Infiltrant for dental application

Abstract

The invention provides an infiltrant for dental application that comprises crosslinking monomers. In accordance with the invention the infiltrant has a penetration coefficient PC>50 cm/s, and the crosslinking monomers, based on the total mass of monomers, comprise at least 5% by weight of crosslinking monomers having at least three polymerizable groups and not more than 95% by weight of crosslinking monomers having two polymerizable groups.

1 . An infiltrant for dental application, comprising crosslinking monomers, which has a penetration coefficient PC>50 cm/s, and the crosslinking monomers, based on the total mass of monomers, comprise at least 5% by weight of crosslinking monomers having at least three polymerizable groups and not more than 95% by weight of crosslinking monomers having two polymerizable groups. 
     
     
         2 . The infiltrant of  claim 1 , having a penetration coefficient PC>100 cm/s. 
     
     
         3 . The infiltrant of  claim 1 , wherein the fraction of crosslinking monomers having at least three polymerizable groups is 10% to 50% by weight, preferably 10% to 30% by weight. 
     
     
         4 . The infiltrant of  claim 1 , wherein the fraction of crosslinking monomers having two polymerizable groups is 90% to 50% by weight, preferably 90% to 70% by weight. 
     
     
         5 . The infiltrant of  claim 1 , wherein the crosslinking monomers having two polymerizable groups are esters of acrylic or methacrylic acid and are preferably selected from the group consisting of DDDMA, 1,10-decanediol dimethacrylate; PEG400DA, polyethylene glycol 400 diacrylate; PEG400DMA, polyethylene glycol 400 dimethacrylate; PEG300DA, polyethylene glycol 300 diacrylate; PEG300DMA, polyethylene glycol 300 dimethacrylate; BPA(EO)10DMA, ethoxylated (10) bisphenyl A dimethacrylate; BPA(EO)30DMA, ethoxylated (30) bisphenol A dimethacrylate; PEG200DA, polyethylene glycol 200 diacrylate; PEG600DA, polyethylene glycol 600 diacrylate; NPG(PO)2DA, propoxylated (2) neopentylglycol diacrylate; BPA(EO)2DA, ethoxylated (4) bisphenol A diacrylate; BPA(PO)2DMA, propoxylated (2) bisphenol A dimethacrylate, bis-GMA, 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl]propane; UDMA, 1,6-bis(methacryloyloxy-2-ethoxycarbonylamino)-2,4,4-trimethylhexane; EGDMA, ethylene glycol dimethacrylate; 3EGDMA, triethylene glycol dimethacrylate; 4EGDMA, tetraethylene glycol dimethacrylate; BDMA, 1,3-butylene glycol dimethacrylate; HDDMA, 1,6-hexanediol dimethacrylate; 1,4-butylenediol diacrylate; 4EDA, tetraethylene glycol diacrylate; NDDA, 1,9-nonanediol diacrylate; DEGDMA, diethylene glycol dimeth-acrylate; PDDMA, 1,5-pentanediol dimethacrylate; BDDMA, 1,4-butanediol dimethacrylate; PRDMA, 1,3-propanediol dimethacrylate; and DMTCDDA, dimethyloltricyclo[5.2.1.0]decane dimethacrylate. 
     
     
         6 . The infiltrant of  claim 1 , wherein the crosslinking monomers having at least three polymerizable groups have a distance between crosslinking points of at least 7 bond lengths, preferably not more than 50 bond lengths, more preferably 10 to 30 bond lengths, more preferably 11 to 21 bond lengths. 
     
     
         7 . The infiltrant of  claim 1 , wherein the fraction of crosslinking monomers having at least three polymerizable groups and a distance between crosslinking points of less than 10 bond lengths, based on the total mass of the monomers, is less than 20% by weight, preferably less than 10% by weight, more preferably less than 5% by weight. 
     
     
         8 . The infiltrant of  claim 1 , wherein the crosslinking monomers having at least three polymerizable groups have the formula below
   R 1 [X k R 2   1 Y m ] n      
       having the following definitions:
 R 1  is a linear or branched hydrocarbon having 3-24 C atoms, comprising alkyl, cycloalkyl or aryl; 
 optionally containing O, N, Si, S, P as hetero-atoms, examples being siloxane and/or cyclosiloxane and/or carbosilane and/or cyclocarbosilane and/or, in particular, ether groups or polyether groups, polyester groups, polysiloxane groups or polycarbosilane groups; 
 optionally substituted by hydroxyl and/or carbonyl and/or halogen (preferably fluorine) and/or ammonium-alkylene groups and/or siloxane and/or cyclosiloxane and/or carbosilane and/or cyclo-carbosilane; 
 R 2  is a linear or branched hydrocarbon having 1-16 C atoms, comprising alkyl, cycloalkyl or aryl; 
 optionally containing O, N, Si, S, P as hetero-atoms, examples being siloxane and/or cyclosiloxane and/or carbosilane and/or cyclocarbosilane and/or, in particular, ether groups or polyether groups, polyester groups, polysiloxane groups or polycarbosilane groups; 
 optionally substituted by hydroxyl and/or carbonyl and/or halogen (preferably fluorine) and/or ammonium-alkylene groups and/or siloxane and/or cyclosiloxane and/or carbosilane and/or cyclocarbosilane; 
 X is a linking group identically or differently selected from an ether group, carbonyl group, ester group, amide group, urethane group or urea group; 
 Y is a group identically or differently containing a polymerizable double bond and/or a ring-openingly polymerizable group and/or a thiol group; preferably vinyl, (meth)acrylate, (meth)acrylamide or epoxide groups; 
 k is 0 or 1; 
 l is 0 or 1; 
 m is at least 1; 
 n is at least 1; and 
 m×n is at least 3. 
 
