TWI262205B - Room temperature curable functionalized HNBR coating - Google Patents

Info

Publication number

TWI262205B

TWI262205B TW092105121A TW92105121A TWI262205B TW I262205 B TWI262205 B TW I262205B TW 092105121 A TW092105121 A TW 092105121A TW 92105121 A TW92105121 A TW 92105121A TW I262205 B TWI262205 B TW I262205B

Authority

TW

Taiwan

Prior art keywords

group

film

coating

acid

coating composition

Prior art date

2002-03-08

Links

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• 238000000576 coating method Methods 0.000 title claims abstract description 184
• 239000011248 coating agent Substances 0.000 title claims abstract description 168
• 229920006168 hydrated nitrile rubber Polymers 0.000 title claims description 15
• 229920001971 elastomer Polymers 0.000 claims abstract description 190
• 229920000642 polymer Polymers 0.000 claims abstract description 162
• 239000000806 elastomer Substances 0.000 claims abstract description 103
• 125000000524 functional group Chemical group 0.000 claims abstract description 77
• 150000001875 compounds Chemical class 0.000 claims abstract description 72
• 229920001577 copolymer Polymers 0.000 claims abstract description 66
• 239000008199 coating composition Substances 0.000 claims abstract description 65
• 229910052751 metal Inorganic materials 0.000 claims abstract description 39
• 239000002184 metal Substances 0.000 claims abstract description 39
• 239000005056 polyisocyanate Substances 0.000 claims abstract description 34
• 229920001228 polyisocyanate Polymers 0.000 claims abstract description 34
• 239000007788 liquid Substances 0.000 claims abstract description 29
• -1 cyclic imine Chemical class 0.000 claims description 174
• 238000000034 method Methods 0.000 claims description 88
• 239000005060 rubber Substances 0.000 claims description 87
• 239000003795 chemical substances by application Substances 0.000 claims description 83
• 239000000178 monomer Substances 0.000 claims description 75
• 229920000459 Nitrile rubber Polymers 0.000 claims description 57
• 238000006243 chemical reaction Methods 0.000 claims description 57
• 239000002904 solvent Substances 0.000 claims description 56
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 54
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 51
• 239000000203 mixture Substances 0.000 claims description 51
• 239000002253 acid Substances 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
• 239000000463 material Substances 0.000 claims description 30
• 239000005977 Ethylene Substances 0.000 claims description 29
• 244000043261 Hevea brasiliensis Species 0.000 claims description 28
• 229920003052 natural elastomer Polymers 0.000 claims description 28
• 229920001194 natural rubber Polymers 0.000 claims description 28
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
• 239000002245 particle Substances 0.000 claims description 27
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 26
• 238000004132 cross linking Methods 0.000 claims description 24
• 238000006116 polymerization reaction Methods 0.000 claims description 24
• 150000002148 esters Chemical class 0.000 claims description 23
• 150000008064 anhydrides Chemical class 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 239000000049 pigment Substances 0.000 claims description 20
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 19
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
• 239000007789 gas Substances 0.000 claims description 18
• 150000002825 nitriles Chemical class 0.000 claims description 17
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
• 150000001336 alkenes Chemical class 0.000 claims description 15
• 229920002943 EPDM rubber Polymers 0.000 claims description 14
• 239000002923 metal particle Substances 0.000 claims description 14
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 239000001301 oxygen Substances 0.000 claims description 14
• 125000003277 amino group Chemical group 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 12
• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 12
• 229920002857 polybutadiene Polymers 0.000 claims description 12
• 229920002367 Polyisobutene Polymers 0.000 claims description 11
• 229920003244 diene elastomer Polymers 0.000 claims description 11
• 229920000181 Ethylene propylene rubber Polymers 0.000 claims description 10
• 239000007795 chemical reaction product Substances 0.000 claims description 10
• 125000003700 epoxy group Chemical group 0.000 claims description 10
• IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
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• 229920000098 polyolefin Polymers 0.000 claims description 9
• 229920001897 terpolymer Polymers 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
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• 150000003141 primary amines Chemical class 0.000 claims description 8
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• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• 238000005507 spraying Methods 0.000 claims description 6
• 239000003638 chemical reducing agent Substances 0.000 claims description 5
• 238000007254 oxidation reaction Methods 0.000 claims description 5
• 230000036961 partial effect Effects 0.000 claims description 5
• 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
• 229920003048 styrene butadiene rubber Polymers 0.000 claims description 5
• 239000004698 Polyethylene Substances 0.000 claims description 4
• 238000003618 dip coating Methods 0.000 claims description 4
• 125000004185 ester group Chemical group 0.000 claims description 4
• 229920000573 polyethylene Polymers 0.000 claims description 4
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• 239000004743 Polypropylene Substances 0.000 claims description 3
• 230000001680 brushing effect Effects 0.000 claims description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 229920001155 polypropylene Polymers 0.000 claims description 3
• 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims description 3
• 150000003440 styrenes Chemical class 0.000 claims description 3
• 150000003512 tertiary amines Chemical class 0.000 claims description 3
• VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical class CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 claims description 2
• XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 claims description 2
• LNDKRVOOYMEYTC-UHFFFAOYSA-N buta-1,3-dien-1-ol Chemical class OC=CC=C LNDKRVOOYMEYTC-UHFFFAOYSA-N 0.000 claims description 2
• MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 2
• XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 2
• 229920006007 hydrogenated polyisobutylene Polymers 0.000 claims description 2
• 239000007800 oxidant agent Substances 0.000 claims description 2
• 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 claims description 2
• 229920006132 styrene block copolymer Polymers 0.000 claims description 2
• 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
• 238000004227 thermal cracking Methods 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 2
• 150000002763 monocarboxylic acids Chemical class 0.000 claims 2
• 238000006385 ozonation reaction Methods 0.000 claims 2
• 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims 1
• 238000006356 dehydrogenation reaction Methods 0.000 claims 1
• 229920000554 ionomer Polymers 0.000 claims 1
• 229920003049 isoprene rubber Polymers 0.000 claims 1
• 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims 1
• 229920001084 poly(chloroprene) Polymers 0.000 claims 1
• 229920002755 poly(epichlorohydrin) Polymers 0.000 claims 1
• 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
• 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
• 150000003458 sulfonic acid derivatives Chemical class 0.000 claims 1
• 239000000758 substrate Substances 0.000 abstract description 81
• 150000001718 carbodiimides Chemical class 0.000 abstract description 14
• 230000017525 heat dissipation Effects 0.000 abstract description 12
• 239000006185 dispersion Substances 0.000 abstract description 10
• 230000007774 longterm Effects 0.000 abstract description 9
• 229920003180 amino resin Polymers 0.000 abstract 1
• 239000011231 conductive filler Substances 0.000 abstract 1
• 238000001723 curing Methods 0.000 description 80
• 239000012948 isocyanate Substances 0.000 description 56
• 150000002513 isocyanates Chemical class 0.000 description 51
• 150000001412 amines Chemical class 0.000 description 47
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 46
• 239000010408 film Substances 0.000 description 43
• 239000000243 solution Substances 0.000 description 37
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 33
• 238000005984 hydrogenation reaction Methods 0.000 description 30
• 150000003254 radicals Chemical class 0.000 description 30
• 125000004432 carbon atom Chemical group C* 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• 230000000694 effects Effects 0.000 description 28
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• 150000001993 dienes Chemical class 0.000 description 26
• 239000000126 substance Substances 0.000 description 26
• 239000007787 solid Substances 0.000 description 25
• 125000000217 alkyl group Chemical group 0.000 description 23
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 22
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 21
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 20
• LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 238000007306 functionalization reaction Methods 0.000 description 19
• 235000021419 vinegar Nutrition 0.000 description 19
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 18
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• 229910052782 aluminium Inorganic materials 0.000 description 18
• 239000000052 vinegar Substances 0.000 description 18
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 17
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 17
• 125000005442 diisocyanate group Chemical group 0.000 description 17
• 238000005649 metathesis reaction Methods 0.000 description 17
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• 125000005647 linker group Chemical group 0.000 description 6
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• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
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• OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
• 229920000089 Cyclic olefin copolymer Polymers 0.000 description 5
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