JPS6312110B2 - - Google Patents
Info
- Publication number
- JPS6312110B2 JPS6312110B2 JP12719980A JP12719980A JPS6312110B2 JP S6312110 B2 JPS6312110 B2 JP S6312110B2 JP 12719980 A JP12719980 A JP 12719980A JP 12719980 A JP12719980 A JP 12719980A JP S6312110 B2 JPS6312110 B2 JP S6312110B2
- Authority
- JP
- Japan
- Prior art keywords
- polyamide
- polyester
- acid
- parts
- resin
- 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
Links
- 229920005989 resin Polymers 0.000 claims description 35
- 239000011347 resin Substances 0.000 claims description 35
- 239000004952 Polyamide Substances 0.000 claims description 33
- 229920002647 polyamide Polymers 0.000 claims description 33
- 229920000728 polyester Polymers 0.000 claims description 19
- 229920002396 Polyurea Polymers 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229920002635 polyurethane Polymers 0.000 claims description 11
- 239000004814 polyurethane Substances 0.000 claims description 11
- 239000004831 Hot glue Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- HTZNYVXKBVMMFC-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid sulfane Chemical compound S.OC(=O)C1=CC=CC(C(O)=O)=C1 HTZNYVXKBVMMFC-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 239000000853 adhesive Substances 0.000 description 27
- 230000001070 adhesive effect Effects 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 13
- 229920001225 polyester resin Polymers 0.000 description 12
- 239000004645 polyester resin Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 238000005108 dry cleaning Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- 239000004744 fabric Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- -1 diisocyanate compound Chemical class 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 229920006122 polyamide resin Polymers 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 4
- 239000001095 magnesium carbonate Substances 0.000 description 4
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920005749 polyurethane resin Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229940009827 aluminum acetate Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000007731 hot pressing Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000004027 organic amino compounds Chemical class 0.000 description 2
- 239000002245 particle Substances 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
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 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
- 210000002268 wool Anatomy 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- GZZLQUBMUXEOBE-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diol Chemical compound OCCC(C)CC(C)(C)CO GZZLQUBMUXEOBE-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
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- QNKRHLZUPSSIPN-UHFFFAOYSA-N 2-ethyl-2-(2-methylpropyl)propane-1,3-diol Chemical compound CCC(CO)(CO)CC(C)C QNKRHLZUPSSIPN-UHFFFAOYSA-N 0.000 description 1
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
- JFFYKITVXPZLQS-UHFFFAOYSA-N 2-methylidenepropane-1,3-diol Chemical compound OCC(=C)CO JFFYKITVXPZLQS-UHFFFAOYSA-N 0.000 description 1
- YZTJKOLMWJNVFH-UHFFFAOYSA-N 2-sulfobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O YZTJKOLMWJNVFH-UHFFFAOYSA-N 0.000 description 1
- RAADBCJYJHQQBI-UHFFFAOYSA-N 2-sulfoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(S(O)(=O)=O)=C1 RAADBCJYJHQQBI-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- SDGNNLQZAPXALR-UHFFFAOYSA-N 3-sulfophthalic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1C(O)=O SDGNNLQZAPXALR-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- LYKRIFJRHXXXDZ-UHFFFAOYSA-N 4-(4-hydroxybutoxy)butan-1-ol Chemical compound OCCCCOCCCCO LYKRIFJRHXXXDZ-UHFFFAOYSA-N 0.000 description 1
- HBLRZDACQHNPJT-UHFFFAOYSA-N 4-sulfonaphthalene-2,7-dicarboxylic acid Chemical compound OS(=O)(=O)C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 HBLRZDACQHNPJT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 description 1
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 1
- YWMLORGQOFONNT-UHFFFAOYSA-N [3-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC(CO)=C1 YWMLORGQOFONNT-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- SSFGHKDDKYEERH-UHFFFAOYSA-N [6-(hydroxymethyl)naphthalen-2-yl]methanol Chemical compound C1=C(CO)C=CC2=CC(CO)=CC=C21 SSFGHKDDKYEERH-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OREAFAJWWJHCOT-UHFFFAOYSA-N dimethylmalonic acid Chemical compound OC(=O)C(C)(C)C(O)=O OREAFAJWWJHCOT-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- UHNWOJJPXCYKCG-UHFFFAOYSA-L magnesium oxalate Chemical compound [Mg+2].[O-]C(=O)C([O-])=O UHNWOJJPXCYKCG-UHFFFAOYSA-L 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 229910000157 magnesium phosphate Inorganic materials 0.000 description 1
- 229960002261 magnesium phosphate Drugs 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- HPBJPFJVNDHMEG-UHFFFAOYSA-L magnesium;octanoate Chemical compound [Mg+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HPBJPFJVNDHMEG-UHFFFAOYSA-L 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Description
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The present invention relates to novel hot melt adhesive compositions. Conventionally, polyamide resin, polyester resin, etc. have been known as adhesives for textile materials.
