EP3126427A1 - Branched polyester polymers and soft touch coatings comprising the same - Google Patents
Branched polyester polymers and soft touch coatings comprising the sameInfo
- Publication number
- EP3126427A1 EP3126427A1 EP15716685.1A EP15716685A EP3126427A1 EP 3126427 A1 EP3126427 A1 EP 3126427A1 EP 15716685 A EP15716685 A EP 15716685A EP 3126427 A1 EP3126427 A1 EP 3126427A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- polyester
- coating
- acid
- prepolymer
- anhydride
- 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.)
- Withdrawn
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 150
- 229920000728 polyester Polymers 0.000 title claims abstract description 141
- 229920000642 polymer Polymers 0.000 title claims description 31
- 239000000758 substrate Substances 0.000 claims abstract description 43
- 229920006305 unsaturated polyester Polymers 0.000 claims abstract description 24
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 14
- 239000011248 coating agent Substances 0.000 claims description 87
- 229920005862 polyol Polymers 0.000 claims description 45
- 150000003077 polyols Chemical class 0.000 claims description 45
- 150000002148 esters Chemical class 0.000 claims description 38
- 229910052751 metal Inorganic materials 0.000 claims description 30
- 239000002184 metal Substances 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 27
- 239000004971 Cross linker Substances 0.000 claims description 22
- 239000003086 colorant Substances 0.000 claims description 22
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 16
- 125000004018 acid anhydride group Chemical group 0.000 claims description 15
- 150000008064 anhydrides Chemical class 0.000 claims description 14
- 238000005299 abrasion Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 10
- 239000001361 adipic acid Substances 0.000 claims description 8
- 235000011037 adipic acid Nutrition 0.000 claims description 8
- 230000003746 surface roughness Effects 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- 229920007019 PC/ABS Polymers 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 238000006116 polymerization reaction Methods 0.000 abstract description 11
- 239000000203 mixture Substances 0.000 description 61
- 229920005989 resin Polymers 0.000 description 35
- 239000011347 resin Substances 0.000 description 35
- 239000000178 monomer Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 26
- 239000003999 initiator Substances 0.000 description 24
- -1 alkylene glycols Chemical class 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000002245 particle Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 239000002105 nanoparticle Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000008199 coating composition Substances 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 11
- 235000013305 food Nutrition 0.000 description 11
- 239000000049 pigment Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- 229920000515 polycarbonate Polymers 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 238000004806 packaging method and process Methods 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 229920003180 amino resin Polymers 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- 229920001225 polyester resin Polymers 0.000 description 6
- 239000004645 polyester resin Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- ZAXXZBQODQDCOW-UHFFFAOYSA-N 1-methoxypropyl acetate Chemical compound CCC(OC)OC(C)=O ZAXXZBQODQDCOW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 235000008960 ketchup Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 235000019271 petrolatum Nutrition 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000000475 sunscreen effect Effects 0.000 description 3
- 239000000516 sunscreening agent Substances 0.000 description 3
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- 229920001342 Bakelite® Polymers 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010073306 Exposure to radiation Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 239000004637 bakelite Substances 0.000 description 2
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
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- 229920001577 copolymer Polymers 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000000937 dynamic scanning calorimetry Methods 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
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- 239000004611 light stabiliser Substances 0.000 description 2
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- 238000005259 measurement Methods 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 2
- 239000011146 organic particle Substances 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000012748 slip agent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
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- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 1
- 239000010434 nepheline Substances 0.000 description 1
- 229910052664 nepheline Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 235000021586 packaging of beverage Nutrition 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 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
- 239000002356 single layer Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000010435 syenite Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 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
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 125000005627 triarylcarbonium group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
- B32B27/365—Layered products comprising a layer of synthetic resin comprising polyesters comprising polycarbonates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/02—Physical, chemical or physicochemical properties
- B32B7/025—Electric or magnetic properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/02—Physical, chemical or physicochemical properties
- B32B7/027—Thermal properties
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0407—Processes of polymerisation
- C08F299/0421—Polymerisation initiated by wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/044—Forming conductive coatings; Forming coatings having anti-static properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/052—Forming heat-sealable coatings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
- C09D167/07—Unsaturated polyesters having carbon-to-carbon unsaturation having terminal carbon-to-carbon unsaturated bonds
Definitions
- the present invention relates to crosslinkable branched polyester polymers prepared by free radical polymerization of the double bonds of a first unsaturated polyester prepolymer and a second unsaturated polyester prepolymer.
- the polyester polymers have a Tg of 25°C or less.
- the present invention further relates to coatings comprising such polyesters and substrates to which such coatings are applied; the coating, when cured, imparts a soft touch to the substrate.
- Particularly suitable examples include substrates used in the packaging industry, coil coatings, and certain industrial and automotive coatings. It is often desired that coatings have a particular "touch feel"; in the consumer electronics industry, for example, it is often desired to have a coating with a "soft feel” or “soft touch”.
- a soft touch coating can impart a range of touch feel, for example, a velvety feel, a silky feel, or a rubbery feel, to a substrate. Notwithstanding the feel of the coating, it would also be desired that the coating have at least some degree of resistance to abrasion, marring, scratching and/or staining. Soft touch coatings having acceptable performance properties are therefore desired.
- the present invention is directed to a crosslinkable branched polyester polymer prepared by free radical polymerization of a double bond of a first unsaturated polyester prepolymer and a double bond of a second unsaturated polyester prepolymer, wherein each prepolymer independently comprises: a) a polyol segment; and b) an unsaturated polycarboxylic acid and/or an anhydride and/or ester thereof; wherein the branched polyester polymer has a Tg of 25°C or less. Coatings comprising such polyesters are also within the scope of the present invention, as are substrates coated at least in part with such coatings.
- the present invention is directed to crosslinkable branched polyester polymers generally comprising a reaction product of prepolymers, which prepolymers are the reaction product of components comprising a polyol segment and an unsaturated polycarboxylic acid and/or an anhydride and/or ester thereof.
- the prepolymers are unsaturated polyesters, and are sometimes referred to herein as an "unsaturated polyester prepolymer", "prepolymer” or like terms.
- Free radical initiators are used to initiate polymerization through the unsaturation of the unsaturated polyester prepolymers, thereby resulting in a branched polyester.
- the branched polyester is crosslinkable, which means that it can undergo crosslinking with another compound. That is, the polyester has functionality that will react with functionality on another compound, such as a crosslinker. Reaction of the
- unsaturation of the prepolymers results in the crosslinkable branched polyester.
- This polyester is a polymer. It is not a cured coating.
- the present invention is therefore distinct from art in which crosslinking the points of unsaturation on monomers and/or polymers results in a cured coating.
- the unsaturated polyester prepolymer comprises a polyol segment.
- Polyol and like terms, as used herein, refers to a compound having two or more hydroxyl groups.
- the polyol used to form the polyol segment is sometimes referred to herein as the "polyol segment monomer”.
- Polyols can be chosen to contribute softness to the prepolymer. Polyols can also contribute hardness, however, so the polyol(s) used and amount of each should be selected so that the unsaturated prepolymers, when reacted, result in a branched polyester having a Tg of 25°C or less.
- Suitable polyols for use in the invention may be any polyol or mixtures thereof known for making polyesters.
- alkylene glycols such as ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and neopentyl glycol; hydrogenated bisphenol A; cyclohexanediol; propanediols including 1 ,2-propanediol, 1,3-propanediol, butyl ethyl propanediol, 2-methyl-l,3-propanediol, and 2-ethyl-2-butyl- 1,3 -propanediol; butanediols including 1,4-butanediol, 1,3- butanediol, and 2-ethyl- 1,4-butanediol; pentanediols including trimethyl pentanediol and 2-
- Suitable unsaturated polyols for use in the invention may be any unsaturated alcohols containing two or more hydroxyl groups. Examples include, but are not limited to, trimethylol propane monoallyl ether, trimethylol ethane monoallyl ether and prop-l-ene-l,3-diol.
