JP2007525546A - 改良された耐加水分解性を有する反応性ホットメルト接着剤 - Google Patents
改良された耐加水分解性を有する反応性ホットメルト接着剤 Download PDFInfo
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- JP2007525546A JP2007525546A JP2006507371A JP2006507371A JP2007525546A JP 2007525546 A JP2007525546 A JP 2007525546A JP 2006507371 A JP2006507371 A JP 2006507371A JP 2006507371 A JP2006507371 A JP 2006507371A JP 2007525546 A JP2007525546 A JP 2007525546A
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- Prior art keywords
- adhesive
- diol
- alcohol
- hydroxy
- acrylic polymer
- 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.)
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- 239000004831 Hot glue Substances 0.000 title claims abstract description 23
- 230000007062 hydrolysis Effects 0.000 title claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 title claims description 10
- 150000002009 diols Chemical class 0.000 claims abstract description 49
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000000853 adhesive Substances 0.000 claims description 55
- 230000001070 adhesive effect Effects 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 48
- -1 aromatic diols Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 24
- 229920005862 polyol Polymers 0.000 claims description 19
- 150000003077 polyols Chemical class 0.000 claims description 19
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 229920000058 polyacrylate Polymers 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
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- 150000002513 isocyanates Chemical class 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 239000004814 polyurethane Substances 0.000 claims description 12
- 229920002635 polyurethane Polymers 0.000 claims description 12
- XHUBSJRBOQIZNI-UHFFFAOYSA-N (4-Hydroxy-3-methoxyphenyl)ethanol Chemical compound COC1=CC(CCO)=CC=C1O XHUBSJRBOQIZNI-UHFFFAOYSA-N 0.000 claims description 8
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 claims description 8
- APAJFZPFBHMFQR-UHFFFAOYSA-N anthraflavic acid Chemical compound OC1=CC=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1 APAJFZPFBHMFQR-UHFFFAOYSA-N 0.000 claims description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 7
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 5
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- QPKNDHZQPGMLCJ-UHFFFAOYSA-N 1-(3-aminophenyl)ethanol Chemical compound CC(O)C1=CC=CC(N)=C1 QPKNDHZQPGMLCJ-UHFFFAOYSA-N 0.000 claims description 4
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 4
- AMCOCUDBDKVWRZ-UHFFFAOYSA-N 2-(2-hydroxyethoxy)phenol Chemical compound OCCOC1=CC=CC=C1O AMCOCUDBDKVWRZ-UHFFFAOYSA-N 0.000 claims description 4
- KSMBFKMHJGVFQO-UHFFFAOYSA-N 2-[2-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1C(C)(C)O KSMBFKMHJGVFQO-UHFFFAOYSA-N 0.000 claims description 4
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 claims description 4
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 4
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 claims description 4
- QWMOVJWPTZATFS-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazol-4-amine Chemical compound NC1=C(C)ON=C1C1=CC=CC=C1 QWMOVJWPTZATFS-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- RHBLISBUFROBBC-UHFFFAOYSA-N [9-(hydroxymethyl)fluoren-9-yl]methanol Chemical compound C1=CC=C2C(CO)(CO)C3=CC=CC=C3C2=C1 RHBLISBUFROBBC-UHFFFAOYSA-N 0.000 claims description 4
- QTQUJRIHTSIVOF-UHFFFAOYSA-N amino(phenyl)methanol Chemical compound NC(O)C1=CC=CC=C1 QTQUJRIHTSIVOF-UHFFFAOYSA-N 0.000 claims description 4
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 claims description 4
- JMFRWRFFLBVWSI-UHFFFAOYSA-N cis-coniferyl alcohol Natural products COC1=CC(C=CCO)=CC=C1O JMFRWRFFLBVWSI-UHFFFAOYSA-N 0.000 claims description 4
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 claims description 4
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 claims description 4
- 229960000452 diethylstilbestrol Drugs 0.000 claims description 4
- ZBQZBWKNGDEDOA-UHFFFAOYSA-N eosin B Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC([N+]([O-])=O)=C(O)C(Br)=C1OC1=C2C=C([N+]([O-])=O)C(O)=C1Br ZBQZBWKNGDEDOA-UHFFFAOYSA-N 0.000 claims description 4
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 claims description 4
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical compound COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 2
- CDZMWAHBQLPCHD-UHFFFAOYSA-N 3-(4-carboxyphenyl)-1,1,3-trimethyl-2h-indene-5-carboxylic acid Chemical compound C12=CC(C(O)=O)=CC=C2C(C)(C)CC1(C)C1=CC=C(C(O)=O)C=C1 CDZMWAHBQLPCHD-UHFFFAOYSA-N 0.000 claims 3
- GRHCSNBNLAGXFU-UHFFFAOYSA-N 3-phenyl-2-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C1CCCN1CC1NCCCC1C1=CC=CC=C1 GRHCSNBNLAGXFU-UHFFFAOYSA-N 0.000 claims 3
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 claims 3
- 229920001002 functional polymer Polymers 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 10
- 239000012943 hotmelt Substances 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 8
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- 230000002427 irreversible effect Effects 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
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- 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 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 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 4
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- 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
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-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
- HZAWPPRBCALFRN-UHFFFAOYSA-N 1-methyl-4-[(4-methylphenyl)methyl]benzene Chemical compound C1=CC(C)=CC=C1CC1=CC=C(C)C=C1 HZAWPPRBCALFRN-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- WUIXEIPAPIJUGW-UHFFFAOYSA-N 2-[1,1-bis(2-hydroxyphenyl)propyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C=1C(=CC=CC=1)O)(CC)C1=CC=CC=C1O WUIXEIPAPIJUGW-UHFFFAOYSA-N 0.000 description 1
- QPGBFKDHRXJSIK-UHFFFAOYSA-N 2-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=C(C(O)=O)C=CC=C1C(O)=O QPGBFKDHRXJSIK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 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
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
-
- 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
- C08G2250/00—Compositions for preparing crystalline polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/408,141 US8664330B2 (en) | 2003-04-04 | 2003-04-04 | Reactive hot melt adhesive with improved hydrolysis resistance |
| PCT/US2004/008456 WO2004094552A1 (en) | 2003-04-04 | 2004-03-19 | Reactive hot melt adhesive with improved hydrolysis resistance |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011107416A Division JP2011202172A (ja) | 2003-04-04 | 2011-05-12 | 改良された耐加水分解性を有する反応性ホットメルト接着剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007525546A true JP2007525546A (ja) | 2007-09-06 |
| JP2007525546A5 JP2007525546A5 (enExample) | 2011-03-10 |
Family
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Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006507371A Withdrawn JP2007525546A (ja) | 2003-04-04 | 2004-03-19 | 改良された耐加水分解性を有する反応性ホットメルト接着剤 |
| JP2011107416A Pending JP2011202172A (ja) | 2003-04-04 | 2011-05-12 | 改良された耐加水分解性を有する反応性ホットメルト接着剤 |
| JP2015003093A Pending JP2015110788A (ja) | 2003-04-04 | 2015-01-09 | 改良された耐加水分解性を有する反応性ホットメルト接着剤 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011107416A Pending JP2011202172A (ja) | 2003-04-04 | 2011-05-12 | 改良された耐加水分解性を有する反応性ホットメルト接着剤 |
| JP2015003093A Pending JP2015110788A (ja) | 2003-04-04 | 2015-01-09 | 改良された耐加水分解性を有する反応性ホットメルト接着剤 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8664330B2 (enExample) |
| EP (1) | EP1611219A1 (enExample) |
| JP (3) | JP2007525546A (enExample) |
| CN (2) | CN1829784B (enExample) |
| WO (1) | WO2004094552A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011105950A (ja) * | 2011-02-04 | 2011-06-02 | Taiyo Holdings Co Ltd | ウレタン樹脂、それを含有する熱硬化性樹脂組成物及びその硬化物 |
| JP2017214526A (ja) * | 2016-06-02 | 2017-12-07 | Ｄｉｃグラフィックス株式会社 | 接着剤組成物、接着剤、及び包装用積層体 |
| WO2019031231A1 (ja) * | 2017-08-10 | 2019-02-14 | 株式会社クラレ | ポリウレタンホットメルト接着剤、それを用いた積層体及び積層体の製造方法 |
| JP2019537651A (ja) * | 2016-11-10 | 2019-12-26 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ | 反応性ホットメルト接着剤組成物およびその使用 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10149142A1 (de) | 2001-10-05 | 2003-04-24 | Henkel Kgaa | Modifizierter reaktiver Schmelzklebstoff und dessen Verwendung |
| US20060210808A1 (en) * | 2002-10-15 | 2006-09-21 | Ju-Ming Hung | Reactive hot melt adhesive with non-polymeric aliphatic difunctionals |
| US7037402B2 (en) * | 2002-10-15 | 2006-05-02 | National Starch & Chemical Investment Holding Corporation | Reactive hot melt adhesive with non-polymeric aromatic difunctionals |
| US8664330B2 (en) | 2003-04-04 | 2014-03-04 | Henkel US IP LLC | Reactive hot melt adhesive with improved hydrolysis resistance |
| US20070155859A1 (en) * | 2006-01-04 | 2007-07-05 | Zhengzhe Song | Reactive polyurethane hot melt adhesive |
| JP2015101699A (ja) | 2013-11-27 | 2015-06-04 | ヘンケルジャパン株式会社 | 湿気硬化型ホットメルト接着剤 |
| JP6409220B1 (ja) * | 2016-12-22 | 2018-10-24 | Dic株式会社 | 湿気硬化型ウレタンホットメルト樹脂組成物、積層体、及び、靴 |
| CN112646534A (zh) * | 2020-12-24 | 2021-04-13 | 上海回天新材料有限公司 | 一种智能穿戴产品用湿固化聚氨酯热熔胶及其制备方法 |
| CN113969655B (zh) * | 2021-11-15 | 2023-07-28 | 江阴市维沃保温材料有限公司 | 一种单面彩钢无机硅晶防排烟风管板材及其制作方法 |
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| JPH0337278A (ja) * | 1989-06-22 | 1991-02-18 | Xerox Corp | ホットメルトインク組成物 |
| JPH03207782A (ja) * | 1990-01-10 | 1991-09-11 | Mitsubishi Kasei Corp | 反応性ホットメルト接着剤 |
