NL2017639B1 - Two component adhesive with improved open time - Google Patents
Two component adhesive with improved open time Download PDFInfo
- Publication number
- NL2017639B1 NL2017639B1 NL2017639A NL2017639A NL2017639B1 NL 2017639 B1 NL2017639 B1 NL 2017639B1 NL 2017639 A NL2017639 A NL 2017639A NL 2017639 A NL2017639 A NL 2017639A NL 2017639 B1 NL2017639 B1 NL 2017639B1
- Authority
- NL
- Netherlands
- Prior art keywords
- linear
- component
- dibutyltin
- branched
- bis
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 86
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 86
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- 229920000642 polymer Polymers 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000945 filler Substances 0.000 claims abstract description 12
- 229910000077 silane Inorganic materials 0.000 claims abstract description 12
- 239000003426 co-catalyst Substances 0.000 claims abstract description 11
- 239000003707 silyl modified polymer Substances 0.000 claims abstract description 9
- 239000002808 molecular sieve Substances 0.000 claims abstract description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 48
- 239000000565 sealant Substances 0.000 claims description 34
- -1 adhesion promotors Substances 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 24
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 229910021536 Zeolite Inorganic materials 0.000 claims description 13
- 239000010457 zeolite Substances 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 9
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 9
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 9
- 229920000570 polyether Polymers 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 150000001558 benzoic acid derivatives Chemical group 0.000 claims description 8
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000004014 plasticizer Substances 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000002274 desiccant Substances 0.000 claims description 6
- 125000005498 phthalate group Chemical class 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical group CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- UVDDHYAAWVNATK-VGKOASNMSA-L (z)-4-[dibutyl-[(z)-4-oxopent-2-en-2-yl]oxystannyl]oxypent-3-en-2-one Chemical compound CC(=O)\C=C(C)/O[Sn](CCCC)(CCCC)O\C(C)=C/C(C)=O UVDDHYAAWVNATK-VGKOASNMSA-L 0.000 claims description 4
- OZDOQMMXEACZAA-NRFIWDAESA-L (z)-4-butoxy-4-oxobut-2-enoate;dibutyltin(2+) Chemical compound CCCCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCCCC OZDOQMMXEACZAA-NRFIWDAESA-L 0.000 claims description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 4
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 claims description 4
- VYVFQBFOMKEKBG-UHFFFAOYSA-L 3,3-dibutyl-2,4,3-benzodioxastannepine-1,5-dione Chemical compound O=C1O[Sn](CCCC)(CCCC)OC(=O)C2=CC=CC=C21 VYVFQBFOMKEKBG-UHFFFAOYSA-L 0.000 claims description 4
- DRZLVZYYZKVLCK-SEYKUYGWSA-L 4-o-[[(e)-4-ethoxy-4-oxobut-2-enoyl]oxy-dioctylstannyl] 1-o-ethyl (e)-but-2-enedioate Chemical compound CCCCCCCC[Sn](CCCCCCCC)(OC(=O)\C=C\C(=O)OCC)OC(=O)\C=C\C(=O)OCC DRZLVZYYZKVLCK-SEYKUYGWSA-L 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 4
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 claims description 4
- GPDWNEFHGANACG-UHFFFAOYSA-L [dibutyl(2-ethylhexanoyloxy)stannyl] 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)O[Sn](CCCC)(CCCC)OC(=O)C(CC)CCCC GPDWNEFHGANACG-UHFFFAOYSA-L 0.000 claims description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 4
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 claims description 4
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 claims description 4
- 150000004705 aldimines Chemical class 0.000 claims description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 4
- OSGZEAQLLRZGHT-VGKOASNMSA-L dibutyltin(2+);(z)-4-ethoxy-4-oxobut-2-enoate Chemical compound CCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCC OSGZEAQLLRZGHT-VGKOASNMSA-L 0.000 claims description 4
- WNDWDJLPMLWBHW-UDVCPWNYSA-L dibutyltin(2+);(z)-4-methoxy-4-oxobut-2-enoate Chemical compound COC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OC WNDWDJLPMLWBHW-UDVCPWNYSA-L 0.000 claims description 4
- TUALPPJDVFLVNQ-KUAKSMGGSA-L dibutyltin(2+);(z)-4-oxo-4-phenylmethoxybut-2-enoate Chemical compound C=1C=CC=CC=1COC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCC1=CC=CC=C1 TUALPPJDVFLVNQ-KUAKSMGGSA-L 0.000 claims description 4
- JNKCYBSAZHJNIZ-LHJYRGMRSA-L dibutyltin(2+);(z)-4-oxo-4-tridecoxybut-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)\C=C/C(=O)O[Sn](CCCC)(CCCC)OC(=O)\C=C/C(=O)OCCCCCCCCCCCCC JNKCYBSAZHJNIZ-LHJYRGMRSA-L 0.000 claims description 4
- JSBWYSVKZOKTJJ-UHFFFAOYSA-L dibutyltin(2+);2-nonylphenolate Chemical compound CCCC[Sn+2]CCCC.CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-] JSBWYSVKZOKTJJ-UHFFFAOYSA-L 0.000 claims description 4
- ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 claims description 4
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 claims description 4
- SDTDHTCWRNVNAJ-UHFFFAOYSA-L dimethyltin(2+);diacetate Chemical compound CC(=O)O[Sn](C)(C)OC(C)=O SDTDHTCWRNVNAJ-UHFFFAOYSA-L 0.000 claims description 4
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 claims description 4
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- MTBVDKSFTCGOTN-UHFFFAOYSA-N octane pentane-2,4-dione tin(4+) Chemical compound [Sn+4].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O.CCCCCCC[CH2-].CCCCCCC[CH2-] MTBVDKSFTCGOTN-UHFFFAOYSA-N 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 239000004649 TEGOPAC® Substances 0.000 claims description 3
- 239000012963 UV stabilizer Substances 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 235000006708 antioxidants Nutrition 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 150000004658 ketimines Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 238000000518 rheometry Methods 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical class CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 claims description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical class CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 2
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical class CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000001723 curing Methods 0.000 description 9
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- GXJPKIGCMGAHTL-UHFFFAOYSA-N dipropyl benzene-1,4-dicarboxylate Chemical compound CCCOC(=O)C1=CC=C(C(=O)OCCC)C=C1 GXJPKIGCMGAHTL-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000003932 ketenimines Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- LQLQDKBJAIILIQ-UHFFFAOYSA-N Dibutyl terephthalate Chemical compound CCCCOC(=O)C1=CC=C(C(=O)OCCCC)C=C1 LQLQDKBJAIILIQ-UHFFFAOYSA-N 0.000 description 1
- 101000653542 Homo sapiens Transcription factor-like 5 protein Proteins 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 102100030647 Transcription factor-like 5 protein Human genes 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SQQSFUNTQGNWKD-UHFFFAOYSA-N dipentyl benzene-1,4-dicarboxylate Chemical compound CCCCCOC(=O)C1=CC=C(C(=O)OCCCCC)C=C1 SQQSFUNTQGNWKD-UHFFFAOYSA-N 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention is in the field of a two component adhesive, a method of making said adhesive, and use of said adhesive. The first component of the two component adhesive comprises a silyl modified polymer and/or hybrid polymer, a filler, a primary catalyst, and a co-catalyst, wherein the co-catalyst typically is a Blockde R. primary or secondary amino silane, and is protected from water, whereas the sec-ond component comprises a silyl modified polymer and/or hybrid polymer, a molecular sieve, and water.
