JP2018536040A - シリコーン樹脂で変性されたイソシアナトアルキルアルコキシシラン付加物およびその使用 - Google Patents
シリコーン樹脂で変性されたイソシアナトアルキルアルコキシシラン付加物およびその使用 Download PDFInfo
- Publication number
- JP2018536040A JP2018536040A JP2018516438A JP2018516438A JP2018536040A JP 2018536040 A JP2018536040 A JP 2018536040A JP 2018516438 A JP2018516438 A JP 2018516438A JP 2018516438 A JP2018516438 A JP 2018516438A JP 2018536040 A JP2018536040 A JP 2018536040A
- Authority
- JP
- Japan
- Prior art keywords
- group
- silicone resin
- binder
- alcohol
- acid
- 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.)
- Granted
Links
- 229920002050 silicone resin Polymers 0.000 title claims abstract description 64
- 239000011230 binding agent Substances 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 239000003973 paint Substances 0.000 claims abstract description 22
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000013466 adhesive and sealant Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- -1 neopentyl glycol hydroxypivalate Ester Chemical class 0.000 claims description 65
- 239000003054 catalyst Substances 0.000 claims description 47
- 239000011248 coating agent Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000005846 sugar alcohols Polymers 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000013522 chelant Substances 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- 239000002023 wood Substances 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- IHZHYITXFSSZIZ-UHFFFAOYSA-N 2-isocyanatoethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCN=C=O IHZHYITXFSSZIZ-UHFFFAOYSA-N 0.000 claims description 2
- CTRNPTLUEVNRNH-UHFFFAOYSA-N 2-isocyanatoethyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCN=C=O CTRNPTLUEVNRNH-UHFFFAOYSA-N 0.000 claims description 2
- JQKBYCKXGRPGAV-UHFFFAOYSA-N 3-isocyanatopropyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCN=C=O JQKBYCKXGRPGAV-UHFFFAOYSA-N 0.000 claims description 2
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 claims description 2
- FVMPSSZYZUMFDB-UHFFFAOYSA-N 4-isocyanatobutyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCCN=C=O FVMPSSZYZUMFDB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 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
- XGEGRZUCRFEEBL-UHFFFAOYSA-N isocyanatomethyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CN=C=O XGEGRZUCRFEEBL-UHFFFAOYSA-N 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 239000002923 metal particle Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- KEIBTGABMNALIT-UHFFFAOYSA-N triethoxy(2-isocyanatoethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCN=C=O KEIBTGABMNALIT-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
