CA2944749C - Branched polyester polymers and soft touch coatings comprising the same - Google Patents

Branched polyester polymers and soft touch coatings comprising the same Download PDF

Info

Publication number: CA2944749C
Authority: CA; Canada
Prior art keywords: polyester; coating; acid; prepolymer; anhydride
Prior art date: 2014-04-04
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.): Active

Application number

CA2944749A

Other languages

English (en)

French (fr)

Other versions

CA2944749A1 (en

Inventor

Renlong Gao

Irina G. Schwendeman

Debra L. Singer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

PPG Industries Ohio Inc

Original Assignee

PPG Industries Ohio Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2014-04-04

Filing date

2015-04-02

Publication date

2019-03-26

2014-04-04 Priority claimed from US14/245,399 external-priority patent/US9115241B2/en

2015-04-02 Application filed by PPG Industries Ohio Inc filed Critical PPG Industries Ohio Inc

2015-10-08 Publication of CA2944749A1 publication Critical patent/CA2944749A1/en

2019-03-26 Application granted granted Critical

2019-03-26 Publication of CA2944749C publication Critical patent/CA2944749C/en

Status Active legal-status Critical Current

2035-04-02 Anticipated expiration legal-status Critical

Links

238000000576 coating method Methods 0.000 title claims abstract description 149
229920000728 polyester Polymers 0.000 title claims abstract description 140
229920000642 polymer Polymers 0.000 title claims description 30
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 86
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 29
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
239000004417 polycarbonate Substances 0.000 claims description 9
229920000515 polycarbonate Polymers 0.000 claims description 9
QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 8
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
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-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
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 60
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 22
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 20
239000007787 solid Substances 0.000 description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
239000008199 coating composition Substances 0.000 description 13
239000002105 nanoparticle Substances 0.000 description 13
239000000047 product Substances 0.000 description 13
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
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 8
125000000524 functional group Chemical group 0.000 description 8
239000000463 material Substances 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
239000004793 Polystyrene Substances 0.000 description 7
230000015572 biosynthetic process Effects 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
229920001187 thermosetting polymer Polymers 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
229940048053 acrylate Drugs 0.000 description 5
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
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
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
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-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
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
WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 2
239000002131 composite material Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
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
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
239000010954 inorganic particle Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
239000004611 light stabiliser Substances 0.000 description 2
239000004973 liquid crystal related substance Substances 0.000 description 2
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
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-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
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
239000000843 powder Substances 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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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
150000002989 phenols Chemical class 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
229920000098 polyolefin Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001296 polysiloxane 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
MTTKOBXFUGIESR-UHFFFAOYSA-N prop-1-ene-1,3-diol Chemical compound OCC=CO MTTKOBXFUGIESR-UHFFFAOYSA-N 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
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

- 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
- 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
- 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

Landscapes

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)

CA2944749A 2014-04-04 2015-04-02 Branched polyester polymers and soft touch coatings comprising the same Active CA2944749C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US14/245,399 US9115241B2 (en)	2010-04-01	2014-04-04	Branched polyester polymers and soft touch coatings comprising the same
US14/245,399		2014-04-04
PCT/US2015/024012 WO2015153844A1 (en)	2014-04-04	2015-04-02	Branched polyester polymers and soft touch coatings comprising the same

Publications (2)

Publication Number	Publication Date
CA2944749A1 CA2944749A1 (en)	2015-10-08
CA2944749C true CA2944749C (en)	2019-03-26

Family

ID=52875327

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2944749A Active CA2944749C (en)	2014-04-04	2015-04-02	Branched polyester polymers and soft touch coatings comprising the same

Country Status (11)

Country	Link
EP (1)	EP3126427A1 (es)
JP (2)	JP6526048B2 (es)
KR (1)	KR101811170B1 (es)
CN (1)	CN106414530B (es)
CA (1)	CA2944749C (es)
MX (1)	MX387573B (es)
MY (1)	MY176199A (es)
RU (1)	RU2643808C1 (es)
SG (1)	SG11201608263PA (es)
TW (1)	TWI577712B (es)
WO (1)	WO2015153844A1 (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US10035872B2 (en)	2010-04-01	2018-07-31	Ppg Industries Ohio, Inc.	Branched polyester-urethane resins and coatings comprising the same
RU2018125548A (ru) *	2015-12-14	2020-01-16	Ппг Индастриз Огайо, Инк.	Разветвлённые полиэфир-уретановые смолы и включающие их покрытия
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

