MXPA01005189A - Coating compositions and coatings formed therefrom - Google Patents
Coating compositions and coatings formed therefromInfo
- Publication number
- MXPA01005189A MXPA01005189A MXPA/A/2001/005189A MXPA01005189A MXPA01005189A MX PA01005189 A MXPA01005189 A MX PA01005189A MX PA01005189 A MXPA01005189 A MX PA01005189A MX PA01005189 A MXPA01005189 A MX PA01005189A
- Authority
- MX
- Mexico
- Prior art keywords
- group
- further characterized
- polymer
- silane
- coating
- Prior art date
Links
- 239000008199 coating composition Substances 0.000 title claims abstract description 40
- 229920000642 polymer Polymers 0.000 claims abstract description 56
- 239000011248 coating agent Substances 0.000 claims abstract description 29
- 238000000576 coating method Methods 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 229910000077 silane Inorganic materials 0.000 claims abstract description 26
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical group NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims abstract description 24
- BLRPTPMANUNPDV-UHFFFAOYSA-N silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000758 substrate Substances 0.000 claims abstract description 5
- -1 polysiloxanes Polymers 0.000 claims description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 23
- 229920000058 polyacrylate Polymers 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 125000003700 epoxy group Chemical group 0.000 claims description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229920002635 polyurethane Polymers 0.000 claims description 12
- 239000004814 polyurethane Substances 0.000 claims description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- 229920000728 polyester Polymers 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 7
- IBVAQQYNSHJXBV-UHFFFAOYSA-N Adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920000515 polycarbonate Polymers 0.000 claims description 5
- 239000004417 polycarbonate Substances 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 229920001721 Polyimide Polymers 0.000 claims description 4
- 239000004642 Polyimide Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 229920001296 polysiloxane Polymers 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000004756 silanes Chemical class 0.000 abstract description 5
- 239000000049 pigment Substances 0.000 abstract description 3
- 229920000548 poly(silane) polymer Polymers 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000003973 paint Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- FIRQYUPQXNPTKO-UHFFFAOYSA-N CTK0I2755 Chemical compound N[SiH2]N FIRQYUPQXNPTKO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000000903 blocking Effects 0.000 description 4
- 239000004568 cement Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 229940042795 Hydrazides for tuberculosis treatment Drugs 0.000 description 3
- 229920000126 Latex Polymers 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 229920001228 Polyisocyanate Polymers 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 239000011436 cob Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000005676 cyclic carbonates Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-Aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-Amino-2-propanol Chemical group CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N 2-hydroxyethyl 2-methylacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- FEIQOMCWGDNMHM-UHFFFAOYSA-M 5-phenylpenta-2,4-dienoate Chemical compound [O-]C(=O)C=CC=CC1=CC=CC=C1 FEIQOMCWGDNMHM-UHFFFAOYSA-M 0.000 description 1
- PGXIJLSNAVMTTA-UHFFFAOYSA-N 6-aminohexyl prop-2-enoate Chemical class NCCCCCCOC(=O)C=C PGXIJLSNAVMTTA-UHFFFAOYSA-N 0.000 description 1
- XXROGKLTLUQVRX-UHFFFAOYSA-N Allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 1
- SIOVKLKJSOKLIF-UHFFFAOYSA-N Bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
- NKGRQISIYNXARY-UHFFFAOYSA-N C(C=C)(=O)OCOOC1(C(C(=O)O)C=CC=C1)C(=O)O Chemical compound C(C=C)(=O)OCOOC1(C(C(=O)O)C=CC=C1)C(=O)O NKGRQISIYNXARY-UHFFFAOYSA-N 0.000 description 1
- ZPEZXPLJZDZHKW-UHFFFAOYSA-N CCCCCCCCCCCCCC(CCCC)[Si](Cl)(Cl)Cl Chemical compound CCCCCCCCCCCCCC(CCCC)[Si](Cl)(Cl)Cl ZPEZXPLJZDZHKW-UHFFFAOYSA-N 0.000 description 1
- YGHUUVGIRWMJGE-UHFFFAOYSA-N Chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N Crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N Dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N Dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N Glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000001321 HNCO Methods 0.000 description 1
- NEXSMEBSBIABKL-UHFFFAOYSA-N Hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 1
- 229940102253 ISOPROPANOLAMINE Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N Itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N Methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- NHBRUUFBSBSTHM-UHFFFAOYSA-N N'-[2-(3-trimethoxysilylpropylamino)ethyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCCN NHBRUUFBSBSTHM-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N N'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- UTSYWKJYFPPRAP-UHFFFAOYSA-N N-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCNC(=O)C=C UTSYWKJYFPPRAP-UHFFFAOYSA-N 0.000 description 1
