JPS63139909A - Thermoplastic polyurethane resin composition - Google Patents
Thermoplastic polyurethane resin compositionInfo
- Publication number
- JPS63139909A JPS63139909A JP61287261A JP28726186A JPS63139909A JP S63139909 A JPS63139909 A JP S63139909A JP 61287261 A JP61287261 A JP 61287261A JP 28726186 A JP28726186 A JP 28726186A JP S63139909 A JPS63139909 A JP S63139909A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane resin
- diol
- alicyclic
- resin composition
- aliphatic
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 15
- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims abstract description 14
- 150000002009 diols Chemical class 0.000 claims abstract description 27
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 25
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 19
- -1 alicyclic diol Chemical class 0.000 claims abstract description 13
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 12
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 7
- 229920003232 aliphatic polyester Polymers 0.000 claims abstract description 5
- 150000002596 lactones Chemical class 0.000 claims abstract description 5
- 239000004970 Chain extender Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 abstract description 12
- 238000005299 abrasion Methods 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 230000003746 surface roughness Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003490 calendering Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000009499 grossing Methods 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 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
- 239000008096 xylene Substances 0.000 description 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-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
- 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
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- WUKSXHQRYABKFE-UHFFFAOYSA-N 2-[3-(2-hydroxyethyl)cyclobutyl]ethanol Chemical compound OCCC1CC(CCO)C1 WUKSXHQRYABKFE-UHFFFAOYSA-N 0.000 description 1
- GCOAFEXBTHVORO-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)cycloheptyl]ethanol Chemical compound OCCC1CCCC(CCO)CC1 GCOAFEXBTHVORO-UHFFFAOYSA-N 0.000 description 1
- JVGDVPVEKJSWIO-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCC(CCO)CC1 JVGDVPVEKJSWIO-UHFFFAOYSA-N 0.000 description 1
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
- NILOCPBMTIJETB-UHFFFAOYSA-N 3-[4-(3-hydroxypropyl)cyclohexyl]propan-1-ol Chemical compound OCCCC1CCC(CCCO)CC1 NILOCPBMTIJETB-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- AYVGBNGTBQLJBG-UHFFFAOYSA-N [3-(hydroxymethyl)cyclopentyl]methanol Chemical compound OCC1CCC(CO)C1 AYVGBNGTBQLJBG-UHFFFAOYSA-N 0.000 description 1
- MQEJZVCGHIZWAB-UHFFFAOYSA-N [4-(hydroxymethoxy)cyclohexyl]oxymethanol Chemical compound OCOC1CCC(OCO)CC1 MQEJZVCGHIZWAB-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- VGASFSFONALGLS-UHFFFAOYSA-N ethene;terephthalic acid Chemical compound C=C.C=C.OC(=O)C1=CC=C(C(O)=O)C=C1 VGASFSFONALGLS-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- JTHNLKXLWOXOQK-UHFFFAOYSA-N n-propyl vinyl ketone Natural products CCCC(=O)C=C JTHNLKXLWOXOQK-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920006230 thermoplastic polyester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、耐摩耗性、溶液安定性、伸度及び耐久性に優
れた熱可塑性ポリウレタン樹脂組成物に関し、特に磁気
記録媒体の結合剤として有用な熱可塑性？リウレタン樹
脂組成物に関する。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a thermoplastic polyurethane resin composition having excellent abrasion resistance, solution stability, elongation, and durability, and particularly as a binder for magnetic recording media. Useful thermoplastic? The present invention relates to a urethane resin composition.
（従来技術及びその問題点）
熱可塑性ポリウレタン樹脂は、その優れた性能によシ各
分野で用いられている。例えば特公昭５８−８０５３号
公報には、脂環族ポリエステルジオール、連鎖延長剤、
脂肪族または芳香族ジイソシアネートからなる熱可塑性
Ｉリウレタン樹脂組成物を結合剤として用いた磁気テー
プについて記載されている。しかし々から、脂肪族酸成
分と脂環族ジオール取分とから得られる脂環族４リエス
テルジオールを用いる為に伸びが悪く屈曲性に劣シ％溶
液とした時の低温保存安定性に劣るという問題点があっ
た。(Prior art and its problems) Thermoplastic polyurethane resins are used in various fields due to their excellent performance. For example, Japanese Patent Publication No. 58-8053 discloses an alicyclic polyester diol, a chain extender,
Magnetic tapes are described using thermoplastic I-urethane resin compositions consisting of aliphatic or aromatic diisocyanates as binders. However, it is said that because the alicyclic 4-lyester diol obtained from the aliphatic acid component and the alicyclic diol fraction is used, it has poor elongation, poor flexibility, and poor low-temperature storage stability when made into a % solution. There was a problem.
