JPS59157074A - 変性トリス（２−ヒドロキシエチル）イソシアヌレ−トの製造方法 - Google Patents
変性トリス（２−ヒドロキシエチル）イソシアヌレ−トの製造方法Info
- Publication number
- JPS59157074A JPS59157074A JP58032639A JP3263983A JPS59157074A JP S59157074 A JPS59157074 A JP S59157074A JP 58032639 A JP58032639 A JP 58032639A JP 3263983 A JP3263983 A JP 3263983A JP S59157074 A JPS59157074 A JP S59157074A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyethyl
- tris
- isocyanurate
- caprolactone
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical class OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000009257 reactivity Effects 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- 150000007513 acids Chemical class 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000012948 isocyanate Substances 0.000 abstract description 3
- 150000002513 isocyanates Chemical class 0.000 abstract description 3
- 229920000728 polyester Polymers 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 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 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000012299 nitrogen atmosphere Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000007983 Tris buffer Substances 0.000 description 16
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- -1 2-hydroxyethyl isocyanurate Chemical compound 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 2
- ZSUXOVNWDZTCFN-UHFFFAOYSA-L tin(ii) bromide Chemical compound Br[Sn]Br ZSUXOVNWDZTCFN-UHFFFAOYSA-L 0.000 description 2
- JTDNNCYXCFHBGG-UHFFFAOYSA-L tin(ii) iodide Chemical compound I[Sn]I JTDNNCYXCFHBGG-UHFFFAOYSA-L 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical class CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- SZXKSDXHODZTFS-UHFFFAOYSA-N 4-[4,5-bis[4-(dimethylamino)phenyl]-1H-imidazol-2-yl]-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(C=2NC(=C(N=2)C=2C=CC(=CC=2)N(C)C)C=2C=CC(=CC=2)N(C)C)=C1 SZXKSDXHODZTFS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-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
- 102000010410 Nogo Proteins Human genes 0.000 description 1
- 108010077641 Nogo Proteins Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-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
- 239000000654 additive Substances 0.000 description 1
- 239000013040 bath agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 229940108184 stannous iodide Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58032639A JPS59157074A (ja) | 1983-02-28 | 1983-02-28 | 変性トリス（２−ヒドロキシエチル）イソシアヌレ−トの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58032639A JPS59157074A (ja) | 1983-02-28 | 1983-02-28 | 変性トリス（２−ヒドロキシエチル）イソシアヌレ−トの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59157074A true JPS59157074A (ja) | 1984-09-06 |
| JPH0417951B2 JPH0417951B2 (enrdf_load_stackoverflow) | 1992-03-26 |
Family
ID=12364417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58032639A Granted JPS59157074A (ja) | 1983-02-28 | 1983-02-28 | 変性トリス（２−ヒドロキシエチル）イソシアヌレ−トの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59157074A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010112179A1 (en) * | 2009-04-03 | 2010-10-07 | Cook Composites And Polymers Company | Thermosetting compositions containing isocyanurate rings |
| FR2951719A1 (fr) * | 2009-10-22 | 2011-04-29 | Seppic Sa | Agent reticulant et ignifugeant pour mousse de polyurethane |
| FR2951718A1 (fr) * | 2009-10-22 | 2011-04-29 | Seppic Sa | Agent reticulant et ignifugeant pour mousse de polyurethane |
| US8546486B2 (en) | 2007-09-18 | 2013-10-01 | Ccp Composites Us Llc | Low VOC thermosetting polyester acrylic resin for gel coat |