Description
Title Two component adhesive with improved open time
FIELD OF THE INVENTION
The present invention is in the field of a two component adhesive, a method of making said adhesive, and use of said adhesive.
BACKGROUND OF THE INVENTION
The present invention is in the field of a two component elastic adhesive which may be used as a kit or as a sealant; the elastic adhesive may also be referred to as a high modulus sealant. Sealants may be characterized by elongation properties. Elongation relates to a length to which a sealant can be stretched, e.g. expressed as a percentage of its original size. The term "modulus" relates to the tensile strength of a sealant at a given amount of elongation, as may be determined by ISO 8340:2005 or ASTM C1135. At 100 percent elongation, a high modulus may be defined as >0.4 MPa, and a low modulus as <0.4 MPa (ISO 11600), although the numbers given should not be considered as exact "boundaries". The modulus is considered to have a direct effect on the elongation capacity, since the lower the tensile strength, the easier the sealant may stretch. High-modulus sealants are typically used where high strength is required and little movement is expected. Low-modulus sealants are typically used where movement capability is considered important. It is noted that typically one component of the two component adhesive comprises a non-reacted reactive polymer, and a second component comprises an activator c.q. a catalyst, which cures the polymer; in an alternative as a second component a reactive monomer, oligomer or polymer which is capable of reacting with the first component to form a cured product may be taken. In addition to two component adhesives also one component adhesives exits, which are typically activated by environmentally conditions, such as humidity, light, oxygen, etc. Below an indication is given of various requirements of adhesives for a better understanding. It is noted that it is rather difficult to adapt characteristics of adhesives to specific requirements. It is intrinsically difficult to adapt properties of an adhesive, also referred to as "sealant", as improving a first characteristic may typically result in a deterioration of a second characteristic.
General properties of adhesives are open time (working time to make a bond, where the surface still retains sufficient tack, which can range from seconds for fast-setting adhesives to infinity for pressure-sensitive adhesives), set time (time to form a bond of acceptable strength), dry time, (initial) tack ((initial) degree of surface stickiness of the adhesive), applicability and adhesion to a diverse range of substrate surfaces, contactibility, flexibility of an adhesive film, temperature stability, storage stability, viscosity, and surface energy (influences wetting of different kind of surfaces) .
Adhesives often consist of one base material with various additives. For a two-component adhesive a first and second component, each component optionally comprising more than one constituent, are mixed before applying, such as by a spray-gun, a sealant-gun typically equipped with a means of mixing both components, and a static mixer. The first and second component can typically not be stored in a mixed form.
Some of the possible base materials, each having advantages and disadvantages, are reactive poly-urethanes, silicones, poly-sulphides, silane-terminated polymers, and various other copolymers.
Many of the prior art adhesives need to be bonded directly, typically within a few seconds, as the open time is relatively short. Thereafter one needs to wait until the adhesive has reacted and has obtained sufficient strength. That characteristic makes such an adhesive not suited for larger surfaces, or not very well accessible surfaces. Others may have a long open time and do not need to be bonded immediately; these consequently will suffer from an increased curing time thus also increasing the complete construction time of a to be bonded product.
It is often also important to have a high initial strength. For many prior art adhesive initial strength is not sufficient. One has to wait until the bond is sufficiently strong. Adhesives are preferably also temperature stable.
The present invention is in particular concerned with a curing time of a sealant. For instance, a standard one component (1C) sealant layer will cure at a speed of 3-4 mm/day. And further, the thicker the layer is, the slower this cure speed becomes. A partial solution for application of such adhesives is to use a two component adhesive. A (two) component adhesive curing time is usually defined as the time to achieve a given strength. A further problem is that after being applied a sealant cures much slower. 1C sealants are found to cure through the presence (and reaction with) humidity in air. When a seal-ant/adhesive is in an environment where no (further) humidi-ty/moisture can enter (e.g. two metal or plastic plates), it does not cure or does not cure properly, e.g. only at the edges and not in a centre part of the sealant. A further problem is that when there is no humidity in the air or the humidity is very low (e.g. after a frost period or at low temperatures, especially a 1C sealant cures very slowly, in other words the cure will be retarded. A solution to the problem could be to use a two component adhesive. However, this is found to introduce a new problem. Although now it is possible to cure relatively fast, there is hardly any open time left. For adhering smaller parts such might be of minor interest, but especially when bigger parts need to be glued together, for example side panels to trucks, big windows or multiple windows, at least part of the adhesive applied on a first part is already cured too far to obtain a good adhesion to the second part. The cure speed could be reduced by tuning other parameters, such as by adding less catalyst to a two component adhesive, or by using a slower catalyst, or by using another polymer with a different reactivity, but these measures are found to immediately reduce the strength build up in time, it may reduce the cure speed, which will increase the production time on the product. This strength reduction minimalizes the effect of the higher cure rate, which is in general the basic reason to use a 2C adhesive .
Some prior art systems recite one component curable compositions, which will as a consequence suffer at least from the above disadvantages. EP 2 088 173 B1 recites a curable one component composition made mainly of an organic polymer having a reactive silicon group, which is claimed to exhibit a good curability without using any organic tin compound substantially, and gives a cured product having a sufficient strength; and to provide a catalyst composition. The object is solved by a curable composition, comprising a polymer (A) having a silicon-containing group which can be crosslinked by forming a silox-ane bond, a fluoride salt compound (B), as well as a filler (C) in the form of a precipitated calcium carbonate surface-treated with an aliphatic acid. The curable composition is a one component system, wherein further the carbonate is considered to absorb any water (or likewise humidity or moisture) being present. The composition does not solve the problem of obtaining a long open time, followed by a short curing time, in the absence of virtually any humidity c.q. water. EP 2 759 581 Ά1 recites a one component sealant composition that includes a reactive silyl group-containing organic polymer, and gives a cured product having a low modulus and not having wrinkles or cracks on the surface even though the sealant includes as a curing catalyst a tetravalent tin compound, which is presumed to reduce recovery. The sealant composition is a one-component curable sealant composition including: a linear organic polymer (A) having a number average molecular weight of 11,000 to 30,000, and having an ethanol-elimination reactive silyl group at a molecular terminal; a tetravalent tin compound (B); and a plasticizer (C). The composition does not solve the problem of obtaining a long open time, followed by a short curing time, in the absence of virtually any humidity c.q. water. In addition the sealant relates to a low modulus sealant. US2016/0130402 A1 recites moisture-curing compositions with increased storage stability based on compounds bearing silyl groups and use thereof. The one component curable composition comprises at least one silane compound having imine groups, and at least one prepolymer comprising at least one silyl group. Also these compositions do not solve the above problems; only a longer storage stability is claimed.
