Dental polyfunctional monomers and dental hydroxyl group-containing monomers

A dental material comprising a dental polyfunctional monomer which is a product of reaction of a compound represented by general formula (1A), in which a core (X) and a terminal group (Y1A) are bonded to each other directly or via a linking group (Z), with a (meth)acryloyl group-containing isocyanate compound represented by general formula (3):

• X(Y1A)n1aA(Z—Y1A)n1bA (1A)
• wherein in the general formula (1A), n1aA represents a number of terminal groups (Y1A) directly bonded to the core (X), n1bA represents a number of terminal groups (Y1A) bonded to the core (X) via the linking group (Z), and a sum of n1aA and n1bA is equal to a valence of the core (X), provided that n1bA is not 0;
• the core (X) is a C1-200 polyvalent organic group having a valence of not less than 3 containing at least three oxygen atoms, or nitrogen atoms, or a mixture thereof, in which each atom bonded to the terminal group (Y1A) or the linking group (Z) is an oxygen or nitrogen atom;
• the terminal group (Y1A) is a (meth)acryloyl group, a C1-20 monovalent hydrocarbon group or an active hydrogen atom, and a plurality of the terminal groups (Y1A) may be the same as or different from each other, with the proviso that among the terminal groups (Y1A) in the compound represented by the general formula (1A), three or more of the terminal groups are active hydrogen atoms or (meth)acryloyl groups, and one or more of the terminal groups are active hydrogen atoms;
• and
• the linking group (Z) is a divalent group represented by general formula (2), and when the compound represented by the general formula (1A) contains a plurality of the linking groups (Z), the linking groups (Z) may be the same as or different from each other;
• wherein in the general formula (2), n2a, n2b, n2c and n2d represent unit numbers of respective repeating units, and are each 0 to 100, a sum of n2a, n2b, n2c and n2d is 1 to 100, a left end of the group is bonded to the core (X), and a right end of the group is bonded to the terminal group (Y1A);
• and
• wherein in the general formula (3), R3a represents a hydrogen atom or a methyl group, R3b represents a C2-6 linear alkylene group or a C2-6 linear oxyalkylene group, and the linear alkylene group or the linear oxyalkylene group is optionally substituted with a C1-6 alkyl group and/or a (meth)acryloyloxymethylene group in place of a hydrogen atom,
• under a condition of (total equivalents/moles of isocyanate groups present in the reaction derived from the compound represented by the general formula (3))/(total equivalents/moles of active hydrogen atoms of (Y1A) bonded to terminal oxygen atoms and nitrogen atoms of the core (X) present in the compound represented by general formula (1A))=1,
• wherein the compound (1A) is at least one selected from the group consisting of compounds represented by general formulas (6′a) to (6′k):
• wherein n6′i-a, n6′j-a and n6′k-a in the general formulas (6′i), (6′j) and (6′k) each represent a number of arms of a polyol bonded to the core X, and are each an integer of not less than 3;
• and
• n6′i-b and n6′j-b in the general formulas (6′i) and (6′j) represent numbers of oxyethylene units and oxypropylene units, respectively, and are each in the range of 1 to 100, the numbers of units for respective arms may be the same as or different from each other, n6′k-b and n6′k-c in the general formula (6′k) represent numbers of oxyethylene units and oxypropylene units, respectively, a sum thereof is in the range of 1 to 100, and the sums of the numbers of units for respective arms may be the same as or different from each other,
• wherein the dental material further comprises at least one filler selected from the group consisting of glasses, calcium fluoride, ytterbium fluoride, calcium phosphate, barium sulfate, zirconium dioxide, titanium dioxide and hydroxyapatite.

