JP2783847B2 - Curable compositions, their production and use - Google Patents
Curable compositions, their production and useInfo
- Publication number
- JP2783847B2 JP2783847B2 JP1167142A JP16714289A JP2783847B2 JP 2783847 B2 JP2783847 B2 JP 2783847B2 JP 1167142 A JP1167142 A JP 1167142A JP 16714289 A JP16714289 A JP 16714289A JP 2783847 B2 JP2783847 B2 JP 2783847B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- component
- composition
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000002685 polymerization catalyst Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 4
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000004576 sand Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000004982 aromatic amines Chemical class 0.000 description 7
- 150000002432 hydroperoxides Chemical class 0.000 description 6
- 150000001451 organic peroxides Chemical class 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- -1 hydrocarbyl hydroperoxide Chemical compound 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- HYZQBNDRDQEWAN-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese(3+) Chemical compound [Mn+3].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O HYZQBNDRDQEWAN-LNTINUHCSA-N 0.000 description 1
- ZPOUDMYDJJMHOO-UHFFFAOYSA-N 1-(1-hydroxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(O)CCCCC1 ZPOUDMYDJJMHOO-UHFFFAOYSA-N 0.000 description 1
- CCWAZSSURXWVEA-UHFFFAOYSA-N 1-[3-(1-hydroxycyclohexyl)butan-2-yl]cyclohexan-1-ol Chemical compound OC1(CCCCC1)C(C)C(C)C1(CCCCC1)O CCWAZSSURXWVEA-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- FDVMTFQUDUTFBZ-UHFFFAOYSA-N 1-tert-butyl-4-(4-tert-butylcyclohexyl)peroxycyclohexane;carboxy hydrogen carbonate Chemical compound OC(=O)OC(O)=O.C1CC(C(C)(C)C)CCC1OOC1CCC(C(C)(C)C)CC1 FDVMTFQUDUTFBZ-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- DGPBVJWCIDNDPN-UHFFFAOYSA-N 2-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=CC=C1C=O DGPBVJWCIDNDPN-UHFFFAOYSA-N 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 240000007695 Nandina domestica Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000012615 aggregate Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- UKRVECBFDMVBPU-UHFFFAOYSA-N ethyl 3-oxoheptanoate Chemical compound CCCCC(=O)CC(=O)OCC UKRVECBFDMVBPU-UHFFFAOYSA-N 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000010438 granite Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910021487 silica fume Inorganic materials 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/02—Macromolecular compounds
- C04B26/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/02—Macromolecular compounds
- C04B26/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B26/06—Acrylates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Engineering & Computer Science (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Working Measures On Existing Buildindgs (AREA)
- Aftertreatments Of Artificial And Natural Stones (AREA)
- Paints Or Removers (AREA)
- Polymerization Catalysts (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
【発明の詳細な説明】 本発明によれば、ａ）式Ｉ 式中、 Ｒは水素またはメチルであり、 R1は直鎖状もしくは分枝鎖状のC2−C8アルキレンであ
り、 ｎは１であり、 R2は式ａ）の基であり、 式中、 R3は直鎖状もしくは分枝鎖状のC1−C22アルキル基で
ある、 の化合物（以後、成分ａと呼ぶ）の１種または２種以
上、および ｂ）必要に応じて、式Ｉ以外のビニル化合物（以後、成
分ｂと呼ぶ）の１種または２種以上、および ｃ）0.1〜10％（成分ａおよびｂの重量に基づく）の２
種またはそれ以上の重合触媒（以後、成分ｃと呼ぶ）、
すべての百分率は組成物の重量に基づく、 からなる組成物が提供される。DETAILED DESCRIPTION OF THE INVENTION According to the present invention, a) Formula I Wherein R is hydrogen or methyl, R 1 is a linear or branched C 2 -C 8 alkylene, n is 1 and R 2 is a group of formula a) Wherein R 3 is a linear or branched C 1 -C 22 alkyl group, one or more of the following compounds (hereinafter referred to as component a): and b) optionally One or more vinyl compounds other than formula I (hereinafter referred to as component b), and c) 0.1-10% (based on the weight of components a and b)
One or more polymerization catalysts (hereinafter referred to as component c),
A composition is provided, wherein all percentages are based on the weight of the composition.
