JP5743549B2 - 湿気硬化型シリル化ポリウレアならびにそれを含有する接着剤、封止剤およびコート剤組成物 - Google Patents
湿気硬化型シリル化ポリウレアならびにそれを含有する接着剤、封止剤およびコート剤組成物 Download PDFInfo
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- JP5743549B2 JP5743549B2 JP2010540667A JP2010540667A JP5743549B2 JP 5743549 B2 JP5743549 B2 JP 5743549B2 JP 2010540667 A JP2010540667 A JP 2010540667A JP 2010540667 A JP2010540667 A JP 2010540667A JP 5743549 B2 JP5743549 B2 JP 5743549B2
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- Japan
- Prior art keywords
- isocyanate
- polyurea
- silylated
- amine
- moisture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920002396 Polyurea Polymers 0.000 title claims abstract description 220
- 239000000565 sealant Substances 0.000 title description 22
- 239000000853 adhesive Substances 0.000 title description 18
- 230000001070 adhesive effect Effects 0.000 title description 17
- 239000008199 coating composition Substances 0.000 title 1
- 229920000768 polyamine Polymers 0.000 claims abstract description 66
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 48
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 239000004202 carbamide Substances 0.000 claims abstract description 34
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 33
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229910000077 silane Inorganic materials 0.000 claims abstract description 33
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012948 isocyanate Substances 0.000 claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 70
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 46
- -1 acryloxy functionality Chemical group 0.000 claims description 35
- 238000006884 silylation reaction Methods 0.000 claims description 35
- 150000004985 diamines Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 17
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 claims description 16
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 claims description 15
- 150000004756 silanes Chemical class 0.000 claims description 10
- 238000013008 moisture curing Methods 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 7
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- IHZHYITXFSSZIZ-UHFFFAOYSA-N 2-isocyanatoethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCN=C=O IHZHYITXFSSZIZ-UHFFFAOYSA-N 0.000 claims description 4
- NUAJUIIWLHBKPD-UHFFFAOYSA-N 4-isocyanatobutylsilane Chemical compound [SiH3]CCCCN=C=O NUAJUIIWLHBKPD-UHFFFAOYSA-N 0.000 claims description 4
- DYLRLWGHBDMWAM-UHFFFAOYSA-N 7-isocyanatoheptan-2-yl(dimethoxy)silane Chemical compound CC(CCCCCN=C=O)[SiH](OC)OC DYLRLWGHBDMWAM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Chemical group 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- AQXPJYFPHOGPBW-UHFFFAOYSA-N 4-isocyanatobutan-2-yl(dimethoxy)silane Chemical compound CC(CCN=C=O)[SiH](OC)OC AQXPJYFPHOGPBW-UHFFFAOYSA-N 0.000 claims description 3