- the polyol segment can also comprise some mono-ol, such as up to 10 weight %, or 5 weight %, based on the total weight of the polyol segment. In certain embodiments, the polyol segment comprises 10 to 90 weight % of the polyester prepolymer, such as 30 to 50 weight %. The percent of polyol in the prepolymer can vary widely depending on the molecular weight of the polyol segment.
- the unsaturated polyester prepolymer further comprises an unsaturated polycarboxylic acid/anhydride/ester.
- Suitable unsaturated polyacids for use in the invention may be any unsaturated carboxylic acid containing two or more carboxy groups and/or an ester and/or anhydride thereof, or mixtures thereof. Examples include, but are not limited to, maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid and teraconic acid, and/or esters and/or anhydrides thereof.
- the unsaturated polyacid is in the form of an ester
- these esters may be formed with any suitable alcohol, such as CI -CI 8 alkyl esters formed by reaction of a CI - C18 alcohol (e.g. methanol, ethanol, 1-propanol, 1-butanol, 2-butanol, isobutanol, 1- pentanol, 1-pentanol and 1-hexonol) with the polyacid.
- a particularly suitable unsaturated polyacid is maleic acid, maleic anhydride or a C1-C6 alkyl ester of maleic acid.
- the unsaturated polycarboxylic acid/anhydride/ester comprises 3 to 25 weight % of the polyester prepolymer, such as 5 to 20 weight %.
- the polyester prepolymer can further comprise one or more monomers that contribute to the overall properties of the polyester, including "softness".
- one or more monomers that contribute a "soft segment” can be used with the one or more polyols and one or more unsaturated polycarboxylic
- soft segment and like terms refers to a monomer or residue thereof or mixtures thereof that contribute flexibility to the prepolymer, and can help to obtain the desired Tg and/or viscosity of the branched polyester.
- the soft segment can be the residue of, for example, a polyacid.
- Polyacid and like terms, as used herein, refers to a compound having two or more acid groups and includes the ester and/or anhydride of the acid.
- Such acids can include, for example, linear acids that impart flexibility. Examples include but are not limited to saturated polyacids such as adipic acid, azelaic acid, sebacic acid, succinic acid, glutaric acid, decanoic diacid, dodecanoic diacid and esters and anhydrides thereof.
- Suitable monoacids include Ci-Cis aliphatic carboxylic acids such as acetic acid, propanoic acid, butanoic acid, hexanoic acid, oleic acid, linoleic acid, undecanoic acid, lauric acid, isononanoic acid, other fatty acids, and hydrogenated fatty acids of naturally occurring oils; and/or esters and/or anhydrides of any of these.
- one or more additional acids can also be used.
- the additional acid can be an aromatic acid or a cycloaliphatic acid, suitable examples of which include, but are not limited to, phthalic acid, isophthalic acid, 5- tert-butylisophthalic acid, tetrachlorophthalic acid, benzoic acid, t-butylbenzoic acid, tetrahydrophthalic acid, naphthalene polycarboxylic acid, terephthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, dimethyl terephthalate, cyclohexane dicarboxylic acid, chlorendic anhydride, 1 ,3-cyclohexane dicarboxylic acid, 1 ,4-cyclohexane dicarboxylic acid, tricyclodecane polycarboxylic acid, endomethylene tetrahydrophthalic acid, endoethylene hexa
- the additional acids listed above may impart rigidity to the branched polyester and therefore cause the Tg of the branched polyester to increase.
- the acids used and amounts of each acid should be selected so that, when the prepolymers are reacted, the branched polyester has a Tg of 25°C or less.
- Other monomer components can also be used in formation of the prepolymer to impart one or more additional properties to the branched polyester and/or coating comprising the same.
- phthalic anhydride can be included, such as in amounts of 2 to 20 weight % of the prepolymer; phthalic anhydride might impart greater stain resistance to the coating.
- copolymerization of the unsaturated prepolymer with PDMS silmer acrylate could impart flexibility and/or improve fingerprint resistance in the final coating.
- silmer acrylate monomer can be used in any suitable amount, such as 0.1 to 10 wt %.
- Fatty diacids could be added to increase hydrophobicity, while a polyether such as poly THF could be used to make the branched polyester more hydrophilic.
- the unsaturated polyester prepolymer can be prepared by any means known in the art.
- a soft segment and polyol segment are prereacted to form what is sometimes referred to herein as a "polyol prepolymer", and then further reacted with the unsaturated polycarboxylic acid/anhydride/ester.
- the polyol segment and unsaturated polycarboxylic acid/anhydride/ester are reacted together either with or without the soft segment.
- the polyol is typically in excess as compared to the soft segment when a soft segment is included.
- the ratio of reactive groups on the soft segment monomer to reactive groups on the polyol segment monomer may be 1 :2, 2:3 or even higher.
- crosslinkable, branched polyester is 25°C or less.
- the Tg of the prepolymers reacted to form the branched polyester is also 25°C or less.
- the Tg of one or more prepolymers may be greater than 25 °C while the Tg of one or more prepolymers may be 25°C or less, such that, when reacted, the resulting branched polyester has a Tg of 25°C or less.
- any free radical initiator typically used to initiate the polymerization of unsaturated compounds containing double bonds may be used in the free radical polymerization.
- the free radical initiator can be an azo initiator or a peroxide initiator, such as tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxybenzoate or dibenzoyl peroxide.
- the ratio of initiator to unsaturated acid/anhydride/ester may be varied depending upon the degree of branching of the chains of the polyester that is desired.
- the molar ratio of the initiator to the double bonds may be 0.001 to 1.0, such as 0.01 to 0.9 or 0.5 to 1.
- a higher amount of initiator is used, the more branching will be achieved. Increased branching typically means higher functionality in the polyester. In certain embodiments, a lower amount of initiator may be used, such as 0.1, so as to minimize the amount of branching and retain some unsaturation in the polyester. Such embodiment might provide particularly desirable flexibility in the final coating.
- the present branched polyesters have a degree of branching or Mark-Howink parameter of less that 0.58, such as 0.50 or less or 0.48 or less as measured by triple detector GPC.
- the initiator can be added in different portions at different times. For example, all of the free radical initiator may be added at the start of the reaction, the initiator may be divided into portions and the portions added at intervals during the reaction, or the initiator may be added as a continuous feed. It will be appreciated that the addition of initiator at set intervals or in a continuous feed will result in a more controlled process than adding all of the initiator at the start. In certain embodiments, the initiator is added over 10 minutes, until the molecular weight of the polyester doubles or triples.
- the free radical polymerization can be conducted under various conditions allowing for parameters such as the molecular weight of the branched polyester, the degree of functionality, the amount of branching and the like to be controlled so as to obtain the branched polyester that gives the desired feel and properties to the final coating.
- polyester prepolymer is made, whether a polyol prepolymer is formed first or a soft segment monomer, if used, and polyol segment monomer are reacted directly with the polycarboxylic
- the resulting branched polyester will actually be a mixture of polyesters with varying degrees of unsaturation, chain length, branching and the like. Some of the resulting product may even be a monoester, but is still encompassed by the term "polyester" as used herein.
- the temperature at which the free radical polymerization reaction is conducted may be varied depending on factors such as the composition of the unsaturated acid/anhydride/ester, the polyol segment monomer, the soft segment monomer, if used, the initiator, the solvent and the properties that are desired in the polyester.
- the free radical polymerization is conducted at a temperature of from 50°C to 150°C.
- the higher temperature results in a higher concentration of free radical initiator, which in turn results in more chains being polymerized, each with a relatively low molecular weight.
- the polyester of the present invention is ungelled.
- the free radical polymerization can be performed using solutions of the unsaturated acid/anhydride/ester and polyol prepolymer (or soft segment monomer and polyol segment monomer).
- Any solvent may be used, as long as it is able to dissolve the components including the free radical initiator to a sufficient degree to allow the polymerization to take place efficiently.