None of the above documents solves the problem of an improved curing time while maintaining a long open time.
There is therefore a need for improved two component adhesives. It is an object of the present invention to provide an adhesive which overcomes one or more of the above disadvantages, and a method of forming an adhesive, without jeopardizing functionality and advantages.
SUMMARY OF THE INVENTION
The present invention relates to an improved two component, typically elastic, adhesive according to claim 1, a method of applying said adhesive according to claim 11, and use of said adhesive according to claim 12. The present adhesive may be used as a kit or as a sealant; the present elastic adhesive is typically a high modulus sealant with a tensile strength >0.7 MPa, preferably 1-6 MPa, such as 1.5-5 MPa; by adapting the composition of the sealant the modulus can be adapted consequently, e.g. to 0.1-0.7 MPa, such as 0.3-0.7 or 0.4 MPa (ISO 11600) .
The first component of the present two component composition consists of 10-60 wt. % of a silyl modified polymer and/or hybrid polymer, preferably 20-50 wt. % polymer, such as 30-45 wt.%, e.g. 35-44 wt. %. It further consists of 10-50 wt. % of filler, preferably 20-45 wt.%, more preferably 30-40 wt.%. As an optional component a plasticizer is added in an amount of 0-30 wt.%, preferably 1-20 wt.%, more preferably 2-15 wt.%, even more preferably 3-10 wt.%, such as 4-7 wt.%. Further additives may be added in an amount of 0-15 wt.%, preferably 0.1-10 wt.%, more preferably 0.2-8 wt.%, even more preferably 0.3-7 wt.%, such as 0.4-6 wt.%. In addition 0.05 - 5 wt.% of a primary catalyst, preferably 0.1-3 wt.%, more preferably 0.5-2 wt.%, such as 1-2 wt.%, is present. The primary catalyst may be one or more of a tetravalent organotin compound, such as dimethyltin diacetate, dimethyltin bis(acetylacetonate), dibu-tyltin dilaurate, dibutyltin maleate, dibutyltin phthalate, dibutyltin dioctanoate, dibutyltin bis(2-ethylhexanoate), dibutyltin bis(methyl maleate), dibutyltin bis(ethyl maleate), dibutyltin bis(butyl maleate), dibutyltin bis(octyl maleate), dibutyltin bis(tridecyl maleate), dibutyltin bis(benzyl male-ate), dibutyltin diacetate, dioctyltin bis(ethyl maleate), di-octyltin bis(octyl male-ate), dibutyltin dimethoxide, dibutyltin bis(nonylphenoxide), dibutyltin oxide, dibutyltin bis(acetylacetonate), dibutyltin bis(ethyl acetoacetonate), a reaction product of dibutyltin oxide and a silicate compound, a reaction product of dibutyltin oxide and a phthalic acid ester, di-octyltin dilaurate, dioctyltin diacetate, dioctyltin bis(acetylacetonate), and reaction product of dioctyltin oxide and a silicate compound. The invention is characterized by a specific selection of co-catalyst, being different from the primary catalyst, wherein the co-catalyst is a blocked primary or secondary amino silane (ketimine silane or aldimine silane) with chemical formula { (R3) (R4) C=N}n (Rio) Si (ORi) 3-x (R2) x, wherein n=l or 2, and wherein Rio is an alkylene; the first component consists of 0.01 - 10 wt. % of a co-catalyst, preferably 0.02-5 wt.%, more preferably 0.1-3 wt.%, even more preferably 0.25-2 wt.%, such as 0.5-1 wt.%. In view of the co-catalyst no or only a very small amount of water is present, such as less than 0.1 wt.%, preferably less than 0.05 wt.%. To guarantee that the presence of water is low enough to prevent premature reaction of saponification of the ketenimine or aldimine it is preferred to use a chemical drying agent, such as vinyl-trimethoxysilane, and vinyl-triethyoxysilane. As a second component B consists of (bl) 10-90 wt.% of a silyl modified polymer and/or hybrid polymer, preferably 30-70 wt.%, such as 40-60 wt.%. The polymers of components A and B may be selected independently from one and another and may therefore be the same. Component B further consists of 10-70 wt.% of a molecular sieve with a pore diameter of 0.25-0.6 nm (2.5-6 A), more preferably 30-50 wt.%, even more preferably 40-45 wt.%. The pore diameter is preferably 0.3-0.55 nm, more preferably 0.35-0.5 nm, such as 0.4-0.45 nm. Component B further consists of 1-25 wt.% water, preferably 1.5-20 wt.%, more preferably 2-12 wt.%. All wt.% are based on a total weight of component A or B, respectively. Note that component A preferably does not contain (free) water and component B does not contain a catalyst. Upon application or shortly before application the two components are mixed. Upon mixing the components (A) and (B) are present in a volume ratio A:B of 100:3 to 1:1, preferably 20:1 to 2:1, more preferably 15:1 to 3:1, such as 10:1 to 5:1, i.e. component A is on a volume basis typically present in a surplus with respect to component B. It is noted that for practical purposes the components are mixed in a volume ratio; the volume ratio is often quite similar to a weight ratio. The present two component adhesive provides certain advantages, as detailed throughout the description, and overcomes problems of the prior art.
It has now be found that when the cure-catalyst is a blocked aminosilane, an open time is created hardly affecting (or not significantly) the cure speed. The blocked aminosilane (ketenimine silane) is in an example considered to react as follows:
i.e. upon addition of water an un-blocked amino-silane is formed, which latter amino-silane is found to cure the present adhesive. It is noted that the use of ketenime-blocked ami-nosilanes per se is well known. The chemistry may for instance be used for curing epoxy resins, thus making it possible to obtain 1C epoxy adhesives. The use of ketenimine-blocked silanes is also been described as a potential adhesive promotor, but to the knowledge of the inventors never as the cocatalyst for a 2C MS-sealant. It is the unblocking of the present co-catalyst which is found to provide a good curing over time, and in addition it also provides typically a long open time, a good built-up in strength, good skin formation, reduction of viscosity over time, and an increase of a viscosity ratio .
