+

US20030105184A1 - Polyaminoester and their application in dental compositions - Google Patents

Polyaminoester and their application in dental compositions Download PDF

Info

Publication number
US20030105184A1
US20030105184A1 US10/308,520 US30852002A US2003105184A1 US 20030105184 A1 US20030105184 A1 US 20030105184A1 US 30852002 A US30852002 A US 30852002A US 2003105184 A1 US2003105184 A1 US 2003105184A1
Authority
US
United States
Prior art keywords
unsubstituted
substituted
difunctional substituted
difunctional
arylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/308,520
Inventor
Uwe Walz
Joachim Klee
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dentsply Detrey GmbH
Original Assignee
Dentsply Detrey GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dentsply Detrey GmbH filed Critical Dentsply Detrey GmbH
Priority to US10/308,520 priority Critical patent/US20030105184A1/en
Publication of US20030105184A1 publication Critical patent/US20030105184A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/50—Preparations specially adapted for dental root treatment
    • A61K6/54—Filling; Sealing
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • oligoamido amines and oligoester amines based on antibiotics containing .beta.-lactam rings were investigated (Panayotov, Eur. Polym. J. 32 (1996) 957-962). They were prepared by interaction between ampicillin and amoxicillin and methylenebisacrylamide, 1,4-diacryloylpiperazine and 1,3-propanediol diacrylate.
  • Dental compositions comprising at least a polymerizable monomer and/or at least a polyaminoester of formulas 1 to 6, pigments, organic and/or inorganic fillers, initiators and stabilizers.
  • R 1 denotes is a difunctional substituted or unsubstituted C 1 to C 18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C 5 to C 18 arylene or heteroarylene, difunctional substituted or unsubstituted C 5 to C 18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C 7 to C 30 alkylene arylene,
  • R 2 denotes is a difunctional substituted or unsubstituted C 1 to C 18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C 5 to C 18 arylene or heteroarylene, difunctional substituted or unsubstituted C 5 to C 18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C 7 to C 30 alkylene arylene,
  • R 3 denotes H or a substituted or unsubstituted C 1 to C 18 alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted C 5 to C 18 arylene or heteroarylene, substituted or unsubstituted C 5 to C 18 alkylarylene or alkylheteroarylene, substituted or unsubstituted C 7 to C 30 alkylene arylene,
  • n is an integer.
  • the invented dental composition contains a polyaminoester that are characterized by the following formulas
  • R 1 denotes is a difunctional substituted or unsubstituted C 1 to C 18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C 5 to C 18 arylene or heteroarylene, difunctional substituted or unsubstituted C 5 to C 18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C 7 to C 30 alkylene arylene,
  • R 2 denotes is a difunctional substituted or unsubstituted C 1 to C 18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C 5 to C 18 arylene or heteroarylene, difunctional substituted or unsubstituted C 5 to C 18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C 7 to C 30 alkylene arylene, and
  • n is an integer.
  • polyaminoesters are applied characterized by the following formulas
  • n is an integer.
  • Said polymerizable monomer preferably are hydroxyethyl methacrylate, hydroxyethylacrylate, hydroxypropyl methacrylate, ethyleneglykol dimethacrylate, diethyleneglykol dimethacrylate, triethyleneglykol dimethacrylate, 3,(4),8,(9)-Dimethacryloyl-(oxymethyl)-tricyclo-5.2.1.0 2.6 decane, trimethylolpropane triacrylate or trimethylolpropane trimethacrylate, N,N′-dimethylaminoethyl methacrylate.
  • fillers are applied inorganic or organic, reactive or nonreactive, surface modified or nonmodified glasses such as polymer granulate or a combination of organic and/or inorganic fillers, strontium alumo silicate glass, La 2 O 3 , BiPO 4 , ZrO 2 , BaWO 4 , CaWO 4 , SrF 2 , Bi 2 O 3 .
  • the invented dental composition preferably is applicable as root canal sealing material or as temporary crown & bridge material.
  • ⁇ Pa*s (dynamic viscosity measured using Bohlin CS50 rheometer)
  • ⁇ Pa*s (dynamic viscosity measured using Bohlin CS50 rheometer)
  • Paste A Immediately before use 0.214 g of Paste A and 0.200 g of Paste B were mixed homogeneously.
  • the setting time of the root canal sealing material is 30 minutes.
  • the radiopacity 12.8 mm/mm Al.
  • Paste A 0.173 g of Paste A and 0.200 g of Paste B were mixed homogeneously.
  • the setting time of the root canal sealing material is 30 minutes.

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Dental Preparations (AREA)

Abstract

Dental compositions comprising at least a polymerizable monomer and/or at least a polyaminoester that are prepared by reaction of bis- or polyacrylic esters and amines, pigments, organic and/or inorganic fillers, initiators and stabilizers.

