JPH04142380A - Adhesive plastisol composition - Google Patents
Adhesive plastisol compositionInfo
- Publication number
- JPH04142380A JPH04142380A JP26557590A JP26557590A JPH04142380A JP H04142380 A JPH04142380 A JP H04142380A JP 26557590 A JP26557590 A JP 26557590A JP 26557590 A JP26557590 A JP 26557590A JP H04142380 A JPH04142380 A JP H04142380A
- Authority
- JP
- Japan
- Prior art keywords
- vinyl chloride
- weight
- acid
- units
- vinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 239000000853 adhesive Substances 0.000 title claims description 29
- 230000001070 adhesive effect Effects 0.000 title claims description 29
- 229920001944 Plastisol Polymers 0.000 title claims description 24
- 239000004999 plastisol Substances 0.000 title claims description 24
- 229920001577 copolymer Polymers 0.000 claims abstract description 29
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000004014 plasticizer Substances 0.000 claims abstract description 13
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 10
- 239000011256 inorganic filler Substances 0.000 claims abstract description 9
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims description 15
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- 239000011976 maleic acid Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 13
- 239000002184 metal Substances 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000565 sealant Substances 0.000 abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000002845 discoloration Methods 0.000 abstract description 3
- 238000001879 gelation Methods 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract 2
- 230000005587 bubbling Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- -1 isocyanate compounds Chemical class 0.000 description 48
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 229920001567 vinyl ester resin Polymers 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003945 anionic surfactant Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000007720 emulsion polymerization reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 238000010558 suspension polymerization method Methods 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 150000001451 organic peroxides Chemical class 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 3
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007771 core particle Substances 0.000 description 3
- 238000010556 emulsion polymerization method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 2
- NXQMCAOPTPLPRL-UHFFFAOYSA-N 2-(2-benzoyloxyethoxy)ethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOCCOC(=O)C1=CC=CC=C1 NXQMCAOPTPLPRL-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- WDRCVXGINNJWPH-UHFFFAOYSA-N tris(6-methylheptyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC(C)C)C(C(=O)OCCCCCC(C)C)=C1 WDRCVXGINNJWPH-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- UTOVMEACOLCUCK-SNAWJCMRSA-N (e)-4-butoxy-4-oxobut-2-enoic acid Chemical compound CCCCOC(=O)\C=C\C(O)=O UTOVMEACOLCUCK-SNAWJCMRSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SOSQXPIKTBUEKF-UHFFFAOYSA-N 1,4-dihexoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound CCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCC SOSQXPIKTBUEKF-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- QABUFWQCKDRYGJ-UHFFFAOYSA-N 1-tert-butyl-2-propan-2-ylbenzene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1C(C)(C)C QABUFWQCKDRYGJ-UHFFFAOYSA-N 0.000 description 1
- NEFDVAJLNQFZTD-UHFFFAOYSA-N 2,3-diacetyloxypropyl acetate;propane-1,2,3-triol Chemical class OCC(O)CO.CC(=O)OCC(OC(C)=O)COC(C)=O NEFDVAJLNQFZTD-UHFFFAOYSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- PHDVPEOLXYBNJY-KTKRTIGZSA-N 2-(2-hydroxyethoxy)ethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCOCCO PHDVPEOLXYBNJY-KTKRTIGZSA-N 0.000 description 1
- WGIMXKDCVCTHGW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCCO WGIMXKDCVCTHGW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- ZGHZSTWONPNWHV-UHFFFAOYSA-N 2-(oxiran-2-yl)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCC1CO1 ZGHZSTWONPNWHV-UHFFFAOYSA-N 0.000 description 1
- JEYLQCXBYFQJRO-UHFFFAOYSA-N 2-[2-[2-(2-ethylbutanoyloxy)ethoxy]ethoxy]ethyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OCCOCCOCCOC(=O)C(CC)CC JEYLQCXBYFQJRO-UHFFFAOYSA-N 0.000 description 1
- XFDQLDNQZFOAFK-UHFFFAOYSA-N 2-benzoyloxyethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCOC(=O)C1=CC=CC=C1 XFDQLDNQZFOAFK-UHFFFAOYSA-N 0.000 description 1
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 1
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 1
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
- SGJUFIMCHSLMRJ-UHFFFAOYSA-N 2-hydroperoxypropane Chemical compound CC(C)OO SGJUFIMCHSLMRJ-UHFFFAOYSA-N 0.000 description 1
- ZAYGISOXMIXWHX-UHFFFAOYSA-N 2-methylpropoxycarbonyloxy 2-methylpropyl carbonate Chemical compound CC(C)COC(=O)OOC(=O)OCC(C)C ZAYGISOXMIXWHX-UHFFFAOYSA-N 0.000 description 1
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NUCFNMOPTGEHQA-UHFFFAOYSA-N 3-bromo-2h-pyrazolo[4,3-c]pyridine Chemical class C1=NC=C2C(Br)=NNC2=C1 NUCFNMOPTGEHQA-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- IQMGOTOKEZLVSJ-UHFFFAOYSA-N 3-octan-3-yloxycarbonylbut-3-enoic acid Chemical compound CCCCCC(CC)OC(=O)C(=C)CC(O)=O IQMGOTOKEZLVSJ-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
- LEUWBMAQQQENOO-UHFFFAOYSA-N 4-(4-chlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1h-pyridine-5-carboxylic acid Chemical class C1C(=O)NC(C)=C(C(O)=O)C1C1=CC=C(Cl)C=C1 LEUWBMAQQQENOO-UHFFFAOYSA-N 0.000 description 1
- VVAAYFMMXYRORI-UHFFFAOYSA-N 4-butoxy-2-methylidene-4-oxobutanoic acid Chemical compound CCCCOC(=O)CC(=C)C(O)=O VVAAYFMMXYRORI-UHFFFAOYSA-N 0.000 description 1
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 description 1
- GPZYYYGYCRFPBU-UHFFFAOYSA-N 6-Hydroxyflavone Chemical compound C=1C(=O)C2=CC(O)=CC=C2OC=1C1=CC=CC=C1 GPZYYYGYCRFPBU-UHFFFAOYSA-N 0.000 description 1
- HKLZOALUTLRUOI-UHFFFAOYSA-N 8a-hydroperoxy-2,3,4,4a,5,6,7,8-octahydro-1h-naphthalene Chemical compound C1CCCC2CCCCC21OO HKLZOALUTLRUOI-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000538562 Banjos Species 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical class C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
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- 235000013769 triethyl citrate Nutrition 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- MXHBQKVKHGQWRB-UHFFFAOYSA-N trihexyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC)C(C(=O)OCCCCCC)=C1 MXHBQKVKHGQWRB-UHFFFAOYSA-N 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- YPDXSCXISVYHOB-UHFFFAOYSA-N tris(7-methyloctyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCC(C)C)C(C(=O)OCCCCCCC(C)C)=C1 YPDXSCXISVYHOB-UHFFFAOYSA-N 0.000 description 1
- FJFYFBRNDHRTHL-UHFFFAOYSA-N tris(8-methylnonyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC(C)C)C(C(=O)OCCCCCCCC(C)C)=C1 FJFYFBRNDHRTHL-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は新規な接着性プラスチゾル組成物、さらに詳し
くは、110〜160°C程度の低温でもゲル化接着が
可能で、かつ接着強度が高い上、良好な粘度の経時安定
性を有し、例えば自動車製造時における金属板間のンー
ラントや金属板表面に対する塗料などとして好適な無溶
剤型の接着性プラスチゾル組成物に関するものである。Detailed Description of the Invention [Industrial Application Field] The present invention provides a novel adhesive plastisol composition, more specifically, a novel adhesive plastisol composition that is capable of gelling and adhesion even at low temperatures of about 110 to 160°C and has high adhesive strength. Furthermore, the present invention relates to a solvent-free adhesive plastisol composition which has good viscosity and stability over time and is suitable for use as a wet runt between metal plates during automobile manufacturing, or as a paint on the surface of metal plates, for example.