（問題を解決する為の手段）
そこで本発明者らは、これらの問題点について鋭意研究
した結果、本発明を完成するに至った。(Means for Solving the Problems) The inventors of the present invention have conducted extensive research on these problems, and as a result, have completed the present invention.
即ち、本音発明は、
囚 脂肪族酸成分と脂肪族ジオール成分とから得られる
か、該ジオール成分とラクトンとから得られる脂肪族ポ
リエステルジオール、
（Ｂ） 脂環族ジオールからなる鎖伸長剤、（Ｃ）
有機ジイソシアネートからなシ、かつ得られるポリウ
レタン樹脂中の脂環族環の含有量が、２〜１５重量％、
かつ有機ジイソシアネートの含Ｔ１量が、ｌＯ〜５５重
量係であり、樹脂の分子量が３０，０００〜２００，０
００であることを特徴とする熱可塑性ポリウレタン樹脂
組成物を提供するものである。That is, the present invention provides: (B) an aliphatic polyester diol obtained from an aliphatic acid component and an aliphatic diol component or obtained from the diol component and a lactone; (B) a chain extender comprising an alicyclic diol; C)
is not made of an organic diisocyanate, and the content of alicyclic rings in the obtained polyurethane resin is 2 to 15% by weight,
and the T1 content of the organic diisocyanate is 1O~55% by weight, and the molecular weight of the resin is 30,000~200.0
The present invention provides a thermoplastic polyurethane resin composition characterized in that
本発明の脂肪族ポリエステルジオール（４）は、脂肪族
酸成分と脂肪族ジオール取分との縮合反応により得られ
るか、脂肪族ジオール成分とラクトンとの開環重合反応
により得られるもので、好ましくは分子量２０００以下
、よシ好ましくは１０００以下のものである。The aliphatic polyester diol (4) of the present invention is preferably obtained by a condensation reaction between an aliphatic acid component and an aliphatic diol fraction, or by a ring-opening polymerization reaction between an aliphatic diol component and a lactone. has a molecular weight of 2,000 or less, preferably 1,000 or less.
本発明に使用される脂肪族ジオール成分は、例エバエチ
レングリコール、ジエチレンクリコール。Aliphatic diol components used in the present invention include evaporated ethylene glycol and diethylene glycol.
プロピレングリコール、ジプロピレングリコール。Propylene glycol, dipropylene glycol.
ブチレンクリコール、ペンチルグリコール、ヘキサング
リコールなどの単独又は２以上の混合物であり、脂肪族
酸成分としては１例えばコハク酸。Butylene glycol, pentyl glycol, hexane glycol, etc. alone or as a mixture of two or more, and the aliphatic acid component is one such as succinic acid.
