WO2005108978A1 - Method for monitoring a polymerization in a three-dimensional sample - Google Patents
Method for monitoring a polymerization in a three-dimensional sample Download PDFInfo
- Publication number
- WO2005108978A1 WO2005108978A1 PCT/US2005/012604 US2005012604W WO2005108978A1 WO 2005108978 A1 WO2005108978 A1 WO 2005108978A1 US 2005012604 W US2005012604 W US 2005012604W WO 2005108978 A1 WO2005108978 A1 WO 2005108978A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sample
- polymerization
- array
- samples
- captured
- Prior art date
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- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000248 cariostatic effect Effects 0.000 description 1
- 235000020226 cashew nut Nutrition 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- KSDIHKMNSYWRFB-UHFFFAOYSA-N chrysen-2-amine Chemical compound C1=CC=CC2=CC=C3C4=CC=C(N)C=C4C=CC3=C21 KSDIHKMNSYWRFB-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004320 controlled atmosphere Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 210000003074 dental pulp Anatomy 0.000 description 1
- 239000004851 dental resin Substances 0.000 description 1
- 210000004268 dentin Anatomy 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- HDERJYVLTPVNRI-UHFFFAOYSA-N ethene;ethenyl acetate Chemical group C=C.CC(=O)OC=C HDERJYVLTPVNRI-UHFFFAOYSA-N 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- BTOIAAYVFNXNPA-UHFFFAOYSA-N ethenyl 2-chloropropanoate Chemical compound CC(Cl)C(=O)OC=C BTOIAAYVFNXNPA-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000012682 free radical photopolymerization Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000007496 glass forming Methods 0.000 description 1
- 238000005816 glass manufacturing process Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000005026 oriented polypropylene Substances 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
- 229960003868 paraldehyde Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000005365 phosphate glass Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000068 pit and fissure sealant Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000003211 polymerization photoinitiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- GGYFMLJDMAMTAB-UHFFFAOYSA-N selanylidenelead Chemical compound [Pb]=[Se] GGYFMLJDMAMTAB-UHFFFAOYSA-N 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- SPVXKVOXSXTJOY-UHFFFAOYSA-O selenonium Chemical class [SeH3+] SPVXKVOXSXTJOY-UHFFFAOYSA-O 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/44—Resins; Plastics; Rubber; Leather
- G01N33/442—Resins; Plastics
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N25/00—Investigating or analyzing materials by the use of thermal means
- G01N25/72—Investigating presence of flaws
Definitions
- the choice of the "initiation surface” and the “monitoring surface(s)" may be arbitrary for any particular sample or array of samples, but it is often convenient to initiate polymerization on an upper, horizontal surface, and monitor the polymerization from one of the substantially perpendicular, vertical surfaces.
- the samples may be considered to have dimensions along arbitrary x, y and z dimensions.
- the z dimension may be considered the vertical dimension, and may be considered normal to the plane of a horizontal initiation surface.
- the sample size is at least 0.5 mm along the z axis which is normal to the polymerization front; i.e. a hypothetical plane along which polymerization advances through the sample.
- Thermoplastic polymers which may be prepared in the present method include but are not limited to polyolefins and copolymers and blends thereof (including metallocene polyolefins, poly(alpha olefins), and ethylene-propylene-diene terpolymers) styrene copolymers and terpolymers, ionomers, ethylene vinyl acetate, polyvinylbutyrate, poly vinyl chloride, fluorocarbon elastomers, other fluorine-containing polymers, polyester polymers and copolymers, polyamide polymers and copolymers, polyurethanes, polycarbonates, polyketones, and polyureas.
- polyolefins and copolymers and blends thereof including metallocene polyolefins, poly(alpha olefins), and ethylene-propylene-diene terpolymers
- styrene copolymers and terpolymers ion
- Still other polymers include fluorine-containing polymers including polymers and copolymers of tetrafluoroethylene with one or more other monomers such as perfluoro(methyl vinyl)ether, hexafluoropropylene, perfluoro(propyl vinyl)ether; copolymers of tetrafluoroethylene with ethylenically unsaturated hydrocarbon monomers such as ethylene, or propylene.