- MHXUIXGLOQTQBT-UHFFFAOYSA-N 5-isocyanatopentylsilane Chemical compound [SiH3]CCCCCN=C=O MHXUIXGLOQTQBT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 claims description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 3
- POZSTGZKLIJTEG-UHFFFAOYSA-N (1-dimethylsilyl-3-isocyanatopropyl) trimethyl silicate Chemical compound CO[Si](OC(CCN=C=O)[SiH](C)C)(OC)OC POZSTGZKLIJTEG-UHFFFAOYSA-N 0.000 claims description 2
- YVYGDINHTVKXEY-UHFFFAOYSA-N 1-isocyanatobutan-2-yl(dimethoxy)silane Chemical compound C(C)C(CN=C=O)[SiH](OC)OC YVYGDINHTVKXEY-UHFFFAOYSA-N 0.000 claims description 2
- JVVDURMXZZATIC-UHFFFAOYSA-N 1-isocyanatopentan-3-yl(dimethoxy)silane Chemical compound C(C)C(CCN=C=O)[SiH](OC)OC JVVDURMXZZATIC-UHFFFAOYSA-N 0.000 claims description 2
- LKSVDBOSJYQVTG-UHFFFAOYSA-N 1-isocyanatopropan-2-yl(dimethoxy)silane Chemical compound CC(CN=C=O)[SiH](OC)OC LKSVDBOSJYQVTG-UHFFFAOYSA-N 0.000 claims description 2
- DMZPTAFGSRVFIA-UHFFFAOYSA-N 3-[tris(2-methoxyethoxy)silyl]propyl 2-methylprop-2-enoate Chemical compound COCCO[Si](OCCOC)(OCCOC)CCCOC(=O)C(C)=C DMZPTAFGSRVFIA-UHFFFAOYSA-N 0.000 claims description 2
- JMGZKPMMFXFSGK-UHFFFAOYSA-N 3-tri(propan-2-yloxy)silylpropyl prop-2-enoate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCOC(=O)C=C JMGZKPMMFXFSGK-UHFFFAOYSA-N 0.000 claims description 2
- LEPRPXBFZRAOGU-UHFFFAOYSA-N 3-trichlorosilylpropyl prop-2-enoate Chemical compound Cl[Si](Cl)(Cl)CCCOC(=O)C=C LEPRPXBFZRAOGU-UHFFFAOYSA-N 0.000 claims description 2
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 claims description 2
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 claims description 2
- DSBLXLMAHMQMPF-UHFFFAOYSA-N 5-isocyanatopentan-2-yl(dimethoxy)silane Chemical compound CC(CCCN=C=O)[SiH](OC)OC DSBLXLMAHMQMPF-UHFFFAOYSA-N 0.000 claims description 2
- OWBNPAWCKWLFGD-UHFFFAOYSA-N 6-isocyanatohexan-2-yl(dimethoxy)silane Chemical compound CC(CCCCN=C=O)[SiH](OC)OC OWBNPAWCKWLFGD-UHFFFAOYSA-N 0.000 claims description 2
- HUHGKBBIOFENOY-UHFFFAOYSA-N 6-isocyanatohexyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCCCN=C=O HUHGKBBIOFENOY-UHFFFAOYSA-N 0.000 claims description 2
- MRXBJADWUUTZAQ-UHFFFAOYSA-N CC(CN=C=O)[SiH](OCC)OCC Chemical compound CC(CN=C=O)[SiH](OCC)OCC MRXBJADWUUTZAQ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000459 Nitrile rubber Polymers 0.000 claims description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims description 2
- AIWDGNXFJLIJLT-UHFFFAOYSA-N diethoxy(1-isocyanatobutan-2-yl)silane Chemical compound C(C)C(CN=C=O)[SiH](OCC)OCC AIWDGNXFJLIJLT-UHFFFAOYSA-N 0.000 claims description 2
- JQAMIOLMMWZSBT-UHFFFAOYSA-N diethoxy(1-isocyanatopentan-3-yl)silane Chemical compound C(C)C(CCN=C=O)[SiH](OCC)OCC JQAMIOLMMWZSBT-UHFFFAOYSA-N 0.000 claims description 2
- RFIBUQFQVPJGKA-UHFFFAOYSA-N diethoxy(1-isocyanatopropyl)silane Chemical compound C(C)C([SiH](OCC)OCC)N=C=O RFIBUQFQVPJGKA-UHFFFAOYSA-N 0.000 claims description 2