好ましくは、モノマーの合計重量に基づいて20〜10
0、より好ましくは50〜95％の成分ａおよび０〜80、よ
り好ましくは５〜50％の成分ｂが本発明による組成物中
に存在する。Preferably, 20 to 10 based on the total weight of the monomers
0, more preferably 50-95% of component a and 0-80, more preferably 5-50% of component b are present in the composition according to the invention.
本発明による組成物は、好ましくは、 ｄ）組成物の合計重量に基づいて40〜95％の無機骨材
（以後、成分ｄと呼ぶ）を含有する。The compositions according to the invention preferably contain d) 40-95% of inorganic aggregates (hereinafter component d), based on the total weight of the composition.
重合触媒（成分ｃ）、例えば、有機ヒドロペルオキシ
ドおよび芳香族アミン促進剤および必要に応じて多価金
属塩または錯塩を、適用前に、モノマー混合物に添加す
ることができる。適用前に組成物に添加する金属塩また
は錯塩の比率は0.0005重量％から約２重量％までであ
り、そしてヒドロペルオキシドの量は、モノマーの合計
重量に基づいて、0.1〜５重量％である。同様に、有機
ペルオキシドを、芳香族アミン促進剤とともに、および
必要に応じて多価金属塩または錯塩とともに、適用前
に、混合物に添加することができる。組成物に対する有
機ペルオキシドの比率は0.5〜５重量％の範囲であるこ
とができ、そして芳香族アミン促進剤は有効量で、通常
約0.1〜５重量％の範囲で使用する。The polymerization catalyst (component c), for example an organic hydroperoxide and an aromatic amine promoter and optionally a polyvalent metal salt or complex, can be added to the monomer mixture before application. The proportion of metal salt or complex salt added to the composition before application is from 0.0005% to about 2% by weight, and the amount of hydroperoxide is from 0.1 to 5% by weight, based on the total weight of the monomers. Similarly, the organic peroxide can be added to the mixture with the aromatic amine promoter and, optionally, with the polyvalent metal salt or complex before application. The ratio of organic peroxide to the composition can range from 0.5 to 5% by weight, and the aromatic amine promoter is used in an effective amount, usually in the range of about 0.1 to 5% by weight.
重合触媒の成分、例えば、多価金属塩または錯塩およ
びヒドロペルオキシド、およびアミン促進剤または芳香
族アミン促進剤およびペルオキシドは別々に包装し、そ
して作業場所に運搬し、そこでそれぞれの成分を一緒に
し、そしてそこで本発明の組成物を、例えば、注入また
は噴霧して、コンクリートの床または基礎または舗装に
含浸または密封することによって適用することができ
る。あるいは、それぞれ、芳香族アミン促進剤およびバ
インダーのモノマー系、および有機ペルオキシド（必要
に応じて骨剤と一緒に）は、包装で一緒にして、貯蔵お
よび運搬して、それらを一緒にして本発明の組成物を形
成した後、この組成物を適用する。The components of the polymerization catalyst, such as polyvalent metal salts or complex salts and hydroperoxides, and amine or aromatic amine promoters and peroxides are separately packaged and transported to a work place where the respective components are combined, The compositions of the invention can then be applied, for example, by pouring or spraying, impregnating or sealing concrete floors or foundations or pavements. Alternatively, the monomer system of the aromatic amine promoter and binder, and the organic peroxide, together with the bone aggregate, respectively, are packaged together, stored and transported, and brought together to form the invention. After forming the composition, the composition is applied.
