WO1999055766B1 - Novel polymer additives for forming objects - Google Patents
Novel polymer additives for forming objectsInfo
- Publication number
- WO1999055766B1 WO1999055766B1 PCT/US1999/009327 US9909327W WO9955766B1 WO 1999055766 B1 WO1999055766 B1 WO 1999055766B1 US 9909327 W US9909327 W US 9909327W WO 9955766 B1 WO9955766 B1 WO 9955766B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- prepolymer composition
- polyester resin
- polymer
- ethylene glycol
- prepolymer
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims 29
- 239000000654 additive Substances 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 92
- 239000000945 filler Substances 0.000 claims abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 52
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 37
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 34
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 28
- 239000004645 polyester resin Substances 0.000 claims 26
- 229920001225 polyester resin Polymers 0.000 claims 26
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims 24
- 229920001223 polyethylene glycol Polymers 0.000 claims 24
- 239000002202 Polyethylene glycol Substances 0.000 claims 22
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims 20
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 18
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims 17
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 claims 17
- 229940093476 ethylene glycol Drugs 0.000 claims 16
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 15
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 10
- 239000001530 fumaric acid Substances 0.000 claims 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 9
- 239000004342 Benzoyl peroxide Substances 0.000 claims 7
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 7
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 7
- 239000000843 powder Substances 0.000 claims 7
- UAXOELSVPTZZQG-UHFFFAOYSA-N trimethyl acrylic acid Chemical compound CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 claims 7
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 6
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 6
- 229920000728 polyester Polymers 0.000 claims 6
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims 5
- 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 claims 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 4
- 239000001768 carboxy methyl cellulose Substances 0.000 claims 4
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 4
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 4
- 239000000463 material Substances 0.000 claims 4
- 150000002978 peroxides Chemical class 0.000 claims 4
- 239000004814 polyurethane Substances 0.000 claims 4
- 229920002635 polyurethane Polymers 0.000 claims 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 4
- 229940068984 polyvinyl alcohol Drugs 0.000 claims 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims 3
- 239000004641 Diallyl-phthalate Substances 0.000 claims 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 3
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims 3
- 239000004359 castor oil Substances 0.000 claims 3
- 235000019438 castor oil Nutrition 0.000 claims 3
- 239000003822 epoxy resin Substances 0.000 claims 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims 3
- 239000000944 linseed oil Substances 0.000 claims 3
- 235000021388 linseed oil Nutrition 0.000 claims 3
- 229920000647 polyepoxide Polymers 0.000 claims 3
- 239000004576 sand Substances 0.000 claims 3
- 239000004094 surface-active agent Substances 0.000 claims 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 claims 2
- -1 ANTAROX 25-R2 Substances 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 2
- 239000004793 Polystyrene Substances 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims 2
- 229910021538 borax Inorganic materials 0.000 claims 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims 2
- 239000000292 calcium oxide Substances 0.000 claims 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000000835 fiber Substances 0.000 claims 2
- 239000011152 fibreglass Substances 0.000 claims 2
- 239000010440 gypsum Substances 0.000 claims 2
- 229910052602 gypsum Inorganic materials 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 239000003921 oil Substances 0.000 claims 2
- 235000019198 oils Nutrition 0.000 claims 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 2
- 229920000767 polyaniline Polymers 0.000 claims 2
- 239000004926 polymethyl methacrylate Substances 0.000 claims 2
- 229920002223 polystyrene Polymers 0.000 claims 2
- 239000004328 sodium tetraborate Substances 0.000 claims 2
- 235000010339 sodium tetraborate Nutrition 0.000 claims 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims 1
- 101000581122 Homo sapiens Rho-related GTP-binding protein RhoD Proteins 0.000 claims 1
- 239000000026 Pentaerythritol tetranitrate Substances 0.000 claims 1
- 102100027609 Rho-related GTP-binding protein RhoD Human genes 0.000 claims 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- YLPZVNXGKBIJBW-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride;dihydrate Chemical compound O.O.[Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 YLPZVNXGKBIJBW-UHFFFAOYSA-M 0.000 claims 1
- 125000004386 diacrylate group Chemical group 0.000 claims 1
- 239000012975 dibutyltin dilaurate Substances 0.000 claims 1
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 claims 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims 1
- 229960002598 fumaric acid Drugs 0.000 claims 1
- 230000008774 maternal effect Effects 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract 3
- 239000011347 resin Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 238000005336 cracking Methods 0.000 abstract 1
- 230000001788 irregular Effects 0.000 abstract 1
- 239000003562 lightweight material Substances 0.000 abstract 1
- 239000002986 polymer concrete Substances 0.000 abstract 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/68—Unsaturated polyesters
- C08G18/683—Unsaturated polyesters containing cyclic groups
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/02—Macromolecular compounds
- C04B26/10—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C04B26/16—Polyurethanes
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
- C04B2111/20—Resistance against chemical, physical or biological attack
- C04B2111/28—Fire resistance, i.e. materials resistant to accidental fires or high temperatures
Abstract
The present invention relates to novel methods and compositions related to polymer concrete comprising conventional resins with novel additives to prevent shrinking and cracking of the resin, to accelerate curing and to treat fillers. These compositions and methods can be employed to form large objects and objects of irregular shapes. These compositions and methods provide lightweight materials some of which are hard and inflexible, while others are hard and flexible.