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 1
- MSPCIZMDDUQPGJ-UHFFFAOYSA-N N-methyl-N-(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)N(C)C(=O)C(F)(F)F MSPCIZMDDUQPGJ-UHFFFAOYSA-N 0.000 description 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N N-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
- LWFWUJCJKPUZLV-UHFFFAOYSA-N N-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N Silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N Silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N Solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N Tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N Trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N Trimethylsilyl chloride Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N Trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N Trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- OPARTXXEFXPWJL-UHFFFAOYSA-N [acetyloxy-bis[(2-methylpropan-2-yl)oxy]silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)(C)C)OC(C)(C)C OPARTXXEFXPWJL-UHFFFAOYSA-N 0.000 description 1
- TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005122 aminoalkylamino group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N butyl 2-methylprop-2-enoate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- MXOSTENCGSDMRE-UHFFFAOYSA-N butyl-chloro-dimethylsilane Chemical compound CCCC[Si](C)(C)Cl MXOSTENCGSDMRE-UHFFFAOYSA-N 0.000 description 1
- YCRYJWJNPWZJSR-UHFFFAOYSA-O butylideneazanium Chemical group [CH2-]CCC=[NH2+] YCRYJWJNPWZJSR-UHFFFAOYSA-O 0.000 description 1
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 1
- GZGREZWGCWVAEE-UHFFFAOYSA-N chloro-dimethyl-octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](C)(C)Cl GZGREZWGCWVAEE-UHFFFAOYSA-N 0.000 description 1
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 1
- OOCUOKHIVGWCTJ-UHFFFAOYSA-N chloromethyl(trimethyl)silane Chemical compound C[Si](C)(C)CCl OOCUOKHIVGWCTJ-UHFFFAOYSA-N 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- SJJCABYOVIHNPZ-UHFFFAOYSA-N cyclohexyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C1CCCCC1 SJJCABYOVIHNPZ-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000004815 dispersion polymerization Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003628 erosive Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N isocyanate Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000000414 obstructive Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003211 photoinitiator Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ZXDUPDQEFOYLOM-UHFFFAOYSA-O propylideneazanium Chemical group [CH2-]CC=[NH2+] ZXDUPDQEFOYLOM-UHFFFAOYSA-O 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- OTTUQUOINFJTBJ-UHFFFAOYSA-N tetrakis(2-ethoxyethyl) silicate Chemical compound CCOCCO[Si](OCCOCC)(OCCOCC)OCCOCC OTTUQUOINFJTBJ-UHFFFAOYSA-N 0.000 description 1
- JSECNWXDEZOMPD-UHFFFAOYSA-N tetrakis(2-methoxyethyl) silicate Chemical compound COCCO[Si](OCCOC)(OCCOC)OCCOC JSECNWXDEZOMPD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- MSRJTTSHWYDFIU-UHFFFAOYSA-N triethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N α-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
Abstract
Coating compositions contain a polymer and a silane, the polymer having at least one reactive group and at least one hydrazide group. The silane can be selected from the group consisting of silanes and polysilanes. Optionally, the coating composition includes a pigment. Coatings made from such compositions are also described. Methods of preparing a coating by applying the coating composition to a substrate and curing to form a film are also described herein.
Description
COATING COMPOSITIONS AND COATINGS FORMED FROM THEMSELVES
DESCRIPTIVE MEMORY
This description relates to novel coating compositions prepared from a reactive polymer, a hydrazide compound and a silane compound. The coating compositions, which may be free of formaldehyde and free of isocyanate, are cured to provide an interpenetrating network (IPN) coating with excellent properties. The paintings can be considered within two general categories, mainly, water-based paints and solvent-based paints. The category of paint suitable for a given application depends on the conditions that the painting experiences. Conventional water based paints have generally been considered inferior to solvent based paints in terms of weather resistance, solvent resistance and adhesion. However, recently, the use of solvent-based paints has become unfavorable, in terms of the environment, with emphasis on achieving acceptable results with paints with a relatively lower volatile organic content ("VOC"). Specifically, efforts have been made to provide paints or coatings that are free of isocyanate and free of formaldehyde having acceptable physical characteristics.
