CA1153491A - Abrasion-resistant coating composition - Google Patents
Abrasion-resistant coating compositionInfo
- Publication number
- CA1153491A CA1153491A CA000345431A CA345431A CA1153491A CA 1153491 A CA1153491 A CA 1153491A CA 000345431 A CA000345431 A CA 000345431A CA 345431 A CA345431 A CA 345431A CA 1153491 A CA1153491 A CA 1153491A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- pentaerythritol
- substrate
- product
- polyacrylate
- 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.)
- Expired
Links
- 238000005299 abrasion Methods 0.000 title claims abstract description 48
- 239000008199 coating composition Substances 0.000 title abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 116
- 239000000758 substrate Substances 0.000 claims abstract description 98
- 238000000576 coating method Methods 0.000 claims abstract description 80
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 45
- 229940059574 pentaerithrityl Drugs 0.000 claims abstract description 41
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims abstract description 41
- 229920002678 cellulose Polymers 0.000 claims abstract description 33
- 239000002904 solvent Substances 0.000 claims abstract description 32
- 229920000193 polymethacrylate Polymers 0.000 claims abstract description 22
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000005855 radiation Effects 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 238000005507 spraying Methods 0.000 claims abstract description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001298 alcohols Chemical class 0.000 claims abstract description 6
- 239000011248 coating agent Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 48
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims description 34
- 239000000047 product Substances 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 17
- 235000019441 ethanol Nutrition 0.000 claims description 16
- 229920000515 polycarbonate Polymers 0.000 claims description 15
- 239000004417 polycarbonate Substances 0.000 claims description 15
- -1 alkyl acetates Chemical class 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 229920000728 polyester Polymers 0.000 claims description 11
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 9
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 9
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001913 cellulose Substances 0.000 claims description 7
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 150000005215 alkyl ethers Chemical class 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 5
- 238000011417 postcuring Methods 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 4
- 229920006397 acrylic thermoplastic Polymers 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 claims 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 2
- XYRRJTMWSSGQGR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO.OCC(CO)(CO)CO XYRRJTMWSSGQGR-UHFFFAOYSA-N 0.000 claims 1
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 claims 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 claims 1
- 229940081735 acetylcellulose Drugs 0.000 abstract description 7
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 150000002576 ketones Chemical class 0.000 abstract description 4
- ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 230000003678 scratch resistant effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 19
- 229940070721 polyacrylate Drugs 0.000 description 15
- 239000010408 film Substances 0.000 description 14
- 239000004800 polyvinyl chloride Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 229910000831 Steel Inorganic materials 0.000 description 13
- 238000001723 curing Methods 0.000 description 13
- 229920000915 polyvinyl chloride Polymers 0.000 description 13
- 239000010959 steel Substances 0.000 description 13
- 210000002268 wool Anatomy 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
- 229940063557 methacrylate Drugs 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 7
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 229940090181 propyl acetate Drugs 0.000 description 7
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006748 scratching Methods 0.000 description 6
- 230000002393 scratching effect Effects 0.000 description 6
