IP Library Granted Patent US 11,766,386
Granted Patent B2
US 11,766,386 · App. 16/347,306 · Granted Sep 26, 2023

Medical composition containing guanidinyl-containing polymer(s) and carrageenane(s)

Inventors: Henning Hoffmann (Windach, DE); Peter U. Osswald (Tuerkheim, DE)
Assignee: 3M INNOVATIVE PROPERTIES COMPANY
A61K6/18A61K6/52A61K6/69A61K6/76A61L15/08A61L15/125A61L15/14A61L15/18A61L15/225A61L15/28A61L15/60A61C5/70C08K3/36C08L5/00C08L79/00C08L2203/02
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Quick Facts
Patent No.
US 11,766,386
App. No.
16/347,306
Granted
Sep 26, 2023
Kind
B2
Abstract

The invention relates to a medical composition comprising guanidinyl-containing polymer(s) and polyanionic polymer(s). The medical composition is useful for absorbing water-containing fluids and can be used as dental retraction composition or as part of a medical treatment device.

Claims (70)

1. A medical composition comprising:

a guanidinyl-containing polymer,

a carrageenan selected from iota carrageenan and lambda carrageenan, and

optionally water, if present, in an amount no more than 2 wt % with respect to the weight of the medical composition,

wherein the medical composition is water absorbing.

2. The medical composition of claim 1 , the guanidinyl-containing polymer being:

a polymer having at least one pendant guanidinyl group characterized by the following formula:

—[C(R 1 )═N—R 2 ] n -N(R 3 )—[C(═N(R 4 ))—N(R 4 )] m -R 5 ,

wherein:

R 1 is hydrogen, C 1 -C 12 (hetero)alkyl, or a C 5 -C 12 (hetero)aryl,

R 2 is a covalent bond, a C 2 to C 12 (hetero)alkylene, or a C 5 -C 12 (hetero)arylene,

R 3 is hydrogen, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl,

each R 4 is independently hydrogen, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl,

R 5 is hydrogen, C 1 -C 12 (hetero)alkyl, C 5 -C 12 (hetero)aryl, or —N(R 4 ) 2 ,

n is 0 or 1, and

m is 1 or 2.

3. The medical composition of claim 1 , the guanidinyl-containing polymer(s) being:

a polymer having at least one pendent guanidinyl group of the following formula:

wherein:

m is equal to 1 or 2,

R 3 is hydrogen, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl,

each R4 is independently hydrogen, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl, and

R 5 is hydrogen, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl, or —N(R 4 ) 2 ; or

a polymer having at least one pendent guanidinyl group of the following formula:

—N(R 3 )—[C(═N + (H)(R 4 ))—N(R 4 )] m -R 5 X − ,

wherein:

m is equal to 1 or 2,

R 3 is hydrogen, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl,

each R 4 is independently hydrogen, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl,

R 5 is hydrogen, C 1 -C 12 (hetero)alkyl, or C 5 -C 12 (hetero)aryl, or —N(R 4 ) 2 , and

X − is selected from Cl − , Br − , I − , ½ SO 4 2− , NO 3 − , CH 3 COO − , C 3 H 7 COO − .

4. The medical composition of claim 1 , the guanidinyl-containing polymer is derived from polyvinylamine, poly(N-methylvinylamine), polyallylamine, polyallylmethylamine, polydiallylamine, poly(-aminomethylstyrene), poly(-aminostyrene), poly(acrylamide-co-methylaminopropylacrylamide), poly(acrylamide-co-aminoethyl-methacrylate), polyethylenimine, polypropylenimine, polylysine, polyaminoamides, polydimethylamine-epichlorohydrin-ethylenediamine, polyaminosiloxanes, dendrimers formed from polyamidoamine and polypropylenimine, biopolymers, polyacrylamide homopolymers, polyacrylamide copolymers, amino-containing polyacrylate homopolymers, or amino-containing polyacrylate copolymers.

5. The medical composition of claim 1 , further comprising a filler and a paste forming liquid.

6. The medical composition of claim 5 , the filler being selected from silicates, silicas, aluminas, magnesias, titanias, inorganic salts, metallic oxides, glasses, plastic powder, microcrystalline cellulose, nanocrystalline cellulose, starch, and a combination thereof.

7. The medical composition of claim 5 , the paste forming liquid being characterized by one or more of the following features:

molecular weight: 200 to 10,000 g/mol;

boiling point: above 100° C.; and

viscosity: up to 35 Pa*s at 23° C.

8. The medical composition of claim 5 , being characterized as follows:

the filler selected from one or more phyllosilicate and being present in an amount from 20 to 70 wt. %;

the paste forming liquid selected from glycol, glycerine, ethylene glycol, poly(ethylene glycol), propylene glycol, poly(propylene glycol), copolymer(s) of ethylene glycol, propylene glycol, tetrahydrofuran and a combination thereof and being present in an amount from 10 to 60 wt. %;

the guanidinyl-containing polymer being a polyethylene imine and being present in an amount from 1 to 60 wt. %;

the carrageenane being present in an amount from 1 to 30 wt. %; and

the medical composition not comprising one or more of:

aluminum chloride in an amount above 5 wt. %, and

water in an amount above 2 wt. %,

wherein wt. % amounts are with respect to the weight of the whole composition.

9. The medical composition of claim 1 , comprising the components in following amounts:

a filler(: from 3 to 70 wt. %,

a paste forming liquid: from 10 to 60 wt. %,

the guanidinyl-containing polymer: from 1 to 60 wt. %, and

the carrageenane: from 1 to 40 wt. %,

wherein wt. % amounts are with respect to the weight of the whole composition.

10. The medical composition of claim 1 , being contained in a delivery device, the delivery device having the shape of a capsule, compule, syringe, or cartridge.

11. The medical composition of claim 1 , for use as a dental retraction material.

12. A kit of parts comprising:

the medical composition of claim 1 , and either of the following alone or in combination:

instruction for use;

dental impression material(s);

applier(s);

retraction cap(s).

13. A medical treatment device comprising the medical composition of claim 1 .

14. The medical treatment device of claim 13 having the shape of a tape, fixture, wound dressing, bandage, or combination thereof.

15. A method for enhancing the water uptake capability of a medical composition, the method comprising incorporating the medical composition of claim 1 into a medical composition.

16. A method for retracting soft tissue from hard dental tissue, the method comprising:

dispensing a medical composition of claim 1 into a sulcus between the soft tissue and the hard dental tissue;

allowing the medical composition to remain in the sulcus for a period of at least 10 s; and

removing the medical composition from the sulcus.

17. The method of claim 16 , further comprising taking an impression of the hard dental tissue with an impression material after the removing of the medical composition from the sulcus.

18. The method of claim 16 , further comprising taking an impression of the hard dental tissue via an intra-oral scan using an inter-oral scanner after the removing of the medical composition from the sulcus.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: 3M INNOVATIVE PROPERTIES COMPANY
To: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY
Reel/Frame 066430/0295 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2019
From: HOFFMANN, HENNING; OSSWALD, PETER U.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 049885/0044 →