本発明において使用する多価金属塩または錯塩は、乾
性油の酸化的硬化を触媒しそして、油性ワニスおよび塗
料に添加したとき、それらの乾燥または硬化を促進、任
意の多価金属含有塩であることができる。これらの金属
塩または錯塩は、また、この分野において、「ドライヤ
ー（siccativeまたはdryer）」として知られている。こ
のような物質は、バインダーモノマー系中の溶解性を提
供する、８〜30個の炭素原子を有する高級脂肪族または
ナンテン系酸の多価金属塩類を包含する。一般に、本発
明の組成物に最も有用なドライヤー塩類は、ナンテン酸
またはC8−C30脂肪族酸の塩類である。多価金属の例
は、カルシウム、銅II、亜鉛II、マンガンII、マンガン
III、鉛II、コバルトII、鉄III、バナジンIIおよびジル
コニウムIVを包含する。これらの塩類または錯塩類は、
有機ヒドロペルオキシドの作用を加速し、そして有機ペ
ルオキシド−アミン触媒系における酸化的硬化を促進す
る。ドライヤー塩の酸成分またはアニオンの他の例は、
樹脂酸、２−エチルヘキサン酸、ラウリン酸、パルミチ
ン酸、ミリスチン酸、ステアリン酸、オレイン酸、リノ
ール酸、ベヘン酸、セロチン酸、モノタン酸（monotani
c acid）およびアビエチン酸のそれらである。The polyvalent metal salt or complex salt used in the present invention is any polyvalent metal-containing salt that catalyzes the oxidative curing of drying oils and promotes their drying or curing when added to oily varnishes and paints. be able to. These metal or complex salts are also known in the art as "siccative or dryer". Such materials include higher aliphatic or nanthenic acid polyvalent metal salts having from 8 to 30 carbon atoms that provide solubility in the binder monomer system. Generally, the most useful drier salts in the compositions of the present invention are salts of Nandina acid or C 8 -C 30 aliphatic acid. Examples of polyvalent metals are calcium, copper II, zinc II, manganese II, manganese
III, lead II, cobalt II, iron III, vanadin II and zirconium IV. These salts or complex salts are
It accelerates the action of organic hydroperoxides and promotes oxidative curing in organic peroxide-amine catalyst systems. Other examples of the acid component or anion of the dryer salt are:
Resin acid, 2-ethylhexanoic acid, lauric acid, palmitic acid, myristic acid, stearic acid, oleic acid, linoleic acid, behenic acid, serotinic acid, monotanic acid
c acid) and abietic acid.
好ましくはドライヤー塩類は、コバルトおよびマンガ
ンのそれら、例えば、オクタン酸コバルト、ナフテン酸
コバルト、コバルトアセチルアセトネートおよびオクタ
ン酸マンガン、ナフテン酸マンガン、およびマンガンア
セチルアセトネートである。Preferably the dryer salts are those of cobalt and manganese, such as cobalt octoate, cobalt naphthenate, cobalt acetylacetonate and manganese octoate, manganese naphthenate, and manganese acetylacetonate.
芳香族アミンは、少量で、有機ペルオキシドとともに
使用し、そして一般にペルオキシドの作用を加速する。
例えば、アニリン、N,N−ジメチルアニリン、N,N−ジエ
チルアニリン、トルイジン、N,N−ジメチルｐ−トルイ
ジン、N,N−ジ（ヒドロキシエチル）トルイジン、およ
びｐ−ジメチルアミノベンズアルデヒドを、この目的
に、バインダーモノマー系の0.1〜２重量％の量で添加
することができる。Aromatic amines are used in small amounts with organic peroxides and generally accelerate the action of the peroxide.
For example, aniline, N, N-dimethylaniline, N, N-diethylaniline, toluidine, N, N-dimethyl p-toluidine, N, N-di (hydroxyethyl) toluidine, and p-dimethylaminobenzaldehyde for this purpose Can be added in an amount of 0.1 to 2% by weight of the binder monomer system.
使用できる有機ペルオキシドおよびヒドロペルオキシ
ドは、バインダーモノマー系中に可溶性であるように、
約３〜18個の炭素原子を有する炭化水素から誘導され
る、ペルオキシドおよびヒドロペルオキシドを包含す
る。適当な有機ヒドロペルオキシドは、tert−ブチルヒ
ドロペルオキシド、クメンヒドロペルオキシド、メチル
エチルケトンとヒドロペルオキシドおよびジイソプロピ
ルベンゼンヒドロペルオキシドを包含する。適当なペル
オキシドは、ベンゾイルペルオキシド、tert−ブチルペ
ルベンゾエート、ジラウリルペルオキシド、ジ−（４−
tert−ブチル−シクロヘキシル）−ペルオキシドジカー
ボネート、2,2−ビス（tert−ブチルペルオキシ）−ブ
タン、ビス−（１−ヒドロキシ−シクロヘキシル）−ブ
タン、ビス−（１−ヒドロキシ−シクロヘキシル）−ペ
ルオキシド、およびtert−ブチルペルオキシ−イソプロ
ピルカーボネートを包含する。The organic and hydroperoxides that can be used are such that they are soluble in the binder monomer system.