メチルコハク酸、アジピン酸、グルタル酸、アゼライン
酸などの二塩基酸の単独又は２以上の混合物であシ、こ
れらをジオール過剰系で触媒の存在下又は不存在下で通
常の脱水縮合反応することによりてポリエステルジオー
ル（ロ）を得る。また、ポリエステルジオールに）とし
ては、上記脂肪族ジオールを開始剤としてカブロラクト
ン等のラクトン類を開環重合したものの他に、ヘキサン
グリコールとジフェニルカーがネートを脱フエノール反
応によりて得られる炭酸エステルジオールなども使用で
きる。本発明のポリエステルジオールに）中には、芳香
族環や脂環族環を含んではならない。ポリエステルジオ
ール囚中に芳香族環や脂環族環が導入されると、このポ
リエステルジオールから得られるポリウレタン樹脂中の
ソフトセグメントに剛性が生じる為に成形性が低下し、
例えばこのポリウレタン樹脂を結合剤とする磁気記録媒
体の表面を平滑にする為のカレンダー適性が低下する欠
点がある。本発明のポリエステルジオール（ロ）の分子
量は、２０００以下であることが好ましい。ポリエステ
ルジオール（４）の分子量が２０００を越えると鎖伸長
剤の使用量が増えハードセグメントが増加する為、チリ
ウレタン樹脂の伸び、屈曲性、溶解性を低下させる。特
に磁気記録媒体の結合剤として使用する場合、通常溶解
するのに使用される有機溶剤に対する溶解性が低下する
ので好ましくない。Dibasic acids such as methylsuccinic acid, adipic acid, glutaric acid, and azelaic acid may be used alone or in a mixture of two or more, and these can be subjected to a conventional dehydration condensation reaction in a diol-excess system in the presence or absence of a catalyst. to obtain polyester diol (b). Examples of polyester diols include those obtained by ring-opening polymerization of lactones such as cabrolactone using the above aliphatic diol as an initiator, and carbonate diols obtained by dephenolization of hexane glycol and diphenyl carnate. can also be used. The polyester diol of the present invention) must not contain aromatic rings or alicyclic rings. When an aromatic ring or alicyclic ring is introduced into the polyester diol, the soft segment in the polyurethane resin obtained from the polyester diol becomes rigid, resulting in a decrease in moldability.
For example, there is a drawback that calendering suitability for smoothing the surface of a magnetic recording medium using this polyurethane resin as a binder is reduced. The molecular weight of the polyester diol (b) of the present invention is preferably 2,000 or less. When the molecular weight of the polyester diol (4) exceeds 2000, the amount of chain extender used increases and the number of hard segments increases, which reduces the elongation, flexibility, and solubility of the chiliurethane resin. Particularly when used as a binder for magnetic recording media, it is undesirable because the solubility in organic solvents normally used for dissolution is reduced.
本発明に使用される脂環族ジオールからなる鎖伸長剤（
Ｂ）は、例えば１．２−ビス（ヒドロキシエチル）シク
ログロノ譬ン、１．３−ビス（ヒドロキシエチル）シク
ロブタン、１，３−ビス（ヒドロキシメチル）シクロペ
ンタン、１，４−ビス（ヒドロキシメチル）シクロヘキ
サン、１，４−ビス（ヒドロキシエチル）シクロヘキサ
ン、１．４−ビス（ヒドロキシプロピル）シクロヘキサ
ン、１，４−ビス（ヒドロキシエチル）シクロヘプタン
、１，４−ビス（ヒドロキシメトキシ）シクロヘキサン
、１．４−ビス（ヒドロキシエトキシ）シクロヘキサン
。Chain extender consisting of alicyclic diol used in the present invention (
B) is, for example, 1,2-bis(hydroxyethyl)cycloglobin, 1,3-bis(hydroxyethyl)cyclobutane, 1,3-bis(hydroxymethyl)cyclopentane, 1,4-bis(hydroxymethyl) Cyclohexane, 1,4-bis(hydroxyethyl)cyclohexane, 1,4-bis(hydroxypropyl)cyclohexane, 1,4-bis(hydroxyethyl)cycloheptane, 1,4-bis(hydroxymethoxy)cyclohexane, 1.4 -bis(hydroxyethoxy)cyclohexane.
