkylene, or the monomeric equivalent of said polyethylene glycol; Z is the residue of a hydrophobe reactant containing a monovalent hydrophobic group providing a molar volume contribution of at least about 130 cc/mole; b is at least about 2; c is at least about 2; m is 0 or 1; a' is such that ##EQU5## is between about 0.50 to about 1.25 and sufficient to provide a polymer molecular weight of at least about 10,000; and wherein: (1) the polymer has at least one Z unit separated from each end of the polymer by at least one X unit; and (2) the hydrophilic/lipophilic balance of the polymer is between about 14 to about 19.5.

Claim 3

Dependent Claim 22 words

The polymer of claim 1 wherein said polyisocyanate has the structure: O═C═N--R.sub.1 --N═C═O wherein R 1 is an alkylene, cycloalkylene or arylene.

Claim 4

Dependent Claim 17 words

The polymer of claim 2 wherein said polyisocyanate is toluene diisocyanate, methylene dianiline diisocyanate or isophorone diisocyanate.

Claim 5

Dependent Claim 21 words

The polymer of claim 1 wherein said polyethylene glycol is a homopolymer having a molecular weight of up to about 14,000.

Claim 6

Dependent Claim 21 words

The polymer of claim 1 wherein the molar volume contribution of said monovalent hydrophobic group is at least about 190 cc/mole.

Claim 7

Dependent Claim 24 words

The polymer of claim 1 wherein said monovalent hydrophobic group is an unsubstituted or halo substituted hydrocarbon radical having at least 8 carbon atoms.

Claim 8

Dependent Claim 15 words

The polymer of claim 6 wherein said hydrocarbon radical has at least 12 carbon atoms.

Claim 9

Dependent Claim 23 words

The polymer of claim 7 wherein said hydrocarbon radical is an alkyl or aralkyl having from about 14 to about 16 carbon atoms.

Claim 10

Dependent Claim 15 words

The polymer of claim 8 wherein the said hydrocarbon radical is nonylphenyl, n-tetradecyl or n-hexadecyl.

Claim 11

Dependent Claim 12 words

The polymer of claim 1 wherein said polyurethane has terminal hydroxyl groups.

Claim 12

Dependent Claim 41 words

The polymer of claim 1 wherein m is 1 and said polyurethane has the formula: HO[(Y--X).sub.b' Z--X].sub.c Y--OH wherein b' is the average number of polyethylene glycol residues per hydrophobe residue; and c, X, Y and Z are as defined previously.

Claim 13

Dependent Claim 65 words

The polymer of claim 1 wherein m is 0 and said polyurethane has the formula: HO[(Y.sub.1 Z.sub.c' Y.sub.2).sub.b-1 X].sub.a Y--OH wherein a, b, X and Z are as defined previously c' is the average number of monovalent hydrophobic group per polyethylene glycol repeating unit; and Y 1 and Y 2 are the residues of said polyethylene glycol or monomeric equivalent reacted with said hydrophobe reactant.

Claim 14

Dependent Claim 14 words

An aqueous solution containing an effective thickening amount of the polymer of claim 1.

Claim 15

Dependent Claim 158 words

A process for producing a comb polymer which is a water-soluble polyurethane, which comprises reacting: (a) a moles of an organic polyisocyanate; (b) b moles of a polyethylene glycol homopolymer or copolymer with up to 50 mole percent C 3 to C 5 polyoxyalkylene or the monomeric equivalent of said polyethylene glycol; and (c) c moles of a hydrophobe reactant containing a monovalent hydrophobic group providing a molar volume contribution of at least about 130 cc/mole wherein: b is at least about 2; c is at least about 2; and a is such that ##EQU6## is between about 0.50 to about 1.25 and sufficient to provide a polymer molecular weight of at least about 10,000; (d) in a manner sufficient to produce said polymer with (1) at least one monovalent hydrophobic group separated from each end of the polymer by at least one polyethylene glycol residue, and (2) a hydrophilic/lipophilic balance of between about 14 to about 19.5.