Includes peroxides and hydroperoxides derived from hydrocarbons having about 3 to 18 carbon atoms. Suitable organic hydroperoxides include tert-butyl hydroperoxide, cumene hydroperoxide, methyl ethyl ketone and hydroperoxide and diisopropylbenzene hydroperoxide. Suitable peroxides are benzoyl peroxide, tert-butyl perbenzoate, dilauryl peroxide, di- (4-
tert-butyl-cyclohexyl) -peroxide dicarbonate, 2,2-bis (tert-butylperoxy) -butane, bis- (1-hydroxy-cyclohexyl) -butane, bis- (1-hydroxy-cyclohexyl) -peroxide, and tert-butyl peroxy-isopropyl carbonate.
好ましい重合触媒は、有機ペルオキシドおよび芳香族
アミンの混合物である。より好ましい重合触媒は、ベン
ゾイルペルオキシドまたはクメンペルオキシドおよびN,
N−ジメチルｐ−トルイジンの混合物である。ことに好
ましい重合触媒は、ｐ−ジメチルアミノベンズアルデヒ
ド、ベンゾイルペルオキシドまたはクメンペルオキシド
およびナフテン酸コバルトの混合物である。Preferred polymerization catalysts are mixtures of organic peroxides and aromatic amines. More preferred polymerization catalysts are benzoyl peroxide or cumene peroxide and N,
It is a mixture of N-dimethyl p-toluidine. Particularly preferred polymerization catalysts are p-dimethylaminobenzaldehyde, benzoyl peroxide or a mixture of cumene peroxide and cobalt naphthenate.
ここにおいて必要に応じて使用する骨材（成分ｄ）
は、普通の工業プラントにおいて直面することがある、
有機酸および無機酸、塩およびアルカリ、例えば、塩
酸、硫酸、硝酸、スルホン酸、リン酸、酢酸、ギ酸；ナ
トリウム、カリウム、カルシウムおよびマンガンの塩
類、例えば、塩化物、硫酸塩およびアルカリ金属および
アルカリ土類金属の水酸化物に対して抵抗性の不活性の
無機材料であることができる。適当な骨材の例は、砂、
シリカ粉末、石英、花崗岩、長石、片麻岩、玄武岩、班
岩の岩石または石の粉砕物およびそれらの小さい石を包
含する。使用できる砂は、任意の品質または大きさであ
ることができる。中程度の粒子サイズの等級づけられた
砂、例えば、「オッタワ（ottawa）」砂および「ベスト
（Best）」砂またはそれらの混合物は、より有利に使用
することができる。オッタワ砂は「丸い（round）」と
呼ばれるタイプのシリカ砂である。ベスト砂は「シャー
プ（sharp）」として知られているタイプである。両者
の場合において、微細物は除去されてあるであろう。し
かしながら、一般に、砂の篩の大きさはかなり広い範囲
にわたって変化することができる。砂の代わりにまたは
それに加えて、粉砕した着色ガラスのビー玉、ガラス粉
砕物、シリカ粉末、エメリー粉末、スラグ粉砕物、およ
び微細な砂利を使用することができる。Aggregate used here if necessary (component d)
May be encountered in ordinary industrial plants,
Organic and inorganic acids, salts and alkalis, such as hydrochloric acid, sulfuric acid, nitric acid, sulfonic acid, phosphoric acid, acetic acid, formic acid; salts of sodium, potassium, calcium and manganese, such as chlorides, sulfates and alkali metals and alkalis It can be an inert inorganic material that is resistant to earth metal hydroxides. Examples of suitable aggregates are sand,
Includes silica powder, quartz, granite, feldspar, gneiss, basalt, gangue rock or crushed stone and small stones thereof. The sand that can be used can be of any quality or size. Graded sands of medium particle size, such as "ottawa" sand and "Best" sand or mixtures thereof, can be used more advantageously. Ottawa sand is a type of silica sand called "round." Vest sand is a type known as "sharp". In both cases, the fines will have been removed. However, in general, the size of the sand sieve can vary over a fairly wide range. Instead of or in addition to sand, ground colored glass marbles, glass grind, silica powder, emery powder, slag grind, and fine gravel can be used.