[従来の技術]
塩化ビニル樹脂プラスチゾルは、可塑剤中に、−次粒子
の径力刺、2−3.c+m程度の塩化ビニル樹脂粉体を
熱安定剤、充填剤、顔料、その他の配合剤と共に混合分
散して成る樹脂組成物であって、注型成形、スラッシュ
成形、回転成形などの型成形、ナイフコートやロールコ
ートなとのスプレッドコート成形、あるいはスクリーン
塗布成形なとの成形法によって最終成形品に加工され、
例えは自動車製造時における金属板間のシーラントや金
属板表面に対する塗料などとして用いられる。[Prior Art] Vinyl chloride resin plastisol is prepared by adding 2-3. A resin composition made by mixing and dispersing vinyl chloride resin powder of approximately c+m with heat stabilizers, fillers, pigments, and other compounding agents, and is suitable for mold forming such as cast molding, slush molding, and rotary molding, and knife molding. It is processed into the final molded product using spread coat molding such as coat or roll coat, or screen coating molding.
For example, it is used as a sealant between metal plates during automobile manufacturing and as a paint for the surface of metal plates.
このような塩化ビニル樹脂プラスチゾルに要求される性
能としては、例えば粘度の経時安定性が良好であること
、低温でゲル化接着が可能であること、接着強度が高い
ことなどが挙げられる。The performance required of such a vinyl chloride resin plastisol includes, for example, good stability of viscosity over time, ability to form gelatinous adhesives at low temperatures, and high adhesive strength.
前記プラスチゾルには、塩化ビニル系樹脂として、通常
塩化ビニル−酢酸ビニル共重合体、塩化ビニル−酢酸ビ
ニル−マレイン酸共重合体、塩化ビニル−酢酸ビニル−
ビニルアルコール共重合体などの塩化ビニル共重合体が
用いられるが、これらの共重合体のみでは接着強度が不
十分であるため、従来、ポリアミドアミンやイソシアネ
ート化合物などの接着向上剤を、前記共重合体に添加す
る方法がよく行われている。しかしながら、ポリアミド
アミンやインシアネート化合物を添加する方法において
は、(1)プラスチゾルの粘度が経時的に増加する、(
2)油の付着した金属面への接着性tこ劣る、(3)1
80〜220 ’C程度の高温でゲル化しないと接着力
か低いので、プラスチック部材や化学繊維製品を周辺に
もつ金属に対して使用する場合、それらを劣化させるお
それがある、などの欠点を有している。As the vinyl chloride resin, the plastisol usually contains vinyl chloride-vinyl acetate copolymer, vinyl chloride-vinyl acetate-maleic acid copolymer, vinyl chloride-vinyl acetate-
Vinyl chloride copolymers such as vinyl alcohol copolymers are used, but since these copolymers alone do not have sufficient adhesive strength, conventionally adhesion improvers such as polyamide amines and isocyanate compounds have been added to the copolymers. A commonly used method is to add it to the coalescence. However, in the method of adding polyamidoamine or incyanate compounds, (1) the viscosity of plastisol increases over time;
2) Poor adhesion to oily metal surfaces, (3) 1
If it does not gel at a high temperature of about 80-220'C, its adhesive strength will be low, so if it is used on metals that have plastic parts or chemical fiber products around them, it may deteriorate them. are doing.
また、塩化ビニル共重合体中のカルボキシル基の含有量
を増加させると接着性が向上することが知られているが
、該カルボキシル基の含有量を増加させると、成形時の
発泡が激しくなり、その結果、接着強度が変動しやすい
という問題が生じる。Furthermore, it is known that increasing the content of carboxyl groups in a vinyl chloride copolymer improves adhesion; however, increasing the content of carboxyl groups increases foaming during molding, As a result, a problem arises in that the adhesive strength tends to fluctuate.
低温でゲル化接着可能な塩化ビニル樹脂プラスチゾルと
して、例えば塩化ビニル単独重合体又は共重合体、可塑
剤、エポキシ樹脂、酸無水物及び所望に応じ充填剤やイ
ミド化合物を含有して成る組成物が開示されている(特
開平2−18442号公報)、シかしながら、このプラ
スチゾルは、100〜120℃程度の低温でゲル化接着
が可能であるものの、粘度の経時安定性や接着強度につ
いては必ずしも満足しうるものではない。As a vinyl chloride resin plastisol that can be gelled and bonded at low temperatures, for example, a composition containing a vinyl chloride homopolymer or copolymer, a plasticizer, an epoxy resin, an acid anhydride, and optionally a filler or an imide compound is used. Although this plastisol can be gelled and bonded at a low temperature of about 100 to 120 degrees Celsius, it has been disclosed (Japanese Unexamined Patent Publication No. 2-18442) that the stability of the viscosity over time and the adhesive strength are not good. It's not always satisfying.
他方、塩化ビニル共重合体を用いた接着性組成物として
、例えば(1)塩化ビニルと特定の単量体とを乳化重合
させて成る水性合成樹脂エマルジョン(特開平2−91
141号公報)、(2)有機溶剤に、塩化ビニル−酢酸
ビニル−マレイン酸共重合体、エチレン系高分子量ポリ
マー、脂環式飽和炭化水素樹脂及び熱可塑性アクリル樹
脂を溶解させて成る溶液型接着剤(特開昭62−212
483号公報)、(3)塩化ビニル単位、カルボン酸ビ
ニルエステル単位及び炭素−炭素二重結合を有するリン
酸エステル単位から成る平均重合度100〜900の共
重合体を含有する溶液型接着剤(特開昭63−1126
75号公報)、(4)リン酸基を含有する塩化ビニル系
共重合体、エチレン−酢酸ビニル系共重合体、粘着樹脂
及び有機溶剤を含有して成る溶液型接着剤組成物(特開
平2−91141号公報)などが開示されている。On the other hand, as an adhesive composition using a vinyl chloride copolymer, for example, (1) an aqueous synthetic resin emulsion obtained by emulsion polymerization of vinyl chloride and a specific monomer (JP-A-2-91
141 Publication), (2) Solution-type adhesive made by dissolving vinyl chloride-vinyl acetate-maleic acid copolymer, ethylene-based high molecular weight polymer, alicyclic saturated hydrocarbon resin, and thermoplastic acrylic resin in an organic solvent. agent (JP-A-62-212
(3) A solution-type adhesive containing a copolymer with an average degree of polymerization of 100 to 900 consisting of vinyl chloride units, carboxylic acid vinyl ester units, and phosphate ester units having a carbon-carbon double bond. Japanese Patent Publication No. 63-1126
(4) A solution-type adhesive composition comprising a vinyl chloride copolymer containing a phosphoric acid group, an ethylene-vinyl acetate copolymer, an adhesive resin, and an organic solvent (Japanese Patent Application Laid-open No. 75) 91141) and the like are disclosed.
