USRE34093E - Aqueous adhesive compositions - Google Patents
Aqueous adhesive compositions Download PDFInfo
- Publication number
- USRE34093E USRE34093E US06/759,910 US75991085A USRE34093E US RE34093 E USRE34093 E US RE34093E US 75991085 A US75991085 A US 75991085A US RE34093 E USRE34093 E US RE34093E
- Authority
- US
- United States
- Prior art keywords
- alcohol
- diisocyanate
- vinyl
- iadd
- iaddend
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 42
- 239000000853 adhesive Substances 0.000 title abstract description 32
- 230000001070 adhesive effect Effects 0.000 title abstract description 32
- 239000000839 emulsion Substances 0.000 claims abstract description 29
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 20
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 20
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 229920000126 latex Polymers 0.000 claims abstract description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 15
- 239000004816 latex Substances 0.000 claims abstract description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000006185 dispersion Substances 0.000 claims abstract description 10
- 239000004094 surface-active agent Substances 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 hydrocarbon radical Chemical group 0.000 claims description 17
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229920001519 homopolymer Polymers 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 4
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 claims description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 claims description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 3
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 2
- JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 claims description 2
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 claims description 2
- MGZPILVOXGOTMY-UHFFFAOYSA-N 1,2,3,4-tetraisocyanatobutane Chemical compound O=C=NCC(N=C=O)C(N=C=O)CN=C=O MGZPILVOXGOTMY-UHFFFAOYSA-N 0.000 claims description 2
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 claims description 2
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 claims description 2
- FVLCBDPSQUONII-UHFFFAOYSA-N 1,4-diisocyanato-2,3-dimethylbutane Chemical compound O=C=NCC(C)C(C)CN=C=O FVLCBDPSQUONII-UHFFFAOYSA-N 0.000 claims description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 2
- SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 claims description 2
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- QCHSJPKDWOFACC-UHFFFAOYSA-N 2-Ethyl-4-methyl-1-pentanol Chemical compound CCC(CO)CC(C)C QCHSJPKDWOFACC-UHFFFAOYSA-N 0.000 claims description 2
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 claims description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims description 2
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 claims description 2
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 claims description 2
- BQAUXFAQNIKTPW-UHFFFAOYSA-N C=C.C=C.C=C.C=C.N=C=O.N=C=O Chemical compound C=C.C=C.C=C.C=C.N=C=O.N=C=O BQAUXFAQNIKTPW-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004440 Isodecyl alcohol Substances 0.000 claims description 2
- 239000004439 Isononyl alcohol Substances 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 229960000541 cetyl alcohol Drugs 0.000 claims description 2
- 229960000735 docosanol Drugs 0.000 claims description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 2
- JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 claims description 2
- 229940043348 myristyl alcohol Drugs 0.000 claims description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 2
- 229940055577 oleyl alcohol Drugs 0.000 claims description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 2
- 229940012831 stearyl alcohol Drugs 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000008199 coating composition Substances 0.000 abstract description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 description 17
- 150000002513 isocyanates Chemical class 0.000 description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 239000002023 wood Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 10
- 150000003871 sulfonates Chemical class 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000000123 paper Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 241000208140 Acer Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000007799 cork Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 229920005610 lignin Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JZLWSRCQCPAUDP-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-triamine;urea Chemical compound NC(N)=O.NC1=NC(N)=NC(N)=N1 JZLWSRCQCPAUDP-UHFFFAOYSA-N 0.000 description 1
- QQYSPMBMXXCTGQ-UHFFFAOYSA-N 1,4-dioxo-1,4-di(tridecoxy)butane-2-sulfonic acid;sodium Chemical compound [Na].CCCCCCCCCCCCCOC(=O)CC(S(O)(=O)=O)C(=O)OCCCCCCCCCCCCC QQYSPMBMXXCTGQ-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical class ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- GLDUZMNCEGHSBP-UHFFFAOYSA-N 2-(2-octylphenoxy)ethanol Chemical compound CCCCCCCCC1=CC=CC=C1OCCO GLDUZMNCEGHSBP-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- HMENQNSSJFLQOP-UHFFFAOYSA-N 2-bromoprop-2-enoic acid Chemical class OC(=O)C(Br)=C HMENQNSSJFLQOP-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- OQYUFQVPURDFKC-UHFFFAOYSA-N 2-methylbut-1-enylbenzene Chemical class CCC(C)=CC1=CC=CC=C1 OQYUFQVPURDFKC-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical class CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ORNUPNRNNSVZTC-UHFFFAOYSA-N 2-vinylthiophene Chemical class C=CC1=CC=CS1 ORNUPNRNNSVZTC-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical class CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical class ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- ZTHJQCDAHYOPIK-UHFFFAOYSA-N 3-methylbut-2-en-2-ylbenzene Chemical class CC(C)=C(C)C1=CC=CC=C1 ZTHJQCDAHYOPIK-UHFFFAOYSA-N 0.000 description 1
- ZWKNLRXFUTWSOY-UHFFFAOYSA-N 3-phenylprop-2-enenitrile Chemical class N#CC=CC1=CC=CC=C1 ZWKNLRXFUTWSOY-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical class CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229940116441 divinylbenzene Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- BLZSRIYYOIZLJL-UHFFFAOYSA-N ethenyl pentanoate Chemical compound CCCCC(=O)OC=C BLZSRIYYOIZLJL-UHFFFAOYSA-N 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
- C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
- C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/10—Copolymers of styrene with conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D131/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Coating compositions based on derivatives of such polymers
- C09D131/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C09D131/04—Homopolymers or copolymers of vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J125/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
- C09J125/02—Homopolymers or copolymers of hydrocarbons
- C09J125/04—Homopolymers or copolymers of styrene
- C09J125/08—Copolymers of styrene
- C09J125/10—Copolymers of styrene with conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J131/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Adhesives based on derivatives of such polymers
- C09J131/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C09J131/04—Homopolymers or copolymers of vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
Definitions
- This invention relates to a water-base adhesive and coating agent which is especially useful for the coating and bonding of wood and other porous materials and which also has good pot life.
