JP2009544762A - スルホニウム反応開始剤、製造方法及びカチオン重合性組成物の使用方法 - Google Patents
スルホニウム反応開始剤、製造方法及びカチオン重合性組成物の使用方法 Download PDFInfo
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- JP2009544762A JP2009544762A JP2008524169A JP2008524169A JP2009544762A JP 2009544762 A JP2009544762 A JP 2009544762A JP 2008524169 A JP2008524169 A JP 2008524169A JP 2008524169 A JP2008524169 A JP 2008524169A JP 2009544762 A JP2009544762 A JP 2009544762A
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- TVWTZAGVNBPXHU-FOCLMDBBSA-N dioctyl (e)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCC TVWTZAGVNBPXHU-FOCLMDBBSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- FGTVYMTUTYLLQR-UHFFFAOYSA-N n-ethyl-1-phenylmethanesulfonamide Chemical compound CCNS(=O)(=O)CC1=CC=CC=C1 FGTVYMTUTYLLQR-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical compound [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dental Preparations (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
(式中、X-は、非又は低配位アニオンであり、R1、R2、R3及びR4は、独立して直鎖、環状若しくは分枝状C1〜C20アルキル又はアルキレン基である)、アルキル又はアルキレン基に包含されるメチレン基の1つ以上を−CO−、−CONH−、−CON(CH3)−、−S−及び/又は−O−で置換でき、R1、R2、R3及び/又はR4が、2つ又はそれ以上の構造要素を結合する橋かけ要素として作用できることを特徴とする少なくとも1つの構造要素を含む反応開始剤に関する。
又、本発明は、反応開始剤を製造する方法、反応開始剤を含む硬化性組成物、硬化性組成物を製造する方法、カチオン硬化性組成物及び発明の反応開始剤を備えるキット、並びに種々の用途、特に歯科分野において反応開始剤又は反応開始剤を含む硬化性組成物を使用する方法に関する。
Description
X-は、非又は低配位アニオンであり、
R1、R2、R3及びR4は、独立して直鎖、環状若しくは分枝状C1〜C20アルキル又はアルキレン基である)の少なくとも1つの構造要素を含む反応開始剤であって、メチレン基の1つ以上を−CO−、−CONH−、−CON(CH3)−、−S−及び/又は−O−で置換でき、
R1、R2、R3及び/又はR4が、2つ又はそれ以上の構造要素を結合する橋かけ要素として作用できる、反応開始剤を提供する。
R1、R2、R3及びR4は、独立して直鎖、環状若しくは分枝状C1〜C20アルキル又はアルキレン基であり、メチレン基の1つ以上を−CO−、−CONH−、−CON(CH3)−、−S−及び/又は−O−で置換できる。
実施例2/反応開始剤−2:
実施例3/反応開始剤−3:
実施例4/反応開始剤−4:
実施例5/反応開始剤−5:
実施例6/反応開始剤−6:
実施例7/反応開始剤−7:
実施例8/反応開始剤−8:
実施例9/反応開始剤−9:
実施例10/反応開始剤−10:
実施例11/反応開始剤−11:
実施例12/反応開始剤−12:
実施例13/反応開始剤−13:
実施例14/反応開始剤−14:
実施例15/反応開始剤−15:
実施例16/反応開始剤−16:
実施例17/反応開始剤−17:
Eq=530.32g(MW繰返し単位=530.32g)
実施例18/反応開始剤−18:
Eq=603.59g(MW繰返し単位=603.59g)
実施例19/反応開始剤−19:
Eq=502.46g(MW繰返し単位=502.46g)
実施例20/反応開始剤−20:
実施例21/反応開始剤−21:
実施例22/反応開始剤−22:
実施例23/反応開始剤−23:
実施例24/反応開始剤−24:
実施例25/反応開始剤−25:
又、本発明は、
a)グルタコネート、好ましくはグルタコン酸エステルをチオール化合物と反応させてスルフィドを得る工程と、