さらに、本発明によれば、一緒に使用するために適合
する、３つのパッケージ組成物、 成分ａおよびｂからなる第１パッケージ、 成分ｃからなる第２パッケージおよび 成分ｄからなる第３パッケージ、 が提供される。Furthermore, according to the present invention, there are three package compositions adapted for use together, a first package consisting of components a and b, a second package consisting of component c and a third package consisting of component d. Provided.
第２および第３パッケージは、一緒にすることが出来
るか、あるいは第１および第３パッケージを一緒にする
ことができる。The second and third packages can be combined, or the first and third packages can be combined.
好ましくは、R1はR1′であり、ここでR1′は、−CH2
−CH2−； である。Preferably, R 1 is R 1 ′, where R 1 ′ is —CH 2
—CH 2 —; It is.
好ましくは、R2はR2′であり、ここでR2′は式ａ′ 式中、R3′直鎖状もしくは分枝鎖状のC1-12アルキル
基である、 の基である。Preferably, R 2 is R 2 ′, where R 2 ′ is of the formula a ′ In the formula, R 3 ′ is a linear or branched C 1-12 alkyl group.
好ましくは、本発明による組成物において、式Ｉの化
合物は、式II 式中、記号は上に定義した通りである、 の化合物である。Preferably, in the composition according to the invention, the compound of the formula I is of the formula II Wherein the symbols are as defined above.
好ましくは、成分ｃは0.1〜５重量％のC3−C18ヒドロ
カルビルペルオキシドまたはC3−C18ヒドロカルビルヒ
ドロペルオキシドおよび0.005〜２重量％の多価金属塩
または錯塩および／または0.1〜５％の芳香族アミノ基
含有ポリマーの促進剤の組み合わせであり、すべて百分
率は成分ａおよびｂの重量に基づく。Preferably, component c is 0.1 to 5% by weight of C 3 -C 18 hydrocarbyl hydroperoxide or C 3 -C 18 hydrocarbyl hydroperoxide and 0.005 wt% of a multivalent metal salt or complex and / or 0.1 to 5% of the aromatic Combination of accelerators of group amino group containing polymers, all percentages are based on the weight of components a and b.
R2が式ａ）の基である式Ｉの化合物は、 ｉ） １モルの式Ｌ の１つの無水物を、１モルの式XVI R3−OH （XVI） の化合物と、高温において、反応させて、式XVII OH−R2 （XVII） の化合物を生成し、次いで ii） １モルの式XVIIの化合物を、１モルの式XIX HO−（R1−Ｏ）ｎ−Ｈ （XIX） の化合物と、高温において、反応させて、式XXI R2−Ｏ−（R1−Ｏ）ｎ−Ｈ （XXI） 式中、R2は上に定義した通りである、 の化合物を生成し、次いで iii） １モルの式XXIの化合物を１モルの式XXII の化合物と、高温において、反応させて式Ｉの化合物を
生成する、 ことにより、生成することができる。Compounds of the formula I in which R 2 is a group of the formula a) include: i) 1 mole of the formula L One anhydride of a compound of one mole of the formula XVI R 3 -OH (XVI), at elevated temperatures, is reacted to produce a compound of formula XVII OH-R 2 (XVII) , followed by ii) 1 mole Is reacted with 1 mol of a compound of the formula XIX HO- (R 1 -O) n -H (XIX) at elevated temperature to give a compound of the formula XXI R 2 -O- (R 1 -O) in n -H (XXI) formula, R 2 generates a are as defined above, the compound and then iii) 1 mole of the compound 1 mole of formula XXII of formula XXI With a compound of formula I at elevated temperature to form a compound of formula I.
上の反応において、高温は40〜110℃の温度を意味す
る。In the above reaction, elevated temperature means a temperature of 40-110 ° C.
成分ａ〔必要に応じて成分〕、ｃおよびｄを含有する
本発明による組成物は、コンクリート材料または表面の
補修に有用である。このような組成物は、補修を必要と
する表面に適用し、そして周囲温度において硬化させ
る。The compositions according to the invention, comprising components a (optionally components), c and d, are useful for concrete material or surface repair. Such a composition is applied to the surface in need of repair and cured at ambient temperature.