A dental treatment method comprising a step of curing in a mouth of a patient in need thereof a dental material composition that comprises a dental polyfunctional monomer, a polymerization initiator, and at least one filler selected from the group consisting of glasses, calcium fluoride, ytterbium fluoride, calcium phosphate, barium sulfate, zirconium dioxide, titanium dioxide and hydroxyapatite,

• wherein the dental polyfunctional monomer is represented by general formula (8A), in which a core (X) and a terminal group (Y2A) are bonded to each other directly or via a linking group (Z):
• X(Y2A)n8aA(Z—Y2A)n8bA (8A)
• wherein in the general formula (8A), n8aA represents a number of terminal groups (Y2A) directly bonded to the core (X), n8bA represents a number of terminal groups (Y2A) bonded to the core (X) via the linking group (Z), and a sum of n8aA and n8bA is equal to a valence of the core (X), provided that n8bA is not 0;
• the terminal group (Y2A) is a (meth)acryloyl group-containing group (Y3) represented by general formula (9), a (meth)acryloyl group or a C1-20 hydrocarbon group, and a plurality of the terminal groups (Y2A) may be the same as or different from each other, with the proviso that among all the terminal groups (Y2A) in the compound represented by the general formula (8A), three or more of the terminal groups are (meth)acryloyl group-containing groups (Y3) or (meth)acryloyl groups, and one or more of the terminal groups are (meth)acryloyl group-containing groups (Y3);
• and
• the linking group (Z) is a divalent group represented by general formula (2), and when the compound represented by the general formula (8A) contains a plurality of the linking groups (Z), the linking groups (Z) may be the same as or different from each other;
• wherein in the general formula (9), R9a represents a hydrogen atom or a methyl group, R9b represents a C2-6 linear alkylene group or a C2-6 linear oxyalkylene group, and the linear alkylene group or the linear oxyalkylene group is optionally substituted with a C1-6 alkyl group and/or a (meth)acryloyloxymethylene group in place of a hydrogen atom;
• and
• wherein in the general formula (2), n2a, n2b, n2c and n2d represent unit numbers of respective repeating units, and are each 0 to 100, a sum of n2a, n2b, n2c and n2d is 1 to 100, a left end of the group is bonded to the core (X), and a right end of the group is bonded to the terminal group (Y2A),
• wherein the core (X) is at least one selected from the group consisting of groups represented by general formulas (6a) to (6j):

A dental treatment method comprising a step of curing outside a mouth of a patient in need thereof a dental material composition that comprises a dental polyfunctional monomer, a polymerization initiator, and at least one filler selected from the group consisting of glasses, calcium fluoride, ytterbium fluoride, calcium phosphate, barium sulfate, zirconium dioxide, titanium dioxide and hydroxyapatite, to obtain a cured product, and a step of applying the cured product into the mouth,

• wherein the dental polyfunctional monomer is represented by general formula (8A), in which a core (X) and a terminal group (Y2A) are bonded to each other directly or via a linking group (Z):
• X(Y2A)n8aA(Z—Y2A)n8bA (8A)
• wherein in the general formula (8A), n8aA represents a number of terminal groups (Y2A) directly bonded to the core (X), n8bA represents a number of terminal groups (Y2A) bonded to the core (X) via the linking group (Z), and a sum of n8aA and n8bA is equal to a valence of the core (X), provided that n8bA is not 0;
• the terminal group (Y2A) is a (meth)acryloyl group-containing group (Y3) represented by general formula (9), a (meth)acryloyl group or a C1-20 hydrocarbon group, and a plurality of the terminal groups (Y2A) may be the same as or different from each other, with the proviso that among all the terminal groups (Y2A) in the compound represented by the general formula (8A), three or more of the terminal groups are (meth)acryloyl group-containing groups (Y3) or (meth)acryloyl groups, and one or more of the terminal groups are (meth)acryloyl group-containing groups (Y3);
• and
• the linking group (Z) is a divalent group represented by general formula (2), and when the compound represented by the general formula (8A) contains a plurality of the linking groups (Z), the linking groups (Z) may be the same as or different from each other;
• wherein in the general formula (9), R9a represents a hydrogen atom or a methyl group, R9b represents a C2-6 linear alkylene group or a C2-6 linear oxyalkylene group, and the linear alkylene group or the linear oxyalkylene group is optionally substituted with a C1-6 alkyl group and/or a (meth)acryloyloxymethylene group in place of a hydrogen atom;
• and
• wherein in the general formula (2), n2a, n2b, n2c and n2d represent unit numbers of respective repeating units, and are each 0 to 100, a sum of n2a, n2b, n2c and n2d is 1 to 100, a left end of the group is bonded to the core (X), and a right end of the group is bonded to the terminal group (Y2A),
• wherein the core (X) is at least one selected from the group consisting of groups represented by general formulas (6a) to (6j):

