Dihydroxy lactam based polymers, compositions and applications thereof

Patent metadata

Field	Value
Publication number	US-2022315761-A1
Application number	US-202017425527-A
Country	US
Kind code	A1
Filing date	Jan 23, 2020
Priority date	Jan 25, 2019
Publication date	Oct 6, 2022
Grant date	—

Abstract

A lactam-functionalized polymer is disclosed. The dihydroxy lactam based polymer includes polyesters, polycarbonates, polyethers, poly (ester ethers), poly (ester amides), poly imides, polyamides, poly acrylates and poly (ester imides), and polyurethanes. The applications of the dihydroxy lactam based polymers are also disclosed.

First claim

1 . A polymer obtained from a reaction mixture comprising:
(i) at least one dihydroxy lactam moiety; and (ii) at least one functional moiety having a hydroxyl-reactive functional group;
wherein (i) and (ii) are independently present in amounts of about 0.01 mole % to about 99.99 moles % and the polymer is selected from a group consisting of polyester, polycarbonate, polyether, poly (ester ether), poly (ester amide), poly imide, polyamide, poly acrylates and poly (ester imide); or wherein each (i) and (ii) is present in amounts of other than 50 mole % and wherein the polymer is a polyurethane.

2 . The polymer according to claim 1 , wherein said dihydroxy lactam moiety has a structure:

wherein “R” is independently selected from the group consisting of hydrogen, and functionalized and unfunctionalized alkyl, cycloalkyl, alkenyl, and aryl groups, wherein any of the afore mentioned groups can be with or without heteroatoms and linear or branched;
“A” is an alkylene or alkenylene group comprising 2 to 50 carbon atoms; and
wherein 2 to 4 carbon atoms reside in the lactam ring between the

group and the

group;
“n” is an integer ranging from 1 to 6; and “m” is an integer ranging from 0 to 6.

3 . The polymer according to claim 2 , wherein said dihydroxy lactam moiety is selected from the group comprising of:

wherein “n” is an integer ranging from 1 to 6; and “m” is an integer ranging from 0 to 6.

4 . The polymer according to claim 3 , wherein said dihydroxy lactam moiety is selected from the group consisting of N-(2,3-dihydroxypropyl)-2-pyrrolidone, 1-[2-(2,3-dihydroxypropyloxy)ethyl]-2-pyrrolidone, and a combination thereof.

5 . The polymer according to claim 1 , wherein the functional moiety is selected from the group consisting of: (a) carbamates, (b) acyl halides, (c) sulfonyl halides, (d) isothiocyanates, (e) cyanoacrylates, (f) isocyanates, (g) oxiranes, (h) imines, (i) thiocarbonates, (j) thiols, (k) aldehydes, (l) aziridines, (m) acids and their anhydrides, (n) azides, (o) phosphorus halides with alcohols, (p) esters, (q) amines, (r) alkyl halides, (s) dihalogenomethanes and combinations thereof.