- 230000008646 thermal stress Effects 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000007 visual effect Effects 0.000 description 6
- 235000010980 cellulose Nutrition 0.000 description 5
- 238000005336 cracking Methods 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229920002301 cellulose acetate Polymers 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- 229960005335 propanol Drugs 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 239000000020 Nitrocellulose Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001680 brushing effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical compound CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 description 3
- 229920001220 nitrocellulos Polymers 0.000 description 3
- 229940079938 nitrocellulose Drugs 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 241001422033 Thestylus Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- SOBZYRBYGDVKBB-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO.OCC(CO)(CO)CO SOBZYRBYGDVKBB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- FJVSXRPDIJPVCC-UHFFFAOYSA-N 2-n-ethenyl-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=C)=N1 FJVSXRPDIJPVCC-UHFFFAOYSA-N 0.000 description 1
- CCCIYAQYQZQDIZ-UHFFFAOYSA-N 6-methylheptan-3-one Chemical compound CCC(=O)CCC(C)C CCCIYAQYQZQDIZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 241000282337 Nasua nasua Species 0.000 description 1
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- LJVWFNQRNPCPGI-UHFFFAOYSA-N acetic acid butanoic acid propyl acetate Chemical compound C(C)(=O)OCCC.C(CCC)(=O)O.C(C)(=O)O LJVWFNQRNPCPGI-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940106135 cellulose Drugs 0.000 description 1
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229960003504 silicones Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
- C08F251/02—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof on to cellulose or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Lubricants (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Sliding-Contact Bearings (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1341879A | 1979-02-21 | 1979-02-21 | |
| US013,418 | 1979-02-21 | ||
| US06/104,351 US4308119A (en) | 1979-02-21 | 1980-01-07 | Abrasion-resistant optical coating composition containing pentaerythritol based polyacrylates and cellulose esters |
| US104,351 | 1980-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1153491A true CA1153491A (en) | 1983-09-06 |
Family
ID=26684814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345431A Expired CA1153491A (en) | 1979-02-21 | 1980-02-12 | Abrasion-resistant coating composition |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4308119A (en, 2012) |
| JP (2) | JPH021162B2 (en, 2012) |
| CA (1) | CA1153491A (en, 2012) |
| FR (1) | FR2449715B1 (en, 2012) |
| GB (1) | GB2056886B (en, 2012) |
| WO (1) | WO1980001805A1 (en, 2012) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4308119A (en) * | 1979-02-21 | 1981-12-29 | Panelgraphic Corporation | Abrasion-resistant optical coating composition containing pentaerythritol based polyacrylates and cellulose esters |
| US4373007A (en) * | 1980-11-03 | 1983-02-08 | Panelgraphic Corporation | [Non-photoinitialio] non-photocatalyzed dipentaerythritol polyacrylate based coating compositions exhibiting high abrasion resistance |
| US4758448A (en) * | 1982-09-07 | 1988-07-19 | Signet Armorlite, Inc. | Coated ophthalmic lenses and method for coating the same |
| DE3443088A1 (de) * | 1984-03-03 | 1985-09-19 | Wolff Walsrode Ag, 3030 Walsrode | Waessrige dispersionen auf basis von cellulosenitraten, verfahren zu ihrer herstellung und ihre verwendung als schnellhaertende ueberzuege |
| US4557980A (en) * | 1984-08-21 | 1985-12-10 | Martin Processing, Inc. | Radiation curable coating for film structure |
| US4958148A (en) * | 1985-03-22 | 1990-09-18 | Elmwood Sensors, Inc. | Contrast enhancing transparent touch panel device |
| US4656202A (en) * | 1985-08-28 | 1987-04-07 | Reliance Universal, Inc. | Acrylated cellulosic furniture coatings |
| US4774035A (en) * | 1986-01-14 | 1988-09-27 | Camelot Industries Corporation | Process of coating an ophthalmic lens |
| US4855184A (en) * | 1988-02-02 | 1989-08-08 | Minnesota Mining And Manufacturing Company | Radiation-curable protective coating composition |