Description

    TECHNICAL BACKGROUND
  • Since some years, the addition polymerization of bisacrylamides and amines is well-known (P. Ferrutti et al., Polymer 26 (1985) 1336). Bisacrylamides are much more stable against hydrolysis compared to acrylic esters. The reaction of amines and esters lead to an transamidation reaction (H. -G. Elias, Makromoleküle, Hüttig&Wepf, Basel, 1990, p.555). Consequently, the assumption was that a reaction of acrylic esters and amines should lead to an cleavage of ester bonds. Therefore, the formation of addition polymers, prepolymers and macromonomers of amines and acrylic esters should be impossible. [0001]
  • Recently, oligoamido amines and oligoester amines based on antibiotics containing .beta.-lactam rings were investigated (Panayotov, Eur. Polym. J. 32 (1996) 957-962). They were prepared by interaction between ampicillin and amoxicillin and methylenebisacrylamide, 1,4-diacryloylpiperazine and 1,3-propanediol diacrylate. [0002]
    • DESCRIPTION OF THE INVENTION
  • Dental compositions comprising at least a polymerizable monomer and/or at least a polyaminoester of formulas 1 to 6, pigments, organic and/or inorganic fillers, initiators and stabilizers. [0003]
    Figure US20030105184A1-20030605-C00001
  • wherein [0004]
  • R[0005] 1 denotes is a difunctional substituted or unsubstituted C1 to C18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C5 to C18 arylene or heteroarylene, difunctional substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C7 to C30 alkylene arylene,
  • R[0006] 2 denotes is a difunctional substituted or unsubstituted C1 to C18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C5 to C18 arylene or heteroarylene, difunctional substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C7 to C30 alkylene arylene,
  • R[0007] 3 denotes H or a substituted or unsubstituted C1 to C18 alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted C5 to C18 arylene or heteroarylene, substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, substituted or unsubstituted C7 to C30 alkylene arylene,
  • n is an integer. [0008]
  • Preferably the invented dental composition contains a polyaminoester that are characterized by the following formulas [0009]
    Figure US20030105184A1-20030605-C00002
  • wherein [0010]
  • R[0011] 1 denotes is a difunctional substituted or unsubstituted C1 to C18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C5 to C18 arylene or heteroarylene, difunctional substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C7 to C30 alkylene arylene,
  • R[0012] 2 denotes is a difunctional substituted or unsubstituted C1 to C18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C5 to C18 arylene or heteroarylene, difunctional substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C7 to C30 alkylene arylene, and
  • n is an integer. [0013]
  • Most preferably polyaminoesters are applied characterized by the following formulas [0014]
    Figure US20030105184A1-20030605-C00003
  • wherein n is an integer. [0015]
  • Said polymerizable monomer preferably are hydroxyethyl methacrylate, hydroxyethylacrylate, hydroxypropyl methacrylate, ethyleneglykol dimethacrylate, diethyleneglykol dimethacrylate, triethyleneglykol dimethacrylate, 3,(4),8,(9)-Dimethacryloyl-(oxymethyl)-tricyclo-5.2.1.0 [0016] 2.6 decane, trimethylolpropane triacrylate or trimethylolpropane trimethacrylate, N,N′-dimethylaminoethyl methacrylate.
  • As fillers are applied inorganic or organic, reactive or nonreactive, surface modified or nonmodified glasses such as polymer granulate or a combination of organic and/or inorganic fillers, strontium alumo silicate glass, La[0017] 2O3, BiPO4, ZrO2, BaWO4, CaWO4, SrF2, Bi2O3.
  • Instead of primary monoamine and disecondary diamines the usage of polyamines is possible, too, leading to crosslinked polyaminoesters. [0018]
  • The invented dental composition preferably is applicable as root canal sealing material or as temporary crown & bridge material.[0019]
    • EXAMPLE 1
  • 5.000 g (22.097 mmol) Hexamethylendiacrylate (Servo Delden) and 7.525 g (22.097 mmol) N,N′-Dibenzyl-5-nonandiamin-1,9 were mixed homogeneously and stirred at 60° C. for 4 days. After that time a complete conversion was found indicated by disappearance of the double bonds at 1635/1619 cm[0020] −1.
  • Yield: 12.525 g (100% of th.) [0021]
  • (C[0022] 34H50N2O5)n, (566.8)n
  • [η]=8.57 ml/g (Viscosity in THF solution) [0023]
  • IR: 2920/2865 (CH[0024] 2), 1735 (CO)
  • M[0025] n (GPC)=2225 (4661) g/mol
  • M[0026] w (GPC)=9398 (10200) g/mol
    • EXAMPLE 2
  • 20.000 g (88.39 mmol) Hexamethylendiacrylate (Servo Delden) and 15.719 g (106.07 mmol) 3,6-Dioxaoctan-diamin-1,8 (Fluka) were mixed homogeneously and stirred at room temperature for 1.5 hours. After that time a complete conversion was found indicated by disappearance of the double bonds at 1635/1619 cm[0027] −1.
  • Yield: 35.719 g (100% of th.) [0028]
  • (C[0029] 18H34N2O6)n, (347.5)n
  • η=4.73±0.05 Pa*s (dynamic viscosity measured using Bohlin CS50 rheometer) [0030]
  • IR: 3325 (NH), 2920/2865 (CH[0031] 2), 1735 (CO)
  • [0032] 13C-NMR (CDCl3): 172.6/172.4 (6), 73.4 (2); 70.5/70.2 (3); 64.2 (7), 49.8 (1), 45.0 (4), 41.7 (4), 34.8 (5), 28.4 (8), 25.5 (9)
  • IR: 3325 (NH), 2920/2865 (CH[0033] 2),1735 (CO)
    • EXAMPLE 3