２．２−ビス（４′−ヒドロキシメトキシシクロヘキシ
ル）グロパン、２．２−ビス（４′−ヒドロキシエトキ
シシクロヘキシル）グロパンなどが挙ケラレる。これら
の脂環族ジオールに、エチレングリコール、ジエチレン
グリコール、プロピレングリコール、ジグロビレングリ
コール、ブチレングリコール、ペンチルグリコール、ヘ
キサングリコールなどの脂肪族ジオールを混合使用する
こともできる。本発明のポリウレタン樹脂組成物は、鎖
伸長剤として使用される脂環族ジオール（Ｂ）から導入
される脂環族環を２〜１５重ｉ−憾含有し々ければなら
ない。ポリウレタン樹脂中に脂環族環が２重量憾より少
ない場合はそのポリウレタン樹脂の耐久性が劣り、一方
１５重量係より多い場合はポリウレタン樹脂の有機溶剤
に対する溶解性が低下すると共にそのポリウレタン樹脂
を例えば結合剤とする磁気記録媒体の表面を平滑にする
為のカレンダー適性が低下する欠点がある。Examples include 2.2-bis(4'-hydroxymethoxycyclohexyl)glopane and 2.2-bis(4'-hydroxyethoxycyclohexyl)glopane. These alicyclic diols may be mixed with aliphatic diols such as ethylene glycol, diethylene glycol, propylene glycol, diglobylene glycol, butylene glycol, pentyl glycol, and hexane glycol. The polyurethane resin composition of the present invention must contain 2 to 15 alicyclic rings introduced from the alicyclic diol (B) used as a chain extender. If the number of alicyclic rings in the polyurethane resin is less than 2% by weight, the durability of the polyurethane resin will be poor, while if it is more than 15% by weight, the solubility of the polyurethane resin in organic solvents will decrease and the polyurethane resin may be There is a drawback that calendering suitability for smoothing the surface of a magnetic recording medium used as a binder is reduced.
本発明の有機ジイソシアネー） （Ｃ）としては、例え
ばヘキサメチレンジイソシアネート、リジンジイソシア
ネート、インホロンジインシアネート、キシレンジイソ
シアネート、シクロヘキサンジイソシアネート、トルイ
ジンジイソシアネート。Examples of the organic diisocyanate (C) of the present invention include hexamethylene diisocyanate, lysine diisocyanate, inphorone diisocyanate, xylene diisocyanate, cyclohexane diisocyanate, and toluidine diisocyanate.
２．４− ）リレンジイソシアネート（２，４−ＴＤＩ
）。2.4- ) lylene diisocyanate (2,4-TDI
).
２．６− ）リレンジイソシアネー） （２，６−ＴＤ
Ｉ ）、４．４′−ジフェニルメタンジイソシアネート
（ＭＤＩ）。2.6- ) lylene diisocyanate) (2,6-TD
I), 4,4'-diphenylmethane diisocyanate (MDI).
ｐ−フェニレンジイソシアネート、ｍ−フェニレンジイ
ソシアネート、１．５−ナフチレンジイソシアネート等
が挙げられるが、主に独！、２．４−ＴＤＩ。Examples include p-phenylene diisocyanate, m-phenylene diisocyanate, 1,5-naphthylene diisocyanate, etc., but mainly German! , 2.4-TDI.
２．６− ＴＤＩが使用される。2.6- TDI is used.
又有機ジイソシアネート（ロ）はポリウレタン樹脂構成
比率は１０〜５５重量係好ましくは２０〜４５重量係で
なければならない。１０重重量上シ少ない場合は、磁性
層が充分な耐摩耗性と耐久性を得られず、一方５５重量
憾を越えると通常磁気記録媒体の結合剤を溶解するのに
使用される様な有機溶剤に対する溶解性が低下する欠点
と共に、カレンダー適性が低下する欠点がある。The organic diisocyanate (b) should have a polyurethane resin composition ratio of 10 to 55% by weight, preferably 20 to 45% by weight. If the weight is less than 10% by weight, the magnetic layer will not have sufficient abrasion resistance and durability, while if it exceeds 55% by weight, organic compounds such as those commonly used to dissolve binders in magnetic recording media will not be able to obtain sufficient wear resistance and durability. In addition to the drawback of reduced solubility in solvents, there is also the drawback of reduced calenderability.
本発明のポリウレタン樹脂組成物は、通常の方法により
製造される。即ち無溶剤系でポリエステルジオール（４
）及び鎖伸長剤（Ｂ）を有機ジイソシアネ−） （Ｃ）
を反応させるか或は有機溶剤の一部又は全部の存在下で
ポリエステルジオール囚及び鎖伸長剤（Ｂ）を有機ジイ
ソシアネートＣ）を反応させて得られる。また、ポリエ
ステルジオール囚をあらかじめ有機ジイソシアネート（
Ｑと反応させ末端イソシアネート基の！レポリマーを作
り、これに鎖伸長剤（Ｂ）を反応させてもよい。ウレタ
ン化反応の際にウレタン化反応を促進する触媒を使用す
ることもできる。The polyurethane resin composition of the present invention is produced by a conventional method. That is, polyester diol (4
) and chain extender (B) as an organic diisocyanate) (C)
or by reacting a polyester diol and a chain extender (B) with an organic diisocyanate C) in the presence of part or all of an organic solvent. In addition, the polyester diol can be treated with organic diisocyanate (
React with Q to form terminal isocyanate groups! A repolymer may be prepared and reacted with the chain extender (B). A catalyst that promotes the urethanization reaction can also be used during the urethanization reaction.
本発明の４リウレタン樹脂の分子量は、テトラヒドロフ
ランを溶媒とするｒルパーメーシ、ンクロマトグラフィ
ーによるポリスチレン換算重量平均分子量が３０，００
０〜２００，０００でなければならない。分子量が３０
，０００よシ小さい場合は耐摩耗性及び耐久性が劣る欠
点があシ分子量が２００．０００よシ大きい場合は、磁
気記録媒体等を分散した結合剤溶液の粘度が高＜ｔｂす
ぎ支持体への塗工が困難になるか或は塗工しやすい粘度
まで希釈するに要する溶媒の使用量が多くなシすぎ塗工
後の乾燥に長時間を要する欠点が生じる。The molecular weight of the 4-urethane resin of the present invention is determined by polystyrene-equivalent weight average molecular weight of 30,000 by chromatography using tetrahydrofuran as a solvent.
Must be between 0 and 200,000. Molecular weight is 30
If the molecular weight is smaller than 200,000, the disadvantage is poor wear resistance and durability.If the molecular weight is larger than 200,000, the viscosity of the binder solution in which the magnetic recording medium etc. is dispersed is too high. The disadvantage is that it becomes difficult to apply the coating, or that a large amount of solvent is required to dilute the coating to a viscosity that is easy to coat.
不発ルの４リウレタン樹脂組成物は有機溶剤に溶解して
使用される。通常使用される有機溶剤としては、シクロ
ヘキサノン、メチルエチルケトン。The unexploded 4-urethane resin composition is used after being dissolved in an organic solvent. Commonly used organic solvents include cyclohexanone and methyl ethyl ketone.
メチルイソブチルケトン、酢酸メチル、酢酸エチル、酢
酸ブチル、トルエン、キシレン等の単独或は混合溶剤が
挙げられる。Examples include single or mixed solvents such as methyl isobutyl ketone, methyl acetate, ethyl acetate, butyl acetate, toluene, and xylene.
本発明の４ｔｙウレタン樹脂組成物はそれ自体優れた耐
摩耗性と耐久性を与えるが更に優れた耐摩耗性、耐久性
及び支持体に対する密着性を与える為に低分子量ポリイ
ソシアネートが配合使用される。低分子量？ジイソシア
ネートとしては例えばトリレンジイソシアネート、ヘキ
サメチレンジイソシアネートなどのジイソシアネート３
モルとトリメチロールグロノ９ン、グリセリンなどのト
リオール１モルとの反応生成物などが挙げられる。本発
明のポリウレタン樹脂組成物に必要ならば通常用いられ
ている熱可塑性ポリウレタン樹脂、塩化ビニル樹脂、塩
化ビニル−酢酸ビニル系共重合体。The 4ty urethane resin composition of the present invention itself provides excellent abrasion resistance and durability, but in order to provide even more excellent abrasion resistance, durability, and adhesion to the support, a low molecular weight polyisocyanate is blended and used. . Low molecular weight? Examples of diisocyanates include diisocyanates such as tolylene diisocyanate and hexamethylene diisocyanate.
Examples include a reaction product of 1 mole of a triol such as trimethylolgulon, glycerin, etc. Thermoplastic polyurethane resins, vinyl chloride resins, and vinyl chloride-vinyl acetate copolymers are commonly used if necessary in the polyurethane resin composition of the present invention.
塩化ピニルーグロピオン酸ビニル系共重合体、繊維素繊
維系樹脂％／ ＩＪビニルブチラール樹脂、熱可塑性ポ
リエステル樹脂、エポキシ樹脂、フェノキシ樹脂等を併
用することができる。A pinyl chloride-vinyl gropionate copolymer, cellulose fiber resin %/IJ vinyl butyral resin, thermoplastic polyester resin, epoxy resin, phenoxy resin, etc. can be used in combination.
（効果）
こうして得られる本発明の樹脂組成物は、耐久性、耐摩
耗性、伸び、屈曲性、溶液での低温保存安定性に優れて
いる為、塗料、成形材料、接着剤、床材、ブライマー、
フオーム等積々の分野で利用できるが、特に磁気記録媒
体の結合剤として有用である。(Effects) The resin composition of the present invention thus obtained has excellent durability, abrasion resistance, elongation, flexibility, and low-temperature storage stability in solution, so it can be used in paints, molding materials, adhesives, flooring materials, etc. Brymer,
Although it can be used in many fields such as foam, it is particularly useful as a binder for magnetic recording media.
（実施例）
以下に実施例を挙げて本発明を更に具体的に説明するが
、本発明はこれらの実施例に限定されるものではない。(Examples) The present invention will be described in more detail with reference to Examples below, but the present invention is not limited to these Examples.
尚、実施例中において「部」は「重量部」を示す。In the examples, "parts" indicate "parts by weight."
実施例１〜４．比較例１〜４
コンデンサー、温度計及び攪拌装置が展層された５１ス
テンレススチ一ル製反応容器にポリエステルジオールに
）鎖伸長剤（Ｂ）を仕込み８０℃に加温し、ポリエステ
ルジオール（４）、鎖伸長剤（Ｂ）及ヒ有機ジイソシア
ネートの合計の１．５倍重量のシクロ錫ジラウレートを
加え均一にした後有機ジイソシアネート（Ｃ）を加え、
９０℃にて反応し、ポリウレタン樹脂の分子量が目標に
達し走時、未反応のインシアネート基と等モル量のメタ
ノールとシクロヘキサノンと同重量のメチルエチルケト
ンを加え、ウレタン樹脂濃度が２５重量憾の溶液を得た
。Examples 1-4. Comparative Examples 1 to 4 A chain extender (B) (to polyester diol) was charged into a reaction vessel made of 51 stainless steel equipped with a condenser, a thermometer, and a stirring device, heated to 80°C, and polyester diol (4) was added. , cyclotin dilaurate in an amount of 1.5 times the total weight of the chain extender (B) and the organic diisocyanate was added to make the mixture uniform, and then the organic diisocyanate (C) was added.
When the reaction was carried out at 90°C and the molecular weight of the polyurethane resin reached the target, methanol in an equimolar amount to the unreacted incyanate group, methyl ethyl ketone in an equal molar amount to cyclohexanone, and a solution having a urethane resin concentration of 25% by weight were added. Obtained.
ポリウレタン樹脂の分子量はｒ／Ｌ／パーメーシ。The molecular weight of the polyurethane resin is r/L/Permesy.
ンクロマトグラフによシ、／リスチレン分子量換算の重
量平均分子量で求められた。It was determined by weight average molecular weight in terms of the molecular weight of styrene by chromatography.
実施例１〜４及び比較例１〜４のポリエステルジオール
（４）の種類、鎖伸長剤（Ｂ）の種類及び得られ次ポリ
ウレタン樹脂組成、物性などを表−１に示した。Table 1 shows the type of polyester diol (4), type of chain extender (B), composition of the resulting polyurethane resin, physical properties, etc. of Examples 1 to 4 and Comparative Examples 1 to 4.
比較例１及び２は、脂環族環の含有量の多いポリウレタ
ン樹脂である為に伸度、溶液安定性の点で劣ったもので
あった。Comparative Examples 1 and 2 were inferior in terms of elongation and solution stability because they were polyurethane resins with a high content of alicyclic rings.
比較例３は、ポリウレタン樹脂の分子量が低い為に耐摩
耗性の点で劣ったものであった。Comparative Example 3 had poor abrasion resistance due to the low molecular weight of the polyurethane resin.
比較例４は、実施例１に使用した鎖伸長剤１．４−ビス
（ヒドロキシメチル）シクロヘキサンを脂環族環を有ざ
力い１，４−ブチレングリコールに代えたポリウレタン
樹脂である。このポリウレタン樹脂は樹脂製［２５パー
セントでシクロヘキサノンとメチルエチルケトンとの混
合溶剤に溶解し難く、良好な流動性のある溶液として得
られなかった。Comparative Example 4 is a polyurethane resin in which the chain extender 1,4-bis(hydroxymethyl)cyclohexane used in Example 1 was replaced with 1,4-butylene glycol, which has an alicyclic ring. This polyurethane resin was made of resin [25% and was difficult to dissolve in a mixed solvent of cyclohexanone and methyl ethyl ketone, and a solution with good fluidity could not be obtained.
応用例１〜４、比較応用例１〜４
実施例１〜４または比較例１〜４により得られた
ポリウレタン樹脂溶液（２５％） １８０部シク
ロヘキサノン ３００部メチルエチルケ
トン ７８０部γ−Ｆ６２０５磁性粉末
３５０部カーＭンブラック
１２部潤 滑 剤
５部上記混合物を？−ルミル中で２４時間
練肉した後、バーノックＤ−７５０（大日本インキ化学
工業社製。Application Examples 1 to 4, Comparative Application Examples 1 to 4 Polyurethane resin solution (25%) obtained in Examples 1 to 4 or Comparative Examples 1 to 4 180 parts Cyclohexanone 300 parts Methyl ethyl ketone 780 parts γ-F6205 magnetic powder
350 copies car Mn black
12 parts lubricant
5 parts of the above mixture? - After kneading in Lumil for 24 hours, Burnock D-750 (manufactured by Dainippon Ink and Chemicals) was used.
低分子量ポリイソシアネート）を２０部添加し、さらに
一時間練肉し厚さ１０ミクロンの？ジエチレンテレフタ
レート基体フィルム上に乾燥後の厚みが１６ミクロンと
なるように塗布乾燥し、所定の幅に截断して磁気記録チ
ー７’４１〜８を作った。Add 20 parts of low molecular weight polyisocyanate) and knead for another hour until the thickness is 10 microns. It was coated and dried on a diethylene terephthalate base film to a thickness of 16 microns after drying, and cut to a predetermined width to form magnetic recording chips 7'41-8.
く磁気テープの光沢試験〉
得られた各磁気テープの磁性面をデジタル変角光度計を
用い入射角４５度、反射角４５度で測定した。Gloss Test of Magnetic Tape> The magnetic surface of each magnetic tape obtained was measured using a digital variable angle photometer at an incident angle of 45 degrees and a reflection angle of 45 degrees.
く磁気テープの表面荒さ試験〉
得られ九各磁気テープの磁性面を表面粗度計を用い測定
し中心線平均粗さで表わした。Surface Roughness Test of Magnetic Tape The magnetic surface of each of the nine magnetic tapes obtained was measured using a surface roughness meter and expressed as center line average roughness.
く磁気テープの耐摩耗性試験〉
得られた磁気テープの磁性面をテーパ一式摩耗試験機を
用いて磁性層が脱落するまでの回転数で評価した。Abrasion Resistance Test of Magnetic Tape The magnetic surface of the obtained magnetic tape was evaluated using a taper set abrasion tester based on the number of revolutions until the magnetic layer fell off.
く磁気テープの耐久性試験〉
得られた各磁気テープをガラス管に巻きつけ７０℃、９
５係相対湿度で５００時間保存し、さらに常温で２４時
間放置した後、ガラス管から磁気テープを巻き解いた際
の磁性層とポリエステルフィルム間で粘着があるか否か
を観察して評価を行った。各磁気テープの光沢１表面荒
さ、角型比。Durability test of magnetic tapes Each of the obtained magnetic tapes was wound around a glass tube and heated at 70°C for 9
After being stored for 500 hours at a relative humidity of 5% and then left at room temperature for 24 hours, evaluation was made by observing whether there was any adhesion between the magnetic layer and the polyester film when the magnetic tape was unwound from the glass tube. Ta. Gloss 1 surface roughness and squareness ratio of each magnetic tape.
耐摩耗性及び耐久性の測定結果を表２に示した。Table 2 shows the measurement results of abrasion resistance and durability.
表 ２
脂環族ポリエステルジオールを使用したポリウレタン樹
脂（比較例１及び２）を結合剤とする磁気チーｆ＆５及
び６は、そのポリウレタン樹脂のカレンダー適性が劣る
為に磁性面の表面荒れが大きく光沢が低く、角型比が低
い欠点があった。Table 2 Magnetic chips F&5 and 6, which use polyurethane resin (Comparative Examples 1 and 2) using alicyclic polyester diol as a binder, have a large surface roughness on the magnetic surface and lack of gloss due to the poor calenderability of the polyurethane resin. It had the disadvantage of a low squareness ratio.
分子量が１６，０００のポリウレタン樹脂（比較例３）
を結合剤とする磁気テープ４７は、特に耐久性耐摩耗性
に劣る欠点があった。Polyurethane resin with a molecular weight of 16,000 (Comparative Example 3)
The magnetic tape 47 using the binder as a binder has a disadvantage in that it is particularly poor in durability and abrasion resistance.
Claims (1)
るか、該ジオール成分とラクトンとから得られる脂肪族
ポリエステルジオール、 （Ｂ）脂環族ジオールからなる鎖伸長剤、 （Ｃ）有機ジイソシアネートからなり、 かつ得られるポリウレタン樹脂中の脂環族環の含有量が
２〜１５重量％、かつ有機ジイソシアネート（Ｃ）の含
有量が、１０〜５５重量％であり、該樹脂の分子量が３
０，０００〜２００，０００であることを特徴とする熱
可塑性ポリウレタン樹脂組成物。[Scope of Claims] (A) an aliphatic polyester diol obtained from an aliphatic acid component and an aliphatic diol component, or from the diol component and a lactone; (B) a chain extender comprising an alicyclic diol; , (C) consists of an organic diisocyanate, and the content of alicyclic rings in the obtained polyurethane resin is 2 to 15% by weight, and the content of the organic diisocyanate (C) is 10 to 55% by weight, The molecular weight of the resin is 3
A thermoplastic polyurethane resin composition having a molecular weight of 0,000 to 200,000.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61287261A JPS63139909A (en) | 1986-12-02 | 1986-12-02 | Thermoplastic polyurethane resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61287261A JPS63139909A (en) | 1986-12-02 | 1986-12-02 | Thermoplastic polyurethane resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63139909A true JPS63139909A (en) | 1988-06-11 |
Family
ID=17715109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61287261A Pending JPS63139909A (en) | 1986-12-02 | 1986-12-02 | Thermoplastic polyurethane resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63139909A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02108225A (en) * | 1988-10-17 | 1990-04-20 | Tdk Corp | Magnetic recording medium |
| EP0676431A1 (en) * | 1994-04-06 | 1995-10-11 | Imperial Chemical Industries Plc | Coating compositions |
| US5616680A (en) * | 1994-10-04 | 1997-04-01 | Hoechst Celanese Corporation | Process for producing liquid crystal polymer |
| US6624272B2 (en) | 1999-12-20 | 2003-09-23 | Jsr Corporation | Hollow crosslinked cationic polymer particles, method of producing said particles, and paint composition, cationic electrodeposition paint composition, resin composition, filled paper, paper coating composition, and coated paper |
| CN112979899A (en) * | 2019-12-16 | 2021-06-18 | 高鼎精密材料股份有限公司 | High-reverse-dialing elastic biomass water-based PU resin and formula development technology |
-
1986
- 1986-12-02 JP JP61287261A patent/JPS63139909A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02108225A (en) * | 1988-10-17 | 1990-04-20 | Tdk Corp | Magnetic recording medium |
| EP0676431A1 (en) * | 1994-04-06 | 1995-10-11 | Imperial Chemical Industries Plc | Coating compositions |
| US5616680A (en) * | 1994-10-04 | 1997-04-01 | Hoechst Celanese Corporation | Process for producing liquid crystal polymer |
| US6624272B2 (en) | 1999-12-20 | 2003-09-23 | Jsr Corporation | Hollow crosslinked cationic polymer particles, method of producing said particles, and paint composition, cationic electrodeposition paint composition, resin composition, filled paper, paper coating composition, and coated paper |
| CN112979899A (en) * | 2019-12-16 | 2021-06-18 | 高鼎精密材料股份有限公司 | High-reverse-dialing elastic biomass water-based PU resin and formula development technology |
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