AU653317B1 - Energetic urethane system curative - Google Patents

Energetic urethane system curative Download PDF

Info

Publication number
AU653317B1
AU653317B1 AU82522/91A AU8252291A AU653317B1 AU 653317 B1 AU653317 B1 AU 653317B1 AU 82522/91 A AU82522/91 A AU 82522/91A AU 8252291 A AU8252291 A AU 8252291A AU 653317 B1 AU653317 B1 AU 653317B1
Authority
AU
Australia
Prior art keywords
bis
curative
azidomethyl
curing
propane
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.)
Ceased
Application number
AU82522/91A
Inventor
Milton Bernard Frankel
Ross Irving Wagner
James Frederick Weber
Edgar Roland Wilson
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.)
Boeing North American Inc
Original Assignee
Rockwell International Corp
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.)
Filing date
Publication date
Application filed by Rockwell International Corp filed Critical Rockwell International Corp
Application granted granted Critical
Publication of AU653317B1 publication Critical patent/AU653317B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/7856—Nitrogen containing azo groups
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
    • C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
    • C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
    • C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
    • C06B45/105—The resin being a polymer bearing energetic groups or containing a soluble organic explosive
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C247/12—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
    • C07C255/12—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C255/65—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms
    • C07C255/67—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to nitrogen atoms having cyano groups and azido groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyurethanes Or Polyureas (AREA)