- NREIIZQALXLAIU-UHFFFAOYSA-N diethoxy(4-isocyanatobutan-2-yl)silane Chemical compound CC(CCN=C=O)[SiH](OCC)OCC NREIIZQALXLAIU-UHFFFAOYSA-N 0.000 claims description 2
- ZHLJTGUNBNEEGV-UHFFFAOYSA-N diethoxy(6-isocyanatohexan-2-yl)silane Chemical compound CC(CCCCN=C=O)[SiH](OCC)OCC ZHLJTGUNBNEEGV-UHFFFAOYSA-N 0.000 claims description 2
- GUYKYYCBJAXIQT-UHFFFAOYSA-N diethoxy(7-isocyanatoheptan-3-yl)silane Chemical compound C(C)C(CCCCN=C=O)[SiH](OCC)OCC GUYKYYCBJAXIQT-UHFFFAOYSA-N 0.000 claims description 2
- YQCRCWPAMZCIGJ-UHFFFAOYSA-N diethoxy(8-isocyanatooctan-3-yl)silane Chemical compound C(C)C(CCCCCN=C=O)[SiH](OCC)OCC YQCRCWPAMZCIGJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 claims description 2
- 239000000806 elastomer Substances 0.000 claims description 2
- QRFPECUQGPJPMV-UHFFFAOYSA-N isocyanatomethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CN=C=O QRFPECUQGPJPMV-UHFFFAOYSA-N 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- MOVRCMBPGBESLI-UHFFFAOYSA-N prop-2-enoyloxysilicon Chemical compound [Si]OC(=O)C=C MOVRCMBPGBESLI-UHFFFAOYSA-N 0.000 claims description 2
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 claims description 2
- IWQBIRQQKBICKW-UHFFFAOYSA-N triethoxy(5-isocyanatopentyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCN=C=O IWQBIRQQKBICKW-UHFFFAOYSA-N 0.000 claims description 2
- QKJDKLUGDDTSNP-UHFFFAOYSA-N triethoxy(6-isocyanatohexyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCN=C=O QKJDKLUGDDTSNP-UHFFFAOYSA-N 0.000 claims description 2
- BOTMPGMIDPRZGP-UHFFFAOYSA-N triethoxy(isocyanatomethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN=C=O BOTMPGMIDPRZGP-UHFFFAOYSA-N 0.000 claims description 2
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 2
- MBOOMFWIUMKSNA-UHFFFAOYSA-N isocyanatomethylsilane Chemical compound [SiH3]CN=C=O MBOOMFWIUMKSNA-UHFFFAOYSA-N 0.000 claims 3
- SZMZIUKGERWEQD-UHFFFAOYSA-N 1-isocyanatopropyl(trimethoxy)silane Chemical compound O=C=NC(CC)[Si](OC)(OC)OC SZMZIUKGERWEQD-UHFFFAOYSA-N 0.000 claims 1
- AONXMESMHBIONB-UHFFFAOYSA-N 4-isocyanatobutyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCN=C=O AONXMESMHBIONB-UHFFFAOYSA-N 0.000 claims 1
- VZLHAKDPXIPRFW-UHFFFAOYSA-N 6-isocyanatohexan-3-yl(dimethoxy)silane Chemical compound C(C)C(CCCN=C=O)[SiH](OC)OC VZLHAKDPXIPRFW-UHFFFAOYSA-N 0.000 claims 1
- TWXOYZZHTUAXGV-UHFFFAOYSA-N 8-isocyanatooctan-3-yl(dimethoxy)silane Chemical compound C(C)C(CCCCCN=C=O)[SiH](OC)OC TWXOYZZHTUAXGV-UHFFFAOYSA-N 0.000 claims 1
- DOQULPQNFSXMAX-UHFFFAOYSA-N CC(CCCN=C=O)[SiH](OCC)OCC Chemical compound CC(CCCN=C=O)[SiH](OCC)OCC DOQULPQNFSXMAX-UHFFFAOYSA-N 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- ANJPRQPHZGHVQB-UHFFFAOYSA-N hexyl isocyanate Chemical compound CCCCCCN=C=O ANJPRQPHZGHVQB-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 42
- 150000002513 isocyanates Chemical class 0.000 abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 238000003756 stirring Methods 0.000 description 50
