IP Library Granted Patent US 7,008,476
Granted Patent B2
US 7,008,476 · App. 10/459,229 · Granted Mar 7, 2006

Modified alginic acid of alginic acid derivatives and thermosetting anti-reflective compositions thereof

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Quick Facts
Patent No.
US 7,008,476
App. No.
10/459,229
Granted
Mar 7, 2006
Kind
B2
Abstract

Modified alginic acid or alginic acid derivatives and anti-reflective coatings based on thereon are described.

Claims (20)

1. Solvent soluble acetyl alginate modified with a light-absorbing compound so as to leave sufficient hydroxyl and/or carboxyl groups on the acetyl alginate for crosslinking with a crosslinking compound wherein the light absorbing compound is an aromatic oxide selected from styrene oxide, 1,2-epoxy-phenoxypropane, glycidyl-2-methylphenyl ether, (2,3-epoxypropyl)benzene, 1-phenylpropylene oxide, stilbene oxide, 2-(or 3- or 4-)halo stilbene oxide, benzyl glycidyl ether, C 1-10 straight or branched chain alkylphenyl glycidyl ether, 4-halophenyl glycidyl ether, glycidyl 4-C 1-10 straight or branched chain alkoxyphenyl ether, 2,6-dihalobenzylmethyl ether, 3,4-dibenzyloxybenzyl halide, 2-(or 4-)methoxybiphenyl, 3,3′-(or 4,4′-)diC 1-10 straight or branched chain alkoxybiphenyl, 4,4′-dimethoxyoctafluorobiphenyl, 1-(or 2-)C 1-10 straight or branched chain alkoxynaphthalene, 2-halo-6-methoxynaphthalene, 2,6-diC 1-10 straight or branched chain alkoxynaphthalene, 2,7-diC 1-10 straight or branched chain alkoxynaphthalene, 1,2,3,4,5,6-hexahalo-7-C 1-10 straight or branched chain alkoxynaphthalene, 9,10 -bis(4-C 1-10 straight or branched chain alkoxyphenyl )-anthracene, 2-C 1-10 straight or branched chain alkyl-9,10-diC 1-10 straight or branched chain alkoxyanthracene, 9,10-bis(4-C 1-10 straight or branched chain alkoxyphenyl)-2-halo-anthracene, 2,3,6,7,10,11-hexamethoxytriphenylene, glyciclyl-3-(pentadecadienyl)phenyl ether, 4-t-butylphenylglycidyl ether, triphenylolmethane triglycidyl ether, [(4-(1-heptyl-8-[3-(oxiranylmethoxy)phenyl]octyl)phenoxy)methyl]oxirane, tetraphenylolethane tetraglycidyl ether, and hydroxyphenol diglycidyl ether.

2. A composition comprising:

a) the solvent soluble acetyl alginate modified with a light-absorbing compound of claim 1 ; and

b) at least one crosslinking agent.

3. The composition of claim 2 wherein b) the crosslinking agent is selected from aminoplast, isocyanate, a compound selected from

where R 10 and R 11 are each independently optionally substituted C 1-10 alkoxy; and R 12 is hydrogen or alkyl;

wherein, R 1 and R 2 individually represent straight or branched C 1-10 alkyl, straight or branched C 1-10 ester, straight or branched C 1-10 ketone, straight or branched C 1-10 carboxylic acid, straight or branched C 1-10 acetal, straight or branched C 1-10 alkyl including at least one hydroxyl group, straight or branched C 1-10 ester including at least one hydroxyl group, straight or branched C 1-10 ketone including at least one hydroxyl group, straight or branched C 1-10 carboxylic acid including at least one hydroxyl group, and straight or branched C 1-10 acetal including at least one hydroxyl group; and R 3 represents hydrogen or methyl; R 4 represents hydrogen or methyl; and a and b individually represent the relative amounts of each comonomer and each is a positive integer greater than 0;

wherein, R 5 , R 5 and R 7 individually represent straight or branched C 1-10 alkyl, straight or branched C 1-10 ester, straight or branched C 1-10 ketone, straight or branched C 1-10 carboxylic acid, straight or branched C 1-10 acetal, straight or branched C 1-10 alkyl including at least one hydroxyl group, straight or branched C 1-10 ester including at least one hydroxyl group, straight or branched C 1-10 ketone including at least one hydroxyl group, straight or branched C 1-10 carboxylic acid including at least one hydroxyl group, and straight or branched C 1-10 acetal including at least one hydroxyl group; R 7 represents hydrogen or methyl; a is a positive integer greater than 0; and n represents a number of 1 to 5, or mixtures thereof.