In a second aspect the present invention relates to a method of applying the present adhesive, comprising the steps of mixing the first and second component, applying the mixed composition to a surface, wherein after or during mixing, dur ing application and after application the blocked amino silane reacts with water and forms an amino-silane under release of an aldehyde (R3=H) or a ketone (ϊ^τΉ) . It is noted that the steps of mixing and applying may be performed sequentially or (almost) simultaneously. The present amino-silane starts to perform its catalytic action/activation after being formed upon contact with water, and starts to cure the present composition .
In a third aspect the present invention relates to a use of the present two component adhesive in an adhesive or in a sealant.
Thereby the present invention provides a solution to one or more of the above mentioned problems.
Advantages of the present description are detailed throughout the description. The teachings and examples of the present invention may be combined into a further not specifically disclosed exemplary embodiment.
DETAILED DESCRIPTION OF THE INVENTION
In a first aspect the invention relates to a two component adhesive according to claim 1.
In an exemplary embodiment of the present adhesive R3 is independently selected from H, C1-C15 linear or branched alkyls, preferably Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, sec-butyl, pentyl, iso-pentyl, hexyl, iso-hexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkyls, and linear or branched Ci-Cis-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N.
In an exemplary embodiment of the present adhesive x is 0 or 1.
In an exemplary embodiment of the present adhesive R4 is independently selected from C1-C15 linear or branched alkyls, preferably Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, sec-butyl, pentyl, iso-pentyl, hexyl, iso-hexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkylenes, and linear or branched Ci-Ci5-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N.
In an exemplary embodiment of the present adhesive Ri, and R2 are independently selected from hydrogen and Ci-Cs linear or branched alkyls, preferably C1-C4 linear or branched alkyls , such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, and tert-butyl.
In an exemplary embodiment of the present adhesive Rio is independently selected from C1-C15 linear or branched alkyls, preferably Ci-Ce linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, pentyl, iso-pentyl, hexyl, iso-hexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkyls, and linear or branched Ci-Cis-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N.
In an exemplary embodiment of the present adhesive the first component has a viscosity of 100-20000 Pa.s, preferably 500-5000 Pa.s at a shear rate of 0.5 s_1 (such as measured with a Rheosense microVISC (ISO 12092:2000).
In an exemplary embodiment of the present adhesive the second component has a viscosity of 10-2000 Pa.s at a shear rate of 0.5 s"1 (such as measured with a Rheosense microVISC (ISO 12092:2000).
In an exemplary embodiment of the present adhesive the molecular sieve is an aluminosilicate material, such as a zeolite, such as a zeolite 3A (0.6 K20:0.40 Na20:l Al2O3:2.0 ±0.1 Si02 : xH20) , zeolite 4A (lNa20: 1A1203 : 2.0±0 . IS1O2 : xH20) , and zeolite 5A (0.80CaO: 0.20Na20: 1A1203: 2.0±0 . IS1O2 : x H20) (e.g.
Sigma Aldrich AL-143, such as 208574, 208582, 208590, 208604, 208612, and 208620).
In an exemplary embodiment of the present adhesive the filler is selected from chalk, precipitated chalk, coated precipitated chalk, silica, carbon black, and combinations thereof. It is preferred to use fillers with a low amount of water; typically a water percentage is checked upon the present application of the filler. In principle fillers as chalk could absorb water as well, but in practice it is found that such does not happen significantly. The present filers therefore function mainly as fillers only.
In an exemplary embodiment of the present adhesive the plasticizer is selected from benzoates, phthalates, ter-ephthalates, polyols, hydrogenated versions of phthalates, terephthalates and benzoates, and combinations thereof. In view of toxicity polyols, terephthalates and benzoates are preferred. Examples of suitable terephthalates are dibutyl terephthalate, dipropyl terephthalate, and dipentyl tereph-thalate. Examples of suitable benzoates are mono-esters from benzoic acid and a Cs-Ci6 alcohol, preferably wherein the alcohol is a Cg-Cn alcohol, preferably a C10 alcohol. Suitable polyols are PPG-2000, PPG 1000, and PPG2500.
In an exemplary embodiment of the present adhesive the additives are selected from catalysts, rheology control agents, pigments, pigment pastes, anti-oxidants, HALS, UV stabilizers, adhesion promotors, drying agents, fungicide, bactericide, and combinations thereof. A typical amount of additive is 0.05-0.5 wt. % per additive, such as 0.1-0.2 wt. % (independently of one and another).
In an exemplary embodiment of the present adhesive the polymer comprises a functionalized polyether backbone with methoxysilane terminal groups, the modified silyl polymer comprises one or more -An-D-SiXYZ end groups wherein: A is a divalent linking group comprising at least one hetero atom, D is a divalent hydrocarbon residue with 1-12 C- atoms, X, Y, Z are each independently substituents on the Si atom, and are independently selected from Ci-Cs alkyl, Ci-Cs alkoxy, Ci-Cs acyloxy, and wherein at least one of the substituents X, Y, Z is a Ci-Cs alkoxy or Ci-Cs acyloxy, and n is 0 or 1.
In an exemplary embodiment of the present adhesive in the polymer A is preferably selected from oxygen, -NR'-, amide, carbamate, urea, imino, carboxylate, carbamoyl, amidino, and carbonate, wherein R'=H or C1-C4 alkyl, preferably oxygen or -NH-.
In an exemplary embodiment of the present adhesive in the polymer D is preferably selected from alkylene residues, such methylene, ethylene, and n-propylene.
In an exemplary embodiment of the present adhesive the polymer is selected from at least one of MS-polymersTM, dimethoxysilyl terminated polyether, trimethoxysilyl terminated polyether, S203H, S303H,S227, S327, SAX 220, SAX 260, SAX350, SAX400, SAT010, SAX015, SAX115, SAT145, MAX602, MAX92 3, MAX951, SAX750, SAX510, SAX520, SAX 530, SAX540, SAX580, SAX590, MAX 451, MAX 480, MAX850; Desmoseal®, for example S XP 2458, S XP 2636, S XP 2749, S XP 2774, S XP 2821; Geniosil® for example STP-E10, STP-E15, STP-E30, STP-E35, Evo-nik Polymer for example ST47, ST 48, ST 77, ST 61, ST 61 LV, ST 81, ST 80 and TEGOPAC® , for example Seal 100, Bond 150, and Bond 250.