Claims
1. A composition comprising: at least one oil; dibutyltin dilaurate; at least one molecular sieve; at least one filler maternal: and at least one surfactant selected from ANTAROX 25-R2 and RHOD AFAC RS-710.
2. The composition of Claim 1, wherein the at least one oil comprises castor oil, linseed oil, or a combination thereof.
3. The composition of Claim 1, wherein the at least one filler material comprises calcium carbonate, sand, or a combination thereof.
4. The composition of Claim 1, further comprising diphenylmethane diisocyanate.
5. The composition of Claim 1, wherein the surfactant compnses ANTAROX 25-R2.
6. The composition of Claim 1, further comprising propylene glycol, fumaric acid, maleic anhydride, and phthalic anhydride.
7. A polyurethane polymer produced from the composition of any one of Claims 1-6.
8. The polyurethane polymer of Claim 7, wherein the composition comprises castor oil, linseed oil, ANTAROX 25-R2, calcium carbonate, sand, and 4,4 '-diphenylmethane diisocyanate.
9. The polyurethane polymer of Claim 8, further compnsing propylene glycol, fumaric acid, maleic anhydride, and phthalic anhydride.
97
10. The polyurethane polymer of Claim 7, wherein the composition comprises castor oil, linseed oil, RHODAFAC RS-710, calcium carbonate, sand, and 4,4'-diphenylmethane diisocyanate.
11. A prepolymer composition comprising a solution that is capable of undergoing polymerization and is substantially non-flammable.
12. The prepolymer composition of Claim 11, wherein the prepolymer composition has a flash point of greater than approximately 150°F.
13. The prepolymer composition of Claim 11, wherein the prepolymer composition has a flash point of greater than approximately 190°F.
14. The prepolymer composition of Claim 11, wherein the prepolymer composition has a flash point of greater than approximately 212°F.
15. The prepolymer composition of Claim 11, wherein the prepolymer solution is polymerized to form a solid object.
16. The prepolymer composition of Claim 11, wherein the composition comprises: polyethylene glycol; and polyester resin.
17. The prepolymer composition of Claim 16, further comprising: ethylene glycol; and maleic anhydride.
18. The prepolymer composition of Claim 17, further comprising: polystyrene; and ethylenediamine.
19. The prepolymer composition of Claim 17, further comprising styrene.
98
20. The prepolymer composition of Claim 19, further comprising ethylenediamine.
21. The prepolymer composition of Claim 16, further comprising ethylene dimethacrylate.
22. The prepolymer composition of Claim 16 or 17, further comprising at least one of ethylene dimethacrylate (EDM), polyvinyl alcohol, an epoxy resin, borax, carboxymethyl cellulose (CMC), ethylene glycol dimethacrylate (EGD), polyethylene glycol dimethacrylate (PEGDAM), ethylene glycol, diethylene glycol (DEG), fumaric acid, pentaerythritol tetraacrylate (PENT A), and a peroxide.
23. The prepolymer composition of Claim 16, further comprising:
N,N-dimethyI aniline; a catalyst; and at least one peroxide.
24. The prepolymer composition of Claim 23, wherein the catalyst comprises cobalt naphthenate.
25. The prepolymer composition of Claim 23, wherein the at least one peroxide comprises methyl ethyl ketone peroxide, hydrogen peroxide, benzoyl peroxide or a combination thereof.
26. The prepolymer composition of any one of Claims 11-25, further comprising at least one filler material.
27. The prepolymer composition of Claim 26, wherein the at least one filler material comprises calcium carbonate, calcium oxide, gypsum, or a combination thereof.