| JP2014196470A (ja) * | 2013-03-05 | 2014-10-16 | 株式会社Adeka | 三官能型粘性調整剤 |
| JP2015232111A (ja) * | 2014-05-13 | 2015-12-24 | 日本化薬株式会社 | 多官能酸無水物、それを用いた熱硬化性樹脂組成物、及びその硬化物 |
| CN114402034A (zh) * | 2019-09-17 | 2022-04-26 | 株式会社大赛璐 | 组合物及其固化物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660327A (en) * | 1970-06-08 | 1972-05-02 | George Co P D | Lactone or lactam pre-esterified isocyanurate-containing resins |
| JPS48103594A (enrdf_load_stackoverflow) * | 1972-03-08 | 1973-12-25 |
-
1983
- 1983-02-28 JP JP58032639A patent/JPS59157074A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660327A (en) * | 1970-06-08 | 1972-05-02 | George Co P D | Lactone or lactam pre-esterified isocyanurate-containing resins |
| JPS48103594A (enrdf_load_stackoverflow) * | 1972-03-08 | 1973-12-25 |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8546486B2 (en) | 2007-09-18 | 2013-10-01 | Ccp Composites Us Llc | Low VOC thermosetting polyester acrylic resin for gel coat |
| WO2010112179A1 (en) * | 2009-04-03 | 2010-10-07 | Cook Composites And Polymers Company | Thermosetting compositions containing isocyanurate rings |
| US8501877B2 (en) | 2009-04-03 | 2013-08-06 | Ccp Composites Us Llc | Thermosetting compositions containing isocyanurate rings |
| US8637612B2 (en) | 2009-04-03 | 2014-01-28 | Ccp Composites Us Llc | Thermosetting compositions containing isocyanurate ring |
| US9346909B2 (en) | 2009-04-03 | 2016-05-24 | Ccp Composites Us Llc | Thermosetting compositions containing isocyanurate rings |
| EA025765B1 (ru) * | 2009-04-03 | 2017-01-30 | Ссп Композитс Юс Ллс | Термоотверждающиеся композиции, содержащие изоциануратные кольца |
| FR2951719A1 (fr) * | 2009-10-22 | 2011-04-29 | Seppic Sa | Agent reticulant et ignifugeant pour mousse de polyurethane |
| FR2951718A1 (fr) * | 2009-10-22 | 2011-04-29 | Seppic Sa | Agent reticulant et ignifugeant pour mousse de polyurethane |
| JP2014196470A (ja) * | 2013-03-05 | 2014-10-16 | 株式会社Adeka | 三官能型粘性調整剤 |
| JP2015232111A (ja) * | 2014-05-13 | 2015-12-24 | 日本化薬株式会社 | 多官能酸無水物、それを用いた熱硬化性樹脂組成物、及びその硬化物 |
| CN114402034A (zh) * | 2019-09-17 | 2022-04-26 | 株式会社大赛璐 | 组合物及其固化物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0417951B2 (enrdf_load_stackoverflow) | 1992-03-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS60155276A (ja) | ウレタンアクリレ−ト単量体を含有する紫外線硬化性配合物 | |
| JPS62249992A (ja) | 新規なシリコンウレタン（メタ）アクリレ−ト，これを用いた樹脂組成物およびコ−テイング剤 | |
| JPS59157074A (ja) | 変性トリス（２−ヒドロキシエチル）イソシアヌレ−トの製造方法 | |
| JPH0125322B2 (enrdf_load_stackoverflow) | ||
| JP2000053628A (ja) | フルオレン骨格を有するウレタン（メタ）アクリレート | |
| US4727126A (en) | Novel diol monomers and polymers thereof | |
| JPS6366307B2 (enrdf_load_stackoverflow) | ||
| JPS59112957A (ja) | ウレタン基ならびに末端位の（メタ）アクリルエステル基を有する化合物の製法、新規メタクリル酸エステルおよび無気条件下に硬化する接着−および封止材 | |
| JPS6128518A (ja) | 伸展性を有するポリウレタン塗料用プレポリマ−の製造方法 | |
| JP2868191B2 (ja) | ウレタン（メタ）アクリレート、これを用いた樹脂組成物、光ファイバー用コーティング剤及び硬化物 | |
| JPS62230814A (ja) | 光硬化性組成物 | |
| JPH03247618A (ja) | 紫外線硬化型耐熱性ウレタンアクリレート | |
| JPH09194560A (ja) | 湿気硬化性組成物 | |
| CN100386346C (zh) | 含高分子链段的裂解型光引发剂及其制备方法和用途 | |
| JPS59157112A (ja) | ウレタンアクリレ−トオリゴマ−の製造方法 | |
| JP2849240B2 (ja) | 防曇組成物用の活性エネルギー線硬化型オリゴマー | |
| JP2001146577A (ja) | ウレタン樹脂組成物 | |
| JPH0588276B2 (enrdf_load_stackoverflow) | ||
| JPH03143913A (ja) | 多官能ウレタンアクリレート | |
| JPS6236350A (ja) | ポリイソシアネ−ト | |
| JPH0516451B2 (enrdf_load_stackoverflow) | ||
| JP2889715B2 (ja) | カプロラクトン変性ヒドロキシアルキルアクリル酸エステル又はメタクリル酸エステルの製造方法 | |
| JPH10195170A (ja) | 新規なウレタン（メタ）アクリレートおよびその重合性組成物 | |
| JPS6341520A (ja) | ポリウレタン（メタ）アクリレ−ト樹脂組成物 | |
| JPH01229022A (ja) | 反応性光重合開始剤、樹脂組成物及びコーティング剤 |