US 12,600,808 B2Granted

Crosslinkable prepolymers for chemically stable polymer gels

AssigneeOdne AG

InventorsMark Bispinghoff, Andreas Schmocker, Aaron Johnson

Life of this patent

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Abstract

The invention relates to water soluble crosslinkable prepolymers for the preparation of chemically stable crosslinked polymer gels, a process for preparing the same, compositions containing the same and their use such as a medical or dental filler composition.

Claims17

Dependent claims

A process for preparing a chemically stable crosslinked dental polymer gel composition, said process comprising the steps of:

a) dissolving either:
i) a water soluble crosslinkable dental prepolymer for the preparation of chemically stable crosslinked polymer gels, said water soluble crosslinkable prepolymer having the formula I:
R1-L-B-L-R2 (I)
where:
B is a backbone selected from the group consisting of:
Poly(ethylene glycol) (PEG):
with n comprising between 1 to 450 repeating units,
Oligo(ethylene glycol) (EG):
with m comprising between 1 to 12 repeating units,
Poloxamer:
where p, q, s are independent from each other and comprise between 1 to 200 repeating units,
Inverse Poloxamer:
where x, y, z are independent from each other and comprise between 1 to 200 repeating units;
L is a linker selected among C3 to C18 linear or branched alkyl chains;
R1 and R2 are endgroups with R1 being equal or different from R2, where R1and R2 are selected from the group consisting of:
H, OH;
acrylate;
methacrylate;
acrylamide;
methacrylamide;
but-3-en-2-one;
inverse methacrylate of formula
where R is an alkyl, X═O, NH;
vinylsulfone;
vinylurea;
vinylcarbonate;
vinylcarbamate;
vinylthioester;
vinylthiourea;
with the proviso that R2is not H or OH when R1is H or OH;
and with the proviso that when L=C3, then endgroups R1 and R2 are not acrylamide;
or
ii) a water soluble crosslinkable dental prepolymer for the preparation of chemically stable crosslinked polymer gels, said water soluble crosslinkable prepolymer having the formula II:
R1-B-R2 (II)
where:
B is a backbone consisting of:
Inverse Poloxamer:
where x, y, z are independent from each other and comprise between 1 to 200 repeating units;
R1 and R2 are endgroups with R1 being equal or different from R2, where
R1 and R2 are selected from the group consisting of:
H, OH;
acrylate;
methacrylate;
acrylamide;
methacrylamide;
but-3-en-2-one;
inverse methacrylate of formula
where R is an alkyl, X═O, NH;
vinylsulfone;
vinylurea;
vinylcarbonate;
vinylcarbamate;
vinylthioester;
vinylthiourea;
with the proviso that R2 is not H or OH when R1 is H or OH,
in a suitable solvent;
b) adding phenolic or aminoxyl radical stabilizers;
c) adding a radical polymerization initiator;
d) applying a polymerization or crosslinking step to form said chemically stable crosslinked dental polymer gel composition.

56 more elements

A precursor composition of a chemically stable crosslinked dental polymer gel composition, wherein said precursor composition comprises between 5-95% in weight of either:

i) a stable water soluble dental crosslinkable prepolymer for the preparation of chemically stable crosslinked polymer gels, said water soluble crosslinkable prepolymer having the formula I:
R1-L-B-L-R2 (I)
where:
B is a backbone selected from the group consisting of:
Poly(ethylene glycol) (PEG):
with n comprising between 1 to 450 repeating units,
Oligo(ethylene glycol) (EG):
with m comprising between 1 to 12 repeating units,
Poloxamer:
where p, q, s are independent from each other and comprise between 1 to 200 repeating units,
Inverse Poloxamer:
where x, y, z are independent from each other and comprise between 1 to 200 repeating units;
L is a linker selected among C3 to C18 linear or branched alkyl chains;
R1 and R2 are endgroups with R1 being equal or different from R2, where R1 and R2 are selected from the group consisting of:
H, OH;
acrylate;
methacrylate;
acrylamide;
methacrylamide;
but-3-en-2-one;
inverse methacrylate of formula
where R is an alkyl, X═O, NH;
vinylsulfone;
vinylurea;
vinylcarbonate;
vinylcarbamate;
vinylthioester;
vinylthiourea;
with the proviso that R2 is not H or OH when R1 is H or OH;
and with the proviso that when L=C3 then endgroups R1 and R2 are not acrylamide;
or
ii) a water soluble crosslinkable dental prepolymer for the preparation of chemically stable crosslinked polymer gels, said water soluble crosslinkable prepolymer having the formula II:
R1-B-R2 (II)
where:
B is a backbone consisting of:
Inverse Poloxamer:
where x, y, z are independent from each other and comprise between 1 to 200 repeating units;
R1 and R2 are endgroups with R1 being equal or different from R2, where R1 and R2 are selected from the group consisting of:
H, OH;
acrylate;
methacrylate;
acrylamide;
methacrylamide;
but-3-en-2-one;
inverse methacrylate of formula
where R is an alkyl, X═O, NH;
vinylsulfone;
vinylurea;
vinylcarbonate;
vinylcarbamate;
vinylthioester;
vinylthiourea;
with the proviso that R2 is not H or OH when R1 is H or OH,
between 5-95% in weight of a suitable solvent, between 0.001-10% in weight of phenolic or aminoxyl radical stabilizers and between 0.001-10% in weight of a radical polymerization initiator.