- urea resins melamine-urea co-condensation resins and phenolic resins are used for the adhesives in the manufacture of plywood.
- the evolution of formaldehyde from these materials has been found to have adverse environmental effects. This evolution of formaldehyde is difficult if not impossible to avoid in the production of plywood and for this reason substitute adhesives have been sought.
- Various non-formaldehyde yielding water-based adhesive compositions have been suggested but many of them have inadequate water resistance and/or short pot lives as well as other disadvantages.
- One such adhesive system has been suggested in U.S. Pat. No.
- an adhesive comprising (1) an aqueous solution of polyvinyl alcohol, and (2) a hydrophobic solution of an isocyanate compound in an organic solvent.
- Such compositions can also contain an anionic surface active agent.
- the adhesive compositions of the present invention require no organic solvent and no polyvinyl alcohol in them.
- a water-based adhesive and coating composition which has excellent pot life (in excess of 40 hours at room temperature) and produces coatings and adhesive bonds which have excellent strength and water resistance and are devoid of any formaldehyde or formalin evolution during use or storage.
- compositions of this invention are made up of two main aqueous systems; namely, (1) an aqueous latex, emulsion or dispersion of a vinyl homopolymer or interpolymer of two or more vinyl monomers, and (2) an aqueous emulsion or dispersion of a polyisocyanate which has undergone at least partial reaction between some of its isocyanate groups with a monohydroxy alcohol having the formula ROH wherein R is a hydrocarbon radical containing at least one carbon atom and preferably R contains from six to thirty carbon atoms and wherein aqueous emulsion or dispersion (2) is stabilized with an emulsion stabilizer composed of a surfactant and an alcohol having the structure R'OH wherein R' is a hydrocarbon radical containing at least one carbon atom and more preferably wherein R' contains from six to thirty carbon atoms.
- Vinyl monomers useful in the present invention include the methyl, ethyl, propyl, isopropyl butyl, isobutyl, pentyl, and other similar esters of acrylic, methacrylic, ethacrylic, propacrylic, chloroacrylic, and bromoacrylic acids; the phenyl, benzyl and phenethyl esters of the aforementioned acids; vinyl aromatic hydrocarbons, such as styrene, vinyl toluene, dimethyl styrenes, trimethyl styrenes, ethyl styrenes, methyl ethyl styrenes, t-butyl styrenes, chloromethyl styrenes, mono chloro styrenes, dichloro styrenes, cyanostyrenes, vinyl naphthalenes, n-vinyl carbazole and vinyl thiophenes; the vinyl esters of saturated
- Particularly useful homopolymers and interpolymers of vinyl monomers for the purpose of this invention can include polymers and interpolymers of one or more monomers including vinyl acetate, vinyl chloride, vinylidene chloride, styrene, vinyl toluene, acrylonitrile, methacrylonitrile, acrylic ester, methacrylic esters, ethylene, isobutylene, butadiene, and isoprene.
- Polyisocyanates useful in this invention are organic isocyanates having at least two isocyanate groups per molecule.