- suitable solvents include butyl glycol, propylene glycol mono methyl ether, methoxy propyl acetate and xylene.
- Preparation of the polyester in solvent is sometimes referred to herein as a "solvent-based system", which means that greater than 50%, such as up to 100%), of the solvent is an organic solvent, and less than 50%> of the solvent, such as less than 20%>, less than 10%>, less than 5%, or less than 2% of the solvent is water.
- the polyester can be prepared in a water-based system.
- a "water-based system” is one in which greater than 50%>, such as up to 100%, of the solvent is water, and less than 50%> of the solvent, such as less than 20%>, less than 10%, less than 5%, or less than 2% of the solvent is an organic solvent.
- the polymerization is done without solvent; that is, all steps from making the prepolymer to making the polyester, can be done in the absence of solvent.
- the resulting polyester can be a liquid, such as a viscous liquid.
- the branched polyesters of the present invention are formed by free radical polymerization via the double bonds of a first and second unsaturated polyester prepolymer.
- the first and second prepolymers can be the same or different.
- two or more different unsaturated polyester prepolymers can be reacted together.
- "Different" in this context means that one or more components used in the unsaturated polyester prepolymers and/or the amount of one or more components used in the unsaturated polyester prepolymers can be different.
- polyester according to the present invention can be prepared using polyol prepolymers comprised of the same components, while in other embodiments they can be prepared by using two or more polyol prepolymers that are formed by different components.
- a first polyol prepolymer comprising a terminal hydroxyl group and a second polyol prepolymer comprising a terminal hydroxyl group are reacted with an unsaturated acid/anhydride/ester; the components used to make the first and second prepolymers can be different, and/or can have one or more different components and/or can have one or more different amounts if the same components are used.
- the resulting polyester is likely to have random units derived from each type of prepolymer used.
- the present invention encompasses polyesters prepared by prepolymers having the same or different polyol segments monomers, and/or unsaturated acids/anhydrides/esters and/or the same or different amounts of any of these; moreover, each of the prepolymers can have the same or different soft monomers and/or additional acid monomers and/or the same or different amounts of any of these.
- polyesters prepared by prepolymers having the same or different polyol segments monomers, and/or unsaturated acids/anhydrides/esters and/or the same or different amounts of any of these; moreover, each of the prepolymers can have the same or different soft monomers and/or additional acid monomers and/or the same or different amounts of any of these.
- polyesters having different properties.
- polyesters can be formed that have a Tg of 25°C or less and possibly other desirable properties deriving from the use of the particular components used in the prepolymers.
- prepolymers used according to the present invention comprise adipic acid (soft segment) such as in an amount of 10 to 60 weight %, 2-methyl-l,3-propanediol (polyol segment) such as in an amount of 0 to 50 weight %, and maleic anhydride, such as in an amount of up to 25 weight %, such as 5 to 20 weight %, with weight % based on total monomer weight in the
- Additional monomer can also be used, such as isophthalic acid or terephthalic acid, phthalic acid, succinic acid, and neopentyl glycol.
- the branched polyester is formed by using free radical polymerization, wherein the unsaturation of the polycarboxylic acid/anhydride/ester moieties in the prepolymers polymerize.
- the reaction is run such that substantially all of the unsaturation is reacted in the formation of the branched polyester, while in other embodiments the resulting polyester also comprises some degree of unsaturation.
- the resulting polyester can comprise enough unsaturation to render the polyester reactive with other functional groups through the points of unsaturation.
- the branched polyester according to the present invention is formed primarily through the free radical polymerization of the unsaturation in the prepolymers, the terminal hydroxyl groups will remain unreacted in the branched polyester of the present invention. These unreacted hydroxyl groups can then be crosslinked with another component.
- the present invention is distinct from art in which gelled polyesters, that is extensively networked polyesters, are formed.
- the present polyesters are thermoset, and therefore also distinct from art that teaches thermoplastic polyesters.
- hydroxyl functionality on the unsaturated polyester prepolymer before polymerization takes place, and/or on the branched polyester to another functionality.
- the hydroxyl can be reacted with a cyclic anhydride to result in acid functionality.
- Acid esters can also be formed.
- the unsaturated polyester prepolymer may comprise linkages in addition to the ester linkages.
- the polyester prepolymer may further comprise one or more urethane linkages.
- Urethane linkages could be introduced by reacting an excess of the polyol prepolymer or the unsaturated polyester polymer with a polyisocyanate. The resulting unsaturated polyester prepolymer will still have terminal functionality and unsaturation, but will have urethane linkages in addition to ester linkages. Other chemistries could also be introduced.
- the unsaturated polyester prepolymer comprises one ore more linkages in addition to ester linkages.
- the use of unsaturated monomers other than the unsaturated polyacid/anhydride/ester of the prepolymer product is excluded.
- the use of vinyl monomers such as (meth)acrylates, styrene, vinyl halides and the like can be excluded in certain embodiments.
- PDMS silmer acrylate can still be used if the double bond of the acrylate moiety is reacted in the formation of the prepolymer.
- any other acrylate or methacrylate containing monomer or polymer can be used if the double bond of the acrylate moiety is reacted in the formation of the prepolymer.
- the acrylate double bond is reacted and therefore unavailable to react with the unsaturation of a second prepolymer during free radical polymerization.
- the present branched polyesters are not polyester/acrylic graft copolymers, which are widely known in the art and are not formed by reaction of unsaturation on first and second polyester prepolymers.
- the present polyesters specifically exclude polyesters prepared from prepolymers that are formed by the reaction with aldehydes; thus, in this embodiment, acyl succinic acid polyesters are specifically excluded. Similarly, use of aldehyde in the solvent is specifically excluded in certain embodiments
- the branched polyesters of the present invention can have a relatively high molecular weight and functionality as compared to conventional linear polyester resins.
- the ratio of the weight average molecular weight ("Mw") of the branched polyester of the present invention to the Mw of the unsaturated polyester prepolymer is from 1.2 to 100, such as 4 or 5 to 50, although in certain embodiments, it can be as higher.
- the polyester prepolymers can have an Mw of 1,000 to 50,000, such as 5,000 to 10,000 or 7,000 to 8,000.
- the final branched polyester can have an Mw in the range of 2,000 to 100,000, such as 4,000-10,000.
- the prepolymer Mw can be related to the properties of the branched polyester as well as a coating comprising the polyester.
- a branched polyester with an Mw at the lower end of the range such as less than 10,000, might give a higher crosslink density or hardness in the coating as there would be higher functionality, and might have better flow and lower viscosity, while a branched polyester with an Mw higher than 10,000 might provide a coating with a lower crosslink density or hardness, but with a different touch feel.
- the equivalent weight of the polyester is 1000 or less. Equivalent weight is the Mw divided by the average functionality. Equivalent weight contributes to the crosslink density, which, as noted above, may affect the properties of soft touch coatings. For example, a higher equivalent weight may give a lower crosslink density.
- the branched polyesters of the present invention can also have a relatively high functionality; in some cases the functionality is higher than would be expected for conventional polyesters having such molecular weights.
- the average functionality of the polyester can be 2.0 or greater, such as 2.5 or greater, 3.0 or greater, or even higher.
- Average functionality refers to the average number of functional groups on the branched polyester. The functionality of the branched polyester is measured by the number of hydroxyl groups that remain unreacted in the branched polyester, and not by the unreacted unsaturation.
- the hydroxyl value of the branched polyesters of the present invention can be from 10 to 500 mg KOH/gm, such as 30 to 250 mg KOH/gm.
- the present branched polyesters will have both high Mw and high functionality, such as a Mw of > 15,000, such as 20,000 to 40,000, or higher than 40,000, and a functionality of > 100 mg KOH/gm.
- the polyester of the present invention comprises functionality, it is suitable for use in coating formulations in which the hydroxyl groups (and/or other functionality) are crosslinked with other resins and/or crosslinkers typically used in coating formulations.