It is therefore an object of the present invention to provide a coating composition which is free of isocyanate and free of formaldehyde, exhibiting good adhesion, durability, chemical resistance, water resistance and resistance to printing. This desired combination of properties has now been achieved by the coating compositions described herein. The novel coating compositions disclosed herein include a polymer and a silane. The polymer has at least one reactive functional group and a hydrazide group. The silane can be selected from the group consisting of silanes and polysilanes. Optionally, the coating composition includes a pigment. Coatings made from said compositions are also described. Also described herein are methods for preparing a coating by applying the coating composition to a substrate and curing it to form a film. Preferred coating compositions in accordance with this disclosure are free of formaldehyde and isocilanate free, can be cured with air or at elevated temperature and provide coatings that exhibit improved adhesion to the substrate, improved printing and blocking resistance and improved solvent and water resistance . The novel coating compositions in accordance with this disclosure include, (a) a polymer having at least one group
In addition to functional reactive UMite, the polymer also has a hydrazide group attached thereto; and (b) a silane. Polymers useful for forming the coating compositions include, for example, acrylic polymers, modified acrylic polymers, polyepoxides, polyesters, polycarbonates, polyurethanes, polyamides, polyimides, polysioxanes, polycarbamates and mixtures thereof. The molecular weight of the polymer is not critical. The polymer will generally have a molecular weight of 2,000 to 2,000,000 and preferably 100,000 to 1,000,000. The polymer includes reactive functional groups. The functional groups may provide a binding site for the hydrazide-containing compound and may also provide a site for interlacing by the silane compound as described in detail below. Suitable reactive functional groups include, for example, carboxyl, hydroxyl, epoxy, aminoalkylamino, multi-functional amine, amido and keto groups or combinations thereof. The degree of substitution of the reactive functional groups is not critical, but can preferably be adjusted to provide a coating with the desired characteristics. For example, in this way, where carboxyl groups are present in the polymer, acid numbers of less than about 20 should provide adequate interlacing to form a coating. However, if a coating that can withstand 200 rubs with MEK is desired, an acid number should be used on the scale of about 40 to
I SAID? ** Íí mé ^^ ^^^^^^^^^^^ l ^ ^ approximately 80. The polymer can self-entangle or heal with U.V. It is within the field of view of the person skilled in the art to prepare suitable polymers containing reactive functional groups. Suitable polymers are commercially available from a variety of suppliers. Where acrylic polymers are used, said polymers can be prepared from monomers such as acrylic acid and methacrylic acid, alkyl and cycloalkyl acrylates and methacrylates having 1 to 18, preferably 4 to 13, carbon atoms in the alkyl or cycloalkyl portion , Or mixtures of said monomers. Examples of these include methylacrylate, methyl methacrylate, ethylacrylate, ethyl methacrylate, butylacrylate, n-butylacrylate, n-butyl methacrylate, 2-ethylhexylacrylate, cyclohexyl methacrylate, and 2-ethylhexyl methacrylate. The reactive functionality in the acrylic polymer can
is incorporated by reacting functional monomers with carboxyl, hydroxyl, epoxy, amino, and alkylamino functional groups. The carboxyl-containing monomers include acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, 2-acryloxymethoxy-O-phthalic acid, 2-acryloxy-1-methylethoxy-0-hexafyrnephthalic acid. The
Hydroxy functional monomers include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate, allyl alcohol, and metal alcohol. Functional epoxy monomers include glycidyl methacrylate. Examples of acrylates and
MUMETHYL Alkylamino methacrylates include aminomethyl, aminopropyl, aminobutyl and aminohexylacrylates and methacrylates, dimethylaminoethylacrylate, and dimethylaminoethyl methacrylate. Other suitable monomers include N- • alkoxymethylacrylamide, and N- (butoxymethyl) acrylamide. Other ethylenically unsaturated monomers such as vinyl, styrene, α-methylstyrene, vinyltoluene, t-butylstyrene may also be included to provide the desired physical characteristics. Particularly useful polymers are carboxylated styrene acrylate polymers. Modified acrylics can also be used as the
acrylic polymer. Examples of these include acrylics modified with polyester or acrylics modified with polyurethane, which are also known in the art. An example of a polyester-modified acrylic is an acrylic polymer modified with d-caprolactone. Said polyester modified acrylic is described in the patent of E.U.A. No. 4,546,046 to Etxell et al.