本発明による組成物または化合物は、単独であるいは
充填材と一緒に、使用して、多孔質材料、ことにコンク
リートを含浸および／または被覆すること、例えば、割
れ目を充填することができる。The compositions or compounds according to the invention can be used alone or with fillers to impregnate and / or coat porous materials, especially concrete, for example to fill cracks.
実施例１および２ １モルのフタル酸無水物を１モルのメタクリル酸グリ
コールエステルと、約100℃の温度において反応させ
て、式1a の中間体を生成する。Examples 1 and 2 One mole of phthalic anhydride was reacted with one mole of glycol methacrylate at a temperature of about 100 ° C to give a compound of formula 1a To produce an intermediate.
式1aの化合物を水酸化ナトリウムで中和し、そして40
℃において0.5モルの硫酸ジメチルと反応させる。下に
定義する式１の化合物は液体であり、粘度はブルックフ
ィールド粘度計、スピンドル２で60rpmで測定し、下表
に記載する。類似の方法により、さらに式１（式中、記
号は表に定義するとおりである）の化合物を適当な反応
成分から得ることができる。Neutralizing a compound of formula 1 a with sodium hydroxide, and 40
React with 0.5 mol of dimethyl sulfate at 0 ° C. The compound of formula 1 as defined below is a liquid and the viscosity is measured on a Brookfield viscometer, spindle 2 at 60 rpm and is listed in the table below. In a similar manner, compounds of formula 1 (wherein the symbols are as defined in the table) can be obtained from the appropriate reaction components.
適用例 実施例１の化合物および式1aの中間体を骨材および触
媒と、次の処方に従い混合する。 Compounds of applications Example 1 and the intermediates of formula 1 a is mixed with aggregate and the catalyst according to the following formulation.
砂 229.2 g シリカヒューム 23.2 g 実施例１の式１の化合物 42.75g 式1aの化合物 2.25g ジメチルアミノベンズアルデヒド 1.8 g クメンヒドロペルオキシド 0.9 g ナフテン酸コバルト 0.9 g 300 ｇ この組成物は15分以内で硬化し、そして12時間後、強
度について試験することができる。建築場所に発送する
ため、骨材、モノマーおよび触媒を異なるパッケージに
包装する。Sand 229.2 g silica fume 23.2 g Compound 42.75g Formula 1 a compound 2.25g dimethylaminobenzaldehyde 1.8 g cumene hydroperoxide 0.9 g cobalt naphthenate 0.9 g 300 g The composition of formula 1 of Example 1 cured within 15 minutes And after 12 hours, can be tested for strength. The aggregate, monomer and catalyst are packaged in different packages for shipping to the building site.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｅ０４Ｇ 23/02 Ｅ０４Ｇ 23/02 Ｂ (58)調査した分野(Int.Cl.6，ＤＢ名) C08F 20/00 - 20/40 C08F 120/00 - 120/40 C08F 220/00 - 220/40 C08F 2/44 C08L 33/00 - 33/16──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 6 identification code FI E04G 23/02 E04G 23/02 B (58) Field surveyed (Int.Cl. 6 , DB name) C08F 20/00-20 / 40 C08F 120/00-120/40 C08F 220/00-220/40 C08F 2/44 C08L 33/00-33/16
Claims (6)
り、 R2は式ａ）の基であり、 式中、 R3は直鎖状もしくは分枝鎖状のC1−C22アルキル基であ
る、 の化合物（以後、成分ａと呼ぶ）の１種または２種以
上、および ｂ）必要に応じて、式Ｉ以外のビニル化合物（以後、成
分ｂと呼ぶ）の１種または２種以上、および ｃ）0.1〜10％（成分ａおよびｂの重量に基づく）の２
種またはそれ以上の重合触媒（以後、成分ｃと呼ぶ）、
すべての百分率は組成物の重量に基づく、 からなることを特徴とする組成物。1. A) Formula I Wherein R is hydrogen or methyl; R 1 is linear or branched C 2 -C 8 alkylene; R 2 is a group of formula a) Wherein R 3 is a linear or branched C 1 -C 22 alkyl group, one or more of the following compounds (hereinafter referred to as component a): and b) optionally One or more vinyl compounds other than formula I (hereinafter referred to as component b), and c) 0.1-10% (based on the weight of components a and b)
One or more polymerization catalysts (hereinafter referred to as component c),
A composition, wherein all percentages are based on the weight of the composition.
