JPH0742266B2 - 環境指示物質として有用な尿素部分を含むアセチレン性化合物 - Google Patents

環境指示物質として有用な尿素部分を含むアセチレン性化合物

Info

Publication number: JPH0742266B2
Authority: JP; Japan
Prior art keywords: product; reaction; urea; acetylenic; carbon atoms
Prior art date: 1983-07-18
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 - Lifetime

Application number

JP59147432A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6038352A (ja

Inventor

アンソニー・フランク・プレジオシ

タデウス・プラシツク

Original Assignee

アライド・コーポレーシヨン

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.)

1983-07-18

Filing date

1984-07-16

Publication date

1995-05-10

1984-07-16 Application filed by アライド・コーポレーシヨン filed Critical アライド・コーポレーシヨン

1985-02-27 Publication of JPS6038352A publication Critical patent/JPS6038352A/ja

1995-05-10 Publication of JPH0742266B2 publication Critical patent/JPH0742266B2/ja

2010-05-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000007613 environmental effect Effects 0.000 title claims description 21
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 18
125000002534 ethynyl group Chemical group [H]C#C* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 76
125000004432 carbon atom Chemical group C* 0.000 claims description 18
230000008859 change Effects 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
150000002894 organic compounds Chemical class 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
238000002310 reflectometry Methods 0.000 claims 1
239000000047 product Substances 0.000 description 84
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
239000004202 carbamide Substances 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
238000000034 method Methods 0.000 description 23
-1 Alkoxycarbonyl urethane Chemical compound 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000012429 reaction media Substances 0.000 description 21
235000013877 carbamide Nutrition 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
230000015572 biosynthetic process Effects 0.000 description 17
238000005859 coupling reaction Methods 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
238000003786 synthesis reaction Methods 0.000 description 16
229910021591 Copper(I) chloride Inorganic materials 0.000 description 14
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 14
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 14
238000000921 elemental analysis Methods 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000976 ink Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
238000010438 heat treatment Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000012071 phase Substances 0.000 description 11
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 10
RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 9
238000005691 oxidative coupling reaction Methods 0.000 description 9
238000006116 polymerization reaction Methods 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000000463 material Substances 0.000 description 8
230000005855 radiation Effects 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000000758 substrate Substances 0.000 description 8
239000003208 petroleum Substances 0.000 description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000000137 annealing Methods 0.000 description 6
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 6
230000005496 eutectics Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
239000000178 monomer Substances 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
230000009257 reactivity Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
150000003672 ureas Chemical class 0.000 description 5
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 4
150000004985 diamines Chemical class 0.000 description 4
GOQJMMHTSOQIEI-UHFFFAOYSA-N hex-5-yn-1-ol Chemical compound OCCCCC#C GOQJMMHTSOQIEI-UHFFFAOYSA-N 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
238000002955 isolation Methods 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000000123 paper Substances 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
238000007639 printing Methods 0.000 description 4
230000004044 response Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
WQDPSTYGLZXWAX-UHFFFAOYSA-N 1,6-dibromohexa-1,5-diyne Chemical compound BrC#CCCC#CBr WQDPSTYGLZXWAX-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000001186 cumulative effect Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 3
230000003595 spectral effect Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 2
ZSMLAARSCLQOBN-UHFFFAOYSA-N 2-[12-(1,3-dioxoisoindol-2-yl)dodeca-5,7-diynyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCC#CC#CCCCCN1C(=O)C2=CC=CC=C2C1=O ZSMLAARSCLQOBN-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
150000001345 alkine derivatives Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000008139 complexing agent Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000010419 fine particle Substances 0.000 description 2
238000007646 gravure printing Methods 0.000 description 2
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
230000001965 increasing effect Effects 0.000 description 2
238000012544 monitoring process Methods 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000007650 screen-printing Methods 0.000 description 2
238000005507 spraying Methods 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical compound O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 description 1
YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
GCXDUMDOBYMSAB-UHFFFAOYSA-N 5,5-dibromohexa-1,3-diyne Chemical compound BrC(C#CC#C)(C)Br GCXDUMDOBYMSAB-UHFFFAOYSA-N 0.000 description 1
229920002799 BoPET Polymers 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
PWZSWRUIQGSOJS-UHFFFAOYSA-N C(C#C)N.C(CC)NC(=O)N Chemical compound C(C#C)N.C(CC)NC(=O)N PWZSWRUIQGSOJS-UHFFFAOYSA-N 0.000 description 1
HIDSTSYJHSXTBG-UHFFFAOYSA-N C(C#C)N.C(CCC)OC(=O)CNC(=O)N Chemical compound C(C#C)N.C(CCC)OC(=O)CNC(=O)N HIDSTSYJHSXTBG-UHFFFAOYSA-N 0.000 description 1
101100274575 Caenorhabditis elegans clh-3 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
238000005642 Gabriel synthesis reaction Methods 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000005041 Mylar™ Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 1
LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
RMZSOGJUEUFCBK-UHFFFAOYSA-N butyl 2-isocyanatoacetate Chemical compound CCCCOC(=O)CN=C=O RMZSOGJUEUFCBK-UHFFFAOYSA-N 0.000 description 1
239000011111 cardboard Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
NPWBXEUGXOFIGH-UHFFFAOYSA-N dodeca-5,7-diyne-1,12-diamine Chemical compound NCCCCC#CC#CCCCCN NPWBXEUGXOFIGH-UHFFFAOYSA-N 0.000 description 1
SEWYHOMCDKWYEF-UHFFFAOYSA-N dodeca-5,7-diyne-1,12-diol Chemical compound OCCCCC#CC#CCCCCO SEWYHOMCDKWYEF-UHFFFAOYSA-N 0.000 description 1
WRNOAELBRPKVHC-UHFFFAOYSA-N dodecylurea Chemical compound CCCCCCCCCCCCNC(N)=O WRNOAELBRPKVHC-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
DUVOZUPPHBRJJO-UHFFFAOYSA-N ethyl 2-isocyanatoacetate Chemical compound CCOC(=O)CN=C=O DUVOZUPPHBRJJO-UHFFFAOYSA-N 0.000 description 1
239000011094 fiberboard Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
YFIBSNDOVCWPBL-UHFFFAOYSA-N hexa-1,5-diyne Chemical compound C#CCCC#C YFIBSNDOVCWPBL-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000012073 inactive phase Substances 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000007641 inkjet printing Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
ZWISJRCLMTZJIA-UHFFFAOYSA-N methylurea;urea Chemical compound NC(N)=O.CNC(N)=O ZWISJRCLMTZJIA-UHFFFAOYSA-N 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000011087 paperboard Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
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235000013324 preserved food Nutrition 0.000 description 1
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230000000750 progressive effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000004043 responsiveness Effects 0.000 description 1
238000010008 shearing Methods 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heat Sensitive Colour Forming Recording (AREA)
Investigating Materials By The Use Of Optical Means Adapted For Particular Applications (AREA)
Photometry And Measurement Of Optical Pulse Characteristics (AREA)
Measuring Temperature Or Quantity Of Heat (AREA)
Investigating Or Analyzing Materials Using Thermal Means (AREA)

JP59147432A 1983-07-18 1984-07-16 環境指示物質として有用な尿素部分を含むアセチレン性化合物 Expired - Lifetime JPH0742266B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US51439983A	1983-07-18	1983-07-18
US514399		1983-07-18

Related Child Applications (2)

Application Number	Title	Priority Date	Filing Date
JP6253956A Division JP2545703B2 (ja)	1983-07-18	1994-10-19	環境指示物質として有用な、尿素部分を含有するアセチレン性化合物
JP6253884A Division JP2545702B2 (ja)	1983-07-18	1994-10-19	環境指示物質として有用な、尿素部分を含有するアセチレン性化合物

Publications (2)

Publication Number	Publication Date
JPS6038352A JPS6038352A (ja)	1985-02-27
JPH0742266B2 true JPH0742266B2 (ja)	1995-05-10

