CA1132140A - Liant de polyurethannes - Google Patents

Liant de polyurethannes

Info

Publication number: CA1132140A
Authority: CA; Canada
Prior art keywords: process according; structural formula; diol; caprolactone; anhydride
Prior art date: 1979-11-08
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

CA339,449A

Other languages

English (en)

Inventor

Meude Tremblay

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.)

Minister of National Defence of Canada

Original Assignee

Minister of National Defence of Canada

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.)

1979-11-08

Filing date

1979-11-08

Publication date

1982-09-21

1979-11-08 Application filed by Minister of National Defence of Canada filed Critical Minister of National Defence of Canada

1979-11-08 Priority to CA339,449A priority Critical patent/CA1132140A/fr

1980-02-25 Priority to US06/123,948 priority patent/US4415728A/en

1981-11-06 Priority to US06/318,804 priority patent/US4430131A/en

1982-03-11 Priority to CA000398183A priority patent/CA1161594A/fr

1982-09-21 Application granted granted Critical

1982-09-21 Publication of CA1132140A publication Critical patent/CA1132140A/fr

Status Expired legal-status Critical Current

Links

239000011230 binding agent Substances 0.000 title abstract description 15
239000004814 polyurethane Substances 0.000 title description 6
229920002635 polyurethane Polymers 0.000 title description 5
229920000728 polyester Polymers 0.000 claims abstract description 36
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims abstract description 14
150000002009 diols Chemical class 0.000 claims description 59
238000000034 method Methods 0.000 claims description 37
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
150000002596 lactones Chemical class 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 14
150000008064 anhydrides Chemical class 0.000 claims description 14
229920001634 Copolyester Polymers 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 13
150000002118 epoxides Chemical class 0.000 claims description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 12
DFATXMYLKPCSCX-UHFFFAOYSA-N 3-methylsuccinic anhydride Chemical compound CC1CC(=O)OC1=O DFATXMYLKPCSCX-UHFFFAOYSA-N 0.000 claims description 11
239000003426 co-catalyst Substances 0.000 claims description 10
229920000642 polymer Polymers 0.000 claims description 10
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 9
STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
229920001610 polycaprolactone Polymers 0.000 claims description 7
239000004632 polycaprolactone Substances 0.000 claims description 7
229960004063 propylene glycol Drugs 0.000 claims description 7
235000013772 propylene glycol Nutrition 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 6
CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 6
MGICRVTUCPFQQZ-UHFFFAOYSA-N 4-methyloxane-2,6-dione Chemical compound CC1CC(=O)OC(=O)C1 MGICRVTUCPFQQZ-UHFFFAOYSA-N 0.000 claims description 5
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 5
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 5
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 4
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 3
MHNVXQGFSXEDIT-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hept-1(6)-ene Chemical compound C1CCCC2=C1O2 MHNVXQGFSXEDIT-UHFFFAOYSA-N 0.000 claims description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
239000011951 cationic catalyst Substances 0.000 claims description 3
KSDIHKMNSYWRFB-UHFFFAOYSA-N chrysen-2-amine Chemical compound C1=CC=CC2=CC=C3C4=CC=C(N)C=C4C=CC3=C21 KSDIHKMNSYWRFB-UHFFFAOYSA-N 0.000 claims description 3
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
235000011037 adipic acid Nutrition 0.000 claims 1
239000001361 adipic acid Substances 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229960005082 etohexadiol Drugs 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 19
239000007787 solid Substances 0.000 abstract description 11
239000003380 propellant Substances 0.000 abstract description 10
125000005442 diisocyanate group Chemical group 0.000 abstract description 9
238000009472 formulation Methods 0.000 abstract 1
-1 polyoxypropylene Polymers 0.000 description 18
239000000047 product Substances 0.000 description 12
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 8
239000000539 dimer Substances 0.000 description 7
229920001971 elastomer Polymers 0.000 description 7
239000000178 monomer Substances 0.000 description 7
239000004449 solid propellant Substances 0.000 description 7
239000000806 elastomer Substances 0.000 description 6
229910001651 emery Inorganic materials 0.000 description 6
238000005227 gel permeation chromatography Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229920005862 polyol Polymers 0.000 description 6
150000003077 polyols Chemical class 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
150000004292 cyclic ethers Chemical class 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
239000013638 trimer Substances 0.000 description 4
GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
230000009477 glass transition Effects 0.000 description 3
239000004014 plasticizer Substances 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 2
SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 2
229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 2
150000007513 acids 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
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000003999 initiator Substances 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
238000011068 loading method Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 description 2
229920003225 polyurethane elastomer Polymers 0.000 description 2
229940116351 sebacate Drugs 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
229920001897 terpolymer Polymers 0.000 description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
150000004072 triols Chemical class 0.000 description 2
WXUAQHNMJWJLTG-VKHMYHEASA-N (S)-methylsuccinic acid Chemical compound OC(=O)[C@@H](C)CC(O)=O WXUAQHNMJWJLTG-VKHMYHEASA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
GBLPOPTXAXWWPO-UHFFFAOYSA-N 8-methylnonyl nonanoate Chemical compound CCCCCCCCC(=O)OCCCCCCCC(C)C GBLPOPTXAXWWPO-UHFFFAOYSA-N 0.000 description 1
102220566099 Antileukoproteinase_R45V_mutation Human genes 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
229920005830 Polyurethane Foam Polymers 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
HWMFMDXBCKTWAX-UHFFFAOYSA-N cyclohexene 3-methyloxolane-2,5-dione Chemical compound CC1C(=O)OC(C1)=O.C1C=CCCC1 HWMFMDXBCKTWAX-UHFFFAOYSA-N 0.000 description 1
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
WXUAQHNMJWJLTG-UHFFFAOYSA-N monomethylpersuccinic acid Natural products OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
238000002103 osmometry Methods 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000011496 polyurethane foam Substances 0.000 description 1
229940095050 propylene Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000005060 rubber Substances 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
238000005303 weighing Methods 0.000 description 1