- 239000000523 sample Substances 0.000 description 45
- 239000010408 film Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 25
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 21
- 239000005058 Isophorone diisocyanate Substances 0.000 description 20
- 238000004448 titration Methods 0.000 description 18
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 17
- 238000010561 standard procedure Methods 0.000 description 17
- 238000001514 detection method Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- 239000008096 xylene Substances 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 13
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 13
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 13
- 229910000080 stannane Inorganic materials 0.000 description 13
- 238000002156 mixing Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000007605 air drying Methods 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 11
- 229920002799 BoPET Polymers 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 239000004970 Chain extender Substances 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 150000003335 secondary amines Chemical group 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000004696 Poly ether ether ketone Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 229920002530 polyetherether ketone Polymers 0.000 description 4
- 239000011253 protective coating Substances 0.000 description 4
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FRDNYWXDODPUJV-UHFFFAOYSA-N n-ethyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CCNCC(C)C[Si](OC)(OC)OC FRDNYWXDODPUJV-UHFFFAOYSA-N 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 3
- 239000004432 silane-modified polyurethane Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 229920013646 Hycar Polymers 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000010960 cold rolled steel Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
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- 239000000975 dye Substances 0.000 description 1
- 229910052876 emerald Inorganic materials 0.000 description 1
- 239000010976 emerald Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-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
- YSLVSGVAVRTLAV-UHFFFAOYSA-N ethyl(dimethoxy)silane Chemical compound CC[SiH](OC)OC YSLVSGVAVRTLAV-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-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
- SMIDUPHNWFRONB-UHFFFAOYSA-N n,2-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCC(C)C[Si](OC)(OC)OC SMIDUPHNWFRONB-UHFFFAOYSA-N 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- KGNDVXPHQJMHLX-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)cyclohexanamine Chemical compound CO[Si](OC)(OC)CCCNC1CCCCC1 KGNDVXPHQJMHLX-UHFFFAOYSA-N 0.000 description 1