A dental treatment method comprising a step of curing in a mouth of a patient in need thereof a dental material composition that comprises a dental polyfunctional monomer, a polymerization initiator, and at least one filler selected from the group consisting of glasses, calcium fluoride, ytterbium fluoride, calcium phosphate, barium sulfate, zirconium dioxide, titanium dioxide and hydroxyapatite,

• wherein the dental polyfunctional monomer is a product of reaction of a compound represented by general formula (1A), in which a core (X) and a terminal group (Y1A) are bonded to each other directly or via a linking group (Z), with a (meth)acryloyl group-containing isocyanate compound represented by general formula (3):
• X(Y1A)n1aA(Z—Y1A)n1bA (1 A)
• wherein in the general formula (1A), n1aA represents a number of terminal groups (Y1A) directly bonded to the core (X), n1bA represents a number of terminal groups (Y1A) bonded to the core (X) via the linking group (Z), and a sum of n1aA and n1bA is equal to a valence of the core (X), provided that n1bA is not 0;
• the core (X) is a C1-200 polyvalent organic group having a valence of not less than 3 containing at least three oxygen atoms, or nitrogen atoms, or a mixture thereof, in which each atom bonded to the terminal group (Y1A) or the linking group (Z) is an oxygen or nitrogen atom;
• the terminal group (Y1A) is a (meth)acryloyl group, a C1-20 monovalent hydrocarbon group or an active hydrogen atom, and a plurality of the terminal groups (Y1A) may be the same as or different from each other, with the proviso that among the terminal groups (Y1A) in the compound represented by the general formula (1A), three or more of the terminal groups are active hydrogen atoms or (meth)acryloyl groups, and one or more of the terminal groups are active hydrogen atoms;
• and
• the linking group (Z) is a divalent group represented by general formula (2), and when the compound represented by the general formula (1A) contains a plurality of the linking groups (Z), the linking groups (Z) may be the same as or different from each other;
• wherein in the general formula (2), n2a, n2b, n2c and n2d represent unit numbers of respective repeating units, and are each 0 to 100, a sum of n2a, n2b, n2c and n2d is 1 to 100, a left end of the group is bonded to the core (X), and a right end of the group is bonded to the terminal group (Y1A);
• and
• wherein in the general formula (3), R3a represents a hydrogen atom or a methyl group, R3b represents a C2-6 linear alkylene group or a C2-6 linear oxyalkylene group, and the linear alkylene group or the linear oxyalkylene group is optionally substituted with a C1-6 alkyl group and/or a (meth)acryloyloxymethylene group in place of a hydrogen atom,
• under a condition of (total equivalents/moles of isocyanate groups present in the reaction derived from the compound represented by the general formula (3))/(total equivalents/moles of active hydrogen atoms of (Y1A) bonded to terminal oxygen atoms and nitrogen atoms of the core (X) present in the compound represented by general formula (1A))=1,
• wherein the compound (1A) is at least one selected from the group consisting of compounds represented by general formulas (6′a) to (6′k):
• wherein n6′i-a, n6′j-a and n6′k-a in the general formulas (6′i), (6′j) and (6′k) each represent a number of arms of a polyol bonded to the core X, and are each an integer of not less than 3;
• and
• n6′i-b and n6′j-b in the general formulas (6′i) and (6′j) represent numbers of oxyethylene units and oxypropylene units, respectively, and are each in the range of 1 to 100, the numbers of units for respective arms may be the same as or different from each other, n6′k-b and n6′k-c in the general formula (6′k) represent numbers of oxyethylene units and oxypropylene units, respectively, a sum thereof is in the range of 1 to 100, and the sums of the numbers of units for respective arms may be the same as or different from each other.