Acrylics modified with polyurethane are well known in the art. An example is set forth in the patent of E.U.A. No. 4,584,354, the disclosure of which is incorporated herein by reference. Polyesters having hydroxyl groups, acid groups, or amino groups as reactive functional groups can also be used
as the polymer in the compositions herein. Such polyesters are well known in the art, and can be prepared by polyesterification of organic polycarboxylic acids (for example, phthalic acid, hexahydrophthalic acid, adipic acid, maleic acid) or their anhydrides,
m Émt_ ^ ^^^^ with organic polyols containing primary or secondary hydroxyl groups. The polyurethanes useful as the polymer in the compositions herein can be prepared by reacting polyisocyanate and polyol with an equivalent OH: NCO ratio greater than 1: 1, to obtain polyurethanase with terminal hydroxyl functionality. In this case, the blocking of the isocyanate occurs simultaneously with the synthesis of the polyurethane resin. Alternatively, the polyurethane can be formed by reacting the polyisocyanate and polyol with an OH: NCO ratio of less than 1: 1. In this case, where an excess of isocyanate is used, the polyurethane having unreacted isocyanate functionality is subsequently reacted with a blocking agent. Suitable blocking agents include reactive alcohols or amines. Examples of these are trimethylolpropane, ethanolamine, diethanolamine, Solketal, diols, triols, or a mixture of diols and triols. Preferably, any unreacted socianates are removed before using the polyurethane as the polymer. Suitable carbamate functional polymers can be prepared from an acrylic monomer having a carbamate functionality in the ester portion of the monomer. Such monomers are well known in the art and are described, for example, in U.S. Patents. 3,479,328; 3,674,838; 4,126,747; 4,279,833; and 4,340,497, the descriptions of which are incorporated herein by reference. A synthesis method involves the reaction of a hydroxy ester with urea to form the carboxylate of carbamyloxy
.jMMá ^ iiüi ifaáA ^ ^ M (that is, acrylic modified with carbamate). Another synthetic method reacts an ester of unsaturated a, b acid with a hydroxy carbamate ester to form the carboxylate carbamyloxy. Yet another technique involves the formation of a hydroxyalkyl carbamate by reacting a primary or secondary amine or diamine with a cyclic carbonate such as ethylene carbonate. The hydroxyl group in the hydroxyalkyl carbamate is subsequently esterified by reaction with acrylic or methacrylic acid to form the monomer. Other methods for preparing acrylic monomers modified with carbamate are described in the art, and can also be used. The acrylic monomer can subsequently be polymerized together with other ethylenically unsaturated monomers, if desired, by techniques well known in the art. An alternative route for preparing a polymer useful in the coating compositions herein is to react an already formed polymer such as an acrylic polymer with another component to form a carbamate functional group attached to the polymer backbone, as described in US patent 4,758,632, the disclosure of which is incorporated herein by reference. One technique for preparing useful polymers involves thermally decomposing urea (to emit ammonia and HNCO) in the presence of a hydroxy-functional acrylic polymer to form a carbamate-functional acrylic polymer. Another technique involves reacting the hydroxyl group of a hydroxyalkyl carbamate with the isocyanate group of an acrylic or isocyanate-functional vinyl monomer to form the acrylic
carbamate-functional. Isocyanate-functional acrylics are known in the art and are described, for example, in the US patent. 4,301, 257, the disclosure of which is incorporated herein by reference. Isocyanate vinyl monomers are well known in the art and include meta-isopropenyl-a-a-dimethylbecil isocyanate. Yet another technique is to react the cyclic carbonate group in cyclic carbonate-functional acrylic with ammonia to form the carbamate-functional acrylic. Cyclic carbonate-functional acrylic polymers are known in the art and are described, for example, in the U.S.A. 2,979,514, the disclosure of which is incorporated herein by reference. A more difficult, but viable way to prepare the polymer is to transesterify an acrylate polymer with a hydroxyalkyl carbamate. The polymer containing reactive functional groups is preferably provided in the form of a latex, the term "latex" is used herein in a broad sense to mean, generally any aqueous dispersion of a water insoluble polymer, the polymer being present in shape of particles. A compound is grafted to the polymer containing a hydrazide group. Preferably, the hydrazide group has the formula:
ji ^ sá ik ai? ^ i k where Ri and R2 each independently represents H or substituted or unsubstituted alkyl. In one embodiment, the compound containing a hydrazide group also comprises a hindered amine group, as is frequently found in the compounds, known as hindered amine light stabilizing compounds (HALS). An example of said compound has the formula:
In another embodiment, the compound containing the hydrazide group has the formula:
wherein R3 and R4 each independently represent H or substituted or unsubstituted alkyl, and R5 represents substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or
wherein L represents a divalent linking group, -NH- or -O-. The linking group is preferably aliphatic, but may also be aromatic, cycloaliphatic, or heterocyclic. Preferably, at least one of R3 or R4, and
• minus one of R6 and R7 represents hydrogen. In a preferred embodiment, all R3, R4, R5, and Re represent hydrogen. The compounds containing the hydrazide group can be prepared from aliphatic organic acids, such as acetic acid, propionic acid, n-octanoic acid, adipic acid, oxalic acid, sebasic acid and the like. The acid groups typically react with hydrazine,
as is known in the art, to produce the hydrazide derivative of the acid. A compound containing the preferred hydrazide group is adipic dihydrazide. Examples of other useful compounds comprising hydrazide groups include hydrazides of the formula R- (CONH-NH2) n; bis-hydrazides
the formula NH2-NH-CO-NHNH2; semicarbazides of the formula RNH-CO-NHNH2; thiohydrazides of the formula RNH-CS-NHNH2. In each of the above formulas for the compounds containing the hydrazide group, n is a positive integer of at least 1. In a preferred embodiment n = 2. R can be hydrogen (except for hydrazides or thiohydrazides when n is 1) or
an organic radical. Useful organic radicals include aliphatic, cycloaliphatic, aromatic, or heterocyclic groups, preferably 1 to 20 carbon atoms. The R groups must be free of substituents that are reactive with hydrazide groups.