In an exemplary embodiment of the present adhesive the primary catalyst is selected from one or more of a tetra-valent organotin compound, such as dimethyltin diacetate, di-methyltin bis(acetylacetonate), dibutyltin dilaurate, dibu-tyltin maleate, dibutyltin phthalate, dibutyltin dioctanoate, dibutyltin bis(2-ethylhexanoate), dibutyltin bis(methyl maleate) , dibutyltin bis(ethyl maleate), dibutyltin bis(butyl maleate) , dibutyltin bis(octyl maleate), dibutyltin bis(tridecyl maleate), dibutyltin bis(benzyl maleate), dibutyltin diacetate, dioctyltin bis(ethyl maleate), dioctyltin bis(octyl male-ate), dibutyltin dimethoxide, dibutyltin bis(nonyl-phenoxide), dibutyltin oxide, dibutyltin bis(acetylacetonate), dibutyltin bis(ethyl acetoacetonate), a reaction product of dibutyltin oxide and a silicate compound, a reaction product of dibutyltin oxide and a phthalic acid ester, di-octyltin dilaurate, dioctyltin diacetate, dioctyltin bis(acetylacetonate) , and reaction product of dioctyltin oxide and a silicate compound.
In a second aspect the invention relates to a method according to claim 11.
In an exemplary embodiment of the present method the first and second component are mixed in a weight ratio A:B of 100:3 to 1:1. Typically a first surface may be provided with the present adhesive in an amount of 150-600 gr/m2, such as 250-500 gr/m2.
In an exemplary embodiment of the method the adhesive is applied with a sealant gun.
In an exemplary embodiment of the method the adhesive is applied at a temperature of 5 °C-45 °C, preferably 10 °C-35 °C. Therewith the present adhesive can be applied at given working temperatures.
In a third aspect the invention relates to a use according to claim 11.
In an exemplary embodiment the present use is in a method for improving at least one of open time, built-up in strength, skin formation, reducing viscosity over time, and increasing a viscosity ratio.
In an exemplary embodiment the present use is for sealing or bonding joints in transport vehicles, such as cars, trucks, busses, trains, vans, motorhomes, caravans, and trailers, ships, such as yachts, ships, and boats, or for adhering a first surface to a second surface. It may also be used for sealants for buildings, such as homes, sheds, factories, offices, and high rise buildings, road-infrastructure, such as viaducts, bridges, and fly-overs.
The invention is further detailed by the accompanying figures and examples, which are exemplary and explanatory of nature and are not limiting the scope of the invention. To the person skilled in the art it may be clear that many variants, being obvious or not, may be conceivable falling within the scope of protection, defined by the present claims.
BRIEF DESCRIPTION OF THE FIGURES
Figs, la-g show various characteristics of prior art adhesives comprising a varying amount of aminosilane (ΔΜΕΟ).
Figs. 2a-g show various characteristics of present adhesives comprising a varying amount of blocked aminosilane (AMEO).
DETAILED DESCRIPTION OF THE FIGURES
Figs, la-g show various characteristics of prior art adhesives comprising a varying amount of aminosilane (AMEO) for an adhesive composition shown in the below examples. In fig. la the amount of amino silane is given on the vertical axis (wt.% of total composition). On the horizontal axis the amount of catalyst is given ( wt.%). The viscosity after 3 days of the tested two-component adhesive is given in Pa*s. As can be concluded from the figure is that within the given cat alyst range (0.5-3 wt.%) the viscosity only depends on the amount of AMEO, from about 1200 Pa*s (top region) to about 2600 Pa*s (bottom region). Fig. lb gives the viscosity after 14 days, varying from about 800 Pa*s (top region) to about 3200 Pa*s (bottom region) indicating that the adhesive is stable over time. Fig. lc shows the viscosity ratio of the results after 14 days (fig la) and 3 days (figlb)which varies form 1 (top region) to 1.3 (bottom region) indicating that the adhesive is stable over time. Fig. Id shows the strength build-up (N/mm2) in 24 hours; it is clear that a higher amount of catalyst (from left to right) increase the strength significantly, whereas the amount of AMEO shows a minor but noticeable effect in this respect; in a left bottom region the strength is about 0.4 N/mm2, whereas in a right top section it is 1.2 N/mm2. From fig. le it can be seen that at the same time the open time (in minutes) decreases from 60 (top left) to less than 10 minutes (bottom right), which is considered too short for several applications. Fig. If shows that there is not much difference in through cure speed, varying from 3 mm (top) to 3.5 mm (bottom) and which cure speed is only found to depend on the amount of AMEO slightly. Figure lg shows the time it takes to reach a strength of 1 MPa in the cured sealant. This varies from 25 hours (left) to less than 5 hours showing the influence of the catalyst on the cure time and also showing that this is independent of the aminosilane.
Figs. 2a-g show various characteristics of present adhesives comprising a varying amount of blocked aminosilane (3-(1,3-dimethylbutylidene)aminopropyltriethoxysilane) for an adhesive composition of the examples below. In fig. 2a the amount of amino silane is given on the vertical axis (wt.% of total composition). On the horizontal axis the amount of catalyst is given ( wt.%). The viscosity after 3 days of the tested two-component adhesive is given in Pa*s. As can be concluded from the figure is that within the given catalyst range (0.5-3 wt.%) the viscosity not only depends on the amount of AMEO but also on the amount of catalyst (a.o. the present blocked amino silane), from about 1200 Pa*s (top region) to about 2100 Pa*s (bottom region). Fig. 2b gives the viscosity after 14 days, varying from about 500 Pa*s (top region) to about 3200 Pa*s (bottom region) indicating that the adhesive is stable over time, now being fully dependent on the amount of AMEO only. Fig. 2c shows the viscosity ratio (between freshly applied and older sealant after 14 days at 313 K (40 °C)) which varies from 1 (top left region) to 1.3 (bottom middle region). This again shows the stability of the formula of the present invention. Fig. 2d shows the strength build-up (N/mm2) in 24 hours; it is clear the strength built-up has now become completely dependable on the level of catalyst and is completely independent of the amount of blocked aminosilane; in a left region the strength is about 0.3 N/mm2, whereas in a right section it is 1.1 N/mm2. The strength-built-up is in the same level as with the prior art adhesive with AMEO. From fig. 2e it can be seen that the skin formation is almost independent of the amount of blocked aminosilane. But even more important the decrease is now from 180 to 20 minutes (instead of 60 to 10 for the prior art). This provides the option to tune this characteristics over a wide and acceptable range of time. So the use of a blocked aminosilane allows the choice of a long open time and high speed strength built-up. For example the open time for a strength built-up of 0,95 N/mm2 increase from 18 minutes for standard AMEO to 39 minutes with a blocked aminosilane of the present invention. Fig. 2f shows that there is some difference in through cure speed, varying from 2.7 mm (top left and right) to 3.5 mm (bottom middle) and which cure speed is thus found to depend on the amount of AMEO and slightly on the amount of catalyst. Figure 2g shows the time it takes to reach a strength of 1 MPa in the cured sealant. This varies from 35 hours (left) to less than 10 hours showing the influence of the catalyst on the cure time and also showing that this is independent of the aminosilane. Combining the information of figures le and 2e with figures If and 2f or with figures lg and 2g show that while the open time has been greatly enhanced only a limited effect is found on the cure time and strength build-up.
EXAMPLES
Part A was prepared as follows (experiments 1-4):
The differences in initial reactivity may best be shown by the skin formation time of the part A:
From these data it is easily seen that the experiments containing a blocked aminosilane have a very low initial reactivity.
Part B was made by mixing: 50 mass% MS-polymer, 40% Zeolite 3 Angstrom and 10% water.
When part A and Part B are now mixed together a new window of formulation opportunities arises. This is shown in the figures, e.g. figures le and 2e where it can be seen that the open time may now be varied from an initial open time of 10-50 minutes to 20 to >180 minutes by a further variation of the amount of catalyst.
It should be appreciated that for commercial application it may be preferable to use one or more variations of the present system, which would similar be to the ones disclosed in the present application.
The following section is added to support the search to the prior art and it reflects the translation of the last section into English. 1. Two component adhesive composition consisting of a first component(A) comprising (consisting of) (al) 10 - 60 wt. % of a silyl modified polymer and/or hybrid polymer, (a2) 10 - 50 wt. % of filler, (a3) 0-30 wt. % of a plasticizer, (a4) 0-15 wt. % additives, (a5) 0.05 - 5 wt. % of a primary catalyst, preferably 0.1- 3 wt.%, more preferably 0.5-2 wt.%, such as 1-2 wt. %, (a6) 0.01 - 10 wt.% of a co-catalyst, preferably 0.02-5 wt.%, more preferably 0.1-3 wt.%, even more preferably 0.25-2 wt.%, such as 0.5-1 wt.%, wherein the co-catalyst is a blocked primary or secondary amino silane (ketimine silane or aldimine silane) with chemical formula { (R3) (R4) C=N}n (R10) Si (ORi) 3_x (R2) x, wherein n=l or 2, and wherein Ri0 is an alkylene, (al) 0.1-5 wt.% of a drying agent, as a second component (B)consisting of (bl) 10-90 wt.% of a silyl modified polymer and/or hybrid polymer, preferably 30-70 wt.%, (b2) 10-70 wt.% of a molecular sieve with a pore diameter of 0.25-0.6 nm (2.5-6 A), more preferably 30-50 wt.%, (b3) 1-25 wt.% water, preferably 1.5-20 wt.%, more pref erably 2-12 wt.%, wherein all wt.% are based on a total weight of component A or B, respectively, wherein upon mixing the components (A) and (B) are present in a volume ratio A:B of 100:3 to 1:1, preferably 20:1 to 2:1, more preferably 15:1 to 3:1, such as 10:1 to 5:1. 2. Two component composition according to claim 1, wherein R3 is independently selected from H, C1-C15 linear or branched alkyls, preferably Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, pentyl, iso-pentyl, hexyl, iso-hexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkyls, and linear or branched C1-C15-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N, and/or x is 0 or 1, and/or wherein R4 is independently selected from C1-C15 linear or branched alkyls, preferably Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, pentyl, iso-pentyl, hexyl, isohexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkylenes, and linear or branched Ci-Ci5-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N, and/or wherein Ri, and R2 are independently selected from hydrogen and Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl and tert-butyl, and/or wherein Rio is independently selected from C1-C15 linear or branched alkyls, preferably Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, pentyl, iso-pentyl, hexyl, isohexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkyls, and linear or branched Ci-Ci5-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N. 3. Two component composition according to any of the preceding claims, wherein the first component has a viscosity of 100-10000 Pa.s, preferably 500-5000 Pa.s, and/or wherein the second component has a viscosity of 10-1000 Pa.s.
4. Two component composition according to any of the preceding claims, wherein the molecular sieve is an aluminosilicate material, such as a zeolite, such as a zeolite 3A (0.6 K20:0.40 Na2<0:l AI2O3: 2.0±0 . IS1O2: xPhO) , zeolite 4A (lNa20: IAI2O3: 2.0±0 . IS1O2: XH2O) , and zeolite 5A (0.80CaO: 0.20Na20:1A1203:2.0±0 . lSi02:x H20) . 5. Two component composition according to any of the preceding claims, wherein the filler is selected from chalk, precipitated chalk, coated precipitated chalk, silica, carbon black, and combinations thereof, and/or wherein the drying agent is selected from methoxy silanes and ethoxy silanes, preferably trimethoxy silanes and triethoxy silanes, such as vinyl-trimethoxysilane, and vinyl-triethyoxysilane. 6. Two component composition according to any of the preceding claims, wherein the plasticizer is selected from benzoates, phthalates, terephthalates, polyols, hydrogenated versions of phthalates, terephthalates and benzoates, and combinations thereof. 7. Two component composition according to any of the preceding claims, wherein the additives are selected from catalysts, rheology control agents, pigments, pigment pastes, anti-oxidants (examples in the description), HALS, UV stabilizers, adhesion promotors, fungicide, bactericide, and combinations thereof. 8. Two component composition according to any of the preceding claims, wherein the polymer comprises a functionalized polyether backbone with methoxysilane terminal groups, the modified silyl polymer comprises one or more -An-D-SiXYZ end groups wherein: A is a divalent linking group comprising at least one hetero atom, D is a divalent hydrocarbon residue with 1-12 C-atoms, X, Y, Z are each independently substituents on the Si atom, and are independently selected from Ci-Cs alkyl, Ci-Cs alkoxy, Ci-Cs acyloxy, and wherein at least one of the substituents X, Y, Z is a Ci-Cs alkoxy or Ci-Cs acyloxy, and n is 0 or 1, wherein A is preferably selected from oxygen, -NR'-, amide, carbamate, urea, imino, carboxylate, carbamoyl, amidino, and carbonate, wherein R'=H or C1-C4 alkyl, preferably oxygen or -NH-, and/or wherein D is preferably selected from alkylene residues, such methylene, ethylene, and n-propylene. 9. Two component composition according to any of the preceding claims, wherein the polymer is selected from at least one of MS-polymersTM, dimethoxysilyl terminated polyether, trimethoxysilyl terminated polyether, S203H, S303H,S227, S327, SAX 220, SAX 260, SAX350, SAX400, SAT010, SAX015, SAX115, SAT145, MAX602, MAX923, MAX951, SAX750, SAX510, SAX520, SAX 530, SAX540, SAX580, SAX590, MAX 451, MAX 480, MAX850; Desmoseal®, for example S XP 2458, S XP 2636, S XP 2749, S XP 2774, S XP 2821; Geniosil® for example STP-E10, STP-E15, STP-E30, STP-E35, Evonik Polymer for example ST47, ST 48, ST 77, ST 61, ST 61 LV, ST 81, ST 80 and TEGOPAC® , for example Seal 100, Bond 150, and Bond 250. 10. Two component composition according to any of the preceding claims, wherein the primary catalyst is selected from one or more of a tetravalent organotin compound, such as dimethyltin diacetate, dimethyltin bis(acetylacetonate) , dibutyltin dilaurate, dibutyltin maleate, dibutyltin phthalate, dibutyltin dioctanoate, dibutyltin bis (2-ethylhexanoate), dibutyltin bis(methyl maleate), dibutyltin bis(ethyl maleate), dibutyltin bis(butyl maleate), dibutyltin bis(octyl maleate), dibutyltin bis(tridecyl maleate) , dibutyltin bis(benzyl maleate), dibutyltin diacetate, dioctyltin bis(ethyl maleate), dioctyltin bis(octyl male-ate) , dibutyltin dimethoxide, dibutyltin bis(nonylphenoxide) , dibutyltin oxide, dibutyltin bis(acetylacetonate), dibutyltin bis(ethyl acetoace-tonate) , a reaction product of dibutyltin oxide and a silicate compound, a reaction product of dibutyltin oxide and a phthalic acid ester, di-octyltin dilaurate, dioctyltin diacetate, dioctyltin bis(acetylacetonate), and reaction product of dioctyltin oxide and a silicate compound. 11. Method of applying a two component composition according to any of claims 1-10, comprising the steps of mixing the first and second component, applying the mixed composition to a surface, wherein after or during mixing, during application and after application the blocked amino silane reacts with water and forms an amino-silane under release of an aldehyde (R3=H) or a ketone (R3^H) . 12. Method according to claim 11, wherein the first and second component are mixed in a weight ratio A:B of 100:3 to 1:1. 13. Use of a composition according to any of claims 1-10, in an adhesive or in a sealant. 14. Use according to claim 13, in a method for improving at least one of open time, built-up in strength, skin formation, reducing viscosity over time, and increasing a viscosity ratio. 15. Use according to any of claims 13-14 for sealing or bonding joints in transport vehicles, such as cars, trucks, busses, trains, vans, motorhomes, caravans, and trailers, ships, such as yachts, ships, and boats, or for adhering a first surface to a second surface.