- the present invention is further directed to a coating comprising a branched polyester according to the present invention and a crosslinker therefor.
- the crosslinker, or crosslinking resin or agent can be any suitable crosslinker or crosslinking resin known in the art, and will be chosen to be reactive with the functional group or groups on the polyester.
- the coatings of the present invention cure through the reaction of the hydroxyl groups and/or other functionality and the crosslinker and not through the double bonds of the polycarboxylic acid/anhydride/ester moiety, to the extent any such unsaturation exists in the branched polyester.
- Non-limiting examples of suitable crosslinkers include phenolic resins, amino resins, epoxy resins, isocyanate resins, beta-hydroxy (alkyl) amide resins, alkylated carbamate resins, polyacids, anhydrides, organometallic acid-functional materials, polyamines, polyamides, aminoplasts and mixtures thereof.
- the crosslinker is a phenolic resin comprising an alkylated
- Such crosslinkers are commercially available from Hexion as BAKELITE 6520LB and BAKELITE 7081LB.
- Suitable isocyanates include multifunctional isocyanates.
- multifunctional polyisocyanates include aliphatic diisocyanates like hexamethylene diisocyanate and isophorone diisocyanate, and aromatic diisocyanates like toluene diisocyanate and 4,4'-diphenylmethane diisocyanate.
- the polyisocyanates can be blocked or unblocked.
- suitable polyisocyanates include isocyanurate trimers, allophanates, and uretdiones of diisocyanates and polycarbodiimides such as those disclosed in United States Patent 8,389,113, incorporated by reference in pertinent part herein.
- Suitable polyisocyanates are well known in the art and widely available commercially. For example, suitable polyisocyanates are disclosed in United States Patent Number 6,316,119 at columns 6, lines 19-36, incorporated by reference herein. Examples of commercially available polyisocyanates include DESMODUR VP2078 and DESMODUR N3390, which are sold by Bayer Corporation, and TOLONATE HDT90, which is sold by Rhodia Inc.
- Suitable aminoplasts include condensates of amines and/or amides with aldehyde.
- the condensate of melamine with formaldehyde is a suitable aminoplast.
- suitable aminoplasts are well known in the art.
- a suitable aminoplast is disclosed, for example, in United States Patent Number 6,316,119 at column 5, lines 45-55, incorporated by reference herein.
- the branched polyester and the crosslinker can be dissolved or dispersed in a single solvent or a mixture of solvents.
- Any solvent that will enable the formulation to be coated on a substrate may be used, and these will be well known to the person skilled in the art.
- Typical examples include water, organic solvent(s), and/or mixtures thereof.
- Suitable organic solvents include glycols, glycol ether alcohols, alcohols, ketones, and aromatics, such as xylene and toluene, acetates, mineral spirits, naphthas and/or mixtures thereof.
- “Acetates” include the glycol ether acetates.
- the solvent is a non-aqueous solvent.
- Non-aqueous solvent and like terms means that less than 50% of the solvent is water.
- less than 10%, or even less than 5% or 2%, of the solvent can be water.
- mixtures of solvents, including or excluding water in an amount of less than 50% can constitute a "non-aqueous solvent”.
- the coating is aqueous or water-based. This means that 50% or more of the solvent is water.
- These embodiments have less than 50%>, such as less than 20%>, less than 10%>, less than 5% or less than 2% solvent.
- the coatings of the present invention further comprise a curing catalyst.
- a curing catalyst typically used to catalyze crosslinking reactions between polyester resins and crosslinkers, such as phenolic resins, may be used, and there are no particular limitations on the catalyst.
- Examples of such a curing catalyst include dibutyltin dilaurate, phosphoric acid, alkyl aryl sulphonic acid, dodecyl benzene sulphonic acid, dinonyl naphthalene sulphonic acid, and dinonyl naphthalene disulphonic acid.
- the desired "touch” to the final coating should be balanced to give the desired "touch" to the final coating.
- monomer selection and content may play a role, as might Mw, equivalent weight, and degree of branching.
- the Tg of the branches can be decreased so as to increase the "soft touch” quality of the coating.
- the selection of crosslinker can also contribute to the soft touch.
- the crosslinker and amount of crosslinker used can be selected to give the desired crosslink density, which, as noted above, relates to touch feel.
- the gloss of the coating at 60° is 0.5- 1.5.
- the coating compositions can comprise other optional materials well known in the art of formulating coatings, such as colorants, plasticizers, abrasion resistant particles, anti-oxidants, hindered amine light stabilizers, UV light absorbers and stabilizers, surfactants, flow control agents, thixotropic agents, fillers, organic cosolvents, reactive diluents, catalysts, grind vehicles, slip agents and other customary auxiliaries.
- colorants such as colorants, plasticizers, abrasion resistant particles, anti-oxidants, hindered amine light stabilizers, UV light absorbers and stabilizers, surfactants, flow control agents, thixotropic agents, fillers, organic cosolvents, reactive diluents, catalysts, grind vehicles, slip agents and other customary auxiliaries.
- colorant means any substance that imparts color and/or other opacity and/or other visual effect, e.g. gloss, to the composition.
- the colorant can be added to the coating in any suitable form, such as discrete particles, dispersions, solutions and/or flakes.
- a single colorant or a mixture of two or more colorants can be used in the coatings of the present invention.
- Example colorants include matting pigments, dyes and tints, such as those used in the paint industry and/or listed in the Dry Color Manufacturers Association (DCMA), as well as special effect compositions.
- a colorant may include, for example, a finely divided solid powder that is insoluble but wettable under the conditions of use.
- a colorant can be organic or inorganic and can be agglomerated or non-agglomerated.
- Colorants can be incorporated into the coatings by grinding or simple mixing. Colorants can be incorporated by grinding into the coating by use of a grind vehicle, such as an acrylic grind vehicle, the use of which will be familiar to one skilled in the art.
- Example pigments and/or pigment compositions include, but are not limited to, carbazole dioxazine crude pigment, azo, monoazo, disazo, naphthol AS, salt type (lakes), benzimidazolone, condensation, metal complex, isoindolinone, isoindoline and polycyclic phthalocyanine, quinacridone, perylene, perinone, diketopyrrolo pyrrole, thioindigo, anthraquinone, indanthrone, anthrapyrimidine, flavanthrone, pyranthrone, anthanthrone, dioxazine, triarylcarbonium, quinophthalone pigments, diketo pyrrolo pyrrole red (“DPPBO red”), titanium dioxide, carbon black, carbon fiber, graphite, other conductive pigments and/or fillers and mixtures thereof.
- the terms "pigment” and "colored filler” can be used interchangeably.
- Example dyes include, but are not limited to, those that are solvent and/or aqueous based such as acid dyes, azoic dyes, basic dyes, direct dyes, disperse dyes, reactive dyes, solvent dyes, sulfur dyes, mordant dyes, for example, bismuth vanadate, anthraquinone, perylene aluminum, quinacridone, thiazole, thiazine, azo, indigoid, nitro, nitroso, oxazine, phthalocyanine, quinoline, stilbene, and triphenyl methane.
- solvent and/or aqueous based such as acid dyes, azoic dyes, basic dyes, direct dyes, disperse dyes, reactive dyes, solvent dyes, sulfur dyes, mordant dyes, for example, bismuth vanadate, anthraquinone, perylene aluminum, quinacridone, thiazole, thiazine, azo, indigo
- Example tints include, but are not limited to, pigments dispersed in water- based or water-miscible carriers such as AQUA-CHEM 896 commercially available from Degussa, Inc., CHARISMA COLORANTS and MAXITONER INDUSTRIAL COLORANTS commercially available from Accurate Dispersions division of Eastman Chemicals, Inc.
- AQUA-CHEM 896 commercially available from Degussa, Inc.
- CHARISMA COLORANTS and MAXITONER INDUSTRIAL COLORANTS commercially available from Accurate Dispersions division of Eastman Chemicals, Inc.