しかしながら、前記(1)の水性合成樹脂エマルジョン
は、金属缶の表面や内面用塗料、レトルト食品容器のア
ルミニウム外皮コーティング剤なととして用いられる水
性エマルジョンであって、本発明の目的とする金属板間
のシーラントや金属板表面への塗料などとして用いられ
るプラスチゾルとは異なるものであるし、また前記(2
)、ぐ3)及び(4)の接着剤は、いずれも溶液型であ
って有機溶剤を含有するため、人体に対する安全性、大
気汚染、火災や爆発の危険性などの問題があり、有機溶
剤を用いない本発明のプラスチゾルとは異なるものであ
る。However, the aqueous synthetic resin emulsion (1) above is an aqueous emulsion used as a paint for the surface and inner surface of metal cans, an aluminum outer coating agent for retort food containers, etc. Plastisol is different from plastisol, which is used as a sealant or paint on the surface of metal plates.
), 3), and 4) are all solution-type and contain organic solvents, so there are problems with human safety, air pollution, and the risk of fire and explosion. This is different from the plastisol of the present invention which does not use .
[発明が解決しようとする課題]
本発明は、このような事情のもとで、110〜160℃
程度の低温でゲル化接着が可能で、かつ接着強度が高い
上、良好な粘度の経時安定性を有する無溶剤型の接着性
プラスチゾル組成物を提供することを目的としてなされ
たものである。[Problems to be Solved by the Invention] Under these circumstances, the present invention solves the problem at 110 to 160°C.
The purpose of this invention is to provide a solvent-free adhesive plastisol composition that is capable of gelatinous adhesion at a relatively low temperature, has high adhesive strength, and has good viscosity stability over time.
[課題を解決するj;めの手段コ
本発明者らは、前記の好ましい性質を有する接着性プラ
スチゾル組成物を開発すべく鋭意研究を重ねた結果、特
定の塩化ビニル共重合体、無機充填剤及び可塑剤を含有
して成る組成物により、その目的を達成しうろことを見
い出し、この知見に基づいて本発明を完成するに至った
。[Means for solving the problem] As a result of intensive research to develop an adhesive plastisol composition having the above-mentioned preferable properties, the present inventors found that a specific vinyl chloride copolymer and an inorganic filler were used. It was discovered that the object could be achieved by a composition containing a plasticizer and a plasticizer, and based on this knowledge, the present invention was completed.
すなわち本発明は、(A)(イ)塩化ビニル単位60〜
96重量%と、(ロ)−重代
%式%(1)
(式中のR’は炭素数1〜8のアルキル基である)で表
されるカルボン酸ビニルエステルの単位1〜20重量%
及び(ハ)−重代
%式%
(式中のR2は炭素数1〜8のアルキル基である)で表
されるマレイン酸モノアルキルエステルの単位3〜20
重量%とを含有し、かつ(ロ)単位/(ハ)単位重量比
が0.3以上の塩化ビニル共重合体と、(B)無機充填
剤と、(C)可塑剤とを含有して成る接着性プラスチゾ
ル組成物を提供するものである。That is, the present invention provides (A) (a) vinyl chloride units of 60 to
96% by weight, and 1 to 20% by weight of carboxylic acid vinyl ester units represented by the formula % (1) (R' in the formula is an alkyl group having 1 to 8 carbon atoms)
and (c) - Units 3 to 20 of maleic acid monoalkyl ester represented by the formula % (R2 in the formula is an alkyl group having 1 to 8 carbon atoms)
% by weight and has a (b) unit/(c) unit weight ratio of 0.3 or more, (B) an inorganic filler, and (C) a plasticizer. The present invention provides an adhesive plastisol composition comprising:
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明組成物において、(A)成分として用いられる塩
化ビニル共重合体は、塩化ビニルと前記−重代(I)で
表されるカルボン酸ビニルエステルと前記−重代(If
)で表されるマレイン酸モノアルキルエステルとを共重
合させることにより得られる。この際、本発明の目的が
損なわれない範囲で、その他の共重合可能な単量体を併
用することかできる。In the composition of the present invention, the vinyl chloride copolymer used as component (A) consists of vinyl chloride, a carboxylic acid vinyl ester represented by the above-mentioned (I), and the above-mentioned -
) is obtained by copolymerizing maleic acid monoalkyl ester represented by: At this time, other copolymerizable monomers may be used in combination as long as the object of the present invention is not impaired.
前記−重代(I)で表されるカルボン酸ビニルエステル
は、該式(I)中のR↓が炭素数1〜8のアルキル基で
あって、このようなものとしては、例えば酢酸ビニル、
プロピオン酸ビニノ呟カプロン酸ビニル、カプリル酸ビ
ニルなどが挙げられ、これらは1種用いてもよいし、2
種以上を組み合わせて用いてもよい。In the carboxylic acid vinyl ester represented by the above-mentioned (I), R↓ in the formula (I) is an alkyl group having 1 to 8 carbon atoms, such as vinyl acetate,
Examples include vinyl propionate, vinyl caproate, vinyl caprylate, etc., and these may be used alone or in combination.
You may use combinations of more than one species.
また、前記−重代(II)で表されるマレイン酸モノア
ルキルエステルは、該式(U)中のR2が炭素数1〜8
のアルキル基であって、このようなものとしては、例え
ばマレイン酸のモノメチル、モノエチル、モノプロピル
、モノブチル、モノペンチル、モノヘキシル、モノヘプ
チル、モノオクチル、モノシクロヘキシルエステルなど
が挙げられ、これらは1種用いてもよいし、2種以上を
組み合わせて用いてもよい。In addition, in the maleic acid monoalkyl ester represented by the above-mentioned (II), R2 in the formula (U) has 1 to 8 carbon atoms.
Examples of such alkyl groups include monomethyl, monoethyl, monopropyl, monobutyl, monopentyl, monohexyl, monoheptyl, monooctyl, and monocyclohexyl esters of maleic acid. or a combination of two or more types may be used.
さらに、所望に応じて用いられる他の共重合可能な単量
体としては、例えばアクリル酸、メタクリル酸、エタク
リル酸、マレイン酸、ケイ皮酸、無水マレイン酸、フマ
ール酸、イタコン酸、無水イタコン酸などの不飽和モノ
カルボン酸、不飽和ジカルボン酸及びその酸無水物、7
マール酸モノアルキルエステル、イタコン酸モノアルキ
ルエステルなどの不飽和ジカルボン酸モノアルキルエス
テル、(メタ)アクリル酸のメチル、エチノ呟 プロビ
ノペブチノペオクチル、シクロヘキシル、ベンジルエス
テルなどの不飽和モノカルボン酸エステル類、マレイン
酸やフマール酸のジメチル、ジエチル、ジブロビノベジ
ブチル、ジオクチノベジシクロヘキシル、ジベンジルエ
ステルなどの不飽和ジカルボンジエステル類、メチルビ
ニルエーテル、エチルビニルエーテル、プロピルヒニル
エーテルなとのビニルニーチル類、エチレン、プロピレ
ン、ブテン−1、ペンテン−1なとのオレフィン類、ス
チレンやα−メチルスチレンなどの芳香族モノビニル化
合物、アクリロニトリルやメタクリロニトリルなどのシ
アン化ビニル化合物、さらには塩化ビニリデンなどが挙
げられる。これらの所望に応じて用いられる単量体は1
種用いてもよいし、2種以上を組み合わせて用いてもよ
い。Further, other copolymerizable monomers that may be used as desired include, for example, acrylic acid, methacrylic acid, ethacrylic acid, maleic acid, cinnamic acid, maleic anhydride, fumaric acid, itaconic acid, and itaconic anhydride. Unsaturated monocarboxylic acids, unsaturated dicarboxylic acids and their acid anhydrides, such as 7
Unsaturated dicarboxylic acid monoalkyl esters such as maric acid monoalkyl esters and itaconic acid monoalkyl esters, unsaturated monocarboxylic acids such as methyl (meth)acrylic acid, ethinopebutinopeoctyl, cyclohexyl, and benzyl esters. Esters, unsaturated dicarbon diesters such as dimethyl, diethyl, dibrobinobedibutyl, dioctinovedicyclohexyl, and dibenzyl ester of maleic acid and fumaric acid, vinylnityls such as methyl vinyl ether, ethyl vinyl ether, and propyl vinyl ether, ethylene Examples include olefins such as , propylene, butene-1, and pentene-1, aromatic monovinyl compounds such as styrene and α-methylstyrene, vinyl cyanide compounds such as acrylonitrile and methacrylonitrile, and vinylidene chloride. These optional monomers are 1
A species may be used, or two or more species may be used in combination.