A dental treatment method comprising a step of curing outside a mouth of a patient in need thereof a dental material composition that comprises a dental polyfunctional monomer, a polymerization initiator, and at least one filler selected from the group consisting of glasses, calcium fluoride, ytterbium fluoride, calcium phosphate, barium sulfate, zirconium dioxide, titanium dioxide and hydroxyapatite, to obtain a cured product, and a step of applying the cured product into the mouth,

• wherein the dental polyfunctional monomer is a product of reaction of a compound represented by general formula (1A), in which a core (X) and a terminal group (Y1A) are bonded to each other directly or via a linking group (Z), with a (meth)acryloyl group-containing isocyanate compound represented by general formula (3):
• X(Y1A)n1aA(Z—Y1A)n1bA (1 A)
• wherein in the general formula (1A), n1aA represents a number of terminal groups (Y1A) directly bonded to the core (X), n1bA represents a number of terminal groups (Y1A) bonded to the core (X) via the linking group (Z), and a sum of n1aA and n1bA is equal to a valence of the core (X), provided that n1bA is not 0;
• the core (X) is a C1-200 polyvalent organic group having a valence of not less than 3 containing at least three oxygen atoms, or nitrogen atoms, or a mixture thereof, in which each atom bonded to the terminal group (Y1A) or the linking group (Z) is an oxygen or nitrogen atom;
• the terminal group (Y1A) is a (meth)acryloyl group, a C1-20 monovalent hydrocarbon group or an active hydrogen atom, and a plurality of the terminal groups (Y1A) may be the same as or different from each other, with the proviso that among the terminal groups (Y1A) in the compound represented by the general formula (1A), three or more of the terminal groups are active hydrogen atoms or (meth)acryloyl groups, and one or more of the terminal groups are active hydrogen atoms;
• and
• the linking group (Z) is a divalent group represented by general formula (2), and when the compound represented by the general formula (1A) contains a plurality of the linking groups (Z), the linking groups (Z) may be the same as or different from each other;
• wherein in the general formula (2), n2a, n2b, n2c and n2c represent unit numbers of respective repeating units, and are each 0 to 100, a sum of n2a, n2b, n2c and n2d is 1 to 100, a left end of the group is bonded to the core (X), and a right end of the group is bonded to the terminal group (Y1A);
• and
• wherein in the general formula (3), R3a represents a hydrogen atom or a methyl group, R3b represents a C2-6 linear alkylene group or a C2-6 linear oxyalkylene group, and the linear alkylene group or the linear oxyalkylene group is optionally substituted with a C1-6 alkyl group and/or a (meth)acryloyloxymethylene group in place of a hydrogen atom,
• under a condition of (total equivalents/moles of isocyanate groups present in the reaction derived from the compound represented by the general formula (3))/(total equivalents/moles of active hydrogen atoms of (Y1A) bonded to terminal oxygen atoms and nitrogen atoms of the core (X) present in the compound represented by general formula (1A))=1,
• wherein the compound (1A) is at least one selected from the group consisting of compounds represented by general formulas (6′a) to (6′k):
• wherein n6′i-a, n6′j-a and n6′k-a in the general formulas (6′i), (6′j) and (6′k) each represent a number of arms of a polyol bonded to the core X, and are each an integer of not less than 3;
• and
• n6′i-b and n6′j-b in the general formulas (6′i) and (6′j) represent numbers of oxyethylene units and oxypropylene units, respectively, and are each in the range of 1 to 100, the numbers of units for respective arms may be the same as or different from each other, n6′k-b and n6′k-c in the general formula (6′k) represent numbers of oxyethylene units and oxypropylene units, respectively, a sum thereof is in the range of 1 to 100, and the sums of the numbers of units for respective arms may be the same as or different from each other.