Claim 16

Dependent Claim 158 words

A process for producing a comb polymer which is a water-soluble polyurethane, which comprises reacting: (a) a moles of an organic polyisocyanate; (b) b moles of a polyethylene glycol homopolymer or copolymer with up to 50 mole percent C 3 to C 5 polyoxyalkylene or the monomeric equivalent of said polyethylene glycol; and (c) c moles of a hydrophobe reactant containing a monovalent hydrophobic group providing a molar volume contribution of at least about 130 cc/mole wherein: b is at least about 2; c is at least about 2; and a is such that ##EQU6## is between about 0.50 to about 1.25 and sufficient to provide a polymer molecular weight of at least about 10,000; (d) in a manner sufficient to produce said polymer with (1) at least one monovalent hydrophobic group separated from each end of the polymer by at least one polyethylene glycol residue, and (2) a hydrophilic/lipophilic balance of between about 14 to about 19.5.

Claim 17

Dependent Claim 17 words

The process of claim 14 wherein said organic polyisocyanate, polyethylene glycol and hydrophobe reactant are reacted simultaneously.

Claim 18

Dependent Claim 54 words

The process of claim 14 wherein said hydrophobe reactant has the formula: ##STR16## wherein; n is from 0 to about 40; R 2 is said monovalent hydrophobic group; each R 3 is individually hydrogen or C 1 to C 3 alkyl; and Q is a functional group reactive with said polyisocyanate or polyethylene glycol.

Claim 19

Dependent Claim 9 words

The process of claim 16 wherein n is 0.

Claim 20

Dependent Claim 15 words

The process of claim 16 wherein Q is an alkylene glycol radical or alkenyl radical.

Claim 21

Dependent Claim 9 words

The process of claim 18 wherein Q is ##STR17##

Claim 22

Dependent Claim 11 words

The process of claim 18 wherein Q is --CH═CH 2 .

Claim 23

Dependent Claim 97 words

The process of claim 19 which comprises: (1) reacting a molar excess of said polyisocyanate with said polyethylene glycol to produce a polyethylene glycol diisocyanate intermediate having the formula O═C═N--X--Y--X).sub.b' N═C═O wherein b' is the average number of polyethylene glycol residues per molecule, X is the residue of said polyisocyanate and Y is the residue of said polyethylene glycol; followed by (2) reacting said polyethylene glycol intermediate with said hydrophobe reactant to produce said polyurethane having the repeating structure: ##STR18## wherein b', c, n, R 2 , R 3 , X and Y are as defined previously.

Claim 24

Dependent Claim 72 words

The process of claim 19 which comprises: (1) reacting a molar excess of said polyisocyanate with said hydrophobe reactant to produce a hydrophobe diisocyanate intermediate having the formula: ##STR19## wherein: n, R 2 and R 3 are as defined previously; and X is the residue of said polyisocyanate; followed by (2) reacting said hydrophobe diisocyanate intermediate with said polyethylene glycol to produce said polyurethane having the repeating structure as in claim 21.

Claim 25

Dependent Claim 138 words

The process of claim 19 which comprises: (1) reacting said hydrophobic reactant with (a) said polyethylene glycol or (b) its monomeric equivalent comprised of sufficient moles of at least one oxyalkylene glycol of the formula: ##STR20## wherein R 4 is hydrogen or C 1 to C 3 alkyl, to produce b moles a diol intermediate having the formula: ##STR21## wherein: c' is the average number of monovalent hydrophobic groups per diol intermediate; n, R 2 and R 3 are as defined previously; and Y 3 and Y 4 are the residue of said polyethylene glycol or oxyalkylene reaction; followed by (2) reacting said diol intermediate with said polyisocyanate to produce said polyurethane having the repeating structure ##STR22## wherein a, b, c', n, R 2 , R 3 , X, Y 3 and Y 4 are as defined previously.

Claim 26

Dependent Claim 93 words

The process of claim 20 which comprises: (1) grafting said hydrophobe reactant onto said polyethylene glycol to produce a diol intermediate having the formula: ##STR23## wherein: R 2 is as defined previously; c' is the average number of grafts containing said monovalent hydrophobic group; and Y 5 and Y 6 are the residue of the polyethylene glycol; followed by (2) reacting said diol intermediate with said polyisocyanate to produce said polyurethane having the repeating structure ##STR24## wherein a, b, c', R 2 , X, Y 5 and Y 6 are as defined previously.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1988-01-29	1988-07-30	1989-01-29	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1992-01-29	1992-07-30	1993-01-29	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1996-01-29	1996-07-30	1997-01-29	$7700.00	Window Closed / Lapsed

Water-soluble polyurethane comb polymer production

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