- the colorant can be in the form of a dispersion including, but not limited to, a nanoparticle dispersion.
- Nanoparticle dispersions can include one or more highly dispersed nanoparticle colorants and/or colorant particles that produce a desired visible color and/or opacity and/or visual effect.
- Nanoparticle dispersions can include colorants such as pigments or dyes having a particle size of less than 150 nm, such as less than 70 nm, or less than 30 nm. Nanoparticles can be produced by milling stock organic or inorganic pigments with grinding media having a particle size of less than 0.5 mm.
- Example nanoparticle dispersions and methods for making them are identified in United States Patent Number 6,875,800 B2, which is incorporated herein by reference. Nanoparticle dispersions can also be produced by crystallization, precipitation, gas phase condensation, and chemical attrition (i.e., partial dissolution). In order to minimize re-agglomeration of nanoparticles within the coating, a dispersion of resin-coated nanoparticles can be used. As used herein, a "dispersion of resin-coated nanoparticles" refers to a continuous phase in which is dispersed discreet "composite microparticles" that comprise a nanoparticle and a resin coating on the nanoparticle. Example dispersions of resin-coated nanoparticles and methods for making them are described, for example, in United States Patent Number 7,605,194 at column 3, line 56 to column 16, line 25, the cited portion of which being incorporated herein by reference.
- Example special effect compositions that may be used include pigments and/or compositions that produce one or more appearance effects such as reflectance, pearlescence, metallic sheen, phosphorescence, fluorescence, photochromism, photosensitivity, thermochromism, goniochromism and/or color-change. Additional special effect compositions can provide other perceptible properties, such as opacity or texture. In a non-limiting embodiment, special effect compositions can produce a color shift, such that the color of the coating changes when the coating is viewed at different angles.
- Example color effect compositions are identified in United States Patent Number 6,894,086, incorporated herein by reference.
- Additional color effect compositions can include transparent coated mica and/or synthetic mica, coated silica, coated alumina, a transparent liquid crystal pigment, a liquid crystal coating, and/or any composition wherein interference results from a refractive index differential within the material and not because of the refractive index differential between the surface of the material and the air.
- a photosensitive composition and/or photochromic composition which reversibly alters its color when exposed to one or more light sources, can be used in the coating of the present invention.
- Photochromic and/or photosensitive compositions can be activated by exposure to radiation of a specified wavelength. When the composition becomes excited, the molecular structure is changed and the altered structure exhibits a new color that is different from the original color of the composition. When the exposure to radiation is removed, the photochromic and/or photosensitive composition can return to a state of rest, in which the original color of the composition returns.
- the photochromic and/or photosensitive composition can be colorless in a non-excited state and exhibit a color in an excited state. Full color-change can appear within milliseconds to several minutes, such as from 20 seconds to 60 seconds.
- Example photochromic and/or photosensitive compositions include photochromic dyes.
- the photosensitive composition and/or photochromic composition can be associated with and/or at least partially bound to, such as by covalent bonding, a polymer and/or polymeric materials of a
- the photosensitive composition and/or photochromic composition associated with and/or at least partially bound to a polymer and/or polymerizable component in accordance with a non-limiting embodiment of the present invention have minimal migration out of the coating.
- Example photosensitive compositions and/or photochromic compositions and methods for making them are identified in United States Patent 8,153,344, and incorporated herein by reference.
- the colorant can be present in any amount sufficient to impart the desired visual and/or color effect.
- the colorant may comprise from 1 to 65 weight percent of the present compositions, such as from 3 to 40 weight percent or 5 to 35 weight percent, with weight percent based on the total weight of the compositions.
- An "abrasion resistant particle” is one that, when used in a coating, will impart some level of abrasion resistance to the coating as compared with the same coating lacking the particles.
- Suitable abrasion resistant particles include organic and/or inorganic particles. Examples of suitable organic particles include but are not limited to diamond particles, such as diamond dust particles, and particles formed from carbide materials; examples of carbide particles include but are not limited to titanium carbide, silicon carbide and boron carbide.
- suitable inorganic particles include but are not limited to silica; alumina; alumina silicate; silica alumina; alkali aluminosilicate; borosilicate glass; nitrides including boron nitride and silicon nitride; oxides including titanium dioxide and zinc oxide; quartz; nepheline syenite; zircon such as in the form of zirconium oxide; buddeluyite; and eudialyte. Particles of any size can be used, as can mixtures of different particles and/or different sized particles.
- the particles can be microparticles, having an average particle size of 0.1 to 50, 0.1 to 20, 1 to 12, 1 to 10, or 3 to 6 microns, or any combination within any of these ranges.
- the particles can be nanoparticles, having an average particle size of less than 0.1 micron, such as 0.8 to 500, 10 to 100, or 100 to 500 nanometers, or any combination within these ranges.
- any slip agent can be used according to the present invention such as those commercial available from BYK Chemie or Dow Corning.
- the polyesters of the present invention are used as coating additives.
- the present polyesters can replace all or part of the sag control agent, such as cellulose esters, used in coating formulations comprising metallic flake.
- the branched polyester of the present invention and crosslinker therefor can form all or part of the film-forming resin of the coating.
- one or more additional film-forming resins are also used in the coating.
- the coating are also used in the coating.
- compositions can comprise any of a variety of thermoplastic and/or thermosetting compositions known in the art.
- the coating compositions may be water-based or solvent-based liquid compositions, or alternatively, may be in solid particulate form, i.e. a powder coating.
- Thermosetting or curable coating compositions typically comprise film-forming polymers or resins having functional groups that are reactive with either themselves or a crosslinking agent.
- the additional film-forming resin can be selected from, for example, acrylic polymers, polyester polymers, polyurethane polymers, polyamide polymers, polyether polymers, polysiloxane polymers, copolymers thereof, and mixtures thereof.
- these polymers can be any polymers of these types made by any method known to those skilled in the art.
- Such polymers may be solvent-borne or water-dispersible, emulsifiable, or of limited water solubility.
- the functional groups on the film-forming resin may be selected from any of a variety of reactive functional groups including, for example, carboxylic acid groups, amine groups, epoxide groups, hydroxyl groups, thiol groups, carbamate groups, amide groups, urea groups, isocyanate groups (including blocked isocyanate groups) mercaptan groups, and combinations thereof.
- Appropriate mixtures of film-forming resins may also be used in the preparation of the present coating compositions.
- Thermosetting coating compositions typically comprise a crosslinking agent that may be selected from any of the crosslinkers described above.
- the present coatings comprise a thermosetting film-forming polymer or resin and a crosslinking agent therefor and the crosslinker is either the same or different from the crosslinker that is used to crosslink the branched polyester.
- a thermosetting film-forming polymer or resin having functional groups that are reactive with themselves are used; in this manner, such thermosetting coatings are self-crosslinking.
- the coatings of the present invention may comprise 1 to 100, such as 10 to 90 or 20 to 80 weight %, with weight % based on total solid weight of the coating, of the branched polyester of the present invention.
- the coating compositions of the present invention may also comprise 0 to 90, such as 5 to 60 or 10 to 40 weight %, with weight % based on total solids weight of the coating, of a crosslinker for the branched polyester. Additional components, if used, may comprise 1 weight %, up to 70 weight %, or higher, with weight % based on total solids weight of the coating.
- Coating formulations according to the present invention can have a soft touch and/or smooth feel when cured on a substrate.
- the coating can have a softness as measured by the Fischer Micro-hardness test of 1 to 20 N/mm 2 , such as 2 to 10 N/mm 2 .
- the coating can further have a coefficient of friction as measured by ASTM Method D1894 of 0.01 to 0.5, such as 0.05 to 0.2.
- “Coefficient of friction” refers to the ratio of the force that maintains contact between an object and a surface and the frictional force that resists the motion of the object.
- the coating, at 50 micron thickness can have an abrasion resistance as measured by ASTM Method F2357 of 50 to 500 cycles, such as 250 to 500.