28. A polymer produced from the prepolymer composition of any one of Claims 11 -27.
99
29. The polymer of Claim 28, wherein the prepolymer composition comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; polystyrene; ethylenediamine; calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
30. The polymer of Claim 28, wherein the prepolymer composition comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; styrene; ethylenediamine; calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
1. The polymer of Claim 28, wherein the prepolymer composition comprises polyethylene glycol; polyester resin powder; and ethylene dimethacrylate (EDM).
32. The polymer of Claim 31, wherein the prepolymer composition further comprises ethylene glycol and maleic anhydride.
33. The polymer of Claim 31 or 32, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
34. The polymer of Claim 31 or 32, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; benzoyl peroxide; and gypsum.
35. The polymer of Claim 32, wherein the prepolymer composition further comprises poly vinyl alcohol and at least one of N,N-dimethyl aniline and borax.
36. The polymer of Claim 28, wherein the prepolymer composition further comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; polyvinyl alcohol; and carboxymethyl cellulose.
100
37. The polymer of Claim 28, wherein the prepolymer composition further comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; and polyethylene glycol dimethylmethacrylate (PEGDAM).
38. The polymer of Claim 37, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; and at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA).
39. The polymer of Claim 28, wherein the prepolymer composition further comprises ethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; and diethylene glycol.
40. The polymer of Claim 39, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; and at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA).
41. The polymer of Claim 28, wherein the prepolymer composition further comprises polyethylene glycol; maleic anhydride; polyethylene glycol; polyester resin powder; and polyethylene glycol dimethylmethacrylate (PEGDAM).
42. The polymer of Claim 41, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; and at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA).
43. A prepolymer composition comprising: at least one glycol selected from ethylene glycol and propylene glycol; fumaric acid; and an epoxy resin or at least one anhydride selected from maleic anhydride and phthalic anhydride.
101
44. The prepolymer composition of Claim 43, further comprising at least one of styrene and 2-hydroxymethylmethacrylate (HEMA).
45. The prepolymer composition of Claim 43 or 44, further comprising at least one of: polyethylene glycol; polyethylene glycol dimethylmethacrylate (PEGDAM); ethylene glycol dimethacrylate (EGD); pentaerythritol tetraacrylate (PENTA); tetra(ethylene glycol); tetra(ethylene glycol) dimethylacrylace; 4,4'-diaminodiphenyl methane; a polyester resin; carboxymethyl cellulose (CMC); polymethyl methacrylate; methyl methacrylate; ethylene glycol; diethylene glycol; diallyl phthalate; a surfactant; and a filler material.
46. The prepolymer composition of Claim 45, further comprising at least one of cobalt naphthenate, 1-vinyl 2-pyrrolidinone, N',N-dimethyl aniline, aluminum trihydride, and a peroxide.
47. The prepolymer composition of Claim 46, further comprising at least one of (a) acrylic acid, or (b) methacrylic acid.
48. The prepolymer composition of Claim 47, further comprising ethyl acrylate.
49. The prepolymer composition of Claim 48, further comprising: polyaniline; polyvinylalcohol; sulfuric acid; ethylene glycol; and CUCIO .
50. The prepolymer composition of Claim 49, further comprising tetra(ethyleneglycol) dimethylacrylate, tetra(ethy)eneglycol) or pentaerythritol tetraacrylate.
102
51. The prepolymer composition of Claim 47, further comprising: bisphenol A; benzyldimethyltetradecylammonium chloride dihydrate; and monohydroxyhydroquinon.
52. The prepolymer composition of Claim 47, further comprising carboxymethyl cellulose.
53. The prepolymer composition of Claim 47, further comprising at least one of 4,4-diphenylmethane diisocyanate and N, N-dimethylaniline.
54. A high flash point polyester resin produced from the prepolymer composition of any one of Claims 43-53.
55. The high flash point polyester resin of Claim 54, wherein the prepolymer composition comprises ethylene glycol, fumaric acid, maleic anhydride, and polyethylene glycol dimethylmethacrylate (PEGDAM).
56. The polymer of Claim 55, wherein the prepolymer composition further comprises calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; and at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA).
57. The polymer of Claim 55, wherein the prepolymer composition further comprises N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; hydrogen peroxide; at least one of ethylene glycol dimethacrylate (EGD) and pentaerythritol tetraacrylate (PENTA); and at least one of calcium oxide and calcium carbonate.
58. The high flash point polyester resin of Claim 54, wherein the prepolymer composition comprises ethylene glycol, fumaric acid, ethylene glycol dimethacrylate (EGD), and pentaerythritol tetraacrylate (PENTA).