該(A)成分の塩化ビニル共重合体の敦造方法について
は特に制限はなく、従来プラスチゾルに用いられている
塩化ビニル共重合体の製造に慣用されている方法、例え
ば微細懸濁重合法や播種乳化重合法などを用いることが
できる。There are no particular restrictions on the method for producing the vinyl chloride copolymer of component (A), and methods commonly used for producing vinyl chloride copolymers conventionally used in plastisols, such as fine suspension polymerization and A seeded emulsion polymerization method or the like can be used.
該微細懸濁重合法は、触媒として油溶性触媒を用い、重
合開始前に単量体油滴の粒径を均質化処理によって予め
調節し、均質分散重合させる方法である。このような微
細懸濁重合法においては、触媒として油溶性のラジカル
開始剤が使用され、この油溶性のラジカル開始剤として
は、例えばジベンゾイルペルオキシド、ジー3.5.5
−トリメチルヘキサノイルペルオキンド、ジラウロイル
ペルオキンドなどのジアシルペルオキシド類、ジイソプ
口ビルペルオキシジカーポ不一ト、ジー5eC−ブチル
ペルオキシジカーボネート、ジー2−エチルヘキシルペ
ルオキシジカーボネートなどのベルオキシジカーポ不−
ト類、t−ブチルペルオキシビバレート、t−ブチルペ
ルオキシネオデカノエートなどのペルオキシエステル類
、あるいはアセチルシクロへキシルスルホニルペルオキ
シド、ジサクシニックアシッドペルオキシドなどの何機
過酸化物、さらには2.2′〜アゾビスイソブチロニト
リル、2.2″−アゾビス−2−メチルブチロニトリル
、2.2′−アゾビスジメチルバレロニトリルなどのア
ゾ化合物などが挙げられる。The fine suspension polymerization method is a method in which an oil-soluble catalyst is used as a catalyst, the particle size of monomer oil droplets is adjusted in advance by homogenization treatment before the start of polymerization, and homogeneous dispersion polymerization is carried out. In such a fine suspension polymerization method, an oil-soluble radical initiator is used as a catalyst, and examples of the oil-soluble radical initiator include dibenzoyl peroxide, di-3.5.5
- Diacyl peroxides such as trimethylhexanoyl peroquinde and dilauroyl peroquinde; peroxydicarbonates such as diisobutyl peroxydicarbonate, di-5eC-butyl peroxydicarbonate, and di-2-ethylhexyl peroxydicarbonate; Un-
peroxyesters such as t-butylperoxybivalate and t-butylperoxyneodecanoate, or peroxides such as acetylcyclohexylsulfonyl peroxide and disuccinic acid peroxide, and even 2.2' Examples include azo compounds such as ~azobisisobutyronitrile, 2.2''-azobis-2-methylbutyronitrile, and 2.2'-azobisdimethylvaleronitrile.
これらの触媒は1種用いてもよいし、2種以上を組み合
わせて用いてもよく、その使用量は、単量体の種類、量
及び仕込方式などによって適宜選ばれるが、通常使用単
量体100重量部当たり、0.001〜5.0重量部の
範囲で選ばれる。One type of these catalysts may be used, or two or more types may be used in combination, and the amount used is appropriately selected depending on the type and amount of the monomer, the preparation method, etc. It is selected in a range of 0.001 to 5.0 parts by weight per 100 parts by weight.
また、微細懸濁重合法においては、通常界面活性剤が用
いられる。この界面活性剤としては、例えばラウリル硫
酸エステルナトリウム、ミリスチル硫酸エステルナトリ
ウムなどのアルキル硫酸エステル塩類、ドデシルベンゼ
ンスルホン酸ナトリウム、ドデシルベンゼンスルホン酸
カリウムなどのアルキルアリールスルホン酸塩類、ジオ
クチルスルホコハク酸ナトリウム、ジヘキシルスルホコ
ハク酸ナトリウムなどのスルホコハク酸エステル塩類、
ラウリン酸アンモニウム、ステアリン酸カリウムなどの
脂肪酸塩類、ポリオキシエチレンアルキル硫酸エステル
塩類、ポリオキシエチレンアルキルアリール硫酸エステ
ル塩類などのアニオン性界面活性剤類、ソルビタンモノ
オレート、ポリオキシエチレンソルビタンモノステアレ
ートなどのソルビタンエステル類、ポリオキシエチレン
アルキルエーテル類、ポリオキシエチレンアルキルフェ
ニルエーテル類、ポリオキシエチレンアルキルエステル
類などのノニオン性界面活性剤類、セチルピリジニウム
クロリド、セチルトリメチルアンモニウムプロミドなど
のカチオン性界面活性剤などが挙げられ、これらは1種
用いてもよいし、2種以上を組み合わせて用いてもよく
、その使用量は、通常使用単量体100重量部当たり、
0.05〜5重量部、好ましくは0.2〜4.0重量部
の範囲で選ばれる。Further, in the fine suspension polymerization method, a surfactant is usually used. Examples of the surfactant include alkyl sulfate salts such as sodium lauryl sulfate and sodium myristyl sulfate, alkylaryl sulfonates such as sodium dodecylbenzenesulfonate and potassium dodecylbenzenesulfonate, sodium dioctylsulfosuccinate, and dihexylsulfosuccinate. sulfosuccinate salts such as sodium chloride,
Fatty acid salts such as ammonium laurate and potassium stearate, anionic surfactants such as polyoxyethylene alkyl sulfate salts and polyoxyethylene alkylaryl sulfate salts, sorbitan monooleate, polyoxyethylene sorbitan monostearate, etc. Nonionic surfactants such as sorbitan esters, polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, and polyoxyethylene alkyl esters; cationic surfactants such as cetylpyridinium chloride and cetyltrimethylammonium bromide These may be used alone or in combination of two or more, and the amount used is usually per 100 parts by weight of the monomer used,
It is selected in the range of 0.05 to 5 parts by weight, preferably 0.2 to 4.0 parts by weight.
この微細懸濁重合法においては、まず水性媒体中に、前
記油溶性触媒、単量体、前記界面活性剤及び所望に応じ
て用いられる高級脂肪酸類や高級アルコール類などの重
合助剤、その他の添加剤を加え、ホモジナイザーにより
均質化処理してプレミックスし、油滴の粒径調節を行う
。該ホモジナイザーとしては、例えばコロイドミノ呟振
動撹拌機、二段式高圧ポンプ、ノズルやオリアイスから
の高圧噴出、超音波撹拌などが挙げられる。さらに、油
滴の粒径の調節は、均質化処理時の剪断力の制御、重合
中の撹拌条件、反応装置の形式、界面活性剤や添加剤の
量などにより影響されるが、=HL++笛量か子備t1
こ上り、遍尚な条件を選択することができる。In this fine suspension polymerization method, the oil-soluble catalyst, monomer, surfactant, polymerization aids such as higher fatty acids and higher alcohols used as desired, and other additives are first added to an aqueous medium. Add additives and premix by homogenizing with a homogenizer to adjust the particle size of oil droplets. Examples of the homogenizer include a colloidal microvibration stirrer, a two-stage high-pressure pump, high-pressure jetting from a nozzle or Orice, and ultrasonic stirring. Furthermore, the adjustment of the particle size of oil droplets is influenced by the control of shear force during homogenization, stirring conditions during polymerization, type of reactor, amount of surfactant and additives, etc. quantity or kobi t1
You can select various conditions.