- Representative olefins are ethylene, propylene, 1- and 2-butene.
- Thermoset polymers that may be prepared include those derived from phenolic resins, epoxy resins, vinyl ester resins, (meth)acrylate resins, vinyl ether resins, urethane resins, cashew nut shell resins, napthalenic and phenolic resins, epoxy modified phenolic resins, silicone (hydrosilane and hydrolyzable silane) resins, polyimide resins, urea formaldehyde resins, methylene dianiline resins, methyl pyrrolidinone resins, acrylate and methacrylate resins, isocyanate resins, unsaturated polyester resins, and mixtures thereof.
- Polymeric epoxides include linear polymers having terminal epoxy groups (e.g., a diglycidyl ether of a polyoxyalkylene glycol), polymers having skeletal oxirane units (e.g., polybutadiene polyepoxide), and polymers having pendent epoxy groups (e. g., a glycidyl methacrylate polymer or copolymer). Phenolic resins may also be prepared.
- Oxetane (oxacyclobutane) rings behave somewhat like epoxy (oxirane) rings in that catalysts and/or co-curatives, sometimes referred to as crosslinking agents, can be used to open the ring and link two or more chains together to form a crosslinked polymer.
- catalysts and/or co-curatives sometimes referred to as crosslinking agents
- crosslinking agents can be used to open the ring and link two or more chains together to form a crosslinked polymer.
- polycarboxylic acid anhydrides and other polyfunctional compounds such as polyammes, polycarboxylic acids, polymercaptans, polyacid halides, or the like are capable of linking two or more oxetane sites just as epoxy sites are linked by epoxide co-curatives.
- the result is an increased amount of three-dimensional structure in the crosslinked or cured polymer, and hence an increased amount of rigidity of the polymer structure.
- Semi-IPNs comprising uncured epoxy resins as the major constituent and, as minor constituents, butadiene-acrylonitrile rubber (G.B. Patent No. 736,457), a crosslinked elastomeric latex (G.B. Patent No. 1,247,116) have been described.
- Semi-interpenetrating polymer networks of polyolefins and tri-epoxy resins have been studied by Negmatov et at., Uzb. Khim. Zh., 1990 (6), 65-7; CA 115:93689n (1991). No curatives, amounts of components, or processes of making the IPN are disclosed.
- ethylenically unsaturated vinyl monomers or oligomers include: styrene, alkylstyrenes, halostyrenes, acrylonitrile, vinyl chloride, vinylidene chloride; vinyl ethers, such as 1,4-cyclohexanedimethanol divinyl ether (CHVE) and diethyleneglycol divinyl ether (DVE); vinyl esters, such as vinyl acetate; and N-vinyl derivatives, such as N- vinylpyrrolidone and N-vinyl formamide.
- CHVE 1,4-cyclohexanedimethanol divinyl ether
- DVE diethyleneglycol divinyl ether
- vinyl esters such as vinyl acetate
- N-vinyl derivatives such as N- vinylpyrrolidone and N-vinyl formamide.
- ethylenically unsaturated acrylic monomers or oligomers include: alkyl or hydroxyalkyl (meth)acrylates such as methyl(meth)acrylate, ethyl(meth)acrylate, butyl(meth)acrylate, (meth)acrylamide, 2-ethylhexylacrylate, 2-hydroxyethyl acrylate, isobomyl acrylate, glycerol diacrylate, glycerol triacrylate, tetraethylene glycol diacrylate, 1,4- butanediol diacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, trimethylolpropane triacrylate, 1,2,4-butanetriol trimethylacrylate, 1,4- cyclo
- U.S. Pat. No. 5,545,676 (Palazzotto et al.).
- the three-component system includes an iodonium salt (i.e., a diaryliodonium salt), a sensitizer, and a donor.