- the cured coating can also have a surface roughness of 1 ⁇ to 80 ⁇ , such as 10 ⁇ to 60 ⁇ , 20 ⁇ to 50 ⁇ , or 35 ⁇ to 45 ⁇ as measured by a Taylor Hobson Precision Duo Profilometer.
- Surface roughness can be altered through formulation, such as through the use of additives, an example of which is silica. It will be appreciated by those skilled in the art that achieving this level of hardness, coefficient of friction, abrasion resistance, and surface roughness in the same coating is a remarkable accomplishment. The result is a coating that is soft to the touch, but durable. While the inventors believe this combination of properties is achieved due to the branching of the polyester, they do not wish to be bound by any mechanism.
- the prepolymers, the branched polyester and/or the coatings of the present invention may be substantially free, may be essentially free and/or may be completely free of bisphenol A and derivatives or residues thereof, including bisphenol A (“BP A”) and bisphenol A diglycidyl ether (“BADGE”).
- BP A bisphenol A
- BADGE bisphenol A diglycidyl ether
- Such prepolymers, branched polyesters and/or coatings are sometimes referred to as "BPA non intent" because BPA, including derivatives or residues thereof, are not intentionally added but may be present in trace amounts because of impurities or unavoidable contamination from the environment.
- the prepolymers, branched polyesters and/or coatings can also be substantially free and may be essentially free and/or may be completely free of bisphenol F and derivatives or residues thereof, including bisphenol F and bisphenol F diglycidyl ether ("BFDGE").
- BFDGE bisphenol F and bisphenol F diglycidyl ether
- substantially free as used in this context means the prepolymers, branched polyesters and/or coatings contain less than 1000 parts per million (ppm), "essentially free” means less than 100 ppm and "completely free” means less than 20 parts per billion (ppb) of any of the above mentioned compounds, derivatives or residues thereof.
- the present coatings can be applied to any substrates known in the art, for example, automotive substrates, industrial substrates, packaging substrates, wood flooring and furniture, apparel, electronics including housings and circuit boards including consumer electronics such as housings for computers, notebooks, smartphones, tablets, televisions, gaming equipment, computer equipment, computer accessories, MP3 players, and the like, glass and transparencies, sports equipment including golf balls, and the like.
- substrates can be, for example, metallic or non-metallic.
- Metallic substrates include tin, steel, tin-plated steel, chromium passivated steel, galvanized steel, aluminum, aluminum foil.
- Non-metallic substrates include polymeric, plastic, polyester, polyolefm, polyamide, cellulosic, polystyrene, polyacrylic, poly(ethylene naphthalate), polypropylene, polyethylene, nylon, EVOH, polylactic acid, other "green” polymeric substrates, poly(ethyleneterephthalate) ("PET”), polycarbonate, polycarbonate acrylobutadiene styrene (“PC/ABS”), polyamide, wood, veneer, wood composite, particle board, medium density fiberboard, cement, stone, glass, paper, cardboard, textiles, leather both synthetic and natural, and the like.
- the substrate can be one that has been already treated in some manner, such as to impart visual and/or color effect.
- the coatings of the present invention can be applied by any means standard in the art, such as electrocoating, spraying, electrostatic spraying, dipping, rolling, brushing, and the like.
- the coatings can be applied to a dry film thickness of 0.04 mils to 4 mils, such as 0.3 to 2 or 0.7 to 1.3 mils. In other embodiments the coatings can be applied to a dry film thickness of 0.1 mils or greater, 0.5 mils or greater 1.0 mils or greater, 2.0 mils or greater, 5.0 mils or greater, or even thicker.
- the coatings of the present invention can be used alone, or in combination with one or more other coatings.
- the coatings of the present invention can comprise a colorant or not and can be used as a primer, basecoat, and/or top coat. For substrates coated with multiple coatings, one or more of those coatings can be coatings as described herein.
- the present coatings can also be used as a packaging "size" coating, wash coat, spray coat, end coat, and the like.
- the coatings described herein can be either one component (“IK”), or multi-component compositions such as two component (“2K”) or more.
- IK composition will be understood as referring to a composition wherein all the coating components are maintained in the same container after manufacture, during storage, etc.
- a IK coating can be applied to a substrate and cured by any conventional means, such as by heating, forced air, and the like.
- the present coatings can also be multi-component coatings, which will be understood as coatings in which various components are maintained separately until just prior to application. As noted above, the present coatings can be thermoplastic or thermosetting.
- the coating is a clearcoat.
- a clearcoat will be understood as a coating that is substantially transparent or translucent. A clearcoat can therefore have some degree of color, opacity provided it does not make the clearcoat opaque or otherwise affect, to any significant degree, the ability to see the underlying substrate.
- the clearcoats of the present invention can be used, for example, in conjunction with a pigmented basecoat.
- the clearcoat can be formulated as is know in the coatings art.
- the coating comprises a colorant, such as a pigmented basecoat used in conjunction with a clearcoat, or as a pigmented monocoat.
- a colorant such as a pigmented basecoat used in conjunction with a clearcoat, or as a pigmented monocoat.
- Such coating layers are used, for example, in the automotive industry to impart a decorative and/or protective finish to a vehicle.
- Vehicle is used herein in its broadest sense and includes all types of vehicles, such as but not limited to cars, trucks, buses, vans, golf carts, motorcycles, bicycles, railroad cars and the like. It will be appreciated that the portion of the vehicle that is coated according to the present invention may vary depending on why the coating is being used. For example, anti- chip primers may be applied to some of the portions of the vehicle as described above.
- the present coatings When used as a colored basecoat or monocoat, the present coatings will typically be applied to those portions of the vehicle that are visible such as the roof, hood, doors trunk lid and the like, but may also be applied to other areas such as inside the trunk, inside the door and the like; they can also be applied to those portions of the car that are in contact with the driver and/or passengers, such as the steering wheel, dashboard, gear shift, controls, door handle and the like. Clearcoats will typically be applied to the exterior of a vehicle.
- the present invention is directed to a substrate coated at least in part with the coating of the present invention, wherein the substrate comprises a consumer electronic part.
- “Consumer electronic part” includes, for example, any part or housing of computers, notebooks, smartphones, tablets, televisions, gaming equipment, computer accessories, MP3 players, and the like.
- the coatings are typically applied to at least the exterior of the housing of such equipment, but may also be applied in whole or in part to the interior of such housing as well.
- the present coatings are particularly suitable for application to consumer electronics as they can provide the desired soft touch and durability.
- Coil coatings having wide application in many industries, are also substrates that can be coated according to the present invention; the present coatings are particularly suitable as coil coatings due to their unique combination of flexibility and hardness, as discussed above. Coil coatings also typically comprise a colorant.
- the coatings of the present invention are also suitable for use as packaging coatings.
- the application of various pretreatments and coatings to packaging is well established.
- Such treatments and/or coatings can be used in the case of metal cans, wherein the treatment and/or coating is used to retard or inhibit corrosion, provide a decorative coating, provide ease of handling during the manufacturing process, and the like.
- Coatings can be applied to the interior of such cans to prevent the contents from contacting the metal of the container. Contact between the metal and a food or beverage, for example, can lead to corrosion of a metal container, which can then contaminate the food or beverage. This is particularly true when the contents of the can are acidic in nature.
- the coatings applied to the interior of metal cans also help prevent corrosion in the headspace of the cans, which is the area between the fill line of the product and the can lid; corrosion in the headspace is particularly problematic with food products having a high salt content.
- Coatings can also be applied to the exterior of metal cans.
- Certain coatings of the present invention are particularly applicable for use with coiled metal stock, such as the coiled metal stock from which the ends of cans are made (“can end stock”), and end caps and closures are made (“cap/closure stock”). Since coatings designed for use on can end stock and cap/closure stock are typically applied prior to the piece being cut and stamped out of the coiled metal stock, they are typically flexible and extensible. For example, such stock is typically coated on both sides.