次に、このようにして均質化処理されたプレミックス液
は重合缶に送られ、ゆっくりと撹拌しながら昇温し、通
常30〜80℃の範囲の温度において重合が行われる。Next, the premix liquid homogenized in this way is sent to a polymerization tank, and the temperature is slowly raised while stirring, and polymerization is carried out at a temperature usually in the range of 30 to 80°C.
このようにして粒子径が0.2〜3μm程度の塩化ビニ
ル共重合体微粒子が均質に分散したラテックスが得られ
る。このラテックスは、通常塩析又は噴霧乾燥などの公
知の処理が施され、重合体は固形物として取り出される
。該重合体の分子量は、目的に応じて反応温度や分子量
調節剤により適宜調節される。In this way, a latex in which vinyl chloride copolymer fine particles having a particle size of about 0.2 to 3 μm are homogeneously dispersed is obtained. This latex is usually subjected to known treatments such as salting out or spray drying, and the polymer is taken out as a solid. The molecular weight of the polymer is appropriately adjusted by adjusting the reaction temperature and molecular weight regulator depending on the purpose.
一方、播種乳化重合法は、予め通常の乳化重合や乳懸濁
重合により調製された塩化ビニル樹脂粒子を核として、
アニオン性界面活性剤又はそれとノニオン性界面活性剤
とを用い、水性媒体中で粒子の肥大化重合反応を行わせ
る方法である。この際用いられる核粒子の径は、通常平
均0.03〜0.7μmの範囲にあり、またその使用量
は使用−+ス■4汁1八凸舌番城率tφ杓 3堂17ζ
0看置部の範囲で選ばれる。On the other hand, the seeded emulsion polymerization method uses vinyl chloride resin particles prepared in advance by conventional emulsion polymerization or milk suspension polymerization as cores.
This is a method in which an anionic surfactant or an anionic surfactant and a nonionic surfactant are used to carry out a polymerization reaction to enlarge particles in an aqueous medium. The diameter of the core particles used at this time is usually in the range of 0.03 to 0.7 μm on average, and the amount used is - + Su ■ 4 soup 1 8 convex tongue banjo ratio t φ scoop 3 hall 17 ζ
Selected within the range of 0 nursing units.
さらに、アニオン性界面活性剤としては、通常乳化重合
に用いられる公知のもの、例えばアルキルベンゼンスル
ホン酸塩、アルキルスルホン酸塩、アルキル硫酸エステ
ル塩、脂肪酸金属塩、ポリオキシアルキルエーテル硫酸
エステル塩、ポリオキシエチレンカルボン酸エステル硫
酸エステル塩、ポリオキシエチレンアルキルフェニルエ
ーテル硫酸エステル塩、コハク酸ジアルキルエステルス
ルホン酸塩などが挙げられ、これらは1種用いてもよい
し、2種以上を組み合わせて用いてもよい。Furthermore, as the anionic surfactant, there are known ones commonly used in emulsion polymerization, such as alkylbenzene sulfonates, alkyl sulfonates, alkyl sulfate salts, fatty acid metal salts, polyoxyalkyl ether sulfate salts, and polyoxyalkyl sulfonate salts. Examples include ethylene carboxylic acid ester sulfate salt, polyoxyethylene alkyl phenyl ether sulfate salt, succinic acid dialkyl ester sulfonate salt, and these may be used alone or in combination of two or more types. .
また、ノニオン性界面活性剤としては、例えばポリオキ
シエチレンアルキルフェニルエーテル、ポリオキシエチ
レンアルキルエーテル、ポリオキシエチレン脂肪酸エス
テル、ポリオキシエチレンンルビタン脂肪酸エステル、
ポリオキシエチレンアルキルエーテルグリセリンホウ酸
エステル、ポリオキシエチレンアルキルエーテルリン酸
エステル、ポリオキシエチレンなど、ポリオキシエチレ
ン鎖を分子内に有し、界面活性能を有する化合物及び前
お化合物のポリオキシエチレン鎖がオキシエチレン、オ
キシプロピレンの共重合体で代替されている化合物、さ
らにはソルビタン脂肪酸エステル、脂肪酸グリセリンエ
ステル、グリセリン脂肪酸エステル、ペンタエリスリト
ール脂肪酸エステルなどが挙げられ、これらは1種用い
てもよいし、2種以上を組み合わせて用いてもよい。In addition, examples of nonionic surfactants include polyoxyethylene alkylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, polyoxyethylene rubitan fatty acid ester,
Compounds having a polyoxyethylene chain in the molecule and having surface-active ability, such as polyoxyethylene alkyl ether glycerin borate, polyoxyethylene alkyl ether phosphate, polyoxyethylene, etc., and polyoxyethylene chains of the aforementioned compounds. is replaced with a copolymer of oxyethylene or oxypropylene, further examples include sorbitan fatty acid ester, fatty acid glycerin ester, glycerin fatty acid ester, pentaerythritol fatty acid ester, etc., and these may be used alone, or You may use two or more types in combination.
これらの界面活性剤の使用量については、アニオン性界
面活性剤は、通常使用する単量体100重量部当たり、
0.1〜5重量部の範囲で選ばれ、ノニオン性界面活性
剤は、通常0〜5重量部の範囲で選ばれる。Regarding the usage amount of these surfactants, the anionic surfactants are usually used in the following amounts per 100 parts by weight of monomers:
The amount of the nonionic surfactant is selected in the range of 0.1 to 5 parts by weight, and the amount of the nonionic surfactant is usually selected in the range of 0 to 5 parts by weight.
この播種乳化重合においては、触媒として水溶性還元剤
と有機過酸化物との組合せが用いられる。In this seeded emulsion polymerization, a combination of a water-soluble reducing agent and an organic peroxide is used as a catalyst.
該水溶性還元剤としては、例えば水に可溶な通常のラジ
カル酸化還元重合触媒成分として用いられる還元剤、例
えばエチレンジアミン四酢酸又はそのナトリウム塩やカ
リウム塩、あるいはこれらと鉄、銅、クロムなどの重金
属との錯化合物、スルフィン酸又はそのナトリウム塩や
カリウム塩、C−アスコルビン酸又はそのナトリウム塩
、カリウム塩、カルシウム塩、ピロリン酸第−鉄、硫酸
第一鉄、硫酸第一鉄アンモニウム、亜硫酸ナトリウム、
酸性亜硫酸ナトリウム、ホルムアルデヒドスルホキシル
酸ナトリウム、還元糖類などが挙げられ、これらは1種
用いてもよいし、2種以上を組み合わせて用いてもよい
。これらの還元剤の使用量は、使用する単量体100重
量部当たり、通常0.00001〜5重量部の範囲で選
ばれる。The water-soluble reducing agent is, for example, a reducing agent that is soluble in water and used as a normal radical redox polymerization catalyst component, such as ethylenediaminetetraacetic acid or its sodium salt or potassium salt, or a combination thereof with iron, copper, chromium, etc. Complex compounds with heavy metals, sulfinic acid or its sodium salt or potassium salt, C-ascorbic acid or its sodium salt, potassium salt, calcium salt, ferrous pyrophosphate, ferrous sulfate, ferrous ammonium sulfate, sodium sulfite ,
Examples include acidic sodium sulfite, sodium formaldehyde sulfoxylate, and reducing sugars, and these may be used alone or in combination of two or more. The amount of these reducing agents used is usually selected within the range of 0.00001 to 5 parts by weight per 100 parts by weight of the monomers used.