ｂを含有する上記第１項記載の組成物。2. The composition according to claim 1, which contains 20 to 100% of component a and 0 to 80% of component b.
機骨材を含有する上記第１または２項記載の組成物。3. A composition according to claim 1, which contains from 40 to 95% of inorganic aggregate, based on the total weight of the composition.
り、そして Ｒは水素またはメチルである、 の化合物である上記第１〜３項のいずれかに記載の組成
物。4. A compound a having the formula II Where: R 2 ′ is a formula a ′ Wherein R 3 ′ is a linear or branched C 1-12 alkyl group, and R is hydrogen or methyl. A composition according to any of the above.
であって、 ｉ）１モルの式Ｌ の無水物を、１モルの式XVI R3−OH （XVI） の化合物と、高温において、反応させて、式XVII HO−R2 （XVII） の化合物を生成し、次いで ii）１モルの式XVIIの化合物を、１モルの式XIX HO−（R1−Ｏ）−Ｈ （XIX） の化合物と、高温において、反応させて、式XXI R2−Ｏ−（R1−Ｏ）−Ｈ （XXI） の化合物を生成し、次いで iii）１モルの式XXIの化合物を１モルの式XXII の化合物と、高温において、反応させることにより式Ｉ
の化合物を調製する、 工程を含むことを特徴とする方法。5. A process for preparing a composition according to claim 1, comprising: i) 1 mole of formula L The anhydride, a compound of one mole of the formula XVI R 3 -OH (XVI), at elevated temperatures, is reacted to produce a compound of formula XVII HO-R 2 (XVII) , followed by ii) one mole of the formula The compound of the formula XVII is reacted with 1 mol of a compound of the formula XIX HO- (R 1 -O) -H (XIX) at elevated temperature to give the compound of the formula XXI R 2 -O- (R 1 -O) -H ( XXI) to produce a compound of the formula XI) With a compound of the formula I
Preparing a compound of the above.
材料または表面に適用することを含む、コンクリート材
料または表面の修復方法。6. A method for repairing a concrete material or surface, comprising applying the composition according to claim 1 to the concrete material or surface.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3822201 | 1988-07-01 | ||
| DE3822201.9 | 1988-07-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0247115A JPH0247115A (en) | 1990-02-16 |
| JP2783847B2 true JP2783847B2 (en) | 1998-08-06 |
Family
ID=6357692
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1167142A Expired - Lifetime JP2783847B2 (en) | 1988-07-01 | 1989-06-30 | Curable compositions, their production and use |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JP2783847B2 (en) |
| AT (1) | AT397383B (en) |
| AU (1) | AU631798B2 (en) |
| BE (1) | BE1004043A3 (en) |
| CA (1) | CA1335508C (en) |
| CH (1) | CH679585A5 (en) |
| DE (1) | DE3920795C2 (en) |
| ES (1) | ES2017025A6 (en) |
| FR (1) | FR2633629B1 (en) |
| GB (1) | GB2220204B (en) |
| HK (1) | HK10595A (en) |
| IT (1) | IT1232153B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5596036A (en) * | 1991-06-14 | 1997-01-21 | Sandoz Ltd. | Hardenable acrylic monomer compositions |
| DE4218414C2 (en) * | 1991-06-14 | 2001-04-05 | Mbt Holding Ag Zuerich | Fast curing monomer preparations and their use |
| US5712337A (en) * | 1992-06-11 | 1998-01-27 | Mbt Holding Ag | Hardenable acrylic monomer compositions |
| DE4242356A1 (en) * | 1992-12-15 | 1994-06-16 | Sandoz Ag | Monomer preparations for the construction industry |
| JPH10148797A (en) * | 1996-11-18 | 1998-06-02 | Menicon Co Ltd | Lens material for eye |
| JPH10206804A (en) * | 1997-01-20 | 1998-08-07 | Menicon Co Ltd | Ocular lens material |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2300370A1 (en) | 1973-01-05 | 1974-07-18 | Basf Ag | UV-curable printing inks with unsatd polyester binder - contg. mono olefinically unsatd comonomer photopolymerisation initiator for rapid cure to flexible film |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336360A (en) * | 1963-12-26 | 1967-08-15 | Monsanto Co | Acrylyloxyalkyl esters of polycarboxylic acids |