| JPH05311145A (ja) * | 1986-05-05 | 1993-11-22 | Natl Starch & Chem Corp | 溶剤不含のホットメルト−ポリウレタン接着剤組成物 |
| JPH06271830A (ja) * | 1993-03-18 | 1994-09-27 | Sekisui Chem Co Ltd | ホットメルト接着剤 |
| JPH1087704A (ja) * | 1996-08-26 | 1998-04-07 | Xerox Corp | 重合法及びそれによって生成された樹脂粒子 |
| JP2002284838A (ja) * | 2001-03-26 | 2002-10-03 | Nicca Chemical Co Ltd | ヒドロキシル基含有アクリル−ウレタン共重合体水分散物、二液型水性アクリル−ウレタン組成物、並びに、該組成物を含有する塗工剤及び接着剤 |
| JP2004035890A (ja) * | 2002-07-03 | 2004-02-05 | Rohm & Haas Co | グリーン強度を改善した反応性ホットメルト接着剤組成物 |
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| US4585819A (en) | 1984-08-14 | 1986-04-29 | H. B. Fuller Company | Fusion adhesive which can comprise an isocyanate prepolymer, a thermoplastic polymer and/or a lower molecular weight ketone resin |
| US4775719A (en) * | 1986-01-29 | 1988-10-04 | H. B. Fuller Company | Thermally stable hot melt moisture-cure polyurethane adhesive composition |
| JPH0730297B2 (ja) * | 1986-03-25 | 1995-04-05 | 旭硝子株式会社 | ホツトメルト接着剤 |
| CH666899A5 (de) | 1986-05-09 | 1988-08-31 | Sika Ag | Reaktiver schmelzklebstoff. |
| US5036143A (en) | 1987-04-14 | 1991-07-30 | Caschem, Inc. | Urethane adhesive |
| US5166289A (en) | 1990-12-19 | 1992-11-24 | Exxon Chemical Patents Inc. | Thermoset coating composition having improved hardness |
| FR2698877B1 (fr) * | 1992-12-04 | 1995-04-07 | Atochem Elf Sa | Composition adhésives thermofusibles réticulables à l'humidité. |
| DE4242687B8 (de) | 1992-12-17 | 2006-01-12 | Henkel Kgaa | Hydrophile Polyurethane |
| JPH06271832A (ja) | 1993-03-18 | 1994-09-27 | Sekisui Chem Co Ltd | 反応性ホットメルト型接着剤 |
| US5618904A (en) * | 1993-12-29 | 1997-04-08 | Essex Specialty Products Inc. | Polyurethane hot melt adhesive |
| DE4419449A1 (de) | 1994-06-03 | 1995-12-07 | Henkel Kgaa | Schnell abbindender Polyurethan-Schmelzklebstoff |
| PT797604E (pt) * | 1994-05-25 | 2000-05-31 | Henkel Kgaa | Cola de fusao de poliuretano que endurece por accao da humidade |
| DE19742217A1 (de) | 1997-09-24 | 1999-04-01 | Henkel Kgaa | Hydrophiles, hochmolekulares Polyurethan, Klebstoffzusammensetzungen, die dieses enthalten sowie Verwendung dieses Polyurethans |
| WO1999028363A1 (en) | 1997-12-01 | 1999-06-10 | Henkel Kommanditgesellschaft Auf Aktien | Modified polyurethane hotmelt adhesive |
| US6387449B1 (en) | 1999-12-01 | 2002-05-14 | H. B. Fuller Licensing & Financing, Inc. | Reactive hot melt adhesive |
| US6482878B1 (en) | 2000-04-21 | 2002-11-19 | National Starch And Chemical Investment Holding Corporation | Polyurethane hotmelt adhesives with acrylic copolymers and thermoplastic resins |
| US6635722B2 (en) | 2000-05-02 | 2003-10-21 | Henkel Corporation | Moisture-curable polyurethane hot melt adhesives containing reactive amine catalysts |
| US20030022973A1 (en) | 2001-04-13 | 2003-01-30 | Ju-Ming Hung | Moisture cured polyurethane hot melt adhesives with reactive tackifiers |
| US6613836B2 (en) | 2001-06-15 | 2003-09-02 | National Starch And Chemical Investment Holding Corporation | Reactive hot melt adhesive |
| US20040072953A1 (en) | 2002-10-15 | 2004-04-15 | Ju-Ming Hung | Reactive hot melt adhesive with non-polymeric aliphatic difunctionals |
| US7037402B2 (en) | 2002-10-15 | 2006-05-02 | National Starch & Chemical Investment Holding Corporation | Reactive hot melt adhesive with non-polymeric aromatic difunctionals |
| US8664330B2 (en) | 2003-04-04 | 2014-03-04 | Henkel US IP LLC | Reactive hot melt adhesive with improved hydrolysis resistance |
| IL169592A (en) * | 2005-07-07 | 2013-11-28 | Bromine Compounds Ltd | Process for making tetrabromobisphenol a |
-
2003
- 2003-04-04 US US10/408,141 patent/US8664330B2/en not_active Expired - Fee Related
-
2004
- 2004-03-19 CN CN2004800149171A patent/CN1829784B/zh not_active Expired - Fee Related
- 2004-03-19 CN CN201010293076XA patent/CN101935512B/zh not_active Expired - Fee Related
- 2004-03-19 EP EP04759686A patent/EP1611219A1/en not_active Withdrawn
- 2004-03-19 WO PCT/US2004/008456 patent/WO2004094552A1/en not_active Ceased
- 2004-03-19 JP JP2006507371A patent/JP2007525546A/ja not_active Withdrawn
-
2011
- 2011-05-12 JP JP2011107416A patent/JP2011202172A/ja active Pending
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2015
- 2015-01-09 JP JP2015003093A patent/JP2015110788A/ja active Pending
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| JPH05311145A (ja) * | 1986-05-05 | 1993-11-22 | Natl Starch & Chem Corp | 溶剤不含のホットメルト−ポリウレタン接着剤組成物 |
| JPH0337278A (ja) * | 1989-06-22 | 1991-02-18 | Xerox Corp | ホットメルトインク組成物 |
| JPH03207782A (ja) * | 1990-01-10 | 1991-09-11 | Mitsubishi Kasei Corp | 反応性ホットメルト接着剤 |
| JPH06271830A (ja) * | 1993-03-18 | 1994-09-27 | Sekisui Chem Co Ltd | ホットメルト接着剤 |
| JPH1087704A (ja) * | 1996-08-26 | 1998-04-07 | Xerox Corp | 重合法及びそれによって生成された樹脂粒子 |
| JP2002284838A (ja) * | 2001-03-26 | 2002-10-03 | Nicca Chemical Co Ltd | ヒドロキシル基含有アクリル−ウレタン共重合体水分散物、二液型水性アクリル−ウレタン組成物、並びに、該組成物を含有する塗工剤及び接着剤 |
| JP2004035890A (ja) * | 2002-07-03 | 2004-02-05 | Rohm & Haas Co | グリーン強度を改善した反応性ホットメルト接着剤組成物 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011105950A (ja) * | 2011-02-04 | 2011-06-02 | Taiyo Holdings Co Ltd | ウレタン樹脂、それを含有する熱硬化性樹脂組成物及びその硬化物 |
| JP2017214526A (ja) * | 2016-06-02 | 2017-12-07 | Ｄｉｃグラフィックス株式会社 | 接着剤組成物、接着剤、及び包装用積層体 |
| JP2019537651A (ja) * | 2016-11-10 | 2019-12-26 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンＨｅｎｋｅｌ ＡＧ ＆ Ｃｏ． ＫＧａＡ | 反応性ホットメルト接着剤組成物およびその使用 |
| US11530344B2 (en) | 2016-11-10 | 2022-12-20 | Henkel Ag & Co. Kgaa | Reactive hot melt adhesive composition and use thereof |
| WO2019031231A1 (ja) * | 2017-08-10 | 2019-02-14 | 株式会社クラレ | ポリウレタンホットメルト接着剤、それを用いた積層体及び積層体の製造方法 |
| JPWO2019031231A1 (ja) * | 2017-08-10 | 2020-08-27 | 株式会社クラレ | ポリウレタンホットメルト接着剤、それを用いた積層体及び積層体の製造方法 |
| JP7300384B2 (ja) | 2017-08-10 | 2023-06-29 | 株式会社クラレ | ポリウレタンホットメルト接着剤、それを用いた積層体及び積層体の製造方法 |
| US11697750B2 (en) | 2017-08-10 | 2023-07-11 | Kuraray Co., Ltd. | Polyurethane hot-melt adhesive, laminated body using same, and method for producing laminated body |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101935512A (zh) | 2011-01-05 |
| WO2004094552A1 (en) | 2004-11-04 |
| CN1829784A (zh) | 2006-09-06 |
| JP2011202172A (ja) | 2011-10-13 |
| CN101935512B (zh) | 2013-01-02 |
| US8664330B2 (en) | 2014-03-04 |
| US20040198899A1 (en) | 2004-10-07 |
| EP1611219A1 (en) | 2006-01-04 |
| JP2015110788A (ja) | 2015-06-18 |
| CN1829784B (zh) | 2010-12-01 |
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