- iodonium salt i.e., a diaryliodonium salt
- sensitizer i.e., a sensitizer
- donor iodonium salt
- Each photoinitiator component is discussed in U.S. Pat. No. 5,545,676, column 2, line 27, to column 4, line 45.
- Other useful free-radical initiators include the class of acylphosphine oxides, as described in European Pat. Application No. 173567, U.S. Pat. No. 4,737,593 and United Kingdom Patent No. GB 2,310,
- Suitable sensitizers are believed to include compounds in the following categories: ketones, coumarin dyes (e.g., ketocoumarins), xanthene dyes, acridine dyes, thiazole dyes, thiazine dyes, oxazine dyes, azine dyes, aminoketone dyes, porphyrins, aromatic polycyclic hydrocarbons, p-substituted aminostyryl ketone compounds, aminotriaryl methanes, merocyanines, squarylium dyes and pyridinium dyes.
- ketones coumarin dyes (e.g., ketocoumarins), xanthene dyes, acridine dyes, thiazole dyes, thiazine dyes, oxazine dyes, azine dyes, aminoketone dyes, porphyrins, aromatic polycyclic hydrocarbons, p-substituted aminostyryl ketone
- the sample(s) may be mounted on or in contact with a heated container, or the sample may be in contact with a heated sample stage, such as a programmable hotplate.
- the samples may be contained within a heated chamber having an IR transmissive window, such as a quartz window, for capture of the thermographic profile.
- the samples may be exposed to a thermal gradient by use of a gradiant heat source.
- the thermographic profile of the apparatus may be captured and subtracted from that of the polymerizable sample.
- a "blank" sample comprising the composition of interest, but lacking an initiator, is subjected to the reaction conditions, the thermographic profile captured, and then compared with the polymerizable sample.
- Useful photoacid generators include ionic photoacid generators, including onium salts and organometallic salts, such as iron arene complexes; and nonionic photoacid generators, including organosilanes, latent sulfonic acids and other miscellaneous non-ionic compounds, such as halomethyl triazines (such as those described in U.S. Pat. No. 3,987,037) and chlorinated acetophenones.
- Photoacid generators are known and reference may be made to J. V. Crivello and K. Dietliker, Chemistry and Technology of UV and EB Formulation for Coatings, Inks and Paints, vol. HI, SITA Technology Ltd., London, 1998. Further reference may be made to Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition, Supplement Volume, John Wiley and
- Useful thermal acid generators include any polymeric or non-polymeric compounds that release one or more molecules of acid on exposure to thermal energy.
- Useful thermal acid generators have an activation temperature of less than the decomposition temperature of the vinyl alcohol polymer and generally have an activation temperature of 200°C or less, preferably 170 ° C or less. Additionally, the thermal acid generator should have an activation temperature at least 20 ° C above the melt temperature of the donor layer, if coated from the melt.
- activation temperature is that temperature at which the thermal release of the incipient acid by the thermal acid generator in the donor layer occurs. Typically the thermal acid generator will have an activation temperature from about 50°C to about 170°C.
- Such free radically polymerizable materials include mono-, di- or poly-acrylates and methacrylates such as methyl acrylate, methyl methacrylate, ethyl acrylate, isopropyl methacrylate, n-hexyl acrylate, stearyl acrylate, allyl acrylate, glycerol diacrylate, glycerol triacrylate, ethyleneglycol diacrylate, diethyleneglycol diacrylate, triethyleneglycol dimethacrylate, 1,3-propanediol diacrylate, 1,3-propanediol dimethacrylate, trimethylolpropane triacrylate, 1,2,4-butanetriol trimethacrylate, 1,4- cyclohexanediol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, sorb
- U.S. Pat. No. 5,545,676 (Palazzotto et al.).
- the three-component system includes an iodonium salt (i.e., a diaryliodonium salt), a sensitizer, and a donor.