| US3367992A (en) * | 1964-06-05 | 1968-02-06 | Dow Chemical Co | 2-hydroxyalkyl acrylate and methacrylate dicarboxylic acid partial esters and the oxyalkylated derivatives thereof |
| NL6917781A (en) * | 1968-12-02 | 1970-06-04 | ||
| US4129545A (en) * | 1976-01-16 | 1978-12-12 | Mitsubishi Rayon Co., Ltd. | Thermosetting acrylic copolymer usable as a powder paint and method for producing the same |
| US4460625A (en) * | 1981-07-16 | 1984-07-17 | Rohm And Haas Company | Method of coating and impregnating concrete substrates, and products obtained thereby |
| AU558942B2 (en) * | 1982-07-03 | 1987-02-12 | Smith & Nephew Associated Companies Plc | Polymerisable compounds |
| JPS59137354A (en) * | 1983-01-20 | 1984-08-07 | 大倉工業株式会社 | Manufacture of plastic concrete |
| JPS62161742A (en) * | 1986-01-08 | 1987-07-17 | Nippon Paint Co Ltd | Terminal carboxyl group-containing reactive acrylic monomer and production thereof |
| AU599946B2 (en) * | 1986-01-08 | 1990-08-02 | Nippon Paint Co., Ltd. | Vinyl resin microparticles and aqueous emulsion containing the same |
| JPH0749986B2 (en) * | 1991-09-05 | 1995-05-31 | 株式会社フォトニクス | Hopper feeder device of vertical precision weighing and feeding device |
-
1989
- 1989-06-24 DE DE3920795A patent/DE3920795C2/en not_active Expired - Lifetime
- 1989-06-26 BE BE8900697A patent/BE1004043A3/en not_active IP Right Cessation
- 1989-06-26 FR FR8908590A patent/FR2633629B1/en not_active Expired - Lifetime
- 1989-06-28 IT IT8948137A patent/IT1232153B/en active
- 1989-06-28 CH CH2403/89A patent/CH679585A5/de not_active IP Right Cessation
- 1989-06-29 GB GB8914922A patent/GB2220204B/en not_active Expired - Lifetime
- 1989-06-29 AT AT0160189A patent/AT397383B/en not_active IP Right Cessation
- 1989-06-29 AU AU37212/89A patent/AU631798B2/en not_active Ceased
- 1989-06-30 ES ES8902329A patent/ES2017025A6/en not_active Expired - Lifetime
- 1989-06-30 JP JP1167142A patent/JP2783847B2/en not_active Expired - Lifetime
- 1989-06-30 CA CA000604627A patent/CA1335508C/en not_active Expired - Fee Related
-
1995
- 1995-01-26 HK HK10595A patent/HK10595A/en not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2300370A1 (en) | 1973-01-05 | 1974-07-18 | Basf Ag | UV-curable printing inks with unsatd polyester binder - contg. mono olefinically unsatd comonomer photopolymerisation initiator for rapid cure to flexible film |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA160189A (en) | 1993-08-15 |
| GB2220204A (en) | 1990-01-04 |
| IT8948137A0 (en) | 1989-06-28 |
| CA1335508C (en) | 1995-05-09 |
| IT1232153B (en) | 1992-01-25 |
| FR2633629B1 (en) | 1993-07-23 |
| AU631798B2 (en) | 1992-12-10 |
| JPH0247115A (en) | 1990-02-16 |
| GB2220204B (en) | 1992-03-11 |
| FR2633629A1 (en) | 1990-01-05 |
| GB8914922D0 (en) | 1989-08-23 |
| BE1004043A3 (en) | 1992-09-15 |
| AT397383B (en) | 1994-03-25 |
| DE3920795C2 (en) | 1999-06-24 |
| CH679585A5 (en) | 1992-03-13 |
| DE3920795A1 (en) | 1990-02-01 |
| AU3721289A (en) | 1990-01-04 |
| ES2017025A6 (en) | 1990-12-16 |
| HK10595A (en) | 1995-02-03 |
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