- SWPRLROHVKTMPN-UHFFFAOYSA-N n-butyl-2-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CCCCNCC(C)C[Si](OC)(OC)OC SWPRLROHVKTMPN-UHFFFAOYSA-N 0.000 description 1
- YJOGKUUQSLYPQJ-UHFFFAOYSA-N n-ethyl-2,2-dimethyl-4-trimethoxysilylbutan-1-amine Chemical compound CCNCC(C)(C)CC[Si](OC)(OC)OC YJOGKUUQSLYPQJ-UHFFFAOYSA-N 0.000 description 1
- AXTLFVLHXSDZOW-UHFFFAOYSA-N n-ethyl-2-methylprop-2-en-1-amine Chemical compound CCNCC(C)=C AXTLFVLHXSDZOW-UHFFFAOYSA-N 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- OKIKLSJWTXOVSF-UHFFFAOYSA-N n-methyl-2-(3-trimethoxysilylpropoxy)propan-1-amine Chemical compound CNCC(C)OCCC[Si](OC)(OC)OC OKIKLSJWTXOVSF-UHFFFAOYSA-N 0.000 description 1
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- LFVRJTOLPGFXHU-UHFFFAOYSA-N o-(1h-imidazol-2-yl)hydroxylamine Chemical compound NOC1=NC=CN1 LFVRJTOLPGFXHU-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 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
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- YJGJRYWNNHUESM-UHFFFAOYSA-J triacetyloxystannyl acetate Chemical compound [Sn+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O YJGJRYWNNHUESM-UHFFFAOYSA-J 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
- DSROZUMNVRXZNO-UHFFFAOYSA-K tris[(1-naphthalen-1-yl-3-phenylnaphthalen-2-yl)oxy]alumane Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2)C=1O[Al](OC=1C(=C2C=CC=CC2=CC=1C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)OC(C(=C1C=CC=CC1=C1)C=2C3=CC=CC=C3C=CC=2)=C1C1=CC=CC=C1 DSROZUMNVRXZNO-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/289—Compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/6262—Polymers of nitriles derived from alpha-beta ethylenically unsaturated carboxylic acids
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/40—Compositions for pressure-sensitive adhesives
-
- 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
- C08G2190/00—Compositions for sealing or packing joints
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
Description
Q−R1−SiXaY3−a
によって表わされるものであり、ここで、Qは、例えば、イソシアナト、エポキシ、もしくは(メタ)アクリロイル官能性のようなアミン反応性官能性であり、R1は、例えば、12個までの炭素原子の、任意選択で一つもしくはそれ以上のヘテロ原子を含むアルキレン基のような二価の架橋基であり、それぞれのXは、独立して、水素もしくは12個までの炭素原子のヒドロカルビルであり、それぞれのYは独立して、20個までの炭素原子のアルコキシ、20個までの炭素原子を含むカルビルオキシ、フェノキシ、ハロゲン、アミン、アミノキシ、イミダゾール、アセトンオキシ、アセトアミド、ベンズアミドもしくはケトオキシムであり、そして、aは、0、1もしくは2である。一実施態様において、R1は1から4個の炭素原子のアルキレンであり、それぞれのXはもし存在するなら1から4個の炭素原子のアルキルであり、そしてそれぞれのYは1から4個の炭素原子のアルコキシである。
HZ−R1−SiXaY3−a
によって表わされるようなものであり、ここでR1、X、Yおよびaは上述の意味を持ち、Zは硫黄、−NHもしくは−NR2であり、ここでR2は18個までの炭素原子のヒドロカルビルであるか、または−R1SiXaY3−aであり、ここでR1、X、Yおよびaは独立して上述の意味の一つを持つか、または−NR3−C(=O)−NR4−であり、ここで、R3およびR4はそれぞれ独立して水素もしくは18個までの炭素原子のヒドロカルビルである。これらのシランの中で、Zが硫黄もしくは−NR2−であり、ここでR2が8個までの炭素原子のヒドロカルビルであり、それぞれのXが独立して1から4個の炭素原子のアルキルであり、そしてそれぞれのYが独立して1から4個の炭素原子のアルコキシであるものが好ましい。
によって表わされ、ここでそれぞれのR5は独立して、Hもしくは一価の気であり、R6は価数mの有機基であるか、または、R5およびR6ならびに/または二つのR5基が一緒に結合し、環を形成し、そしてmは2から5、好ましくは2もしくは3であり、そしてより好ましくは2であり、ポリアミン(c)中に、有意な数のウレタン架橋もしくはヒドロキシル基はまったく存在しない。ポリアミンと2と等しいかもしくはそれより大きい平均値のmの混合物は、増加する粘着力のゆおうな湿気硬化型樹脂中において特定の性質を達成するために用いられ得る。