- the polyisocyanates can be of low, high or intermediate molecular weight and can be any of a wide variety of organic polyisocyanates including ethylene diisocyanate, trimethylene diisocyanate, dodecamethylene diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate trimer, tetraethylene diisocyanate, pentamethylene diisocyanate, propylene-1,2-diisocyanate, 2,3-dimethyl tetramethylene diisocyanate, butylene-1,2-diisocyanate, butylene-1,3-diisocyanate, 1,4-diisocyanato cyclohexane, cyclopentene 1,3-diisocyanate, p-phenylene diisocyanate, 1-methyl phenylene-2,4-diisocyan
- Alcohols of the type ROH and R'OH mentioned above in which R and R' are independently selected which are most useful in this invention are preferably aliphatic mono alcohols including n-hexyl alcohol, n-heptyl alcohol, n-octyl alcohol, n-nonyl alcohol, n-decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, isohexyl alcohol, 2-ethyl hexanol, 2-ethyl isohexanol, iso octyl alcohol, isononyl alcohol, isodecyl alcohol, isotridecyl alcohol, isocetyl alcohol, isostearyl alcohol, oleyl alcohol, linoleyl alcohol and the like.
- the surfactants which in combination with the alcohols R'OH which are useful in stabilization of the at least partially modified polyisocyanate emulsions of this invention can be one or more of any of the well-known anionic, cationic and nonionic surfactants. It is usually advantageous to use anionic surfactants because such surfactants are most commonly used in the preparation of the vinyl polymer latices used in this invention and for purposes of compatibility the same type of surfactant is desired in both aqueous systems (1) and (2) of this invention.
- Anionic surfactants which are particularly useful in this invention include alkyl sulfonates, sulfonated aliphatic amines and amides, diphenyl sulfonates, ethoxylated fatty acids, lignin and lignin derivatives, olefin sulfonates, alkyl and inorganic phosphates, polyamine and carboxylic acids, sulfosuccinates, and alcohol sulfates, ethoxylated alcohol sulfates, sulfates and sulfonates of ethoxylated alkyl phenols, sulfates on fatty esters, sulfates and sulfonates of oils and fatty acid, alkyl aryl sulfonates, sulfonates of benzene, toluene, and xylene, sulfonates of condensed naphthalenes, sulfon
- the vinyl polymer latex which constitutes part (1) of this invention can be made by well-known emulsion polymerization techniques involving the polymerization of the vinyl monomer or monomers in aqueous emulsion with a free radical polymerization initiator. Emulsion stability is maintained by means of the usual surfactants emulsion stabilizers, suspending agents and the like as is well known to those skilled in the art.
- the organic phase of the polyisocyanate emulsion (2) of this invention is composed of at least one polyisocyanate in which at least some of the isocyanate groups have been allowed to react with an alcohol ROH to form an at least partially modified isocyanate.
- This organic phase is prepared by the treatment of from about 0.032 to 0.22 equivalents of ROH per isocyanate equivalent of the polyisocyanate.
- the emulsifier component in (2) can be present in from about 1 to 3 parts by weight of the modified isocyanate organic phase with the ratio of R'OH to surfactant in the emulsifier falling in the range of about 2 to 4%.
- the alcohol modified polyisocyanate emulsions (2) of this invention can be prepared by conventional methods. Batch preparation of the emulsions can be effected by adding a mixture of the modified isocyanate and emulsifying agent to vigorously agitated water or conversely, the water may be added to the isocyanate emulsifier mixture.
- the alcohol modified polyisocyanate can also be added to the aqueous emulsifier mixture. Very uniform emulsions are obtained by using homogenizing equipment, but any high speed mixing device can be used. Continuous preparation of the emulsions can be performed by feeding the components at controlled rates into a high shear mixing zone.
- these emulsions contain from about 65-75% by weight of the organic component
- the concentrated emulsions can also be diluted to any desired concentration by the addition of water.
- the emulsions can be prepared directly at low concentrations if so desired.
- compositions of the present invention composed of mixtures of (1) and (2) parts as described above exhibit tenacious adhesions to fibrous, non-fibrous, porous and non-porous, flexible and rigid, metallic and non-metallic, polymeric, leather, cork, wood and glass surfaces.
- compositions of this invention are ideally suited for use as impregnants, saturants or sealants for porous substances of many types. Where flexible substrates are involved, the in situ reaction of the reactive components confers strength and rigidity. In the case of moisture sensitive substrates, the presence of the compositions of this invention decreases water sensitivity and this makes them particularly valuable for treating wood, paper, paper board, textiles, and the like. In addition to applications to paper, the compositions of this invention can be used for stiffening, reinforcing, water-proofing, or modifying a variety of foam plastic fabrics and specialty papers derived from natural and synthetic fibers such as asbestos, cellulose, flax, nylon and the like.
- compositions of this invention can be used to seal wood and porous masonry such as concrete, mortar, plaster, stone and brick.
- the compositions of this invention can also be used as adhesives for binding wood chips, ground leather, ground cork, sand, glass fibers, carbon fibers and similar substances into sheet or molded forms. They are also useful as adhesives for laminating sheet materials such as wood, paper and cloth into plied products. They can also be used as flocking adhesives, binders for non-woven fabrics and soil treating agents.