When polyamide resin adhesives are used for textile fabrics, there is a disadvantage that the adhesive strength after washing with water is significantly reduced, and when polyester adhesives are used, the adhesive strength after dry cleaning is significantly reduced. It is acknowledged that there are shortcomings. For this reason, there has been a long-awaited new, durable hot melt adhesive that can withstand both wet washing and dry cleaning. However, as a result of intensive research, the present inventors have improved the shortcomings of conventionally known hot melt adhesives for textile materials, and have successfully maintained their excellent initial adhesion to textile materials, even after washing with water and dry cleaning. We have discovered a new adhesive composition that is highly effective, and have completed the present invention. That is, the present invention provides ``A) a --SO 3 M group (M in the group is hydrogen, sodium, or (represents potassium atom)
(B) oxides, hydroxides, or organic or inorganic salts of metals selected from Groups 2 and 3 of the Periodic Table for 100 parts by weight of polyester, polyamide, polyurethane, or polyamide polyurea resin having 0.5 to 20 parts by weight of a novel hot melt adhesive composition. The adhesive composition of the present invention maintains excellent initial adhesion to textile materials even after washing with water and dry cleaning. Substantially at least 1 in the molecule of the present invention
A polyester, polyamide, polyurethane or polyamide polyurea resin having an SO 3 M group is a polyester, polyamide, polyurethane or polyamide polyurea resin that is bonded to an aromatic nucleus.
Various polycondensation resins obtained using monomers such as dicarboxylic acids, diols, or condensable derivatives thereof having SO 3 M groups are shown. Examples of such monomers include sulfoisophthalic acid, sulfoterephthalic acid, sulfophthalic acid, 4-sulfonaphthalene-2,7-dicarboxylic acid, or compounds in which the carboxyl group of these compounds is esterified with a lower alcohol. , or their sodium salts, potassium salts, etc.
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ããExamples include [Formula]. Most preferably used in the present invention are 5-sulfonodium isophthalate and 5-sulfonodium dimethyl isophthalate. In the present invention, substantially at least one
The method for producing polyester, polyamide, polyurethane or polyamide polyurea resin having -SO 3 M groups bonded to aromatic nuclei is not particularly limited. For example, as a polyester resin, a compound having at least two carboxylic acid groups in the molecule or a lower alkyl ester thereof in a carboxylic acid, diol, or a condensable derivative thereof having an -SO 3 M group bonded to the aromatic nucleus is used. 4,000 to 30,000, which is obtained by adding a compound having at least two hydroxyl groups in the molecule and condensation polymerizing it by a known method by dehydration, dealcoholization, or deglycol reaction.
Polyester resins having a number average molecular weight of Examples of polyamide resins include dicarboxylic acids or lower alkyl ester compounds thereof having -SO 3 M groups bonded to aromatic nuclei, and organic amino compounds having at least two primary and/or secondary amino groups in the molecule. Examples include polyamide resins made by adding and condensation polymerizing. Examples of polyurethane resins having -SO 3 M groups bonded to aromatic nuclei suitable for the present invention include -SO 3 M groups bonded to aromatic nuclei.
A compound having at least two carboxylic acid groups in the molecule or a lower alkyl ester thereof and a compound having at least two hydroxyls in the molecule to a dicarboxylic acid, a diol, or a condensable derivative thereof having -OH/ An organic diisocyanate compound is added to a polyester polyol with a molecular weight of 500 to 3,000, which has an SO 3 M group in the molecule whose COOR (R is H or an alkyl group) ratio is condensed with an excess of hydroxyl groups, and whose terminal group is a hydroxyl group. Examples include polyurethane resins that have been made into polymers by adding Further examples of polyamide polyurea resins include dicarboxylic acids or lower alkyl esters thereof having -SO 3 M groups bonded to aromatic nuclei, and organic amino acids having at least two primary and/or secondary amino groups in the molecule. Compounds - NHR / -
-SO 3 M group is present in the molecule obtained by condensation polymerization with COOR (R is H or alkyl group) ratio in excess of amino groups,
Molecular weight 500-3000 with terminal group being hydroxyl group
Examples include polyamide polyurea resins made by adding organic diisocyanate compounds to polyamide polyamines to polymerize them. In the present invention, compounds having at least two carboxylic acid groups in the molecule or lower alkyl of these carboxylic acids that can be used in combination with dicarboxylic acids, diols, or condensable derivatives thereof having an -SO 3 M group bonded to an aromatic nucleus. Examples of esters include oxalic acid, malonic acid, dimethylmalonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, sebacic acid, fumaric acid, maleic acid, itaconic acid, 1,3-cyclohexanedicarboxylic acid, 1,4 -cyclohexanedicarboxylic acid,
Phthalic acid, terephthalic acid, isophthalic acid,
These include carboxyl compounds such as 2,5-naphthalene dicarboxylic acid and ester compounds of lower alcohols thereof, and particularly preferably used are terephthalic acid, isophthalic acid, and their dimethyl esters. Furthermore, compounds having at least two hydroxyl groups that can be used in the present invention include:
For example, ethylene glycol, 1,2-propanediol, 1,3-propanediol, butanediols, especially 1,4-butanediol, pentanediol, especially 1,5-pentanediol, hexanediol, especially 1,6 -Hexanediol, others 1,10-decanediol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, tripropylene glycol, polyoxyethylene glycol with a molecular weight of 200 to 2000, bis-(4-hydroxybutyl) ether, 2-methylene-1,3
-Propanediol, 2,4-dimethyl-2-ethylhexane-diol-1,3,2-ethyl-
2-butyl-1,3-propanediol, 2,2
-dimethyl-1,3-propanediol, 2-ethyl-2-isobutyl-1,3-propanediol, 2,2,4-trimethyl-1,6-hexanediol, 1,3-dihydroxycyclohexane, 1,4 -dihydroxycyclohexane, 1,
4-bis(hydroxymethyl)cyclohexane,
1,3-bis(hydroxymethyl)cyclohexane, 1,2-bis(hydroxymethyl)cyclohexane, 1,4-bis(hydroxymethylbenzene), 1,3-bis(hydroxymethyl)benzene, 2,6-bis (Hydroxymethyl)naphthalene and also diphenyls converted to araliphatic pishydroxy compounds by bilateral reaction with e.g. ethylene oxide, e.g. etc. can be mentioned. In addition, in the present invention, examples of organic amino compounds having at least two primary and/or secondary amino groups in the molecule used in the synthesis of polyamide resins and polyamide polyurea resins include ethylenediamine, hexamethylenediamine,
Primary diamines such as 1,4-cyclohexyldiamine-propylene diamine, 1,3-diaminopropane, hydrazine, isophorone diamine, N
Examples include amines such as -methylhydrazine, N-hydroxyethylhydrazine, piperazine, and aminoethylpiperazine, and polyamines such as diethylenetriamine, triethylenetetramine, and tetraethylenepentamine. Further, as the compound having at least two isocyanate groups used in the production of polyurethane resins and polyamide polyurea resins, aromatic, aliphatic, and alicyclic compounds can be used. For example, hexamethylene-1,6- Diisocyanate, butane-1,4-
Diisocyanate, dicyclohexylmethane diisocyanate, cyclohexane-1,4-diisocyanate, xylylene diisocyanate, isophorone diisocyanate, 1,5-naphthalene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethyl-methane diisocyanate, Diisocyanate compounds such as di- and tetraalkylene diisocyanate, 4,4'-dibenzyl diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, and tolylene diisocyanate are mentioned. Furthermore, compounds having two or more functional groups capable of reacting with these isocyanate compounds and isocyanate groups, such as relatively low molecular weight compounds having both terminal groups having a hydroxyl group, a carboxyl group, or a primary or secondary amino group, may be used. Also included are prepolymers having active isocyanate groups at both end groups, which are obtained by reacting a polyether, polyester, polyesteramide, or polyamide compound with an isocyanate compound in excess of the stoichiometric amount. The number average molecular weight of the resin obtained in the present invention is
Must be in the range 4000-30000. If the number average molecular weight of the obtained resin is lower than 4000, the adhesive strength of the obtained resin will be low and it will be difficult to use it as a hot melt adhesive for fiber materials, which is not preferable. Furthermore, if the number average molecular weight of the obtained resin is higher than 30,000, the viscosity of the obtained resin increases to such an extent that it is difficult to handle, which is not preferable. The preferred number average molecular weight of the resin obtained in the present invention is in the range of 5,000 to 20,000. Further, the resin obtained in the present invention has -SO 3 M substantially bound to at least one aromatic nucleus in the molecule.
Although it is characterized by containing groups, it is common for the number of --SO 3 M groups to be substantially 1.5 to 4 in one molecule from the viewpoint of processing effects and economical efficiency of the resin. In the present invention, particularly preferred resins as hot melt adhesives for fibers have a softening temperature of 90°C to 140°C,
It is a resin having physical properties of a melt index of 1 to 50 g/10 minutes and a temperature of 150°C, among which polyester resin is the most common and preferred. The thus obtained polyester, polyamide, polyurethane or polyamide polyurea resin having SO 3 M groups
0.5 to 20 parts by weight, preferably 1 to 15 parts by weight of metal oxides, hydroxides, or organic or inorganic salts of metals selected from Groups 2 and 3 of the periodic table per 100 parts by weight. Added. Representative metals of Groups 2 and 3 of the periodic table in the present invention include magnesium, calcium, zinc, aluminum, etc., and examples of preferred metal compounds in the present invention include magnesium oxide, calcium oxide, zinc oxide, Oxides such as aluminum oxide, hydroxides such as magnesium hydroxide and calcium hydroxide, carbonates such as magnesium carbonate, calcium carbonate, and zinc carbonate, and other hydrochlorides, nitrates, sulfates, and phosphorus of these metals. Various inorganic salts such as acid salts, magnesium acetate, magnesium octylate, magnesium stearate,
Contains various organic salts such as magnesium oxalate. Metal compounds particularly preferably used in the present invention are carbonates such as magnesium carbonate and calcium carbonate, and phosphates such as magnesium phosphate and calcium phosphate. Substantially at least 1 in the molecule of the present invention
The method of adding the metal compound to the polyester, polyamide, polyurethane, or polyamide polyurea resin having -SO 3 M groups bonded to aromatic nuclei is not particularly limited, and the metal compound may be added during the synthesis of these resins or immediately after the synthesis is completed. Alternatively, it may be mixed with the above-mentioned resins immediately before or during the hot-melt bonding process using these resins. Preferably, the above-mentioned polyester, polyamide, polyurethane or polyamide polyurea resin having an -SO 3 M group bonded to the aromatic nucleus is converted into a form such as powder, pellets, dispersion, or emulsion, and then the above-mentioned metal compound powder is obtained. A uniform mixture of water, aqueous solution, or aqueous dispersion is used for adhesion. In the present invention, there are no particular limitations on the adhesion method; generally, a powder or dispersion adhesive is applied to a woven fabric, the same or different types of woven fabric are layered, and then ironing, hot pressing, hot pressing, etc. Adhesion is performed by heating and softening using a roller or other means. In this case, when the powder is in the form of powder, coating is performed using a dotting machine, scattering machine, etc., and the dispersion is applied by spraying, knife coating, etc. Woven fabrics include synthetic fibers such as polyester, polyamide, and acrylic, natural fibers such as wool and cotton, inorganic fibers such as glass fiber and asbestos, and blends thereof.It is also used for adhesion of badges, marks, etc. be able to. According to the adhesive of the present invention, it is possible to obtain an extremely excellent adhesive fabric that can withstand both water washing and dry cleaning. In addition to the above adhesives for fiber materials, the adhesive obtained in the present invention can also be used as a hot melt adhesive for plastics, metals, glass, leather, rubber, wood, paper, etc. It is also possible to add appropriate amounts of an antioxidant, an anti-slip agent, an anti-blocking agent and a tackifying agent to the adhesive of the present invention, if necessary. Next, the present invention will be specifically described with reference to Examples, but the present invention is not limited to these Examples. Note that "parts" and "%" shown below are based on weight unless otherwise specified. Synthesis Example (Synthesis of E-1 to 4, C-1 to 2) 664 parts of isophthalic acid, 83 parts of terephthalic acid, 372 parts of ethylene glycol, 148 parts of 5-sulfonodium dimethyl isophthalate, and 0.135 parts of sodium acetate were added to a reaction pot. heated from 140°C to 200°C in a nitrogen stream for about 4 hours, then heated to 240°C.
â and a polycondensation reaction was carried out under reduced pressure of 10 mmHg for about 6 hours to synthesize a polyester resin (E-1) having -SO 3 Na group bonded to an aromatic nucleus in the molecule. The acid value of the obtained polyester resin (E-1) was 4.4, and the molecular weight was 6,600. In addition, the softening temperature of the obtained polyester resin (E-1) is
It had a melt index of 12 g/10 minutes at 105°C and 150°C. Similarly, copolyester resins (E-2 to E-4) whose polymer compositions are shown in Table 1 were synthesized. Further, as comparative examples, copolymerized polyester resins shown by C-1 and C-2 were synthesized. Examples 1 to 6, Comparative Examples 1 to 3 Polyester resin E-1 obtained in Synthesis Example
4. C-1 to 2 are crushed by frozen crushing method,
Micronization was performed to have a particle size of 200 mesh or less. After adding oxides, hydroxides, or organic or inorganic salts of metals selected from Groups 2 and 3 of the periodic table to this powdered polyester resin as shown in Table 2, a Henschel mixer is used. The mixture was dispersed uniformly using a . The obtained powder composition is coated onto a polyester spun core by a powder coating method in an amount of 5 to 15 g/
Resin was deposited in an amount of m2 . The obtained adhesive interlining was press-bonded to a polyester/cotton = 65/35 blended broadcloth under the conditions of a press temperature of 150°C, a press pressure of 0.30 kg/cm 2 , and a press steaming/second press of 9 seconds. Initial adhesive strength for the bonded base fabric,
The adhesive strength after the dry cleaning test according to JIS-L-1089 and the adhesive strength after washing with water were measured using an autograph at a peeling speed of 30 cm/min. The test results are shown in Table 2. It was found that processed fabrics bonded with ordinary polyester resin adhesives (C-1, C-2) had relatively good water resistance to washing, but could not withstand dry cleaning at all.
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ããã[Table] Example 7, Comparative Example 4 394 parts of isophthalic acid, 394.5 parts of terephthalic acid,
708 parts of 1,6-hexamethylene glycol, 5-
74 parts of sulfonodium dimethyl isophthalate,
and 0.135 parts of sodium acetate into the reaction vessel,
The temperature was raised from 140°C to 220°C in a nitrogen stream over 8 hours, and then maintained at 220°C to remove the OH in the resin.
Continuing the polycondensation reaction while measuring the value and acid value,
A polyester resin with an OH value of 55.9 and an acid value of 0.2 and having -SO 3 Na groups in its molecules was created. 377.7 parts of the obtained polyester, 34.8 parts of ethylene glycol, and toluene diisocyanate (2,4-,2,6
- isomer ratio = 80/20) were mixed and heated to obtain a polyurethane mass with a molecular weight of 15,000.
This polyurethane lump was pulverized by a freeze pulverization method and pulverized to have a particle size of 200 mesh or less. This powdered polyurethane resin 100%
5 parts of magnesium carbonate powder were added to the mixture, and the mixture was uniformly dispersed using a Henschel mixer. The obtained powdered resin composition was spread on the surface of a nylon nonwoven fabric in an amount of 8 g/m 2 and fixed by heat to prepare a fused interlining. This fused interlining was fused to a tropical fabric (55% wool, 45% polyester blend) by dry heat pressing at 140°C for 10 seconds. The initial adhesive strength of this adhesive fabric is 2.3Kg/inch, and the adhesive strength of the fusion interlining after dry cleaning test and water washing is 1.92Kg/inch and 1.98Kg/inch, respectively, which is an extremely excellent adhesive strength. was holding it. For comparison, a fused interlining was made under the same conditions as above without adding magnesium carbonate powder, and an adhesion test was conducted.The adhesion test was 1.45 kg/inch after washing with water, and 1.37 kg/inch after dry cleaning.
A considerable decrease of Kg/inch was observed. The results are shown in Table 3. Example 8, Comparative Example 5 740 parts of 1,3-diaminopropane was charged into a reaction vessel, and stirring was started. In a nitrogen stream, 332 parts of isophthalic acid, 365 parts of adipic acid, and 148 parts of 5-sulfonodium dimethyl isophthalate were slowly added at a temperature of 60° C. or lower while being careful not to generate heat.
After the addition was completed, the temperature was started to rise, and it took about 1 hour to slowly raise the temperature to 160°C. Next, a dehydration condensation reaction was carried out at 160° C. for about 3 hours to synthesize a polyamide derivative. The amine value of the obtained polyamide derivative is 400
It was hot. This polyamide derivative was cooled to 120°C, and 3000 parts of water previously heated to 80°C was slowly added to obtain a pale yellow and transparent aqueous solution, and the pH of the aqueous solution was 10.7. Next, 1,6-hexamethylene diisocyanate was added to the resulting aqueous solution of the polyamide derivative while stirring at high speed.
When 756 parts were slowly added, a uniform emulsion of polyamide polyurea resin which gradually became cloudy was obtained. The resulting polyamide polyurea resin emulsion had a nonvolatile content of 41.6%, a pH of 6.8, and a molecular weight of about 16,000 when measured. The resulting polyamide polyurea resin aqueous solution was spray applied to a polyester pen interlining to a resin solid content of 11.2 g/m 2 , and then 50% of aluminum acetate was applied on top.
% aqueous solution in an amount of 10 g/m 2 (wet) and dried at 60° C. for 3 hours to prepare an adhesive interlining. The obtained polyester adhesive interlining with the polyamide polyurea resin adhered to it was pressed using an Aparol press machine at a pressure of 1 Kg/cm 2 and a temperature of 170°C using a polyester dioset fabric as the adhered fabric.
It was crimped for 10 seconds. The peel strength of the obtained adhesive fabric was 1.76 Kg/inch initially, and the peel strength after washing with water and dry cleaning was 1.67 Kg/inch and 1.58, respectively.