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2169299A1 (en) *	1993-08-12	1995-02-23	Thauming Kuo	Water-dispersible acrylic-modified polyester resins used in coatings and process for their preparation
AT409633B (de) *	1999-01-18	2002-09-25	Solutia Austria Gmbh	Bindemittel für ''soft-feel''-lacke
AU2002325893A1 (en) *	2001-07-26	2003-02-17	Ucb, S.A.	Unsaturated powder coating compositions
KR20070001160A (ko) *	2004-02-12	2007-01-03	발스파 소싱 인코포레이티드	내부 용기 표면의 코팅 방법 및 내부 코팅을 함유하는 용기
BRPI0516760B1 (pt) *	2004-09-30	2016-10-11	Sherwin Williams Co	composição de revestimento, método de aplicação de primer e selador a um substrato plástico e composição eletrocondutora de selador/primer
EP1835000A1 (en) *	2006-03-17	2007-09-19	Cytec Surface Specialties Austria GmbH	Aqueous binders for coatings with improved gloss
JP2012521470A (ja) *	2009-03-25	2012-09-13	ディーエスエムアイピーアセッツビー．ブイ．	不飽和ポリエステルの製造方法
US9695264B2 (en) *	2010-04-01	2017-07-04	Ppg Industries Ohio, Inc.	High functionality polyesters and coatings comprising the same
US9708504B2 (en) *	2010-04-01	2017-07-18	Ppg Industries Ohio, Inc.	Branched polyester polymers and coatings comprising the same

2015
- 2015-04-02 RU RU2016143462A patent/RU2643808C1/ru active
- 2015-04-02 MY MYPI2016001796A patent/MY176199A/en unknown
- 2015-04-02 TW TW104111014A patent/TWI577712B/zh not_active IP Right Cessation
- 2015-04-02 CN CN201580024958.7A patent/CN106414530B/zh not_active Expired - Fee Related
- 2015-04-02 WO PCT/US2015/024012 patent/WO2015153844A1/en not_active Ceased
- 2015-04-02 SG SG11201608263PA patent/SG11201608263PA/en unknown
- 2015-04-02 MX MX2016013008A patent/MX387573B/es unknown
- 2015-04-02 CA CA2944749A patent/CA2944749C/en active Active
- 2015-04-02 KR KR1020167030813A patent/KR101811170B1/ko not_active Expired - Fee Related
- 2015-04-02 EP EP15716685.1A patent/EP3126427A1/en not_active Withdrawn
- 2015-04-02 JP JP2016560731A patent/JP6526048B2/ja not_active Expired - Fee Related
2019
- 2019-02-22 JP JP2019030307A patent/JP2019073738A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
WO2015153844A1 (en)	2015-10-08
RU2643808C1 (ru)	2018-02-06
EP3126427A1 (en)	2017-02-08
TWI577712B (zh)	2017-04-11
MX387573B (es)	2025-03-18
MY176199A (en)	2020-07-24
JP6526048B2 (ja)	2019-06-05
MX2016013008A (es)	2017-04-27
CN106414530A (zh)	2017-02-15
SG11201608263PA (en)	2016-10-28
JP2017517591A (ja)	2017-06-29
TW201546111A (zh)	2015-12-16
CN106414530B (zh)	2020-04-24
KR20160141820A (ko)	2016-12-09
KR101811170B1 (ko)	2018-01-25
JP2019073738A (ja)	2019-05-16
CA2944749A1 (en)	2015-10-08

Publication	Publication Date	Title
US9115241B2 (en)	2015-08-25	Branched polyester polymers and soft touch coatings comprising the same
US10273381B2 (en)	2019-04-30	Branched polyester polymers and coatings comprising the same
CA2793986C (en)	2015-05-26	High functionality polyesters and coatings comprising the same
US10392467B2 (en)	2019-08-27	Coatings comprising branched polyester-urethane resins
CA2944749C (en)	2019-03-26	Branched polyester polymers and soft touch coatings comprising the same
US20160060390A1 (en)	2016-03-03	Branched polyester resins and easy to clean coatings comprising the same
CA3008414A1 (en)	2017-06-22	Branched polyester-urethane resins and coatings comprising the same
HK1179587B (en)	2016-04-08	Branched polyester polymers and coatings comprising the same, base material coated using the coatings

Legal Events

Date	Code	Title	Description
2016-11-02	EEER	Examination request	Effective date: 20161003