- compositions of this invention can be applied to the substrates in any suitable manner as by dipping, padding, brushing, wiping, roller coating, spraying and the like.
- These compositions can also contain antioxidants, pigments, fillers, resins and plasticizers if so desired.
- Fillers can also include wheat flour, starches, soybean powder, wood powder, clay, kaolin, talc, titania, carbon, waterglass and the like.
- the polymer latex (1) is blended with the modified polyisocyanate emulsion (2) and the blend is applied to a surface (wood, plastic, fabric, metal, etc.) which then may be brought in contact with another surface which may be the same or another material.
- the adhesive is then allowed to cure by standing at ambient temperature. The cure can be accelerated if desired by application of heat or electromagnetic radiation.
- An emulsifier mixture was prepared using 2 g. of hexadecanol, 2 g. of a water soluble octyl phenoxy ethanol containing 10 moles of condensed ethylene oxide (triton ⁇ 100, Rohm & Hass Co.) and 13 g. of a 70% aqueous solution of sodium bis-tridecyl sulfosuccinate. The resulting mixture was stirred gently until it was homogenous.
- Example I (3) The adhesive and coating emulsion described in Example I (3) was evaluated on maple wood substrates.
- the adhesive was applied to maple sheets precut to the dimensions of 4" ⁇ 6.5" ⁇ 1/8" (wood grain in the 4" direction) at a spread rate of 28.85 pounds of solid per 100 sq. ft. of surface on one surface only.
- the sheets were pressed together for 20 hours at 175 pounds per square inch pressure at ambient temperature.
- the resulting panels were allowed to stand for three days at ambient temperature and they were then cut into test specimens measuring 4" ⁇ 3/8 ⁇ 1/8".
- the adhesive bonded maple wood specimens were conditioned in one of the following ways:
- a control adhesive made in accordance with U.S. Pat. No. 3,931,088 was also used in these tests.
- test (b) above the control was found to have a lapshear tensile of 470.9 p.s.i. and the adhesive formulation of Example I (3) was found to have a lapshear tensile of 824.5 p.s.i.
Abstract
Novel aqueous adhesive and coating compositions composed of (1) an aqueous emulsion (latex) or dispersion of a polymer or interpolymer of one or more vinyl monomers such as an emulsion of a copolymer of vinyl acetate and butyl acrylate and (2) an aqueous emulsion or dispersion of a polyisocyanate which has at least partially reacted with an alcohol having the formula ROH wherein R is a hydrocarbon radical having .[.at least one carbon atom.]. .Iadd.from six to 30 carbon atoms .Iaddend.and wherein the dispersion or emulsion (2) is stabilized with a combined surfactant and alcohol having the formula R' wherein R' is a hydrocarbon radical having at least one carbon atom are described.
Description
1. Field of the Invention
This invention relates to a water-base adhesive and coating agent which is especially useful for the coating and bonding of wood and other porous materials and which also has good pot life.
2. Description of the Art
At present, urea resins, melamine-urea co-condensation resins and phenolic resins are used for the adhesives in the manufacture of plywood. The evolution of formaldehyde from these materials has been found to have adverse environmental effects. This evolution of formaldehyde is difficult if not impossible to avoid in the production of plywood and for this reason substitute adhesives have been sought. Various non-formaldehyde yielding water-based adhesive compositions have been suggested but many of them have inadequate water resistance and/or short pot lives as well as other disadvantages. One such adhesive system has been suggested in U.S. Pat. No. 3,931,088 wherein there is disclosed an adhesive comprising (1) an aqueous solution of polyvinyl alcohol, and (2) a hydrophobic solution of an isocyanate compound in an organic solvent. Such compositions can also contain an anionic surface active agent. In contrast, the adhesive compositions of the present invention require no organic solvent and no polyvinyl alcohol in them.
The Official Digest (Of the Federation of Societies for Paint Technology), February 1960, page 213 et.seq. discloses the formation of "blocked" or heat-latent isocyanates with alcohol and subsequent reaction of these materials with amine bearing resins at about 150° C. to form coatings. No amine-bearing resins are required in our invention.
In accordance with the present invention there is provided a water-based adhesive and coating composition which has excellent pot life (in excess of 40 hours at room temperature) and produces coatings and adhesive bonds which have excellent strength and water resistance and are devoid of any formaldehyde or formalin evolution during use or storage. The compositions of this invention are made up of two main aqueous systems; namely, (1) an aqueous latex, emulsion or dispersion of a vinyl homopolymer or interpolymer of two or more vinyl monomers, and (2) an aqueous emulsion or dispersion of a polyisocyanate which has undergone at least partial reaction between some of its isocyanate groups with a monohydroxy alcohol having the formula ROH wherein R is a hydrocarbon radical containing at least one carbon atom and preferably R contains from six to thirty carbon atoms and wherein aqueous emulsion or dispersion (2) is stabilized with an emulsion stabilizer composed of a surfactant and an alcohol having the structure R'OH wherein R' is a hydrocarbon radical containing at least one carbon atom and more preferably wherein R' contains from six to thirty carbon atoms.