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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)

CA339,449A 1979-11-08 1979-11-08 Liant de polyurethannes Expired CA1132140A (fr)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CA339,449A CA1132140A (fr)	1979-11-08	1979-11-08	Liant de polyurethannes
US06/123,948 US4415728A (en)	1979-11-08	1980-02-25	ε-Caprolactone co-polyesters useful for the preparation of polyurethane
US06/318,804 US4430131A (en)	1979-11-08	1981-11-06	Polyurethane binders
CA000398183A CA1161594A (fr)	1979-11-08	1982-03-11	Liants a base de polyurethane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA339,449A CA1132140A (fr)	1979-11-08	1979-11-08	Liant de polyurethannes

Publications (1)

Publication Number	Publication Date
CA1132140A true CA1132140A (fr)	1982-09-21

Family

ID=4115568

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA339,449A Expired CA1132140A (fr)	1979-11-08	1979-11-08	Liant de polyurethannes

Country Status (1)

Country	Link
CA (1)	CA1132140A (fr)

1979
- 1979-11-08 CA CA339,449A patent/CA1132140A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-09-21	MKEX	Expiry

Publication	Publication Date	Title
US4415728A (en)	1983-11-15	ε-Caprolactone co-polyesters useful for the preparation of polyurethane
US4430131A (en)	1984-02-07	Polyurethane binders
CA1062847A (fr)	1979-09-18	Charge propulsive solide contenant des liants de polyethers ou de polyesters
US3663515A (en)	1972-05-16	Process of preparation of polycaprolactone polyesters and polyurethane elastomers therefrom
US5210153A (en)	1993-05-11	Thermoplastic elastomers having alternate crystalline structure for us as high energy binders
JPH06293826A (ja)	1994-10-21	熱可塑性生分解性樹脂及びその製造方法
US5436313A (en)	1995-07-25	Process for making a polyetherester
GB2307687A (en)	1997-06-04	Fibres
EP0471489B1 (fr)	1996-06-12	Procédé amélioré de préparation de polyglycidylnitrates
US4952644A (en)	1990-08-28	Synthesis of ABA triblock polymers and An B star polymers from cyclic ethers
US3362921A (en)	1968-01-09	Novel elastomeric products obtained from prepolymer compositions
US4804424A (en)	1989-02-14	Nitrate ester-miscible polyether polymers
Kawamoto et al.	2010	Synthesis and characterization of GAP/BAMO copolymers applied at high energetic composite propellants
CA1161594A (fr)	1984-01-31	Liants a base de polyurethane
CA1132140A (fr)	1982-09-21	Liant de polyurethannes
US5099042A (en)	1992-03-24	Synthesis of tetrafunctional polyethers and compositions formed therefrom
US5162494A (en)	1992-11-10	Isotactic poly(glydicyl nitrate) and synthesis thereof
EP0021569A1 (fr)	1981-01-07	Polymères contenant des groupements amino terminaux, procédé pour leur préparation et leur utilisation
US6730181B1 (en)	2004-05-04	Process for making stable cured poly(glycidyl nitrate)
US3499058A (en)	1970-03-03	Mixture of two polyesters with pyromellitic dianhydride
US5798480A (en)	1998-08-25	High performance space motor solid propellants
Kricheldorf et al.	2001	Polymers of Carbonic Acid, 30 Ring‐Expansion Polymerization of Trimethylene Carbonate (TMC, 1, 3‐Dioxanone‐2) with Dibutyltin Succinate or Adipate
US4560779A (en)	1985-12-24	Preparation and polymerization of oxether-1
US4973658A (en)	1990-11-27	Thermoplastic copolyester elasatomer binder for oxidizer particles
US5264596A (en)	1993-11-23	Isotactic poly(glycidyl nitrate) and synthesis thereof