adaMdaA || É i | i | Wka | BHBM || H | M Polyhydrazides (eg hydrazides or thiohydrazides where n> 2) are preferably used to inorate the hydrazide groups in the polymer by reacting one of the hydrazide groups with a hydrazide-reactive group in the polymer. The polyhydrazide can react in the polymer by reacting a polyhydrazide with an acrylic or polyester polymer with one or more anhydride or epoxy groups. Alternatively, the hydrazine can react directly with the reactive functional groups in the polymer (eg, with acid groups in an acrylic polymer) to form a functional hydrazide polymer. The conditions for reacting the hydrazide compound with the polymer are within the realm of those skilled in the art. Typically, the hydrazide compound is simply mixed in a dispersion containing the polymer to effect grafting of the hydrazine group in the polymer. If desired, the hydrazide compound can be mixed with a solvent before addition to the polymer dispersion. The amount of the added hydrazide compound is not critical,) but will preferably depend on the number of factors including the degree of substitution of reactive functional groups in the polymer and the desired characteristics of the final coating. Typically, the hydrazide compound will be added in an amount of from about 0.25 to about 10% by weight, preferably from 0.5 to about 5.0% by weight based on the weight of the total solids content of the coating composition. As will be appreciated by those skilled in the art, since in a dispersion the
* '*' •• '- * "* - *. I» ti? .. * -m. .i ". * ,. * l *»? * ^ ... ..... a ^ A If the polymer will bend itself to form particles or micelles, the hydrazide compound will react mainly with reactive functional groups located on the outside of the particle or micelle. , the reactive functional groups within the particle or micelle 5 will remain available for entanglement by means of the silane acing to the molecular cleavages of the polymer when removed from the water or other solvent come from the coating composition In particularly useful embodiments, a sufficient number of the reactive groups on the outside of the polymer particle or micelle is made
• react with the hydrazide compound to avoid excessive gelation after addition of silane. This will allow the coating composition to be prepared as a package system. To form the coating compositions herein, the hydrazide containing polymers are combined with a silane of the
formula
wherein n = 1 to 1, 000, preferably 1 to 100, more preferably 1 to 10; R 20 is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms (such as, for example, a methyl, phenyl, alkyl or aryl group); Ri is the same or different in each case and is a selected portion of the group consisting of halogen, hydrogen, alkoxy, hydroxy groups,
-am amino and epoxy; and R2 may be the same or different in each case and is selected from the group consisting of R and Ri as defined above. Aminosilanes and epoxysilanes are silanes in particular
• useful for making the coating compositions herein. The 5 suitable silanes are commercially available from a variety of suppliers. Specific examples of suitable silanes include: allytrimethoxysilane; allyltrimethylsilane; ^ 10 N- (2-aminoethyl) -3-aminopropyl-methyldimethoxysilane; N-2-aminoetyl-3-aminopropyltrimethoxylane; 3-aminopropylmethyldiethoxysilane; 3-aminopropyltriethoxysilane; 3-aminopropyltrimethoxysilane; 15 b1- (dimethylamino) dimethylsilane; bis- (n-methylbenzamide) ethoxymethylsalon; bis (trimethylsilyl) acetamide; n-butyldimethylchlorosilane; t-butyldimethylchlorosilane; Chloromethyltrimethylsilane; 3-chloropropyltriethoxysilane; 3-chloropropyltrimethoxysilane; di-t-butoxydiacetoxysilane;
n, n-diethylaminotrimethylsilane; dimethylchlorosilane; dimethyldichlorosilane; • dimethyldiethoxysilane; 5-dimethylethoxysilane; dimethyloctadecylchlorosilane; diphenyldimethoxysilane; 1,3-divinyltetramethyldisilane; 1,3-divinyltetramethyldisiloxane; ^ 10-ethyltriacetoxysilane; (3-glycidoxypropyl) methodoxyethanol; (3-glycidoxypropyl) trimethoxysilane; hexamethyldisilane; isobutyltrimethoxysilane; 3-mercaptopropylmethyldimethoxysilane; 3-mercaptopropyltrimethoxysilane; 3-mercaptopropyltriethoxysilane; 3-methacryloxypropyltrimethoxysilane; 3-methacryloxypropyltrys (methylsoxy) slan; 20-methylaminopropyltrimethoxysilane; methylcyclohexydichlorosilane; methylcyclohexyldimethoxysilane; methyltriacetoxysilane;