Vinyl monomers useful in the present invention include the methyl, ethyl, propyl, isopropyl butyl, isobutyl, pentyl, and other similar esters of acrylic, methacrylic, ethacrylic, propacrylic, chloroacrylic, and bromoacrylic acids; the phenyl, benzyl and phenethyl esters of the aforementioned acids; vinyl aromatic hydrocarbons, such as styrene, vinyl toluene, dimethyl styrenes, trimethyl styrenes, ethyl styrenes, methyl ethyl styrenes, t-butyl styrenes, chloromethyl styrenes, mono chloro styrenes, dichloro styrenes, cyanostyrenes, vinyl naphthalenes, n-vinyl carbazole and vinyl thiophenes; the vinyl esters of saturated aliphatic monocarboxylic acids such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl valerate; vinyl versatate; alkyl vinyl ketones such as methyl vinyl ketone, ethyl vinyl ketone and methyl isopropenyl ketone; diesters of itaconic acid, maleic acid and fumaric acid; alkyl esters of unsaturated monocarboxylic acids as well as the acids themselves; nitriles containing a single vinyl group such as acrylonitrile and methacrylonitrile. The use of polyvinyl monomers such as divinyl-benzene, vinyl acrylate, butadiene, isoprene, and chloroprene is within the scope of the invention.
Particularly useful homopolymers and interpolymers of vinyl monomers for the purpose of this invention can include polymers and interpolymers of one or more monomers including vinyl acetate, vinyl chloride, vinylidene chloride, styrene, vinyl toluene, acrylonitrile, methacrylonitrile, acrylic ester, methacrylic esters, ethylene, isobutylene, butadiene, and isoprene.
Polyisocyanates useful in this invention are organic isocyanates having at least two isocyanate groups per molecule. The polyisocyanates can be of low, high or intermediate molecular weight and can be any of a wide variety of organic polyisocyanates including ethylene diisocyanate, trimethylene diisocyanate, dodecamethylene diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate trimer, tetraethylene diisocyanate, pentamethylene diisocyanate, propylene-1,2-diisocyanate, 2,3-dimethyl tetramethylene diisocyanate, butylene-1,2-diisocyanate, butylene-1,3-diisocyanate, 1,4-diisocyanato cyclohexane, cyclopentene 1,3-diisocyanate, p-phenylene diisocyanate, 1-methyl phenylene-2,4-diisocyanate, naphthalene-1,4-diisocyanate, O,O-toluene diisocyanate, diphenyl-4,4'-diisocyanate, benzene-1,2,4-triisocyanate, xylylene-1,4-diisocyanate, xylylene-1,3-diisocyanate, 4,4', diphenylene methane diisocyanate, 4,4'-diphenylene propane diisocyanate, 1,2,3,4-tetraisocyanato butane, butane-1,2,3-triisocyanate, polymethylene polyphenyl isocyanate, and other polyisocyanates having an isocyanate functionality of at least two as more full disclosed in U.S. Pat. Nos. 3,350,362 and 3,382,215. Polyisocyanates which are polymeric in nature including isocyanate prepolymers of all types are included in this invention.
Alcohols of the type ROH and R'OH mentioned above in which R and R' are independently selected which are most useful in this invention are preferably aliphatic mono alcohols including n-hexyl alcohol, n-heptyl alcohol, n-octyl alcohol, n-nonyl alcohol, n-decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, isohexyl alcohol, 2-ethyl hexanol, 2-ethyl isohexanol, iso octyl alcohol, isononyl alcohol, isodecyl alcohol, isotridecyl alcohol, isocetyl alcohol, isostearyl alcohol, oleyl alcohol, linoleyl alcohol and the like.
The surfactants which in combination with the alcohols R'OH which are useful in stabilization of the at least partially modified polyisocyanate emulsions of this invention can be one or more of any of the well-known anionic, cationic and nonionic surfactants. It is usually advantageous to use anionic surfactants because such surfactants are most commonly used in the preparation of the vinyl polymer latices used in this invention and for purposes of compatibility the same type of surfactant is desired in both aqueous systems (1) and (2) of this invention. Anionic surfactants which are particularly useful in this invention include alkyl sulfonates, sulfonated aliphatic amines and amides, diphenyl sulfonates, ethoxylated fatty acids, lignin and lignin derivatives, olefin sulfonates, alkyl and inorganic phosphates, polyamine and carboxylic acids, sulfosuccinates, and alcohol sulfates, ethoxylated alcohol sulfates, sulfates and sulfonates of ethoxylated alkyl phenols, sulfates on fatty esters, sulfates and sulfonates of oils and fatty acid, alkyl aryl sulfonates, sulfonates of benzene, toluene, and xylene, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecyl benzenes, sulfonates of naphthalene and alkyl naphthalenes, sulfonates of petroleums, tridecyl and dodecyl benzene sulfonic acids, taurates, and the like.