一方、有機過酸化物としては、例えばクメンヒドロペル
オキシド、p−サイメンヒドロペルオキシド、t−ブチ
ルイソプロピルベンゼンヒドロベルオキシド、ジイソプ
ロピルベンゼンヒドロベルオキシド、p−メンタンヒド
ロペルオキシド、デカリンヒドロペルオキシド、t−ア
ミルヒドロペルオキシド、t−ブチルヒドロペルオキシ
ド、イソプロピルヒドロペルオキシドなどのヒドロペル
オキシド類が挙げられる。これらの有機過酸化物は1種
用いてもよいし、2種以上を組み合わせて用いてもよく
、その使用量は、通常使用する単量体100重量部当た
り、0.001〜5重量部の範囲で選ばれる。On the other hand, examples of organic peroxides include cumene hydroperoxide, p-cymene hydroperoxide, t-butylisopropylbenzene hydroperoxide, diisopropylbenzene hydroperoxide, p-menthane hydroperoxide, decalin hydroperoxide, and t-amyl hydroperoxide. , t-butyl hydroperoxide, and isopropyl hydroperoxide. These organic peroxides may be used alone or in combination of two or more, and the amount used is usually 0.001 to 5 parts by weight per 100 parts by weight of the monomer used. selected within the range.
次に、播種乳化重合法の好適な1例について説明すると
、まず塩化ビニル樹脂核粒子の水性エマルジョンを調製
したのち、これに前記水溶性還元剤及び単量体を仕込み
、加温して30〜80℃程度の温度に保持する。一方、
別途に前記界面活性剤を用いて有機過酸化物の水性エマ
ルジョンと、前訊界面活性剤水溶液とを調製し、これら
を前記の塩化ビニル樹脂核粒子、水溶性還元剤及び単量
体を含有する水性エマルジョンに、通常30〜80°C
の範囲の温度を保持しながら連続的に投入して、重合反
応を行う。なお、この播種乳化重合においては、使用さ
れる界面活性剤や重合触媒の作用を助長するために、高
級脂肪酸、高級アルコール、無機塩類、水溶性高分子化
合物などを併用してもよい。Next, a preferred example of the seeded emulsion polymerization method will be described. First, an aqueous emulsion of vinyl chloride resin core particles is prepared, and then the water-soluble reducing agent and monomer are added thereto, and the mixture is heated to Maintain the temperature at about 80°C. on the other hand,
Separately, an aqueous emulsion of an organic peroxide and an aqueous surfactant solution are prepared using the above-mentioned surfactant, and these are mixed with the above-mentioned vinyl chloride resin core particles, a water-soluble reducing agent, and a monomer. For aqueous emulsions, usually 30-80°C
The polymerization reaction is carried out by continuously charging the polymer while maintaining the temperature within the range of . In addition, in this seeded emulsion polymerization, higher fatty acids, higher alcohols, inorganic salts, water-soluble polymer compounds, etc. may be used in combination to enhance the action of the surfactant and polymerization catalyst used.
重合反応終了後、生成した塩化ビニル共重合体粒子を含
有するエマルジョンから、前記の致細懸濁重合法の場合
と同様にして、該塩化ビニル共重合体を固形物として取
り出す。この共重合体の分子量は、目的に応じて反応温
度や分子量調節剤などにより適宜調節される。After the polymerization reaction is completed, the vinyl chloride copolymer particles are taken out as a solid from the emulsion containing the produced vinyl chloride copolymer particles in the same manner as in the fine suspension polymerization method described above. The molecular weight of this copolymer is appropriately adjusted by adjusting the reaction temperature, molecular weight regulator, etc. depending on the purpose.
このようにして得られた(A)成分の塩化ビニル共重合
体は、必須単位として(イ)塩化ビニル単位、(ロ)カ
ルボン酸ビニルエステル単位及び(ハ)マレイン酸モノ
アルキルエステル単位ヲ含有するものであって、該(ロ
)単位及び(ハ)単位の含有量は、それぞれ1〜20重
量%及び3〜20重量%の範囲にあり、かつ(ロ)単位
/(ハ)単位重量比が0.3以上であることが必要であ
る。The vinyl chloride copolymer of component (A) thus obtained contains (a) vinyl chloride units, (b) carboxylic acid vinyl ester units, and (c) maleic acid monoalkyl ester units as essential units. The content of the (b) unit and (c) unit is in the range of 1 to 20% by weight and 3 to 20% by weight, respectively, and the (b) unit/(c) unit weight ratio is It is necessary that it is 0.3 or more.
これらの条件を満たさない塩化ビニル共重合体では、本
発明の目的が十分に達せられない。A vinyl chloride copolymer that does not satisfy these conditions will not be able to fully achieve the object of the present invention.
本発明組成物においては、(B)成分として無機充填剤
を含有することが必要である。この無機充填剤が含有さ
れてない場合は、該組成物はゲル化接着時に発泡が生じ
、十分な接着力が得られない。この(B)成分の含有量
は、(A)成分の塩化ビニル共重合体100重量部当t
;す、30〜500重量%の範囲にあることが好ましい
。該無機充填剤としては、沈降性炭酸カルシウム、重質
炭酸カルシウム、極微細炭酸カルシウムの如き炭酸カル
シウム、炭酸マグネシウム、シリカ、タルク、ケインウ
土、クレー、マイカなどのケイ酸塩、アルミナなどのい
ずれも用いることができる。The composition of the present invention needs to contain an inorganic filler as component (B). If this inorganic filler is not contained, the composition will foam during gelation and adhesion, and sufficient adhesive strength will not be obtained. The content of component (B) is t per 100 parts by weight of the vinyl chloride copolymer of component (A).
; It is preferably in the range of 30 to 500% by weight. Examples of the inorganic filler include calcium carbonate such as precipitated calcium carbonate, ground calcium carbonate, and ultrafine calcium carbonate, magnesium carbonate, silicates such as silica, talc, cane earth, clay, mica, and alumina. Can be used.
