JPS6249883B2 - - Google Patents

Info

Publication number: JPS6249883B2
Authority: JP; Japan
Prior art keywords: group; hydrogen; lower alkyl; substituted; benzyl
Prior art date: 1983-10-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP58192634A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6086116A (ja

Inventor

Toshio Shimizu

Tsugi Higuchi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Toray Industries Inc

Original Assignee

Toray Industries Inc

Priority date (The priority date 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 date listed.)

1983-10-17

Filing date

1983-10-17

Publication date

1987-10-21

1983-10-17 Application filed by Toray Industries Inc filed Critical Toray Industries Inc

1983-10-17 Priority to JP58192634A priority Critical patent/JPS6086116A/ja

1985-05-15 Publication of JPS6086116A publication Critical patent/JPS6086116A/ja

1987-10-21 Publication of JPS6249883B2 publication Critical patent/JPS6249883B2/ja

Status Granted legal-status Critical Current

Links

-1 isocyanate compound Chemical class 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 33
229920002635 polyurethane Polymers 0.000 claims description 32
239000004814 polyurethane Substances 0.000 claims description 32
239000012948 isocyanate Substances 0.000 claims description 25
229920005862 polyol Polymers 0.000 claims description 20
150000003077 polyols Chemical class 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
239000007795 chemical reaction product Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000002009 diols Chemical group 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
125000001142 dicarboxylic acid group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
125000003545 alkoxy group Chemical group 0.000 claims 6
150000002431 hydrogen Chemical group 0.000 claims 4
125000004093 cyano group Chemical group *C#N 0.000 claims 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
229920006395 saturated elastomer Polymers 0.000 claims 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 31
150000001875 compounds Chemical class 0.000 description 15
229920000642 polymer Polymers 0.000 description 15
150000001412 amines Chemical class 0.000 description 13
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 10
239000000178 monomer Substances 0.000 description 9
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
150000002513 isocyanates Chemical class 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
239000002649 leather substitute Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 5
239000004970 Chain extender Substances 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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 4
239000011248 coating agent Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
239000003973 paint Substances 0.000 description 4
229920001610 polycaprolactone Polymers 0.000 description 4
239000007787 solid Substances 0.000 description 4
CGXOAAMIQPDTPE-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CN1C(C)(C)CC(N)CC1(C)C CGXOAAMIQPDTPE-UHFFFAOYSA-N 0.000 description 3
NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 description 3
FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
239000004721 Polyphenylene oxide Substances 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
238000005108 dry cleaning Methods 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
125000002768 hydroxyalkyl group Chemical group 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000570 polyether Polymers 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
AMAMTFYJXKJFBH-UHFFFAOYSA-N 1-benzyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1CC1=CC=CC=C1 AMAMTFYJXKJFBH-UHFFFAOYSA-N 0.000 description 2
VLTHAKKFNPUWSB-UHFFFAOYSA-N 1-benzyl-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1CC1=CC=CC=C1 VLTHAKKFNPUWSB-UHFFFAOYSA-N 0.000 description 2
VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
229910001209 Low-carbon steel Inorganic materials 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-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
125000005442 diisocyanate group Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010528 free radical solution polymerization reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000010409 ironing Methods 0.000 description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
230000005923 long-lasting effect Effects 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000004632 polycaprolactone Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
239000000376 reactant Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000000758 substrate Substances 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
238000005406 washing Methods 0.000 description 2
238000004383 yellowing Methods 0.000 description 2
DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 1
POTYORUTRLSAGZ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) prop-2-enoate Chemical compound ClCC(O)COC(=O)C=C POTYORUTRLSAGZ-UHFFFAOYSA-N 0.000 description 1
GLFNAKWJKOQJNT-UHFFFAOYSA-N 1,2,2,6,6-pentamethyl-4-phenylpiperidin-4-ol Chemical compound C1C(C)(C)N(C)C(C)(C)CC1(O)C1=CC=CC=C1 GLFNAKWJKOQJNT-UHFFFAOYSA-N 0.000 description 1
FHSMJSFOSXRNES-UHFFFAOYSA-N 1,2,2-trimethyl-1-azaspiro[5.5]undecan-4-amine Chemical compound CN1C(C)(C)CC(N)CC11CCCCC1 FHSMJSFOSXRNES-UHFFFAOYSA-N 0.000 description 1
NSCVEXDDAGYATM-UHFFFAOYSA-N 1,2,2-trimethyl-1-azaspiro[5.5]undecan-4-ol Chemical compound CN1C(C)(C)CC(O)CC11CCCCC1 NSCVEXDDAGYATM-UHFFFAOYSA-N 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
229940058015 1,3-butylene glycol Drugs 0.000 description 1
PUZXLFQBRGGQEY-UHFFFAOYSA-N 1,3-dioxonane-4,9-dione Chemical compound O=C1CCCCC(=O)OCO1 PUZXLFQBRGGQEY-UHFFFAOYSA-N 0.000 description 1
OFIMUXHNLPZBDO-UHFFFAOYSA-N 1-benzyl-2,2,6,6-tetramethyl-4-phenylpiperidin-4-ol Chemical compound CC1(C)CC(O)(C=2C=CC=CC=2)CC(C)(C)N1CC1=CC=CC=C1 OFIMUXHNLPZBDO-UHFFFAOYSA-N 0.000 description 1
AMHNWQMJFIQASF-UHFFFAOYSA-N 1-benzyl-2,2-diethyl-6,6-dimethylpiperidin-4-amine Chemical compound CCC1(CC)CC(N)CC(C)(C)N1CC1=CC=CC=C1 AMHNWQMJFIQASF-UHFFFAOYSA-N 0.000 description 1
STUHEEYBNUBGDH-UHFFFAOYSA-N 1-benzyl-2,2-diethyl-6,6-dimethylpiperidin-4-ol Chemical compound CCC1(CC)CC(O)CC(C)(C)N1CC1=CC=CC=C1 STUHEEYBNUBGDH-UHFFFAOYSA-N 0.000 description 1
NCRLIOVBQDWRCW-UHFFFAOYSA-N 1-benzyl-2,2-dimethyl-1-azaspiro[5.5]undecan-4-amine Chemical compound C=1C=CC=CC=1CN1C(C)(C)CC(N)CC21CCCCC2 NCRLIOVBQDWRCW-UHFFFAOYSA-N 0.000 description 1
KAYGSJSLWDFMJQ-UHFFFAOYSA-N 1-benzyl-2,2-dimethyl-1-azaspiro[5.5]undecan-4-ol Chemical compound C=1C=CC=CC=1CN1C(C)(C)CC(O)CC21CCCCC2 KAYGSJSLWDFMJQ-UHFFFAOYSA-N 0.000 description 1
PTSAMJUYPPPFOB-UHFFFAOYSA-N 1-benzyl-2-ethyl-2,6,6-trimethylpiperidin-4-amine Chemical compound CCC1(C)CC(N)CC(C)(C)N1CC1=CC=CC=C1 PTSAMJUYPPPFOB-UHFFFAOYSA-N 0.000 description 1
MYVBVGNLSHJYDS-UHFFFAOYSA-N 1-benzyl-2-ethyl-2,6,6-trimethylpiperidin-4-ol Chemical compound CCC1(C)CC(O)CC(C)(C)N1CC1=CC=CC=C1 MYVBVGNLSHJYDS-UHFFFAOYSA-N 0.000 description 1
IRANSJHFDQYYLN-UHFFFAOYSA-N 1-benzyl-4-ethyl-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(CC)(O)CC(C)(C)N1CC1=CC=CC=C1 IRANSJHFDQYYLN-UHFFFAOYSA-N 0.000 description 1
NFCIMBZDJLFHNB-UHFFFAOYSA-N 2,2,4,6,6-pentamethylpiperidin-4-ol Chemical compound CC1(C)CC(C)(O)CC(C)(C)N1 NFCIMBZDJLFHNB-UHFFFAOYSA-N 0.000 description 1
VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
ANWUNKVMALBHSR-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-phenylpiperidin-4-ol Chemical compound C1C(C)(C)NC(C)(C)CC1(O)C1=CC=CC=C1 ANWUNKVMALBHSR-UHFFFAOYSA-N 0.000 description 1
JFQJBKMTCYNANZ-UHFFFAOYSA-N 2,2-diethyl-1,6,6-trimethylpiperidin-4-amine Chemical compound CCC1(CC)CC(N)CC(C)(C)N1C JFQJBKMTCYNANZ-UHFFFAOYSA-N 0.000 description 1
CIJJWMDFPFCWCZ-UHFFFAOYSA-N 2,2-diethyl-1,6,6-trimethylpiperidin-4-ol Chemical compound CCC1(CC)CC(O)CC(C)(C)N1C CIJJWMDFPFCWCZ-UHFFFAOYSA-N 0.000 description 1
PGPTXEBBLMXPBC-UHFFFAOYSA-N 2,2-diethyl-6,6-dimethylpiperidin-4-amine Chemical compound CCC1(CC)CC(N)CC(C)(C)N1 PGPTXEBBLMXPBC-UHFFFAOYSA-N 0.000 description 1
SKTJKGMWKIKKGI-UHFFFAOYSA-N 2,2-diethyl-6,6-dimethylpiperidin-4-ol Chemical compound CCC1(CC)CC(O)CC(C)(C)N1 SKTJKGMWKIKKGI-UHFFFAOYSA-N 0.000 description 1
QXONKKMHFDOBDZ-UHFFFAOYSA-N 2,2-dimethyl-1-azaspiro[5.5]undecan-4-amine Chemical compound N1C(C)(C)CC(N)CC11CCCCC1 QXONKKMHFDOBDZ-UHFFFAOYSA-N 0.000 description 1
KQFLQICIXFFTQZ-UHFFFAOYSA-N 2,2-dimethyl-1-azaspiro[5.5]undecan-4-ol Chemical compound N1C(C)(C)CC(O)CC11CCCCC1 KQFLQICIXFFTQZ-UHFFFAOYSA-N 0.000 description 1
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
MUGNCLWPYHLVAV-UHFFFAOYSA-N 2-ethyl-1,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCC1(C)CC(N)CC(C)(C)N1C MUGNCLWPYHLVAV-UHFFFAOYSA-N 0.000 description 1
UJFNZOJMVLFBMD-UHFFFAOYSA-N 2-ethyl-1,2,6,6-tetramethylpiperidin-4-ol Chemical compound CCC1(C)CC(O)CC(C)(C)N1C UJFNZOJMVLFBMD-UHFFFAOYSA-N 0.000 description 1
JSHYJTOWIPTKAI-UHFFFAOYSA-N 2-ethyl-2,6,6-trimethylpiperidin-4-amine Chemical compound CCC1(C)CC(N)CC(C)(C)N1 JSHYJTOWIPTKAI-UHFFFAOYSA-N 0.000 description 1
GBRQBWGSVYCIBF-UHFFFAOYSA-N 2-ethyl-2,6,6-trimethylpiperidin-4-ol Chemical compound CCC1(C)CC(O)CC(C)(C)N1 GBRQBWGSVYCIBF-UHFFFAOYSA-N 0.000 description 1
NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 1
ZWMJUBVSXUPLKD-UHFFFAOYSA-N 2-hydroxypentyl 2-methylprop-2-enoate Chemical compound CCCC(O)COC(=O)C(C)=C ZWMJUBVSXUPLKD-UHFFFAOYSA-N 0.000 description 1
GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
JZMBVZKTMHMISV-UHFFFAOYSA-N 4-ethyl-1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(CC(CC1(C)C)(O)CC)(C)C JZMBVZKTMHMISV-UHFFFAOYSA-N 0.000 description 1
GCQYGOGEJYKAHX-UHFFFAOYSA-N 4-ethyl-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CCC1(O)CC(C)(C)NC(C)(C)C1 GCQYGOGEJYKAHX-UHFFFAOYSA-N 0.000 description 1
YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
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KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000353345 Odontesthes regia Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
SBYMUDUGTIKLCR-VOTSOKGWSA-N [(e)-2-chloroethenyl]benzene Chemical compound Cl\C=C\C1=CC=CC=C1 SBYMUDUGTIKLCR-VOTSOKGWSA-N 0.000 description 1
BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
238000007259 addition reaction Methods 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
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000012662 bulk polymerization Methods 0.000 description 1
235000019437 butane-1,3-diol Nutrition 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011247 coating layer Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
125000004427 diamine group Chemical group 0.000 description 1
UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
238000010292 electrical insulation Methods 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000003827 glycol group Chemical group 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
GFMIDCCZJUXASS-UHFFFAOYSA-N hexane-1,1,6-triol Chemical compound OCCCCCC(O)O GFMIDCCZJUXASS-UHFFFAOYSA-N 0.000 description 1
238000009981 jet dyeing Methods 0.000 description 1
230000007774 longterm Effects 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920001748 polybutylene Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000921 polyethylene adipate Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
239000011527 polyurethane coating Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
238000010557 suspension polymerization reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
Polyurethanes Or Polyureas (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

JP58192634A 1983-10-17 1983-10-17 ポリウレタン組成物及びその製法 Granted JPS6086116A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP58192634A JPS6086116A (ja)	1983-10-17	1983-10-17	ポリウレタン組成物及びその製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58192634A JPS6086116A (ja)	1983-10-17	1983-10-17	ポリウレタン組成物及びその製法

Publications (2)

Publication Number	Publication Date
JPS6086116A JPS6086116A (ja)	1985-05-15
JPS6249883B2 true JPS6249883B2 (fr)	1987-10-21

Family

ID=16294511

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58192634A Granted JPS6086116A (ja)	1983-10-17	1983-10-17	ポリウレタン組成物及びその製法

Country Status (1)

Country	Link
JP (1)	JPS6086116A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103290691A (zh) *	2013-05-21	2013-09-11	江苏宝泽高分子材料股份有限公司	一种合成革用雾面耐刮粉滑感印刷处理剂及其制备方法
CN103290693A (zh) *	2013-06-25	2013-09-11	江苏宝泽高分子材料股份有限公司	一种溶剂型辊涂绒感处理剂及其制备方法
CN103342888B (zh) *	2013-06-26	2015-12-09	江苏宝泽高分子材料股份有限公司	一种肤感倒顺毛羊巴树脂及其制备方法

1983
- 1983-10-17 JP JP58192634A patent/JPS6086116A/ja active Granted

Also Published As

Publication number	Publication date
JPS6086116A (ja)	1985-05-15

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US4956240A (en)	1990-09-11	Use of polysiloxanes containing amino groups as additives in coatings for plastics
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