Description

S 7 Re f: I.S3 L 17
AUSTRALIA
PATENTS ACT l99."' COMPLETE SPECIFICATION FOR A STANDARD PATENT
ORIGINAL
Name and Address of Applicant: Actual Inventor(s): Address for Service: Thventicn T1'tle: Aoclz c-ll Tnit riaL Loil Corjporittioi 22:0a, LTprh ii 7hxy, ~I S0g 1 C tI1- orni 90 2 1 Ul tncl .3 tes or tuica-iz iL~ I 3i-i Ln~ F Jm r ikoI r I do I i i I .3 u 0 So~ruson Ferguson, Parent Attorneys Level 33 St Martins Tower, 31 Market Street Sydney, New South ~ae,2000, Australia Euoargetic Ur' tliuieo Sy.-Aun Curative The ocwing 'Steen a 'u11 oesc-4t: *on o,'r 'is Thnve~:-r. 7t'e cest. method of zterfornving i7 Known to mne/US:- 3 8 d /14
-I-
88R066 ENERGETIC URETHANE SYSTEM CURATIVE BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to solid fuel propellants and gas generators, and to a process for curing associated energetic urethane systems. This invention also relates specifically to an azide diisocyanate curative having specific application to the curing of such energetic urethane systems.
2. Description of Related Art In the manufacture of solid fuel propellants, including rocket propellants and gas generators, a polymeric substance such as glycidyl azide polymer (GAP) is frequently employed as a binder to hold together fuel, oxidizer, and other compounds making up the propellant or gas generator. A GAP energetic binder is described in U.S. Patent 4,268,450 to Frankel et al., disclosure of which is hereby incorporated by reference.
Gas generators, such as gun propellants, may incorporate binders of nitrocellulose plasticized with GAP, such as disclosed in U.S. Patent 4,288,262 to Flanagan et al., hereby incorporated by reference.
m~zr 88R066 The addition of curing agents to such prepclymer systems causes cross-linking between the functional groups of the prepolymer, such as glyrerol-initiated GAP prepolymer, resulting in a polymer. The polymer's physical properties vary with the degree of cross-linkage. This degree can be varied by the amount and type of curing agent added. In general, it is desired to cure the prepolymers to a degree such that the resulting polymer has the physical properties of an elastomer.
Examples of known curing agents are isophorone diisocyanate, 3-nitraza-l,5-pentane diisocyanate, and the biuret trimer of hexamethylene dilsocyanate (N-100), a polyfunctional isocyanate produced commercially by Mobay Chemical Company.
It is usually desired to suspend other compounds in the polymer binder composition. For instance, a solid rocket propellant composition could comprise such a polymer in which is blended a plasticizer, an oxidizer, and a fuel.
Examples of suitable fuels would be light metals and light metal hydrides. Examples of suitable ozidizers would be perchlorates and nitrates.
SUMMARY OF THE INVENTION Accordingly, there is provided by the present invention a curative for curing energetic urethane systems, a method for producing said energetic curative, and a process for utilizing said energetic curative in curing energetic urethane systems.
mn.
88R066 OBJECTS OF THE INVENTION It is, therefore, an object of this invention to provide a method for curing energetic urethane polymer systems.
it is a further object of this invention to provide a novel azide diisocyanate curative and a novel process for the preparation thereof.
Other objects and attendant advantages will be evident from the following description of the invention.
DESCRIPTION OF THE PREFERRED EMBODIMENTS The objects of this invention are accomplished in the synthesis of a novel energetic azide diisocyanate curative 2,2-bis (azidomethyl)-1,3-propane diisocyanate (BAMPDI).
The synthesis of the energetic azide diisocyanate BAMPDI is accomplished, according to the present invention, in a 6-step reaction sequence.
The starting material is 3,3-bis(cyanomethyl) oxetane Treatment of the starting material with aqueous hydrobromic acid S gives 3-bromo-2,2-bis(cyanomethyl)-l-propanoI which is then converted to 3-bromo-2,2-bis(cyanomethyl)-l-propyl tosylate The reaction, then, of the tosylate compound with sodium azide produces 2,2-bis(azidomethyl)-1,3-dicyanopropane This is followed by hydrolysis of the 1,3-dicyanopropane to yield 3,3bis(azidomethyl)-glutaric acid which is converted with phosphorous pentachloride to 3,3-bis(azidomethyl) glutaryl chloride -l 8F R066 The novel azido dilsocyanate curative 2,2-bis(azidomethyl)-1, 3-propane dilsocyanate (BAMPDI) is obtained by reacting the glutaryl chloride with an inorganic azide to form an intermediate di(acylazide), followed by decomposition and rearrangement to give the desired diisocyanate. The properties of BAMPDI are summarized in Table I hereinbelow.
TABLE I NAME: 2,2-BIS(AZIDOMETHYL)-l ,3-PROPANE DIISOCYANATE STRUCTURE: CH2
N
3
OCNCH
2
CCH
2
NCO
CH
2
N
3
FORMULA:
APPEARANCE:
EQUIVALENT
WEIGHT:
PURITY:
BOILING
POINT:
IMPACT
SENSITIVITY:
FRICTION
SENSITIVITY:
C
7
H
8
N
8 0 2 Yellow Mobile Liquid 125 (Theoretical =118) 94.4% 70 0 C at 0.01 mmn 200 in-lb 36 Kg cm A~ H
ELEMENTAL
ANALYSIS:
91 Kcal/mol (Est.)
CALCULATED:
C
35.59 35.06
H
3.39 3.37
N
47.46 46.84 FOUND: 88R066 A more detailed explanation of the synthesis of BAMPDI is hereinafter provided.