によって表わされ、ここでR7は、例えば、24個までの炭素原子の炭化水素残基、またはウレタン架橋を有意に持たないポリマー鎖のような価数nの多価の有機基、そしてnは2から5、好ましくは2もしくは3、そしてより好ましくは2である。
〔式中、それぞれのR5が同一のもしくは異なる一価の基、例えば、メチル、エチルなどであり、そしてR6が、モノマー、オリゴマーもしくはポリマー構造の二価の有機基である〕
のモル過剰の二級ジアミンで、例えばp+1モルで、pが1もしくは2であるものが、pモルの一般式:
OCN−R7−NCO
〔式中、R7はモノマー、オリゴマーもしくはポリマー構造の二価の有機基である〕
のジイソシアナートと反応するとき、生じる二級アミン末端ポリウレア(b)(1)は一般式I:
によって表わされるであろう。
OCN−R1−SiXaY3−a
〔式中、R1、X、Yは上述の意味を持つ〕
のイソシアナトシランによるシリル化において、生じる本発明の範囲に入る湿気硬化型シリル化ポリウレアは一般式II:
によって表わされ得る。
〔式中、R1、R2、X、Yは上述の意味を持つ〕
の二級アミノシランによるシリル化において、生じる本発明の範囲に入る湿気硬化型シリル化ポリウレアは一般式IV:
によって表わされ得る。
この実施例は、本発明によるシリル化ポリウレアをもたらす、二級アミン末端ポリウレアプレポリマー(98当量%のウレア架橋)のイソシアナトシランによるシリル化、およびそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす一級アミン末端ポリウレアプレポリマー(98当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびにそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす二級アミン末端ポリウレアプレポリマー(99当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびに金属と金属の結合操作に用いるためのそれを含む付着接触剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらすイソシアナト末端ポリウレアプレポリマー(98当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびにそれを含む保護コート剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす一級アミン末端ポリウレアプレポリマー(100当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびにそれを含む保護コート剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらすイソシアナト末端ポリウレアプレポリマー(98当量%ウレア架橋)の二級アミノシランによるシリル化、ならびにそれを含む下塗り剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす一級アミン末端ポリウレアプレポリマー(97当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびにそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす一級アミン末端ポリウレアプレポリマー(97当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびにそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす一級アミン末端ポリウレアプレポリマー(97当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびにそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす二級アミン末端ポリウレアプレポリマー(100当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびにそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、実施例10のシリル化ポリウレアを含み、粘着付与剤を含む接着剤組成物を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらすイソシアナト末端ポリウレアプレポリマー(98当量%ウレア架橋)の二級アミノシランによるシリル化、ならびにそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす二級アミン末端ポリウレアプレポリマー(98当量%ウレア架橋)のエポキシシランによるシリル化、ならびにそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす二級アミン末端ポリウレアプレポリマー(98当量%ウレア架橋)のメタクリロキシシランによるシリル化、ならびにそれを含む感圧接着剤組成物の調製を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす二級アミン末端ポリウレアプレポリマー(100当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびに封止剤組成物へのシリル化ポリウレアの混合を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす二級アミン末端ポリウレアプレポリマー(100当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびに封止剤組成物へのシリル化ポリウレアの混合を説明する。
この実施例は、本発明のシリル化ポリウレアをもたらす二級ジアミンおよび一級トリアミンの混合物より得られるアミン末端ポリウレアプレポリマー(100当量%ウレア架橋)のイソシアナトシランによるシリル化、ならびに封止剤組成物へのシリル化ポリウレアの混合を説明する。
この比較例は、既知の型の湿気硬化型シリル化ポリウレタン樹脂(「SPUR」樹脂;100当量パーセントのウレタン架橋)の調製と、それを含む封止剤組成粒とを説明し、上述の実施例16に説明されるような本発明のシリル化ポリウレアおよび封止剤組成物との比較の目的で提供される。