- the coated metal stock is punched.
- the metal is then scored for the "pop-top” opening and the pop-top ring is then attached with a pin that is separately fabricated.
- the end is then attached to the can body by an edge rolling process.
- a similar procedure is done for "easy open” can ends.
- a score substantially around the perimeter of the lid allows for easy opening or removing of the lid from the can, typically by means of a pull tab.
- the cap/closure stock is typically coated, such as by roll coating, and the cap or closure stamped out of the stock; it is possible, however, to coat the cap/closure after formation. Coatings for cans subjected to relatively stringent temperature and/or pressure requirements should also be resistant to popping, corrosion, blushing and/or blistering.
- the present invention is further directed to a package coated at least in part with any of the coating compositions described above.
- the package is a metal can.
- metal can includes any type of metal can, container or any type of receptacle or portion thereof used to hold something.
- a metal can is a food can; the term “food can(s)” is used herein to refer to cans, containers or any type of receptacle or portion thereof used to hold any type of food and/or beverage.
- Metal “bottles” that mimic the shape of glass bottles are also “metal cans” according to the present invention.
- metal can(s) specifically includes food cans and also specifically includes “can ends", which are typically stamped from can end stock and used in conjunction with the packaging of beverages.
- metal cans also specifically includes metal caps and/or closures such as bottle caps, screw top caps and lids of any size, lug caps, and the like.
- Metal cans can be used to hold other items as well as food and/or beverage, including but not limited to personal care products, bug spray, spray paint, and any other compound suitable for packaging in an aerosol can.
- the cans can include "two-piece cans” and "three-piece cans” as well as drawn and ironed one-piece cans; such one-piece cans often find application with aerosol products.
- Packages coated according to the present invention can also include plastic bottles, plastic tubes, laminates and flexible packaging, such as those made from PE, PP, PET and the like. Such packaging could hold, for example, food, toothpaste, personal care products and the like.
- the coating can be applied to the interior and/or the exterior of the package.
- the coating can be rollcoated onto metal used to make a two-piece food can, a three-piece food can, can end stock and/or cap/closure stock.
- the coating is applied to a coil or sheet by roll coating; the coating is then cured by radiation and can ends are stamped out and fabricated into the finished product, i.e. can ends.
- the coating is applied as a rim coat to the bottom of the can; such application can be by roll coating.
- the rim coat functions to reduce friction for improved handling during the continued fabrication and/or processing of the can.
- the coating is applied to caps and/or closures; such application can include, for example, a protective varnish that is applied before and/or after formation of the cap/closure and/or a pigmented enamel post applied to the cap, particularly those having a scored seam at the bottom of the cap.
- Decorated can stock can also be partially coated externally with the coating described herein, and the decorated, coated can stock used to form various metal cans.
- Substrates coated according to the present invention can be coated with any of the compositions described above by any means known in the art, such as spraying, rolling, dipping, brushing, flow coating and the like; the coating may also be applied by electrocoating when the substrate is conductive.
- the appropriate means of application can be determined by one skilled in the art based upon the type of substrate being coated and the function for which the coating is being used.
- the coatings described above can be applied over the substrate as a single layer or as multiple layers with multiple heating stages between the application of each layer, if desired.
- the coating composition may be cured by any appropriate means.
- polyester for example, although reference is made herein to "a" polyester, “a” branched polyester, “an” unsaturated acid/anhydride/ester, "a” polyol pre-polymer, "a” soft segment, “a” soft monomer, "a” polyol segment, “a” polyol segment monomer, “a” prepolymer, "a” crosslinker, and the like, one or more of each of these and any other components can be used.
- polymer refers to oligomers and both homopolymers and copolymers
- prefix “poly” refers to two or more. Including, for example and like terms means including for example but not limited to. When ranges are given, any endpoints of those ranges and/or numbers within those ranges can be combined within the scope of the present invention.
- Abrasion resistance was measured according to ASTM Method F2357.
- a branched polyester according to the present invention was prepared as follows. 650 grams of 2 -methyl- 1,3 -propanediol, 177 grams of adipic acid, 287 grams of isophthalic acid, 179 grams of phthalic anhydride, 223 grams of maleic anhydride and 1.5 grams of butylstannoic acid were added to a 3 -liter, 4-neck round bottom flask equipped with a stirrer, a steam-cooled column topped with a distillation head and a thermocouple. The contents were heated slowly under a flow of nitrogen gas. The contents of the flask were heated to about 95°C at which time they were melted and stirring was started.
- the batch was heated to 155°C at which time water began distilling. Heating was continued to a batch temperature of 220°C. 160 grams of water was removed from the reaction. The final acid value of the resin was measured as 3.8. The contents of the batch were cooled to 150°C and 316 grams of Aromatic 100 was added. The material in the flask was then cooled and poured out. The solids content was 81% by weight. The OH number of the resin was 50.2 at 81% solids. The weight average molecular weight of the product was 5700 against a polystyrene control. The Tg of the prepolymer was -11°C.
- a branched polyester according to the present invention was prepared as follows. 650 grams of 2 -methyl- 1,3 -propanediol, 282 grams of adipic acid, 166 grams of isophthalic acid, 179 grams of phthalic anhydride, 223 grams of maleic anhydride and 1.5 grams of butylstannoic acid were added to a 3 -liter, 4-neck round bottom flask equipped with a stirrer, a steam-cooled column topped with a distillation head and a thermocouple. The contents were heated slowly under a flow of nitrogen gas. The contents of the flask were heated to about 95°C at which time they were melted and stirring was started.
- the batch was heated to 155°C at which time water began distilling. Heating was continued to a batch temperature of 220°C. 162 grams of water was removed from the reaction. The final acid value of the resin was measured as 6.1. The contents of the batch were cooled to 150°C and 313 grams of Aromatic 100 was added. The material in the flask was then cooled and poured out. The solids content was 81% by weight. The OH number of the resin was 43 at 81% solids. The weight average molecular weight of the product was 6600 against a polystyrene control and the Tg of the prepolymer was -18°C.
- a branched polyester according to the present invention was prepared as follows. 650 grams of 2 -methyl- 1,3 -propanediol, 711 grams of adipic acid, 152 grams of maleic anhydride and 1.5 grams of butylstannoic acid were added to a 3- liter, 4-neck round bottom flask equipped with a stirrer, a steam-cooled column topped with a distillation head and a thermocouple. The contents were heated slowly under a flow of nitrogen gas. The contents of the flask were heated to about 112°C at which time they were melted and stirring was started. The batch was heated to 173°C at which time water began distilling. Heating was continued to a batch temperature of 220°C.
- a coating according to the present invention was prepared as follows: 59 grams of polyester resin from Example 1 , 17 grams of ethyl acetate, 5 grams of diacetone alcohol, 5 grams of PM acetate, and 0.4 grams of DISPERBYK-103 (a wetting and dispersing additive commercially available from BYK) were added to a half pint metal can equipped with an overhead mechanical stirrer. The above mixture was gently mixed for 5-10 minutes, and 6.5 grams of ACEMATT TS-100 silica (thermal silica commercially available from Evonik Industries) was subsequently added. The mixture was continued to mix under high speed for 20-30 minutes.
- SILOK-3200 a coating feeling agent commercially available from Guangzhou Silok Polymers Co., Ltd.
- BLS 292 a light stabilizer from Mayzo, Inc.
- dibutyltin dilaurate 0.1 grams
- polycarbonate substrate showed hardness of 4.2 N/mm 2 , a coefficient of friction of 0.06, a surface roughness of 42, and an abrasion resistance of 480 cycles.
- the coating was tested for stain resistance against common household products and exhibited stain resistance to mustard, ketchup, lipstick, sunscreen, petroleum jelly and hand lotion.