b)任意に、工程a)のスルフィド化合物をエステル交換反応又は重縮合反応でアルコールと反応させる工程と、
c)工程a)又は工程b)のスルフィド化合物をアルキル化試薬と反応させスルホニウム化合物を得る工程とを備える反応開始剤又は発明の反応開始剤を製造する方法を提供する。
工程a)のグルタコネートをチオールと反応させスルフィド化合物を得る工程と、
工程b)のスルフィド化合物をアルキル化試薬と反応させスルホニウム化合物を得る工程とを備える反応開始剤又は発明の反応開始剤を製造する他の方法。
式B
工程1から得られたスルフィドは、約2モルのアルコール(又は約1モルのジオール)、触媒としての酸又は塩基、及び任意に、溶媒と混合できる。
フラスコを窒素又はアルゴンアオスフィア(aosphere)(商標)等の不活性ガスアオスフィア(商標)の状態に設定後、過剰のアルキル化剤、例えばトリエチルオキソニウムテトラフルオロボレート、エチルトリフレート又はメチルトリフレートをフラスコ内に定置する。任意に、溶媒を添加し、混合物を攪拌してスラリー又は溶液を生成する。
Rは、H、C1〜C12アルキル、C2〜C12アルケニル、C2〜C12アルキニル、C7〜C15アルキルアリール、C7〜C15アリールアルキル又はC3〜C12シクロアルキルを示し、水素原子は、Cl若しくはFにより置換でき及び/又は約炭素原子数5までは、O、CO、N若しくはSから選択される原子又は原子の基で置換でき、
Eは、C1〜C18分枝又は非分枝炭化水素鎖を示し、約炭素原子数5までは、O、CO、N若しくはSから選択される原子又は原子の基で置換でき、
Gは、C(O)O、C(O)NR、C(O)若しくはC(O)C(O)、m=1〜10を有するC(O)(CH2)mC(O)、又はCH2から選択される基を示し、
Lは、x=0又は1を有するO、S、又はNRを示す)により表わすことができる。
構成成分(B):約1重量%〜約15重量%
構成成分(C):約0重量%〜約80重量%
構成成分(D):約0重量%〜約89重量%
硬化後の硬化性組成物は、好ましくは少なくとも1つ、好ましくは2つ又はそれ以上の下記特性を満足する。
硬化性組成物は、ISO4823:2000による軽粘りタイプ材料(タイプ3)からパテ材料(タイプ0)までの種々の粘性の材料を提供するよう処方できる。
−上記したカチオン硬化性化合物を含む構成成分(A)及び上記した発明の反応開始剤を含む構成成分(B)を提供し、
−構成成分(A)と構成成分(B)を混合する硬化性組成物の製造法に関する。
−組成物の構成成分を提供する工程と、
−構成成分を混合する工程と、
−組成物を表面に塗布する工程と、
−組成物を固定する工程とを使用して適用できる。
引張り強度(MPa)及び破断点伸び(%)
引張り強度及び破断点伸びは、ドイツ工業規格(DIN)又は欧州規格(EN)法#53504(形状S2、200mm/分)によりユニバーサル・プルフマシン(Universalprufmaschine)ズウィック(Zwick)Z020(ドイツ、アルム(Ulm)にあるズウィック社((Zwick GmbH &Co))を使用して測定した。
ショアA硬度は、ドイツ工業規格(DIN)法#53505により測定した。硬度を測定する前に硬化性組成物を24時間、23℃及び周囲湿度で硬化させた。
A アセチルトリ−n−ブチルシトレート(CAS 77−90−7)
B アセチルトリ−n−ヘキシルシトレート(CAS 24817−92−3)
C アセチルトリ−2−エチルヘキシルシトレート(CAS 144−15−0)
使用した反応開始剤:
上記反応開始剤1〜25の式を参照のこと。
製造実施例1(反応開始剤−3)
組成物実施例1〜16には、カチオン開環重合の反応開始剤として実施例1〜XXに記載したスルホニウム化合物を使用した中間粘り稠度を有する印象材を記載する。
米国特許第4,167,618号における反応開始剤実施例41
上記したように触媒ペーストにスルホニウム化合物を配合し、ベースペーストを混合して歯科用印象材を生成した。実施例17〜26において、又、印象材は、実施例1〜16の場合のような中間粘り稠度であった。しかしながら、系は、実施例17〜26で異なり、そこではより多い量の二官能性アジリジノポリエーテルを使用した。
米国特許第4,167,618号における反応開始剤実施例41
Claims (16)
- 下記式
X-は、非又は低配位アニオンであり、
R1、R2、R3及びR4は、独立して直鎖、環状若しくは分枝状C1〜C20アルキル又はアルキレン基である)を特徴とする少なくとも1つの構造要素を含む反応開始剤であって、アルキル又はアルキレン基に包含されるメチレン基の1つ以上を−CO−、−CONH−、−CON(CH3)−、−S−及び/又は−O−で置換でき、
R1、R2、R3及び/又はR4が、2つ又はそれ以上の構造要素を結合する橋かけ要素として作用できる、反応開始剤。 - 約250〜約25,000g/モルの範囲の分子量を有し、前記分子量が、モノマーについてはMWで表わされ、オリゴマー及び/又はポリマーについてはMn(数平均分子量)で表わされる、請求項1に記載の反応開始剤。
- 約300〜約800g/モルの範囲のスルホニウム当量Eqを有し、Eqが、前記反応開始剤の分子量を前記反応開始剤中に存在するスルホニウム基数で除して求められる、請求項1又は2に記載の反応開始剤。
- X-が、BF4 -、CF3SO3 -、SbF6 -、AsF6 -、又は2,5−ジクロロ−ベンゼンスルホネートから成る群から選択される、請求項1〜3のいずれかに記載の反応開始剤。
- R1、R2が、互いに独立してメチル、エチル、n−プロピル、2−プロピル、n−ブチル、第二級ブチル、第三級ブチル、n−ペンチル、n−ヘキシル、n−ヘプチル又はn−オクチルであり、R1及びR2の1つ以上のメチレン基を−CO−、−CONH−、−CON(CH3)−、−S−及び/又は−O−で置換でき、
R3が、メチル、エチル、n−プロピル、2−プロピル、n−ブチル、第二級ブチル、第三級ブチル、n−ペンチル、n−ヘキシル、n−ヘプチル又はn−オクチルであり、
R4が、R3、n−ノニル、n−デシル、n−ウンデシル又はn−ドデシルであり、このアルキル鎖の1つ以上のメチレン基を−CO−、−CONH−、−CON(CH3)−、−S−及び/又は−O−で置換できる、請求項1〜4のいずれかに記載の反応開始剤。 - a)グルタコネートをチオール化合物と反応させスルフィド化合物を得る工程と、
b)任意に、工程a)の前記スルフィド化合物をエステル交換反応又は重縮合反応でアルコールと反応させる工程と、
c)工程a)又はb)の前記スルフィド化合物をアルキル化試薬と反応させスルホニウム化合物を得る工程とを備える、反応開始剤を製造する方法。 - a)グルタコン酸をエステル交換反応又は重縮合反応でアルコールと反応させる工程と、
b)工程a)の前記グルタコネートをチオールと反応させスルフィド化合物を得る工程と、
c)工程b)の前記スルフィド化合物をアルキル化試薬と反応させスルホニウム化合物を得る工程とを備える、反応開始剤を製造する方法。 - (A)構成成分(A)として少なくとも1つのカチオン重合性化合物と、
(B)構成成分(B)として請求項1〜4のいずれかに記載の少なくとも1つの反応開始剤と、
(C)任意に、構成成分(C)として充填剤と、
(D)任意に、構成成分(D)としてその他の添加剤とを含む、硬化性組成物。 - 前記カチオン重合性化合物が、アジリジン基を含有する、請求項8に記載の硬化性組成物。
- 構成成分(A)〜(D)を下記の量、
構成成分(A):約10重量%〜約90重量%、
構成成分(B):約1重量%〜約30重量%、
構成成分(C):約0重量%〜約80重量%、及び
構成成分(D):約0重量%〜約89重量%、
含有する、請求項8又は9に記載の硬化性組成物。 - 下記特性、
−ショアA硬度(DIN53505、混合後24時間で測定)約40〜80以上、
−DIN EN 53504(MPa)による引張り強度約0.4以上、及び
−DIN EN 53504(%)による破断点伸び約50以上、
の少なくとも1つを有する、請求項8〜10のいずれかに記載の硬化性組成物。 - 構成成分(A)、任意に、構成成分(C)及び/又は構成成分(D)を含む部分Iと、
構成成分(B)、任意に、構成成分(C)及び/又は構成成分(D)を含む部分IIとを備える部分のキットであって、
構成成分(A)〜(D)が、上記請求項8〜11のいずれかに記載のように定義される、部分のキット。 - 構成成分(A)及び構成成分(B)を提供し、
構成成分(A)と構成成分(B)を混合する、請求項8〜11のいずれかに記載の硬化性組成物を製造する方法であって、
構成成分(A)及び構成成分(B)が、上記請求項8〜11のいずれかに記載のように定義される、製造方法 - カチオン重合性物質の硬化プロセスを開始させる、請求項1〜4のいずれかに記載の反応開始剤の使用方法。
- コーティング、封止、成型、接着又は印象材の作製のために、請求項9又は11に記載の硬化性組成物を使用する方法。
- 精密印象材、位置印象材、咬合記録材、複製材、又は模型材から選択される歯科用材料を製造するために、請求項9又は11に記載の硬化性組成物を使用する方法。
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EP05016531A EP1748057A1 (en) | 2005-07-29 | 2005-07-29 | Sulfonium initiators, process for production and use in cationic polymerizable compositions |
PCT/US2006/029311 WO2007016295A1 (en) | 2005-07-29 | 2006-07-27 | Sulfonium initiators, process for production and use in cationic polymerizable compositions |
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EP (2) | EP1748057A1 (ja) |
JP (1) | JP5077892B2 (ja) |
KR (1) | KR101345092B1 (ja) |
CN (1) | CN101278009B (ja) |
AT (1) | ATE412703T1 (ja) |
AU (1) | AU2006275729A1 (ja) |
CA (1) | CA2617089A1 (ja) |
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JP2019107244A (ja) * | 2017-12-19 | 2019-07-04 | クラレノリタケデンタル株式会社 | 歯科用印象型の製造方法 |
JP2022521846A (ja) * | 2019-04-02 | 2022-04-12 | スリーエム イノベイティブ プロパティズ カンパニー | 構造用接着剤組成物の硬化性前駆体を製造するプロセス |
JP2022521847A (ja) * | 2019-04-02 | 2022-04-12 | スリーエム イノベイティブ プロパティズ カンパニー | 構造用接着剤組成物の硬化性前駆体 |
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US10729622B2 (en) | 2015-05-29 | 2020-08-04 | 3M Innovative Properties Company | Process for taking a dental impression and curable composition for use in a dental impressioning and retraction process |
US10952933B2 (en) | 2015-07-07 | 2021-03-23 | 3M Innovative Properties Company | Kit of parts containing a cationically hardenable composition and use as dental retraction material |
CN106349134A (zh) * | 2016-07-27 | 2017-01-25 | 武汉理工大学 | 无溶剂制备含氟锍盐的方法 |
EP3650485A1 (en) | 2018-11-06 | 2020-05-13 | 3M Innovative Properties Company | Acid-curable composition |
EP3650486A1 (en) | 2018-11-06 | 2020-05-13 | 3M Innovative Properties Company | Acid-curable composition |
WO2020104889A1 (en) | 2018-11-20 | 2020-05-28 | 3M Innovative Properties Company | Curable composition containing a polyether-modified polydimethyl siloxane |
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US20080200585A1 (en) | 2008-08-21 |
WO2007016295A1 (en) | 2007-02-08 |
KR101345092B1 (ko) | 2013-12-26 |
EP1913090A1 (en) | 2008-04-23 |
ATE412703T1 (de) | 2008-11-15 |
DE602006003441D1 (de) | 2008-12-11 |
JP5077892B2 (ja) | 2012-11-21 |
CN101278009A (zh) | 2008-10-01 |
EP1913090B1 (en) | 2008-10-29 |
EP1748057A1 (en) | 2007-01-31 |
AU2006275729A1 (en) | 2007-02-08 |
CN101278009B (zh) | 2011-05-18 |
US7947757B2 (en) | 2011-05-24 |
CA2617089A1 (en) | 2007-02-08 |
KR20080039958A (ko) | 2008-05-07 |
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