  • 10.000 g (58.77 mmol) Ethylene glycol diacrylate and 14.125 g (58.77 mmol) N,N′-Dibenzylethylenediamine were mixed homogeneously and stirred at room temperature for 40 hours at 60° C. After that time a complete conversion was found indicated by disappearance of the double bonds at 1635/1619 cm[0034] −1.
  • Yield: 24.125 g (100% of th.) [0035]
  • η=1557±17 Pa*s (dynamic viscosity measured using Bohlin CS50 rheometer) [0036]
  • [η]=9.176 ml/g (viscosity in THF solution) [0037]
  • M[0038] n (GPC)=1575 g/mol
  • M[0039] w (GPC)=10060 g/mol
  • (C[0040] 24H32N2O4)n, (410.5)n
  • IR: 3060/3028; 2953/2816 (CH[0041] 2), 1743 (CO)
  • [0042] 13C NMR (CDCl3): 49.7 (1), 32.4 (2), 172.6 (3), 621.0 (4), 51.5 (5), 58.6 (6), 139.2 (7), 128.6 (8), 128.0 (9),126.8 (10)
    Figure US20030105184A1-20030605-C00004
    • EXAMPLE 4
  • 10.000 g (58.77 mmol) Ethylene glykol diacrylate and 20.012 g (58.77 mmol) N,N′-Dibenzyl-5-oxanonane diamine-1.9 were mixed homogeneously and stirred at room temperature for 40 hours at 60° C. After that time a complete conversion was found indicated by disappearance of the double bonds at 1635/1619 cm[0043] −1.
  • Yield: 30.012 g (100% of th.) [0044]
  • η=188.8±1.3 Pa*s (dynamic viscosity measured using Bohlin CS50 rheometer) [0045]
  • [η]=10.051 ml/g (viscosity in THF solution) [0046]
  • M[0047] n (GPC)=4281 g/mol
  • M[0048] w (GPC)=12110 g/mol
  • (C[0049] 30H42N2O5)n, (510.7)n
  • IR: 3060/3026/2943/2860/2802 (CH[0050] 2), 1740/1731 (CO)
  • [0051] 13C NMR (CDCl3): 49.1 (1), 32.4 (2), 172.3 (3), 62.1 (4), 53.2 (5), 58.2 (6), 139.5 (7), 128.0 (8), 127.9 (9), 126.7 (10), 27.5 (11), 23.5 (12)
    Figure US20030105184A1-20030605-C00005
    • EXAMPLE 5
  • 10.000 g (58.77 mmol) Ethylene glykol diacrylate and 11.420 g (58.77 mmol) N,N′-Dibenzyl-4,4′-dicyclohexylmethane were mixed homogeneously and stirred at room temperature for 40 hours at 60° C. After that time a complete conversion was found indicated by disappearance of the double bonds at 1635/1619 cm[0052] −1.
  • Yield: 21.420 g (100% of th.) [0053]
  • IR: 3060/3026/2943/2860/2802 (CH[0054] 2), 1740/1731 (CO)
    • EXAMPLE 6
  • 10.000 g (58.77 mmol) Ethylene glykol diacrylate and 5.710 g (29.384 mmol) 3,(4),8,(9)-Bis(aminomethyl)-tricyclo-5.2.1.0 [0055] 2.6 decane were mixed homogeneously and stirred at room temperature for 2 hours at room temperature. After that time a complete conversion was found indicated by disappearance of the double bonds at 1635/1619 cm−1.
  • Yield: 15.710 g (100% of th.) [0056]
  • η=Pa*s (dynamic viscosity measured using Bohlin CS50 rheometer) [0057]
  • (C[0058] 28H42N2O8)n, (534.7)n
  • IR: 3445/3332 (NH), 2947/2875/2821 (CH[0059] 2), 1729 (CO); 1637/1619 (C═C)
    • EXAMPLE 7
  • 10.000 g (58.77 mmol) Ethylene glykol diacrylate and 22.840 5.710 g (117.54 mmol) 3,(4),8,(9)-Bis(aminomethyl)-tricyclo-5.2.1.0 [0060] 2,6 decane were mixed homogeneously and stirred at room temperature for 2 hours at room temperature. After that time a complete conversion was found indicated by disappearance of the double bonds at 1635/1619 cm−1.
  • Yield: 32.840 g (100% of th.) [0061]
  • η=218800±1990 Pa*s (dynamic viscosity measured using Bohlin CS50 rheometer) [0062]
  • (C[0063] 32H54N4O4)n, (558.8)n
  • IR: 3373/3286 (NH), 2960/2888 (CH[0064] 2), 1743/1731 (CO)
  • [0065] 13C NMR (CDCl3): 47.5 (1), 34.3/34.7 (2), 172.9 (3), 66.0 (4), 55.3 (5), signals of (6) to (15) between 24.5 and 63.5 ppm
    Figure US20030105184A1-20030605-C00006
    • EXAMPLE 8
  • To 10.000 g (58.77 mmol) Ethylene glykol diacrylate dissolved in 50 ml THF were slowly added at 0 to 5° C. under stirring a solution of 8.709 g (58.77 mmol) 3,6-Dioxaoctane diamine-1,8 in 50 ml THF. After adding the amine the solution was stirred at room temperature for 1.5 hours. After that time a complete conversion was found due to the disappearance of the double bonds at 1635/1619 cm[0066] −1. Then the solvent was removed and the addition polymer was dried in vacuum.
  • Yield: 18.709 g (100% of th.) [0067]
  • η=Pa*s (dynamic viscosity measured using Bohlin CS50 rheometer) [0068]
  • (C[0069] 14H26N2O6)n, (318.4)n
  • IR: 3373/3286 (NH), 2960/2888 (CH[0070] 2), 1743/1731 (CO)
    • Application Example 1 (Dental Root Canal Sealer)
  • Paste A [0071]
  • 8.404 g (37.14 mmol) Hexamethylendiacrylate (Servo Delden), 25.968 g CaWO[0072] 4, 6.492 g ZrO2 and 0.325 g aerosil were mixed homogeneously.
  • Paste B [0073]
  • 7.217 g (37.14 mmol) 3,(4),8,(9)-Bis(aminomethyl)-tricyclo-5.2.1.0 [0074] 2,6 decane, 28.867 g CaWO4, 7.217 g ZrO2 and 0.722 g aerosil were mixed homogeneously.
  • Dental Root Canal Sealer [0075]
  • Immediately before use 0.214 g of Paste A and 0.200 g of Paste B were mixed homogeneously. The setting time of the root canal sealing material is 30 minutes. The radiopacity of 12.8 mm/mm Al. [0076]
    • Application Example 2 (Dental Root Canal Sealer)
  • Paste A [0077]
  • 2.5213 g (11.14 mmol) Hexamethylendiacrylate (Servo Delden), 12.9298 g CaWO[0078] 4, 3.2325 g ZrO2 and 0.0385 g aerosil were mixed homogeneously.
  • Paste B [0079]
  • 0.801 g (5.29 mmol) 1-Aminoadamantane, 1.802 g (5.29 mmol) N,N′-Dibenzyl-5-oxanonandiamin-1,9, 0.103 g (0.53 mmol) 3,(4),8,(9)-Bis(aminomethyl)-tricyclo-5.2.1.0 [0080] 2,6 decane, 10.411 g CaWO4, 2.603 g ZrO2 and 0.315 g aerosil were mixed homogeneously.
  • Dental Root Canal Sealer [0081]
  • Immediately before use 0.173 g of Paste A and 0.200 g of Paste B were mixed homogeneously. The setting time of the root canal sealing material is 30 minutes. The radiopacity of 13.8 mm/mm Al. [0082]

