CA1221982A - 1,3,5-tris-(1-isocyanatomethylethyl)-benzene - Google Patents

1,3,5-tris-(1-isocyanatomethylethyl)-benzene

Info

Publication number: CA1221982A
Authority: CA; Canada
Prior art keywords: benzene; tris; moles; tpti; added
Prior art date: 1982-12-27
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

CA000505255A

Other languages

English (en)

Inventor

Balwant Singh

Peter S. Forgione

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid Co

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.)

1982-12-27

Filing date

1986-03-26

Publication date

1987-05-19

1982-12-27 Priority claimed from US06/453,681 external-priority patent/US4633010A/en

1986-03-26 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1986-03-26 Priority to CA000505255A priority Critical patent/CA1221982A/fr

1987-05-19 Application granted granted Critical

1987-05-19 Publication of CA1221982A publication Critical patent/CA1221982A/fr

1995-10-27 Priority claimed from JP28013895A external-priority patent/JPH09130263A/ja

Status Expired legal-status Critical Current

Links

UHOOXEZDFAUNSL-UHFFFAOYSA-N 1,3,5-tris(1-isocyanatopropan-2-yl)benzene Chemical compound O=C=NCC(C)C1=CC(C(C)CN=C=O)=CC(C(C)CN=C=O)=C1 UHOOXEZDFAUNSL-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 6
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 10
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 5
LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000012948 isocyanate Substances 0.000 abstract description 11
150000002513 isocyanates Chemical class 0.000 abstract description 5
239000011527 polyurethane coating Substances 0.000 abstract description 5
238000000034 method Methods 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract 2
230000000875 corresponding effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
-1 aliphatic isocyanates Chemical class 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000007787 solid Substances 0.000 description 7
OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000007983 Tris buffer Substances 0.000 description 5
238000007792 addition Methods 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
JYEFXLLEDLBLOB-UHFFFAOYSA-N 1,3,5-tris(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC(C(C)(C)N=C=O)=CC(C(C)(C)N=C=O)=C1 JYEFXLLEDLBLOB-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 3
239000007789 gas Substances 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
SRNQAQUOOIZPJL-UHFFFAOYSA-N 1,3,5-tris(2-chloropropan-2-yl)benzene Chemical compound CC(C)(Cl)C1=CC(C(C)(C)Cl)=CC(C(C)(C)Cl)=C1 SRNQAQUOOIZPJL-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
238000001321 HNCO Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000011701 zinc Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
BHGQSXUNEGPBCB-UHFFFAOYSA-N 1,2,3-tris(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1C(C)=C BHGQSXUNEGPBCB-UHFFFAOYSA-N 0.000 description 1
CWABICBDFJMISP-UHFFFAOYSA-N 1,3,5-tris(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC(C(C)=C)=CC(C(C)=C)=C1 CWABICBDFJMISP-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
XBXFGOSIPGWNLZ-UHFFFAOYSA-N O=C1C=C(CC(C)(C)C1)C.N=C=O Chemical compound O=C1C=C(CC(C)(C)C1)C.N=C=O XBXFGOSIPGWNLZ-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
RVZHUQPIBHMAEX-UHFFFAOYSA-N sodium;isocyanate Chemical compound [Na+].[N-]=C=O RVZHUQPIBHMAEX-UHFFFAOYSA-N 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000013638 trimer Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyurethanes Or Polyureas (AREA)

CA000505255A 1982-12-27 1986-03-26 1,3,5-tris-(1-isocyanatomethylethyl)-benzene Expired CA1221982A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000505255A CA1221982A (fr)	1982-12-27	1986-03-26	1,3,5-tris-(1-isocyanatomethylethyl)-benzene

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US06/453,681 US4633010A (en)	1982-12-27	1982-12-27	Tertiary aralkyl triurethane
US453,681		1982-12-27
CA000444246A CA1223880A (fr)	1982-12-27	1983-12-23	1,3,5-tris(1-isocyanatomethylethyl)-benzene
CA000505255A CA1221982A (fr)	1982-12-27	1986-03-26	1,3,5-tris-(1-isocyanatomethylethyl)-benzene
JP28013895A JPH09130263A (ja)	1995-10-27	1995-10-27	データ通信装置、符号化装置及び復号化装置

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000444246A Division CA1223880A (fr)	1982-12-27	1983-12-23	1,3,5-tris(1-isocyanatomethylethyl)-benzene

Publications (1)

Publication Number	Publication Date
CA1221982A true CA1221982A (fr)	1987-05-19

Family

ID=27167402

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000505255A Expired CA1221982A (fr)	1982-12-27	1986-03-26	1,3,5-tris-(1-isocyanatomethylethyl)-benzene

Country Status (1)

Country	Link
CA (1)	CA1221982A (fr)

1986
- 1986-03-26 CA CA000505255A patent/CA1221982A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-05-19	MKEX	Expiry

Publication	Publication Date	Title
KR910002533B1 (ko)	1991-04-23	3급 아르알킬 우레탄 및 그 유도체의 제조방법
US3903126A (en)	1975-09-02	Manufacture of biuret group-containing polyisocyanates
US4399074A (en)	1983-08-16	Preparation of tertiary alkyl isocyanates
GB1043673A (en)	1966-09-21	A process for the production of polyisocyanates with a biuret structure
US4570012A (en)	1986-02-11	Urethanes from tertiary aralkyl diols
JPH0881458A (ja)	1996-03-26	１，３−ジオキサン−２−オン基含有オリゴウレタン
CA1221982A (fr)	1987-05-19	1,3,5-tris-(1-isocyanatomethylethyl)-benzene
EP0016441B1 (fr)	1982-05-12	Procédé pour la préparation d'un mélange de dicarbamates de diphénylméthane et de carbamates de polyméthylène polyphényle
US4633010A (en)	1986-12-30	Tertiary aralkyl triurethane
US4882385A (en)	1989-11-21	1,3,5-tris(1-isocyanatomethylethyl)benzene in polyurethanes
JPS63183553A (ja)	1988-07-28	メチルカルバメートのリモネンへの付加によるシクロヘキシルモノーおよびジーウレタンの製造法
EP0083685B1 (fr)	1985-03-06	Préparation de diisocyanates
US4399073A (en)	1983-08-16	Preparation of tertiary alkyl isocyanates
US4879410A (en)	1989-11-07	Preparation of primary aralkyl urethanes and ureas and isocyanates derived therefrom
US4259255A (en)	1981-03-31	Process for the production of isocyanates
US4325887A (en)	1982-04-20	Isocyanatoaryl sulfonic acid esters
EP0088218B1 (fr)	1985-05-08	Procédé de préparation d'isocyanates d'alcoyle tertiaire
US5344965A (en)	1994-09-06	Preparation of a novel diisocyanate from norbornadiene
EP0115614B1 (fr)	1989-02-08	Fabrication d'uréthanes au départ d'aralcoyl diols tertiaires
US4395369A (en)	1983-07-26	Manufacture of isocyanate
JPS6340421B2 (fr)	1988-08-11
JPH0358966A (ja)	1991-03-14	モノーおよびオリゴウレタンの製造方法
EP0164494B1 (fr)	1987-08-26	Système pour transporter des articles coniques
US3868399A (en)	1975-02-25	Chlorinated alkoxyphenylisocyanates
US4724256A (en)	1988-02-09	Urethane linked hydroxy aromatic isocyanates