Family

ID=24046965

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
JP59147432A Expired - Lifetime JPH0742266B2 (ja)	1983-07-18	1984-07-16	環境指示物質として有用な尿素部分を含むアセチレン性化合物
JP6253884A Expired - Lifetime JP2545702B2 (ja)	1983-07-18	1994-10-19	環境指示物質として有用な、尿素部分を含有するアセチレン性化合物
JP6253956A Expired - Lifetime JP2545703B2 (ja)	1983-07-18	1994-10-19	環境指示物質として有用な、尿素部分を含有するアセチレン性化合物

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
JP6253884A Expired - Lifetime JP2545702B2 (ja)	1983-07-18	1994-10-19	環境指示物質として有用な、尿素部分を含有するアセチレン性化合物
JP6253956A Expired - Lifetime JP2545703B2 (ja)	1983-07-18	1994-10-19	環境指示物質として有用な、尿素部分を含有するアセチレン性化合物

Country Status (3)

Country	Link
JP (3)	JPH0742266B2 (fr)
CA (1)	CA1237145A (fr)
DK (1)	DK348884A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
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JP2012522054A (ja) *	2009-03-31	2012-09-20	テンプタイムコーポレイション	共結晶性のジアセチレン単量体組成物、結晶相および混合物、ならびに関連する方法

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US5175307A (en) *	1986-05-16	1992-12-29	Agency Of Industrial Science & Technology	Diacetylene compound having double bond and shaped article thereof
US4987257A (en) *	1986-05-16	1991-01-22	Director-General Of Agency Of Industrial Science And Technology	Diacetylene compound having double bond and shaped article thereof
US5248748A (en) *	1986-05-16	1993-09-28	Dir. General Of Agency Of Industrial Science And Technology	Diacetylene compound having double bond and shaped article thereof
JP3453741B2 (ja) *	1993-07-08	2003-10-06	日本製紙株式会社	感熱記録体
US6046455A (en) *	1998-01-30	2000-04-04	Segan Industries	Integrating ultraviolet exposure detection devices
CA2282084C (fr)	1999-09-10	2005-01-11	Stuart A. Jackson	Dispositif indicateur de rayonnement
CN105037213A (zh) *	2007-10-30	2015-11-11	坦普泰姆公司	晶化的二乙炔指示剂化合物及其制备方法
CN111269128B (zh) *	2020-04-02	2022-08-30	苏州爱玛特生物科技有限公司	1,1′-(六-2,4-二炔-1,6-二基)双(3-烷基脲)类化合物的合成方法

1984
- 1984-06-26 CA CA000457436A patent/CA1237145A/fr not_active Expired
- 1984-07-16 JP JP59147432A patent/JPH0742266B2/ja not_active Expired - Lifetime
- 1984-07-17 DK DK348884A patent/DK348884A/da unknown
1994
- 1994-10-19 JP JP6253884A patent/JP2545702B2/ja not_active Expired - Lifetime
- 1994-10-19 JP JP6253956A patent/JP2545703B2/ja not_active Expired - Lifetime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2012522054A (ja) *	2009-03-31	2012-09-20	テンプタイムコーポレイション	共結晶性のジアセチレン単量体組成物、結晶相および混合物、ならびに関連する方法

Also Published As

Publication number	Publication date
JPH07267916A (ja)	1995-10-17
CA1237145A (fr)	1988-05-24
JPS6038352A (ja)	1985-02-27
JP2545702B2 (ja)	1996-10-23
JP2545703B2 (ja)	1996-10-23
DK348884A (da)	1985-01-19
DK348884D0 (da)	1984-07-17
JPH07258198A (ja)	1995-10-09

Legal Events

Date	Code	Title	Description
2004-02-24	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2004-07-16	EXPY	Cancellation because of completion of term

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JPH0742266B2 - 環境指示物質として有用な尿素部分を含むアセチレン性化合物 - Google Patents

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ID=24046965

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