- iodonium salt i.e., a diaryliodonium salt
- sensitizer i.e., a sensitizer
- donor iodonium salt
- Each photoinitiator component is discussed in U.S. Pat. No. 5,545,676, column 2, line 27, to column 4, line 45.
- Other useful free-radical initiators include the class of acylphosphine oxides, as described in European Pat. Application No. 173,567, U.S. Pat. No. 4,737,593 and United Kingdom Patent No. GB 2,310,
- the filler is preferably finely divided.
- the filler can have a unimodial or polymodial (e.g., bimodal) particle size distribution.
- the maximum particle size (the largest dimension of a particle, typically, the diameter) of the filler is less than about 10 micrometers, and more preferably
- the average particle size of the filler is less than about 3.0 micrometers, and more preferably less than about 0.6 micrometer.
- the filler can be an inorganic material. It can also be a crosslinked organic material that is insoluble in the resin system, and is optionally filled with inorganic filler. The filler should in any event be nontoxic and suitable for use in the mouth.
- the filler can be radiopaque or radiolucent.
- the filler is also substantially insoluble in water.
- the glass can be made from a melt containing fluoride, alumina, and other glass-forming ingredients using techniques familiar to those skilled in the FAS glassmaking art.
- the FAS glass preferably is in the form of particles that are sufficiently finely divided so that they can conveniently be mixed with the other cement components and will perform well when the resulting mixture is used in the mouth.
- the filler is added in amounts sufficient to provide a hardenable composition having desirable mixing and handling properties before hardening, and good performance after hardening.
- the filler represents no greater than about 90 wt-%, more preferably no greater than about 85 wt-%, and most preferably no greater than about 80 wt-%, of the total weight (including water) of the hardenable composition components.
- the detectors should further have a temperature resolution of ⁇ 0.5°C, preferably ⁇ 0.1°C and most preferably ⁇ 0.02°C.
- One or more detectors may be used.
- Pyrometers are non-contact temperature sensors that measure temperature from the amount of thermal electromagnetic radiation received from a spot on the sample. This group of sensors includes both spot or "point" measuring devices in addition to line measuring radiation thermometers, which produce 1-D and, with known relative motion, can produce 2-D temperature distributions, and thermal imaging, or area measuring, thermometers which measure over an area from which the resulting image can be displayed as a 2-D temperature map of the region viewed.
- IR optical pyrometers are sensitive to infrared wavelengths and typically convert the input wavelength to an optical or electronic output by means of an IC, resistance temperature detector or thermocouple.
- infrared optical pyrometers are not to be confused with other optical pyrometers that measure temperatures of very hot objects (>700°C) based upon their visible light emission due to incandescence.
- Useful IR pyrometers will measure infrared output between 6-14 micrometers in the IR and generally have a useful temperature range of -20 to 538°C; well beyond that required for measuring the exothermicity of polymerizations using the method of the invention.
- One useful IR pyrometer is an Omega Industrial IR thermometer (OS552-V1-6).
- Standard features include the ability to subtract one image from another, or from a string of images to create a "normalized” video, identification of maximum and minimum temperatures within an image (or a defined region or line), the ability to track the temperature of a given pixel through a sequence of images (a video) generating a time/temperature profile, a variety of false color palettes, and many other functions.
- the software allows one to map a selected sample area, and to plot the data as a function of time.
- the IR detector array is normally oriented substantially perpendicular to the surface of initiation ("initiation surface") of the polymer sample; that is, if the sample is initiated on a first surface, the IR detector is oriented to monitor a second surface substantially perpendicular to the first surface.
- sample 10 Polymerization of sample 10 is initiated with radiation source 14, such as a UV source, impinging on the top surface of sample 10, with the radiation source 14 connected to power source 16.
- the radiation (such as UV) may be constrained to all or a portion of the upper, horizontal surface of sample 10 (not shown).
- the thermographic profile of sample 10 is captured with IR detector array 18, which is illustrated as interfaced with computer 20 for data collection and analysis.