. ? * t.? - ~ «, ..,. TO.. , ".,*.., ,._. ,. ^ t ~ ~ tot »» * »« .. »- ^ .. ^. methyltriethoxysilane; methyltrimethoxysilane; • n-methyl-n-trimethylsilyltrifluoroacetamide 5-octadecyltrichlorosilane; octyl trichlorosilane; n-octyltriethoxysilane; phenyltriethoxysilane; phenyltrimethoxysilane; ^ 10 tetra-n-butoxysilane; tetrachlorosilane; tetraethoxysilane (teos); tetrakis (2-ethoxyethoxy) silane; tetrakis (2-methoxyethoxy) silan; 15 tetramethoxysilane; tetrapropoxysilane; trichlorosilane; triethylchlorosilane; triethylsilane; Trimethoxysilylpropyl diethylenetriamine; n-trimethoxy-silicon-propyl-n, n, n -trimethyl ammonium chloride; trimethylbromosilane; trimethylchlorosilane;
• fflB-i "", - "trimethylsilylacetamide, trimethylsilylioid, trimethylsilylnitrile, trimethylsilyl trifluoromethanesulfonate, vinyl dimethylchlorosilane, vinylmethyldichlorosilane, vinylmethyldiethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, The amount of silane used is not it is critical, but preferably depends on a number of factors including the degree of substitution of reactive functional groups in the polymer and the desired characteristics of the final coating.You can use as little as about 0.25% by weight based on the total weight of the solids content of the coating composition to provide a coating However, if a coating that can withstand 200 rubs with MEK is desired, silane amounts of about 0.25% to about 10.0% by weight can be used to form a cured coating , one or more of the polymers are intertwined as described using a packing system or a two-pack system. In a packaging system, the polymer combines with the silane to form a stable paint system at storage temperatures. In a two-pack system, the polymer and the silane are kept separate just before or in the application of the composition. Usefully, an external catalyst (such as an inorganic acid) is not needed to cure the preferred compositions in accordance with this disclosure. The coating compositions of the present invention can be clear base coat and coating compositions. The composition may be in the form of a substantially solid powder, a dispersion, or in a substantially liquid state. The liquid coatings can go in the solvent or in water. The coatings may also include solvents, pigments, catalysts, hindered amine light stabilizers, ultraviolet light absorbers, rheology control additives, photoinitiators and other additives known to those skilled in the art. The coating compositions can be coated in the article by a number of techniques well known in the art. These include, for example, spray coating, dip coating, flow coating, roll coating, curtain coating 20, vacuum coating, and the like. After an article has been coated with the layers described above, the composition is subjected to conditions for curing the coating layers. The curing action is usually initiated during or after the removal of the solvent and / or the
tíriiir. ifh frf "» * - * - "" "'"' * '"" ** - * -' • * - - ^ ... fß j ^ M dispersant, although air curing or at room temperature can be used useful with the coating compositions described herein, heat curing is preferred.
• Heat is carried out when the coated article is exposed to high temperatures. The five cure temperatures will vary depending on the particular compounds employed in the composition, however they generally vary between 20 ° C and about 180 ° C, and preferably between about 50 ° C and about 120 ° C. The healing time will vary depending on the particular components used, and the physical parameters such
• 10 as thickness of the coating layers employed, however, typical cure times range from about 0.5 to about 30 minutes. The present invention is illustrated by the following non-limiting examples. 15 EXAMPLE 1
• A coating formulation having the composition shown in Table 1 is prepared by adding the latex emulsion to a stainless steel container. The adipic acid dihydrazide is housed in the container with continuous stirring for one hour to produce "Part A". Water, defoamer and thickeners are added to a mixture of a wetting agent and a stabilizer (diaminosilane). Later,
•• - "'• t t" "" - "" - * - * & * '* - * • ". - * t' *." * 'A portion (approximately 20%) of Part A is added under agitation. Next, TiO2 and Kaolin are added. After stirring for approximately 30 minutes, the remainder of Part A is added slowly with
• continuous agitation for 15 minutes. Subsequently, a mixture of epoxysilane and water is slowly added, followed by the surfactant solution. Viscosity is adjusted by adding additional thickener, if needed and adding ink. The resulting composition does not contain isocyanate or formaldehyde and is useful as an outer primer. 10 COMPARATIVE EXAMPLE
A coating composition was prepared with the formulation shown in Table 1 except that adipic acid dihydrazide, diaminosilane or epoxysilane were not included.