本発明組成物において、(C)成分として用いられる可
塑剤については特に制限はなく、従来塩化ビニル樹脂プ
ラスチゾルの可塑剤として慣用されているもの、例えば
ジメチルフタレート、ジエチルマレート、ジブチルフタ
レート、ジー(2−エチルヘキシル)フタレート、ジ−
n−オクチルフタレート、ジイソブチルフタレート、ジ
エチルマレート、ジフェニルフタレート、ジインデシル
フタレート、ジトリデシルフタレート、ジインデシルフ
タレート、ジ(ヘブチノ1 ノニル、ウンデシル)フタ
レート、ベンジルフタレート、ブチルベンジルフタレー
ト、ジノニルフタレート、ジシクロヘキシルフタレート
などのフタル酸誘導体、ジメチルイソフタレート、ジー
(2−エチルヘキシル)インフタレート、ジイソオクチ
ルイソフタレートなどのイソフタル酸誘導体、ジー(2
−エチルヘキシル)テトラヒドロフタレート、ジ−n−
オクチルテトラヒドロフタレート、ジインデシルテトラ
ヒドロフタレートなどのテトラヒドロ7タル酸誘導体、
ジ−n−ブチルアジペート、ジー(2−エチルヘキシル
)アジペート、ジイソデシルアジペート、ジイソノニル
アジペートなどのアジピン酸誘導体、ジー(2−エチル
ヘキシル)アゼレート、ジイソオクチルアゼレート、ジ
−n−ヘキシルアゼレートなどのアゼライン酸誘導体、
ジ−n−ブチルセバケート、ジー(2−エチルヘキシル
)セバケートなどのセバシン酸誘導体、ジ−n−ブチル
マレート、ジメチルマレート、ジエチルマレート、ジー
(2−エチルヘキシル)マレートなどのマレイン酸誘導
体、ジ−n−ブチルフマレート、ジー(2−エチルヘキ
シル)フマレートなどの7タル酸誘導体、トリー(2−
エチルヘキシル)トリメリテート、トリイソオクチルト
リメリテート、トリイソデシルトリメリテート、トリイ
ソオクチルトリメリテート、トリーn−へキシルトリメ
リテート、トリイソノニルトリメリテートなどのトリメ
リット酸誘導体、テトラ−(2−エチルヘキシル)ピロ
メリテート、テトラ−n−オクチルピロメリテートなど
のピロメリットrji誘導体、トリエチルシトレート、
トリーローブチルシトレート、アセチルトリエチルシト
レート、アセチルトリー(2−エチルヘキシル)シトレ
ートなどのクエン酸誘導体、モノメチルイタコネート、
モノブチルイタコネート、ジメチルイタコネート、ジエ
チルイタコネート、ジブチルイタコネート、ジー(2−
エチルヘキシル)イタコネートなどのイタコン酸誘導体
、ブチルオレート、グリセリルモノオレート、ジエチレ
ングリコールモノオレートなどのオレイン酸誘導体、メ
チルアセチルリシルレート、プチルアセチルリシル−ト
、グリセリルモノリシルレート、ジエチレングリコール
モノリシルレートなどのリシノール酸誘導体、n−ブチ
ルステアレート、グリセリンモノステアレート、ジエチ
レングリコールジステアレートなどのステアリン酸誘導
体、ジエチレングリコールモノラウレート、ジエチレン
グリコールジペラルゴ不一ト、ペンタエリスリトール脂
肪酸エステルなどのその他の脂肪酸誘導体、トリエチル
ホスフェート、トリブチルホスフェート、トリー(2−
エチルヘキシル)ホスフェート、トリブトキシエチルホ
スフェート、トリフェニルホスフェート、クレジルジフ
ェニルホスフェート、トリクレジルホスフェート、トリ
キシレニルホスフェート、トリス(クロロエチル)ホス
フェートなどのリン酸誘導体、ジエチレングリコールジ
ベンゾエート、ジプロピレングリコールジベンゾエート
、トリエチレングリコールジベンゾエート、トリエチレ
ングリコールジー(2−エチルブチレート)、トリエチ
レングリコールジー(2−エチルヘキソエート)、ジブ
チルメチレンビスチオグリコレートなどのグリコール誘
導体、グリセロールモノアセテート、グリセロールトリ
アセテート、グリセロールトリブチレートなどのグリセ
リン誘導体、エポキシ化大豆油、エポキシブチルステア
レート、エポキシへキサヒドロフタル酸ジー2−エチル
ヘキシル、エポキシへキサヒドロフタル酸ジイソデシル
、エポキシトリグリセライド、エポキシ化オレイン酸オ
クチル、エポキシ化オレイン酸デシルなどのエポキシ誘
導体、アジピン酸系ポリエステル、セバシン酸系ポリエ
ステル、フタル酸系ポリエステルなどのポリエステル系
可塑剤、あるいは部分水添ターフェニル、接着性可塑剤
などが挙げられる。In the composition of the present invention, there are no particular restrictions on the plasticizer used as component (C), and those conventionally used as plasticizers for vinyl chloride resin plastisols, such as dimethyl phthalate, diethyl maleate, dibutyl phthalate, di( 2-ethylhexyl) phthalate, di-
n-octyl phthalate, diisobutyl phthalate, diethyl maleate, diphenyl phthalate, diindecyl phthalate, ditridecyl phthalate, diindecyl phthalate, di(hebutyno1nonyl, undecyl) phthalate, benzyl phthalate, butylbenzyl phthalate, dinonyl phthalate, dicyclohexyl phthalate phthalic acid derivatives such as dimethyl isophthalate, di(2-ethylhexyl) inphthalate, isophthalic acid derivatives such as diisooctylisophthalate, di(2-ethylhexyl) inphthalate,
-ethylhexyl)tetrahydrophthalate, di-n-
Tetrahydroheptalic acid derivatives such as octyltetrahydrophthalate and diindecyltetrahydrophthalate,
Adipic acid derivatives such as di-n-butyl adipate, di(2-ethylhexyl) adipate, diisodecyl adipate, and diisononyl adipate; azelain such as di(2-ethylhexyl) azelate, diisooctyl azelate, and di-n-hexyl azelate; acid derivatives,
Sebacic acid derivatives such as di-n-butyl sebacate and di(2-ethylhexyl)sebacate; maleic acid derivatives such as di-n-butyl maleate, dimethyl maleate, diethyl maleate, and di(2-ethylhexyl) maleate; Heptallic acid derivatives such as butyl fumarate, di(2-ethylhexyl) fumarate, tri(2-ethylhexyl) fumarate, etc.
trimellitic acid derivatives such as ethylhexyl trimellitate, triisooctyl trimellitate, triisodecyl trimellitate, triisooctyl trimellitate, tri-n-hexyl trimellitate, triisononyl trimellitate, tetra-( pyromellit rji derivatives such as 2-ethylhexyl) pyromellitate, tetra-n-octyl pyromellitate, triethyl citrate,
Citric acid derivatives such as trilobyl citrate, acetyl triethyl citrate, acetyl tri(2-ethylhexyl) citrate, monomethyl itaconate,
Monobutyl itaconate, dimethyl itaconate, diethyl itaconate, dibutyl itaconate, di(2-
Itaconic acid derivatives such as ethylhexyl itaconate, oleic acid derivatives such as butyl oleate, glyceryl monooleate, diethylene glycol monooleate, ricinoleic acid derivatives such as methyl acetyl lysyllate, butylacetyl lysyllate, glyceryl monolysyllate, diethylene glycol monolysyllate , stearic acid derivatives such as n-butyl stearate, glycerin monostearate, diethylene glycol distearate, other fatty acid derivatives such as diethylene glycol monolaurate, diethylene glycol dipelargomonoxide, pentaerythritol fatty acid ester, triethyl phosphate, tributyl phosphate , Tory (2-
phosphoric acid derivatives such as ethylhexyl) phosphate, tributoxyethyl phosphate, triphenyl phosphate, cresyl diphenyl phosphate, tricresyl phosphate, tricylenyl phosphate, tris(chloroethyl) phosphate, diethylene glycol dibenzoate, dipropylene glycol dibenzoate, Glycol derivatives such as ethylene glycol dibenzoate, triethylene glycol di(2-ethyl butyrate), triethylene glycol di(2-ethylhexoate), dibutyl methylene bisthioglycolate, glycerol monoacetate, glycerol triacetate, glycerol triacetate Glycerin derivatives such as butyrate, epoxidized soybean oil, epoxybutyl stearate, di-2-ethylhexyl epoxy hexahydrophthalate, diisodecyl epoxy hexahydrophthalate, epoxy triglyceride, epoxidized octyl oleate, epoxidized decyl oleate Examples include epoxy derivatives such as, polyester plasticizers such as adipic acid polyester, sebacic acid polyester, and phthalic acid polyester, partially hydrogenated terphenyl, and adhesive plasticizers.