- IR detector 18 is preferably an IR digital camera, wherein each pixel may be "mapped" to a point on the surface of sample 10 for capture of multiple points. As shown, IR detector 18 is oriented substantially perpendicular to the initiation surface of sample 10.
- thermographic profile of sample 10 may be captured (along with any container) for subtraction from later obtained thermographic profiles during polymerization. Data obtained may be collected, and plotted by computer 20. Images may be captured as a function of time, to create a "normalized" video, where the progression of the polymerization front through the sample, and any defects may be noted. This sample may be compared with other samples that vary as to composition of monomers, initiator, exposure time, temperature, etc.
- Figure 2 illustrates a particularly useful sample configuration 200.
- Example 4 The same procedure used in Example 3 was utilized except that the thermal imaging camera was a CMC Electronics TVS-8500 IR Camera. A sample cylinder of Z250 was prepared with dimensions 10.9 millimeters x 6.1 millimeters. This cylinder was irradiated from the top as described in Example 3. The temperatures at these various points as a function of irradiation time are shown in Table 4. Table 4
- Example 7 For Example 7, a one percent by weight solution of VAZO 67 was prepared in HEMA. A small quartz cup 7.5 mm in diameter and approximately 8.5 mm deep (approximately 0.36 cm 3 internal volume) was loaded with the solution. A strip of aluminum foil tape (3M, St. Paul, MN) was placed across the top of the cup and the whole transferred to a hot plate maintained at 87-89°C. The cup was imaged at various time intervals with an infrared camera (Prism DS with 25 mm lens, Flir Systems, Boston MA) held at a distance of approximately 28 centimeters (11 inches) for a total of 10 minutes. The time-temperature profile at the midpoint of the cup is shown below in Table 7. The temperature profile at different depths from the top of the cup is presented in Table 8. Table 7
- Example 8 The curing kinetics of a thick section of a curing formulation were studied by recording the heat propagation through the mass using a CMC Electronics TVS-8500 IR thermal imaging camera.
- a sample of Z250 was packed into a cylindrical section (0.7 cm X 0.5 cm) of a drinking straw. This cylinder was irradiated from the top with a dental blue light gun (Model 5560) fitted with an aperture of less than 1 millimeter by wrapping the tip of the light gun in perforated aluminum foil to reduce the intensity of light. The gun was held about 1 millimeter from the top of the cylinder to ensure that there was no irradiation of the sides of the cylinder.
- a dental blue light gun Model 5560
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Abstract
Description
Claims
Priority Applications (3)
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CN2005800137696A CN1950699B (en) | 2004-04-28 | 2005-04-13 | Method for monitoring a polymerization in a three-dimensional sample |
JP2007510778A JP2007534963A (en) | 2004-04-28 | 2005-04-13 | How to monitor polymerization in 3D samples |
EP05746308A EP1740939A1 (en) | 2004-04-28 | 2005-04-13 | Method for monitoring a polymerization in a three-dimensional sample |
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US10/834,305 US7553670B2 (en) | 2004-04-28 | 2004-04-28 | Method for monitoring a polymerization in a three-dimensional sample |
US10/834,305 | 2004-04-28 |
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WO2005108978A1 true WO2005108978A1 (en) | 2005-11-17 |
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PCT/US2005/012604 WO2005108978A1 (en) | 2004-04-28 | 2005-04-13 | Method for monitoring a polymerization in a three-dimensional sample |
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US (1) | US7553670B2 (en) |
EP (1) | EP1740939A1 (en) |
JP (1) | JP2007534963A (en) |
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US20050244975A1 (en) | 2005-11-03 |
EP1740939A1 (en) | 2007-01-10 |
JP2007534963A (en) | 2007-11-29 |
CN1950699B (en) | 2010-09-29 |
US7553670B2 (en) | 2009-06-30 |
CN1950699A (en) | 2007-04-18 |
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