     
     
         9 . The infiltrant of  claim 1 , wherein the crosslinking monomers having at least three polymerizable groups are selected from the group consisting of TMPTMA, trimethylolpropane trimethacrylate; TMPTA, trimethylolpropane triacrylate; DTMPTA, ditrimethylolpropane tetra(meth)acrylate; diPENTA, dipentaerythritol penta(meth)acrylate; GPTA, propoxylated glyceryl tri(meth)acrylate; DPEHA, dipentaerythritol hexa(meth)acrylate; and ethoxylated trimethylolpropane tri(meth)acrylate; preferably selected from the group consisting of propoxylated glyceryl tri(meth)acrylate; ethoxylated trimethylolpropane trimethacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane trimethacrylate, propoxylated trimethylolpropane triacrylate, ethoxylated pentaerythritol trimethacrylate, ethoxylated pentaerythritol triacrylate, ethoxylated pentaerythritol tetramethacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated dipentaerythritol trimethacrylate, ethoxylated dipentaerythritol tetramethacrylate, ethoxylated dipentaerythritol pentamethacrylate, ethoxylated dipentaerythritol hexamethacrylate, ethoxylated dipentaerythritol triacrylate, ethoxylated dipentaerythritol tetraacrylate, ethoxylated dipentaerythritol pentaacrylate, ethoxylated dipentaerythritol hexaacrylate, propoxylated pentaerythritol trimethacrylate, propoxylated pentaerythritol triacrylate, propoxylated pentaerythritol tetramethacrylate, propoxylated pentaerythritol tetraacrylate, propoxylated dipentaerythritol trimethacrylate, propoxylated dipentaerythritol tetramethacrylate, propoxylated dipentaerythritol pentamethacrylate, propoxylated dipentaerythritol hexamethacrylate, propoxylated dipentaerythritol triacrylate, propoxylated dipentaerythritol tetraacrylate, propoxylated dipentaerythritol pentaacrylate and propoxylated dipentaerythritol hexaacrylate. 
     
     
         10 . The infiltrant of  claim 1 , further comprising monomers having only one polymerizable group; the monomers having only one polymerizable group are preferably selected from the group consisting of MMA, methyl methacrylate; EMA, ethyl methacrylate; n-BMA, n-butyl methacrylate; IBMA, isobutyl methacrylate, t-BMA, tert-butyl methacrylate; EHMA, 2-ethylhexyl methacrylate, LMA, lauryl methacrylate; TDMA, tridecyl methacrylate; SMA, stearyl methacrylate; CHMA, cyclohexyl methacrylate; BZMA, benzyl methacrylate, IBXMA, isobornyl methacrylates; MAA, methacrylic acid; HEMA, 2-hydroxyethyl methacrylate; HPMA, 2-hydroxypropyl methacrylate; DMMA, dimethylaminoethyl methacrylate; DEMA, diethylaminoethyl methacrylate; GMA, glycidyl methacrylate; THFMA, tetrahydrofurfuryl methacrylate; AMA, allyl methacrylate; ETMA, ethoxyethyl methacrylate; 3FM, trifluoroethyl methacrylate; 8FM, octafluoropentyl methacrylate; AIB, isobutyl acrylate; TBA, tert-butyl acrylate; LA, lauryl acryate; CEA, cetyl acrylate; STA, stearyl acrylate; CHA, cyclohexyl acrylate; BZA, benzyl acrylate; IBXA, isobornyl acrylate; 2-MTA, 2-methoxyethyl acrylate; ETA, 2-ethoxyethyl acrylate; EETA, ethoxyethoxyethyl acrylate; PEA, 2-phenoxyethyl acrylate; THFA, tetrahydrofurfuryl acrylate; HEA, 2-hydroxyethyl acrylate; HPA, 2-hydroxypropyl acrylate; 4HBA, 4-hydroxybutyl acrylate; DMA, dimethylaminoethyl acrylate; 3F, trifluoroethyl acrylate; 17F, heptadecafluorodecyl acrylate, 2-PEA, 2-phenoxyethyl acrylate; TBCH, 4-tert-butylcyclohexyl acrylate; DCPA, dihydrodicyclopentadienyl acrylate; EHA, 2-ethylhexyl acrylate; and 3EGMA, triethylene glycol monomethacrylate. 
     
     
         11 . The infiltrant of  claim 1 , having a dynamic viscosity of 50 mPas or less, preferably 30 mPas or less, more preferably 15 mPas or less. 
     
     
         12 . The infiltrant of  claim 1 , containing 20% by weight or less, preferably 10% by weight or less of solvent. 
     
     
         13 . A kit for preparing an infiltrant of  claim 1 , wherein the kit comprises a first component with monomers and chemically activable initiators and a second component with activators. 
     
     
         14 . A kit for preparing an infiltrant of  claim 1 , wherein the kit further comprises etching agents and/or drying agents. 
     
     
         15 . Use of the infiltrant of  claim 1  to treat and/or prevent carious enamel lesions.