| US5254395A (en) * | 1988-08-23 | 1993-10-19 | Thor Radiation Research, Inc. | Protective coating system for imparting resistance to abrasion, impact and solvents |
| US5114783A (en) * | 1988-08-23 | 1992-05-19 | Thor Radiation Research, Inc. | Protective coating system for imparting resistance to abrasion, impact and solvents |
| US5104692A (en) * | 1990-04-20 | 1992-04-14 | Pilkington Visioncare Holdings, Inc. | Two-layer antireflective coating applied in solution |
| US5906788A (en) * | 1992-10-05 | 1999-05-25 | Cook Composites And Polymers Co. | Dual cure, in-mold process for manufacturing abrasion resistant, coated thermoplastic articles |
| US6235396B1 (en) | 1998-06-26 | 2001-05-22 | Younger Mfg | Optical lens comprising a polyvinylalcohol layer covalently bonded to a bulk lens polymer |
| US6410147B1 (en) | 2000-08-24 | 2002-06-25 | E. I. Du Pont De Nemours And Company | Low gloss crosslinkable coating compositions |
| US7375144B2 (en) * | 2005-06-16 | 2008-05-20 | Eastman Chemical Company | Abrasion resistant coatings |
| EP1884958B1 (en) | 2006-07-31 | 2012-11-21 | Agfa HealthCare NV | Polymer compositions and use thereof as topcoat layers for phosphor or scintillator screens or panels. |
| DE102008055194A1 (de) | 2008-12-30 | 2010-07-08 | Federal-Mogul Wiesbaden Gmbh | Gleitelement |
| JP2020196806A (ja) * | 2019-06-03 | 2020-12-10 | ナトコ株式会社 | 膜形成用樹脂組成物、樹脂膜および樹脂膜を備える物品 |
| US12247133B2 (en) * | 2022-02-17 | 2025-03-11 | Canon Kabushiki Kaisha | Photocurable composition including a reactive polymer |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1552795A (en) * | 1924-06-16 | 1925-09-08 | Eastman Kodak Co | Cellulose-ester composition |
| US2288352A (en) * | 1938-12-24 | 1942-06-30 | Paper Patents Co | Transfer machine |
| US2505067A (en) * | 1947-09-29 | 1950-04-25 | Alexander H Kerr & Co | Catalytic photopolymerization process and compositions |
| US3047422A (en) * | 1956-01-09 | 1962-07-31 | Miehle Goss Dexter Inc | Coating material and method of drying same |
| NL218803A (en, 2012) * | 1956-07-09 | |||
| GB841454A (en) * | 1957-09-16 | 1960-07-13 | Du Pont | Improvements in or relating to photopolymerisable elements |
| US3046127A (en) * | 1957-10-07 | 1962-07-24 | Du Pont | Photopolymerizable compositions, elements and processes |
| US3076723A (en) * | 1958-05-26 | 1963-02-05 | Du Pont | Coating weight determination by means of ultraviolet light |
| NL276329A (en, 2012) * | 1961-03-29 | |||
| US3203802A (en) * | 1962-04-09 | 1965-08-31 | Du Pont | Photopolymerizable composition and element |
| US3149975A (en) * | 1962-07-06 | 1964-09-22 | Du Pont | Photopolymerizable compositions and elements |
| GB1054125A (en, 2012) * | 1963-04-22 | |||
| US3380831A (en) * | 1964-05-26 | 1968-04-30 | Du Pont | Photopolymerizable compositions and elements |
| NL129237C (en, 2012) * | 1965-03-11 | |||
| US3551235A (en) * | 1967-07-10 | 1970-12-29 | Sun Chemical Corp | Radiation-curable compositions |
| US3551311A (en) * | 1967-11-24 | 1970-12-29 | Sun Chemical Corp | Radiation-curable compositions |
| US3551236A (en) * | 1968-07-10 | 1970-12-29 | Theodore H Fairbanks | Method and apparatus for the manufacture of net-like materials |
| US3567494A (en) * | 1968-08-29 | 1971-03-02 | Continental Can Co | Process for preparing polymerized surface coatings using ultra-violet radiation |
| CH528957A (de) * | 1969-06-04 | 1972-10-15 | Lonza Ag | Verfahren zur Herstellung von cellulosehaltigem Material mit verbesserter Abriebfestigkeit |
| US3661614A (en) * | 1969-12-11 | 1972-05-09 | Sun Chemical Corp | Radiation-curable ink compositions |
| US4045416A (en) * | 1971-01-21 | 1977-08-30 | Union Carbide Corporation | Amine acrylate addition reaction product compositions |
| DE2232365C2 (de) * | 1972-07-01 | 1982-06-09 | Basf Ag, 6700 Ludwigshafen | Durch UV-Bestrahlung polymerisierbare Gemische |
| US3874906A (en) * | 1972-09-22 | 1975-04-01 | Ppg Industries Inc | Process for applying polyester-acrylate containing ionizing irradiation curable coatings |
| US3914594A (en) * | 1973-03-19 | 1975-10-21 | Sun Chemical Corp | Radiation lamp reflector assembly |
| US3826014A (en) * | 1973-03-19 | 1974-07-30 | Sun Chemical Corp | Shutter mechanism for radiation-curing lamp |
| JPS5419895B2 (en, 2012) * | 1973-07-27 | 1979-07-18 | ||