6 . The polymer according to claim 1 , wherein said functional moiety is selected from the group consisting of:
(a) hydroxyethyl carbamate, hydroxypropyl carbamate, hydroxybutyl carbamate and combinations thereof; (b) acryloyl chloride, succinyl chloride, methacryloyl chloride, crotonoyl chloride, benzoyl chloride, cinnamoyl chloride, hydrocin namoyl chloride, acetyl chloride, 2-acetoxyacetyl chloride, diphenylacetyl chloride, 2-methoxybenzoyl chloride, 3,4,5 trimethoxybenzoyl chloride, 3,4 (methylenedioxy)benzoyl chloride, cyclopropanecarbonyl chloride, pentadecenoyl chloride, 2-cyclohexene-1-carbonyl chloride, 2-thiopheneacetyl chloride and combinations thereof, (c) methane sulfonyl chloride, benzenesulfonyl chloride and combinations thereof, (d) methyl isothiocyanate, allyl isothiocyanate, aryl isothiocyanates and combinations thereof, (e) ethyl cyanoacrylate, N-butyl-cyanoacrylate (NBCA), 2-ocytyl-cyanoacrylate (2-OCA) and combinations thereof; (f) hexamethylene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), m-phenylene diisocyanate, p-phenylene diisocyanate, bitolylene diisocyanate, cyclohexane diisocyanate (CHDI), bis-(isocyanatomethyl) cyclohexane (H6XDI), dicyclohexylmethane diisocyanate (H12MDI), dimer acid diisocyanate (DDI), trimethyl hexamethylene diisocyanate, lysine diisocyanate and its methyl ester, isophorone diisocyanate, methyl cyclohexane diisocyanate, 1,5-napthalene diisocyanate, xylylene and xylene diisocyanate and methyl derivatives, polymethylene polyphenyl isocyanates, chlorophenylene-2,4-diisocyanate, polyphenylene diisocyanate, isophorone diisocyanate (IPDI), hydrogenated methylene diphenyl isocyanate (HMDI), tetramethyl xylene diisocyanate (TMXDI), hexamethylene diisocyanate (HDI), and their respective dimers, trimers and oligomers; (g) ethylene oxide (EO), propylene oxide (PO), butylene oxide, 1-octene oxide, cyclohexene oxide, styrene oxide, bisphenol A diglycidyl ether, diglycidyl ether, epichlorohydrin, glycidic acid, allyl glycidyl ether ([(2-propenyloxy)methyl]-oxirane), glycidyl (meth)acrylate, vinylcyclohexene diepoxide, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate, 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexane carboxylate, dipentene dioxide, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane meta-dioxane, and combinations thereof; (h) polyaldimines, hydroxyaldimines, polyketimines, hydroxyketimines, and combination thereof, (i) bis-(phenylthiocarbonyloxymethyl) esters, bis-(isopropylthiocarbonyloxymethyl) esters, and combinations thereof, (j) glutathione, 3-acetyl-thiol propionic acid, thio anhydride, thio acid, and combinations thereof, (k) acetaldehyde diethyl acetyl, propionaldehyde diethyl acetyl, di(acetaldehyde diethylacetal), chloroacetaldehyde diethyl acetal, and combinations thereof; (l) 2,2-bis-hydroxymethylbutanol tris-[3-(1-aziridinyl)propionate], bis-N-aziridinomethane, and combinations thereof, (m) maleic acid, maleic anhydride, fumaric acid, citric acid, alkenylsuccinic anhydrides, phthalic anhydride, terephthalic acid, succinic anhydride, tetrahydrophthalic anhydride, maleic anhydride copolymers, and combinations thereof, (n) azide-functionalized DNA, azide-functionalized peptides, azide-functionalized proteins, azide-functionalized sugars, azide-functionalized metal, azide-functionalized nanoparticles, azide-functionalized antimicrobials, isodium 4,4′-diazidostilbene-2,2′-disulfonate, aromatic bisazide compound, calcium azide, 4,4-diphenyldisulfonyl azide and p-toluenesulfonyl azide, and combinations thereof; (o) phosphorus oxychloride, phosphorus oxybromide, and combinations thereof, (p) dimethyl itaconate, di-n-butyl itaconate, vinyl hexanoate, glycolide, ε-caprolactone, γ-caprolactone, poly(D,L-lactide), poly(D-lactide), poly (L-lactide), poly(ε-caprolactone), poly (γ-caprolactone), polyglycolide, valerolactone, butralactone, polyether-polyester, poly-anhydride-diol-polyester, and combinations thereof, (q) amino alcohols, methylamine, ethylamine, hexylamine, isopropylamine, isobutylamine, amylamines, cyclohexylamine, octylamine, benzylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, diphenylamine, dibenzylamine, ethylmethylamine, N-methylaniline, ethylenediamine, propylenediamine, butylenediamine, hexamethylenediamine, cyclohexylenediamine, piperazine, toluenediamine, isophoronediamine, N,N-dimethylaniline, N,N-dimethyl-1-naphthylamine, N,N-dimethyl-p-toluidine, N,N-diethylaniline, N,N-diallylaniline, 1-phenylpiperidine, and 4-phenylmorpholine, amino-ethoxylates, cocamine, soyamine and combinations thereof, (r) bromohexanes, bromododecane, bromohexadecane, 1-bromooctadecane and combinations thereof, and (s) dibromomethane, dichloromethane and combinations thereof.

7 . The polymer according to claim 1 , wherein the reaction mixture further comprises one or more non-lactam moiety.

8 . The polymer according to claim 7 , wherein said non-lactam moiety is selected from the group comprising of functionalized/unfunctionalized compounds of aliphatic/aromatic alcohols

Assignees

• Isp Investments Llc

Inventors

• Marie Bilal S
• Tallon Michael A
• Musa Osama M

Classifications

• C08G18/73

  acyclic · CPC title

• C08G18/758

  containing two or more cycloaliphatic rings · CPC title

• C09D175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G18/675

  Low-molecular-weight compounds · CPC title

• C08G18/3844

  containing one nitrogen atom in the ring · CPC title