JPS6318608B2 - - Google Patents

Info

Publication number: JPS6318608B2
Authority: JP; Japan
Prior art keywords: polyurethane; molecular weight; group; item; weight
Prior art date: 1980-03-18
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

JP55035683A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55133420A (en

Inventor

Gibusu Amonzu Baanon

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.)

PPG Industries Inc

Original Assignee

PPG 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.)

1980-03-18

Filing date

1980-03-18

Publication date

1988-04-19

1980-03-18 Application filed by PPG Industries Inc filed Critical PPG Industries Inc

1980-03-18 Priority to JP3568380A priority Critical patent/JPS55133420A/ja

1980-10-17 Publication of JPS55133420A publication Critical patent/JPS55133420A/ja

1988-04-19 Publication of JPS6318608B2 publication Critical patent/JPS6318608B2/ja

Status Granted legal-status Critical Current

Links

239000004814 polyurethane Substances 0.000 claims description 55
229920002635 polyurethane Polymers 0.000 claims description 55
239000000203 mixture Substances 0.000 claims description 39
150000002009 diols Chemical class 0.000 claims description 31
-1 aliphatic polyol Chemical class 0.000 claims description 23
238000000034 method Methods 0.000 claims description 13
229920001187 thermosetting polymer Polymers 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
125000005442 diisocyanate group Chemical group 0.000 claims description 8
239000011347 resin Substances 0.000 claims description 6
229920005989 resin Polymers 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
125000002723 alicyclic group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000004634 thermosetting polymer Substances 0.000 claims description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
229920005862 polyol Polymers 0.000 claims 1
229920005749 polyurethane resin Polymers 0.000 claims 1
239000000047 product Substances 0.000 description 31
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 22
229920000515 polycarbonate Polymers 0.000 description 22
239000004417 polycarbonate Substances 0.000 description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
239000001257 hydrogen Substances 0.000 description 21
229910052739 hydrogen Inorganic materials 0.000 description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 description 14
239000000463 material Substances 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 13
239000000376 reactant Substances 0.000 description 12
239000005056 polyisocyanate Substances 0.000 description 10
229920001228 polyisocyanate Polymers 0.000 description 10
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
125000002947 alkylene group Chemical group 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
239000000126 substance Substances 0.000 description 9
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
238000005299 abrasion Methods 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
238000004132 cross linking Methods 0.000 description 5
125000002993 cycloalkylene group Chemical group 0.000 description 5
230000000694 effects Effects 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
239000004033 plastic Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 4
239000005357 flat glass Substances 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
NONOKGVFTBWRLD-UHFFFAOYSA-N thioisocyanate group Chemical group S(N=C=O)N=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 4
229910052721 tungsten Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
229920000178 Acrylic resin Polymers 0.000 description 3
239000004925 Acrylic resin Substances 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
150000003384 small molecules Chemical class 0.000 description 3
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000005266 casting Methods 0.000 description 2
238000001723 curing Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
239000005350 fused silica glass Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 2
229920005668 polycarbonate resin Polymers 0.000 description 2
239000004431 polycarbonate resin Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000002834 transmittance Methods 0.000 description 2
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
229940035437 1,3-propanediol Drugs 0.000 description 1
239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 1
QERPRBXFYXTKDD-UHFFFAOYSA-N 2-hexyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CCCCCCC(CO)(CO)CO QERPRBXFYXTKDD-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
239000005058 Isophorone diisocyanate Substances 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241000276498 Pollachius virens Species 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
239000012963 UV stabilizer Substances 0.000 description 1
ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
229920006397 acrylic thermoplastic Polymers 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005910 alkyl carbonate group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
DFFDSQBEGQFJJU-UHFFFAOYSA-N butyl hydrogen carbonate Chemical class CCCCOC(O)=O DFFDSQBEGQFJJU-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
125000004956 cyclohexylene group Chemical group 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000007872 degassing Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000013007 heat curing Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
239000004632 polycaprolactone Substances 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005336 safety glass Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
229940071182 stannate Drugs 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

JP3568380A 1980-03-18 1980-03-18 Polyurethane thermosetting resin Granted JPS55133420A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP3568380A JPS55133420A (en)	1980-03-18	1980-03-18	Polyurethane thermosetting resin

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3568380A JPS55133420A (en)	1980-03-18	1980-03-18	Polyurethane thermosetting resin

Publications (2)

Publication Number	Publication Date
JPS55133420A JPS55133420A (en)	1980-10-17
JPS6318608B2 true JPS6318608B2 (de)	1988-04-19

Family

ID=12448682

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3568380A Granted JPS55133420A (en)	1980-03-18	1980-03-18	Polyurethane thermosetting resin

Country Status (1)

Country	Link
JP (1)	JPS55133420A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2236536B1 (de) *	2005-12-16	2012-11-28	PPG Industries Ohio, Inc.	Polyurethanharnstoffe sowie Verfahren zu deren Herstellung

1980
- 1980-03-18 JP JP3568380A patent/JPS55133420A/ja active Granted

Also Published As

Publication number	Publication date
JPS55133420A (en)	1980-10-17

Publication	Publication Date	Title
US4101529A (en)	1978-07-18	Hard, optically clear polyurethane articles
EP0298611B1 (de)	1993-08-04	Mittels 2-Glycerylacrylat oder 2-Glycerylmethacrylat vernetzte Polyurethane und Polyurethan-Polyharnstoffe
US4024113A (en)	1977-05-17	Polycarbonate polyurethanes based on particular aliphatic/cycloaliphatic polycarbonates
EP0367445B1 (de)	1995-12-13	Extruder-Polymerisation von Polyurethanen
JP3625839B2 (ja)	2005-03-02	耐衝撃性ポリウレタン及びその製造方法
EP0302712B1 (de)	1996-11-13	Copolycarbonate
US4160853A (en)	1979-07-10	Catalyst for making polycarbonate diols for use in polycarbonate urethanes
US5574124A (en)	1996-11-12	Isocyanate prepolymers, a process for their preparation and their use
US5627254A (en)	1997-05-06	Rigid thermoplastic plyurethane comprising units of butane diol and a polyethylene glycol
US4366301A (en)	1982-12-28	Crosslinkable thermoplastic polyurethane resins containing ethylenic side groups
EP2150567A1 (de)	2010-02-10	Polyurethanpolymer
US5070172A (en)	1991-12-03	Process for producing polyurethane
JPH07224140A (ja)	1995-08-22	５℃より高温で液体であるポリイソシアネート混合物
CN101155852B (zh)	2011-05-04	具有脂环结构的聚碳酸酯二醇聚合物及其制备方法
JP3266601B2 (ja)	2002-03-18	ポリウレタンの製造におけるハードセグメントのサイズ制御
JPS5922917A (ja)	1984-02-06	耐摩耗性ポリウレタンの製法
JPS6134448B2 (de)	1986-08-07
GB1586436A (en)	1981-03-18	Process for the preparation of carbonic acid aryl esters
JPS6318608B2 (de)	1988-04-19
JP2582575B2 (ja)	1997-02-19	樹脂組成物及びコ−ティング剤
US4594402A (en)	1986-06-10	Long chain hydrocarbon and fluorocarbon reactive internal release agents for condensation polymers
JP3301447B2 (ja)	2002-07-15	ウレタン・不飽和オルガノオリゴマーとその製造方法
JPH02158617A (ja)	1990-06-19	ポリウレタンの製造方法
WO1996023827A1 (en)	1996-08-08	Impact resistant polyurethane and method of manufacture thereof
CA1114988A (en)	1981-12-22	Hard, optically clear polyurethane articles