It had excellent durability of Kg/inch. The initial adhesive strength without spraying the aluminum acetate aqueous solution was good at 1.71 Kg/inch, but the peel strength after washing with water and dry cleaning was 1.05 Kg/inch and 0.63 Kg/inch, respectively. It was observed that the number of people in Japan was decreasing. The results are shown in Table 3.
Claims (1)
ååäžã«å®è³ªçã«å°ãªããšãïŒåã®è³éŠæ žã«çµå
ããâSO3MåºïŒåºäžïŒã¯æ°ŽçŽ ããããªãŠã åã¯
ã«ãªãŠã ååïŒãæããããªãšã¹ãã«ãããªã¢ã
ããããªãŠã¬ã¿ã³ãæãã¯ããªã¢ããããªå°¿çŽ æš¹
è100éééšã«å¯ŸããŠã(B)åšæåŸè¡šç¬¬ïŒåã³ç¬¬ïŒ
æããéžã°ããéå±ã®é žåç©ãæ°Žé žåç©æãã¯ã
ããã®ææ©æãã¯ç¡æ©å¡©ã0.5ã20éééšå«æã
ããŠãªãããšãç¹åŸŽãšããæ°èŠãªãããã¡ã«ãæ¥
çå€çµæç©ã ïŒ ããªãšã¹ãã«ãããªã¢ãããããªãŠã¬ã¿ã³æ
ãã¯ããªã¢ããããªå°¿çŽ æš¹èããã¹ã«ããããªãŠ
ã ã€ãœãã¿ã«é žãæãã¯ãã®ã«ã«ãã³é žã®äœçŽã¢
ã«ãã«ãšã¹ãã«ãå ±éåããŠåŸããããã®ã§ãã
ããšãç¹åŸŽãšããç¹èš±è«æ±ç¯å²ç¬¬ïŒé èšèŒã®æ°èŠ
ãªãããã¡ã«ãæ¥çå€çµæç©ã[Claims] 1 (A) -SO 3 M group having a number average molecular weight of 4,000 to 30,000 and substantially bonded to at least one aromatic nucleus in the molecule (M in the group is hydrogen, sodium or potassium atom) per 100 parts by weight of polyester, polyamide, polyurethane, or polyamide polyurea resin, (B) 2nd and 3rd part of the periodic table
1. A novel hot melt adhesive composition comprising 0.5 to 20 parts by weight of an oxide, hydroxide, or an organic or inorganic salt thereof of a metal selected from the group consisting of: 2. The novel invention according to claim 1, wherein the polyester, polyamide, polyurethane, or polyamide polyurea resin is obtained by copolymerizing sulfonium isophthalic acid or a lower alkyl ester of its carboxylic acid. hot melt adhesive composition.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP55127199A JPS5753579A (en) | 1980-09-16 | 1980-09-16 | Novel hot melt adhesive composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP55127199A JPS5753579A (en) | 1980-09-16 | 1980-09-16 | Novel hot melt adhesive composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5753579A JPS5753579A (en) | 1982-03-30 |
JPS6312110B2 true JPS6312110B2 (en) | 1988-03-17 |
Family
ID=14954147
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP55127199A Granted JPS5753579A (en) | 1980-09-16 | 1980-09-16 | Novel hot melt adhesive composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5753579A (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6035067A (en) * | 1983-08-08 | 1985-02-22 | Alps Electric Co Ltd | Hot-melt adhesive |
US5883172A (en) * | 1994-03-11 | 1999-03-16 | Henkel Kommanditgesellschaft Auf Aktien | Polyamide hotmelt adhesive |
DE4408277A1 (en) * | 1994-03-11 | 1995-09-14 | Henkel Kgaa | Polyamide hot melt adhesive |
CN105348497B (en) * | 2015-12-07 | 2018-01-02 | äžæµ·å€©æŽççç²æ¥ææè¡ä»œæéå ¬åž | A kind of novel copolymerized ester PUR and preparation method thereof |
-
1980
- 1980-09-16 JP JP55127199A patent/JPS5753579A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5753579A (en) | 1982-03-30 |
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