- a coating according to the present invention was prepared as follows: 59 grams of polyester resin from Example 2, 17 grams of ethyl acetate, 5 grams of diacetone alcohol, 5 grams of PM acetate, and 0.4 grams of DISPERBYK-103 were added to a half pint metal can equipped with an overhead mechanical stirrer. The above mixture was gently mixed for 5-10 minutes, and 6.5 grams of ACEMATT TS- 100 silica was subsequently added. The mixture was continued to mix under high speed for 20-30 minutes. A total of 1 gram of SILOK-3200, 0.6 grams of BLS 292 and 0.1 grams of dibutyltin dilaurate were finally added to the metal can and mixed for another 5 minutes.
- the resulting mixture was mixed with 16 grams of XPH80002 hardener and reduced with GXS73037 reducer to an appropriate spray viscosity.
- the resulting soft touch paint was sprayed on a polycarbonate substrate and cured at 60°C for 30 mins with a dry film build around 55 ⁇ .
- the final soft touch coating on polycarbonate substrate showed hardness of 3.3 N/mm 2 , a coefficient of friction of 0.07, a surface roughness of 44 and an abrasion resistance of 300 cycles.
- the coating was tested for stain resistance against common household products and exhibited stain resistance to ketchup, lipstick, sunscreen, petroleum jelly and hand lotion, while slight staining occurred with mustard.
- a coating according to the present invention was prepared as follows: 59 grams of polyester resin from Example 3, 17 grams of ethyl acetate, 5 grams of diacetone alcohol, 5 grams of PM acetate, and 0.4 grams of DISPERBYK-103 were added to a half pint metal can equipped with an overhead mechanical stirrer. The above mixture was gently mixed for 5-10 minutes, and 6.5 grams of ACEMATT TS- 100 silica was subsequently added. The mixture was continued to mix under high speed for 20-30 minutes. A total of 1 gram of SILOK-3200, 0.6 grams of BLS 292 and 0.1 grams of dibutyltin dilaurate were finally added to the metal can and mixed for another 5 minutes.
- the resulting mixture was mixed with 26 grams of XPH80002 hardener and reduced with GXS73037 reducer to an appropriate spray viscosity.
- the resulting soft touch paint was sprayed on a polycarbonate substrate and cured at 60°C for 30 mins with a dry film build around 55 ⁇ .
- the final soft touch coating on polycarbonate substrate showed hardness of 3.0 N/mm 2 , a coefficient of friction of 0.07, a surface roughness of 38, and an abrasion resistance of 350 cycles when measured after initial cure and 600 cycles after 5 days.
- the coating was tested for stain resistance against common household products and exhibited stain resistance to ketchup, sunscreen, petroleum jelly and hand lotion, while slight staining occurred with mustard and lipstick.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Laminated Bodies (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US14/245,399 US9115241B2 (en) | 2010-04-01 | 2014-04-04 | Branched polyester polymers and soft touch coatings comprising the same |
PCT/US2015/024012 WO2015153844A1 (en) | 2014-04-04 | 2015-04-02 | Branched polyester polymers and soft touch coatings comprising the same |
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EP3126427A1 true EP3126427A1 (en) | 2017-02-08 |
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Application Number | Title | Priority Date | Filing Date |
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EP15716685.1A Withdrawn EP3126427A1 (en) | 2014-04-04 | 2015-04-02 | Branched polyester polymers and soft touch coatings comprising the same |
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EP (1) | EP3126427A1 (en) |
JP (2) | JP6526048B2 (en) |
KR (1) | KR101811170B1 (en) |
CN (1) | CN106414530B (en) |
CA (1) | CA2944749C (en) |
MX (1) | MX2016013008A (en) |
MY (1) | MY176199A (en) |
RU (1) | RU2643808C1 (en) |
SG (1) | SG11201608263PA (en) |
TW (1) | TWI577712B (en) |
WO (1) | WO2015153844A1 (en) |
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US10035872B2 (en) | 2010-04-01 | 2018-07-31 | Ppg Industries Ohio, Inc. | Branched polyester-urethane resins and coatings comprising the same |
CN108473655B (en) * | 2015-12-14 | 2021-08-03 | Ppg工业俄亥俄公司 | Branched polyester-urethane resins and coatings comprising the same |
EP3667662B1 (en) | 2018-12-12 | 2022-08-10 | Panasonic Intellectual Property Corporation of America | Acoustic echo cancellation device, acoustic echo cancellation method and acoustic echo cancellation program |
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DE69410098T2 (en) * | 1993-08-12 | 1998-09-03 | Eastman Chem Co | WATER-DISPERSIBLE ACRYLIC-MODIFIED POLYESTER RESINS USED IN COATING AGENTS AND METHOD FOR THE PRODUCTION THEREOF |
AT409633B (en) * | 1999-01-18 | 2002-09-25 | Solutia Austria Gmbh | BINDERS FOR '' SOFT-FEEL '' LACQUERS |
US20040170774A1 (en) * | 2001-07-26 | 2004-09-02 | Luc Moens | Polymeric compositions |
WO2005080517A1 (en) * | 2004-02-12 | 2005-09-01 | Valspar Sourcing, Inc. | Methods of coating interior container surfaces and containers containing internal coatings |
BRPI0516760B1 (en) * | 2004-09-30 | 2016-10-11 | Sherwin Williams Co | coating composition, method of applying primer and sealer to a plastic substrate and electroconductive composition of sealer / primer |
EP1835000A1 (en) * | 2006-03-17 | 2007-09-19 | Cytec Surface Specialties Austria GmbH | Aqueous binders for coatings with improved gloss |
US20120121839A1 (en) * | 2009-03-25 | 2012-05-17 | Marian Henryk Szkudlarek | Process for preparing unsaturated polyester |
US9708504B2 (en) * | 2010-04-01 | 2017-07-18 | Ppg Industries Ohio, Inc. | Branched polyester polymers and coatings comprising the same |
US9695264B2 (en) * | 2010-04-01 | 2017-07-04 | Ppg Industries Ohio, Inc. | High functionality polyesters and coatings comprising the same |
-
2015
- 2015-04-02 TW TW104111014A patent/TWI577712B/en not_active IP Right Cessation
- 2015-04-02 EP EP15716685.1A patent/EP3126427A1/en not_active Withdrawn
- 2015-04-02 CN CN201580024958.7A patent/CN106414530B/en not_active Expired - Fee Related
- 2015-04-02 CA CA2944749A patent/CA2944749C/en active Active
- 2015-04-02 WO PCT/US2015/024012 patent/WO2015153844A1/en active Application Filing
- 2015-04-02 JP JP2016560731A patent/JP6526048B2/en not_active Expired - Fee Related
- 2015-04-02 RU RU2016143462A patent/RU2643808C1/en active
- 2015-04-02 MX MX2016013008A patent/MX2016013008A/en unknown
- 2015-04-02 MY MYPI2016001796A patent/MY176199A/en unknown
- 2015-04-02 KR KR1020167030813A patent/KR101811170B1/en active IP Right Grant
- 2015-04-02 SG SG11201608263PA patent/SG11201608263PA/en unknown
-
2019
- 2019-02-22 JP JP2019030307A patent/JP2019073738A/en not_active Withdrawn
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KR20160141820A (en) | 2016-12-09 |
CA2944749C (en) | 2019-03-26 |
CN106414530A (en) | 2017-02-15 |
KR101811170B1 (en) | 2018-01-25 |
JP2017517591A (en) | 2017-06-29 |
TW201546111A (en) | 2015-12-16 |
CN106414530B (en) | 2020-04-24 |
JP6526048B2 (en) | 2019-06-05 |
CA2944749A1 (en) | 2015-10-08 |
JP2019073738A (en) | 2019-05-16 |
SG11201608263PA (en) | 2016-10-28 |
MX2016013008A (en) | 2017-04-27 |
TWI577712B (en) | 2017-04-11 |
WO2015153844A1 (en) | 2015-10-08 |
RU2643808C1 (en) | 2018-02-06 |
MY176199A (en) | 2020-07-24 |
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