51 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/922,524Filed 11 May 2021
Priority: EP 2017758629 May 2020
Published: US 2023/0167209 A11 Jun 2023
Granted: 14 Apr 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification16 codes

A61K 31/77
Polymers containing oxygen: of oxiranes
C08F 122/1006
Esters: of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
A61K 6/887
Comprising natural or synthetic resins: compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
A61L 27/18
Macromolecular materials: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Family

US 2023/0167209 A1Pre-grant publication · published 1 Jun 2023
US 12,600,808 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A process for preparing a chemically stable crosslinked dental polymer gel composition, said process comprising the steps of:

a) dissolving either:
i) a water soluble crosslinkable dental prepolymer for the preparation of chemically stable crosslinked polymer gels, said water soluble crosslinkable prepolymer having the formula I:
R1-L-B-L-R2 (I)
where:
B is a backbone selected from the group consisting of:
Poly(ethylene glycol) (PEG):
with n comprising between 1 to 450 repeating units,
Oligo(ethylene glycol) (EG):
with m comprising between 1 to 12 repeating units,
Poloxamer:
where p, q, s are independent from each other and comprise between 1 to 200 repeating units,
Inverse Poloxamer:
where x, y, z are independent from each other and comprise between 1 to 200 repeating units;
L is a linker selected among C3 to C18 linear or branched alkyl chains;
R1 and R2 are endgroups with R1 being equal or different from R2, where R1and R2 are selected from the group consisting of:
H, OH;
acrylate;
methacrylate;
acrylamide;
methacrylamide;
but-3-en-2-one;
inverse methacrylate of formula
where R is an alkyl, X═O, NH;
vinylsulfone;
vinylurea;
vinylcarbonate;
vinylcarbamate;
vinylthioester;
vinylthiourea;
with the proviso that R2is not H or OH when R1is H or OH;
and with the proviso that when L=C3, then endgroups R1 and R2 are not acrylamide;
or
ii) a water soluble crosslinkable dental prepolymer for the preparation of chemically stable crosslinked polymer gels, said water soluble crosslinkable prepolymer having the formula II:
R1-B-R2 (II)
where:
B is a backbone consisting of:
Inverse Poloxamer:
where x, y, z are independent from each other and comprise between 1 to 200 repeating units;
R1 and R2 are endgroups with R1 being equal or different from R2, where
R1 and R2 are selected from the group consisting of:
H, OH;
acrylate;
methacrylate;
acrylamide;
methacrylamide;
but-3-en-2-one;
inverse methacrylate of formula
where R is an alkyl, X═O, NH;
vinylsulfone;
vinylurea;
vinylcarbonate;
vinylcarbamate;
vinylthioester;
vinylthiourea;
with the proviso that R2 is not H or OH when R1 is H or OH,
in a suitable solvent;
b) adding phenolic or aminoxyl radical stabilizers;
c) adding a radical polymerization initiator;
d) applying a polymerization or crosslinking step to form said chemically stable crosslinked dental polymer gel composition.

56 more elements

Facts

Application

17/922,524Filed 11 May 2021

Priority

EP 2017758629 May 2020

Published

US 2023/0167209 A11 Jun 2023

Granted

14 Apr 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification16 codes

A61K 31/77
Polymers containing oxygen: of oxiranes
C08F 122/1006
Esters: of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
A61K 6/887
Comprising natural or synthetic resins: compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
A61L 27/18
Macromolecular materials: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds