JP2021534312A - 一成分ホットメルトポリウレタン接着剤 - Google Patents
一成分ホットメルトポリウレタン接着剤 Download PDFInfo
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- JP2021534312A JP2021534312A JP2021510043A JP2021510043A JP2021534312A JP 2021534312 A JP2021534312 A JP 2021534312A JP 2021510043 A JP2021510043 A JP 2021510043A JP 2021510043 A JP2021510043 A JP 2021510043A JP 2021534312 A JP2021534312 A JP 2021534312A
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- Japan
- Prior art keywords
- weight
- component
- mixture
- polyurethane adhesive
- polyols
- Prior art date
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- 239000000853 adhesive Substances 0.000 title claims abstract description 85
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 85
- 239000004814 polyurethane Substances 0.000 title claims abstract description 21
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 21
- 239000012943 hotmelt Substances 0.000 title claims description 13
- 229920005862 polyol Polymers 0.000 claims abstract description 51
- 150000003077 polyols Chemical class 0.000 claims abstract description 47
- 229920000728 polyester Polymers 0.000 claims abstract description 36
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 21
- 238000002844 melting Methods 0.000 claims description 20
- 230000008018 melting Effects 0.000 claims description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000013078 crystal Substances 0.000 claims description 15
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 5
- 238000005304 joining Methods 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 2
- 238000010586 diagram Methods 0.000 abstract 1
- -1 poly (alkylene adipate Chemical compound 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 238000001723 curing Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000945 filler Substances 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 239000000454 talc Substances 0.000 description 7
- 229910052623 talc Inorganic materials 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 125000000160 oxazolidinyl group Chemical group 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 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 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
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- 239000004970 Chain extender Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
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- 125000005647 linker group Chemical group 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical group C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000013008 moisture curing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 description 2
- 150000002917 oxazolidines Chemical class 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 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
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000012462 polypropylene substrate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
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- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
A):
1)ポリオールの混合物であって、
i)ポリオールの混合物の重量に基づいて、22℃で液体である少なくとも1つのヒドロキシル末端ポリエステル少なくとも35重量パーセントと;
ii)ポリオールの混合物の重量に基づいて、22℃で固体であり且つ70〜130℃の結晶融解温度を示す少なくとも1つのヒドロキシル末端ポリエステル少なくとも10重量パーセントと;
iii)ポリオールの混合物の重量に基づいて、ヒドロキノンビス−(2−ヒドロキシエチル)エーテル5〜20重量パーセントを含むポリオールの混合物と、
2)少なくとも1つの有機ポリイソシアネートの過剰量との反応生成物である、遊離イソシアネート基含有ポリウレタンプレポリマーの接着剤組成物50〜98重量%と、
B)2000までの分子量を有する少なくとも1つのポリオキサゾリジン化合物1〜10重量%と、
C)水とイソシアネート基との反応のための触媒の触媒有効量とを含む、熱軟化性室温固体である一成分湿気硬化性ホットメルトポリウレタン接着剤組成物である。
HQEEは、約100のヒドロキシル当量を有するヒドロキノンビス(2−ヒドロキシエチル)エーテルである。
結晶性ポリエステルAは、85℃の結晶融解温度、約30.5のヒドロキシル価(当量約1840)及び約3500の数平均分子量を有する飽和ポリエステルである。
結晶性ポリエステルBは、53℃の結晶融解温度、約50.5のヒドロキシル価(当量約1110)及び約2000の数平均分子量を有する飽和ポリエステルである。
液体ポリエステルは、ブチレン対ネオペンチル単位のモル比が約55:45である1000当量の公称で二官能性ポリ(ブチレン/ネオペンチル)アジペートである。この材料は22℃で液体である。
架橋剤は、約88のヒドロキシル当量を有する公称で三官能性プロポキシ化グリセリンである。
液体MDIは、約2.2のイソシアネート官能価及び約143の当量を有する変性ジフェニルメタンジイソシアネート製品である。
タルク充填NCOポリウレタンプレポリマーは、表1に示される調合物から製造される。
Claims (11)
- :
A):
1)ポリオールの混合物であって、
i)ポリオールの前記混合物の重量に基づいて、22℃で液体である少なくとも1つのヒドロキシル末端ポリエステル少なくとも35重量パーセントと;
ii)ポリオールの前記混合物の重量に基づいて、22℃で固体であり且つ70〜130℃の結晶融解温度を示す少なくとも1つのヒドロキシル末端ポリエステル少なくとも10重量パーセントと;
iii)ポリオールの前記混合物の重量に基づいて、ヒドロキノンビス−(2−ヒドロキシエチル)エーテル5〜20重量パーセントを含むポリオールの混合物と、
2)少なくとも1つの有機ポリイソシアネートの過剰量
との反応生成物である、遊離イソシアネート基含有ポリウレタンプレポリマー50〜98重量%と、
B)2000までの分子量を有する少なくとも1つのポリオキサゾリジン化合物1〜10重量%と、
C)水とイソシアネート基との反応のための触媒の触媒有効量とを含む、熱軟化性室温固体である一成分湿気硬化性ホットメルトポリウレタン接着剤組成物。 - 成分ii)が75〜100℃の結晶融解温度を有する、請求項1に記載の一成分湿気硬化性ホットメルトポリウレタン接着剤組成物。
- 成分ii)が700〜2500のヒドロキシル当量及び1.8〜3のヒドロキシル官能価を有する、請求項1又は2に記載の一成分湿気硬化性ホットメルトポリウレタン接着剤組成物。
- 成分i)が700〜1500のヒドロキシル当量及び1.8〜3のヒドロキシル官能価を有する、請求項1〜3のいずれか一項に記載の一成分湿気硬化性ホットメルトポリウレタン接着剤組成物。
- ポリオールの前記混合物が、ポリオールの前記混合物の重量に基づいて成分ii)を12〜25重量%含有する、請求項1〜6のいずれか一項に記載の一成分湿気硬化性ホットメルトポリウレタン接着剤組成物。
- 請求項1〜7のいずれか一項に記載の一成分ポリウレタン接着剤組成物を硬化することによって形成される硬化した接着剤。
- 請求項1〜7のいずれか一項に記載の一成分ポリウレタン接着剤組成物をH2Oと接触させることによって形成される硬化した接着剤。
- 2つの基材の間の接合ラインに請求項1〜7のいずれか一項に記載の一成分ポリウレタン接着剤の層を形成する工程と、前記接合ラインで前記層を硬化して前記基材のそれぞれに接合された硬化した接着剤を形成する工程とを含む、2つの基材を接合する方法。
- 2つの基材の間の接合ラインに請求項1〜7のいずれか一項に記載の一成分ポリウレタン接着剤の層を形成する工程と、前記層をH2Oと接触させることによって前記接合ラインで前記層を硬化して、前記基材のそれぞれに接合された硬化した接着剤を形成する工程とを含む、2つの基材を接合する方法。
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