J_úü4naMÉtA¿lliUí littMHtkÜ iatttáitáfÉMiiiriiáHriiilitf MiiÉMláárita TABLE 1
Ingredient Quantity (kilograms) Part A XU41188.51 * 160.77 (40-55% emulsion of a styrene / carboxylated acrylate polymer in water) adipic acid dihydrazide 2.20 Part B Wetting agent 3.93 Hydrosil 2776 (diaminosilane) ** 1.02 Water 53.30 Defoamer 0.83 2% solution of Bentona LT 37.69 (thickener) TiO2 of rutile 20.11 Kaolin 200.79 DYNASYLAN® GLYMO (epoxysilane) ** 3.95 Water 10.42 Water 3.69 Surfactant solution *** 11.32 2% solution of Bentona LT 11.30 ( thickener) Black ink 2.44 Yellow ink 3.59
* Available from The Dow Chemical Company, Midland, Michigan ** Available from Hüls America, Inc., Somerset, N.J. *** SURFYNOL 104 PA (3.85 kg) plus 16.46 kg. deionized water.
COMPARATIVE EXAMPLE B
A coating composition having the formula shown in Table 1 was prepared except that 1% of a conventional 5 interleaver (isopropanolamine) was replaced by the adipic acid dihydrazide, diaminosilane and epoxylysilane.
EXAMPLE 2
^ ßp 10 The physical properties of the coating composition of the example were analyzed as follows: The samples were prepared for analysis, when applying the coating to the fiber cement panels. 2.07 grams of the coating composition was applied to a conventional fiber cement panel of
15.2 cm x 15.2 cm to provide a coating with a thickness of approximately 1 thousand (0.0254 mm). The solvent resistance of the coating was evaluated by exposing the coating to methyl ethyl ketone ("MEK"). Specifically, a ball of cotton dipped in MEK was gently rubbed from one side to the other on the
coating immediately followed by drying and cooling. For reproducibility and consistency the test is performed on glass. When a break in the coating is observed, the double number of rubs with MEK is recorded again. If a coating has not failed after 200
? j ^^^^ J ^^^ i * í? jM ^ w¡ «F ^ ¡¡* gri ^ rubs with MEK, the test is finished and the results are reported as 200+ rubs. A double rub with MEK is when you pass only once from one side to the other with the ball of cotton immersed with MEK. • The water resistance of the coating is tested using a
"Cobb test" as described in ASTM # D5795-95, volume 6.01. A lower value indicates greater resistance to water. The Cobb test is performed only after they have been allowed to reach equilibrium to the samples, in this case approximately 5 days. The blocking resistance is analyzed as follows: ^ 10 Following the cooling procedure of the finishing system, three fiber cement panels are placed so that they are in front to front contact and in front to back contact. The panels are placed in a hydraulic press that has previously been heated to a temperature previously selected in the scale of
60 ° C-82 ° C depending on the severity of the test requirements of the finishing system. The pressure rises to 125 psi and is maintained for
, 15 minutes. Subsequently, the panels are checked for any fixation or obstruction. The failure rate is recorded. The abrasion resistance of the coating is analyzed at
place two fiber cement panels in a gardner debugging tester against the face. The upper panel is attached to a pulley on the gardner debugging tester and weighed with a weight of 2 kilograms. The scrubber tester is turned on and the uncoated surface of the top panel is
g ^ s «HMMTMÉH iittifateÜijM MüiM h ^ .- í ^ glides from one side to the other, eroding the painted surface of the lower panel. Each step, from one side to another, is considered a cycle. When a tearing of the paint occurs, the number of cycles is recorded. For purposes of
• comparison, the coatings of the comparative examples A and B are also analyzed. The results are given in table II.
• 10
As demonstrated by the above data, the coating according to the description herein, shows better solvent resistance, water resistance, blocking resistance and resistance to
abrasion compared to the comparative examples. Although the above description contains many specific details of compositions and methods, these specific details should not be considered as limitations
• in the scope of any of the described inventions, but as exemplifications of the preferred modalities thereof. The experts in
The technique foresees possible variations that are within the scope and spirit of the inventions as defined in the appended claims.
Claims (25)
- NOVELTY OF THE INVENTION CLAIMS • 5 1. A coating composition characterized in that it comprises: a polymer having at least one reactive group and at least one hydrazide group thereof; and a silane.
- 2. The coating composition according to claim 1, further characterized in that the polymer is selected from • Starting from the group consisting of acrylic polymers, modified acrylic polymers, polyepoxides, polyesters, polyurethanes, polyamides, polyimides, polysiloxanes, polycarbonates and mixtures thereof.
- 3. The coating composition according to claim 1, further characterized in that at least one reactive group is 15 selected from the group consisting of carboxyl, hydroxyl, epoxy, amino and amido groups.
- 4. The coating composition according to claim 1, further characterized in that the silane is a compound of the formula: ^^^ | »^^^« ^ y ^ | gj ^ g ^ ¡^^ | where n = 1 to 100; R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms; R is the same or different in each case and is a portion selected from the group consisting of groups • halogen, hydrogen, alkoxy, hydroxy, amino and epoxy; and R2 may be the same or different in each situation and is selected from the group consisting of R and R1 as defined above.