これらの可塑剤は1種用いてもよいし、2種以上を組み
合わせて用いてもよく、その配合量は、(A)成分の塩
化ビニル共重合体100重量部当たり、通常40〜25
0重量%の範囲で選ばれる。These plasticizers may be used alone or in combination of two or more, and the amount thereof is usually 40 to 25 parts by weight per 100 parts by weight of the vinyl chloride copolymer (A).
It is selected in the range of 0% by weight.
本発明組成物には、本発明の目的を損なわない範囲で、
従来塩化ビニル樹脂プラスチゾルに慣用されている他の
添加成分を含有させることができる。The composition of the present invention includes, to the extent that it does not impair the purpose of the present invention,
Other additive components conventionally used in vinyl chloride resin plastisols can be included.
このようにして得られた本発明のプラスチゾル組成物は
110〜160℃程度の低温でもゲル化接着が可能で、
かつ加工時に発泡がなく、高い接着強度が得られる上、
良好な粘度の経時安定性を有している。The plastisol composition of the present invention thus obtained can be gelled and bonded even at low temperatures of about 110 to 160°C,
In addition, there is no foaming during processing, and high adhesive strength is obtained.
It has good viscosity stability over time.
[実施例]
次に、実施例により本発明をさらに詳細に説明するが、
本発明はこれらの例によってなんら限定されるものでは
ない。[Example] Next, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited in any way by these examples.
実施例1〜5、比較例1〜5
塩化ビニル系樹脂として、第1表に示す種類のものを用
いて、第1表に示す配合でプラスチゾル組成物を調製し
、該組成物の接着強度、貯蔵安定性、加工時の発泡の有
無及び変色の程度を求めた。Examples 1 to 5, Comparative Examples 1 to 5 Using the types of vinyl chloride resins shown in Table 1, plastisol compositions were prepared with the formulations shown in Table 1, and the adhesive strength of the composition, Storage stability, presence or absence of foaming during processing, and degree of discoloration were determined.
その結果を第1表に示す。The results are shown in Table 1.
なお、接着強度及び貯蔵安定性は次のようにして評価し
た。In addition, adhesive strength and storage stability were evaluated as follows.
(1)接着強度
脱脂処理された1mm厚の亜鉛板上に組成物を塗布して
140°Cで20分間加熱し、引張り剪断接漕強さを求
め、次の判定基準に従って評価した。(1) Adhesive Strength The composition was applied onto a 1 mm thick degreased zinc plate and heated at 140°C for 20 minutes to determine the tensile shear bonding strength and evaluate it according to the following criteria.
X:引張り剪断強さが15kgf/cm”以下Δ:引張
り剪断強さが25kg1/cm”以下O;引張り剪断強
さが35に9f/cが以下■:引張り剪断強さが35k
g1/cm2より大きい
(2)貯蔵安定性
組成物を23℃で7日間保持後、23℃における粘度を
測定し、初期値に対する粘度比Rを、式
:
:
:
%式%)
次の判定基準に従って評価した。X: Tensile shear strength is 15 kgf/cm" or less Δ: Tensile shear strength is 25 kg1/cm" or less O; Tensile shear strength is 35 to 9 f/c or less ■: Tensile shear strength is 35 k
(2) storage stability greater than g1/cm2 After holding the composition at 23°C for 7 days, measure the viscosity at 23°C, and calculate the viscosity ratio R to the initial value using the following criteria: It was evaluated according to the following.
Rが10以上
Rが3以上10未満
Rが1.5以上3未満
Rが1.5未満
[発明の効果]
本発明の接着性プラスチゾル組成物は、塩化ビニル系樹
脂として、塩化ビニル単位とカルボン酸ビニルエステル
単位とマレイン酸モノアルキルエステル単位とを含有し
て成る塩化ビニル共重合体を用い、この共重合体と無機
充填剤と可塑剤とを含有するものであって、110〜1
60℃程度の低温でもゲル化接着が可能で、加工時に発
泡や変色がほとんどなく、高い接着強度が得られる上、
良好な粘度の経時安定性を有しており、例えば自動車製
造時における金属板間のシーラントや金属板表面に対す
る塗料などとして好適に用いられる。R is 10 or more and R is 3 or more and less than 10 R is 1.5 or more and less than 3 R is less than 1.5 [Effect of the invention] The adhesive plastisol composition of the present invention has a vinyl chloride unit and a carboxyl group as a vinyl chloride resin. A vinyl chloride copolymer containing an acid vinyl ester unit and a maleic acid monoalkyl ester unit is used, and this copolymer, an inorganic filler, and a plasticizer are contained,
Gel adhesion is possible even at low temperatures of around 60℃, there is almost no foaming or discoloration during processing, and high adhesive strength is obtained.
It has good viscosity and stability over time, and is suitably used, for example, as a sealant between metal plates during automobile manufacturing or as a paint for the surface of metal plates.
特許出願人 日本ゼオン株式会社Patent applicant: Zeon Corporation
Claims (1)
ロ)一般式 ▲数式、化学式、表等があります▼ (式中のR^1は炭素数1〜8のアルキル基である)で
表されるカルボン酸ビニルエステルの単位1〜20重量
%及び(ハ)一般式 ▲数式、化学式、表等があります▼ (式中のR^2は炭素数1〜8のアルキル基である)で
表されるマレイン酸モノアルキルエステルの単位3〜2
0重量%とを含有し、かつ(ロ)単位/(ハ)単位重量
比が0.3以上の塩化ビニル共重合体と、(B)無機充
填剤と、(C)可塑剤とを含有して成る接着性プラスチ
ゾル組成物。 2(B)成分及び(C)成分の含有量が、(A)成分1
00重量部に対し、それぞれ30〜500重量部及び4
0〜250重量部である請求項1記載の接着性プラスチ
ゾル組成物。[Scope of Claims] 1(A)(a) 60 to 96% by weight of vinyl chloride units, and (
b) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. C) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (R^2 in the formula is an alkyl group having 1 to 8 carbon atoms) 3 to 2 units of maleic acid monoalkyl ester
0% by weight and a vinyl chloride copolymer having a (b) unit/(c) unit weight ratio of 0.3 or more, (B) an inorganic filler, and (C) a plasticizer. An adhesive plastisol composition comprising: 2 The contents of component (B) and component (C) are as follows: (A) component 1
00 parts by weight, 30 to 500 parts by weight and 4 parts by weight, respectively.
The adhesive plastisol composition according to claim 1, which contains 0 to 250 parts by weight.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26557590A JP2566846B2 (en) | 1990-10-03 | 1990-10-03 | Adhesive plastisol composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26557590A JP2566846B2 (en) | 1990-10-03 | 1990-10-03 | Adhesive plastisol composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH04142380A true JPH04142380A (en) | 1992-05-15 |
JP2566846B2 JP2566846B2 (en) | 1996-12-25 |
Family
ID=17419024
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP26557590A Expired - Fee Related JP2566846B2 (en) | 1990-10-03 | 1990-10-03 | Adhesive plastisol composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2566846B2 (en) |
-
1990
- 1990-10-03 JP JP26557590A patent/JP2566846B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2566846B2 (en) | 1996-12-25 |
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