4. The composition of claim 2 wherein b) the crosslinking agent is an aminoplast.

5. The composition of claim 4 wherein b) the crosslinking agent is an aminoplast selected from N,N,N,N-tetra(methoxymethyl)glycoluril, N,N,N,N-tetra(ethoxymethyl)glycoluril, N,N,N,N-tetra(n-propoxymethyl)glycoluril, N,N,N,N-tetra(i-propoxymethyl)glycoluril, N,N,N,N-tetra(n-butoxymethyl)glycoluril and N,N,N,N-tetra(t-butoxymethyl)glycoluril, methylpropyltetramethoxymethyl glycoluril, methylphenyltetramethoxymethyl glycoluril, N,N′-dimethyl urea, benzourea, dicyandiamide, formaguanamine, acetoguanamine, ammeline, 2-chloro-4,6-diamino-1,3,6-triazine, 6-methyl-2,4-diamino, 1,3,5-traizine, 3,5-diaminotriazole, triaminopyrimidine, 2-mercapto-4,6-diamino-pyrimidine, 3,4,6-tris(ethylamino)-1,3,5-triazine, tris(alkoxycarbonylamino)triazine, N,N,N,N-tetrahydroxymethylglycoluril, N,N,N′,N′-tetramethoxymethylurea and mixtures thereof.

6. The composition of claim 2 wherein b) the crosslinking agent is an isocyanate.

7. The composition of claim 2 wherein b) the crosslinking agent is a compound selected from

where R 10 and R 11 are each independently optionally substituted C 1-10 alkoxy; and R 12 is hydrogen or alkyl;

wherein, R 1 and R 2 individually represent straight or branched C 1-10 alkyl, straight or branched C 1-10 ester, straight or branched C 1-10 ketone, straight or branched C 1-10 carboxylic acid, straight or branched C 1-10 acetal, straight or branched C 1-10 alkyl including at least one hydroxyl group, straight or branched C 1-10 ester including at least one hydroxyl group, straight or branched C 1-10 ketone including at least one hydroxyl group, straight or branched C 1-10 carboxylic acid including at least one hydroxyl group, and straight or branched C 1-10 acetal including at least one hydroxyl group; and R 3 represents hydrogen or methyl; R 4 represents hydrogen or methyl; and a and b individually represent the relative amounts of each comonomer and each is a positive integer greater than 0;

wherein, R 5 , R 6 and R 7 individually represent straight or branched C 1-10 alkyl, straight or branched C 1-10 ester, straight or branched C 1-10 ketone, straight or branched C 1-10 carboxylic acid, straight or branched C 1-10 acetal, straight or branched C 1-10 alkyl including at least one hydroxyl group, straight or branched C 1-10 ester including at least one hydroxyl group, straight or branched C 1-10 ketone including at least one hydroxyl group, straight or branched C 1-10 carboxylic acid including at least one hydroxyl group, and straight or branched C 1-10 acetal including at least one hydroxyl group; R 7 represents hydrogen or methyl; a is a positive integer greater than 0; and n represents a number of 1 to 5, or mixtures thereof.

8. The composition of claim 2 further comprising one or more cross-linking catalysts.

9. The composition of claim 8 wherein the cross-linking catalyst is selected from thermal acid generators, acids, and mixtures thereof.

10. The composition of claim 9 wherein the cross-linking catalyst is thermal acid generators.

11. The composition of claim 9 wherein the cross-linking catalyst is selected from acids.

12. The composition of claim 9 wherein the cross-linking catalyst is selected from a mixture of thermal acid generators and acids.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 8, 2015
From: AZ ELECTRONIC MATERIALS USA CORP.
To: MERCK PATENT GMBH
Reel/Frame 034742/0206 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 25, 2005
From: CLARIANT INTERNATIONAL LTD
To: AZ ELECTRONIC MATERIALS USA CORP.
Reel/Frame 015942/0063 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2003
From: WU, HENGPENG; XIANG, ZHONG; SHAN, JIANHUI; DING-LEE, SHUJI; GONZALEZ, ELEAZAR B.
To: CLARIANT INTERNATIONAL LTD.
Reel/Frame 014179/0188 →