- 5. The coating composition according to claim 4, further characterized in that R1 in the silane formula is selected from the group consisting of amino and epoxy groups.
- 6. The coating composition according to claim 1, further characterized in that it comprises a solvent.
- 7. The coating composition according to claim 1, further characterized in that the solvent is water.
- 8. The coating composition in accordance with the 15 claim 1, further characterized in that it substantially does not contain socianate or formaldehyde.
- 9. A method for coating characterized in that it comprises: providing a composition containing a polymer and a silane, the polymer having at least one reactive group and at least one hydrazide group in the 20 same; and apply the composition to a substrate.
- 10. The method according to claim 9, further characterized in that the polymer is selected from the group consisting of acrylic polymers, modified acrylic polymers, polyepoxides, polyesters, polyurethanes, polyamides, polmides, polysiloxanes, polycarbonates * and mixtures thereof.
- 11. The method according to claim 9, further characterized in that at least one reactive group is selected from the group consisting of carboxyl, hydroxyl, epoxy, amino, and amido groups.
- 12. The method according to claim 9, further characterized in that the silane is a compound of the formula: where n = 1 to 1000; R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms; Ri is the same or different in each case and is a portion selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and R2 may be the same or different in each case and is selected from the group consisting of R and jf R-i as defined above.
- 13. The method according to claim 12, further characterized in that Ri in the silane formula is selected from the group consisting of amino and epoxy groups.
- 14. The method according to claim 9, further characterized in that the composition contains a solvent and also 1. ..... J. .-AA ^ A. ... .- .. i. némtrjl ».« .. »« * .... * - -. • ** > «. .. * - ». * > . ! . . , WiiiáBft comprises the step of removing the solvent from the composition after application to the substrate.
- 15. The method according to claim 9, further characterized in that the solvent is water.
- 16. The method according to claim 9, further characterized in that the composition does not contain substantially isocyanate or formaldehyde.
- 17. The method for preparing a coating composition comprising: (a) reacting a polymer having at least one reactive group with a compound having a hydrazide group; and (b) combining the product of step (a) with a silane.
- 18. The method according to claim 17, further characterized in that the polymer is selected from the group consisting of acrylic polymers, modified acrylic polymers, polyepoxides, polyesters, polyurethanes, polyamides, polyimides, polysiloxanes, polycarbonates and mixtures thereof. same.
- 19. The method according to claim 17, further characterized in that at least one reactive group is selected from the group consisting of carboxyl, hydroxyl, epoxy, amino, and amido groups.
- 20. The method according to claim 17, further characterized in that the silane is a compound of the formula: wherein n = 1 to 1000; R is an optionally substituted hydrocarbon group containing from 1 to 20 carbon atoms; Ri is the same or different in each case and is a portion selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and R2 may be the same or different in each case and is selected from the group consisting of R and Ri as defined above.
- 21. The method according to claim 20, further characterized in that R-i in the silane formula is selected from the group consisting of amino and epoxy groups.
- 22. The method according to claim 17, further characterized in that step (a) is carried out in the presence of a solvent.
- 23. The method according to claim 22, further characterized in that the solvent is water.
- 24. The method according to claim 17, further characterized in that the compound having a hydrazide group is selected from the group consisting of polyhydrazide compounds.
- 25. The method according to claim 17, further characterized in that the compound having a hydrazide group is adipic acid dihydrazide. ¡¡¡¡¡¡¡¡¡¡¡¡¡! 26. - A coating comprising a polymer interlaced by means of a silane, the polymer having at least one tive group and at least one hydrazide group therein. • 27.- The coating according to claim 26, 5 further characterized in that the polymer is selected from the group consisting of acrylic polymers, modified acrylic polymers, polyepoxides, polyesters, polyurethanes, polyamides, polyimides, polysiloxanes, polycarbonates and mixtures thereof. 28.- The coating according to claim 26, • 10 further characterized in that at least one tive group is selected from the group consisting of carboxyl, hydroxyl, epoxy, amino, and amido groups. 29. The coating according to claim 26, further characterized in that the silane is a compound of the formula: where n = 1 to 1000; R is an optionally substituted hydrocarbon group 20 containing from 1 to 20 carbon atoms; Ri is the same or different in each case and is a portion selected from the group consisting of halogen, hydrogen, alkoxy, hydroxy, amino and epoxy groups; and R2 can be the same or different in each case and is selected from the group consisting of R and Ri as defined above. 30. The coating according to claim 29, further characterized in that Ri in the silane formula is selected from the group consisting of amino and epoxy groups. • * - * - * • «- ^ ¡¡^ - ^ Mfa ** J-
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US09198041 | 1998-11-23 |
Publications (1)
Publication Number | Publication Date |
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MXPA01005189A true MXPA01005189A (en) | 2002-05-09 |
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