Claims (10)

We claim
1. Dental compositions comprising at least a polymerizable monomer and/or at least a polyaminoester of formulas 1 to 6, pigments, organic and/or inorganic fillers, initiators and stabilizers.
Figure US20030105184A1-20030605-C00007
wherein
R1 denotes is a difunctional substituted or unsubstituted C1 to C18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C5 to C18 arylene or heteroarylene, difunctional substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C7 to C30 alkylene arylene,
R2 denotes is a difunctional substituted or unsubstituted C1 to C18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C5 to C18 arylene or heteroarylene, difunctional substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C7 to C30 alkylene arylene,
R3 denotes H or a substituted or unsubstituted C1 to C18 alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted C5 to C18 arylene or heteroarylene, substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, substituted or unsubstituted C7 to C30 alkylene arylene,
n is an integer.
2. Dental composition of claim 1, wherein said polyaminoester is characterized by the following formulas
Figure US20030105184A1-20030605-C00008
wherein
R1 denotes is a difunctional substituted or unsubstituted C1 to C18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C5 to C18 arylene or heteroarylene, difunctional substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C7 to C30 alkylene arylene,
R2 denotes is a difunctional substituted or unsubstituted C1 to C18 alkylene, difunctional substituted or unsubstituted cycloalkylene, difunctional substituted or unsubstituted C5 to C18 arylene or heteroarylene, difunctional substituted or unsubstituted C5 to C18 alkylarylene or alkylheteroarylene, difunctional substituted or unsubstituted C7 to C30 alkylene arylene, and
n is an integer.
3. Dental composition of claim 1, wherein said polyaminoesters preferably is characterized by the following formula
Figure US20030105184A1-20030605-C00009
wherein n is an integer.
4. Dental composition of claim 1, wherein said polyaminoesters preferably is characterized by the following formula
Figure US20030105184A1-20030605-C00010
wherein n is an integer.
5. Dental composition of claim 1, wherein said polyaminoesters are composed of polyamines and bis- or polyacrylates.
6. Dental composition of claim 1, wherein said polyaminoesters are copolymerized with monomers that are usable for step-growth polymerization, preferably with di- or polyepoxides or di- or polyisocyanates.
7. Dental composition of claim 1, wherein said polymerizable monomer preferably is hydroxyethyl methacrylate, hydroxyethylacrylate, hydroxypropyl methacrylate, ethyleneglykol dimethacrylate, diethyleneglykol dimethacrylate, triethyleneglykol dimethacrylate, 3,(4),8,(9)-Dimethacryloyl-(oxymethyl)-tricyclo-5.2.1.0 2,6 decane, trimethylolpropane triacrylate or trimethylolpropane trimethacrylate, N,N′-dimethylaminoethyl methacrylate.
8. Dental composition of claim 1, wherein said fillers are functionalized or non-functionalized organic polymers or wherein said fillers are inorganic or organic, reactive or non-reactive, surface modified or non-modified glasses such as polymer granulate or a combination of organic and/or inorganic fillers, strontium alumo silicate glass, La2O3, BiPO4, ZrO2, BaWO4, CaWO4, SrF2, Bi2O3.
9. Dental composition of claim 1, applicable as root canal sealing material.
10. Dental composition of claim 1, applicable as temporary crown & bridge material.
US10/308,520 2000-08-11 2002-12-03 Polyaminoester and their application in dental compositions Abandoned US20030105184A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US10/308,520 US20030105184A1 (en) 2000-08-11 2002-12-03 Polyaminoester and their application in dental compositions