3-Bromo-2.2-Bis(Cyanomethyl)-l-Propanol (2) In a suitable reaction vessel, equipped with a stirrer, was admixed 9.6 grams (0.07 mole) of 3,3-bis(cyanomethyl) oxetane and milliliters of water. To this mixture was added, dropwise, in minutes, 14.6 grams of 47% hydrobromic acid (0.09 mole). The reaction mixture was stirred overnight at ambient temperature, and then refluxed for 4 hours. The organic phase was separated, dried, and concentrated to give 13.1 grams of white solid.
Elemental Analysis: Calculated for C H C, 38.73; H, 4.18; N, 12.91.
Found: C, 38.76; H, 4.47; N, 12.59.
3-Bromo-2,2-Bis(Cyanomethyl)-l-Propyl Tosylate (3) To a mixture of 12.8 grams (0.059 mole) of 3-bromo-2,2-bis (cyanomethyl)-l-propanol and 29.5 grams of pyridine, in a suitable container, was added, at from about 0° to about 5 C, a solution of 12.4 grams (0.06 mole) of p-toluenesulfonyl chloride in 15 milliliters of chloroform as a solvent. The reaction mixture was stirred at ambient temperature for about one week and quenched in 500 milliliters of water. The organic layer was separated; washed with water, dilute hydrochloric acid, and water; dried over anhydrous magnesium sulfate; and concentrated to give 17.9 grams of white solid, m.p. 86.8*C.
4 88R066 Elemental Analysis: Calculated for C4 H BrSO3 C, 45.29; H, 4.07; N, 7.55.
Found: C, 45.24; H, 4.42; N, 7.09..
2,2-Bis(Azidomethyl)-l.3-Dicyanopropane (4) A mixture of 17.9 grams (0.048 mole) of 3-bromo-2,2-bis (cyanomethyl)-l-propyl tosylate and 50 milliliters of dimethylsulfoxide was heated to 65 0 C, and 9.4 grams (0.145 mole) of sodium azide was added. The mixture was then heated at from 95" to 98°C for 22 hours and quenched in 800 milliliters of water. The aqueous phase was extracted with 3 x 25 milliliters of chloroform and washed with water to remove the dimethylsulfoxide. After drying over anhydrous magnesium sulfate, the solution was concentrated to give 6.4 grams of white solid, m.p. 68.5 0 -69.5 0
C.
Elemental Analysis: Calculated for CHBN8: C, 41.r'; H, 3.95; N, 54.88.
Found: C, 41.21; H, 4.37; N, 54.70.
3,3-Bis(Azidomethvl)-Glutaric Acid A solution of 29.6 grams (0.15 mole) of 2,2-bis(azldomethyl)-l,3-dicyanopropane, 150 milliliters of water, and 57.3 grams (0.87 mole) of 85% potassium hydroxide was refluxed for 24 hours, cooled, and acidified with concentrated hydrochloric acid. The solid product was collected, washed with water, and dried to give 23,7 grams of product, m.p. 123 0 -124 0
C.
88R066 Elemental Analysis: Calculated for C H IN604O C, 34.71; H, 4.16; N, 34.70.
Found: C, 34.41; H, 4.67; N, 35.16; 3.3-Bis(Azidomethyl) Glutaryl Chloride (6) To a mixture of 8.9 grams (0.037 mole) of 3,3-bis(azidomethyl)-glutaric acid, 15 miliiliters of dry benzene, and 0.07 grams of zinc chloride was added, portionwise, 15.4 grams (0.074 mole) of phosphorous pentachloride in 1 hour, with cooling, to maintain the reaction temperature at about 100 to about 20°C. The reaction mixture was stirred overnight at ambient temperature, filtered, and concentrated to give 10.3 grams (100%) of yellow liquid.
Elemental Analysis: Calculated for C H C12N602 C, 30.11; H, 2.87; Cl, 25.45; N, 30.11.
Found: C, 30.59; H, 3.10; Cl, 24.48; N, 29.71.
2,2-Bis(Azidomethyl)-1.3-Propane Diisocyanate (BAMPDI) A solution of 9.3 grams (0.14 mole) of sodium azide in 37 milliliters of water was cooled in an ice-bath, and a solution of grams (0.018 mole) of 3,3-bis(azidomethyl) glutaryl chloride and milliliters of ethylene dichloride was added, dropwise. This reaction mixture was stirred for 10 minutes following the addition of the second solution above. The organic phase was separated and dried over anhydrous magnesium sulfate. The solution was slowly heated to 50°C, causing the intermediate diazide to decompose, liberating nitrogen. The solution was finally heated to reflux to -7- 88R066 complete the decomposition, and concentrated to give 3.8 grams of yellow liquid.
Elemental Analysis: Calculated for C H N8 02 C, 35.59; H, 3.39; N, 47.46.
Found: C, 35.06; H, 3.37; N, 46.84.
As previously indicated, the curative of the present invention, when utilized in energetic urethane systems, will affect the pot life, the handling time available between the mixing and when the cure begins to set up, dependent upon the specific materials used, the mixing and curing temperature, and size of other components, such as fuel and the like.
Mixing of the urethane system is normally carried out at room temperature or such higher temperature as needed to provide a viscosity sufficiently low to allow thorough mixing. Depending on factors such as desired cure time, curing temperature of the system can vary. However, curing temperature is typically held within the S range of ambient room temperature to 140"F, with a preferred range of 1100 to 130 0
F.
a The process, according to the present invention, for producing an energetic urethane system, which system includes at least a binder, a plasticizer, an oxidizer, and a fuel, comprises: admixing a binder, plasticizer, oxidizer, and a fuel; introducing an azide diisocyanate curative 2,2-bis (azidomethyl)-1,3-propane diisocyanate; and 88R066 curing said energetic urethane system.
In summary, a novel azide diisocyanate curative, method of preparation, and utilization in a curing process have been developed.
Obviously, many modifications and variations of the present invention are possible in light of the above teachings. It is, therefore, to be understood that within the scope of the appended claims, the invention may be practiced other than specifically described.
What is claimed is: e

Claims (3)

  1. 2. The compound of claim I when usod as a curative r or curing enierg-etic urethane binders. 3 .1 process for curing an energectic urcthane system comiprising a binder, a urethane plasticizer, an oxidizer and a fuel, which process comprises: admixin-.g a binder, urethane plasticizer, t.0 o.-idizer and fuel; 0b) introducing an azicic diisocyanatc Curative 2 ,2-bis (azidloniethiyl)-1,3-propatiic diisocyanatc; and curing said eneirge tic uvctizne system.
  2. 4. A meothod for the preparation of 2 ,2-bis- (azidowethyl) 3-propane diisocyanato coirprising: adniixcing and reacting 3 3ois (cyanonilethyl) oxzetaneul wvith hlydro 'romic acid to orodi-in c 3-!brojInO-2 ,2-bis- (cyaniiooe hy -1-propin 01; combinling a-d rea.ctn 3-rn-2 ,-bis- (cyan-ouelitliyl).---pr-opau~o 1, pyridine, anld p)-to luecnc:3LI ily] chlorile1 to yield 3-bronwo-2,2-i(cameiy)--rol tosylate; preparing a ;Aixture of 3-bromao-2,2-b is- (cyaaiomcthyl) -1-propyl tosylate a)nd diniethylsul'fo~iclc, to which sodium. azide iq ad;.iixed for reacetion to vro~ilce 2,2-b is (azidlomot1lyl) -I .3-dinyanopropanc; re uiga solu~tion 2bs(zioe~il) I ,3-dIIicyiiopropanc a:nd potassiumn 1iycro-,,idv -1:id rod1 Iciflg prcpaiiig a rea-ction i:ur of 3, 3-is- (azclonetril -gutaic cid~ :e~u ,Zinlc c'hloride a)(d pho spaorous p e-itaclilo ride andl rear: ti lag sid. :ai.%turc to prepare 3 ,3-his (azidjoinoathyl) gintaryl chloride; and coi:Ci'-ining 3,3-big (azidono thyl) gititaryl. chlloride and et'rrlcne cdielloridc, introdlitein, thiis compositel into a solution of so-ium azide, and effecting. a reaction thecrein- oet7 ,scn to produce thec co~iinpound 2,2-his (a~zidome;Ithyl) propane di isocyanMate. :i Tile method of claim 4, wherein tilO Iydrobromdic aciJ of step is 47; Ilydrobrovnic acid, anid whore ii the reaction mixture was stirred overni ght at aubient temperature, and then ref 1u~ed for 4 hours.
  3. 6. The method of claim 4, wherein the p-toiucne- sulfonyl chloride reactant of step is in chloroform'. T. ihp method of claim 4, wherein in1 stop the reaction mivture of 3-broio-?, 2-bis (cyanomctihyl) propyI tosylate, cdimthylsulfoxcide and sodium azido is hoated from 050C to 0800 for 22 hours, follownd by quenching in. water. S. Tho ;-iic thod of c]ai-i 41, wr'i i s tep tile 50 lution of 2 ,2-bis (azidomethyl)- 1.,3-dicynopropanc and potassiumi hydroxide wis ref lu-ced for 24 3iourS Coo0l00 and L'icn acidified with a ;iinoral acid. Tae muethod. of claim S, w'vriin the mineral qcid is concentrated hycdrop~hl]orin "cid. rothiod to produce 2,2-bis (azidomethyl) -t I propane diisocnyanutoc omprisinS combining ,3is(aio methyl) gin taryl chloride and ethylene dichloride, introducing this composite into a solution of sodium azido, ra effecting a reaction tliercinbctween to produce the compound 2 ,2-bis (azidomethyl) -1 ,3-propane dilsocyanate, via:1 an unisolated intermediate di(acyl-azide). Qi. Tile method of claiT~ 10, wherein an illturmediab(- (liaeyla;i1) was caused to decompoqo by slowly heating tihe reactant solution to .500C. DATEZ) this THIRTY FIRST day of MA-%RCiI 1994 Rtockwell International Corporation Patent \ttorneys for the Applicant MPUSON FERGUS ON -11- 88R066 Abstract A process for curing an energetic urethane system with the curative 2,2-bis(azidomethyl)-1,3-propane dlisocyanate, and method for producing said curative. 0384m
AU82522/91A 1990-08-06 1991-08-05 Energetic urethane system curative Ceased AU653317B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US56297290A 1990-08-06 1990-08-06
US562972 1990-08-06
FR9110999A FR2706890A1 (en) 1990-08-06 1991-09-05 1,3-Diisocyanato-2,2-bis(azidomethyl)propane and its intermediates and application to the vulcanisation of a system containing energising (energy-providing) urethanes