The vinyl polymer latex which constitutes part (1) of this invention can be made by well-known emulsion polymerization techniques involving the polymerization of the vinyl monomer or monomers in aqueous emulsion with a free radical polymerization initiator. Emulsion stability is maintained by means of the usual surfactants emulsion stabilizers, suspending agents and the like as is well known to those skilled in the art.
The organic phase of the polyisocyanate emulsion (2) of this invention is composed of at least one polyisocyanate in which at least some of the isocyanate groups have been allowed to react with an alcohol ROH to form an at least partially modified isocyanate. This organic phase is prepared by the treatment of from about 0.032 to 0.22 equivalents of ROH per isocyanate equivalent of the polyisocyanate. The emulsifier component in (2) can be present in from about 1 to 3 parts by weight of the modified isocyanate organic phase with the ratio of R'OH to surfactant in the emulsifier falling in the range of about 2 to 4%.
The alcohol modified polyisocyanate emulsions (2) of this invention can be prepared by conventional methods. Batch preparation of the emulsions can be effected by adding a mixture of the modified isocyanate and emulsifying agent to vigorously agitated water or conversely, the water may be added to the isocyanate emulsifier mixture. The alcohol modified polyisocyanate can also be added to the aqueous emulsifier mixture. Very uniform emulsions are obtained by using homogenizing equipment, but any high speed mixing device can be used. Continuous preparation of the emulsions can be performed by feeding the components at controlled rates into a high shear mixing zone. Although it is preferred that these emulsions contain from about 65-75% by weight of the organic component, the concentrated emulsions can also be diluted to any desired concentration by the addition of water. The emulsions, however, can be prepared directly at low concentrations if so desired.
The compositions of the present invention composed of mixtures of (1) and (2) parts as described above exhibit tenacious adhesions to fibrous, non-fibrous, porous and non-porous, flexible and rigid, metallic and non-metallic, polymeric, leather, cork, wood and glass surfaces.
In addition to their use as an adhesive and coating agents the compositions of this invention are ideally suited for use as impregnants, saturants or sealants for porous substances of many types. Where flexible substrates are involved, the in situ reaction of the reactive components confers strength and rigidity. In the case of moisture sensitive substrates, the presence of the compositions of this invention decreases water sensitivity and this makes them particularly valuable for treating wood, paper, paper board, textiles, and the like. In addition to applications to paper, the compositions of this invention can be used for stiffening, reinforcing, water-proofing, or modifying a variety of foam plastic fabrics and specialty papers derived from natural and synthetic fibers such as asbestos, cellulose, flax, nylon and the like. The compositions of this invention can be used to seal wood and porous masonry such as concrete, mortar, plaster, stone and brick. The compositions of this invention can also be used as adhesives for binding wood chips, ground leather, ground cork, sand, glass fibers, carbon fibers and similar substances into sheet or molded forms. They are also useful as adhesives for laminating sheet materials such as wood, paper and cloth into plied products. They can also be used as flocking adhesives, binders for non-woven fabrics and soil treating agents.
The coating adhesive compositions of this invention can be applied to the substrates in any suitable manner as by dipping, padding, brushing, wiping, roller coating, spraying and the like. These compositions can also contain antioxidants, pigments, fillers, resins and plasticizers if so desired. Fillers can also include wheat flour, starches, soybean powder, wood powder, clay, kaolin, talc, titania, carbon, waterglass and the like.
In this practice of this invention the polymer latex (1) is blended with the modified polyisocyanate emulsion (2) and the blend is applied to a surface (wood, plastic, fabric, metal, etc.) which then may be brought in contact with another surface which may be the same or another material. The adhesive is then allowed to cure by standing at ambient temperature. The cure can be accelerated if desired by application of heat or electromagnetic radiation.
The invention is further illustrated in the following examples:
(1) An aqueous latex of a vinyl acetate n-butyl acrylate copolymer (85/15 parts by weight, respectively) having a solids content of approximately 64% by weight was employed.
(2) An emulsifier mixture was prepared using 2 g. of hexadecanol, 2 g. of a water soluble octyl phenoxy ethanol containing 10 moles of condensed ethylene oxide (triton×100, Rohm & Hass Co.) and 13 g. of a 70% aqueous solution of sodium bis-tridecyl sulfosuccinate. The resulting mixture was stirred gently until it was homogenous.
(b) A mixture of 200 g. of a polymethylene polyphenyl isocyanate having an isocyanate content of about 31.5% (Mondur MR, Mobay Chemical Corp.) and 60 g. of isocetyl alcohol (a 23.08% solution of isocetyl alcohol in Mondur MR) was shaken in a closed bottle until the resulting exotherm subsided.
(c) To grams of the emulsifier described in 2 (a) above were homogenized together with 50 g. of deionized water. To this aqueous surfactant dispersion were added 100 g. of the modified isocyanate described in 2 (b) above and this mixture was homogenized by stirring at about 1000 RPM. (3) A mixture of 100 g. of the latex described in (1) above and 22.01 g. of the modified isocyanate emulsion described in 2 (c) above was made and constituted an adhesive formulation in accordance with this invention.
The adhesive and coating emulsion described in Example I (3) was evaluated on maple wood substrates. The adhesive was applied to maple sheets precut to the dimensions of 4"×6.5"×1/8" (wood grain in the 4" direction) at a spread rate of 28.85 pounds of solid per 100 sq. ft. of surface on one surface only. The sheets were pressed together for 20 hours at 175 pounds per square inch pressure at ambient temperature. The resulting panels were allowed to stand for three days at ambient temperature and they were then cut into test specimens measuring 4"×3/8×1/8".
The adhesive bonded maple wood specimens were conditioned in one of the following ways:
(a) half the specimens were lapshear (ASTM D2339-70) tested at ambient conditions the fourth day;
(b) one the third day the remaining half of the samples were immersed into 60° C. deionized water for four hours, subsequently dried at 42' C. for 19 hours and then lapshear tested on the fourth day.
Shear testing on the test samples was performed on an Instron machine. Tensile shear strength and work to break were evaluated at a cross head speed of 0.1 inches per minute and a chart speed of 5.0 inches per minute.
A control adhesive made in accordance with U.S. Pat. No. 3,931,088 was also used in these tests. In test (a) above the control adhesive formulation was found (average of at least four test specimens) to have a lapshear tensile of 861.3 p.s.i. whereas the adhesive formulation of Example I (3) was found (average of at least four test specimens) to have a lapshear tensile of 1,532.2 p.s.i. In test (b) above the control was found to have a lapshear tensile of 470.9 p.s.i. and the adhesive formulation of Example I (3) was found to have a lapshear tensile of 824.5 p.s.i.
when the adhesive formulation described in Example I (3) was aged at room temperature for about 30 days before use in test (a) above, essentially no change occurred in the lapshear tensile.
(1) An aqueous latex of styrene/butadiene (60/40 parts by weight, respectively) copolymer having a solids content at about 48% by weight was used.
(2) (a) An emulsifier was prepared as described in 2 (a) of Example I above. (b) A 16.7% isocetyl alcohol solution in Mondur MR was prepared as in 2 (b) of Example I above.
(c) The homogenized isocyanate preparation of 2 (b) above was prepared in the same manner as described in 2 (c) in Example I above.
(3) A mixture of 100 g. of the latex in (1) above, 0.4 g. of Gantrez M154 (poly methyl vinyl ether from GAF Corp.) and 13.2 g. of the modified isocyanate emulsion described in 2 (c) above formed the adhesive composition of this Example.
When the adhesive (3) of this Example was tested by the procedure of Example II (a) similar results in the lapshear test were observed and the shelf life of this adhesive formulation was found to be excellent.
1. An aqueous latex that is identical to that described in (1) of Example I above was utilized.
(2) (a) An emulsifier was prepared by the method described in 2 (a) of Example I above.
(b) A mixture of 200 g. of hexamethylene diisocyanate trimer (Desmodur KL 5-2444, Mobay Chemical Corp. having an isocyanate content of about 20%, and 20 g. of isocetyl alcohol. (A 9% solution of isocetyl alcohol in the polyisocyanate was shaken in a closed container until the mixture was homogenous (about 6 hours).
(c) The modified isocyanate as described in (b) above was homogenized in water with emulsifier as described in 2 (c) of Example I above.
(3) A mixture of 100 g. of the latex described in (1) above and 15.43 g. of the isocyanate emulsion described in 2 (c) above constituted an adhesive within the scope of the invention.
When the adhesive described in (3) of this Example was tested by the procedure described in Example II the lapshear tensile in (a) was found to be 1,392.4 p.s.i. with 71% wood failure (indicating that the adhesive bond was stronger than the cohesive bonding of the wood itself) and the lapshear tensile in test (b) was 650.7 p.s.i.
Claims (7)
1. A composition of matter comprising a mixture of an aqueous latex emulsion or dispersion of
(a) a member selected from the group consisting of a homopolymer of a vinyl monomer and an interpolymer of two or more vinyl monomers, and
(b) a polyisocyanate which has undergone at least partial reaction of some of its isocyanate groups with a .[.alcohol.]..Iadd.C6 -C30 monohydroxy alkanol.Iaddend..
2. The composition of claim 1 wherein (b) is stabilized with an emulsion stabilizer composed of a surfactant and an alcohol having the structure R'OH wherein R' is a hydrocarbon radical having at least 1 carbon atom.
3. The composition of claim 1 wherein the monohydroxy alcohol in (b) is .[.one having the formula ROH wherein R is a hydrocarbon radical containing at least one carbon atom.]. .Iadd.selected from the group consisting of n-hexyl alcohol, n-heptyl alcohol, n-octyl alcohol, n-nonyl alcohol, n-decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, arachidyl alcohol, behenyl alcohol, isohexyl alcohol, 2-ethyl hexanol, 2-ethyl isohexanol, isooctyl alcohol, isononyl alcohol, isodecyl alcohol, isotridecyl alcohol, isocetyl alcohol, isostearyl alcohol, oleyl alcohol, and linoleyl alcohol. .Iaddend.
4. The composition of claim 1 wherein (a) is an aqueous latex of a homopolymer of an interpolymer of a monomer or monomers selected from the group consisting of vinyl acetate, vinyl chloride, vinylidene chloride, styrene, vinyl toluene, acrylonitrile, methacrylonitrile, acrylic esters, methacrylic esters, ethylene, isobutylene, butadiene and isoprene.
5. The composition of claim 4 wherein the polyisocyanate of .[.(2).]. .Iadd.(b) .Iaddend.is a member selected from the group consisting of ethylene diisocyanate, trimethylene, diisocyanate, dodecamethylene diisocyanate, hexamethylene diisocyanate, hexamethylene diisocyanate trimer, tetraethylene diisocyanate.Iadd., .Iaddend.pentamethylene diisocyanate, propylene-1,2-diisocyanate, 2,3-dimethyl tetramethylene diisocyanate, butylene-1,2-diisocyanate, butylene-1,3-diisocyanate, 1,4-diisocyanato cyclohexane, cyclopentene 1,3-diisocyanate, p-phenylene diisocyanate, 1-methyl phenylene-2,4-diisocyanate, naphthalene-1,4-diisocyanate, O,O,-toluene diisocyanate, diphenyl-4,4'-diisocyanate, benzene-1,2,4-triisocyanate, xylylene-1,4-diisocyanate, xylylene-1,3-diisocyanate, 4,4'-diphenylene methane diisocyanate, 4,4'-diphenylene propane diisocyanate, 1,2,3,4-tetraisocyanato butane, butane-1,2,3-triisocyanate, polymethylene polyphenyl isocyanate, and polymeric polyisocyanates.
6. A process comprising applying to at least one surface of a material a mixture of an aqueous latex, emulsion or dispersion of
(a) a member selected from the group consisting of a homopolymer of a vinyl monomer and an interpolymer of two or more vinyl monomers, and
(b) a polyisocyanate which as undergone at least partial reaction of some of its isocyanate groups with a .Iadd.C6 -C30 monohydroxy .[.alcohol.]. .Iadd.alkanol. .Iaddend.
7. A process which comprises (1) treating at least one surface of a material with a mixture of an aqueous latex, emulsion or dispersion of (a) a member selected from the group consisting of a homopolymer of a vinyl monomer and an interpolymer of two or more vinyl monomers, and (b) a polyisocyanate which has undergone at least partial reaction of some of its isocyanate groups with a .Iadd.C6 -C30 .Iaddend. monohydroxy .[.alcohol.]. .Iadd.alkanol. .Iaddend.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US06/759,910 USRE34093E (en) | 1982-05-24 | 1985-07-29 | Aqueous adhesive compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/381,620 US4396738A (en) | 1982-05-24 | 1982-05-24 | Aqueous adhesive compositions |
US06/759,910 USRE34093E (en) | 1982-05-24 | 1985-07-29 | Aqueous adhesive compositions |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US06/381,620 Reissue US4396738A (en) | 1982-05-24 | 1982-05-24 | Aqueous adhesive compositions |
Publications (1)
Publication Number | Publication Date |
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USRE34093E true USRE34093E (en) | 1992-10-06 |
Family
ID=27009463
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US06/759,910 Expired - Fee Related USRE34093E (en) | 1982-05-24 | 1985-07-29 | Aqueous adhesive compositions |
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US (1) | USRE34093E (en) |
Cited By (4)
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US5856404A (en) * | 1994-02-08 | 1999-01-05 | Schnee-Morehead, Inc. | Back bedding sealant composition |
US6084024A (en) | 1996-11-12 | 2000-07-04 | Air Products And Chemicals, Inc. | Water borne pressure sensitive adhesive compositions derived from copolymers of higher vinyl esters |
US6153690A (en) | 1996-05-29 | 2000-11-28 | Rohm And Haas Company | Method of producing isocyanate-modified latex polymer |
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