| US3903322A (en) * | 1974-03-07 | 1975-09-02 | Continental Can Co | Photopolymerizable ethylenically unsaturated compounds photoinitiated with benzoyl derivatives of diphenyl sulfide and an organic amine compound |
| GB1481131A (en) * | 1974-03-22 | 1977-07-27 | Nat Starch Chem Corp | Actinic radiation curable materials |
| US4005244A (en) * | 1974-09-30 | 1977-01-25 | Ppg Industries, Inc. | Ultraviolet light curable opacifying compositions |
| US4042749A (en) * | 1974-10-08 | 1977-08-16 | Minnesota Mining And Manufacturing Company | Article having abrasion resistant surface formed from the reaction product of a silane and a metal ester |
| US4084021A (en) * | 1974-10-08 | 1978-04-11 | Minnesota Mining And Manufacturing Company | Method for rendering substrates resistant to abrasion |
| US4016334A (en) * | 1975-02-18 | 1977-04-05 | Celanese Corporation | Method of applying high adhesion ultraviolet curable coatings and coated articles |
| US3992276A (en) * | 1975-03-17 | 1976-11-16 | Celanese Corporation | Unsaturated polyesters for ultraviolet curable coatings |
| US4037112A (en) * | 1975-03-25 | 1977-07-19 | Ppg Industries, Inc. | Apparatus for crosslinking ultraviolet light curable coatings |
| US4086373A (en) * | 1975-04-02 | 1978-04-25 | Owens-Illinois, Inc. | Protective polymeric coating for glass substrate |
| US4113893A (en) * | 1975-07-01 | 1978-09-12 | Ppg Industries, Inc. | Radiation cure of coating compositions containing diacrylate monomer and hiding pigment |
| US3988228A (en) * | 1975-08-29 | 1976-10-26 | Eastman Kodak Company | Photopolymerizable polymeric compositions containing halogen containing aromatic ketones |
| GB1553580A (en) * | 1975-11-21 | 1979-09-26 | Espe Pharm Praep | Photopolymerisable acrylic or methacrylic acid ester-containing compositions |
| US4091050A (en) * | 1976-01-27 | 1978-05-23 | Ppg Industries, Inc. | Method for the preparation of mixtures of (meth)acrylic terminated polyether resin and 3-halo-2-hydroxypropyl (meth)acrylate |
| US4024297A (en) * | 1976-02-02 | 1977-05-17 | Ppg Industries, Inc. | Actinic light polymerizable coating compositions |
| US4012302A (en) * | 1976-02-17 | 1977-03-15 | Eastman Kodak Company | Photocurable compositions containing s-aryl arylcarbothioic acid esters as photoinitiators |
| US4065368A (en) * | 1976-02-23 | 1977-12-27 | Bell Telephone Laboratories, Incorporated | Printed circuit cover coating comprising an ultraviolet radiation sensitive acrylic resin |
| JPS591401B2 (ja) * | 1976-04-26 | 1984-01-12 | 東洋インキ製造株式会社 | 紫外線硬化性組成物 |
| US4099837A (en) * | 1976-05-26 | 1978-07-11 | Bell Telephone Laboratories, Incorporated | Coating of fiber lightguides with UV cured polymerization products |
| US4147603A (en) * | 1976-07-27 | 1979-04-03 | Eastman Kodak Company | Radiation curable cellulose compositions |
| US4066582A (en) * | 1976-09-27 | 1978-01-03 | Union Carbide Corporation | Improved acrylate based radiation curable coating compositions containing nitrocellulose |
| US4134809A (en) * | 1977-08-22 | 1979-01-16 | Eastman Kodak Company | Radiation curable cellulose ester-acrylate compositions |
| US4194955A (en) * | 1978-11-13 | 1980-03-25 | Celanese Corporation | Ultraviolet curable self-pigmented coating composition |
| US4308119A (en) * | 1979-02-21 | 1981-12-29 | Panelgraphic Corporation | Abrasion-resistant optical coating composition containing pentaerythritol based polyacrylates and cellulose esters |
-
1980
- 1980-01-07 US US06/104,351 patent/US4308119A/en not_active Expired - Lifetime
- 1980-02-12 CA CA000345431A patent/CA1153491A/en not_active Expired
- 1980-02-20 JP JP55500574A patent/JPH021162B2/ja not_active Expired
- 1980-02-20 GB GB8033385A patent/GB2056886B/en not_active Expired
- 1980-02-20 FR FR8003720A patent/FR2449715B1/fr not_active Expired
- 1980-02-20 WO PCT/US1980/000162 patent/WO1980001805A1/en active Application Filing
-
1988
- 1988-04-13 JP JP63091208A patent/JPS6426647A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH021162B2 (en, 2012) | 1990-01-10 |
| GB2056886B (en) | 1983-08-24 |
| JPS56500258A (en, 2012) | 1981-03-05 |
| US4308119A (en) | 1981-12-29 |
| FR2449715A1 (en, 2012) | 1980-09-19 |
| WO1980001805A1 (en) | 1980-09-04 |
| JPH0341495B2 (en, 2012) | 1991-06-24 |
| GB2056886A (en) | 1981-03-25 |
| JPS6426647A (en) | 1989-01-27 |
| FR2449715B1 (en, 2012) | 1984-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |