BR112018008819B1 - Composição de cianoacrilato, método para sua preparação e método para ligação em conjunto de dois substratos - Google Patents
Composição de cianoacrilato, método para sua preparação e método para ligação em conjunto de dois substratos Download PDFInfo
- Publication number
- BR112018008819B1 BR112018008819B1 BR112018008819-6A BR112018008819A BR112018008819B1 BR 112018008819 B1 BR112018008819 B1 BR 112018008819B1 BR 112018008819 A BR112018008819 A BR 112018008819A BR 112018008819 B1 BR112018008819 B1 BR 112018008819B1
- Authority
- BR
- Brazil
- Prior art keywords
- crown
- cyanoacrylate
- composition according
- component
- anhydride
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 188
- 229920001651 Cyanoacrylate Polymers 0.000 title claims abstract description 80
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical group COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 239000000758 substrate Substances 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 31
- 229920001971 elastomer Polymers 0.000 claims abstract description 31
- 239000005060 rubber Substances 0.000 claims abstract description 30
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 24
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 44
- 239000000654 additive Substances 0.000 claims description 29
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 25
- 239000005977 Ethylene Substances 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 24
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical group C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- WDXYVJKNSMILOQ-UHFFFAOYSA-N 1,3,2-dioxathiolane 2-oxide Chemical compound O=S1OCCO1 WDXYVJKNSMILOQ-UHFFFAOYSA-N 0.000 claims description 16
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 230000000717 retained effect Effects 0.000 claims description 16
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 15
- -1 poly(ethylene glycol) Polymers 0.000 claims description 15
- 239000000853 adhesive Substances 0.000 claims description 14
- 230000001070 adhesive effect Effects 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- 239000003381 stabilizer Substances 0.000 claims description 11
- 229910000831 Steel Inorganic materials 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000010959 steel Substances 0.000 claims description 9
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical group CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 7
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 229920000858 Cyclodextrin Polymers 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- PLVUIVUKKJTSDM-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfonylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1 PLVUIVUKKJTSDM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000003983 crown ethers Chemical class 0.000 claims description 4
- 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 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- ITCZEZQMUWEPQP-UHFFFAOYSA-N prop-2-enyl 2-cyanoprop-2-enoate Chemical compound C=CCOC(=O)C(=C)C#N ITCZEZQMUWEPQP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 claims description 2
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 claims description 2
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 2
- AXWCVSOBRFLCJG-UHFFFAOYSA-N 2,5,12,15,22,25-hexaoxatetracyclo[24.4.0.06,11.016,21]triaconta-1(30),6,8,10,16,18,20,26,28-nonaene Chemical compound O1CCOC2=CC=CC=C2OCCOC2=CC=CC=C2OCCOC2=CC=CC=C21 AXWCVSOBRFLCJG-UHFFFAOYSA-N 0.000 claims description 2
- KCONMNWPRXAWKK-UHFFFAOYSA-N 2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 KCONMNWPRXAWKK-UHFFFAOYSA-N 0.000 claims description 2
- SVJYFWHFQPBIOY-UHFFFAOYSA-N 7,8,16,17-tetrahydro-6h,15h-dibenzo[b,i][1,4,8,11]tetraoxacyclotetradecine Chemical compound O1CCCOC2=CC=CC=C2OCCCOC2=CC=CC=C21 SVJYFWHFQPBIOY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 claims description 2
- MXCSCGGRLMRZMF-UHFFFAOYSA-N dibenzo-30-crown-10 Chemical compound O1CCOCCOCCOCCOC2=CC=CC=C2OCCOCCOCCOCCOC2=CC=CC=C21 MXCSCGGRLMRZMF-UHFFFAOYSA-N 0.000 claims description 2
- IKJFYINYNJYDTA-UHFFFAOYSA-N dibenzothiophene sulfone Chemical compound C1=CC=C2S(=O)(=O)C3=CC=CC=C3C2=C1 IKJFYINYNJYDTA-UHFFFAOYSA-N 0.000 claims description 2
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 claims description 2
- QMLGNDFKJAFKGZ-UHFFFAOYSA-N dicyclohexano-24-crown-8 Chemical compound O1CCOCCOCCOC2CCCCC2OCCOCCOCCOC2CCCCC21 QMLGNDFKJAFKGZ-UHFFFAOYSA-N 0.000 claims description 2
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims description 2
- KYPIULIVYSQNNT-UHFFFAOYSA-N prop-2-enylsulfonylbenzene Chemical compound C=CCS(=O)(=O)C1=CC=CC=C1 KYPIULIVYSQNNT-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- IEIADDVJUYQKAZ-UHFFFAOYSA-N 1,8-naphthosultone Chemical compound C1=CC(S(=O)(=O)O2)=C3C2=CC=CC3=C1 IEIADDVJUYQKAZ-UHFFFAOYSA-N 0.000 claims 3
- NCYNKWQXFADUOZ-UHFFFAOYSA-N 1,1-dioxo-2,1$l^{6}-benzoxathiol-3-one Chemical compound C1=CC=C2C(=O)OS(=O)(=O)C2=C1 NCYNKWQXFADUOZ-UHFFFAOYSA-N 0.000 claims 1
- LOURZMYQPMDBSR-UHFFFAOYSA-N 1,3,2-dioxathiane 2-oxide Chemical compound O=S1OCCCO1 LOURZMYQPMDBSR-UHFFFAOYSA-N 0.000 claims 1
- WVHMPQKZPHOCRD-UHFFFAOYSA-N 2,4,5,6-tetrafluorobenzene-1,3-dicarbonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(C#N)=C1F WVHMPQKZPHOCRD-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000006229 carbon black Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 description 88
- 230000032683 aging Effects 0.000 description 40
- 230000014759 maintenance of location Effects 0.000 description 20
- 239000004830 Super Glue Substances 0.000 description 14
- 229910001220 stainless steel Inorganic materials 0.000 description 11
- 239000010935 stainless steel Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 239000006057 Non-nutritive feed additive Substances 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical class OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 239000013068 control sample Substances 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 229920000800 acrylic rubber Polymers 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- OFLRJMBSWDXSPG-UHFFFAOYSA-N 3,4,5,6-tetrafluorobenzene-1,2-dicarbonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(C#N)=C1F OFLRJMBSWDXSPG-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JJJFUHOGVZWXNQ-UHFFFAOYSA-N enbucrilate Chemical class CCCCOC(=O)C(=C)C#N JJJFUHOGVZWXNQ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006647 (C3-C15) cycloalkyl group Chemical group 0.000 description 1
- OGBWMWKMTUSNKE-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CCCCCC(OC(=O)C(C)=C)OC(=O)C(C)=C OGBWMWKMTUSNKE-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
- IGKCQDUYZULGBM-UHFFFAOYSA-N 2,2,2-trifluoroethyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCC(F)(F)F)C=C1 IGKCQDUYZULGBM-UHFFFAOYSA-N 0.000 description 1
- YXWJGZQOGXGSSC-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(F)=C1F YXWJGZQOGXGSSC-UHFFFAOYSA-N 0.000 description 1
- RJXOVESYJFXCGI-UHFFFAOYSA-N 2,4-difluoro-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1F RJXOVESYJFXCGI-UHFFFAOYSA-N 0.000 description 1
- VTULJCFJIIAAIS-UHFFFAOYSA-N 2-(2-sulfobenzoyl)oxycarbonylbenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1S(O)(=O)=O VTULJCFJIIAAIS-UHFFFAOYSA-N 0.000 description 1
- GXBZQHWSOAJTLZ-UHFFFAOYSA-N 2-chloro-3,5-dinitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=C(Cl)C([N+]([O-])=O)=C1 GXBZQHWSOAJTLZ-UHFFFAOYSA-N 0.000 description 1
- JYTXVMYBYRTJTI-UHFFFAOYSA-N 2-methoxyethyl 2-cyanoprop-2-enoate Chemical compound COCCOC(=O)C(=C)C#N JYTXVMYBYRTJTI-UHFFFAOYSA-N 0.000 description 1
- CFEMBVVZPUEPPP-UHFFFAOYSA-N 2-methylbuta-1,3-diene;prop-2-enenitrile Chemical compound C=CC#N.CC(=C)C=C CFEMBVVZPUEPPP-UHFFFAOYSA-N 0.000 description 1
- IFGHEEXVAVTLKH-UHFFFAOYSA-N 3,3-dicyanoprop-2-enoic acid Chemical compound OC(=O)C=C(C#N)C#N IFGHEEXVAVTLKH-UHFFFAOYSA-N 0.000 description 1
- SSDNULNTQAUNFQ-UHFFFAOYSA-N 3,5-dinitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=CC([N+]([O-])=O)=C1 SSDNULNTQAUNFQ-UHFFFAOYSA-N 0.000 description 1
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 125000006538 C11 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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Images
Classifications
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C—CHEMISTRY; METALLURGY
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C09J11/06—Non-macromolecular additives organic
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- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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- 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
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
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- C09J123/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C09J123/0869—Acids or derivatives thereof
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- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- C09J133/08—Homopolymers or copolymers of acrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- C09J2433/00—Presence of (meth)acrylic polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1519651.2A GB2544272B (en) | 2015-11-06 | 2015-11-06 | Cyanoacrylate compositions |
| GB1519651.2 | 2015-11-06 | ||
| PCT/EP2016/076753 WO2017077091A1 (en) | 2015-11-06 | 2016-11-04 | Cyanoacrylate compositions |
Publications (2)
| Publication Number | Publication Date |
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| BR112018008819A2 BR112018008819A2 (pt) | 2018-10-30 |
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| JP (1) | JP6794460B2 (https=) |
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| BR (1) | BR112018008819B1 (https=) |
| GB (1) | GB2544272B (https=) |
| WO (1) | WO2017077091A1 (https=) |
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| GB2544101B (en) * | 2015-11-06 | 2020-07-15 | Henkel IP & Holding GmbH | Rubber toughened cyanoacrylate compositions and uses thereof |
| GB2562107B (en) * | 2017-05-05 | 2021-08-11 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| GB2567867B (en) * | 2017-10-27 | 2020-09-16 | Henkel IP & Holding GmbH | Toughened, low odor/low bloom cyanoacrylate compositions |
| GB2567868B (en) * | 2017-10-27 | 2020-05-06 | Henkel IP & Holding GmbH | Toughened low odour cyanoacrylate compositions |
| GB2567869B (en) * | 2017-10-27 | 2021-08-11 | Henkel IP & Holding GmbH | Toughened humidity/thermal resistant cyanoacrylate compositions |
| GB2576704B (en) * | 2018-08-16 | 2022-01-12 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
| GB2596355B (en) * | 2020-06-26 | 2022-09-28 | Henkel Ag & Co Kgaa | Cyanoacrylate compositions |
| KR102237285B1 (ko) * | 2021-01-29 | 2021-04-07 | 이혜경 | 안전성이 개선된 미용 접착제 조성물 및 이의 제조방법 |
| EP4194523A1 (en) | 2021-12-07 | 2023-06-14 | Cuantum Medical Cosmetics, S.L. | Cyanoacrylate adhesive composition |
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| IE34874B1 (en) | 1971-01-13 | 1975-09-03 | Intercontinental Chem Co Ltd | Cyanoacrylate adhesive compositions |
| US4196271A (en) | 1975-12-24 | 1980-04-01 | Toagosei Chemical Industry Co., Ltd. | Adhesive composition |
| IE51863B1 (en) | 1980-08-28 | 1987-04-15 | Loctite Corp | Additive for cyanoacrylate adhesives |
| US4490515A (en) * | 1981-06-01 | 1984-12-25 | Loctite Corporation | Hot strength cyanoacrylate adhesive composition |
| US4440910A (en) | 1982-01-18 | 1984-04-03 | Loctite Corporation | Toughened cyanoacrylates containing elastomeric rubbers |
| JPS59147067A (ja) | 1983-02-09 | 1984-08-23 | Alpha Giken:Kk | α−シアノアクリレ−ト系耐熱性瞬間接着剤組成物 |
| US4906317A (en) | 1983-11-10 | 1990-03-06 | Loctite Corporation | Instant adhesive composition and bonding method employing same |
| US4622414A (en) | 1984-01-27 | 1986-11-11 | Loctite Limited | Novel calixarene compounds |
| US4718966A (en) | 1984-01-30 | 1988-01-12 | Loctite (Ireland) Ltd. | Bonding method utilizing cyanoacrylate adhesive having calixarene accelerator |
| US4695615A (en) | 1984-11-21 | 1987-09-22 | Loctite (Ireland) Limited | Instant adhesive composition utilizing mixed functionality calixarenes as accelerators |
| US4636539A (en) | 1984-01-30 | 1987-01-13 | Loctite (Ireland) Limited | Instant adhesive composition utilizing calixarene accelerators |
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| DE4009621A1 (de) | 1990-03-26 | 1991-10-02 | Henkel Kgaa | (alpha) -cyanacrylatklebstoffzusammensetzungen |
| US5328944A (en) * | 1992-07-14 | 1994-07-12 | Loctite Corporation | Cyanoacrylate adhesives with improved cured thermal properties |
| US5424343A (en) | 1992-10-08 | 1995-06-13 | Loctite Corporation | Thermally resistant cyanoacrylates employing substituted napthasultone additive |
| US5288794A (en) | 1992-10-23 | 1994-02-22 | Loctite Corporation | Cyanoacrylate adhesives with improved cured thermal properties utilizing substituted aromatic additive |
| JP2776178B2 (ja) | 1992-11-09 | 1998-07-16 | 東亞合成株式会社 | シアノアクリレート系接着剤組成物 |
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| TW359683B (en) | 1993-12-23 | 1999-06-01 | Loctite Ireland Ltd | Sterilized cyanoacrylate adhesive composition, and a method of making such composition |
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| IES990974A2 (en) * | 1998-11-23 | 2000-05-31 | Loctite R & D Ltd | Cyanoacrylate Compositions |
| DE19938841A1 (de) * | 1999-08-17 | 2001-02-22 | Basf Ag | Inhibitorkomposition zur Stabilisierung von radikalisch polymerisierbaren Substanzen |
| JP5296538B2 (ja) * | 2005-07-11 | 2013-09-25 | ヘンケル コーポレイション | 強靭化シアノアクリレート組成物 |
| US9249237B2 (en) * | 2008-02-15 | 2016-02-02 | Catalyse | Self-repairing composition, self-repairing materials, self-repairing methods and applications |
| US8287687B1 (en) * | 2008-10-22 | 2012-10-16 | Henkel Corporation | Cyanoacrylate compositions incorporating organic micropulp |
| WO2013011421A1 (en) * | 2011-07-15 | 2013-01-24 | Henkel Ireland Limited | Cyanoacrylate compositions |
| JP6190823B2 (ja) * | 2012-01-23 | 2017-08-30 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | 二液型シアノアクリレート/フリーラジカル硬化性接着剤システム |
| US9783714B2 (en) * | 2013-03-15 | 2017-10-10 | Henkel IP & Holding GmbH | Cyanoacrylate compositions |
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2015
- 2015-11-06 GB GB1519651.2A patent/GB2544272B/en active Active
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2016
- 2016-11-04 KR KR1020187013233A patent/KR102593346B1/ko active Active
- 2016-11-04 EP EP16791593.3A patent/EP3371269A1/en active Pending
- 2016-11-04 JP JP2018541561A patent/JP6794460B2/ja active Active
- 2016-11-04 CN CN201680077661.1A patent/CN108473821B/zh active Active
- 2016-11-04 WO PCT/EP2016/076753 patent/WO2017077091A1/en not_active Ceased
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|---|---|
| US11015088B2 (en) | 2021-05-25 |
| GB2544272B (en) | 2020-02-19 |
| JP6794460B2 (ja) | 2020-12-02 |
| KR20180081518A (ko) | 2018-07-16 |
| EP3371269A1 (en) | 2018-09-12 |
| GB2544272A (en) | 2017-05-17 |
| KR102593346B1 (ko) | 2023-10-25 |
| BR112018008819A2 (pt) | 2018-10-30 |
| US20180251659A1 (en) | 2018-09-06 |
| JP2019500484A (ja) | 2019-01-10 |
| CN108473821B (zh) | 2021-01-26 |
| WO2017077091A1 (en) | 2017-05-11 |
| GB201519651D0 (en) | 2015-12-23 |
| CN108473821A (zh) | 2018-08-31 |
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Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 04/11/2016, OBSERVADAS AS CONDICOES LEGAIS |
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| B25A | Requested transfer of rights approved |
Owner name: HENKEL AG AND CO. KGAA (DE) |