JP2021038304A - ポリイソシアネート組成物およびその製造方法 - Google Patents
ポリイソシアネート組成物およびその製造方法 Download PDFInfo
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- JP2021038304A JP2021038304A JP2019159871A JP2019159871A JP2021038304A JP 2021038304 A JP2021038304 A JP 2021038304A JP 2019159871 A JP2019159871 A JP 2019159871A JP 2019159871 A JP2019159871 A JP 2019159871A JP 2021038304 A JP2021038304 A JP 2021038304A
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- Japan
- Prior art keywords
- mass
- polyisocyanate composition
- xylylene diisocyanate
- less
- allophanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 135
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 122
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 122
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims abstract description 74
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical class NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 16
- -1 urethane compound Chemical class 0.000 claims description 121
- 229910052797 bismuth Inorganic materials 0.000 claims description 38
- 239000003054 catalyst Substances 0.000 claims description 37
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 17
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 14
- 229920005749 polyurethane resin Polymers 0.000 abstract description 44
- 239000000126 substance Substances 0.000 abstract description 19
- 238000003860 storage Methods 0.000 abstract description 13
- 229920005862 polyol Polymers 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 43
- 150000003077 polyols Chemical class 0.000 description 39
- 239000003795 chemical substances by application Substances 0.000 description 34
- 150000001875 compounds Chemical class 0.000 description 30
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 23
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 22
- 239000010408 film Substances 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 239000001257 hydrogen Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000000853 adhesive Substances 0.000 description 17
- 230000001070 adhesive effect Effects 0.000 description 17
- 239000012948 isocyanate Substances 0.000 description 17
- 150000002513 isocyanates Chemical class 0.000 description 17
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000001298 alcohols Chemical class 0.000 description 14
- 239000002981 blocking agent Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 239000003963 antioxidant agent Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000499 gel Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
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- 239000004814 polyurethane Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 241000894007 species Species 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 229940049920 malate Drugs 0.000 description 4
- 229910052751 metal Chemical class 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 3
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920001214 Polysorbate 60 Polymers 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
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- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
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- 150000002989 phenols Chemical class 0.000 description 3
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 3
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- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
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- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
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- 229910000831 Steel Inorganic materials 0.000 description 2