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU60596/94A Division AU6059694A (en) 1990-08-06 1994-04-19 Energetic urethane system curative

Publications (1)

Publication Number Publication Date
AU653317B1 true AU653317B1 (en) 1994-09-29

Family

ID=26228934

Family Applications (1)

Application Number Title Priority Date Filing Date
AU82522/91A Ceased AU653317B1 (en) 1990-08-06 1991-08-05 Energetic urethane system curative

Country Status (3)

Country Link
AU (1) AU653317B1 (en)
FR (1) FR2706890A1 (en)
GB (2) GB2280902B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2009039A1 (en) 2007-06-27 2008-12-31 Universiteit Gent Functionalised polyurethanes

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4288262A (en) * 1978-03-30 1981-09-08 Rockwell International Corporation Gun propellants containing polyglycidyl azide polymer
US4707199A (en) * 1983-10-17 1987-11-17 The United States Of America As Represented By The Secretary Of The Army Non nitroglycerin-containing composite-modified double-base propellant
CA1305164C (en) * 1987-06-22 1992-07-14 Milton B. Frankel Energetic azido curing agents

Also Published As

Publication number Publication date
GB9215603D0 (en) 1994-10-26
GB2280903A (en) 1995-02-15
GB9116295D0 (en) 1994-10-26
FR2706890A1 (en) 1994-12-30
GB2280902A (en) 1995-02-15
GB2280903B (en) 1995-06-28
GB2280902B (en) 1995-06-28

Similar Documents

Publication Publication Date Title
JP3781432B2 (en) Highly functionalized polyurethane
EP0180783B1 (en) Polymerization of bicyclic amide acetals and polyisocyanates in the presence of moisture
US3573259A (en) Process for the preparation of isocyanurate-containing polyisocyanate salts
US3839354A (en) Diisocyanate hydantoin compounds
AU653317B1 (en) Energetic urethane system curative
GB2029413A (en) Preparation of organic mono- and polyisocyanates
JP2548750B2 (en) Epoxidized isocyanates and method for producing the same
US4962213A (en) Energetic azido curing agents
JPS63183553A (en) Preparation of cyclohexylmono- and -urethane by adding methylcarbamate to limonene, isocyanate derived therefrom, method and composition
CA1197941A (en) Powder coating composition
US2797232A (en) Hidden polyisocyanates
JPH04505159A (en) New cyclic polyiminoether
US3939200A (en) Aliphatic acyl-containing amine hydrochlorides
US6479614B1 (en) Energetic copolyurethane thermoplastic elastomers
US3652599A (en) Novel azidosulfonylcarbanilates
US4100348A (en) Triols containing hydantoin rings
Fedoseev et al. Synthesis and properties of blocked Di-and polyisocyanates
JPS58128392A (en) Novel diisocyanate and manufacture
US4567287A (en) Preparation of carbamates from organic carbonates and aromatic ureas
JPS6315264B2 (en)
US2855420A (en) Isocyanates and process of preparing same
AU605314B2 (en) Energetic azido curing agents
JP3163532B2 (en) Aromatic diisocyanate
US4448816A (en) Compounds, compositions and process
US3639341A (en) Linear polyurethane resin