59. The polymer of Claim 58, wherein the prepolymer composition further comprises at least one of an epoxy resin; polyethylene glycol; carboxymethyl cellulose; polymethyl methacrylate; methyl methacrylate; calcium carbonate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
60. The polymer of Claim 58, wherein the prepolymer composition further comprises at least one of polyethylene glycol dimethylmethacrylate (PEGDAM); 4,4'-diaminodiphenyl methane; benzoyl peroxide; polyethylene glycol; and tetraethylene glycol (TEG).
61. The high flash point polyester resin of Claim 54, wherein the prepolymer composition comprises propylene glycol, fumaric acid, maleic anhydride, phthalic anhydride, and at least one of styrene and 2- hydroxyethylmethacrylate (HEMA).
62. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises 4,4'-diaminodiρhenyl methane; benzoyl peroxide; polyethylene glycol; and at least one of ethylene glycol dimethacrylate (EGD); diallyl phthalate; and diethylene glycol.
63. The high flash point polyester resin of Claim 62, wherein the prepolymer composition further comprises at least one of ethylene glycol; polyethylene glycol dimethylmethacrylate (PEGDAM); pentaerythritol tetraacrylate (PENTA); and dodecylbenzenesulfonic acid.
64. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises diallyl phthalate and polyethylene glycol
65. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises polyethylene glycol dimethylmethacrylate (PEGDAM); tetra(ethylene glycol) dimethyl aery late; 4,4'- diaminodiphenyl methane; and benzoyl peroxide.
104
66. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises 1-vinyl 2-pyrrolidinone; ethyl acrylate; and at least one of acrylic acid and methacrylic acid.
67. The high flash point polyester resin of Claim 66, wherein the prepolymer composition further comprises tetra(efhylene glycol) dimethylacrylate or teιra(ethylene glycol) diacrylate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
68. The high flash point polyester resin of Claim 66, wherein the prepolymer composition further comprises pentaerythritol tetraacrylate (PENTA); N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
69. The high flash point polyester resin of Claim 68, wherein the prepolymer composition further comprises polyaniline; N-methyl-pyrrolidinone; polyviπylalcohol; sulfuric acid; ethylene glycol; and CuC104.
70. The high flash point polyester resin of Claim 61, wherein the prepolymer composition further comprises bisphenol A; benzyldimemyltetradecylarnmonium chloride dihydrate; monohydroxyhydroquinon; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
71. The high flash point polyester resin of Claim 66, wherein the prepolymer composition further comprises carboxymethyl cellulose; N,N- dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
72. The high flash point polyester resin of Claim 66, wherein the prepolymer composition further comprises 4,4'-diphenylmethane diisocyanate; N,N-dimethyl aniline; cobalt naphthenate; methyl ethyl ketone peroxide; and hydrogen peroxide.
105
73. A fast cure polyester/concrete mixture comprising a polyester resin; Sakrete concrete mix; styrene; N,N-dimethyl aniline; and cobalt naphthenate.
74. The polyester/concrete mixture of Claim 73, further comprising methyl methacrylate; and at least one of methyl ethyl ketone peroxide, hydrogen peroxide, and benzoyl peroxide.
75. The polyester/concrete mixture of Claim 74, further comprising propylene glycol, fumaric acid, maleic anhydride, phthalic anhydride, chopped fiberglass fibers; and 2-hydroxyethylmethacrylate (HEMA).
76. The polyester/concrete mixture of Claim 73, further comprising methyl ethyl ketone peroxide, hydrogen peroxide, and benzoyl peroxide.
77. The polyester/concrete mixture of Claim 76, further comprising propylene glycol, fumaric acid, maleic anhydride, phthalic anhydride, chopped fiberglass fibers; and 2-hydroxyethylmethacrylate (HEMA).
78. The polyester/concrete mixture of Claim 73, wherein the polyester resin comprises the polymer of Claim 28 or 54.
106
STATEMENT UNDER ARTICLE 19
The amendments to claims 1, 4-6, 8-10, 12, 18, 21-25 and 32, and new claims 7-10, 26-42, and 54-78 more particularly set forth the inventive aspect of the prepolymer compositions, polymers formed the prepolymer compositions, and polymer/concrete mixtures. More specifically, the above amendments (1) specify components of the prepolymer compositions, (2) specify components of the polymers formed from the prepolymer compositions, (3) specify components of the polymer/concrete mixtures, (4) correct misspelled words in the claims, and (5) correct errors in the original claims. The most obvious error, which has now been corrected, is the change of "°C" to "T" for the flash point temperature of the prepolymer composition of claims 12-14.
The amendments to claims 1, 4-6, 8-10, 12, 18, 21-25 and 32 are supported throughout the specification and the original claims. In particular, the amendments to claims 1 , 4-6, 8-10, 12, 18, 21-25 and 32 are supported in Examples 33-124 and original claims 1-51.
New claims 7-10, 26-42, and 54-78 are supported throughout the specification. In particular, the new claims 7-10, 26-42, and 54-78 are supported in Examples 33-133.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002333228A CA2333228A1 (en) | 1998-04-29 | 1999-04-29 | Novel polymer additives for forming objects |
| AU35737/99A AU3573799A (en) | 1998-04-29 | 1999-04-29 | Novel polymer additives for forming objects |
| EP99917670A EP1080128A1 (en) | 1998-04-29 | 1999-04-29 | Novel polymer additives for forming objects |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/069,558 | 1998-04-29 | ||
| US09/069,558 US6146556A (en) | 1998-04-29 | 1998-04-29 | Polymer additives for forming objects |
| US20961598A | 1998-12-11 | 1998-12-11 | |
| US09/209,615 | 1998-12-11 | ||
| US12253699P | 1999-03-02 | 1999-03-02 | |
| US60/122,536 | 1999-03-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1999055766A1 WO1999055766A1 (en) | 1999-11-04 |
| WO1999055766B1 true WO1999055766B1 (en) | 1999-12-09 |
Family
ID=27371565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1999/009327 WO1999055766A1 (en) | 1998-04-29 | 1999-04-29 | Novel polymer additives for forming objects |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1080128A1 (en) |
| AU (1) | AU3573799A (en) |
| CA (1) | CA2333228A1 (en) |
| WO (1) | WO1999055766A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8814861B2 (en) | 2005-05-12 | 2014-08-26 | Innovatech, Llc | Electrosurgical electrode and method of manufacturing same |
| MX2017003751A (en) | 2014-09-24 | 2017-06-28 | Chemours Co Tt Llc | Materials with enhanced protection of light sensitive entities. |
| CN109851746A (en) * | 2018-12-24 | 2019-06-07 | 山东一诺威聚氨酯股份有限公司 | Cellulose modified TPU film material and preparation method thereof |
| CN110433742B (en) * | 2019-09-11 | 2022-03-01 | 成都工业学院 | Preparation method of microcapsule with double-layer coating structure and microcapsule prepared by preparation method |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3884980A (en) * | 1970-04-06 | 1975-05-20 | Cincinnati Milacron Chem | Aldol condensation using cobalt II halide hydrazine complexes |
| US3895149A (en) * | 1973-07-05 | 1975-07-15 | Atlantic Richfield Co | Carpet backed with thixotropic polyurethane adhesive |
| CA1029494A (en) * | 1973-07-27 | 1978-04-11 | Fritz Ehrhard | Shaped polyurethane articles and a method for making them |
| US4013614A (en) * | 1975-01-29 | 1977-03-22 | H. H. Robertson Company | Method of preparing shaped articles from polymerizable compositions |
| JPS6138662A (en) * | 1984-07-30 | 1986-02-24 | Toyoda Gosei Co Ltd | Process for curing urethane coating film |
| US4691045A (en) * | 1984-12-06 | 1987-09-01 | Nippon Shokubai Kagaku Co., Ltd. | Hydroxyl group-containing (meth)acrylate oligomer, prepolymer therefrom, and method for use thereof |
| US4822849A (en) * | 1987-08-03 | 1989-04-18 | Reichhold Chemicals, Inc. | Low shrink hybrid resins |
| US5284705A (en) * | 1990-09-06 | 1994-02-08 | Garland Floor Co. | Antistatic coating comprising tin-oxide-rich pigments and process and coated substrate |
-
1999
- 1999-04-29 AU AU35737/99A patent/AU3573799A/en not_active Abandoned
- 1999-04-29 CA CA002333228A patent/CA2333228A1/en not_active Abandoned
- 1999-04-29 EP EP99917670A patent/EP1080128A1/en not_active Withdrawn
- 1999-04-29 WO PCT/US1999/009327 patent/WO1999055766A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU3573799A (en) | 1999-11-16 |
| CA2333228A1 (en) | 1999-11-04 |
| WO1999055766A1 (en) | 1999-11-04 |
| EP1080128A1 (en) | 2001-03-07 |
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