比較例2は、本発明の範囲外である米国特許出願公開2007/0129527A1に開示されるシリル化ポリウレタン−ポリウレア(58当量パーセントのウレア架橋、42当量パーセントのウレタン架橋)の調製と、それを含む封止剤組成物とを説明する。
Claims (13)
- 湿気硬化型の、任意選択で硬化したシリル化ポリウレアもしくはそれらの混合物であって、加水分解性官能性を持つ少なくとも一つのオルガノ官能性シラン(a)と少なくとも一つのアミン末端もしくはイソシアナト末端ポリウレア(b)との反応産物を含有し、ここでポリウレア(b)は少なくとも一つのポリアミン(c)と少なくとも一つのポリイソシアナート(d)とのオルガノ官能性シラン(a)の実質的に非存在下における反応によって得られ、前記湿気硬化型シリル化ポリウレアは、その中に、ウレアとウレタンの架橋の総当量に基づいて平均で80から100当量パーセントのウレアの架橋を持ち、
ここで、ポリウレア(b)がアミン末端ポリウレア(b)(1)であり、オルガノ官能性シラン(a)が一般式:
Q−R1−SiXaY3−a
〔式中、Qはアミン反応性官能性であり、R1は二価の架橋基であり、それぞれのXは、独立して、水素もしくは12個までの炭素原子のヒドロカルビルであり、それぞれのYは独立して、同一かもしくは異なる加水分解性基であり、そして、aは、0、1もしくは2である。〕のアミン反応性シラン(a)(1)である、
湿気硬化型の、任意選択で硬化したシリル化ポリウレア。 - 少なくとも90当量パーセントのウレア架橋を持つ、請求項1に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- ポリウレア(b)が1重量パーセント以下の非反応のポリアミン(c)および/もしくは10重量パーセントの以下のオリゴマーを持つアミン末端ポリウレア(b)(1)である、請求項1〜2のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- ポリウレア(b)が2から5のアミン基を持つポリアミン(c)からと、2から5のイソシアナト基を持つポリイソシアナート(d)から誘導される、請求項1〜3のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- ポリウレア(b)が2から3のアミン基を持つポリアミン(c)からと、2から3のイソシアナト基を持つポリイソシアナート(d)から誘導される、請求項1〜3のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- Qがイソシアナト、エポキシもしくは(メタ)アクリロキシ官能性である、請求項1〜5のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- R1が1から4個の炭素原子のアルキレンであり、それぞれのXが独立して1から4個の炭素原子のアルキルであり、そしてそれぞれのYが独立して1から4個の炭素原子のアルコキシである、請求項1〜6のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- アミノ反応性シラン(a)(1)が、メチルジメトキシシリルメチルイソシアナート、トリメトキシシリルメチルイソシアナート、ジエチルメトキシシリルメチルイソシアナート、エチルジメトキシシリルメチルイソシアナート、メチルジエトキシシリルメチルイソシアナート、トリエトキシシリルメチルイソシアナート、エチルジエトキシシリルメチルイソシアナート、メチルジメトキシシリルエチルイソシアナート、トリメトキシシリルエチルイソシアナート、エチルジメトキシシリルエチルイソシアナート、メチルジエトキシシリルエチルイソシアナート、トリメトキシシリルエチルイソシアナート、エチルジエトキシシリルエチルイソシアナート、メチルジメトキシシリルプロピルイソシアナート、トリメトキシシリルプロピルイソシアナート、エチルジメトキシシリルプロピルイソシアナート、メチルジエトキシシリルプロピルイソシアナート、トリエトキシシリルプロピルイソシアナート、エチルジエトキシシリルプロピルイソシアナート、メチルジメトキシシリルプロピルイソシアナート、メチルジメトキシシリルブチルイソシアナート、トリメトキシシリルブチルイソシアナート、エチルジメトキシシリルブチルイソシアナート、メチルジエトキシシリルブチルイソシアナート、トリメトキシシリルブチルイソシアナート、エチルジエトキシシリルブチルイソシアナート、メチルジメトキシシリルペンチルイソシアナート、トリメトキシシリルペンチルイソシアナート、エチルジメトキシシリルペンチルイソシアナート、メチルジエトキシシリルペンチルイソシアナート、トリエトキシシリルペンチルイソシアナート、エチルジエトキシシリルペンチルイソシアナート、メチルジメトキシシリルペンチルイソシアナート、メチルジメトキシシリルヘキシルイソシアナート、トリメトキシシリルヘキシルイソシアナート、エチルジメトキシシリルヘキシルイソシアナート、メチルジエトキシシリルヘキシルイソシアナート、トリエトキシシリルヘキシルイソシアナート、エチルジエトキシシリルヘキシルイソシアナート、メチルジメトキシシリルヘキシルイソシアナート、およびγ−トリメトキシシロキシジメチルシリルプロピルイソシアナートからなる群より選択される少なくとも一つのイソシアナトシラン(a)(1)(i);3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルメチルジエトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)−エチルトリエトキシシランからなる群より選択されるエポキシシラン(a)(1)(ii)ならびに/または3−アクリロキシプロピルトリメトキシシラン、3−アクリロキシプロピルトリエトキシシラン、3−アクリロキシプロピルトリイソプロポキシシラン、3−メタクリロキシプロピルトリメトキシシラン、3−メタクリロキシイソブチルトリメトキシシラン、3−アクリロキシプロピルトリクロロシラン、3−メタクリロキシイソブチルトリクロロシラン、3−メタクリロキシイソブチルトリクロロシラン、3−メタクリロキシプロピル[トリス(ベータ−メトキシエトキシ)]シランからなる群より選択される(メタ)アクリロキシシラン(a)(1)(iii)である、請求項1〜7のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- ポリウレア(b)がアミン末端ポリウレア(b)(1)もしくはそれらの混合物であり、その中に存在する少なくとも部分的から実質的にすべてまでのアミン基が二級アミン基である、請求項1〜8のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- ポリウレア(b)が、(1)モノマーポリアミン(c)とモノマーポリイソシアナート(d)との反応、または(2)モノマーポリアミン(c)と完全なプレポリマーのオリゴマーポリイソシアナートおよび/もしくはポリマーポリシアナート(d)との反応、または(3)オリゴマーおよび/もしくはポリマーポリアミン(c)とモノマーポリイソシアナート(d)との反応、または(4)オリゴマーおよび/もしくはポリマーポリアミン(c)と、完全なプレポリマーのオリゴマーポリイソシアナートおよび/もしくはポリマーポリイソシアナート(d)との反応から得られる、請求項1〜9のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- オリゴマーおよび/もしくはポリマージアミン(c)の骨格が、完全にもしくは主に、ポリエーテル、ポリエステル、ポリカーボナート、ポリアミド、ポリウレア、ポリブタジエン、ブタジエン−アクリロニトリルコポリマーまたはエラストマーである、請求項10に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- ポリウレア(b)のシリル化可能な基もしくはそれらの混合物が、単官能性のキャップ反応物によってキャップされている、請求項1〜11のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
- 前記シリル化ポリウレアが分岐を持っている、請求項1〜12のいずれか1項に記載の湿気硬化型の、任意選択で硬化したシリル化ポリウレア。
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DE10053545A1 (de) * | 2000-10-27 | 2002-05-08 | Henkel Kgaa | Polymere mit Harnstoffgruppen und Silylgruppen, deren Herstellung und Verwendung |
US6520186B2 (en) * | 2001-01-26 | 2003-02-18 | L'oreal | Reshapable hair styling composition comprising silicon-containing polycondensates |
US7001948B2 (en) * | 2001-05-16 | 2006-02-21 | American Polymer Corporation | Polyurea coating compositions |
DE10141235A1 (de) * | 2001-08-23 | 2003-03-27 | Consortium Elektrochem Ind | Feuchtigkeitsvernetzende elastische Zusammensetzung |
DE10201703A1 (de) * | 2002-01-17 | 2003-08-07 | Consortium Elektrochem Ind | Alkoxysilanterminierte Polymere enthaltende vernetzbare Polymerabmischungen |
DE10353663A1 (de) * | 2003-11-17 | 2005-06-16 | Henkel Kgaa | Polyurethanzusammensetzungen mit NCO- und Silylreaktivität |
US7211621B2 (en) * | 2004-02-11 | 2007-05-01 | E. I. Du Pont De Nemours And Company | Polyurethaneurea resins with trialkoxysilane groups and processes for the production thereof |
WO2006070637A1 (ja) * | 2004-12-28 | 2006-07-06 | Kaneka Corporation | 硬化性組成物 |
US20070129527A1 (en) * | 2005-12-06 | 2007-06-07 | Griswold Roy M | Silylated polyurethane-polyurea protective coating compositions |
-
2007
- 2007-12-26 US US12/005,233 patent/US8378037B2/en active Active
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2008
- 2008-12-24 EP EP08866981A patent/EP2231740B1/en active Active
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- 2008-12-24 WO PCT/US2008/014048 patent/WO2009085285A1/en active Application Filing
- 2008-12-24 JP JP2010540667A patent/JP5743549B2/ja active Active
- 2008-12-25 TW TW97150701A patent/TWI469998B/zh active
Also Published As
Publication number | Publication date |
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EP2231740A1 (en) | 2010-09-29 |
US8378037B2 (en) | 2013-02-19 |
JP2011508050A (ja) | 2011-03-10 |
ATE521653T1 (de) | 2011-09-15 |
US20090171040A1 (en) | 2009-07-02 |
WO2009085285A1 (en) | 2009-07-09 |
EP2231740B1 (en) | 2011-08-24 |
TWI469998B (zh) | 2015-01-21 |
TW200946550A (en) | 2009-11-16 |
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