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US22466900P 2000-08-11 2000-08-11
US09/925,174 US6734223B2 (en) 2000-08-11 2001-08-09 Polyaminoester and their application in dental compositions
US10/308,520 US20030105184A1 (en) 2000-08-11 2002-12-03 Polyaminoester and their application in dental compositions

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US09/925,174 Division US6734223B2 (en) 2000-08-11 2001-08-09 Polyaminoester and their application in dental compositions

Publications (1)

Publication Number Publication Date
US20030105184A1 true US20030105184A1 (en) 2003-06-05

Family

ID=22841652

Family Applications (3)

Application Number Title Priority Date Filing Date
US09/925,174 Expired - Lifetime US6734223B2 (en) 2000-08-11 2001-08-09 Polyaminoester and their application in dental compositions
US10/308,520 Abandoned US20030105184A1 (en) 2000-08-11 2002-12-03 Polyaminoester and their application in dental compositions
US10/793,356 Abandoned US20040220291A1 (en) 2000-08-11 2004-03-04 Polyaminoester and their application in dental compositions

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US09/925,174 Expired - Lifetime US6734223B2 (en) 2000-08-11 2001-08-09 Polyaminoester and their application in dental compositions

Family Applications After (1)

Application Number Title Priority Date Filing Date
US10/793,356 Abandoned US20040220291A1 (en) 2000-08-11 2004-03-04 Polyaminoester and their application in dental compositions

Country Status (6)

Country Link
US (3) US6734223B2 (en)
EP (1) EP1307172B1 (en)
JP (1) JP4989011B2 (en)
CA (1) CA2418278A1 (en)
DE (1) DE60120416T2 (en)
WO (1) WO2002013767A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040220291A1 (en) * 2000-08-11 2004-11-04 Uwe Walz Polyaminoester and their application in dental compositions

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE43612E1 (en) 2000-10-10 2012-08-28 Massachusetts Institute Of Technology Biodegradable poly(β-amino esters) and uses thereof
US6998115B2 (en) * 2000-10-10 2006-02-14 Massachusetts Institute Of Technology Biodegradable poly(β-amino esters) and uses thereof
JP4827735B2 (en) * 2003-07-31 2011-11-30 デンツプライ デトレイ ゲー．エム．ベー．ハー． Dental root canal sealing composition
WO2005013921A1 (en) * 2003-07-31 2005-02-17 Dentsply Detrey Gmbh Dental root canal sealing composition
JP4785742B2 (en) * 2003-07-31 2011-10-05 デンツプライ デトレイ ゲー．エム．ベー．ハー． Dental root canal sealing composition
DE602004021391D1 (en) * 2003-07-31 2009-07-16 Dentsply Detrey Gmbh DENTAL ROOT CANAL LOCK COMPOSITION
US7943179B2 (en) 2003-09-23 2011-05-17 Massachusetts Institute Of Technology pH triggerable polymeric particles
DE60322404D1 (en) 2003-12-23 2008-09-04 Dentsply Detrey Gmbh Filling material for tooth root canal
DE602006018023D1 (en) 2005-08-08 2010-12-16 Angstrom Medica Inc CEMENT PRODUCTS AND METHOD FOR THE PRODUCTION AND USE THEREOF
US8808681B2 (en) 2006-06-05 2014-08-19 Massachusetts Institute Of Technology Crosslinked, degradable polymers and uses thereof
CA2658768C (en) 2006-07-21 2016-05-17 Massachusetts Institute Of Technology End-modified poly(beta-amino esters) and uses thereof
DE102007029640A1 (en) 2007-06-26 2009-01-02 S&C Polymer Silicon- und Composite-Spezialitäten GmbH Root canal filling material
EP2192886B1 (en) 2007-08-28 2017-12-20 Pioneer Surgical Technology, Inc. Cement products and methods of making and using the same
EP2609135A4 (en) 2010-08-26 2015-05-20 Massachusetts Inst Technology POLY (BETA-AMINO ALCOHOLS), THEIR PREPARATION AND USES THEREOF
US8915736B2 (en) 2010-09-30 2014-12-23 Voco Gmbh Composition comprising a monomer with a polyalicyclic structure element for filling and/or sealing a root canal
EP2638892A1 (en) 2012-03-13 2013-09-18 S & C Polymer Silicon- und Composite-Spezialitäten GmbH Bioactive hydraulic organic matrix materials
EP3700965A1 (en) 2017-10-27 2020-09-02 Massachusetts Institute of Technology Poly (beta-amino esters) and uses thereof
WO2020086965A1 (en) 2018-10-26 2020-04-30 Massachusetts Institute Of Technology Polymer-lipids and compositions

Citations (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4089763A (en) * 1973-04-24 1978-05-16 Imperial Chemical Industries Limited Method of repairing teeth using a composition which is curable by irradiation with visible light
US4297266A (en) * 1980-02-08 1981-10-27 Den-Mat, Inc. Microfilled dental composite and method using the same
US4323348A (en) * 1979-08-07 1982-04-06 Bayer Aktiengesellschaft Dental compositions
US4386912A (en) * 1980-04-29 1983-06-07 Kuraray Company Limited Method for filling tooth cavities employing a polymerizable urethane cement composition
US4457818A (en) * 1978-12-18 1984-07-03 Imperial Chemical Industries Plc Dental compositions from urethane acrylate, diacrylate monomer, camphorquinone and dimethylaminoethyl methacrylate
US4525256A (en) * 1983-07-01 1985-06-25 Johnson & Johnson Dental Products Company Photopolymerizable composition including catalyst comprising diketone plus 4-(N,N-dimethylamino)benzoic acid or ester thereof
US4558120A (en) * 1983-01-07 1985-12-10 The Dow Chemical Company Dense star polymer
US4587329A (en) * 1984-08-17 1986-05-06 The Dow Chemical Company Dense star polymers having two dimensional molecular diameter
US4674980A (en) * 1982-05-03 1987-06-23 Den-Mat, Inc. Dental composite and porcelain repair
US4746686A (en) * 1987-04-17 1988-05-24 Kerr Manufacturing Company Visible light activated cavity liner
US4857599A (en) * 1988-02-08 1989-08-15 The Dow Chemical Company Modified dense star polymers
US4952241A (en) * 1986-07-25 1990-08-28 Bayer Aktiengesellschaft (Meth)acylic acid derivatives containing urethane groups
US5274064A (en) * 1990-03-23 1993-12-28 Imperial Chemical Industries Plc Star polymers containing hydrolysable group-bearing silicon atoms
US5308886A (en) * 1990-04-20 1994-05-03 Japan Institute Of Advanced Dentistry Photosetting resin for making strong, tough resin articles
US5395883A (en) * 1990-09-28 1995-03-07 General Electric Company Thermoplastic resin compositions containing polyphenylene ethers and polyesters
US5418301A (en) * 1992-02-26 1995-05-23 Perstorp Ab Dendritic macromolecule and process for preparation thereof
US5456602A (en) * 1993-01-29 1995-10-10 Gc Corporation Dental bonding
US5468789A (en) * 1994-09-12 1995-11-21 General Electric Company Method for making radiation curable silicon containing polyacrylate hardcoat compositions and compositions made thereby
US5486548A (en) * 1993-07-21 1996-01-23 Bayer Aktiengesellschaft Acrylates and methacrylates based on cyclohexyldiphenols
US5530092A (en) * 1992-01-13 1996-06-25 Dsm N.V. Dendritic macromolecule and the preparation thereof
US5545676A (en) * 1987-04-02 1996-08-13 Minnesota Mining And Manufacturing Company Ternary photoinitiator system for addition polymerization
US5624976A (en) * 1994-03-25 1997-04-29 Dentsply Gmbh Dental filling composition and method
US5679794A (en) * 1989-11-07 1997-10-21 Ciba-Geigy Corporation Polymer stabilizers containing both hindered amine and hydroxylamine moieties
US5709548A (en) * 1990-02-23 1998-01-20 Minnesota Mining And Manufacturing Company Dental crown liner composition and methods of preparing provisional applications
US5767170A (en) * 1995-07-05 1998-06-16 Den-Mat Corporation Dental adhesive comprising an unsaturated monomer, a coupling agent, a crosslinker, leachable fluoride and a photoinitiator
US5814681A (en) * 1994-10-13 1998-09-29 Kuraray Co., Ltd. Restorative composition for hard tissue and dispensing apparatus therefor
US5834118A (en) * 1994-09-08 1998-11-10 Neste Oy Of Keilaniemi Radiation curable resins comprising hyperbranched polyesters
US5847025A (en) * 1996-01-12 1998-12-08 Ivoclar Ag Light-curing composite material
US5847020A (en) * 1995-07-05 1998-12-08 Den-Mat Corporation Dental adhesive comprising a homogeneous mixture of an unsaturated monomer a coupling agent a crosslinking agent and a photoinitiator
US5886064A (en) * 1994-12-08 1999-03-23 Ivoclar Ag Fine-grained polymerizable compositions flowable under pressure or shear stress
US5914379A (en) * 1996-06-05 1999-06-22 Basf Aktiengesellschaft Compression of ethylenically unsaturated monomers
US5955514A (en) * 1993-04-19 1999-09-21 Dentsply Research & Development Corp. Dental composition and method
US5969000A (en) * 1997-01-17 1999-10-19 Jeneric Pentron Incorporated Dental resin materials
US6025114A (en) * 1995-03-11 2000-02-15 Zeneca Limited Liquid photocurable compositions
US6030606A (en) * 1998-06-22 2000-02-29 3M Innovative Properties Company Dental restoratives comprising Bis-EMA6
US6121344A (en) * 1998-06-19 2000-09-19 Kerr Corporation Optimum particle sized hybrid composite
US6136885A (en) * 1996-06-14 2000-10-24 3M Innovative Proprerties Company Glass ionomer cement
US6184339B1 (en) * 1996-11-14 2001-02-06 The United States Of America As Represented By The Secretary Of The Commerce High strength polymeric networks derived from (meth) acrylate resins with organofluorine content and process for preparing same

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE295645C (en)
SU334845A1 (en) 1970-07-22 1984-01-30 Филиал Института Химической Физики Ан Ссср Process for inhibiting radical polymerization of oligoester acrylates
DE2211128A1 (en) 1972-03-08 1973-09-13 Erich Kopp Dental prostheses - cast from compsn contg acrylamide and methylene-bisacrylamide, initiator activator and opt fillers
DE2931925A1 (en) 1979-08-07 1981-02-26 Bayer Ag (METH) ACRYLIC ACID ESTERS OF TRICYCLIC DECANDIOLES CONTAINING ETHER GROUPS
EP0049599A1 (en) 1980-10-02 1982-04-14 George Herrick Method and apparatus for forming an elevated concrete slab section of a building
IL65159A0 (en) 1981-03-04 1982-05-31 Ici Plc Polymerisable dental compositions
NZ204975A (en) 1982-08-02 1985-10-11 Johnson & Johnson Dental Prod Polymerisable dental restorative compositions having improved mechanical properties and hydrolytic stability
DE3703080A1 (en) 1986-07-25 1988-01-28 Bayer Ag (METH) ACRYLIC ACID ESTER
DE3703120A1 (en) 1986-07-25 1988-01-28 Bayer Ag URETHANE GROUPS CONTAINING (METH) ACRYLIC ACID DERIVATIVES FROM TRICYCLO (5.2.1.0 (UP ARROW) 2 (UP ARROW) (UP ARROW). (UP ARROW) (UP ARROW) 6 (UP ARROW)) DECANES
US5154762A (en) 1991-05-31 1992-10-13 Minnesota Mining And Manufacturing Company Universal water-based medical and dental cement
DE4133494C2 (en) * 1991-10-09 1996-03-28 Fraunhofer Ges Forschung Dental resin composition, process for their preparation and their use
BR9207009A (en) 1991-12-31 1995-12-05 Minnesota Mining & Mfg Composition of ethylenically unsaturated dental adhesive and process and kit for adhering a metal or metal-containing restorative to a hard tissue and hard surface
CA2124426C (en) 1993-06-23 2003-04-08 Louis H. Tateosian Dental composition, prostheses, and method for making dental prostheses
US5502087A (en) * 1993-06-23 1996-03-26 Dentsply Research & Development Corp. Dental composition, prosthesis, and method for making dental prosthesis
US5728872A (en) 1994-06-27 1998-03-17 Lutz Riemenschneider Stabilized acrylic acid compositions
US5973022A (en) * 1996-11-01 1999-10-26 Dentsply Research & Development Corp. Dental composition system and method
US6063830A (en) * 1996-12-06 2000-05-16 Kabushiki Kaisha Shofu Dental curable composition and artificial tooth
DE19848886C2 (en) 1998-10-23 2000-11-16 Heraeus Kulzer Gmbh & Co Kg Light-polymerizable one-component dental material
JP2002194320A (en) * 1999-12-27 2002-07-10 Mitsubishi Pencil Co Ltd Solid adhesive composition
JP4989011B2 (en) * 2000-08-11 2012-08-01 デンツプライ インターナショナル インコーポレーテッド Polyaminoesters and their application in dental treatment compositions

Patent Citations (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4089763A (en) * 1973-04-24 1978-05-16 Imperial Chemical Industries Limited Method of repairing teeth using a composition which is curable by irradiation with visible light
US4457818A (en) * 1978-12-18 1984-07-03 Imperial Chemical Industries Plc Dental compositions from urethane acrylate, diacrylate monomer, camphorquinone and dimethylaminoethyl methacrylate
US4323348A (en) * 1979-08-07 1982-04-06 Bayer Aktiengesellschaft Dental compositions
US4297266A (en) * 1980-02-08 1981-10-27 Den-Mat, Inc. Microfilled dental composite and method using the same
US4386912A (en) * 1980-04-29 1983-06-07 Kuraray Company Limited Method for filling tooth cavities employing a polymerizable urethane cement composition
US4674980A (en) * 1982-05-03 1987-06-23 Den-Mat, Inc. Dental composite and porcelain repair
US4558120A (en) * 1983-01-07 1985-12-10 The Dow Chemical Company Dense star polymer
US4525256A (en) * 1983-07-01 1985-06-25 Johnson & Johnson Dental Products Company Photopolymerizable composition including catalyst comprising diketone plus 4-(N,N-dimethylamino)benzoic acid or ester thereof
US4587329A (en) * 1984-08-17 1986-05-06 The Dow Chemical Company Dense star polymers having two dimensional molecular diameter
US4952241A (en) * 1986-07-25 1990-08-28 Bayer Aktiengesellschaft (Meth)acylic acid derivatives containing urethane groups
US5545676A (en) * 1987-04-02 1996-08-13 Minnesota Mining And Manufacturing Company Ternary photoinitiator system for addition polymerization
US4746686A (en) * 1987-04-17 1988-05-24 Kerr Manufacturing Company Visible light activated cavity liner
US4857599A (en) * 1988-02-08 1989-08-15 The Dow Chemical Company Modified dense star polymers
US5679794A (en) * 1989-11-07 1997-10-21 Ciba-Geigy Corporation Polymer stabilizers containing both hindered amine and hydroxylamine moieties
US5709548A (en) * 1990-02-23 1998-01-20 Minnesota Mining And Manufacturing Company Dental crown liner composition and methods of preparing provisional applications
US5274064A (en) * 1990-03-23 1993-12-28 Imperial Chemical Industries Plc Star polymers containing hydrolysable group-bearing silicon atoms
US5308886A (en) * 1990-04-20 1994-05-03 Japan Institute Of Advanced Dentistry Photosetting resin for making strong, tough resin articles
US5395883A (en) * 1990-09-28 1995-03-07 General Electric Company Thermoplastic resin compositions containing polyphenylene ethers and polyesters
US5530092A (en) * 1992-01-13 1996-06-25 Dsm N.V. Dendritic macromolecule and the preparation thereof
US5418301A (en) * 1992-02-26 1995-05-23 Perstorp Ab Dendritic macromolecule and process for preparation thereof
US5456602A (en) * 1993-01-29 1995-10-10 Gc Corporation Dental bonding
US5955514A (en) * 1993-04-19 1999-09-21 Dentsply Research & Development Corp. Dental composition and method
US5486548A (en) * 1993-07-21 1996-01-23 Bayer Aktiengesellschaft Acrylates and methacrylates based on cyclohexyldiphenols
US5624976A (en) * 1994-03-25 1997-04-29 Dentsply Gmbh Dental filling composition and method
US5834118A (en) * 1994-09-08 1998-11-10 Neste Oy Of Keilaniemi Radiation curable resins comprising hyperbranched polyesters
US5468789A (en) * 1994-09-12 1995-11-21 General Electric Company Method for making radiation curable silicon containing polyacrylate hardcoat compositions and compositions made thereby
US5814681A (en) * 1994-10-13 1998-09-29 Kuraray Co., Ltd. Restorative composition for hard tissue and dispensing apparatus therefor
US5886064A (en) * 1994-12-08 1999-03-23 Ivoclar Ag Fine-grained polymerizable compositions flowable under pressure or shear stress
US6025114A (en) * 1995-03-11 2000-02-15 Zeneca Limited Liquid photocurable compositions
US5847020A (en) * 1995-07-05 1998-12-08 Den-Mat Corporation Dental adhesive comprising a homogeneous mixture of an unsaturated monomer a coupling agent a crosslinking agent and a photoinitiator
US5767170A (en) * 1995-07-05 1998-06-16 Den-Mat Corporation Dental adhesive comprising an unsaturated monomer, a coupling agent, a crosslinker, leachable fluoride and a photoinitiator
US6031016A (en) * 1995-07-05 2000-02-29 Den-Mat Corporation Dental adhesive
US5847025A (en) * 1996-01-12 1998-12-08 Ivoclar Ag Light-curing composite material
US5985958A (en) * 1996-01-12 1999-11-16 Ivoclar Ag Light-curing composite material
US5914379A (en) * 1996-06-05 1999-06-22 Basf Aktiengesellschaft Compression of ethylenically unsaturated monomers
US6136885A (en) * 1996-06-14 2000-10-24 3M Innovative Proprerties Company Glass ionomer cement
US6184339B1 (en) * 1996-11-14 2001-02-06 The United States Of America As Represented By The Secretary Of The Commerce High strength polymeric networks derived from (meth) acrylate resins with organofluorine content and process for preparing same
US5969000A (en) * 1997-01-17 1999-10-19 Jeneric Pentron Incorporated Dental resin materials
US6121344A (en) * 1998-06-19 2000-09-19 Kerr Corporation Optimum particle sized hybrid composite
US6030606A (en) * 1998-06-22 2000-02-29 3M Innovative Properties Company Dental restoratives comprising Bis-EMA6

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040220291A1 (en) * 2000-08-11 2004-11-04 Uwe Walz Polyaminoester and their application in dental compositions

Also Published As

Publication number Publication date
DE60120416T2 (en) 2006-12-14
US20040220291A1 (en) 2004-11-04
WO2002013767A2 (en) 2002-02-21
EP1307172B1 (en) 2006-06-07
DE60120416D1 (en) 2006-07-20
US20020045677A1 (en) 2002-04-18
US6734223B2 (en) 2004-05-11
JP4989011B2 (en) 2012-08-01
CA2418278A1 (en) 2002-02-21
JP2004506000A (en) 2004-02-26
EP1307172A2 (en) 2003-05-07
WO2002013767A3 (en) 2002-07-04

Similar Documents

Publication Publication Date Title
US6734223B2 (en) Polyaminoester and their application in dental compositions
US7541393B2 (en) Composition containing a polymerizable reducing agent, kit, and method
US7173074B2 (en) Composition containing a polymerizable reducing agent, kit, and method
US7141616B2 (en) Radically curable urethane prepolymers and their use in dental materials
US4920188A (en) Curable compositions
US8292625B2 (en) Radically curable urethane dimethacrylates and compositions thereof for tougher dental prosthetics
US20070043141A1 (en) Free-radical initiator systems containing enzymes, compositions, and methods
ES2597904T3 (en) Carbamate methacrylate monomers and their use in dental applications
JPH07258018A (en) Thermosetting composition used as dental material
US8455566B2 (en) Materials leading to improved dental composites and dental composites made therefrom
US20050124762A1 (en) Dental compositions containing core-shell polymers with low modulus cores
JP2000204069A (en) Polymerizably unsaturated bond-containing n-substituted amide compound
US7501457B2 (en) Dental materials based on multicyclic allyl sulphides
JP4986437B2 (en) Dental curable composition
JP2004300066A (en) Dental material and dental composition
WO2005090281A1 (en) (meth)acrylic compound and use thereof
JP2005126398A (en) Antibacterial dental composition
EP3955881A2 (en) Dental composition

Legal Events

Date Code Title Description
STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载