- ASUUSZXVXTVKDD-UHFFFAOYSA-N triethoxy(4-isocyanatobutyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCN=C=O ASUUSZXVXTVKDD-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
- UPLHJXJHPKZACQ-UHFFFAOYSA-N 1-tricyclo[5.2.1.02,6]decanylmethanol Chemical compound C12CCCC2C2(CO)CC1CC2 UPLHJXJHPKZACQ-UHFFFAOYSA-N 0.000 claims 1
- RBQLGIKHSXQZTB-UHFFFAOYSA-N 3-methylpentane-2,4-diol Chemical compound CC(O)C(C)C(C)O RBQLGIKHSXQZTB-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 2
- 229920001296 polysiloxane Polymers 0.000 description 23
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 22
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- CIFIGXMZHITUAZ-UHFFFAOYSA-M tetraethylazanium;benzoate Chemical compound CC[N+](CC)(CC)CC.[O-]C(=O)C1=CC=CC=C1 CIFIGXMZHITUAZ-UHFFFAOYSA-M 0.000 description 13
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 229920000058 polyacrylate Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229920004482 WACKER® Polymers 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
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- 239000004814 polyurethane Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- RECJVUVMDRZCPY-UHFFFAOYSA-N diethoxymethoxysilane Chemical compound C(C)OC(O[SiH3])OCC RECJVUVMDRZCPY-UHFFFAOYSA-N 0.000 description 5
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 description 5
- OTGKPTHUMQTAFJ-UHFFFAOYSA-N dipropoxymethoxysilane Chemical compound C(CC)OC(O[SiH3])OCCC OTGKPTHUMQTAFJ-UHFFFAOYSA-N 0.000 description 5
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 5
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
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- 150000001298 alcohols Chemical class 0.000 description 4
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- 125000005843 halogen group Chemical group 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- VJOOEHFQQLYDJI-UHFFFAOYSA-N methoxy(dimethyl)silane Chemical compound CO[SiH](C)C VJOOEHFQQLYDJI-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
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- 125000003944 tolyl group Chemical group 0.000 description 4
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-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
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- 238000009833 condensation Methods 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- WGYONVRJGWHMKV-UHFFFAOYSA-M tetrabutylazanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CCCC[N+](CCCC)(CCCC)CCCC WGYONVRJGWHMKV-UHFFFAOYSA-M 0.000 description 3
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- YRMWCMBQRGFNIZ-UHFFFAOYSA-N ethyl 3-oxobutanoate;zirconium Chemical compound [Zr].CCOC(=O)CC(C)=O YRMWCMBQRGFNIZ-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- YRXICXUINRGLJP-UHFFFAOYSA-N hydroxy(dimethyl)silicon Chemical compound C[Si](C)O YRXICXUINRGLJP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- MDLRQEHNDJOFQN-UHFFFAOYSA-N methoxy(dimethyl)silicon Chemical compound CO[Si](C)C MDLRQEHNDJOFQN-UHFFFAOYSA-N 0.000 description 1
- ZCDIMNQHVVPXIO-UHFFFAOYSA-N n'-benzyl-n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine;hydrochloride Chemical compound Cl.CO[Si](OC)(OC)CCCN(CCN)CC1=CC=CC=C1 ZCDIMNQHVVPXIO-UHFFFAOYSA-N 0.000 description 1
- TVIDDXQYHWJXFK-UHFFFAOYSA-N n-Dodecanedioic acid Natural products OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- YJBMMHPCGWCCOH-UHFFFAOYSA-N octan-3-yl dihydrogen phosphate Chemical compound CCCCCC(CC)OP(O)(O)=O YJBMMHPCGWCCOH-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006223 plastic coating Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001692 polycarbonate urethane Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- ROVPGYJWAOZLMR-UHFFFAOYSA-N propoxymethylsilane Chemical compound CCCOC[SiH3] ROVPGYJWAOZLMR-UHFFFAOYSA-N 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YOIAWAIKYVEKMF-UHFFFAOYSA-N trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F YOIAWAIKYVEKMF-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
Description
当業者は、先行技術からと、自身の専門知識の一部として、反応性NCO基の数を決定することができる方法を認識している。
R3 c(R4O)dR5 eSiO(4−c−d−e)/2 式(I)
[式中、
R3は、同じであるか、または異なっていてよく、かつ水素原子を意味するか、置換された、もしくは非置換のSiC結合した一価脂肪族炭化水素基を意味するか、または式(I)の2個の単位を橋かけする置換された、もしくは非置換の二価脂肪族炭化水素基を意味し、
R4は、同じであるか、または異なっていてよく、かつ水素原子を意味するか、または置換された、もしくは非置換の一価炭化水素基を意味し、
R5は、同じであるか、または異なっていてよく、かつ置換された、もしくは非置換のSiC結合した一価芳香族炭化水素基を意味し、
cは、0、1、2または3であり、
dは、0、1、2または3、好ましくは0、1または2、特に好ましくは0または1であり、かつ
eは、0、1または2、好ましくは0または1であり、ただし、c+d+eの合計は、0超3以下であり、さらにc+e≧1であり、好ましくは、式(I)の単位の少なくとも40個においてc+eの合計は1である]の単位を含むシリコーン樹脂(B)(シリコーン中間体)である。
RaSi(OR’)bO(4−a−b)/2 式(II)
[式中、Rは、互いに無関係に、炭素原子1〜8個を有するアルキル基および炭素原子6〜20個を有するアリール基またはアラルキル基の群から選択され、R’は、互いに無関係に、炭素原子1〜8個を有するアルキル基の群から選択され、1≦a<2かつa+b<4である]を満たす。
I)少なくとも1種の本発明によるバインダー、
II)任意で1種以上の追加的なバインダー成分、
III)任意で触媒、
IV)任意で助剤および添加剤、
V)任意で有機溶媒および
VI)任意でアミノシラン
を含むコーティング剤である。
好ましくは、遷移金属のキレートもしくは塩、高沸点の酸、第四級アンモニウムカルボキシレートまたは上述の化合物の組合せが用いられる。
好ましいアミノシランまたはアミノアルキルシランは、置換されたまたは非置換のアミノシラン化合物、特に3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、3−アミノプロピルメチルジエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、2−アミノプロピル−3−アミノプロピルトリメトキシシラン、2−アミノプロピル−3−アミノプロピルトリエトキシシラン、2−アミノエチル−2−アミノエチル−3−アミノプロピルトリメトキシシラン、2−アミノエチル−2−アミノエチル−3−アミノプロピルトリエトキシシランおよびN−(n−ブチル)−3−アミノプロピルトリメトキシシランである。
特に明記しない限り、実施例において百分率で記載した量は、重量基準である。
SILRES(登録商標)IC 368:メトキシ官能化メチル/フェニルポリシロキサン中間体、Wacker Chemie AG
Setalux 1767 VV−65:ポリアクリレートポリオール、Nuplex Resins B.V.
Setalux 1760 VB−64:ポリアクリレートポリオール、Nuplex Resins B.V.
Vestanat(登録商標)EP Cat 11B:ブタノール中のテトラエチルアンモニウムベンゾエート、Evonik Resource Efficiency GmbH
Vestanat(登録商標)EP−M60、Vestanat(登録商標)EP−M95、Vestanat(登録商標)EP−M120:多価アルコールとのイソシアナトプロピルトリメトキシシラン付加物、Evonik Resource Efficiency GmbH
29−Si−NMR試料の測定は、Bruker(登録商標)社の500MHz機器により行った。29−Si核の共鳴周波数は、39.7MHzである。すべての化学シフトは、テトラメチルシラン「TMS」に対して報告している(δ=0ppm)。測定ソフトウェアによりシグナルを統合することによって、スペクトルを定量的に評価した。より明確にするために、ここでは、式R3SiO1/2のM単位のシフトのみを報告する。
Vestanat EP−M60 200g、SILRES IC 368 200gおよびテトラエチルアンモニウムベンゾエート(TEAB)2gをフラスコに入れ、これに還流冷却器を取り付けた。次いで、混合物を撹拌しながら100℃に加熱した。6時間の反応時間後、得られたバインダー1を冷却した。その結果、469mPasの粘度(23℃)を有する透明な液体が得られた。DMSO中の29Si−NMRシグナル(ppm):−47(Me3SiO1/2からのSi3.6mol%)、−49(バインダー1からのSi M構造5.8mol%)。
Vestanat EP−M95 200g、SILRES IC 368 200gおよびテトラエチルアンモニウムベンゾエート(TEAB)2gをフラスコに入れ、これに還流冷却器を取り付けた。次いで、混合物を撹拌しながら100℃に加熱した。6時間の反応時間後、得られたバインダー2を冷却した。その結果、475mPasの粘度(23℃)を有する透明な液体が得られた。CDCl3中の29Si−NMRシグナル(ppm):−48(Me3SiO1/2からのSi3.5mol%)、−50(バインダー2からのSi M構造3.4mol%)。
Vestanat EP−M120 200g、SILRES IC 368 200gおよびテトラエチルアンモニウムベンゾエート(TEAB)2gをフラスコに入れ、次いで、撹拌しながら100℃に加熱した。6時間の反応時間後、得られたバインダー3を、キシレン30%で希釈し、冷却した。その結果、19mPasの粘度(23℃)を有する透明な液体が得られた。DMSO中の29Si−NMRシグナル(ppm):−47(Me3SiO1/2からのSi3.8mol%)、−49(バインダー3からのSi M構造6.2mol%)。
本発明によるそれぞれのバインダー50gに有機樹脂50g(表1参照)を混ぜ、室温で撹拌しながら混合した。透明な溶液が得られた場合、相溶性は「良好」と評価した。
本発明によるコーティング剤I〜VIの製造のために、表3に列記した生成物を室温で均質化した。
Claims (15)
- イソシアナトアルキルアルコキシシラン(A1)とアルコール(A2)の付加物(A)と、アルコキシシランを含有し、Q単位を含まないアルキルおよび/またはアリールシリコーン樹脂(B)とからの反応生成物をベースとするバインダー。
- 前記イソシアナトアルキルアルコキシシラン(A1)が、イソシアナトメチルトリメトキシシラン、イソシアナトメチルトリエトキシシラン、イソシアナトメチルトリイソプロポキシシラン、2−イソシアナトエチルトリメトキシシラン、2−イソシアナトエチルトリエトキシシラン、2−イソシアナトエチルトリイソプロポキシシラン、3−イソシアナト−n−プロピルトリメトキシシラン、3−イソシアナト−n−プロピルトリエトキシシラン、3−イソシアナト−n−プロピルトリイソプロポキシシラン、4−イソシアナト−n−ブチルトリメトキシシラン、4−イソシアナト−n−ブチルトリエトキシシランおよび4−イソシアナト−n−ブチルトリイソプロポキシシランを含む群から選択されることを特徴とする、請求項1記載のバインダー。
- 前記アルコール(A2)が、一価アルコールまたは多価アルコールであることを特徴とする、請求項1または2記載のバインダー。
- 前記多価アルコールが、エチレングリコール、1,2−プロパンジオール、1,3−プロパンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、1,10−デカンジオール、1,12−ドデカンジオール、グリセリン、イソソルビトール、イソマンニトール、イソイジトール、2,2,4−トリメチルヘキサンジオール−1,6および2,4,4−トリメチルヘキサンジオール−1,6を単独で、またはこれらの異性体の任意の混合物として、2,2−ジメチルブタンジオール−1,3、2−メチルペンタンジオール−2,4、3−メチルペンタンジオール−2,4、2,2,4−トリメチル−1−ペンタンジオール−1,3、2−エチルヘキサンジオール−1,3、2,2−ジメチルヘキサンジオール−1,3、3−メチルペンタンジオール−1,5、2−メチルペンタンジオール−1,5、2,2−ジメチルプロパンジオール−1,3(ネオペンチルグリコール)、ヒドロキシピバリン酸ネオペンチルグリコールエステル、ポリエチレングリコール、ポリプロプレングリコール、ソルビトール、ペンタエリスリトール、1,1,1−トリメチロールプロパン、3(4),8(9)−ビス(ヒドロキシメチル)−トリシクロ[5.2.1.02,6]デカン(ジシドール)および/または2,2−ビス(4−ヒドロキシシクロヘキシル)プロパンを含む群から選択されることを特徴とする、請求項3記載のバインダー。
- 前記アルコール(A2)のOH基対前記イソシアナトアルキルトリアルコキシシラン(A1)のNCO基のモル比が、0.8:1〜1.2:1であることを特徴とする、請求項1から4までのいずれか1項記載のバインダー。
- 用いられる前記シリコーン樹脂(B)が、次式(I)
R3 c(R4O)dR5 eSiO(4−c−d−e)/2 式(I)
[式中、
R3は、同じであるか、または異なっていてよく、かつ水素原子を意味するか、置換された、もしくは非置換のSiC結合した一価脂肪族炭化水素基を意味するか、または前記式(I)の2個の単位を橋かけする置換された、もしくは非置換の二価脂肪族炭化水素基を意味し、
R4は、同じであるか、または異なっていてよく、かつ水素原子を意味するか、または置換された、もしくは非置換の一価炭化水素基を意味し、
R5は、同じであるか、または異なっていてよく、かつ置換された、もしくは非置換のSiC結合した一価芳香族炭化水素基を意味し、
cは、0、1、2または3であり、
dは、0、1、2または3、好ましくは0、1または2、特に好ましくは0または1であり、かつ
eは、0、1または2、好ましくは0または1であり、
ただし、c+d+eの合計は、0超3以下であり、さらにc+e≧1である]の単位を含むシリコーン樹脂(B)であることを特徴とする、請求項1から5までのいずれか1項記載のバインダー。 - 前記シリコーン樹脂が、一般式(II)
RaSi(OR’)bO(4−a−b)/2 式(II)
[式中、
Rは、互いに無関係に、炭素原子1〜8個を有するアルキル基および炭素原子6〜20個を有するアリール基もしくはアラルキル基の群から選択され、
R’は、互いに無関係に、炭素原子1〜8個を有するアルキル基の群から選択され、
1≦a<2であり、かつ
a+b<4である]を有する、請求項1から6までのいずれか1項記載のバインダー。 - 任意で触媒(C)、アルコール(D)および/または水の存在下での、イソシアナトアルキルアルコキシシラン(A1)とアルコール(A2)とからの付加物(A)と、アルコキシシラン含有アルキルおよび/またはアリールシリコーン樹脂(B)との反応を含む、請求項1から7までのいずれか1項記載のバインダーを製造する方法。
- 付加物(A)とアルコキシシラン含有アルキルおよび/またはアリールシリコーン樹脂(B)との前記反応を、30〜150℃の範囲の温度で実施することを特徴とする、請求項8記載の方法。
- 触媒(C)として、融点>60℃を有する有機カルボン酸、テトラアルキルアンモニウムカルボキシレート、キレート配位子を有する金属錯体、有機Sn(IV)化合物、Sn(II)化合物、Zn化合物、Bi化合物、第三級アミン、リン含有触媒、好ましくはリンおよび窒素含有触媒、ブロックされていない形態の、もしくはブロックされた形態の有機スルホン酸、またはこれらの混合物を含む群から選択される触媒が用いられることを選択することを特徴とする、請求項8または9記載の方法。
- 付加物(A)とアルコキシシラン含有アルキルおよび/またはアリールシリコーン樹脂(B)を、同じ重量比で用いることを特徴とする、請求項8から10までのいずれか1項記載の方法。
- 塗料、接着剤およびシーラント用途の分野における、請求項1から7までのいずれか1項記載のバインダーの使用。
- I)請求項1から7までのいずれか1項記載の少なくとも1種のバインダー、
II)任意で1種以上の追加的なバインダー成分、
III)任意で触媒、
IV)任意で助剤および添加剤、
V)任意で有機溶媒および
VI)任意でアミノシラン
を含むコーティング剤。 - 触媒III)として、ルイス酸、金属もしくは遷移金属キレート、金属もしくは遷移金属塩、または金属もしくは遷移金属粒子、遊離した、あるいは中和または付加された形態のスルホン酸、リン酸もしくは亜リン酸およびそれらの誘導体、高沸点の酸、第四級アンモニウムカルボキシレートまたは上述の化合物の組合せが用いられることを特徴とする、請求項13または14記載のコーティング剤。
- 木材、中密度木質繊維板、紙、プラスチック、複合材、ガラス、テキスタイルまたは金属のコーティングのために用いられることを特徴とする、請求項13から15までのいずれか1項記載のコーティング剤。
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EP3524651A1 (de) | 2018-02-08 | 2019-08-14 | Evonik Degussa GmbH | Wässrige polyorganosiloxanhybridharz-dispersion |
BR112021000476B1 (pt) * | 2018-08-02 | 2023-10-24 | Akzo Nobel Coatings International B.V | Composição de revestimento 2k, método de revestimento de um susbtrato e substrato revestido |
US11359100B2 (en) * | 2018-09-10 | 2022-06-14 | Evonik Operations Gmbh | Tin-free catalysis of silane-functional polyurethane crosslinkers |
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