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- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
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- Polyurethanes Or Polyureas (AREA)
Abstract
Description
4−ジアミノ−5−トルエンスルホン酸、N−(2−アミノエチル)−2−アミノエタンスルホン酸、2−アミノエタンスルホン酸、N−(2−アミノエチル)−2−アミノブタンスルホン酸、または、それらスルホン酸の金属塩類またはアンモニウム塩類などが挙げられる。
ポリイソシアネート組成物のサンプルをゲルパーミエーションクロマトグラフ(GPC)測定し、得られたクロマトグラム(チャート)における各ピークの面積の、全ピークの面積に対する面積率を求めた。
(1)分析装置 : Alliance(Waters)
(2)ポンプ : Alliance 2695(Waters)
(3)検出器 : 2414型示差屈折検出器(Waters)
(4)溶離液 : Tetrahydrofuran
(5)分離カラム :Plgel GUARD + Plgel 5μmMixed−C×3本(50×7.5mm,300×7.5mm)
メーカー ; Polymer Laboratories
品番 ; PL1110−6500
(6)測定温度 : 40℃
(7)流速 : 1mL/min
(8)サンプル注入量 : 100μL
(9)解析装置 : EMPOWERデータ処理装置(Waters)
・システム補正
(1)標準物質名 : Polystyrene
(2)検量線作成方法 : 分子量の異なるTOSOH社製 TSKstandard Polystyreneを用い、リテンションタイムと分子量のグラフを作成。
(3)注入量、注入濃度 : 100μL、 1mg/mL
なお、実施例1のポリイソシアネート組成物のゲルパーミエーションクロマトグラムを図1に示す。
アロファネート化触媒中のビスマスの含有割合(Bi濃度)を、以下の条件で、蛍光X線分析により求めた。
ポリイソシアネート組成物の粘度を、以下の条件で測定した。
ウレタン基/アロファネート基のIR比を、以下の条件で測定した。
撹拌機、温度計、冷却器および窒素ガス導入管を備えた容量1リットルの四つ口フラスコに、窒素雰囲気下、1,3−キシリレンジイソシアネート(三井化学社製、m−XDI(以下、m−XDI−1))100質量部と、イソブタノール(IBA)15.8質量部(当量比NCO/OH=5)と、トリス(2−エチルヘキシル)ホスファイト(酸化防止剤)0.06質量部と、ペンタエリスリトールテトラキス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート](酸化防止剤)0.06質量部とを仕込み、75℃で3.5時間、ウレタン化反応させた。これにより、ウレタン化物を得た。
表1に示す処方および反応条件に変更した以外は、実施例1と同じ方法で、キシリレンジイソシアネートのアロファネート誘導体を含むポリイソシアネート組成物を得た。
1.貯蔵安定性の評価
各ポリイソシアネート組成物を、比較的低温である5℃で24時間保管した。そして、保管後のポリイソシアネート組成物の貯蔵安定性を、目視により確認し、以下の方法で評価した。評価の基準を下記する。
(1)塗料
(1−1)ポリウレタン樹脂の製造
ベースコート層が形成された基材を準備し、そのベースコート層の上に、クリアコート層として、各ポリイソシアネート組成物を用いてポリウレタン層を形成した。
ポリウレタン樹脂の平滑性を、BYK−Gardner社製Wave−scan dualにて、Short wave(Sw)モードおよびLong wave(Lw)モードそれぞれで評価した。その結果を、表1に示す。
ガーゼにメチルエチルケトンを含浸させ、ポリウレタン樹脂の表面を、1000g荷重をかけて往復させた。ポリウレタン樹脂が剥離または破けるまでの往復回数を耐薬品性として評価した。その結果を、表1に示す。
(2−1)ラミネートフィルムの製造
各ポリイソシアネート組成物を、硬化剤として準備した。
ラミネートフィルムの、アルミニウム箔/未延伸ポリプロピレンフィルム間の接着強度を、25℃環境下、試験片幅15mm、引張速度300mm/min、T型剥離試験により測定した。その結果を、表1に示す。
ラミネートフィルムを、135℃で20分間、0.35MPaの加圧下で、8rpmにて回転させながら熱水殺菌した(レトルト試験)。
Claims (5)
- キシリレンジイソシアネートのアロファネート誘導体を含有するポリイソシアネート組成物であり、
ポリイソシアネート組成物の総量に対して、
キシリレンジイソシアネートのアロファネート2分子体の含有割合が50質量%以上72質量%以下であり、
キシリレンジイソシアネートのウレトジオン2分子体の含有割合が12質量%以下である
ことを特徴とする、ポリイソシアネート組成物。 - ポリイソシアネート組成物の総量に対して、
キシリレンジイソシアネートのアロファネート3分子体の含有割合が10質量%以上30質量%以下である
ことを特徴とする、請求項1に記載のポリイソシアネート組成物。 - ポリイソシアネート組成物の総量に対して、
キシリレンジイソシアネートのイソシアヌレート3分子体の含有割合が5質量%以下である
ことを特徴とする、請求項1または2に記載のポリイソシアネート組成物。 - 請求項1〜3のいずれか一項に記載のポリイソシアネート組成物を製造する方法であり、
キシリレンジイソシアネートおよびアルコールをウレタン化反応させ、ウレタン化物を得る工程と、
ビスマスの含有割合が20質量%以上であるビスマス含有触媒の存在下で、ウレタン化物をアロファネート化させる工程と
を備える
ことを特徴とする、ポリイソシアネート組成物の製造方法。 - ビスマス含有触媒が、カルボン酸ビスマスを含む
ことを特徴とする、請求項4に記載のポリイソシアネート組成物の製造方法。
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Citations (4)
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JP2007177171A (ja) * | 2005-12-28 | 2007-07-12 | Mitsui Chemicals Polyurethanes Inc | アロファネート基含有ポリイソシアネートの製造方法、ならびにウレタンプレポリマーおよびポリウレタン樹脂組成物 |
JP2012007183A (ja) * | 2011-09-29 | 2012-01-12 | Mitsui Chemicals Inc | アロファネート基含有ポリイソシアネート、ならびにウレタンプレポリマー、ポリウレタン樹脂組成物およびその用途 |
WO2015079924A1 (ja) * | 2013-11-27 | 2015-06-04 | Dic株式会社 | ガスバリア性接着剤用樹脂組成物、及び接着剤 |
WO2015133496A1 (ja) * | 2014-03-04 | 2015-09-11 | 三井化学株式会社 | ラミネート接着剤、ラミネートフィルムの製造方法、ラミネートフィルムおよびレトルトパウチ材料 |
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JP2007177171A (ja) * | 2005-12-28 | 2007-07-12 | Mitsui Chemicals Polyurethanes Inc | アロファネート基含有ポリイソシアネートの製造方法、ならびにウレタンプレポリマーおよびポリウレタン樹脂組成物 |
JP2012007183A (ja) * | 2011-09-29 | 2012-01-12 | Mitsui Chemicals Inc | アロファネート基含有ポリイソシアネート、ならびにウレタンプレポリマー、ポリウレタン樹脂組成物およびその用途 |
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