Claims (15)
- The following section is added to support the search to the prior art and it reflects the translation of the claims into English.1. Two component adhesive composition consisting of a first component(A) comprising (consisting of) (al) 10 - 60 wt. % of a silyl modified polymer and/or hybrid polymer, (a2) 10 - 50 wt. % of filler, (a3) 0-30 wt. % of a plasticizer, (a4) 0-15 wt. % additives, (a5) 0.05 - 5 wt. % of a primary catalyst, preferably 0.1- 3 wt.%, more preferably 0.5-2 wt.%, such as 1-2 wt. %, (a6) 0.01 - 10 wt.% of a co-catalyst, preferably 0.02-5 wt.%, more preferably 0.1-3 wt.%, even more preferably 0.25-2 wt.%, such as 0.5-1 wt.%, wherein the co-catalyst is a blocked primary or secondary amino silane (ketimine silane or aldimine silane) with chemical formula { (R3) (R4) C=N}n (R10) Si (ORi) 3_x (R2) x, wherein n=l or 2, and wherein Ri0 is an alkylene, (al) 0.1-5 wt.% of a drying agent, as a second component (B)consisting of (bl) 10-90 wt.% of a silyl modified polymer and/or hybrid polymer, preferably 30-70 wt.%, (b2) 10-70 wt.% of a molecular sieve with a pore diameter of 0.25-0.6 nm (2.5-6 A), more preferably 30-50 wt.%, (b3) 1-25 wt.% water, preferably 1.5-20 wt.%, more pref erably 2-12 wt.%, wherein all wt.% are based on a total weight of component A or B, respectively, wherein upon mixing the components (A) and (B) are present in a volume ratio A:B of 100:3 to 1:1, preferably 20:1 to 2:1, more preferably 15:1 to 3:1, such as 10:1 to 5:1.
- 2. Two component composition according to claim 1, wherein R3 is independently selected from H, C1-C15 linear or branched alkyls, preferably Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, pentyl, iso-pentyl, hexyl, iso-hexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkyls, and linear or branched C1-C15-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N, and/or x is 0 or 1, and/or wherein R4 is independently selected from C1-C15 linear or branched alkyls, preferably Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, pentyl, iso-pentyl, hexyl, isohexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkylenes, and linear or branched Ci-Ci5-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N, and/or wherein Ri, and R2 are independently selected from hydrogen and C1-C8 linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl and tert-butyl, and/or wherein Rio is independently selected from C1-C15 linear or branched alkyls, preferably Ci-Cs linear or branched alkyls, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, pentyl, iso-pentyl, hexyl, isohexyl, heptyl, and octyl, C1-C15 linear or branched aromatic alkyls, C1-C15 linear or branched aralkyls, and linear or branched Ci-Ci5-aryls, optionally containing one or more hetero atoms chosen from 0, S, and N.
- 3. Two component composition according to any of the preceding claims, wherein the first component has a viscosity of 100-10000 Pa.s, preferably 500-5000 Pa.s, and/or wherein the second component has a viscosity of 10-1000 Pa.s.
- 4. Two component composition according to any of the preceding claims, wherein the molecular sieve is an aluminosilicate material, such as a zeolite, such as a zeolite 3A (0.6 K20:0.40 Na2<0:l AI2O3: 2.0±0 . IS1O2: xPRO) , zeolite 4A (lNa20: IAI2O3: 2.0±0 . IS1O2: XH2O) , and zeolite 5A (0.80CaO: 0.20Na20:1A1203:2.0±0 . lSi02:x H20) .
- 5. Two component composition according to any of the preceding claims, wherein the filler is selected from chalk, precipitated chalk, coated precipitated chalk, silica, carbon black, and combinations thereof, and/or wherein the drying agent is selected from methoxy silanes and ethoxy silanes, preferably trimethoxy silanes and triethoxy silanes, such as vinyl-trimethoxysilane, and vinyl-triethyoxysilane.
- 6. Two component composition according to any of the preceding claims, wherein the plasticizer is selected from benzoates, phthalates, terephthalates, polyols, hydrogenated versions of phthalates, terephthalates and benzoates, and combinations thereof.
- 7. Two component composition according to any of the preceding claims, wherein the additives are selected from catalysts, rheology control agents, pigments, pigment pastes, anti-oxidants (examples in the description), HALS, UV stabilizers, adhesion promotors, fungicide, bactericide, and combinations thereof.
- 8. Two component composition according to any of the preceding claims, wherein the polymer comprises a functionalized polyether backbone with methoxysilane terminal groups, the modified silyl polymer comprises one or more -An-D-SiXYZ end groups wherein: A is a divalent linking group comprising at least one hetero atom, D is a divalent hydrocarbon residue with 1-12 C-atoms, X, Y, Z are each independently substituents on the Si atom, and are independently selected from Ci-C8 alkyl, Ci-C8 alkoxy, Ci-C8 acyloxy, and wherein at least one of the substituents X, Y, Z is a Ci-C8 alkoxy or Ci-C8 acyloxy, and n is 0 or 1, wherein A is preferably selected from oxygen, -NR'-, amide, carbamate, urea, imino, carboxylate, carbamoyl, amidino, and carbonate, wherein R'=H or C1-C4 alkyl, preferably oxygen or -NH-, and/or wherein D is preferably selected from alkylene residues, such methylene, ethylene, and n-propylene.
- 9. Two component composition according to any of the preceding claims, wherein the polymer is selected from at least one of MS-polymersTM, dimethoxysilyl terminated polyether, trimethoxysilyl terminated polyether, S203H, S303H,S227, S327, SAX 220, SAX 260, SAX350, SAX400, SAT010, SAX015, SAX115, SAT145, MAX602, MAX923, MAX951, SAX750, SAX510, SAX520, SAX 530, SAX540, SAX580, SAX590, MAX 451, MAX 480, MAX850; Desmoseal®, for example S XP 2458, S XP 2636, S XP 2749, S XP 2774, S XP 2821; Geniosil® for example STP-E10, STP-E15, STP-E30, STP-E35, Evonik Polymer for example ST47, ST 48, ST 77, ST 61, ST 61 LV, ST 81, ST 80 and TEGOPAC® , for example Seal 100, Bond 150, and Bond 250.
- 10. Two component composition according to any of the preceding claims, wherein the primary catalyst is selected from one or more of a tetravalent organotin compound, such as dimethyltin diacetate, dimethyltin bis(acetylacetonate) , dibutyltin dilaurate, dibutyltin maleate, dibutyltin phthalate, dibutyltin dioctanoate, dibutyltin bis (2-ethylhexanoate), dibutyltin bis(methyl maleate), dibutyltin bis(ethyl maleate), dibutyltin bis(butyl maleate), dibutyltin bis(octyl maleate), dibutyltin bis(tridecyl maleate) , dibutyltin bis(benzyl maleate), dibutyltin diacetate, dioctyltin bis(ethyl maleate), dioctyltin bis(octyl male-ate) , dibutyltin dimethoxide, dibutyltin bis(nonylphenoxide) , dibutyltin oxide, dibutyltin bis(acetylacetonate), dibutyltin bis(ethyl acetoace-tonate) , a reaction product of dibutyltin oxide and a silicate compound, a reaction product of dibutyltin oxide and a phthalic acid ester, di-octyltin dilaurate, dioctyltin diacetate, dioctyltin bis(acetylacetonate), and reaction product of dioctyltin oxide and a silicate compound.
- 11. Method of applying a two component composition according to any of claims 1-10, comprising the steps of mixing the first and second component, applying the mixed composition to a surface, wherein after or during mixing, during application and after application the blocked amino silane reacts with water and forms an amino-silane under release of an aldehyde (R3=H) or a ketone (R3^H) .
- 12. Method according to claim 11, wherein the first and second component are mixed in a weight ratio A:B of 100:3 to 1:1.
- 13. Use of a composition according to any of claims 1-10, in an adhesive or in a sealant.
- 14. Use according to claim 13, in a method for improving at least one of open time, built-up in strength, skin formation, reducing viscosity over time, and increasing a viscosity ratio.
- 15. Use according to any of claims 13-14 for sealing or bonding joints in transport vehicles, such as cars, trucks, busses, trains, vans, motorhomes, caravans, and trailers, ships, such as yachts, ships, and boats, or for adhering a first surface to a second surface.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL2017639A NL2017639B1 (en) | 2016-10-19 | 2016-10-19 | Two component adhesive with improved open time |
| PCT/NL2017/050684 WO2018074925A1 (en) | 2016-10-19 | 2017-10-19 | Two component adhesive with improved open time |
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| Application Number | Priority Date | Filing Date | Title |
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| NL2017639A NL2017639B1 (en) | 2016-10-19 | 2016-10-19 | Two component adhesive with improved open time |
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| NL2017639B1 true NL2017639B1 (en) | 2018-04-26 |
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| NL2017639A NL2017639B1 (en) | 2016-10-19 | 2016-10-19 | Two component adhesive with improved open time |
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| NL (1) | NL2017639B1 (en) |
| WO (1) | WO2018074925A1 (en) |
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| NL2021734B1 (en) * | 2018-09-28 | 2020-05-07 | Strongbond B V | Silyl modified polymer composition with improved booster |
| WO2020164717A1 (en) * | 2019-02-14 | 2020-08-20 | Wacker Chemie Ag | Multi-component crosslinkable masses based on organyloxysilane-terminated polymers |
| KR20250160439A (en) * | 2023-03-15 | 2025-11-13 | 디디피 스페셜티 일렉트로닉 머티리얼즈 유에스, 엘엘씨 | 2-component thermally conductive adhesive |
| CN121511273A (en) | 2023-06-13 | 2026-02-10 | 泽费罗斯股份有限公司 | A two-component system containing an accelerator that can be wetted and cured |
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| US6124235A (en) * | 1993-09-22 | 2000-09-26 | Rhone-Poulenc Chimie | Accelerator system for crosslinking polymers which harden on exposure to the moisture in air |
| US6271333B1 (en) * | 1999-04-22 | 2001-08-07 | The Yokohama Rubber Co., Ltd. | One-part moisture curable composition |
| WO2008133265A1 (en) * | 2007-04-24 | 2008-11-06 | Kaneka Corporation | Curable composition |
| EP2465895A1 (en) * | 2010-12-15 | 2012-06-20 | Merz+Benteli AG | Heat curable adhesive, sealant and coating |
| US20160130402A1 (en) * | 2013-07-12 | 2016-05-12 | Evonik Degussa Gmbh | Curable compositions containing silyl groups and having improved storage stability |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2088173B1 (en) | 2006-11-22 | 2012-02-22 | Kaneka Corporation | Curable composition and catalyst composition |
| EP2759581B1 (en) | 2011-09-22 | 2018-01-24 | Kaneka Corporation | Curable composition and cured product thereof |
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2016
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2017
- 2017-10-19 WO PCT/NL2017/050684 patent/WO2018074925A1/en not_active Ceased
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| US6124235A (en) * | 1993-09-22 | 2000-09-26 | Rhone-Poulenc Chimie | Accelerator system for crosslinking polymers which harden on exposure to the moisture in air |
| US6271333B1 (en) * | 1999-04-22 | 2001-08-07 | The Yokohama Rubber Co., Ltd. | One-part moisture curable composition |
| WO2008133265A1 (en) * | 2007-04-24 | 2008-11-06 | Kaneka Corporation | Curable composition |
| EP2465895A1 (en) * | 2010-12-15 | 2012-06-20 | Merz+Benteli AG | Heat curable adhesive, sealant and coating |
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